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Dr Michela Simone


Contact Details

D.Phil (Oxon), M.R.S.C.
Lecturer in Chemistry
Room 412a
School of Chemistry, Building F11
The University of Sydney, NSW, 2006, Australia
E: michela.simone@sydney.edu.au
T: +61 2 9351 2830
F: +61 2 9351 3329

Career Profile

  • 2010-Current - Lecturer in Chemistry at University of Sydney
  • 2010- Post-Doctoral Fellow at University of Oxford, Oxford, U.K
  • 2009 - Member of the Royal Society of Chemistry
  • 2007-2010 - Post-Doctoral Fellow at University College London, London, U.K
  • 2002-2006 - D.Phil. University of Oxford (The Queen’s College), Oxford, U.K. – E.U. European Research Training Network award
  • 2000-2001 - Academic year at the Georg-August Universitaet Goettingen. – E.U. Socrates award
  • 1998-2002 - MSc (Hons I), The Victoria University of Manchester, Manchester, U.K.

Areas of Interest

  • Carbohydrate chemistry
  • Chemical biology
  • Foldamers
  • Supramolecular chemistry
  • Bioinorganic and medicinal chemistry

Research

The ongoing research projects in the group are highly multi-disciplinary and draw together the fields of organic synthesis, carbohydrate chemistry, medicinal chemistry, supramolecular chemistry and chemical biology in novel and exciting ways.

Transient fluorescent labeling of proteins in vivo

The fluorescent tagging of proteins 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 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 foldameric structures which are engineered to transiently and selectively bind to protein surfaces.

Novel materials from carbohydrate building blocks

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 have recently been utilised in the synthesis of many classes of compounds: analogues of biologically important molecules (e.g. imino sugars), peptidomimetics, foldamers and natural products. We are expanding the uses and scope of carbohydrate building blocks in the synthesis of novel polymeric materials to be utilised in biomedical applications.

Novel classes of bioinorganic anti-cancer agents

We have also recently established a collaboration with the Hambley group and are working on the synthesis and biological evaluation of novel classes of Pt- and Co-based anticancer agents.

If you are interested in doing your Hons year, a Ph.D. or a Post-Doc with us, contact me on michela.simone@sydney.edu.au

 

Publications (2005 to 2012)

  1. Soengas, RG; Simone, M; Hunter, S; Nash, RJ and 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, (12), 2394-2402, 2012. DOI: 10.1002/ejoc.201200054

  2. Simone,MI*; Soengas, RG; Jenkinson, SF; Evinson, EL; Nash, RJ and 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. Tetrahedran: Asymmetry, 23 (5), 401-408, 2012. DOI: 10.1016/j.tetasy.2012.03.007

  3. Dube, H; Selwood, D; Malouitre, S; Capano, M; Simone, MI and 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. DOI: 10.1042/BJ20111301.

  4. Gooding, M; Tudzarova, S; Kingsbury, SR; Rebstock, A-S and Simone, M; et al. Exploring the interaction between siRNA and the SMoC biomolecule transporters: Implications for small molecule-mediated delivery of siRNA. Chemical Biology and Drug Design, 79 (1), 9-21, 2012. DOI: 10.1111/j.1747-0285.2011.01249.x

  5. Simone, MI; Edwards, AA; Tranter, GE and 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 – Special Issue on Foldamers, 41 (3), 643-661, 2011. DOI: 10.1007/s00726-011-0849-7

  6. Simone, M; Edwards, AA; Tranter, GE and Fleet, GWJ. Carbon branched delta-tetrahydrofuran sugar amino acids (SAAs) as dipeptide isostere scaffolds. Tetrahedron: Asymm.,19, 2887-2894, 2008.. Special issue on sugar amino acids.

  7. Risseeuw, MDP; Overhand, M; Fleet, GWJ and Simone, M. A compendium of sugar amino acids (SAA): scaffolds, peptide- and glyco-mimetics. Tetrahedron: Asymm., 18 (17), 2001-2010, 2007. Review. DOI: 10.1016/j.tetasy.2007.08.004

  8. Jockusch, RA; Talbot, FO; Rogers, PS; Simone, M; Fleet, GWJ and Simons, JP. Carbohydrate amino acids: The intrinsic conformational preference for a β-turn-type, structure in a carbopeptoid building block. J. Am. Chem. Soc., 128 (51), 16771-16777, 2006. DOI: 10.1021/ja0607133

  9. Bleriot, Y; Simone, M; Wormald, MR; Dwek, RA, Watkin, DJ and Fleet, GWJ. Sugar amino acids at the anomeric position of carbohydrates: Synthesis of spirocyclic amino acids of 6-deoxy-L-lyxofuranose. Tetrahedron: Asymm., 17 (15), 2276-2286, 2006. DOI: 10.1016/j.tetasy.2006.07.027

  10. Simone, M; Soengas, R; Newton, CR; Watkin, DJ and Fleet, GWJ. Branched tetrahydrofuran α,α-disubstituted-δ-sugar amino acid scaffolds from branched sugar lactones: a new family of foldamers? Tetrahedron Lett., 46 (34), 5761-5765, 2005. DOI: 10.1016/j.tetlet.2005.06.029

  11. Soengas, R; Izumori, K; Simone, M; Watkin, DJ; Skytte, UP; Soetaert, W and Fllet, GWJ. Kiliani reactions on ketoses: branched carbohydrate building blocks from D-tagatose and D-psicose. Tetrahedron Lett., 46 (34), 5755-5759, 2005. DOI: 10.1016/j.tetlet.2005.06.030

