2023 |
Cossar PJ, Cardoso D, Mathwin D, Russell CC, Chiew B, Hamilton MP, et al., 'Wiskostatin and other carbazole scaffolds as off target inhibitors of dynamin I GTPase activity and endocytosis', European Journal of Medicinal Chemistry, 247 (2023) [C1]
Wiskostatin (1-(3,6-dibromo-9H-carbazol-9-yl)-3-(dimethylamino)propan-2-ol) (1) is a carbazole-based compound reported as a specific and relatively potent inhibitor of the N-WASP ... [more]
Wiskostatin (1-(3,6-dibromo-9H-carbazol-9-yl)-3-(dimethylamino)propan-2-ol) (1) is a carbazole-based compound reported as a specific and relatively potent inhibitor of the N-WASP actin remodelling complex (S-isomer EC50 = 4.35 µM; R-isomer EC50 = 3.44 µM). An NMR solution structure showed that wiskostatin interacts with a cleft in the regulatory GTPase binding domain of N-WASP. However, numerous studies have reported wiskostatin's actions on membrane transport and cytokinesis that are independent of the N-WASP-Arp2/3 complex pathway, but offer limited alternative explanation. The large GTPase, dynamin has established functional roles in these pathways. This study reveals that wiskostatin and its analogues, as well as other carbazole-based compounds, are inhibitors of helical dynamin GTPase activity and endocytosis. We characterise the effects of wiskostatin on in vitro dynamin GTPase activity, in-cell endocytosis, and determine the importance of wiskostatin functional groups on these activities through design and synthesis of libraries of wiskostatin analogues. We also examine whether other carbazole-based scaffolds frequently used in research or the clinic also modulate dynamin and endocytosis. Understanding off-targets for compounds used as research tools is important to be able to confidently interpret their action on biological systems, particularly when the target and off-targets affect overlapping mechanisms (e.g. cytokinesis and endocytosis). Herein we demonstrate that wiskostatin is a dynamin inhibitor (IC50 20.7 ± 1.2 µM) and a potent inhibitor of clathrin mediated endocytosis (IC50 = 6.9 ± 0.3 µM). Synthesis of wiskostatin analogues gave rise to 1-(9H-carbazol-9-yl)-3-((4-methylbenzyl)amino)propan-2-ol (35) and 1-(9H-carbazol-9-yl)-3-((4-chlorobenzyl)amino)propan-2-ol (43) as potent dynamin inhibitors (IC50 = 1.0 ± 0.2 µM), and (S)-1-(3,6-dibromo-9H-carbazol-9-yl)-3-(dimethylamino)propan-2-ol (8a) and (R)-1-(3,6-dibromo-9H-carbazol-9-yl)-3-(dimethylamino)propan-2-ol (8b) that are amongst the most potent inhibitors of clathrin mediated endocytosis yet reported (IC50 = 2.3 ± 3.3 and 2.1 ± 1.7 µM, respectively).
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Nova |
2023 |
Nguyen HT, Venter H, Woolford L, Young KA, Mccluskey A, Garg S, et al., 'Oral administration of a 2-aminopyrimidine robenidine analogue (NCL1 95) significantly reduces Staphylococcus aureus infection and reduces Escherichia coli infection in combination with sub -inhibitory colistin concentrations in a bioluminescent mouse model', ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, (2023) [C1]
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2023 |
Odell LR, Jones NC, Chau N, Robertson MJ, Ambrus JI, Deane FM, et al., 'The sulfonadyns: a class of aryl sulfonamides inhibiting dynamin I GTPase and clathrin mediated endocytosis are anti-seizure in animal models', RSC Medicinal Chemistry, 14 1492-1511 (2023) [C1]
We show that dansylcadaverine (1) a known in-cell inhibitor of clathrin mediated endocytosis (CME), moderately inhibits dynamin I (dynI) GTPase activity (IC50 45 µM) and transferr... [more]
We show that dansylcadaverine (1) a known in-cell inhibitor of clathrin mediated endocytosis (CME), moderately inhibits dynamin I (dynI) GTPase activity (IC50 45 µM) and transferrin (Tfn) endocytosis in U2OS cells (IC50 205 µM). Synthesis gave a new class of GTP-competitive dynamin inhibitors, the Sulfonadyns¿. The introduction of a terminal cinnamyl moiety greatly enhanced dynI inhibition. Rigid diamine or amide links between the dansyl and cinnamyl moieties were detrimental to dynI inhibition. Compounds with in vitro inhibition of dynI activity <10 µM were tested in-cell for inhibition of CME. These data unveiled a number of compounds, e.g. analogues 33 ((E)-N-(6-{[(3-(4-bromophenyl)-2-propen-1-yl]amino}hexyl)-5-isoquinolinesulfonamide)) and 47 ((E)-N-(3-{[3-(4-bromophenyl)-2-propen-1-yl]amino}propyl)-1-naphthalenesulfonamide)isomers that showed dyn IC50 <4 µM, IC50(CME) <30 µM and IC50(SVE) from 12-265 µM. Both analogues (33 and 47) are at least 10 times more potent that the initial lead, dansylcadaverine (1). Enzyme kinetics revealed these sulfonamide analogues as being GTP competitive inhibitors of dynI. Sulfonadyn-47, the most potent SVE inhibitor observed (IC50(SVE) = 12.3 µM), significantly increased seizure threshold in a 6 Hz mouse psychomotor seizure test at 30 (p = 0.003) and 100 mg kg-1 ip (p < 0.0001), with similar anti-seizure efficacy to the established anti-seizure medication, sodium valproate (400 mg kg-1). The Sulfonadyn¿ class of drugs target dynamin and show promise as novel leads for future anti-seizure medications.
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Nova |
2023 |
Sun J, Baker JR, Russell CC, Pham HNT, Goldsmith CD, Cossar PJ, et al., 'Novel piperazine-1,2,3-triazole leads for the potential treatment of pancreatic cancer', RSC MEDICINAL CHEMISTRY,
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2023 |
Sun J, Baker JR, Russell CC, Pham HNT, Goldsmith CD, Cossar PJ, et al., 'Novel piperazine-1,2,3-triazole leads for the potential treatment of pancreatic cancer', RSC Medicinal Chemistry, 14 2246-2267 [C1]
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Nova |
2023 |
Hopkins MD, Costello IJ, Brandeburg ZC, Slay EL, Zanders LA, Dunn CE, et al., 'Expansion of a Synthesized Library of
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Nova |
2023 |
Wright KM, Bowyer MC, McCluskey A, Holdsworth CI, 'Molecular Imprinting of Benzylpiperazine: A Comparison of the Self-Assembly and Semi-Covalent Approaches', INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 24 (2023) [C1]
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Nova |
2023 |
Sterling J, Baker JR, McCluskey A, Munoz L, 'Systematic literature review reveals suboptimal use of chemical probes in cell-based biomedical research.', Nat Commun, 14 3228 (2023) [C1]
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Nova |
2022 |
Sun J, Ambrus JI, Baker JR, Russell CC, Cossar PJ, Sakoff JA, et al., '3,5-Bis(trifluoromethyl)phenylsulfonamides, a novel pancreatic cancer active lead. Investigation of the terminal aromatic moiety.', Bioorg Med Chem Lett, 61 128591 (2022) [C1]
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Nova |
2022 |
Nguyen HT, Venter H, Woolford L, Young K, McCluskey A, Garg S, et al., 'Impact of a Novel Anticoccidial Analogue on Systemic Staphylococcus aureus Infection in a Bioluminescent Mouse Model', Antibiotics, 11 (2022) [C1]
In this study, we investigated the potential of an analogue of robenidine (NCL179) to expand its chemical diversity for the treatment of multidrug-resistant (MDR) bacterial infect... [more]
In this study, we investigated the potential of an analogue of robenidine (NCL179) to expand its chemical diversity for the treatment of multidrug-resistant (MDR) bacterial infections. We show that NCL179 exhibits potent bactericidal activity, returning minimum inhibitory concentra-tion/minimum bactericidal concentrations (MICs/MBCs) of 1¿2 µg/mL against methicillin-resistant Staphylococcus aureus, MICs/MBCs of 1¿2 µg/mL against methicillin-resistant S. pseudintermedius and MICs/MBCs of 2¿4 µg/mL against vancomycin-resistant enterococci. NCL179 showed synergistic activity against clinical isolates and reference strains of Acinetobacter baumannii, Escherichia coli, Klebsiella pneumoniae and Pseudomonas aeruginosa in the presence of sub-inhibitory concentrations of colistin, whereas NCL179 alone had no activity. Mice given oral NCL179 at 10 mg/kg and 50 mg/kg (4 × doses, 4 h apart) showed no adverse clinical effects and no observable histological effects in any of the organs examined. In a bioluminescent S. aureus sepsis challenge model, mice that received four oral doses of NCL179 at 50 mg/kg at 4 h intervals exhibited significantly reduced bacterial loads, longer survival times and higher overall survival rates than the vehicle-only treated mice. These results support NCL179 as a valid candidate for further development to treat MDR bacterial infections as a stand-alone antibiotic or in combination with existing antibiotic classes.
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Nova |
2022 |
Prichard KL, O'Brien NS, Murcia SR, Baker JR, McCluskey A, 'Role of Clathrin and Dynamin in Clathrin Mediated Endocytosis/Synaptic Vesicle Recycling and Implications in Neurological Diseases', FRONTIERS IN CELLULAR NEUROSCIENCE, 15 (2022) [C1]
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Nova |
2022 |
Stevens AJ, Abraham R, Young KA, Russell CC, McCluskey SN, Baker JR, et al., 'Antigiardial Activity of Novel Guanidine Compounds', CHEMMEDCHEM, 17 (2022) [C1]
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Nova |
2022 |
Odell LR, Robertson MJ, Young KA, McGeachie AB, Quan A, Robinson PJ, McCluskey A, 'Prodrugs of the Archetypal Dynamin Inhibitor Bis-T-22', CHEMMEDCHEM, 17 (2022) [C1]
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Nova |
2022 |
Pi H, Venter H, Russell CC, Young KA, McCluskey A, Page SW, et al., 'In Vitro Activity of Robenidine Analogues NCL259 and NCL265 against Gram-Negative Pathogens', ANTIBIOTICS-BASEL, 11 (2022) [C1]
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Nova |
2022 |
Baker JR, Cossar PJ, Blaskovich MAT, Elliott AG, Zuegg J, Cooper MA, et al., 'Amino Alcohols as Potential Antibiotic and Antifungal Leads', Molecules, 27 (2022) [C1]
Five focused compound libraries (forty-nine compounds), based on prior studies in our laboratory were synthesized and screened for antibiotic and anti-fungal activity against S. a... [more]
Five focused compound libraries (forty-nine compounds), based on prior studies in our laboratory were synthesized and screened for antibiotic and anti-fungal activity against S. aureus, E. coli, K. pneumoniae, P. aeruginosa, A. baumannii, C. albicans and C. neoformans. Low levels of activity, at the initial screening concentration of 32 µg/mL, were noted with analogues of (Z)-2-(3,4-dichlorophenyl)-3-phenylacrylonitriles which made up the first two focused libraries produced. The most promising analogues possessing additional substituents on the terminal aromatic ring of the synthesised acrylonitriles. Modifications of the terminal aromatic moiety were explored through epoxide installation flowed by flow chemistry mediated ring opening aminolysis with discreet sets of amines to the corresponding amino alcohols. Three new focused libraries were developed from substituted anilines, cyclic amines, and phenyl linked heterocyclic amines. The aniline-based compounds were inactive against the bacterial and fungal lines screened. The introduction of a cyclic, such as piperidine, piperazine, or morpholine, showed >50% inhibition when evaluated at 32 µg/mL compound concentration against methicillin-resistant Staphylococcus aureus. Examination of the terminal aromatic substituent via oxirane aminolysis allowed for the synthesis of three new focused libraries of afforded amino alcohols. Aromatic substituted piperidine or piperazine switched library activity from antibacterial to anti-fungal activity with ((Z)-2-(3,4-dichlorophenyl)-3-(4-(2-hydroxy-3-(4-methylpiperazin-1-yl)propoxy)phenyl)acrylonitrile), ((Z)-2-(3,4-dichlorophenyl)-3-(4-(2-hydroxy-3-(4-(4-hydroxyphenyl)piperazin-1-yl)propoxy)-phenyl)acrylonitrile) and ((Z)-3-(4-(3-(4-cyclohexylpiperazin-1-yl)-2-hydroxypropoxy)-phenyl)-2-(3,4-dichlorophenyl)-acrylonitrile) show-ing >95% inhibition of Cryptococcus neoformans var. grubii H99 growth at 32 µg/mL. While (Z)-3-(4-(3-(cyclohexylamino)-2-hydroxypropoxy)phenyl)-2-(3,4-dichlorophenyl)-acrylonitrile, (S,Z)-2-(3,4-dichlorophenyl)-3-(4-(2-hydroxy-3-(piperidin-1-yl)propoxy)phenyl)acrylonitrile, (R,Z)-2-(3,4-dichlorophenyl)-3-(4-(2-hydroxy-3-(piperidin-1-yl)propoxy)phenyl)acrylonitrile, (Z)-2-(3,4-dichloro-phenyl)-3-(4-(2-hydroxy-3-(D-11-piperidin-1-yl)propoxy)phenyl)-acrylonitrile, and (Z)-3-(4-(3-(4-cyclo-hexylpiperazin-1-yl)-2-hydroxypropoxy)-phenyl)-2-(3,4-dichlorophenyl)-acrylonitrile 32 µg/mL against Staphylococcus aureus.
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Nova |
2022 |
Baker JR, O Brien NS, Prichard KL, Robinson PJ, McCluskey A, Russell CC, 'Dynole 34-2 and Acrylo-Dyn 2-30, Novel Dynamin GTPase Chemical Biology Probes 221-238 (2022)
This protocol describes the chemical synthesis of the dynamin inhibitors Dynole 34-2 and Acrylo-Dyn 2-30, and their chemical scaffold matched partner inactive compounds. The chose... [more]
This protocol describes the chemical synthesis of the dynamin inhibitors Dynole 34-2 and Acrylo-Dyn 2-30, and their chemical scaffold matched partner inactive compounds. The chosen active and inactive paired compounds represent potent dynamin inhibitors and very closely related dynamin-inactive compounds, with the synthesis of three of the four compounds readily possible via a common intermediate. Combined with the assay data provided, this allows the interrogation of dynamin in vitro and potentially in vivo.
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2022 |
Russell CC, Prichard KL, O Brien NS, McCluskey A, Robinson PJ, Baker JR, 'Synthesis of Phthaladyn-29 and Naphthalimide-10, GTP Site Directed Dynamin GTPase Inhibitors 239-258 (2022)
Herein we describe the detailed synthesis of the dynamin inhibitors Phthaladyn-29 and Napthaladyn-10, and their chemical scaffold matched partner inactive compounds. Combined with... [more]
Herein we describe the detailed synthesis of the dynamin inhibitors Phthaladyn-29 and Napthaladyn-10, and their chemical scaffold matched partner inactive compounds. Combined with the assay data provided, this allows the interrogation of dynamin in vitro and potentially in vivo.
