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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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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2020 |
Md Yusof EN, Latif MAM, Tahir MIM, Sakoff JA, Veerakumarasivam A, Page AJ, et al., 'Homoleptic tin(IV) compounds containing tridentate ONS dithiocarbazate Schiff bases: Synthesis, X-ray crystallography, DFT and cytotoxicity studies', Journal of Molecular Structure, 1205 (2020) [C1]
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2020 |
Baker JR, Sakoff JA, McCluskey A, 'Cover Image, Volume 40, Issue 3', Medicinal Research Reviews, 40 (2020)
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2020 |
Yusof ENM, Page AJ, Sakoff JA, Simone MI, Veerakumarasivam A, Tiekink ERT, Ravoof TBSA, 'Tin(IV) compounds of tridentate thiosemicarbazone Schiff bases: Synthesis, characterization, in-silico analysis and in vitro cytotoxicity', Polyhedron, 189 (2020) [C1]
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2020 |
Bjelosevic A, Sakoff J, Gilbert J, Zhang Y, Gordon C, Aldrich-Wright JR, 'Synthesis, characterisation, and biological activity of the ruthenium complexes of the N
© CSIRO 2020. A series of complexes of the type rac-[Ru(N4-TL)(PL)]2+ (where N4-TL=1, 6-di(2'-pyridyl)-2, 5-dimethyl-2, 5-diazahexane (picenMe2, N4-TL-2) and PL=1, 10-phenant... [more]
© CSIRO 2020. A series of complexes of the type rac-[Ru(N4-TL)(PL)]2+ (where N4-TL=1, 6-di(2'-pyridyl)-2, 5-dimethyl-2, 5-diazahexane (picenMe2, N4-TL-2) and PL=1, 10-phenanthroline (phen, Ru-2), dipyrido[3, 2-d:2', 3'-f]quinoxaline (dpq, Ru-3), 7, 8-dimethyl-dipyrido[3, 2-a:2', 3'-c]phenazine (dppzMe2, Ru-4), 2-phenyl-1H-imidazo[4, 5-f][1, 10]phenanthroline (phenpyrBz, Ru-5), 2-(p-tolyl)-1H-imidazo[4, 5-f][1, 10]phenanthroline (phenpyrBzMe, Ru-6), and 2-(4-nitrophenyl)- 1H-imidazo[4, 5-f][1, 10]phenanthroline (phenpyrBzNO2, Ru-7), were synthesised. All structures were confirmed using NMR, electrospray ionisation mass spectrometry (ESI-MS), high-performance liquid chromatography (HPLC), and UV analysis and for four complexes X-ray crystallography. The in vitro cytotoxicity assays revealed that Ru-6 was 5, 10, and 40-fold more potent than oxaliplatin, cisplatin, and carboplatin, respectively.
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2020 |
Yusof ENM, Ishak NNM, Latif MAM, Tahir MIM, Sakoff JA, Page AJ, et al., 'Selective cytotoxicity of organotin(IV) compounds with 2,3-dihydroxybenzyldithiocarbazate Schiff bases', Research on Chemical Intermediates, 46 2351-2379 (2020) [C1]
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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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2020 |
Scorgie FE, Garg MB, Gilbert J, Sakoff JA, Lincz LF, 'A simplified method to calculate telomere length from Southern blot images of terminal restriction fragment lengths', BioTechniques, 68 28-34 (2020) [C1]
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2020 |
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, (2020)
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2019 |
McGhie BS, Sakoff J, Gilbert J, Aldrich-Wright JR, 'Synthesis and characterisation of platinum(IV) polypyridyl complexes with halide axial ligands', Inorganica Chimica Acta, 495 (2019)
© 2019 A series of complexes of the type [Pt(PL)(AL)(X)2]2+ (where PL = 1,10-phenanthroline, 5-methyl-1,10-phenanthroline or 5,6-dimethyl-1,10-phenanthroline; AL = 1S,2S-diaminocy... [more]
© 2019 A series of complexes of the type [Pt(PL)(AL)(X)2]2+ (where PL = 1,10-phenanthroline, 5-methyl-1,10-phenanthroline or 5,6-dimethyl-1,10-phenanthroline; AL = 1S,2S-diaminocyclohexane and, X = Cl, Br or I) with anticancer potency, were synthesised in a one pot reaction using N-halogensuccinimide (NXS) as both the source of the ligand and the oxidizing reagent. It was determined that 2.4 equivalents of NXS resulted in 100% oxidation of Pt(II) in a solution of equal parts H2O, ethanol and 1 M HCl. This method of oxidation was 24 times faster than the established peroxide method resulting in the acceleration of the complete synthesis of [Pt(PL)(AL)(X)2]2+. All structures were confirmed using NMR, ESI-MS, CD and UV, while the purity was confirmed by microanalysis. The in vitro cytotoxicity assays revealed that they were more active than analogous complexes with hydroxido axial ligands, and share comparable activity with the corresponding Pt(II) complex.