Structural Reports (2004 to 2012)

  1. Jenkinson, SF; Thompson, AL and Michela Simone*. Methyl 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-4-nitrobenzoate. Acta Crystallographica Section E, E68 (8), o2429-o2430, 2012. DOI: 10.1107/S1600536812029650

  2. Jenkinson, SF; Thompson, AL and Michela Simone,*. Methyl 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-4-nitrobenzoate. Acta Crystallographica Section E, E68, o2429-o2430, 2012. DOI: 10.1107/S1600536812029650

  3. Michela Simone,* Edwards, AA; Cowley, AR; Fleet, GWJ and Watkin, DJ. (3R,4R,5R)-5-(Acetamidomethyl)-N-benzyl-3,4-dihydroxytetrahydrofuran-3-carboxamide. Acta Crystallographica Section E, E66, o2750–o2751, 2010.  DOI:10.1107/S1600536810039589

  4. Michela Simone,* Edwards, AA; Parker, SG; Tranter, GE; Fleet, GWJ and 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, E66, o2699–o2700, 2010. DOI:10.1107/S1600536810038559

  5. Michela Simone,* Fleet, GWJ; Bream, R and Watkin, DJ. 5-Amino-5-deoxy-2-C-hydroxymethyl-2,3-O-isopropylidene-L-lyxono-1,5-lactam. Acta Crystallographica Section E, E63, o1409-o1411, 2007. DOI:10.1107/S1600536807007568

  6. Michela Simone,* Fleet, GWJ and Watkin, DJ. 5-O-tert-Butyldiphenylsilyl-2-C-hydroxymethyl-2,3-O-isopropylidene-2C-O-trifluoromethanesulfonyl-D-ribono-1,4-lactone. Acta Crystallographica Section E, E63, o1088-o1090, 2007. DOI:10.1107/S1600536807004436

  7. Michela Simone,* Fleet, GWJ and Watkin, DJ. 1,5-Anhydro-2,3-O-isopropylidene-L-lyxofuranose. Acta Crystallographica Section E, E63, o896-o897, 2007. DOI:10.1107/S160053680700311X

  8. Michela Simone,* Fleet, GWJ and Watkin, DJ. 3,3’:5,6-Di-O-isopropylidene-3-C-hydroxy-methyl-D-allono-1,4-lactone. Acta Crystallographica Section E, E63, o799-o801, 2007. DOI:10.1107/S1600536807002061

  9. Punzo, F; Cowley, AR; Watkin, DJ; Michela Simone, Edwards, AA; Tranter, GE and Fleet, GWJ. Pentafluorophenyl (3R,4R,5R)-5-{[(3R,4R,5R)-5-azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carbonylamino]methyl}-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate. Acta Crystallographica Section E, E62, o473-o475, 2006. DOI: 10.1107/S1600536805043205

  10. Parker, SG; Watkin, DJ; Michela Simone and Fleet, GWJ. 3,4:5,6-Di-O-isopropylidene-3-C-hydroxymethyl-D-altrono-1,3'-lactone. Acta Crystallographica Section E, E62, o3961-o3963, 2006. DOI:10.1107/S1600536806015881

  11. Punzo, F; Watkin, DJ; Michela Simone and Fleet, GWJ. (3R,4R,5S)-5-(Acetamidomethyl)-N-benzyl-3,4-dihydroxytetrahydrofuran-3-carboxamide. Acta Crystallographica Section E, E61, o513-o515, 2005. DOI:10.1107/S1600536805001467

  12. Punzo, F; Watkin, DJ; Michela Simone and Fleet, GWJ. (1R,5S,8R)-1,8-Dihydroxy-6-oxa-3-azabicyclo[3.2.1]octan-2-one. Acta Crystallographica Section E, E60, o2315-o2317, 2004. DOI:10.1107/S1600536804028983

  13. Cowley, AR; Fleet, GWJ; Michela Simone, Soengas, R. 3-O-tert-Butyldimethylsilyl-2,2':5,6-di-O-isopropylidene-2-C-hydroxymethyl-D-glucono-1,4-lactone. Acta Crystallographica Section E, E60, o2142-o2143, 2004. DOI:10.1107/S1600536804025310

  14. van Ameijde, j; Cowley, AR; Fleet, GWJ; Nash, RJ; Michela Simone and Soengas, R. 5-Amino-5-deoxy-2-C-hydroxymethyl-2,3-O-isopropylidene-D-talono-1,5-lactam. Acta Crystallographica Section E, E60, o2140-o2141, 2004. DOI:10.1107/S1600536804025292

  15. Watkin, DJ; Mueller, M; Blériot, Y; Michela Simone and 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, E60, o1820-o1822, 2004. DOI:10.1107/S1600536804022494

  16. Newton, CR; Michela Simone, Fleet, GWJ; Blériot, Y and Watkin, DJ. 2-C-Hydroxymethyl-2,3-O-isopropylidene-D-ribono-1,5-lactam. Acta Crystallographica Section E, E60, o909-o910, 2004. DOI:10.1107/S1600536804008141


Patents

  1. Guanidino-substituted bi- and polyphenyls as small molecule carriers. Pub. No.: WO/2010/097604; International Application No.: PCT/GB2010/000359; Publication Date: 02.09.2010; International Filing Date: 01.03.2010.


In the News

2012

 

Dr Michela Simone and Mr Jack Reed, Honours student 2013

“The Simone Group”. Jack Reed – Hons Student.