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2022 |
Odell LR, Chau N, Russell CC, Young KA, Gilbert J, Robinson PJ, et al., 'Pyrimidyn-Based Dynamin Inhibitors as Novel Cytotoxic Agents.', ChemMedChem, 17 e202100560 (2022) [C1]
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Nova |
2022 |
Zhang Q, Kounde CS, Mondal M, Greenfield JL, Baker JR, Kotelnikov S, et al., 'Light-mediated multi-target protein degradation using arylazopyrazole photoswitchable PROTACs (AP- PROTACs)', CHEMICAL COMMUNICATIONS, 58 10933-10936 (2022) [C1]
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Nova |
2021 |
Baker JR, Russell CC, Gilbert J, McCluskey A, Sakoff JA, 'Amino alcohol acrylonitriles as broad spectrum and tumour selective cytotoxic agents', RSC MEDICINAL CHEMISTRY, 12 929-+ (2021) [C1]
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Nova |
2021 |
Hang TN, Venter H, Veltman T, Williams R, O'Donovan LA, Russell CC, et al., 'In vitro synergistic activity of NCL195 in combination with colistin against Gram-negative bacterial pathogens', INTERNATIONAL JOURNAL OF ANTIMICROBIAL AGENTS, 57 (2021) [C1]
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Nova |
2021 |
Baker JR, Pollard BL, Lin AJS, Gilbert J, Paula S, Zhu X, et al., 'Modelling and Phenotypic Screening of NAP-6 and 10-Cl-BBQ, AhR Ligands Displaying Selective Breast Cancer Cytotoxicity in Vitro', CHEMMEDCHEM, 16 1499-1512 (2021) [C1]
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Nova |
2021 |
Sun J, Ambrus JI, Russell CC, Baker JR, Cossar PJ, Pirinen MJ, et al., 'Targeting the S100A2-p53 Interaction with a Series of 3,5-Bis(trifluoromethyl)benzene Sulfonamides: Synthesis and Cytotoxicity', ChemMedChem, 16 2851-2863 (2021) [C1]
In silico approaches identified 1, N-(6-((4-bromo- benzyl)amino)hexyl)-3,5-bis(trifluoromethyl)benzene sulfonamide, as a potential inhibitor of the S100A2-p53 protein-protein inte... [more]
In silico approaches identified 1, N-(6-((4-bromo- benzyl)amino)hexyl)-3,5-bis(trifluoromethyl)benzene sulfonamide, as a potential inhibitor of the S100A2-p53 protein-protein interaction, a validated pancreatic cancer drug target. Subsequent cytotoxicity screening revealed it to be a 2.97 µM cell growth inhibitor of the MiaPaCa-2 pancreatic cell line. This is in keeping with our hypothesis that inhibiting this interaction would have an anti-pancreatic cancer effect with S100A2, the validated PC drug target. A combination of focused library synthesis (three libraries, 24 compounds total) and cytotoxicity screening identified a propyl alkyl diamine spacer as optimal; the nature of the terminal phenyl substituent had limited impact on observed cytotoxicity, whereas N-methylation was detrimental to activity. In total 15 human cancer cell lines were examined, with most analogues showing broad-spectrum activity. Near uniform activity was observed against a panel of six pancreatic cancer cell lines: MiaPaCa-2, BxPC-3, AsPC-1, Capan-2, HPAC and PANC-1. In all cases there was good to excellent correlation between the predicted docking pose in the S100A2-p53 binding groove and the observed cytotoxicity, especially in the pancreatic cancer cell line with high endogenous S100A2 expression. This supports S100A2 as a pancreatic cancer drug target.
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Nova |
2021 |
Sun J, Baker JR, Russell CC, Cossar PJ, Ngoc Thuy Pham H, Sakoff JA, et al., 'Cytotoxic 1,2,3-Triazoles as Potential Leads Targeting the S100A2-p53 Complex: Synthesis and Cytotoxicity', ChemMedChem, 16 2864-2881 (2021) [C1]
In silico screening predicted 1 (N-(4-((4-(3-(4-(3-methoxyphenyl)-1H-1,2,3-triazol-1-yl)propyl)piperazin-1-yl) sulfonyl)-phenyl)acetamide) as an inhibitor of the S100A2-p53 protei... [more]
In silico screening predicted 1 (N-(4-((4-(3-(4-(3-methoxyphenyl)-1H-1,2,3-triazol-1-yl)propyl)piperazin-1-yl) sulfonyl)-phenyl)acetamide) as an inhibitor of the S100A2-p53 protein-protein interaction. S100A2 is a validated pancreatic cancer drug target. In the MiaPaCa-2 pancreatic cell line, 1 was a ~50 µM growth inhibitor. Synthesis of five focused compound libraries and cytotoxicity screening revealed increased activity from the presence of electron withdrawing moieties on the sulfonamide aromatic ring, with the 3,5-bis-CF3 Library 3 analogues the most active, with GI50 values of 0.91 (3-ClPh; 13 i; BxPC-3, Pancreas) to 9.0 µM (4-CH3; 13 d; PANC-1, Pancreas). Activity was retained against an expanded pancreatic cancer cell line panel (MiaPaCa-2, BxPC-3, AsPC-1, Capan-2, PANC-1 and HPAC) and the normal cell line MCF10A (breast). Bulky 4-disposed substituents on the terminal phenyl ring enhanced broad spectrum activity with growth inhibition values spanning 1.1 to 3.1 µM (4-C(CH3)3; 13 e; BxPC-3 and AsPC-1 (pancreas), respectively). Central alkyl spacer contraction from propyl to ethyl proved detrimental to activity with Library 4 and 5.5- to 10-fold less cytotoxic than the propyl linked Library 2 and Library 3. The data herein was consistent with the predicted binding poses of the compounds evaluated. The highest levels of cytotoxicity were observed with those analogues best capable of adopting a near identical pose to the p53-peptide in the S100A2-p53 binding groove.
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Nova |
2021 |
Tremblay CS, Chiu SK, Saw J, McCalmont H, Litalien V, Boyle J, et al., 'Small molecule inhibition of Dynamin-dependent endocytosis targets multiple niche signals and impairs leukemia stem cells (vol 11, 6211, 2020)', NATURE COMMUNICATIONS, 12 (2021)
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2021 |
Nguyen HT, O'Donovan LA, Venter H, Russell CC, McCluskey A, Page SW, et al., 'Comparison of Two Transmission Electron Microscopy Methods to Visualize Drug-Induced Alterations of Gram-Negative Bacterial Morphology', ANTIBIOTICS-BASEL, 10 (2021) [C1]
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Nova |
2021 |
Saifullah M, McCullum R, McCluskey A, Van VQ, 'Effect of drying techniques and operating conditions on the retention of color, phenolics, and antioxidant properties in dried lemon scented tea tree (Leptospermum petersonii) leaves', JOURNAL OF FOOD PROCESSING AND PRESERVATION, 45 (2021) [C1]
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Nova |
2021 |
Sun EWL, Matusica D, Wattchow DA, McCluskey A, Robinson PJ, Keating DJ, 'Dynamin regulates L cell secretion in human gut', Molecular and Cellular Endocrinology, 535 111398-111398 (2021) [C1]
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Nova |
2021 |
Stanton DT, Baker JR, McCluskey A, Paula S, 'Development and interpretation of a QSAR model for in vitro breast cancer (MCF-7) cytotoxicity of 2-phenylacrylonitriles', Journal of Computer-Aided Molecular Design, 35 613-628 (2021) [C1]
The Arylhydrocarbon Receptor (AhR), a member of the Per-ARNT-SIM transcription factor family, has been as a potential new target to treat breast cancer sufferers. A series of 2-ph... [more]
The Arylhydrocarbon Receptor (AhR), a member of the Per-ARNT-SIM transcription factor family, has been as a potential new target to treat breast cancer sufferers. A series of 2-phenylacrylonitriles targeting AhR has been developed that have shown promising and selective activity against cancerous cell lines while sparing normal non-cancerous cells. A quantitative structure¿activity relationship (QSAR) modeling approach was pursued in order to generate a predictive model for cytotoxicity to support ongoing synthetic activities and provide important structure-activity information for new structure design. Recent work conducted by us has identified a number of compounds that exhibited false positive cytotoxicity values in the standard MTT assay. This work describes a good quality model that not only predicts the activity of compounds in the MCF-7 breast cancer cell line, but was also able to identify structures that subsequently gave false positive values in the MTT assay by identifying compounds with aberrant biological behavior. This work not only allows the design of future breast cancer cytotoxic activity in vitro, but allows the avoidance of the synthesis of those compounds anticipated to result in anomalous cytotoxic behavior, greatly enhancing the design of such compounds.
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Nova |
2021 |
Tremblay CS, Ting SB, McCluskey A, Robinson PJ, Curtis DJ, 'Shutting the gate: targeting endocytosis in acute leukemia', Experimental Hematology, 104 17-31 (2021) [C1]
Endocytosis entails selective packaging of cell surface cargos in cytoplasmic vesicles, thereby controlling key intrinsic cellular processes as well as the response of normal and ... [more]
Endocytosis entails selective packaging of cell surface cargos in cytoplasmic vesicles, thereby controlling key intrinsic cellular processes as well as the response of normal and malignant cells to their microenvironment. The purpose of this review is to outline the latest advances in the development of endocytosis-targeting therapeutic strategies in hematological malignancies.
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Nova |
2020 |
Gilbert J, De Iuliis GN, McCluskey A, Sakoff JA, 'A novel naphthalimide that selectively targets breast cancer via the arylhydrocarbon receptor pathway', Scientific Reports, 10 (2020) [C1]
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Nova |
2020 |
Chew HY, De Lima PO, Gonzalez Cruz JL, Banushi B, Echejoh G, Hu L, et al., 'Endocytosis Inhibition in Humans to Improve Responses to ADCC-Mediating Antibodies', Cell, 180 895-914.e27 (2020) [C1]
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Nova |
2020 |
O'Brien NS, McCluskey A, 'A Facile Microwave and SnCl2 Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones', AUSTRALIAN JOURNAL OF CHEMISTRY, 73 1176-1186 (2020) [C1]
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Nova |
2020 |
Baker JR, Russell CC, Gilbert J, Sakoff JA, McCluskey A, 'Amino Alcohol Acrylonitriles as Activators of the Aryl Hydrocarbon Receptor Pathway: An Unexpected MTT Phenotypic Screening Outcome', ChemMedChem, 15 490-505 (2020) [C1]
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Nova |
2020 |
Alteen MG, Gros C, Meek RW, Cardoso DA, Busmann JA, Sangouard G, et al., 'A Direct Fluorescent Activity Assay for Glycosyltransferases Enables Convenient High-Throughput Screening: Application to O-GlcNAc Transferase', Angewandte Chemie - International Edition, 59 9601-9609 (2020) [C1]
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Nova |
2020 |
Baker JR, Sakoff JA, McCluskey A, 'Cover Image, Volume 40, Issue 3', Medicinal Research Reviews, 40 (2020)
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2020 |
Pi H, Hang TN, Venter H, Boileau AR, Woolford L, Garg S, et al., 'In vitroActivity of Robenidine Analog NCL195 in Combination With Outer Membrane Permeabilizers Against Gram-Negative Bacterial Pathogens and Impact on Systemic Gram-Positive Bacterial Infection in Mice', Frontiers in Microbiology, 11 (2020) [C1]
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Nova |
2020 |
Tremblay CS, Chiu SK, Saw J, McCalmont H, Litalien V, Boyle J, et al., 'Small molecule inhibition of Dynamin-dependent endocytosis targets multiple niche signals and impairs leukemia stem cells.', Nat Commun, 11 6211 (2020) [C1]
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Nova |
2020 |
Saifullah M, McCullum R, McCluskey A, Vuong Q, 'Comparison of conventional extraction technique with ultrasound assisted extraction on recovery of phenolic compounds from lemon scented tea tree (Leptospermum petersonii) leaves', Heliyon, 6 (2020) [C1]
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Nova |
2020 |
Cossar PJ, Lewis PJ, McCluskey A, 'Protein-protein interactions as antibiotic targets: A medicinal chemistry perspective', Medicinal Research Reviews, 40 469-494 (2020) [C1]
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Nova |
2020 |
Sun J, Russell CC, Scarlett CJ, McCluskey A, 'Small molecule inhibitors in pancreatic cancer', RSC MEDICINAL CHEMISTRY, 11 164-183 (2020) [C1]
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Nova |
2020 |
Alteen MG, Gros C, Meek RW, Cardoso DA, Busmann JA, Sangouard G, et al., 'A Direct Fluorescent Activity Assay for Glycosyltransferases Enables Convenient High-Throughput Screening: Application to
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2020 |
Baker JR, Sakoff JA, McCluskey A, 'The aryl hydrocarbon receptor (AhR) as a breast cancer drug target', Medicinal Research Reviews, 40 972-1001 (2020) [C1]
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Nova |
2020 |
Mihalas BP, Redgrove KA, Bernstein IR, Robertson MJ, McCluskey A, Nixon B, et al., 'Dynamin 2-dependent endocytosis is essential for mouse oocyte development and fertility', FASEB Journal, 34 5162-5177 (2020) [C1]
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Nova |
2019 |
Saifullah M, McCullum R, McCluskey A, Vuong Q, 'Effects of different drying methods on extractable phenolic compounds and antioxidant properties from lemon myrtle dried leaves', Heliyon, 5 (2019) [C1]
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Nova |
2019 |
Predebon MJ, Bond DR, Brzozowski J, Jankowski H, Deane F, Tarleton M, et al., 'The bispidinone derivative 3,7-Bis-[2-(S)-amino-3-(1H-indol-3-yl)-propionyl]-1,5-diphenyl-3,7-diazabicyclo[3.3.1]nonan-9-one dihydrochloride induces an apoptosis-mediated cytotoxic effect on pancreatic cancer cells in vitro', Molecules, 24 (2019) [C1]
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Nova |
2019 |
Al Otaibi A, Deane FM, Russell CC, Hizartzidis L, McCluskey SN, Sakoff JA, McCluskey A, 'A methanol and protic ionic liquid Ugi multicomponent reaction path to cytotoxic a-phenylacetamido amides', RSC Advances, 9 7652-7663 (2019) [C1]
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Nova |
2019 |
Zhou W, Stanger SJ, Anderson AL, Bernstein IR, De Iuliis GN, McCluskey A, et al., 'Mechanisms of tethering and cargo transfer during epididymosome-sperm interactions.', BMC biology, 17 35-35 (2019) [C1]
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Nova |
2019 |
Abraham RJ, Abraham S, Stevens AJ, Page SW, McCluskey A, Trott DJ, O'Handley RM, 'Aminoguanidines: New leads for treatment of Giardia duodenalis infection.', International Journal for Parasitology-Drugs and Drug Resistance, 10 38-44 (2019) [C1]
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Nova |
2019 |
Khazandi M, Pi H, Chan WY, Ogunniyi AD, Sim JXF, Venter H, et al., 'In vitro Antimicrobial Activity of Robenidine, Ethylenediaminetetraacetic Acid and Polymyxin B Nonapeptide Against Important Human and Veterinary Pathogens', FRONTIERS IN MICROBIOLOGY, 10 (2019) [C1]