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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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2019 |
Nadia Md Yusof E, Latif MAM, Tahir MIM, Sakoff J, Simone M, Page AJ, et al., 'o-Vanillin Derived Schiff Bases and Their
Organotin(IV) Compounds: Synthesis, Structural
Characterisation, In-Silico Studies and Cytotoxicity', International Journal of Molecular Sciences, 20 (2019) [C1]
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2019 |
Deo KM, Sakoff J, Gilbert J, Zhang Y, Wright JRA, 'Synthesis, characterisation and potent cytotoxicity of unconventional platinum(iv) complexes with modified lipophilicity', DALTON TRANSACTIONS, 48 17217-17227 (2019)
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2019 |
Deo KM, Sakoff J, Gilbert J, Zhang Y, Wright JRA, 'Synthesis, characterisation and influence of lipophilicity on cellular accumulation and cytotoxicity of unconventional platinum(iv) prodrugs as potent anticancer agents', DALTON TRANSACTIONS, 48 17228-17240 (2019)
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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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2019 |
Pham HNT, Sakoff JA, Vuong QV, Bowyer MC, Scarlett CJ, 'Phytochemical, antioxidant, anti-proliferative and antimicrobial properties of Catharanthus roseus root extract, saponin-enriched and aqueous fractions', Molecular Biology Reports, 46 3265-3273 (2019) [C1]
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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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2018 |
Pham HNT, Sakoff JA, Vuong QV, Bowyer MC, Scarlett CJ, 'Screening phytochemical content, antioxidant, antimicrobial and cytotoxic activities of Catharanthus roseus (L.) G. Don stem extract and its fractions', Biocatalysis and Agricultural Biotechnology, 16 405-411 (2018) [C1]
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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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2018 |
Hong NTP, Sakoff JA, Vuong QV, Bowyer MC, Scarlett CJ, 'Comparative cytotoxic activity between kaempferol and gallic acid against various cancer cell lines', DATA IN BRIEF, 21 1033-1036 (2018)
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2018 |
Pages BJ, Sakoff J, Gilbert J, Zhang Y, Kelly SM, Hoeschele JD, Aldrich-Wright JR, 'Combining the platinum(II) drug candidate kiteplatin with 1,10-phenanthroline analogues', DALTON TRANSACTIONS, 47 2156-2163 (2018)
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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]
© 2018 The Authors. Bolinaquinone is a natural product that is a structurally complex, cytotoxic sesquiterpene quinone. A scaffold simplification and focused library approach usin... [more]
© 2018 The Authors. 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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2018 |
Hong NTP, Sakoff JA, Bond DR, Quan VV, Bowyer MC, Scarlett CJ, 'In vitro antibacterial and anticancer properties of Helicteres hirsuta Lour. leaf and stem extracts and their fractions', MOLECULAR BIOLOGY REPORTS, 45 2125-2133 (2018) [C1]
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2017 |
Van TN, Sakoff JA, Scarlett CJ, 'Physicochemical, Antioxidant, and Cytotoxic Properties of Xao Tam Phan (Paramignya trimera) Root Extract and Its Fractions', CHEMISTRY & BIODIVERSITY, 14 (2017) [C1]
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2017 |
Nguyen VT, Sakoff JA, Scarlett CJ, 'Physicochemical Properties, Antioxidant and Cytotoxic Activities of Crude Extracts and Fractions from Phyllanthus amarus.', Medicines, 4 (2017) [C1]
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2017 |
Bhuyan DJ, Sakoff J, Bond DR, Predebon M, Vuong QV, Chalmers AC, et al., 'In vitro anticancer properties of selected Eucalyptus species', IN VITRO CELLULAR & DEVELOPMENTAL BIOLOGY-ANIMAL, 53 604-615 (2017) [C1]
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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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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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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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2017 |
Van TN, Sakoff JA, Scarlett CJ, 'Physicochemical Properties, Antioxidant and Anti-proliferative Capacities of Dried Leaf and Its Extract from Xao tam phan (Paramignya trimera)', CHEMISTRY & BIODIVERSITY, 14 (2017) [C1]
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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]
