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Dr Michela Simone

Lecturer

School of Environmental and Life Sciences

Career Summary

Biography

Research Expertise
Michela joined the School of Environmental and Life Sciences, in the Discipline of Chemistry in January 2014. She received her BSc/Masters degree from the Victoria University of Manchester, UK. She went on to obtain her D.Phil. from the University of Oxford under the supervision of Professor George Fleet in 2006. Michela’s research interests lie under the broad umbrella of Medicinal Chemistry with a Glycobiological spin! She is interested in the synthesis and evaluation of novel classes of glycosidase inhibitors from carbohydrate starting materials to molecular recognition and supramolecular chemistry. Recently she has also moved into the area of bioinorganic chemistry primarily as relating to cancer research. Carbohydrates are found ubiquitously in Nature where they represent a unique family of polyfunctional compounds which Nature extensively manipulates and finely tunes to serve a multitude of biological purposes. Carbohydrate building blocks provide a rich chiral pool of cheap, readily available and highly versatile starting materials for the enantiospecific synthesis of highly functionalised homochiral targets. They are utilised in the synthesis of many classes of compounds, including iminosugars. Iminosugars represent an important category of glycosidase inhibitors and proven to possess therapeutic potential in the management and treatment of many medical conditions, including diabetes, lysosomal storage diseases, viral infections and cancer. The amazing diversity of biological roles found within this class of small molecules is evidence of a remarkable economy of structural information in nature, which in molecular weight terms completely surpasses anything achieved by the amino acids. The Simone group is working in this burgeoning field of glycomimetics and undertaken the synthesis and evaluation of novel classes of iminosugars as anti-viral agents. Another area of active research in the group is the fluorescent tagging of proteins. It is vital to biomedicine efforts to understand the spatial and temporal underpinnings of life inside cells in vivo versus in fixed cells. Current protein fluorescent tags are plagued by many draw-backs including excessive bulk, high toxicity, the need for extensive genetic engineering and the use of covalent bonds to link the sensor to the protein under investigation. These result in their limited use in vivo. We are undertaking the fluorescent tagging of proteins via innovative strategies, namely by the use of small fluorescent supramolecular entities which are engineered to transiently and selectively bind to the protein surfaces of interest. The Simone group has also more recently delved into the area of bioinorganic chemistry. The group is currently contributing to the synthesis of novel classes of platinum- and cobalt-based compounds for evaluation as chemotherapeutics and novel 99mTc-based compounds which will be evaluated as cancer imaging agents.

Teaching Expertise
CHEM3310 (Molecular Organic Synthesis, S1) CHEM2310 (Organic Chemistry, S1) CHEM3590 (Chemistry Project, S1 and S2) CHEM4410 (Hons, S1 and S2) CHEM3550 (Medicinal Chemistry, S2)

Qualifications

  • PhD (Organic Chemistry), University of Oxford - UK

Keywords

  • carbohydrate chemistry
  • glycobiology
  • medicinal chemistry

Fields of Research

Code Description Percentage
030401 Biologically Active Molecules 50
030499 Medicinal and Biomolecular Chemistry not elsewhere classified 50

Professional Experience

UON Appointment

Title Organisation / Department
Lecturer University of Newcastle
School of Environmental and Life Sciences
Australia

Awards

Award

Year Award
2014 RACI Nyholm Youth Lecturer 2015-2016
RACI
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Publications

For publications that are currently unpublished or in-press, details are shown in italics.


Journal article (37 outputs)

Year Citation Altmetrics Link
2015 Cossar PJ, Hizartzidis L, Simone MI, McCluskey A, Gordon CP, 'The expanding utility of continuous flow hydrogenation.', Org Biomol Chem, 13 7119-7130 (2015)
DOI 10.1039/c5ob01067e
Co-authors Adam Mccluskey
2015 Cossar PJ, Hitzartzidis L, Simone M, McCluskey A, Gordon CP, 'The expanding utility of continuous flow hydrogenation', Organic and Biomolecular Chemistry, (2015)
2015 Cossar PJ, Hizartzidis L, Simone MI, McCluskey A, Gordon C, 'The expanding utility of continuous flow hydrogenation', Org. Biomol. Chem., (2015)
DOI 10.1039/C5OB01067E
2014 Simone MI, Houston TA, 'A Brief Overview of Recent Advances in the Applications of Boronic Acids Relevant to Glycomics', Journal of Glycomics & Lipidomics, 04 e124 (2014) [C3]
DOI 10.4172/2153-0637.1000e124
2014 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.