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Nova |
2019 |
Russell CC, Stevens A, Young KA, Baker JR, McCluskey SN, Khazandi M, et al., 'Discovery of 4,6-bis(2-((E)-benzylidene)hydrazinyl)pyrimidin-2-Amine with Antibiotic Activity.', ChemistryOpen, 8 896-907 (2019) [C1]
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Nova |
2019 |
Hizartzidis L, Gilbert J, Gordon CP, Sakoff JA, McCluskey A, 'Synthesis and Cytotoxicity of Octahydroepoxyisoindole-7-carboxylic Acids and Norcantharidin-Amide Hybrids as Norcantharidin Analogues', CHEMMEDCHEM, 14 1152-1161 (2019) [C1]
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Nova |
2019 |
Luwor R, Morokoff AP, Amiridis S, D Abaco G, Paradiso L, Stylli SS, et al., 'Targeting Glioma Stem Cells by Functional Inhibition of Dynamin 2: A Novel Treatment Strategy for Glioblastoma', Cancer Investigation, 37 144-155 (2019) [C1]
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Nova |
2018 |
Baker JR, Gilbert J, Paula S, Zhu X, Sakoff JA, McCluskey A, 'Dichlorophenylacrylonitriles as AhR Ligands That Display Selective Breast Cancer Cytotoxicity in vitro', CHEMMEDCHEM, 13 1447-1458 (2018) [C1]
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Nova |
2018 |
Cossar PJ, Russell CC, McCluskey SN, Pope D, Bernhardt PV, McCluskey A, 'Crystal Structure of Ethyl 2,4-Dimethyl-1-phenyl-6-thioxo-1,6-dihydropyrimidine-5-carboxylate: The Product from the Reaction of Ethyl 3-Aminocrotonate, Phenylisothiocyanate and Acetic Anhydride', JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 48 91-95 (2018) [C1]
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Nova |
2018 |
Simone MI, Mares LJ, Eveleens CA, McCluskey A, Pappin BB, Kiefel MJ, Houston TA, 'Back to (non-)Basics: An Update on Neutral and Charge-Balanced Glycosidase Inhibitors', MINI-REVIEWS IN MEDICINAL CHEMISTRY, 18 812-827 (2018) [C1]
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Nova |
2018 |
Gilbert J, De Iuliis GN, Tarleton M, McCluskey A, Sakoff JA, '(Z)-2-(3,4-dichlorophenyl)-3-(1H-pyrrol-2-yl)acrylonitrile exhibits selective antitumor activity in breast cancer cell lines via the aryl hydrocarbon receptor pathway', Molecular Pharmacology, 93 168-177 (2018) [C1]
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Nova |
2018 |
Otaibi AA, McCluskey A, 'Ionic liquids, microwave irradiation, and the synthesis of aryl Weinreb amides', Monatshefte fur Chemie, 149 519-525 (2018) [C1]
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Nova |
2018 |
Apodaca DC, Turner N, Bowyer M, Holdsworth CZ, McCluskey A, 'Tailoring the Preparation of Fluorescent Molecularly Imprinted Polymers (MIPs) Toward the Detection of Chemical Warfare Agents', Sensors and Tranducers Journal, 28 43-53 (2018) [C1]
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Nova |
2018 |
Cossar PJ, Baker JR, Cain N, McCluskey A, 'In situ epoxide generation by dimethyldioxirane oxidation and the use of epichlorohydrin in the flow synthesis of a library of beta-amino alcohols', ROYAL SOCIETY OPEN SCIENCE, 5 (2018) [C1]
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Nova |
2018 |
Ghods A, Gilbert J, Baker JR, Russell CC, Sakoff JA, McCluskey A, 'A focused library synthesis and cytotoxicity of quinones derived from the natural product bolinaquinone', Royal Society Open Science, 5 (2018) [C1]
Bolinaquinone is a natural product that is a structurally complex, cytotoxic sesquiterpene quinone. A scaffold simplification and focused library approach using a microwave-assist... [more]
Bolinaquinone is a natural product that is a structurally complex, cytotoxic sesquiterpene quinone. A scaffold simplification and focused library approach using a microwave-assisted Suzuki coupling gave 32 bolinaquinone analogues with good-to-excellent cytotoxicity profiles. Mono-arylbenzoquinones, Library A, were preferentially toxic towards BE2-C (neuroblastoma) cells with growth inhibition (GI50) values of 4¿12 µM; only the 3,4-dimethoxyphenyl 23 and 3-biphenyl 28 variants were broad-spectrum active¿HT29 (colon carcinoma), U87 and SJ-G2 (glioblastoma), MCF-7 (breast carcinoma), A2780 (ovarian carcinoma), H460 (lung carcinoma), A431 (skin carcinoma), Du145 (prostate carcinoma), BE2-C (neuroblastoma), MIA (pancreatic carcinoma) and SMA (spontaneous murine astrocytoma). Library B with a second aryl moiety exhibited broad-spectrum cytotoxicity with MCF-7 cells¿ GI50 values of 5.6 ± 0.7 and 5.1 ± 0.5 µM for 2,5-dimethoxy-3-(naphthalene-1-yl)-6-(naphthalene-3-yl) 33 and 2,5-dimethoxy-3-(biaryl-2-yl)-6-(naphthalene-3-yl) 36, respectively. Similar potencies were also noted with 2,5-dimethoxy-3,6-diphenyl 30 against A2780 (GI50 = 5.9 ± 0.0 µM) and with 2,5-dimethoxy-3-(biaryl-3-yl)-6-(naphthalene-3-yl) 37 against HT29 (GI50 = 5.4 ± 0.4 µM), while the 3,4-dimethoxy mono-aryl analogue 23 exhibited good levels of activity against A2780 (GI50 = 3.8 ± 0.75 µM), the neuroblastoma cell line BE2-C (GI50 = 3 ± 0.35 µM) and SMA (GI50 = 3.9 ± 0.54 µM). Introduction of the amino-substituted Library C gave 2-(naphthalen-1-yl)-5-(naphthalen-3-yl)-3,6-bis(propylamino) 43, with excellent activity against HT29 (0.08 ± 0.0 µM), MCF-7 (0.17 ± 0.1 µM), A2780 (0.14 ± 0.1 µM), A431 (0.11 ± 0.0 µM), Du145 (0.16 ± 0.1 µM), BE2-C (0.08 ± 0.0 µM) and MIA (0.1 ± 0.0 µM).
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Nova |
2018 |
Trinh TN, McCluskey A, 'A multicomponent access to 1,3-thiazine-6-phenylimino-5-carboxylates (vol 57, pg 3256, 2016)', TETRAHEDRON LETTERS, 59 3155-3156 (2018)
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Nova |
2018 |
Russell CC, Stevens A, Pi H, Khazandi M, Ogunniyi AD, Young KA, et al., 'Gram-Positive and Gram-Negative Antibiotic Activity of Asymmetric and Monomeric Robenidine Analogues', CHEMMEDCHEM, 13 2573-2580 (2018) [C1]
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Nova |
2018 |
Clarke Z, Barnes E, Prichard K, Mares L, Clegg J, McCluskey A, et al., 'The crystal structures of 3-O-benzyl-1,2-O-isopropylidene-
5-O-methanesulfonyl-6-O-triphenylmethyl-
a-D-glucofuranose and its azide
displacement product', Acta Crystallographica Section E, 74 862-867 (2018) [C1]
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Nova |
2017 |
Zhou W, De Iuliis GN, Turner AP, Reid AT, Anderson AL, McCluskey A, et al., 'Developmental expression of the dynamin family of mechanoenzymes in the mouse epididymis', BIOLOGY OF REPRODUCTION, 96 159-173 (2017) [C1]
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Nova |
2017 |
Aggarwal A, Hitchen TL, Ootes L, McAllery S, Wong A, Nguyen K, et al., 'HIV infection is influenced by dynamin at 3 independent points in the viral life cycle', TRAFFIC, 18 392-410 (2017) [C1]
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Nova |
2017 |
Trinh TN, McLaughlin EA, Gordon CP, Bernstein IR, Pye VJ, Redgrove KA, McCluskey A, 'Small molecule Hedgehog pathway antagonists', ORGANIC & BIOMOLECULAR CHEMISTRY, 15 3046-3059 (2017) [C1]
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Nova |
2017 |
Jensen DD, Lieu T, Halls ML, Veldhuis NA, Imlach WL, Mai QN, et al., 'Neurokinin 1 receptor signaling in endosomes mediates sustained nociception and is a viable therapeutic target for prolonged pain relief', SCIENCE TRANSLATIONAL MEDICINE, 9 (2017) [C1]
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Nova |
2017 |
Cossar PJ, Ma C, Gordon CP, Ambrus JI, Lewis PJ, McCluskey A, 'Identification and validation of small molecule modulators of the NusB-NusE interaction', BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 27 162-167 (2017) [C1]
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Nova |
2017 |
Zhou W, Anderson AL, Turner AP, De Iuliis GN, McCluskey A, McLaughlin EA, Nixon B, 'Characterization of a novel role for the dynamin mechanoenzymes in the regulation of human sperm acrosomal exocytosis.', Molecular Human Reproduction, 23 657-673 (2017) [C1]
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Nova |
2017 |
Deane FM, Lin AJS, Hains PG, Pilgrim SL, Robinson PJ, McCluskey A, 'FD5180, a Novel Protein Kinase Affinity Probe, and the Effect of Bead Loading on Protein Kinase Identification', ACS OMEGA, 2 3828-3838 (2017) [C1]
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Nova |
2017 |
Cossar PJ, Abdel-Hamid MK, Ma C, Sakoff JA, Trinh TN, Gordon CP, et al., 'Small-Molecule Inhibitors of the NusB-NusE Protein-Protein Interaction with Antibiotic Activity', ACS OMEGA, 2 3839-3857 (2017) [C1]
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Nova |
2017 |
Spare LK, Falsetta P, Gilbert J, Harman DG, Baker MA, Li F, et al., 'Cytotoxicity of a Series of Norcantharidin-Inspired Tetrahydroepoxyisoindole Carboxamides', CHEMMEDCHEM, 12 130-145 (2017) [C1]
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Nova |
2017 |
Ogunniyi AD, Khazandi M, Stevens AJ, Sims SK, Page SW, Garg S, et al., 'Evaluation of robenidine analog NCL195 as a novel broad-spectrum antibacterial agent', PLOS ONE, 12 (2017) [C1]
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Nova |
2017 |
Odell LR, Abdel-Hamid MK, Hill TA, Ngoc C, Young KA, Deane FM, et al., 'Pyrimidine-Based Inhibitors of Dynamin I GTPase Activity: Competitive Inhibition at the Pleckstrin Homology Domain', JOURNAL OF MEDICINAL CHEMISTRY, 60 349-361 (2017) [C1]
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2016 |
Redgrove KA, Bernstein IR, Pye VJ, Mihalas BP, Sutherland JM, Nixon B, et al., 'Dynamin 2 is essential for mammalian spermatogenesis', SCIENTIFIC REPORTS, 6 (2016) [C1]
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Nova |
2016 |
Zaleta-Pinet D, McCluskey A, Hall S, Brophy J, Ashhurst-Smith C, Sakoff J, Van Altena I, 'The Use of the Toxic Plant Myoporum montanum in a Traditional Australian Aboriginal Medicine', Australian Journal of Chemistry, 69 161-168 (2016) [C1]
Plants from the family Myoporaceae, which includes the genus Myoporum, are extremely prized by the Australian Aboriginal people for their medicinal properties. Leaves from a plant... [more]
Plants from the family Myoporaceae, which includes the genus Myoporum, are extremely prized by the Australian Aboriginal people for their medicinal properties. Leaves from a plant, which was subsequently identified as Myoporum montanum, were provided for chemical investigation by representatives of an Aboriginal community from the Northern Tablelands district of northern New South Wales, Australia. Acetone extraction of the leaves provided a complex mixture of compounds including sesquiterpene hydrocarbons and more polar furanosesquiterpenes, which were identified by gas-liquid chromatography and retention indices (sesquiterpene hydrocarbons) and spectrometric techniques (furanosesquiterpenes). The major compounds found in a water extract were studied for their antibacterial activity using a disc diffusion assay and for their cell growth inhibition activity. The acetone extract contained sesquiterpene hydrocarbons (~30% of the total extract) in which the major compounds were germacrene-D and bicyclogermacrene. In addition, the extract contained five known toxic furanosesquiterpenes: myoporum ketol, (-)-10,11-dehydroisomyodesmone, (+)-10,11-dehydromyodesmone, 10,11-dehydromyoporum ketol, (-)-10,11-dehydromyoporone, and (±)-myoporone. An aqueous extract of the leaves, emulating the medicinal tea used by the Australian Aboriginal community, was found not to contain significant quantities of the sesquiterpene hydrocarbons and the most toxic furanosesquiterpenes. (±)-Myoporone and (-)-10,11-dehydromyoporone remained in the extract as well as a new furanosesquiterpene, 11-hydroxymyoporone. These three compounds were found to have significant antibacterial activity against Staphylococcus epidermidis, Enterococcus faecalis, and Moraxella catarrhalis but low cytotoxicity against a range of cancer cell lines and normal breast cells at 25µM.
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Nova |
2016 |
Abraham RJ, Stevens AJ, Young KA, Russell C, Qvist A, Khazandi M, et al., 'Robenidine Analogues as Gram-Positive Antibacterial Agents', JOURNAL OF MEDICINAL CHEMISTRY, 59 2126-2138 (2016) [C1]
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Nova |
2016 |
Robertson MJ, Horatscheck A, Sauer S, von Kleist L, Baker JR, Stahlschmidt W, et al., '5-Aryl-2-(naphtha-1-yl)sulfonamido-thiazol-4(5H)-ones as clathrin inhibitors', ORGANIC & BIOMOLECULAR CHEMISTRY, 14 11266-11278 (2016) [C1]
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Nova |
2016 |
Trinh TN, McCluskey A, 'A multicomponent access to 1,3-thiazine-6-phenylimino-5-carboxylates', TETRAHEDRON LETTERS, 57 3256-3259 (2016) [C1]
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Nova |
2016 |
Trinh TN, McLaughlin EA, Abdel-Hamid MK, Gordon CP, Bernstein IR, Pye V, et al., 'Quinolone-1-(2H)-ones as hedgehog signalling pathway inhibitors', ORGANIC & BIOMOLECULAR CHEMISTRY, 14 6304-6315 (2016) [C1]
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Nova |
2016 |
Lin AJS, Russell CC, Baker JR, Frailey SL, Sakoff JA, McCluskey A, 'A facile hybrid 'flow and batch' access to substituted 3,4-dihydro-2: H -benzo [b] [1,4]oxazinones', Organic and Biomolecular Chemistry, 14 8732-8742 (2016) [C1]
We describe a simple flow chemistry approach to libraries of ethyl 3-oxo-2-(substituted-phenylamino)-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carboxylates (12a-l) and N-ethyl-3-oxo-2... [more]
We describe a simple flow chemistry approach to libraries of ethyl 3-oxo-2-(substituted-phenylamino)-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carboxylates (12a-l) and N-ethyl-3-oxo-2-(substituted-phenylamino)-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carboxamides (13a-l) in 38-87% yields. This scaffold is poorly described in the chemical literature. Screening against a panel of 11 cancer and one normal cell line showed that the amide linked library 13a-l was devoid of toxicity. Whereas the ester linked analogues 12b, 12c, 12g, 12j and 12l were highly cytotoxic with growth inhibition (GI50) values from 0.34 to >50 µM across all cell lines, with the 2-OH-Ph substituted 12l analogue presenting with sub-micromolar potency against the A2780 (ovarian; 0.34 ± 0.04 µM), BEC-2 (glioblastoma; 0.35 ± 0.06 µM), MIA (pancreas; 0.91 ± 0.054 µM) and SMA (murine glioblastoma; 0.77 ± 0.029 µM) carcinoma cell lines. Interestingly, the U87 glioblastoma cell line showed inherent resistance to growth inhibition by all analogues (GI50 32 to >50 µM) while the A2780 cells were highly sensitive (GI50 3.8-0.34 µM), suggesting that the analogues developed herein may be valuable lead compounds for the development of ovarian carcinoma specific cytotoxic agents. The differences in amide versus ester cytotoxicity was consitent with esterase cleaveage to release the cytotoxic warhead.