© CSIRO 2016. Plants from the family Myoporaceae, which includes the genus Myoporum, are extremely prized by the Australian Aboriginal people for their medicinal properties. Leave... [more]
© CSIRO 2016. 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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2016 |
Pages BJ, Sakoff J, Gilbert J, Rodger A, Chmel NP, Jones NC, et al., 'Multifaceted Studies of the DNA Interactions and In Vitro Cytotoxicity of Anticancer Polyaromatic Platinum(II) Complexes', CHEMISTRY-A EUROPEAN JOURNAL, 22 8943-8954 (2016)
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2016 |
Pages BJ, Sakoff J, Gilbert J, Zhang Y, Li F, Preston D, et al., 'Investigating the cytotoxicity of platinum(II) complexes incorporating. bidentate pyridy1-1,2,3-triazole "click" ligands', JOURNAL OF INORGANIC BIOCHEMISTRY, 165 92-99 (2016)
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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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2016 |
Chuen TLK, Vuong QV, Hirun S, Bowyer MB, Predebon MJ, Goldsmith CD, et al., 'Antioxidant and anti-proliferative properties of Davidson s plum (Davidsonia pruriens F. Muell) phenolic-enriched extracts as affected by different extraction solvents', Journal of Herbal Medicine, 6 187-192 (2016) [C1]
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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]
© The Royal Society of Chemistry 2016. 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-c... [more]
© The Royal Society of Chemistry 2016. 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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2015 |
MacIas FJ, Deo KM, Pages BJ, Wormell P, Clegg JK, Zhang Y, et al., 'Synthesis and Analysis of the Structure, Diffusion and Cytotoxicity of Heterocyclic Platinum(IV) Complexes', Chemistry - A European Journal, 21 16990-17001 (2015) [C1]
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. We have developed six dihydroxidoplatinum(IV) compounds with cytotoxic potential. Each derived from active platinum(II) sp... [more]
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. We have developed six dihydroxidoplatinum(IV) compounds with cytotoxic potential. Each derived from active platinum(II) species, these complexes consist of a heterocyclic ligand (HL) and ancillary ligand (AL) in the form [Pt(HL)(AL)(OH)2]2+, where HL is a methyl-functionalised variant of 1,10-phenanthroline and AL is the S,S or R,R isomer of 1,2-diaminocyclohexane. NMR characterisation and X-ray diffraction studies clearly confirmed the coordination geometry of the octahedral platinum(IV) complexes. The self-stacking of these complexes was determined using pulsed gradient stimulated echo nuclear magnetic resonance. The self-association behaviour of square planar platinum(II) complexes is largely dependent on concentration, whereas platinum(IV) complexes do not aggregate under the same conditions, possibly due to the presence of axial ligands. The cytotoxicity of the most active complex, exhibited in several cell lines, has been retained in the platinum(IV) form.
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2015 |
Pages BJ, Zhang Y, Li F, Sakoff J, Gilbert J, Aldrich-Wright JR, 'Cytotoxicity and Structural Analyses of 2,2'-Bipyridine-, 4,4'-Dimethyl-2,2'-bipyridine- and 2-(2'-Pyridyl)quinoxalineplatinum(II) Complexes', European Journal of Inorganic Chemistry, 2015 4167-4175 (2015) [C1]
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Platinum anticancer complexes incorporating 2,2'-bipyridine (bpy), 4,4'-dimethyl-2,2'-bipyridine (44Me<i... [more]
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Platinum anticancer complexes incorporating 2,2'-bipyridine (bpy), 4,4'-dimethyl-2,2'-bipyridine (44Me<inf>2</inf>bpy) or 2-(2'-pyridyl)quinoxaline (2pq) as polyaromatic ligands and the S,S or R,R isomer of 1,2-diaminocyclohexane as ancillary ligands in the form [Pt(P<inf>L</inf>)(A<inf>L</inf>)]<sup>2+</sup> have been synthesised and characterised. X-ray diffraction was used to elucidate the structure and stacking behaviour of the complexes, revealing interesting properties that may impact their biological activity. Pulsed gradient spin-echo NMR experiments elucidated the aggregation behaviour of these complexes in solution. The cytotoxicity of each complex was assessed against the L1210 murine leukaemia, HT29 human colon carcinoma and U87 human glioblastoma cell lines and compared to other complexes within this class. The complexes incorporating 44Me<inf>2</inf>bpy were found to be the most potent at inhibiting cell growth with IC<inf>50</inf> values for the S,S isomer (0.13-0.5 µM) less than that for cisplatin (0.36-11 µM), oxaliplatin (0.9-1.8 µM) or carboplatin (>50 µM). Most complexes were found to be very effective against HT29 colon carcinoma cells.