DOI 10.1039/c4ra09605c
Citations Scopus - 2Web of Science - 2
Co-authors Adam Mccluskey
2014 Moyes AJ, Khambata RS, Villar I, Bubb KJ, Baliga RS, Lumsden NG, et al., 'Endothelial C-type natriuretic peptide maintains vascular homeostasis', Journal of Clinical Investigation, 1 (2014) [C1]
DOI 10.1172/JCI74281
Citations Scopus - 3Web of Science - 3
2014 Sayer JR, Wallde n K, Pesnot T, Campbell F, Gane PJ, Simone M, et al., '2- and 3-substituted imidazo[1,2-a]pyrazines as inhibitors of bacterial type IV secretion', Bioorganic and Medicinal Chemistry, (2014) [C1]

A novel series of 8-amino imidazo[1,2-a]pyrazine derivatives has been developed as inhibitors of the VirB11 ATPase HP0525, a key component of the bacterial type IV secretion syste... [more]

A novel series of 8-amino imidazo[1,2-a]pyrazine derivatives has been developed as inhibitors of the VirB11 ATPase HP0525, a key component of the bacterial type IV secretion system. A flexible synthetic route to both 2- and 3-aryl substituted regioisomers has been developed. The resulting series of imidazo[1,2-a]pyrazines has been used to probe the structure-activity relationships of these inhibitors, which show potential as antibacterial agents.