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Nova |
2015 |
Cossar PJ, Hizartzidis L, Simone M, McCluskey A, Gordon CP, 'The expanding utility of continuous flow hydrogenation', Organic and Biomolecular Chemistry, 26 7119-7130 (2015) [C1]
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Nova |
2015 |
Lees JG, Gorgani NN, Ammit AJ, McCluskey A, Robinson PJ, O'Neill GM, 'Role of dynamin in elongated cell migration in a 3D matrix', Biochimica et Biophysica Acta - Molecular Cell Research, 1853 611-618 (2015) [C1]
The use of 3-dimensional (3D) collagen gels has yielded new insights into the migratory behaviour of cancer cells. While the large GTPase dynamin has emerged as an important regul... [more]
The use of 3-dimensional (3D) collagen gels has yielded new insights into the migratory behaviour of cancer cells. While the large GTPase dynamin has emerged as an important regulator of cancer cell migration and invasion under 2D conditions, its role in 3D migration is unclear. We have used a potent dynamin modulator, a bis-tyrphostin derivative, Ryngo® 1-23, to investigate the role of dynamin in 3D migration in 3 different cell lines. The compound specifically inhibits persistent, elongated 3D migration in U87MG and SMA-560 cells. Treated U87MG cells adopt a rounded morphology that is not due to apoptosis, loss of matrix metalloprotease activity or inhibition of clathrin-mediated endocytosis. Given that Ryngo 1-23 is known to regulate dynamin oligomerisation and actin dynamics at the leading edge, we analysed actin filament distribution. Ryngo 1-23 induced a switch in actin filament organization in 3D cultures resulting in the generation of multiple short actin-rich microspikes. Correlated with the change in actin filament distribution, cells displayed reduced collagen gel contraction. Since acto-myosin force transmission to the extra-cellular matrix underpins persistent, elongated migration, our results suggest that Ryngo 1-23 modulates this process in 3D migration via dynamin-mediated regulation of acto-myosin force transmission to the extra-cellular matrix.
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Nova |
2015 |
Zayas HA, McCluskey A, Bowyer MC, Holdsworth CI, 'Potentiometric determination of acid dissociation constants of novel biaryl monomers', Analytical Methods, 7 8206-8211 (2015) [C1]
The acid dissociation constants (pKas) of a number of novel polymerisable vinyl biaryl compounds, 4-(4'-ethenylphenyl)-pyridine (M1), 4'-ethenyl-(1,1'-biphenyl)-4-o... [more]
The acid dissociation constants (pKas) of a number of novel polymerisable vinyl biaryl compounds, 4-(4'-ethenylphenyl)-pyridine (M1), 4'-ethenyl-(1,1'-biphenyl)-4-ol (M2), 4'-ethenyl-N,N-dimethyl-(1,1'-biphenyl)-3-amine (M3), 4'-ethenyl-(1,1'-biphenyl)-4-methanol (M4), 4'-ethenyl-N,N-dimethyl-(1,1'-biphenyl)-4-amine (M5), 4'-ethenyl-(1,1'-biphenyl)-4-carboxylic acid (M6), 4'-ethenyl-4-hydroxy-5-methyl-(1,1'-biphenyl)-3-carboxaldehyde (M7) were determined in a mixed solvent (THF-water) potentiometric titration at 25 °C and subsequent extrapolation to pure water via the Yasuda-Shedlovsky method. The acidity and basicity of the compounds in THF-water mixtures was observed to decrease with increasing THF fraction and is attributed to the corresponding decrease in the dielectric constant of the solution. To the best of our knowledge, this is the first reported study of pKa values undertaken for this class of compounds. The biaryls, M1-M7, were prepared by microwave-assisted Suzuki cross coupling of 4-vinylphenyl boronic acid with the appropriate aryl bromide and were custom designed for use as functional monomers in the synthesis of molecularly imprinted polymers.
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Nova |
2015 |
Daniel JA, Chau N, Abdel-Hamid MK, Hu L, von Kleist L, Whiting A, et al., 'Phenothiazine-derived antipsychotic drugs inhibit dynamin and clathrin-mediated endocytosis', Traffic, (2015) [C1]
Chlorpromazine is a phenothiazine-derived antipsychotic drug (APD) that inhibits clathrin-mediated endocytosis (CME) in cells by an unknown mechanism. We examined whether its acti... [more]
Chlorpromazine is a phenothiazine-derived antipsychotic drug (APD) that inhibits clathrin-mediated endocytosis (CME) in cells by an unknown mechanism. We examined whether its action and that of other APDs might be mediated by the GTPase activity of dynamin. Eight of eight phenothiazine-derived APDs inhibited dynamin I (dynI) in the 2-12µm range, the most potent being trifluoperazine (IC<inf>50</inf> 2.6±0.7µm). They also inhibited dynamin II (dynII) at similar concentrations. Typical and atypical APDs not based on the phenothiazine scaffold were 8- to 10-fold less potent (haloperidol and clozapine) or were inactive (droperidol, olanzapine and risperidone). Kinetic analysis showed that phenothiazine-derived APDs were lipid competitive, while haloperidol was uncompetitive with lipid. Accordingly, phenothiazine-derived APDs inhibited dynI GTPase activity stimulated by lipids but not by various SH3 domains. All dynamin-active APDs also inhibited transferrin (Tfn) CME in cells at related potencies. Structure-activity relationships (SAR) revealed dynamin inhibition to be conferred by a substituent group containing a terminal tertiary amino group at the N2 position. Chlorpromazine was previously proposed to target AP-2 recruitment in the formation of clathrin-coated vesicles (CCV). However, neither chlorpromazine nor thioridazine affected AP-2 interaction with amphiphysin or clathrin. Super-resolution microscopy revealed that chlorpromazine blocks neither clathrin recruitment by AP-2, nor AP-2 recruitment, showing that CME inhibition occurs downstream of CCV formation. Overall, potent dynamin inhibition is a shared characteristic of phenothiazine-derived APDs, but not other typical or atypical APDs, and the data indicate that dynamin is their likely in-cell target in endocytosis.
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Nova |
2015 |
Rixson JE, Abraham JR, Egoshi Y, Skelton BW, Young K, Gilbert J, et al., 'The synthesis and biological activity of novel anthracenone-pyranones and anthracenone-furans', Bioorganic and Medicinal Chemistry, 23 3552-3565 (2015) [C1]
Abstract An efficient and divergent methodology for the synthesis of new anthracenone-pyranones and anthracenone-furans is described. Key reactions discussed in these syntheses in... [more]
Abstract An efficient and divergent methodology for the synthesis of new anthracenone-pyranones and anthracenone-furans is described. Key reactions discussed in these syntheses include an aldehyde promoted annulation with a ß-keto-sulfoxide, a domino alkyne insertion/carbonylation/Nu-acylation and a DMEDA promoted Castro-Stephens reaction. We also report the in vitro growth inhibition of these compounds in a range of human cancer cells. The natural product BE-26554A displayed good cell growth activity on BE2-C neuroblastoma and SMA glioblastoma cell lines at 0.17 and 0.16 µM (GI50), respectively. Of note, were a CF3 functionalised anthracenone 4-pyranone (chromone) derivative 22, and an anthracenone-furan derivative 54 which displayed 0.20 µM and 0.38 µM growth inhibition, respectively, in the BE2-C neuroblastoma cell line.
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Nova |
2015 |
Abdel-Hamid MK, Macgregor KA, Odell LR, Chau N, Mariana A, Whiting A, et al., '1,8-Naphthalimide derivatives: New leads against dynamin i GTPase activity', Organic and Biomolecular Chemistry, 13 8016-8028 (2015) [C1]
Fragment-based in silico screening against dynamin I (dynI) GTPase activity identified the 1,8-naphthalimide framework as a potential scaffold for the design of new inhibitors tar... [more]
Fragment-based in silico screening against dynamin I (dynI) GTPase activity identified the 1,8-naphthalimide framework as a potential scaffold for the design of new inhibitors targeting the GTP binding pocket of dynI. Structure-based design, synthesis and subsequent optimization resulted in the development of a library of 1,8-naphthalimide derivatives, called the Naphthaladyn¿ series, with compounds 23 and 29 being the most active (IC<inf>50</inf> of 19.1 ± 0.3 and 18.5 ± 1.7 µM respectively). Compound 29 showed effective inhibition of clathrin-mediated endocytosis (IC<inf>50(CME)</inf> 66 µM). The results introduce 29 as an optimised GTP-competitive lead Naphthaladyn¿ compound for the further development of naphthalimide-based dynI GTPase inhibitors.
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Nova |
2015 |
Reid AT, Anderson AL, Roman SD, McLaughlin EA, McCluskey A, Robinson PJ, et al., 'Glycogen synthase kinase 3 regulates acrosomal exocytosis in mouse spermatozoa via dynamin phosphorylation', FASEB JOURNAL, 29 2872-2882 (2015) [C1]
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Nova |
2015 |
Russell C, Lin AJS, Hains P, Simone MI, Robinson PJ, Mccluskey A, 'An integrated flow and microwave approach to a broad spectrum protein kinase inhibitor', RSC Advances, 5 93433-93437 (2015) [C1]
The protein kinase inhibitor CTx-0152960 (6, 2-((5-chloro-2-((4-morpholinophenyl)amino)pyrimidin-4-yl)amino)-N-methylbenzamide), and the piperazinyl analogue, CTx-0294885 (7, 2-((... [more]
The protein kinase inhibitor CTx-0152960 (6, 2-((5-chloro-2-((4-morpholinophenyl)amino)pyrimidin-4-yl)amino)-N-methylbenzamide), and the piperazinyl analogue, CTx-0294885 (7, 2-((5-chloro-2-((4-piperazin-1-ylphenyl)amino)pyrimidin-4-yl)amino)-N-methylbenzamide), were prepared using a hybrid flow and microwave approach. The use of flow chemistry approaches avoided the need for Boc-protection of piperidine in the key SNAr coupling with 1-fluoro-4-nitrobenzene. Microwave coupling of 4-morphilinoaniline 8 and 4-(piperazine-1-yl)aniline 9 with 2-(2,5-dichloropyrimidine-4-ylamino)-N-methylbenzamide 10, proved to be the most efficacious route to the target analogues 6 and 7. This hybrid methodology reduced the number of synthetic steps, gave enhanced overall yields and increased atom economy through step reduction and minimal requirement for chromatographic purification, relative to the original batch synthesis approach.
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Nova |
2015 |
Jackson J, Papadopulos A, Meunier FA, McCluskey A, Robinson PJ, Keating DJ, 'Small molecules demonstrate the role of dynamin as a bi-directional regulator of the exocytosis fusion pore and vesicle release.', Mol Psychiatry, 20 810-819 (2015) [C1]
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Nova |
2015 |
Caì Y, Postnikova EN, Bernbaum JG, Yú S, Mazur S, Deiuliis NM, et al., 'Simian hemorrhagic fever virus cell entry is dependent on CD163 and uses a clathrin-mediated endocytosis-like pathway', Journal of Virology, 89 844-856 (2015) [C1]
Simian hemorrhagic fever virus (SHFV) causes a severe and almost uniformly fatal viral hemorrhagic fever in Asian macaques but is thought to be nonpathogenic for humans. To date, ... [more]
Simian hemorrhagic fever virus (SHFV) causes a severe and almost uniformly fatal viral hemorrhagic fever in Asian macaques but is thought to be nonpathogenic for humans. To date, the SHFV life cycle is almost completely uncharacterized on the molecular level. Here, we describe the first steps of the SHFV life cycle. Our experiments indicate that SHFV enters target cells by lowpH- dependent endocytosis. Dynamin inhibitors, chlorpromazine, methyl-ß-cyclodextrin, chloroquine, and concanamycin A dramatically reduced SHFV entry efficiency, whereas the macropinocytosis inhibitors EIPA, blebbistatin, and wortmannin and the caveolin-mediated endocytosis inhibitors nystatin and filipin III had no effect. Furthermore, overexpression and knockout study and electron microscopy results indicate that SHFV entry occurs by a dynamin-dependent clathrin-mediated endocytosislike pathway. Experiments utilizing latrunculin B, cytochalasin B, and cytochalasin D indicate that SHFV does not hijack the actin polymerization pathway. Treatment of target cells with proteases (proteinase K, papain, a-chymotrypsin, and trypsin) abrogated entry, indicating that the SHFV cell surface receptor is a protein. Phospholipases A2 and D had no effect on SHFV entry. Finally, treatment of cells with antibodies targeting CD163, a cell surface molecule identified as an entry factor for the SHFVrelated porcine reproductive and respiratory syndrome virus, diminished SHFV replication, identifying CD163 as an important SHFV entry component.
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Nova |
2014 |
Abdel-Hamid MK, McCluskey A, 'In Silico docking, molecular dynamics and binding energy insights into the bolinaquinone-clathrin terminal domain binding site', Molecules, 19 6609-6622 (2014) [C1]
Clathrin-mediated endocytosis (CME) is a process that regulates selective internalization of important cellular cargo using clathrin-coated vesicles. Perturbation of this process ... [more]
Clathrin-mediated endocytosis (CME) is a process that regulates selective internalization of important cellular cargo using clathrin-coated vesicles. Perturbation of this process has been linked to many diseases including cancer and neurodegenerative conditions. Chemical proteomics identified the marine metabolite, 2-hydroxy-5-methoxy-3-(((1S,4aS,8aS)-1,4a,5-Trimethyl-1,2,3,4,4a,7, 8,8a-octahydronaphthalen-2-yl)methyl)cyclohexa-2,5-diene-1,4-dione (bolinaquinone) as a clathrin inhibitor. While being an attractive medicinal chemistry target, the lack of data about bolinaquinone's mode of binding to the clathrin enzyme represents a major limitation for its structural optimization. We have used a molecular modeling approach to rationalize the observed activity of bolinaquinone and to predict its mode of binding with the clathrin terminal domain (CTD). The applied protocol started by global rigid-protein docking followed by flexible docking, molecular dynamics and linear interaction energy calculations. The results revealed the potential of bolinaquinone to interact with various pockets within the CTD, including the clathrin-box binding site. The results also highlight the importance of electrostatic contacts over van der Waals interactions for proper binding between bolinaquinone and its possible binding sites. This study provides a novel model that has the potential to allow rapid elaboration of bolinaquinone analogues as a new class of clathrin inhibitors. © 2014 by the authors.