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2015 |
Vuong QV, Hirun S, Chuen TLK, Goldsmith CD, Munro B, Bowyer MC, et al., 'Physicochemical, antioxidant and anti-cancer activity of a Eucalyptus robusta (Sm.) leaf aqueous extract', INDUSTRIAL CROPS AND PRODUCTS, 64 167-174 (2015) [C1]
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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]
© 2015 Elsevier Ltd. Abstract An efficient and divergent methodology for the synthesis of new anthracenone-pyranones and anthracenone-furans is described. Key reactions discussed ... [more]
© 2015 Elsevier Ltd. 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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2015 |
Macias FJ, Deo KM, Pages BJ, Wormell P, Clegg JK, Zhang Y, et al., 'Synthesis and Analysis of the Structure, Diffusion and Cytotoxicity of Heterocyclic Platinum(IV) Complexes.', Chemistry, 21 16990-17001 (2015)
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2014 |
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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2014 |
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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2014 |
Vuong QV, Sadeqzadeh E, Hirun S, Goldsmith CD, Zammitt N, Bowyer MB, et al., 'Phenolic Compounds, Antioxidant and Anti-Cancer Properties of the Australian Maroon Bush Scaevola spinescens (Goodeniaceae)', Journal of Bioanalysis & Biomedicine, S12 (2014) [C1]
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2014 |
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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2014 |
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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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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2013 |
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 |
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 |
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 |
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 |
Garg MB, Lincz L, Adler K, Scorgie FE, Ackland S, Sakoff JA, 'Predicting 5-Fluorouracil toxicity in colorectal cancer patients from peripheral blood cell telomere length - A multivariate analysis', British Journal of Cancer, 107 1525-1533 (2012) [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 |
Garg MB, Sakoff JA, Ackland S, 'A simple HPLC method for plasma level monitoring of mitotane and its two main metabolites in adrenocortical cancer patients', Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, 879 2201-2205 (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 |
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, 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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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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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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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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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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2010 |
De Bock CE, Garg ML, Scott NM, Sakoff JA, Scorgie FE, Ackland S, Lincz L, 'Association of thymidylate synthase enhancer region polymorphisms with thymidylate synthase activity in vivo', Pharmacogenomics Journal, 1-8 (2010) [C1]
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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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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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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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2008 |
Lincz L, Mudge L-M, Scorgie FE, Sakoff JA, Hamilton C, Seldon MR, 'Quantification of hTERT splice variants in melanoma by SYBR green real-time polymerase chain reaction indicates a negative regulatory role for the [beta symbol] deletion variant', Neoplasia, 10 1131-1137 (2008) [C1]
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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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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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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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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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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 |
Lincz L, Scorgie F, Sakoff J, Fagan K, Ackland S, Enno A, 'Telomere length predicts neutrophil recovery in absence of G-CSF after autologous peripheral blood stem cell transplantation', Bone Marrow Transplant, 34 439-445 (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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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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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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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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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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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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2002 |
Garg MB, Sevester JC, Sakoff JA, Ackland SP, 'Simple liquid chromatographic method for the determination of uracil and dihydrouracil plasma levels: a potential pretreatment predictor of 5-fluorouracil toxicity', JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, 774 223-230 (2002)
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2002 |
Sakoff J, De Waal E, Garg M, Denham J, Scorgie F, Enno A, et al., 'Telomere Length in Haemopoietic Stem Cells can be Determined from that of Mononuclear Blood Cells or Whole Blood', Leukemia and Lymphoma, 43(10) 2017-2020 (2002) [C1]
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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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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, 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 |
Sakoff J, Ackland S, 'Thymidylate synthase inhibition induces S-phase arrest, biphasic mitochondrial alterations and caspase-dependent apoptosis in leukaemia cells', Cancer Chemotherapy and Pharmacology, 46 477-487 (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 |
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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1996 |
Sakoff J, Dunstan RH, Murdoch RN, 'Uterine lipid alterations during early pseudopregnancy and following the artificial induction of decidualization by Concanavalin A in QS mice', Molecular reproductive Development, 44 93-102 (1996) [C1]
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1996 |
Sakoff JA, Murdoch RN, 'The role of calcium in the artificially induced decidual cell reaction in pseudopregnant mice', BIOCHEMICAL AND MOLECULAR MEDICINE, 57 81-90 (1996)
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1996 |
Sakoff J, Murdoch RN, 'The role of calcium ions in the Concanavalin A induced decidual cell reaction in pseudopregnant mice', Biochemical and Molecular Medicine, 57 81-90 (1996) [C1] |
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1995 |
Sakoff J, Murdoch RN, 'Uterine receptivity to the artificial deciduogenic agent, Concanavalin A in pseudopregnant', Reproduction, Fertility and Development, 7 1095-1100 (1995) [C1]
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1994 |
Sakoff J, Murdoch RN, 'Alterations in uterine calcium ions during the induction of the decidual cell reaction in pseudopregnant mice', journal of reproduction and fertility, 101 97-102 (1994) [C1]
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Legge WJ, Shimadate Y, Ghorbani M, Sakoff J, Houston TA, Kato A, et al., 'Borylated methyl cinnamates: Expedited synthesis, characterization, crystallographic analysis and biological activities in glycosidase inhibition and in cancer cells lines.
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