DOI 10.1016/j.bmc.2014.09.036
2013 Risseeuw M, Overhand M, Fleet GWJ, Simone MI, 'A compendium of cyclic sugar amino acids and their carbocyclic and heterocyclic nitrogen analogues', Amino Acids, 45 613-689 (2013) [C1]
DOI 10.1007/s00726-013-1521-1
Citations Scopus - 19Web of Science - 15
2013 Reed JH, Turner P, Kato A, Houston TA, Simone M, '1-O-Benzyl-2,3-O-isopropylidene-6-O-tosyl-a-L-sorbofuranose', Acta Crystallographica Section E: Structure Reports Online, 69 o1069-o1070 (2013) [C1]
DOI 10.1107/S1600536813015638
2012 Dube H, Selwood D, Malouitre S, Capano M, Simone MI, Crompton M, 'A mitochondrial-targeted cyclosporin A with high binding affinity for cyclophilin D yields improved cytoprotection of cardiomyocytes', BIOCHEMICAL JOURNAL, 441 901-907 (2012) [C1]
DOI 10.1042/BJ20111301
Citations Scopus - 14Web of Science - 9
2012 Simone MI, Soengas RG, Jenkinson SF, Evinson EL, Nash RJ, Fleet GWJ, 'Synthesis of three branched iminosugars [(3R,4R,5S)-3-(hydroxymethyl)piperidine-3,4,5-triol, (3R,4R,5R)-3-(hydroxymethyl)piperidine-3,4,5-triol and (3S,4R,5R)-3-(hydroxymethyl)piperidine-3.4,5-triol] and a branched trihydroxynipecotic acid [(3R,4R,5R)-3,4,5-trihydroxypiperidine-3-carboxylic acid] from sugar lactones with a carbon substituent at C-2', TETRAHEDRON-ASYMMETRY, 23 401-408 (2012) [C1]
DOI 10.1016/j.tetasy.2012.03.007
Citations Scopus - 9Web of Science - 8
2012 Soengas RG, Simone MI, Hunter S, Nash RJ, Evinson EL, Fleet GWJ, 'Hydroxymethyl-Branched Piperidines from Hydroxymethyl-Branched Lactones: Synthesis and Biological Evaluation of 1,5-Dideoxy-2-C-hydroxymethyl-1,5-imino-D-mannitol, 1,5-Dideoxy-2-C-hydroxymethyl-1,5-imino-L-gulitol and 1,5-Dideoxy-2-C-hydroxymethyl-1,5-imino-D-talitol', EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2394-2402 (2012) [C1]
DOI 10.1002/ejoc.201200054
Citations Scopus - 12Web of Science - 9
2012 Jenkinson SF, Thompson AL, Simone MI, 'Methyl 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-4-nitrobenzoate', Acta Crystallographica Section E: Structure Reports Online, 68 o2429-o2430 (2012) [C1]
DOI 10.1107/S1600536812029650
2012 Gooding M, Tudzarova S, Worthington RJ, Kingsbury SR, Rebstock A-S, Dube H, et al., 'Exploring the Interaction Between siRNA and the SMoC Biomolecule Transporters: Implications for Small Molecule-Mediated Delivery of siRNA', CHEMICAL BIOLOGY & DRUG DESIGN, 79 9-21 (2012)
DOI 10.1111/j.1747-0285.2011.01249.x
Citations Scopus - 3Web of Science - 3
2011 Simone MI, Edwards AA, Tranter GE, Fleet GWJ, 'C-3 branched delta-3,5-cis- and trans-THF sugar amino acids: synthesis of the first generation of branched homooligomers', AMINO ACIDS, 41 643-661 (2011) [C1]
DOI 10.1007/s00726-011-0849-7
Citations Scopus - 11Web of Science - 7
2010 Simone MI, Edwards AA, Parker SG, Tranter GE, Fleet GWJ, Watkin DJ, 'Pentafluorophenyl (3R,4R,5S)-5-{[(3R,4R,5S)-5-azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxamido] methyl}-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate', ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 66 O2699-U1584 (2010) [C1]
DOI 10.1107/S1600536810038559
Citations Scopus - 2Web of Science - 2
2010 Simone MI, Edwards AA, Cowley AR, Fleet GWJ, Watkin DJ, '(3R,4R,5R)-5-(Acetamidomethyl)-N-benzyl-3,4-dihydroxytetrahydrofuran-3-carboxamide', ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 66 O2750-U2003 (2010) [C1]
DOI 10.1107/S1600536810039589
Citations Scopus - 1Web of Science - 1
2009 Hobbs AJ, Gane P, Lumsden N, Nobles M, Rebstock A-S, Simone M, et al., 'Design and development of novel non-peptide agonists at natriuretic peptide receptor-C', FASEB JOURNAL, 23 (2009) [E3]
2008 Simone MI, Edwards AA, Tranter GE, Fleet GWJ, 'Carbon-branched delta-tetrahydrofuran sugar amino acids (SAAs) as dipeptide isostere scaffolds', TETRAHEDRON-ASYMMETRY, 19 2887-2894 (2008) [C1]
DOI 10.1016/j.tetasy.2008.12.012
Citations Scopus - 18Web of Science - 19
2007 Risseeuw MDP, Overhand M, Fleet GWJ, Simone MI, 'A compendium of sugar amino acids (SAA): scaffolds, peptide- and glyco-mimetics', TETRAHEDRON-ASYMMETRY, 18 2001-2010 (2007)
DOI 10.1016/j.tetasy.2007.08.004
Citations Scopus - 67Web of Science - 69
2007 Simone M, Fleet GWJ, Watkin DJ, '3,3': 5,6-Di-O-isopropylidene-3-C-hydroxy-methyl-(D)-allono-1,4-lactone: an organic structure containing large unoccupied voids', ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 63 O799-O801 (2007)
DOI 10.1107/S1600536807002061
Citations Scopus - 6Web of Science - 6
2007 Simone M, Fleet GWJ, Watkin DJ, '1,5-Anhydro-2,3-O-isopropylidene-L-lyxo-furanose [(1S,4S,5S,6R)-5,6-O-isopropylidene-2,7-dioxabicyclo[2.2.1]heptane-5,6-diol]', ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 63 O896-O897 (2007)