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Nova |
2014 |
Hizartzidis L, Tarleton M, Gordon CP, McCluskey A, 'Chemoselective flow hydrogenation approaches to isoindole-7-carboxylic acids and 7-oxa-bicyclio[2.2.1]heptanes', RSC Advances, 4 9709-9722 (2014) [C1]
Two libraries of highly decorated norcantharidin analogues were accessed via a series of sequential chemoselective flow hydrogenations and solvent-free transformations. Utilising ... [more]
Two libraries of highly decorated norcantharidin analogues were accessed via a series of sequential chemoselective flow hydrogenations and solvent-free transformations. Utilising a 10% Pd/C catalyst, modifications to reaction parameters (H2 pressure, temperature and flow rate conditions) allowed facile access to effect selective direct reductive aminations and olefin reductions in the presence of furan, benzyl and nitrile moieties were established. The use of 20% Pd(OH)2/C; Pd tetrakis; 5% Pt/C (sulfided) gave mixtures of furan and olefin (both reduced) and olefin reduced products. RuO2; 0.5% Re/C and Re2O7 resulted in no reduction. Concurrent olefin and nitrile reduction was achieved in the presence of furan moieties by employing a RANEY® nickel catalyst. In total, 31 reaction conditions were examined using less than 200 mg of reagents allowing optimised conditions to be efficiently determined. These optimised hydrogenation conditions afforded desired analogues in near quantitative yields thus removing the requirements of reaction workup and chromatography. © 2014 The Royal Society of Chemistry.
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Al Otaibi A, Gordon CP, Gilbert J, Sakoff JA, McCluskey A, 'The influence of ionic liquids on the Knoevenagel condensation of 1H-pyrrole-2-carbaldehyde with phenyl acetonitriles-cytotoxic 3-substituted-(1H-pyrrol-2-yl)acrylonitriles', RSC Advances, 4 19806-19813 (2014) [C1]
The Knoevenagel condensation of a series of substituted phenyl acetonitriles with 1H-pyrrole-2-carbaldehyde was examined in seven 1-butyl-3-methylimidazolium based ionic liquids a... [more]
The Knoevenagel condensation of a series of substituted phenyl acetonitriles with 1H-pyrrole-2-carbaldehyde was examined in seven 1-butyl-3-methylimidazolium based ionic liquids and three protic ionic liquids. Of these [BMIM][Br] and [BMIM][OH], with catalytic piperidine, proved most efficient affording 3-substituted-(1H-pyrrol-2-yl)acrylonitriles 3-17 in good to excellent yields (98%) whilst utilisation of the protic ionic liquid propyl ammonium nitrate resulted in reduced yields (0-66%). Screening of the 3-substituted-(1H-pyrrol-2-yl)acrylonitriles analogues 3-17 against a panel of 11 cancer cell lines and one normal cell line allowed the identification of a series of compounds with broad spectrum cytotoxicity, but more interestingly a significant degree of MCF-7 breast cancer cell line specificity was evident with 6 (7 to >25 fold) and 13 (5.7 to >80 fold). Other analogues show high level of efficacy against specific cell lines with 10 showing excellent activity against MCF-7 (GI50 = 1.7 µM) and A431 (GI50 = 2.8 µM) cell lines. The most promising of the compounds identified herein were the 4-CF3 substituted 10 and the 3,4-dichloro substituted 13 with excellent activities against MCF-7 and A431 cell lines. The 3,4-dichloro-13 was a 0.56 µM potent inhibitor of MCF-7 cell growth. © 2014 the Partner Organisations.
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Hizartzidis L, Cossar PJ, Robertson MJ, Simone MI, Young KA, McCluskey A, Gordon CP, 'Expanding the utility of flow hydrogenation - A robust protocol restricting hydrodehalogenation', RSC Advances, 4 56743-56748 (2014) [C1]
A commonly observed limitation of conducting hydrogenations under flow chemistry conditions is hydrodehalogenation. In a bid to circumvent this limitation a series of hydrogenatio... [more]
A commonly observed limitation of conducting hydrogenations under flow chemistry conditions is hydrodehalogenation. In a bid to circumvent this limitation a series of hydrogenation catalysts were screened, with 5% Pt/C (sulfided) catalyst identified as an effective catalyst to selectively effect reductive aminations, nitro reduction, and alkene reductions in the presence of halogen atoms. Additionally the optimised protocol cleanly reduced imines in the presence of a furan moiety indicating potential amenability to other labile functionalities.
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Zaleta-Pinet DA, Holland IP, Muñoz-Ochoa M, Murillo-Alvarez JI, Sakoff JA, van Altena IA, McCluskey A, 'Cytotoxic compounds from Laurencia pacifica.', Org Med Chem Lett, 4 8 (2014)
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Stahlschmidt W, Robertson MJ, Robinson PJ, McCluskey A, Haucke V, 'Clathrin Terminal Domain- Ligand Interactions Regulate Sorting of Mannose 6-Phosphate Receptors Mediated by AP-1 and GGA Adaptors*', JOURNAL OF BIOLOGICAL CHEMISTRY, 289 4906-4918 (2014) [C1]
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MacGregor KA, Robertson MJ, Young KA, von Kleist L, Stahlschmidt W, Whiting A, et al., 'Development of 1,8-Naphthalimides as Clathrin Inhibitors', JOURNAL OF MEDICINAL CHEMISTRY, 57 131-143 (2014) [C1]
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Macgregor KA, Abdel-Hamid MK, Odell LR, Chau N, Whiting A, Robinson PJ, McCluskey A, 'Development of quinone analogues as dynamin GTPase inhibitors', European Journal of Medicinal Chemistry, 85 191-206 (2014) [C1]
Virtual screening of the ChemDiversity and ChemBridge compound databases against dynamin I (dynI) GTPase activity identified 2,5-bis-(benzylamino)-1,4- benzoquinone 1 as a 273 ± 1... [more]
Virtual screening of the ChemDiversity and ChemBridge compound databases against dynamin I (dynI) GTPase activity identified 2,5-bis-(benzylamino)-1,4- benzoquinone 1 as a 273 ± 106 µM inhibitor. In silico lead optimization and focused library-led synthesis resulted in the development of four discrete benzoquinone/naphthoquinone based compound libraries comprising 54 compounds in total. Sixteen analogues were more potent than lead 1, with 2,5-bis-(4-hydroxyanilino)-1,4-benzoquinone (45) and 2,5-bis(4-carboxyanilino)- 1,4-benzoquinone (49) the most active with IC50 values of 11.1 ± 3.6 and 10.6 ± 1.6 µM respectively. Molecular modelling suggested a number of hydrogen bonding and hydrophobic interactions were involved in stabilization of 49 within the dynI GTP binding site. Six of the most active inhibitors were evaluated for potential inhibition of clathrin-mediated endocytosis (CME). Quinone 45 was the most effective CME inhibitor with an IC50(CME) of 36 ± 16 µM. © 2014 Published by Elsevier Masson SAS. All rights reserved.
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Booker K, Holdsworth CI, Doherty CM, Hill AJ, Bowyer MC, McCluskey A, 'Ionic liquids as porogens for molecularly imprinted polymers: Propranolol, a model study', Organic and Biomolecular Chemistry, 12 7201-7210 (2014) [C1]
The selectivity and rebinding capacity of molecularly imprinted polymers selective for propranolol (1) using the room temperature ionic liquids [BMIM][BF4], [BMIM][PF6], [HMIM][PF... [more]
The selectivity and rebinding capacity of molecularly imprinted polymers selective for propranolol (1) using the room temperature ionic liquids [BMIM][BF4], [BMIM][PF6], [HMIM][PF6] and [OMIM][PF6] and CHCl3 were examined. The observed IF (imprinting factor) values for MIPBF4, MIPPF6 and MIP CHCl3 were 1.0, 1.98 and 4.64, respectively. The longer chain HMIM and OMIM systems returned lower IF values of 1.1 and 2.3, respectively. MIP PF6 also showed a ~25% binding capacity reduction vs. MIP CHCl3 (5 µmol g-1vs. 7 µmol g-1 respectively). MIPCHCl3 and MIPPF6 differed in terms of BET surface area (306 m2 g-1vs. 185 m2 g -1), pore size (1.10 and 2.19 nm vs. 0.97 and 7.06 nm), the relative number of pores (Type A: 10.4 vs. 7.5%; Type B: 8.5 vs. 3.0%), and surface zeta potential (-37.9 mV vs. -20.3 mV). The MIP specificity for 1 was examined by selective rebinding studies with caffeine (2) and ephedrine (3). MIP PF6 rebound higher quantities of 2 than MIPCHCl3, but this was largely due to non-specific binding. Both MIPCHCl3 and MIP PF6 showed a higher affinity for 3 than for 2. Reduction in the Room Temperature Ionic Liquid (RTIL) porogen volume had little impact on the polymer morphology, but did result in a modest decrease in IF from 2.6 to 2.3 and in the binding capacity (30% to 19%). MIPCHCl3 retained the highest template specificity on rebinding from CHCl3 (IF = 4.6) dropping to IF = 0.6 in MeOH/[BMIM][PF6]. The MIPCHCl3 binding capacity remained constant using CHCl3, CH2Cl2 and MeOH (46-52%), dropped to 6% on addition of [BMIM][PF6] and increased to 83% in H2O (but at the expense of specificity with IFH2O = 1.4). MIPPF6 rebinding from MeOH saw an increase in specific rebinding to IF = 4.9 and also an increase in binding capacity to 48% when rebinding 1 from MeOH and to 42% and 45% with H2O and CH2Cl2, respectively, although in the latter case the increased capacity was at the cost of specificity with IFCH2Cl2 = 1.2. Overall the MIPPF6 capacity and specificity were enhanced on addition of MeOH. This journal is © the Partner Organisations 2014.
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Zayas H, Holdsworth CI, Bowyer MC, McCluskey A, 'Evaluation of 4-substituted styrenes as functional monomers for the synthesis of theophylline-specific molecularly imprinted polymers.', Org Biomol Chem, 12 6994-7003 (2014) [C1]
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Cleland D, Olsson GD, Karlsson BCG, Nicholls IA, McCluskey A, 'Molecular dynamics approaches to the design and synthesis of PCB targeting molecularly imprinted polymers: interference to monomer-template interactions in imprinting of 1,2,3-trichlorobenzene', ORGANIC & BIOMOLECULAR CHEMISTRY, 12 844-853 (2014) [C1]
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Trinh TN, Hizartzidis L, Lin AJ, Harman DG, McCluskey A, Gordon CP, 'An efficient continuous flow approach to furnish furan-based biaryls', Organic & Biomolecular Chemistry, 12 9562-9571 (2014) [C1]
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Gordon CP, Hizartzidis L, Tarleton M, Sakoff JA, Gilbert J, Campbell BE, et al., 'Discovery of acrylonitrile-based small molecules active against Haemonchus contortus', MEDCHEMCOMM, 5 159-164 (2014) [C1]
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Trinh TN, McLaughlin EA, Gordon CP, McCluskey A, 'Hedgehog signalling pathway inhibitors as cancer suppressing agents', MedChemComm, 5 117-133 (2014) [C1]
The Hedgehog (Hh) signalling pathway plays a pivotal role in the spatial and temporal regulation of cell proliferation and differentiation. By controlling the correct maturation o... [more]
The Hedgehog (Hh) signalling pathway plays a pivotal role in the spatial and temporal regulation of cell proliferation and differentiation. By controlling the correct maturation of developing tissues and ensuring attainment of the correct size, position and the presence of fully functioning cellular structures, the Hh plays a pivotal role in development. Conversely aberrant Hh signalling is involved in Gorlin syndrome, basal cell carcinoma (the most common cancer in the world), and more than one third of all human medulloblastoma cases. In all of these cases, it is believed that deregulated Hh signalling leads to increased cell proliferation and tumour formation. Inhibition of the Hedgehog signalling pathway, is a recently validated anti-cancer drug target, with vismodegib (Erivedge¿), approved by the U.S. Food and Drug Administration for the treatment of adult basal cell carcinoma. In this perspective we outline the current state of Hh pathway inhibitors with a particular focus on potential limitations of upstream Hh pathway inhibition in relation to resistance mutations and crosstalk pathways. Together, these limitations indicate that inhibition of downstream components, specifically the Gli family of transcription factors, may represent a next generation approach to suppress tumours associated with aberrant Hh pathway signalling. © 2014 The Royal Society of Chemistry.
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Dyson L, Young KA, McCluskey A, Wright AD, Sakoff JA, 'Synthesis and anticancer activity of focused compound libraries from the natural product lead, oroidin', Bioorganic and Medicinal Chemistry, 22 1690-1699 (2014) [C1]
Oroidin (1), (E)-N-(3-(2-amino-1H-imidazol-4-yl)allyl)-4,5-dibromo-1H- pyrrole-2-carboxamide, is a pyrrole alkaloid isolated from the marine sponge Agelas oroides. Routine screeni... [more]
Oroidin (1), (E)-N-(3-(2-amino-1H-imidazol-4-yl)allyl)-4,5-dibromo-1H- pyrrole-2-carboxamide, is a pyrrole alkaloid isolated from the marine sponge Agelas oroides. Routine screening in a panel of twelve cancer cell lines revealed 1 to be poorly cytotoxic with the 50% growth inhibition concentration (GI) of 42 µM in MCF-7 (breast) cells and 24 µM in A2780 (ovarian) cells and >50 µM in all other cell lines tested. The development of eight focused libraries comprising thirty compounds total identified N-(biphenyl-4-ylmethyl)-1H-pyrrole-2-carboxamide (4l), N-benzyl-4,5-dibromo-1H- pyrrole-2-carboxamide (5a) and N-(biphenyl-4-ylmethyl)-4,5-dibromo-1H-pyrrole-2- carboxamide (5l) as potent inhibitors of cell growth in our panel of cell lines. Of these compounds GI values of <5 µM were observed with 4l against HT29 (colon) and SW480 (colon); 5a against HT29; and 5l against HT29, SW480, MCF-7, A431 (skin), Du145 (prostate), BE2-C (neuroblastoma) and MIA (pancreas) cell lines. As a cancer class, colon cancer appears to be more sensitive to the oroidin series of compounds, with analogue 5l being the most active. © 2014 Elsevier Ltd. All rights reserved.
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Robertson MJ, Deane FM, Stahlschmidt W, Von Kleist L, Haucke V, Robinson PJ, McCluskey A, 'Synthesis of the Pitstop family of clathrin inhibitors', Nature Protocols, 9 1592-1606 (2014) [C1]
This protocol describes the synthesis of two classes of clathrin inhibitors, Pitstop 1 and Pitstop 2, along with two inactive analogs that can be used as negative controls (Pitsto... [more]
This protocol describes the synthesis of two classes of clathrin inhibitors, Pitstop 1 and Pitstop 2, along with two inactive analogs that can be used as negative controls (Pitstop inactive controls, Pitnot-2 and Pitnot-2-100). Pitstop-induced inhibition of clathrin TD function acutely interferes with clathrin-mediated endocytosis (CME), synaptic vesicle recycling and cellular entry of HIV, whereas clathrin-independent internalization pathways and secretory traffic proceed unperturbed; these reagents can, therefore, be used to investigate clathrin function, and they have potential pharmacological applications. Pitstop 1 is synthesized in two steps: sulfonation of 1,8-naphthalic anhydride and subsequent reaction with 4-amino(methyl)aniline. Pitnot-1 results from the reaction of 4-amino(methyl)aniline with commercially available 4-sulfo-1,8-naphthalic anhydride potassium salt. Reaction of 1-naphthalene sulfonyl chloride with pseudothiohydantoin followed by condensation with 4-bromobenzaldehyde yields Pitstop 2. The synthesis of the inactive control commences with the condensation of 4-bromobenzaldehyde with the rhodanine core. Thioketone methylation and displacement with 1-napthylamine affords the target compound. Although Pitstop 1-series compounds are not cell permeable, they can be used in biochemical assays or be introduced into cells via microinjection. The Pitstop 2-series compounds are cell permeable. The synthesis of these compounds does not require specialist equipment and can be completed in 3-4 d. Microwave irradiation can be used to reduce the synthesis time. The synthesis of the Pitstop 2 family is easily adaptable to enable the synthesis of related compounds such as Pitstop 2-100 and Pitnot-2-100. The procedures are also simple, efficient and amenable to scale-up, enabling cost-effective in-house synthesis for users of these inhibitor classes.
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Robertson MJ, Deane FM, Robinson PJ, McCluskey A, 'Synthesis of Dynole 34-2, Dynole 2-24 and Dyngo 4a for investigating dynamin GTPase', Nature Protocols, 9 851-870 (2014) [C1]
Dynamin is a large GTPase with roles in membrane fission during clathrin-mediated endocytosis, in actin dynamics and in cytokinesis. Defects in dynamin have been linked to human d... [more]
Dynamin is a large GTPase with roles in membrane fission during clathrin-mediated endocytosis, in actin dynamics and in cytokinesis. Defects in dynamin have been linked to human diseases. The synthesis of a dynamin modulator toolkit comprising two different inhibitor classes is described. The first series comprises Dynole 34-2, Dynole 2-24 and the inactive control Dynole 31-2. The Dynole compounds act on the dynamin G domain, are not GTP competitive and can be synthesized in 2-3 d. Knoevenagel condensation of 1-(3-(dimethylamino) propyl)-1H-indole-3-carbaldehyde (1) with cyanoamides (2 and 3) affords Dynole 31-2 and Dynole 34-2, respectively. Reductive amination of 1 with decylamine gives Dynole 2-24. The second series acts at an allosteric site in the G domain of dynamin and comprises Dyngo 4a and Dyngo Ø (inactive control). Both are synthesized in an overnight reaction via condensation of 3-hydroxy-2-naphthoic hydrazide with 2,4,5-trihydroxybenzaldehyde to afford Dyngo 4a, or with benzaldehyde to afford Dyngo Ø. © 2014 Nature America, Inc. All rights reserved.
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2014 |
Sobinoff AP, Sutherland JM, Beckett EL, Stanger SJ, Johnson R, Jarnicki AG, et al., 'Damaging legacy: maternal cigarette smoking has long-term consequences for male offspring fertility.', Hum Reprod, 29 2719-2735 (2014) [C1]
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2013 |
Harper CB, Popoff MR, McCluskey A, Robinson PJ, Meunier FA, 'Targeting membrane trafficking in infection prophylaxis: Dynamin inhibitors', Trends in Cell Biology, 23 90-101 (2013) [C1]
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2013 |
Stehn JR, Haass NK, Bonello T, Desouza M, Kottyan G, Treutlein H, et al., 'A Novel Class of Anticancer Compounds Targets the Actin Cytoskeleton in Tumor Cells', CANCER RESEARCH, 73 5169-5182 (2013) [C1]
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2013 |
Gordon CP, Venn-Brown B, Robertson MJ, Young KA, Chau N, Mariana A, et al., 'Development of Second-Generation Indole-Based Dynamin GTPase Inhibitors', Journal of Medicinal Chemistry, 56 46-59 (2013) [C1]
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2013 |
Sobinoff AP, Beckett EL, Jarnicki AG, Sutherland JM, McCluskey A, Hansbro PM, McLaughlin EA, 'Scrambled and fried: Cigarette smoke exposure causes antral follicle destruction and oocyte dysfunction through oxidative stress', TOXICOLOGY AND APPLIED PHARMACOLOGY, 271 156-167 (2013) [C1]
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2013 |
Tarleton M, Dyson L, Gilbert J, Sakoff JA, McCluskey A, 'Focused library development of 2-phenylacrylamides as broad spectrum cytotoxic agents', BIOORGANIC & MEDICINAL CHEMISTRY, 21 333-347 (2013) [C1]
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2013 |
McCluskey A, Daniel JA, Hadzic G, Ngoc C, Clayton EL, Mariana A, et al., 'Building a Better Dynasore: The Dyngo Compounds Potently Inhibit Dynamin and Endocytosis', TRAFFIC, 14 1272-1289 (2013)
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McCluskey A, Daniel JA, Hadzic G, Chau N, Clayton EL, Mariana A, et al., 'Building a Better Dynasore: The Dyngo Compounds Potently Inhibit Dynamin and Endocytosis', Traffic, 14 1272-1289 (2013) [C1]
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2013 |
Byrne N, Barrow C, Mccluskey A, 'SOLVENT INDUCED CHANGES IN THE CONFORMATIONAL STATE OF beta-LACTOGLOBULIN AND THE INFLUENCE OF PROTIC IONIC LIQUIDS', JOURNAL OF MOLECULAR AND ENGINEERING MATERIALS, 1 (2013)
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2013 |
Smith CM, Haucke V, McCluskey A, Robinson PJ, Chircop M, 'Inhibition of clathrin by pitstop 2 activates the spindle assembly checkpoint and induces cell death in dividing HeLa cancer cells', MOLECULAR CANCER, 12 (2013) [C1]
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2013 |
Cleland D, McCluskey A, 'An extreme vertices mixture design approach to the optimisation of 1,2,3-trichlorobenzene specific molecularly imprinted polymers', ORGANIC & BIOMOLECULAR CHEMISTRY, 11 4672-4679 (2013) [C1]
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2013 |
Deane FM, O'Sullivan EC, Maguire AR, Gilbert J, Sakoff JA, McCluskey A, McCarthy FO, 'Synthesis and evaluation of novel ellipticines as potential anti-cancer agents', Organic & Biomolecular Chemistry, 11 1334-1344 (2013) [C1]
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2013 |
Brisbane C, McCluskey A, Bowyer M, Holdsworth CI, 'Molecularly imprinted films of acrylonitrile/methyl methacrylate/acrylic acid terpolymers: influence of methyl methacrylate in the binding performance of L-ephedrine imprinted films', Organic & Biomolecular Chemistry, 11 2872-2884 (2013) [C1]
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2013 |
Cleland D, McCluskey A, 'The use of effective fragment potentials in the design and synthesis of molecularly imprinted polymers for the group recognition of PCBs', Organic and Biomolecular Chemistry, 11 4646-4656 (2013) [C1]
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2013 |
Zhang J, Luo S-X, McCluskey A, Lawrance GA, 'Metal-Templated Macrocycle Synthesis in an Ionic Liquid: A Comparison With Reaction in Protic Solvents', Synthesis and Reactivity in Inorganic, Metal Organic, and Nano Metal Chemistry, 43 1-5 (2013) [C1]
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2013 |
McGeachie AB, Odell LR, Quan A, Daniel JA, Chau N, Hill TA, et al., 'Pyrimidyn compounds: Dual-action small molecule pyrimidine-based dynamin inhibitors', ACS Chemical Biology, 8 1507-1518 (2013) [C1]
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2012 |
Turner NW, Holdsworth CI, McCluskey A, Bowyer MC, 'N-2-propenyl-(5-dimethylamino)-1-naphthalene sulfonamide, a novel fluorescent monomer for the molecularly imprinted polymer-based detection of 2,4-dinitrotoluene in the gas phase', Australian Journal of Chemistry, 65 1405-1412 (2012) [C1]
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2012 |
Reid AT, Lord T, Stanger SJ, Roman SD, McCluskey A, Robinson PJ, et al., 'Dynamin regulates specific membrane fusion events necessary for acrosomal exocytosis in mouse spermatozoa', Journal of Biological Chemistry, 287 37659-37672 (2012) [C1]
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2012 |
Robinson K, McCluskey A, Attalla MI, 'The effect molecular structural variations has on the CO
This chapter details the novel application of in-situ Attenuated Reflectance Fourier Transform Infrared (ATR FT-IR) spectroscopy to investigate the effect molecular structural var... [more]
This chapter details the novel application of in-situ Attenuated Reflectance Fourier Transform Infrared (ATR FT-IR) spectroscopy to investigate the effect molecular structural variation has on the CO2 absorption characteristics of heterocyclic amines. The reaction between CO2 and a subset of structurally variant amines were analyzed including piperidine, as well as commercially available functionalized piperidine derivatives, for example, those with methyl-, hydroxyl- and hydroxyalkyl- substituents. This new technique uses an ATR probe optically coupled to an FT-IR spectrometer to monitor the reaction species evolving in solution as CO2 is being absorbed into solution. The effect of molecular structural variations on CO 2 absorption was then assessed in relation to the IR identifiable ionic reaction products, CO2 absorption capacity and the mass-transfer coefficient at zero loading. © 2012 American Chemical Society.
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2012 |
Tarleton MJ, Gilbert J, Sakoff JA, McCluskey A, 'Synthesis and anticancer activity of a series of norcantharidin analogues', European Journal of Medicinal Chemistry, 54 573-581 (2012) [C1]
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2012 |
Tarleton MJ, Gilbert J, Sakoff JA, McCluskey A, 'Cytotoxic 2-phenyacrylnitriles, the importance of the cyanide moiety and discovery of potent broad spectrum cytotoxic agents', European Journal of Medicinal Chemistry, 57 65-73 (2012) [C1]
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2012 |
Daniel JA, Malladi CS, Kettle E, McCluskey A, Robinson PJ, 'Analysis of synaptic vesicle endocytosis in synaptosomes by high-content screening', Nature Protocols, 7 1439-1455 (2012) [C1]
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2012 |
Segueira VB, Stehn JR, Haass N, Bonello T, Guven K, Desouza M, et al., 'Improving the specificity of drugs which target the actin cytoskeleton for cancer therapy', CANCER RESEARCH, 72 (2012)
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Stehn JR, Haass NK, Desouza M, Kottyan G, Treutlein H, Zeng J, et al., 'Developing chemotherapeutics which selectively disable the actin cytoskeleton of tumor cells', CANCER RESEARCH, 72 (2012)
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Tarleton MJ, Bernhardt PV, McCluskey A, 'Crystal structures of (3R,3aR,4S,7R,7aS)-3-(Allyloxy)hexahydro-4,7-epoxyisobenzofuran-1(3H)-on e and (3S,3aR,4S,7R,7aS)-3-((E)-But-2-en-1-yloxy)hexahydro-4,7-epoxyisobenzofu ran-1(3H)-one: Confirmation of NMR predicted stereocentre geometry', Journal of Chemical Crystallography, 42 639-644 (2012) [C1]
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Robinson KM, McCluskey A, Attalla MI, 'An ATR-FTIR study on the effect of molecular structural variations on the CO2 absorption characteristics of Heterocyclic Amines, Part II', Chemphyschem, 13 2331-2341 (2012) [C1]
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Nguyen TH, Maucort G, Sullivan RKP, Schenning M, Lavidis NA, McCluskey A, et al., 'Actin- and dynamin-dependent maturation of bulk endocytosis restores neurotransmission following synaptic depletion', PLoS One, 7 (2012) [C1]
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2012 |
Robertson MJ, Hadzic G, Ambrus JI, Pome DY, Hyde EDE, Whiting A, et al., 'The Rhodadyns, a new class of small molecule inhibitors of Dynamin GTPase Activity', ACS Medicinal Chemistry Letters, 3 352-356 (2012) [C1]
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2011 |
Wright AD, McCluskey A, Robertson MJ, Macgregor KA, Gordon CP, Guenther J, 'Anti-malarial, anti-algal, anti-tubercular, anti-bacterial, anti-photosynthetic, and anti-fouling activity of diterpene and diterpene isonitriles from the tropical marine sponge Cymbastela hooperi', Organic and Biomolecular Chemistry, 9 400-407 (2011) [C1]
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2011 |
Gordon CP, Young KA, Hizartzidis L, Deane FM, McCluskey A, 'Investigation of the one-pot synthesis of quinolin-2-(1H)-ones and the discovery of a variation of the three-component Ugi reaction', Organic and Biomolecular Chemistry, 9 1419-1428 (2011) [C1]
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2011 |
Chircop M, Perera S, Mariana A, Lau H, Ma MPC, Gilbert J, et al., 'Inhibition of dynamin by dynole 34-2 induces cell death following cytokinesis failure in cancer cells', Molecular Cancer Therapeutics, 10 1553-1562 (2011) [C1]
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2011 |
Tarleton MJ, Young KA, Unicomb E, McCluskey SN, Robertson MJ, Gordon CP, McCluskey A, 'A flow chemistry approach to norcantharidin analogues', Letters in Drug Design and Discovery, 8 568-574 (2011) [C1]
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2011 |
Tarleton MJ, Gilbert J, Robertson MJ, McCluskey A, Sakoff JA, 'Library synthesis and cytotoxicity of a family of 2-phenylacrylonitriles and discovery of an estrogen dependent breast cancer lead compound', MedChemComm, 2 31-37 (2011) [C1]
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2011 |
Robinson KM, McCluskey A, Attalla M, 'The effect molecular structural variations has on the CO2 absorption characteristics of heterocyclic amines', Energy Procedia, 4 224-231 (2011) [C1]
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2011 |
Harper CB, Martin S, Nguyen TH, Daniels SJ, Lavidis NA, Popoff MR, et al., 'Dynamin inhibition blocks botulinum neurotoxin type A endocytosis in neurons and delays botulism', Journal of Biological Chemistry, 286 35966-35976 (2011) [C1]
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2011 |
Gordon CP, Young KA, Robertson MJ, Hill TA, McCluskey A, 'An Ugi-intramolecular Diels-Alder route to highly substituted tetrahydroepoxyisoindole carboxamides', Tetrahedron, 67 554-561 (2011) [C1]
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2011 |
Macgregor KA, McCluskey A, 'Ionic liquids accelerate access to N-substituted-1,8-naphthalimides', Tetrahedron Letters, 52 767-769 (2011) [C1]
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2011 |
Tarleton MJ, McCluskey A, 'A flow chemistry route to 2-phenyl-3-(1H-pyrrol-2-yl)propan-1-amines', Tetrahedron Letters, 52 1583-1586 (2011) [C1]
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Nova |
2011 |
Von Kleist L, Stahlschmidt W, Bulut H, Gromova K, Puchkov D, Robertson MJ, et al., 'Role of the clathrin terminal domain in regulating coated pit dynamics revealed by small molecule inhibition', Cell, 146 471-484 (2011) [C1]
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2011 |
Campbell BE, Hofmann A, McCluskey A, Gasser RB, 'Serine/threonine phosphatases in socioeconomically important parasitic nematodes - Prospects as novel drug targets?', Biotechnology Advances, 29 28-39 (2011) [C1]
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Nova |
2011 |
Campbell BE, Tarleton MJ, Gordon CP, Sakoff JA, Gilbert J, McCluskey A, Gasser RB, 'Norcantharidin analogues with nematocidal activity in Haemonchus contortus', Bioorganic and Medicinal Chemistry Letters, 21 3277-3281 (2011) [C1]
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Nova |
2011 |
Robertson MJ, Gordon CP, Gilbert J, McCluskey A, Sakoff JA, 'Norcantharimide analogues possessing terminal phosphate esters and their anti-cancer activity', Bioorganic & Medicinal Chemistry, 19 5734-5741 (2011) [C1]
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Nova |
2011 |
Von Kleist L, Stahlschmidt W, Bulut H, Gromova K, Puchkov D, Robertson MJ, et al., 'Erratum: Role of the clathrin terminal domain in regulating coated pit dynamics revealed by small molecule inhibition (Cell (2011)146 (471-484))', Cell, 146 841 (2011)
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2011 |
Robinson KM, McCluskey A, Attalla MI, 'An FTIR spectroscopic study on the effect of molecular structural variations on the CO2 absorption characteristics of heterocyclic amines', ChemPhysChem, 12 1088-1099 (2011) [C1]
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Nova |
2010 |
Joshi S, Perera S, Gilbert J, Smith CM, Mariana A, Gordon CP, et al., 'The Dynamin inhibitors MiTMAB and OcTMAB induce Cytokinesis failure and inhibit cell proliferation in human cancer cells', Molecular Cancer Therapeutics, 9 1995-2006 (2010) [C1]
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Nova |
2010 |
Howes MT, Kirkham M, Riches J, Cortese K, Walser PJ, Simpson F, et al., 'Clathrin-independent carriers form a high capacity endocytic sorting system at the leading edge of migrating cells', Journal of Cell Biology, 190 675-691 (2010) [C1]
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Nova |
2010 |
Hill TA, Mariana A, Gordon CP, Odell L, Robertson MJ, McGeachie AB, et al., 'Iminochromene inhibitors of Dynamins I and II GTPase activity and Endocytosis', Journal of Medicinal Chemistry, 53 4094-4102 (2010) [C1]
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Nova |
2010 |
Odell L, Howan D, Gordon CP, Robertson MJ, Chau N, Mariana A, et al., 'The Pthaladyns: GTP competitive inhibitors of Dynamin I and II GTPase derived from virtual screening', Journal of Medicinal Chemistry, 53 5267-5280 (2010) [C1]
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Nova |
2010 |
Thaqi A, Scott JL, Gilbert J, Sakoff JA, McCluskey A, 'Synthesis and biological activity of Delta-5,6-norcantharimides: Importance of the 5,6-bridge', European Journal of Medicinal Chemistry, 45 1717-1723 (2010) [C1]
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Nova |
2010 |
Bajsa J, McCluskey A, Gordon CP, Stewart SG, Hill TA, Sahu R, et al., 'The antiplasmodial activity of norcantharidin analogs', Bioorganic & Medicinal Chemistry Letters, 20 6688-6695 (2010) [C1]