DOI 10.1107/S160053680700311X
Citations Scopus - 1Web of Science - 1
2007 Simone M, Fleet GWJ, Watkin DJ, '5-O-tert-butyldiphenylsilyl-2-C-hydroxymethyl-2,3-O-isopropylidene-2 ' O-trifluoromethanesulfonyl-D-ribono-1,4-lactone', ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 63 o1088-o1090 (2007)
DOI 10.1107/S1600536807004436
2007 Simone M, Fleet GWJ, Bream R, Watkin DJ, '5-Amino-5-deoxy-2-C-hydroxymethyl-2,3-O-iso-propylidene-(L)-lyxono-1,5-lactam', ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 63 o1409-o1411 (2007)
DOI 10.1107/S1600536807007568
Citations Scopus - 2Web of Science - 2
2006 Bleriot Y, Simone MI, Wormald MR, Dwek RA, Watkin DJ, Fleet GWJ, 'Sugar amino acids at the anomeric position of carbohydrates: synthesis of spirocyclic amino acids of 6-deoxy-L-lyxofuranose', TETRAHEDRON-ASYMMETRY, 17 2276-2286 (2006)
DOI 10.1016/j.tetasy.2006.07.027
Citations Scopus - 20Web of Science - 20
2006 Punzo F, Cowley AR, Watkin DJ, Simone MI, Edwards AA, Tranter GE, Fleet GWJ, 'Pentafluorophenyl (3R,4R,5R)-5-{[(3R,4R,5R)-5-azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydro-furan-3-carbonylamino]methyl}-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate', ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 62 O473-O475 (2006)
DOI 10.1107/S1600536805043205
Citations Scopus - 4Web of Science - 3
2006 Parker SG, Watkin DJ, Simone MI, Fleet GWJ, '3,4 : 5,6-di-O-isopropylidene-3-C-hydroxy-methyl-D-altrono-1,3 '-lactone', ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 62 O3961-O3963 (2006)
DOI 10.1107/S1600536806015881
Citations Scopus - 10Web of Science - 10
2006 Jockusch RA, Talbot FO, Rogers PS, Simone MI, Fleet GWJ, Simons JP, 'Carbohydrate amino acids: The intrinsic conformational preference for a beta-turn-type structure in a carbopeptoid building block', JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 128 16771-16777 (2006)
DOI 10.1021/ja0607133
Citations Web of Science - 21
2005 Punzo F, Watkin DJ, Simone MI, Fleet GWJ, '(3R,4R,5S)-5-(acetamidomethyl)-N-benzyl-3,4-dihydroxytetrahydrofuran-3-carboxamide', ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 61 O513-O515 (2005)
DOI 10.1107/S1600536805001467
Citations Scopus - 2Web of Science - 2
2005 Soengas R, Izumori K, Simone MI, Watkin DJ, Skytte UP, Soetaert W, Fleet GWJ, 'Kiliani reactions on ketoses: branched carbohydrate building blocks from D-tagatose and D-psicose', TETRAHEDRON LETTERS, 46 5755-5759 (2005)
DOI 10.1016/j.tetlet.2005.06.030
Citations Scopus - 45Web of Science - 49
2005 Simone MI, Soengas R, Newton CR, Watkin DJ, Fleet GWJ, 'Branched tetrahydrofuran alpha,alpha-disubstituted-delta-sugar amino acid scaffolds from branched sugar lactones: a new family of foldamers?', TETRAHEDRON LETTERS, 46 5761-5765 (2005)
DOI 10.1016/j.tetlet.2005.06.029
Citations Scopus - 30Web of Science - 29
2004 Hotchkiss D, Soengas R, Simone MI, van Ameijde J, Hunter S, Cowley AR, Fleet GWJ, 'Kiliani on ketoses: branched carbohydrate building blocks from D-fructose and L-sorbose', TETRAHEDRON LETTERS, 45 9461-9464 (2004)
DOI 10.1016/j.tetlet.2004.10.086
Citations Scopus - 52Web of Science - 52
2004 Watkins DJ, Muller M, Bleriot Y, Simone MI, Fleet GWJ, '(2S,3R,4R,5S)-3,4-O-isopropylidene-2-methyl-1-oxa-6,9-diazaspiro[4.5]decane-7,10-dione', ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 60 O1820-O1822 (2004)
DOI 10.1107/S1600536804022494
Citations Scopus - 2Web of Science - 2
2004 van Ameijde J, Cowley AR, Fleet GWJ, Nash RJ, Simone MI, Soengas R, '5-amino-5-deoxy-2-C-hydroxymethyl-2,3-O-isopropylidene-D-talono-1,5-lactam', ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 60 O2140-O2141 (2004)
DOI 10.1107/S1600536804025292
Citations Scopus - 9Web of Science - 4
2004 Cowley AR, Fleet GWJ, Simone MI, Soengas R, '3-O-tert-butyldimethylsilyl-2,2 ': 5,6-di-O-isopropylidene-2-C-hydroxymethyl-D-1,4-gluconolactone', ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 60 O2142-O2143 (2004)
DOI 10.1107/S1600536804025310
Citations Scopus - 5Web of Science - 5
2004 Punzo F, Watkin DJ, Simone MI, Fleet GWJ, '(1R,5S,8R)-1,8-dihydroxy-6-oxa-3-azabicyclo[3.2.1]octan-2-one', ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 60 O2315-O2317 (2004)
DOI 10.1107/S1600536804028983
Citations Web of Science - 3
2004 Newton CR, Michela IS, Fleet GWJ, Blériot Y, Watkin DJ, '2- -Hydroxymethyl-2,3- -isopropylidene- -ribono-1,5-lactam', Acta Crystallographica Section E Structure Reports Online, 60 o909-o910 (2004)
DOI 10.1107/S1600536804008141
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Conference (3 outputs)