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Nova |
2010 |
Turner NW, Holdsworth CI, Donne SW, McCluskey A, Bowyer MC, 'Microwave induced MIP synthesis: comparative analysis of thermal and microwave induced polymerisation of caffeine imprinted polymers', New Journal of Chemistry, 34 686-692 (2010) [C1]
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Nova |
2010 |
Chircop M, Malladi CS, Lian AT, Page SL, Zavortink M, Gordon CP, et al., 'Calcineurin activity is required for the completion of cytokinesis', Cellular and Molecular Life Sciences, 67 3725-3737 (2010) [C1]
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Nova |
2010 |
Gordon CP, Byrne N, McCluskey A, 'A facile, protic ionic liquid route to N-substituted 5-hydroxy-4-methyl-3-oxoisoindoline-1-carboxamides and N-substituted 3-oxoisoindoline-4-carboxylic acids', Green Chemistry, 12 1000-1006 (2010) [C1]
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Nova |
2009 |
Sauer B, Gilbert J, Sakoff JA, McCluskey A, 'Synthesis of 4-substituted-3-hydroxy-5-oxo-10-oxa-4-azatricyclo[5.2.1]dec-3-yl Acetic Acid Ethyl Esters as Norcantharidin Analogues', Letters in Drug Design & Discovery, 6 1-7 (2009) [C1]
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Nova |
2009 |
Turner NW, Holmes NP, Brisbane CE, McGeachie AB, Bowyer MC, McCluskey A, Holdsworth CI, 'Effect of template on the formation of phase-inversed molecularly imprinted polymer thin films: An assessment', Soft Matter, 5 3663-3671 (2009) [C1]
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Nova |
2009 |
Odell L, Chau N, Mariana A, Graham ME, Robinson PJ, McCluskey A, 'Azido and diazarinyl analogues of bis-tyrphostin as asymmetrical inhibitors of dynamin GTPase', Chemmedchem, 4 1182-1188 (2009) [C1]
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Nova |
2009 |
Hill TA, Gordon CP, McGeachie AB, Venn-Brown B, Odell L, Chau N, et al., 'Inhibition of dynamin mediated endocytosis by the dynoles-synthesis and functional activity of a family of indoles', Journal of Medicinal Chemistry, 52 3762-3773 (2009) [C1]
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Nova |
2009 |
Zayas HA, Bowyer MC, Gordon CP, Holdsworth CI, McCluskey A, 'Synthesis of biaryl-styrene monomers by microwave-assisted Suzuki coupling', Tetrahedron Letters, 50 5894-5895 (2009) [C1]
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Nova |
2009 |
Holland IP, McCluskey A, Sakoff JA, Gilbert J, Chau N, Robinson PJ, et al., 'Steroids from an Australian Sponge Psammoclema sp', Journal of Natural Products, 72 102-106 (2009) [C1]
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Nova |
2009 |
Whitehead JA, Zhang J, McCluskey A, Lawrance GA, 'Comparative leaching of a sulfidic gold ore in ionic liquid and aqueous acid with thiourea and halides using Fe(III) or HSO5- oxidant', Hydrometallurgy, 98 276-280 (2009) [C1]
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Nova |
2009 |
Odell LR, Skopec J, McCluskey A, 'Isolation and identification of unique marker compounds from the Tasmanian poppy Papaver somniferum N. Implications for the identification of illicit heroin of Tasmanian origin (vol 175, pg 202, 2008)', FORENSIC SCIENCE INTERNATIONAL, 183 105-106 (2009) [C3]
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2009 |
Mann JP, McCluskey A, Atkin R, 'Activity and thermal stability of lysozyme in alkylammonium formate ionic liquids: Influence of cation modification', Green Chemistry, 11 785-792 (2009) [C1]
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Nova |
2008 |
Zhang J, Lawrance GA, Chau N, Robinson PJ, McCluskey A, 'From Spanish fly to room-temperature ionic liquids (RTILs): Synthesis, thermal stability and inhibition of dynamin 1 GTPase by a novel class of RTILs', New Journal of Chemistry, 32 28-36 (2008) [C1]
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Nova |
2008 |
Hill TA, Stewart SG, Gordon CP, Ackland SR, Gilbert J, Sauer B, et al., 'Norcantharidin analogues: Synthesis, anticancer activity and protein phosphatase 1 and 2A inhibition', ChemMedChem, 3 1878-1892 (2008) [C1]
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2008 |
McCluskey A, Wentrup C, '2-pyridyinitrene from tetrazolo[1,5-a]pyridine and Pyrido[2,3-a][1,2,4]oxadiazol-2-one', JOURNAL OF ORGANIC CHEMISTRY, 73 6265-6267 (2008) [C1]
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2008 |
Thaqi A, McCluskey A, Scott JL, 'A mild Boc deprotection and the importance of a free carboxylate', Tetrahedron Letters, 49 6962-6964 (2008) [C1]
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Nova |
2008 |
Odell L, Skopec J, McCluskey A, 'Isolation and identification of unique marker compounds from the Tasmanian poppy Papaver somniferum N. Implications for the identification of illicit heroin of Tasmanian origin', Forensic Science International, 175 202-208 (2008) [C1]
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Nova |
2007 |
Whitehead JA, Zhang J, Pereira N, McCluskey A, Lawrance GA, 'Application of 1-alkyl-3-methyl-imidazolium ionic liquids in the oxidative leaching of sulphidic copper, gold and silver ores', Hydrometallurgy, 88 109-120 (2007) [C1]
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2007 |
Qi Y, Evans I, McCluskey A, 'New impurity profiles of recent Australian imported 'ice': Methamphetamine impurity profiling and the identification of (pseudo)ephedrine and Leuckart specific marker compounds', Forensic Science International, 169 173-180 (2007) [C1]
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2007 |
McCluskey A, Holdsworth CI, Bowyer MC, 'Molecularly imprinted polymers (MIPs): sensing, an explosive new opportunity?', Organic & Biomolecular Chemistry, 5 3233-3244 (2007) [C1]
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Nova |
2007 |
Hill TA, Stewart SG, Sauer B, Gilbert J, Ackland S, Sakoff JA, McCluskey A, 'Heterocyclic substituted cantharidin and norcantharidin analogues-synthesis, protein phosphatase (1 and 2A) inhibition, and anti-cancer activity', Bioorganic and Medicinal Chemistry Letters, 17 3392-3397 (2007) [C1]
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Nova |
2007 |
Hill TA, Stewart SG, Ackland S, Gilbert J, Sauer B, Sakoff JA, McCluskey A, 'Norcantharimides, synthesis and anticancer activity: Synthesis of new norcantharidin analogues and their anticancer evaluation', Bioorganic and Medicinal Chemistry, 15 6126-6134 (2007) [C1]
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Nova |
2007 |
Stewart SG, Hill TA, Gilbert J, Ackland S, Sakoff JA, McCluskey A, 'Synthesis and biological evaluation of norcantharidin analogues: Towards PP1 selectivity', Bioorganic and Medicinal Chemistry, 15 7301-7310 (2007) [C1]
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2007 |
Odell L, McCluskey A, Failes TW, Tiekink ERT, 'Crystal and molecular structures of benzyl-(2-chloro-6-methylpyrimidin-4-yl)amine and benzyl-(4-chloro-6-methylpyrimidin-2-yl)amine: Confirmation of computationally predicted restricted rotation', Journal of Chemical Crystallography, 37 817-824 (2007) [C1]
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2007 |
Hemley CF, McCluskey A, Keller PA, 'Corticotropin releasing hormone - A GPCR drug target', Current Drug Targets, 8 105-115 (2007) [C1]
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2007 |
Booker KM, Bowyer MC, Lennard CJ, Holdsworth CI, McCluskey A, 'Molecularly imprinted polymers and room temperature ionic liquids: Impact of template on polymer morphology', Australian Journal of Chemistry, 60 51-56 (2007) [C1]
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Nova |
2007 |
Quan A, McGeachie AB, Keating DJ, Van Dam EM, Rusak J, Chau N, et al., 'Myristyl trimethyl ammonium bromide and octadecyl trimethyl ammonium bromide are surface-active small molecule dynamin inhibitors that block endocytosis mediated by dynamin I or dynamin II', Molecular Pharmacology, 72 1425-1439 (2007) [C1]
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2006 |
Keller PA, McCluskey A, Morgan J, O'Connor SMJ, 'The role of the HPA axis in psychiatric disorders and CRF antagonists as potential treatments', Archiv Der Pharmazie, 339 346-355 (2006) [C1]
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2006 |
Odell L, Skopec J, McCluskey A, 'A `cold synthesis' of heroin and implications in heroin signature analysis: Utility of trifluoroacetic/acetic anhydride in the acetylation of morphine', Forensic Science International, 164 221-229 (2006) [C1]
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2006 |
Qi Y, Evans ID, McCluskey A, 'Australian Federal Police seizures of illicit crystalline methamphetamine (`ice') 1998-2002: Impurity analysis', Forensic Science International, 164 201-210 (2006) [C1]
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2006 |
Booker KM, Bowyer MC, Holdsworth CI, McCluskey A, 'Efficient preparation and improved sensitivity of molecularly imprinted polymers using room temperature ionic liquids', Chemical Communications, 1730-1732 (2006) [C1]
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Nova |
2006 |
Griffith R, Brown MN, McCluskey A, Ashman LK, 'Small molecule inhibitors of protein kinases in cancer - How to overcome resistance', Mini-Reviews in Medicinal Chemistry, 6 1101-1110 (2006) [C1]
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Nova |
2006 |
Whitehead JA, Lawrence GA, Owen MP, McCluskey A, 'A new route to precious metal recovery and subsequent electrodeposition using ionic liquids', Proceedings - Electrochemical Society, PV 2004-24 901-910 (2006)
Gold extraction from complex sulfidic ore occurs in l-butyl-3- methylimidazolium hydrogen sulfate (bmim+HS4-) ionic liquid in the presence of thiourea in a facile, high yielding (... [more]
Gold extraction from complex sulfidic ore occurs in l-butyl-3- methylimidazolium hydrogen sulfate (bmim+HS4-) ionic liquid in the presence of thiourea in a facile, high yielding (86%), recyclable process. Silver recovery from the ore is also enhanced. Gold recovery from ionic liquid / water environments directly by electrodeposition is described. Changing from aqueous acid to ionic liquid solvent causes a growth mode transition to dendritic growth patterns for deposited gold.
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2006 |
Schwarz LJ, Bowyer MC, Holdsworth CI, McCluskey A, 'Synthesis and evaluation of a molecularly imprinted polymer selective to 2,4,6-trichloroanisole', Australian Journal of Chemistry, 59 129-134 (2006) [C1]
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2005 |
Holdsworth CI, Bowyer MC, Lennard C, McCluskey A, 'Formulation of cocaine-imprinted polymers utilizing molecular modelling and NMR analysis', Australian Journal of Chemistry, 58 315-320 (2005) [C1]
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Nova |
2005 |
Hill TA, Odell L, Edwards JK, Graham ME, McGeachie AB, Rusak J, et al., 'Small molecule inhibitors of dynamin I GTPase activity: Development of dimeric tyrphostins', Journal of Medicinal Chemistry, 48 7781-7788 (2005) [C1]
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Nova |
2005 |
McCluskey A, Leitch SK, Garner JA, Caden CE, Hill TA, Odell L, Stewart SG, 'BiCl3-mediated opening of epoxides, a facile route to chlorohydrins or amino alcohols: one reagent, two paths', Tetrahedron Letters, 46 8229-8232 (2005) [C1]
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Nova |
2005 |
Leitch SK, Addison-Jones J, McCluskey A, 'Regioselective N- and C2-electrophilic substitution of 3-substituted indoles (short communication)', Tetrahedron Letters, 46 2915-2918 (2005) [C1]
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Nova |
2005 |
Hill TA, Sakoff JA, Robinson PJ, McCluskey A, 'Parallel solution-phase synthesis of targeted tyrphostin libraries with anticancer activity', Australian Journal of Chemistry, 58 94-103 (2005) [C1]
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2004 |
Whitehead JA, Lawrance GA, McCluskey A, 'Analysis of Gold in Solutions Containing Ionic Liquids by Inductively Coupled Plasma Atomic Emission Spectometry', Australian Journal of Chemistry, 57 151-155 (2004) [C1]
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Nova |
2004 |
Schwarz LJ, Holdsworth CI, McCluskey A, Bowyer MC, 'Synthesis and Evaluation of a Molecularly Imprinted Polymer Selective to 2,4,6-Trichlorophenol', Australian Journal of Chemistry, 57 759-764 (2004) [C1]
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Nova |
2004 |
Garner JA, Keller PA, McCluskey A, 'Corticotrophin Releasing Hormone: Chemistry and Recent Developments', Australian Journal of Chemistry, 57 393-407 (2004) [C1]
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2004 |
Garner JA, Hill TA, Odell L, Keller P, Morgan J, McCluskey A, 'Identification of Aminopyrimidine Regioisomers via Line Broadening Effects in 1H and 13C NMR Spectroscopy', Australian Journal of Chemistry, 57 1079-1083 (2004) [C1]
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Nova |
2004 |
Bowyer MC, Gordon CM, Leitch SK, McCluskey A, Ritchie C, 'Indium-Mediated Addition of 4-Bromocrotonic Acid to Aldehydes and Ketones - A Simple, High Yielding Route to Alpha-Allyl-Beta-Hydroxy Carboxylic Acids', Australian Journal of Chemistry: an international journal for chemical science, 57 135-137 (2004) [C1]
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2004 |
Sakoff JA, Howitt IJ, Ackland S, McCluskey A, 'Serine/threonine protein phosphatase inhibition enhances the effect of thymidylate synthase inhibition', Cancer Chemotherapy and Pharmacology, 53 225-232 (2004) [C1]
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Nova |
2004 |
Hart ME, Chamberlin AR, Walkom CC, Sakoff JA, McCluskey A, 'Modified norcantharidins: synthesis, protein phosphatases 1 and 2A inhibition, and anticancer activity', Bioorganic & Medicinal Chemistry Letters, 14 1969-1973 (2004) [C1]
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Nova |
2004 |
Hill TA, Odell L, Quan A, Abagyan R, Ferguson GN, Robinson PJ, McCluskey A, 'Long chain amines and long chain ammonium salts as novel inhibitors of dynamin GTPase activity', Bioorganic & Medicinal Chemistry Letters, 14 3275-3278 (2004) [C1]
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Nova |
2004 |
Sakoff JA, McCluskey A, 'Protein Phosphatase Inhibition: Structure Based Design. Towards New Therapeutic Agents', Current Pharmaceutical Design, 10 1139-1159 (2004) [C1]
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2004 |
McCluskey A, Bowyer MC, 'Synthetic antibodies and the Australian wine industry: A Hunter Valley solution to cork taint?', Australian & New Zealand Grapegrower & Winemaker, 2004 111-115 (2004) [C3]
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2004 |
Whitehead JA, Lawrance GA, McCluskey A, ''Green' leaching: recyclable and selective leaching of gold-bearing ore in an ionic liquid', Green Chemistry, 6 313-315 (2004) [C1]
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Nova |
2003 |
Correa W, Edwards J, McCluskey A, McKinnon I, Scott JL, 'A thermodynamic investigation of solvent-free reactions', Green Chemistry, 5 30-33 (2003) [C1]
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2003 |
McCluskey A, Keller PA, Morgan J, Garner JA, 'Synthesis, molecular modeling and biological activity of methyl and thiomethyl substituted pyrimidines as corticotropin releasing hormone type 1 antagonists', Organic and Biomolecular Chemistry, 1 3353-3361 (2003) [C1]
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Nova |
2003 |
Ackland S, Bowyer MC, Baldwin ML, Garner JA, Walkom CC, Sakoff JA, McCluskey A, 'Cantharidin analogues: synthesis and evaluation of growth inhibition in a panel of selected tumour cell lines', Bioorganic Chemistry, 31 68-79 (2003) [C1]
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Nova |
2003 |
Keller PA, Kirkwood K, Morgan J, Westcott S, McCluskey A, 'The prevention of preterm labour -- corticotropin releasing hormone type 1 receptors as a target for drug design and development.', Mini reviews in medicinal chemistry, 3 295-303 (2003)
The role of the corticotropin releasing hormone in the onset of labour and the subsequent medicinal chemistry implications of CRH antagonists for the prevention of premature birth... [more]
The role of the corticotropin releasing hormone in the onset of labour and the subsequent medicinal chemistry implications of CRH antagonists for the prevention of premature birth, and identification of the CRH type 1 receptor as the target for this drug design, are reviewed here.
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2003 |
Leitch SK, McCluskey A, 'A High Yielding One-Pot Synthesis of Allylic-Vinylic Alcohols: The Adducts of Tetraallylstannane and a,?-Unsaturated Carbonyl Compounds', Synlett, - 699-701 (2003) [C1]
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2002 |
McCluskey A, Sim A, Sakoff J, 'Serine-threonine protein phosphatase inhibitors: Development of potential therapeutic strategies', Journal of Medicinal Chemistry, 45 1151-1175 (2002) [C1]
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Nova |
2002 |
McCluskey A, Robinson P, Hill TA, Scott J, Edwards JK, 'Green chemistry approaches to the Knoevenagel condensation: comparison of ethanol, water and solvent free (dry grind) approaches', Tetrahedron Letters, 43 3117-3120 (2002) [C1]
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Nova |
2002 |
Judeh Z, Ching C, Bu J, McCluskey A, 'The first Bischler-Napieralski cyclization in a room temperature ionic liquid', Tetrahedron Letters, 43 5089-5091 (2002) [C1]
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Nova |
2002 |
Gordon CM, Ritchie C, McCluskey A, Stark A, 'Indium- and tin-mediated allylation reactions in ionic liquids.', ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 224 U614-U614 (2002) |
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2002 |
Sakoff J, Ackland S, Baldwin ML, Atherton MA, McCluskey A, 'Anticancer activity and protein phosphatase 1 and 2A inhibition of a new generation of cantharidin analogues', Investigational New Drugs, 20 1-11 (2002) [C1]
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2002 |
McCluskey A, Ackland S, Gardiner E, Walkom CC, Sakoff J, 'The inhibition of protein phosphatases 1 and 2A: a new target for rational anti-cancer drug design?', Anti-Cancer Drug Design, 16 291-303 (2002) [C1]
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2002 |
McCluskey A, Atherton MA, Walkom CC, Bowyer M, Sim A, Young D, Sakoff J, 'The first two cantharidin analogues displaying PP1 selectivity', Bioorganic & Medicinal Chemistry Letters, 12 391-393 (2002) [C1]
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2001 |
Lengyel I, Nairn AC, McCluskey A, Toth G, Penke B, Rostas JAP, 'Auto-inhibition of Ca2+/calmodulin-dependent protein kinase II by its ATP-binding domain', Journal of Neurochemistry, 76 1066-1072 (2001) [C1]
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2001 |
McCluskey A, Muderawan IW, Muntari, Young DJ, 'A highly atom efficient, solvent promoted addition of tetraallylic, tetraallenic and tetrapropargylic stannanes to carbonyl compounds', Journal of Organic chemistry, 66 7811-7817 (2001) [C1]
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2001 |
McCluskey A, Young DJ, 'Organostannanes and ionic liquids: Toward green chemistry.', ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 221 U564-U564 (2001) |
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2001 |
McCluskey A, Lawrance GA, Owen M, Hamilton IC, 'Ionic liquids: From green chemistry to ore refining.', ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 221 U584-U584 (2001)
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2001 |
McCluskey A, Walkom CC, Bowyer MC, Ackland SP, Gardiner E, Sakoff JA, 'Cantharimides: A new class of modified cantharidin analogues inhibiting protein phosphatases 1 and 2A', Bioorganic & Medicinal Chemistry Letters, 11 2941-2946 (2001) [C1]
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Nova |
2001 |
McCluskey A, Sakoff JA, 'Small molecule inhibitors of serine/threonine protein phosphatases.', Mini reviews in medicinal chemistry, 1 43-55 (2001)
Serine/threonine protein phosphatases have long been ignored as potential therapeutic targets for two reasons, one the biochemical significance of these proteins has not been appr... [more]
Serine/threonine protein phosphatases have long been ignored as potential therapeutic targets for two reasons, one the biochemical significance of these proteins has not been appreciated and two, many natural protein phosphatase inhibitors are potent toxins and are considered unsuitable for clinical use. This review outlines the biochemical role of this protein family in cancer, cystic fibrosis, immunosuppression and, cardiac and neurological disorders. Particular emphasis is also given to the synthesis of selective small molecule inhibitors and their clinical exploitation.
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2000 |
McCluskey A, Finn M, Bowman M, Keller P, Smith R, '3,5-Dimethyl-7-hydrazinothiazolo[4,5-d]pyradazine-7-thiol: A corticotrophin releasing hormone type 1 receptor agonist', Australian Journal of Chemistry, 53 905-908 (2000) [C1] |
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2000 |
McCluskey A, Finn M, Bowman M, Keller PA, Smith R, '2,7-dimethylthiazolo[4,5-d] pyradazine-4-(5H)-thione: a corticotrophin releasing hormone type 1 receptor agonist', Australian journal of chemistry, 905-908 (2000) [C1]
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2000 |
McCluskey A, Garner JA, Caballero S, Young D, 'Tetraallylstannane and Weinreb amides: a simple 'green' route to N-protected homoallylic alcohols and allyl ketones', Tetrahedron Letters, 41 8147-8151 (2000) [C1]
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2000 |
McCluskey A, Atherton MA, Mudgee L, Sim A, Sakoff JA, Quinn R, 'Anhydride modified cantharidin analogues. Is ring opening important in the inhibition of protein phosphatase 2A?', European Journal of Medicinal Chemistry, 35 957-964 (2000) [C1]
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2000 |
Bowyer MC, 'Anhydride Modified Cantharidin Analogues: Synthesis, Inhibition of Protein Phosphatases 1 and 2A and Anticancer Activity', Bioorganic & Medicinal Chemistry Letters, 10 1687-1690 (2000) [C1]
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2000 |
McCluskey A, Elfick LG, Morgan J, Garner JA, Keller P, 'Corticotropin releasing hormone: Therapeutic implications and medicinal chemistry developments', Bioorganic and Medicinal Chemistry., 8 1213-1223 (2000) [C1]
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2000 |
Sakoff JA, McCluskey A, Sims ATR, Stewart JF, Ackland SP, 'A counter intuitive therapy for the treatment of cancer: Inhibition of protein phosphatases 1 and 2A by cantharidin (Spanish Fly) analogues.', CLINICAL CANCER RESEARCH, 6 4495S-4495S (2000)
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1999 |
Keller PA, Bowman M, Dang KH, Garner JA, Leach SP, Smith R, McCluskey A, 'Pharmacophore development for corticotropin-releasing hormone: new insights into inhibitor activity', Journal of Medicinal Chemistry, 42, No. 13 2351-2357 (1999) [C1]
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1999 |
McCluskey A, Garner JA, Smith R, Leach S, Dang D, Bowman M, Keller P, 'Pharmacophore development for corticotrophin releasing hormone; new insights into inhibitor activity', Journal of Medicinal Chemistry, 42 2351-2357 (1999) [C1] |
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1999 |
Garner JA, McCluskey A, 'Regiocontrolled amination of dichloropyrimidines in LiC104-Et20 solutions', Heterocyclic Communications, 5, No. 6 503-508 (1999) [C1]
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1999 |
McCluskey A, Garner JA, 'Garner, J, McCluskey, A, "A simple, expedient synthesis of substituted pyrimidines: Aminolysis of dichloropyrimidines in the presence of LiClO4', Heterocyclic Communications, 5 503-508 (1999) [C1] |
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1999 |
Gordon CM, McCluskey A, 'Ionic liquids: a convenient solvent for environmentally friendly allylation reactions with tetraallylstannane', Chemical Communications, -- 1431-1432 (1999) [C1]
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1999 |
McCluskey A, 'The allylation of carbonyl (and acetal) compounds by tetraallylstannane', Green Chemistry, -- 167-168 (1999) [C1] |
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1999 |
McCluskey A, 'Water promoted organic chemistry. The allylation of carbonyl (and acetal) compounds by tetraallylstannane', Green Chemistry, 1 161-162 (1999) [C1]
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1998 |
McCluskey A, Ying L, Camp D, Moni R, Quinn R, 'Diimidazo[1,2-C;4',5'-E] Pyrimidines N6-N1 Conformationally Restricted Andenosines', Bioorganic and Medicinal Chemistry Letters, 8 695-698 (1998) [C1]
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1998 |
McCluskey A, Dunkin I, 'Tetrachlorocyclopentadienone O-oxide, A Facile Oxygen Transfer Reagent, Further Evidence for the Disproportionation of Cycloalkoky Radicals', Bulletin of the Chemical Society of Japan, 71 1397-1400 (1998) [C1]
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1998 |
McCluskey A, Wayan Muderawan I, Muntari J, Young D, 'Solvent Assisted Addition of Tetraallylic, Tetraallenic and Tetraaproparagylic Stannanes to Aldehydes and Acetals', SynLett, -- 909-912 (1998) [C1]
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1997 |
Cokley TM, Harvey PJ, Marshall RL, McCluskey A, Young DJ, 'Solvent-mediated allylation of carbonyl compounds with allylic stannanes', JOURNAL OF ORGANIC CHEMISTRY, 62 1961-1964 (1997)
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1997 |
McCluskey A, Mayer DM, Young DJ, 'A simple one pot procedure for the generation of homoallylic alcohols from acetals and amino acetals', TETRAHEDRON LETTERS, 38 5217-5218 (1997)
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1997 |
Cokley TM, Isaacs NS, McCluskey A, Young DJ, 'High pressure allylstannane addition to alpha-amino aldehydes: Syn diastereoselectivity in the absence of chelation control.', MAIN GROUP METAL CHEMISTRY, 20 581-582 (1997)
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1996 |
Cokley TM, Marshall RL, McCluskey A, Young DJ, 'The solvent promoted addition of tetraallyltin to aldehydes: A convenient and chemoselective allylation procedure', TETRAHEDRON LETTERS, 37 1905-1908 (1996)
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1996 |
McCluskey A, Taylor C, Quinn RJ, Suganuma M, Fujiki H, 'Inhibition of protein phosphatase 2A by cantharidin analogues.', BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 6 1025-1028 (1996)
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1995 |
DUNKIN IR, MCCLUSKEY A, 'TETRACHLOROCYCLOPENTADIENONE O-OXIDE, A FACILE OXYGEN-ATOM TRANSFER REAGENT - THE OXIDATION OF CYCLOHEXENE', JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 89 157-161 (1995)
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1995 |
MCCLUSKEY A, DUNKIN IR, 'SUPPRESSION OF THE WOLFF REARRANGEMENT OF AN UNSTRAINED ALPHA-CARBONYL CARBENE BY CO AND O-2 IN LOW-TEMPERATURE MATRICES', AUSTRALIAN JOURNAL OF CHEMISTRY, 48 1107-1116 (1995)
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1995 |
BLANCH RJ, MCCLUSKEY A, 'XCN (X=CL, BR AND I) - A NOVEL SOURCE OF ISOCYANOGEN', CHEMICAL PHYSICS LETTERS, 241 116-120 (1995)
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1994 |
DUNKIN IR, MCCLUSKEY A, 'A SPECTROSCOPIC STUDY OF THE REACTION OF THE CARBENE, TETRABROMOCYCLOPENTADIENYLIDENE, WITH O2 IN LOW-TEMPERATURE MATRICES', SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 50 151-160 (1994)
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1994 |
DUNKIN IR, MCCLUSKEY A, 'CARBONYL CYANIDE O-OXIDE, THE ADDUCT OF DICYANOMETHYLENE AND DIOXYGEN IN ARGON MATRICES AT 12-K', SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 50 209-218 (1994)
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1993 |
DUNKIN IR, MCCLUSKEY A, 'TETRABROMOCYCLOPENTADIENYLIDENE - GENERATION AND REACTION WITH CO IN LOW-TEMPERATURE MATRICES', SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 49 1179-1185 (1993)
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1993 |
DUNKIN IR, MCCLUSKEY A, 'TETRACHLOROCYCLOPENTADIENONE O-OXIDE, A FACILE OXYGEN-ATOM TRANSFER REAGENT - THE OXIDATION OF CYCLOHEXANE', JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 74 159-164 (1993)
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1986 |
DUNKIN IR, BELL GA, MCCLEOD FG, MCCLUSKEY A, 'AN INFRARED STUDY OF THE FORMATION AND PHOTOCHEMICAL DECOMPOSITION OF TETRACHLOROCYCLOPENTADIENONE O-OXIDE IN LOW-TEMPERATURE MATRICES', SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 42 567-574 (1986)
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