Year Citation Altmetrics Link
2011 Quinteiro FM, Gane P, Rebstock A-S, Simone M, Djordjevic S, Hobbs A, Selwood D, 'Design and development of novel non-peptide agonists at NPR-C', Proceedings paper in BMC Pharmacology, Halle, Germany (2011)
DOI 10.1186/1471-2210-11-S1-P54
2005 Simone M, 'Branched sugar amino acids as foldamers', ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, Washington, DC (2005)
2005 Edwards AA, Fleet GWJ, Mayes BA, Hunterz SJ, Soengas RG, Simone M, Tranter GE, 'Chiroptical spectroscopy and sugar amino acid systems', ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, Washington, DC (2005)

Patent (2 outputs)

Year Citation Altmetrics Link
2012 Selwood D, Simone M, et al, GUANIDINO-SUBSTITUTED BI-AND POLYPHENYLS AS SMALL MOLECULE CARRIERS (2012)
2010 Selwood D, Rebstock A-S, Simone M, Gooding M, Stoeber K, Tudzarova S, et al., New Compounds (2010)
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Research Supervision

Number of supervisions

Completed0
Current3

Total current UON EFTSL

PhD1.7

Current Supervision

Commenced Level of Study Research Title / Program / Supervisor Type
2015 PhD Applications of Flow Chemistry to the Synthesis of Novel Classes of Iminosugars
Chemical Sciences, Faculty of Science and Information Technology, The University of Newcastle
Principal Supervisor
2014 PhD Novel Classes of Iminosugars as Glycosidase Inhibitors via a Flow Chemistry Approach
Chemical Sciences, Faculty of Science and Information Technology, The University of Newcastle
Principal Supervisor
2011 PhD Synthesis of Bolinaquinone Analogues as Clathrin Inhibitors
Chemical Sciences, Faculty of Science and Information Technology, The University of Newcastle
Co-Supervisor
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Research Collaborations

The map is a representation of a researchers co-authorship with collaborators across the globe. The map displays the number of publications against a country, where there is at least one co-author based in that country. Data is sourced from the University of Newcastle research publication management system (NURO) and may not fully represent the authors complete body of work.

Country Count of Publications
United Kingdom 32
Australia 10
Italy 3
Belgium 2
Japan 2
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News

Italian PM meets UON Staff at a post-G20 function

UON staff meet Italian PM

December 9, 2014

A number of UON staff met Italy's Prime Minister at a post-G20 function in Sydney in November.

Dr Michela Simone

Position

Lecturer
School of Environmental and Life Sciences
Faculty of Science and Information Technology

Contact Details

Email michela.simone@newcastle.edu.au
Phone (02) 4985 4037
Fax (02) 4921 5361

Office

Room C324
Building Chemistry
Location Callaghan
University Drive
Callaghan, NSW 2308
Australia
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