Piggott, Matthew - University of Western Australia - School of Chemistry and Biochemistry

研究领域

Synthetic Organic Chemistry, Medicinal Chemistry and Chemical Biology I love designing and synthesising new compounds. Sometimes this is done with a practical application in mind; for example, with the aim of discovering new drugs (medicinal chemistry), to study complex biological systems (chemical biology), or as molecular components of electronic circuits or machines. Sometimes, strategy and methodology are the focus: how can we make a complex, biologically active natural product as efficiently as possible? And, sometimes, the driving force is about pushing the boundaries. We can design molecules with unprecedented, beautiful structures – can we make them? In all cases, the creativity and logic of organic synthesis is immensely intellectually rewarding. Very brief overviews of current research areas are outlined below. Parkinson’s disease medicinal chemistry: We have several projects investigating novel approaches to the pharmacotherapy of Parkinson’s disease, facilitated through a long-standing collaboration with Parkinson’s disease expert Dr Jonathan Brotchie, from the University Health Network, Toronto, Canada. The lead compound for one of these projects was the illicit drug MDMA (‘ecstasy’). Trypanosomiasis medicinal chemistry: Trypanosomiasis includes African sleeping sickness and Chagas disease, major neglected diseases of the third world. This work involves a multipronged international collaboration with Professor Jonathan Baell at the Monash Institute of Pharmaceutical sciences, Melbourne; Professor Vicky Avery at the Eskitis Institute, Griffith University, Brisbane; and GlaxoSmithKline, through the Tres Cantos Open Lab Foundation. Chemical Biology: Efforts in this area include the synthesis of stable analogues of phosphohistidine for the purpose of antibody generation, and histidine phosphatase/kinase inhibitor identification, in collaboration with Professor Paul Attwood from UWA; the design and synthesis of fluorescent probes of enzyme activity; and biological probes for the interrogation of protein oxidation state with Professor Peter Arthur from UWA. Total synthesis of natural products: Our group has achieved the novel total synthesis of 11 biologically-active natural products. Additional synthetic work has refuted several structures assigned to natural products. Design and synthesis of compounds with novel aromatic architectures: Through collaboration with UWA Professors George Koutsantonis and Paul Low, we are currently investigating the synthesis of novel organometallic complexes with potential applications as molecular switches. For more details on any of these areas of research (see also "Current Projects"), please email Matthew.

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Newson, H.L., Wild, D.A., Yeung, S.Y., Skelton, B.W., Flematti, G.R., Allan, J.E., Piggott, M.J. 2016, 'Access to 1,2,3,4-Tetraoxygenated Benzenes via a Double Baeyer-Villiger Reaction of Quinizarin Dimethyl Ether: Application to the Synthesis of Bioactive Natural Products from Antrodia camphorata', Journal of Organic Chemistry, 81, 8, pp. 3127-3135. Detail Walkey, M.C., Byrne, L.T., Piggott, M.J., Low, P.J., Koutsantonis, G.A. 2015, 'Enhanced bi-stability in a ruthenium alkynyl spiropyran complex', Dalton Transactions, 44, 19, pp. 8812-8815. Detail Punch, K.A., Piggott, M.J. 2014, 'Total synthesis of monosporascone and dihydromonosporascone', Organic and Biomolecular Chemistry, 12, 17, pp. 2801-2810. Detail Buccini, M., Piggott, M.J. 2014, 'A four-step total synthesis of radermachol', Organic Letters, 16, 9, pp. 2490-2493. Detail Buccini, M., Punch, K.A., Kaskow, B.J., Flematti, G.R., Skelton, B.W., Abraham, L.J., Piggott, M.J. 2014, 'Ethynylbenzenoid metabolites of Antrodia camphorata: Synthesis and inhibition of TNF expression', Organic and Biomolecular Chemistry, 12, 7, pp. 1100-1113. Detail Huot, P., Johnston, T.H., Lewis, K.D., Koprich, J.B., Reyes, M.G., Fox, S.H., Piggott, M.J., Brotchie, J.M. 2014, 'UWA-121, a mixed dopamine and serotonin re-uptake inhibitor, enhances l-DOPA anti-parkinsonian action without worsening dyskinesia or psychosis-like behaviours in the MPTP-lesioned common marmoset', Neuropharmacology, 82, pp. 76-87. Detail Buccini, M., Jeow, S.Y., Byrne, L., Skelton, B.W., Nguyen, T.M., Chai, C.L.L., Piggott, M.J. 2013, 'Bisannulation of 2,3-Dichloro-1,4-naphthoquinone with o-Nitrophenylacetic Acid Derivatives: A Succinct Synthesis of the ABCD Ring System of Alpkinidine', European Journal of Organic Chemistry, 2013, pp. 3232-3240. Detail Mukai, S, Flematti, G.R, Byrne, L.T, Besant, P.G, Attwood, P.V, Piggott, M.J 2012, 'Stable triazolylphosphonate analogues of phosphohistidine', AMINO ACIDS, 22 November 2011, pp. 18pp. Detail Johnston, T.H., Millar, Z., Huot, P., Wagg, K., Thiele, S., Salomonczyk, D., Yong-Kee, C.J., Gandy, M.N., McIldowie, M., Lewis, K.D., Gomez-Ramirez, J., Lee, J., Fox, S.H., Martin-Iverson, M., Nash, J.E., Piggott, M.J., Brotchie, J.M. 2012, 'A novel MDMA analogue, UWA-101, that lacks psychoactivity and cytotoxicity, enhances L-DOPA benefit in parkinsonian primates', FASEB JOURNAL, 26, pp. 2154-2163. Detail Wasik, A.M., Gandy, M.N., McIldowie, M., Holder, M.J., Chamba, A., Challa, A., Lewis, K.D., Young, S.P., Scheel-Toellner, D., Dyer, M.J., Barnes, N.M., Piggott, M.J., Gordon, J. 2012, 'Enhancing the anti-lymphoma potential of 3,4-methylenedioxymethamphetamine ('ecstasy') through iterative chemical redesign: mechanisms and pathways to cell death', INVESTIGATIONAL NEW DRUGS, 30, pp. 1471-1483. Detail Huot, P., Johnston, T.H., Gandy, M.N., Reyes, M.G., Fox, S.H., Piggott, M.J., Brotchie, J.M. 2012, 'The Monoamine Re-Uptake Inhibitor UWA-101 Improves Motor Fluctuations in the MPTP-Lesioned Common Marmoset', PLoS ONE, 7, 9, pp. 1-7. Detail ATTWOOD, P.V., BESANT, P.G., PIGGOTT, M.J. 2011, 'Focus on phosphoaspartate and phosphoglutamate', Amino Acids, 40, pp. 1035-1051. Detail Flematti, G.R., Merritt, D.J., Piggott, M.J., Trengove, R.D., Smith, S.M., Dixon, K.W., Ghisalberti, E.L. 2011, 'Burning vegetation produces cyanohydrins that liberate cyanide and stimulate seed germination', NATURE COMMUNICATIONS, 2, pp. 6pp. Detail Huot, P., Johnston, T.H., Lewis, K.D., Koprich, J.B., Reyes, M.G., Fox, S.H., Piggott, M.J., Brotchie, J.M. 2011, 'Characterization of 3,4-Methylenedioxymethamphetamine (MDMA) Enantiomers In Vitro and in the MPTP-Lesioned Primate: R-MDMA Reduces Severity of Dyskinesia, Whereas S-MDMA Extends Duration of ON-Time', JOURNAL OF NEUROSCIENCE, 31, pp. 7190-7198. Detail Punch, K.A., Ghisalberti, E.L., Piggott, M.J. 2011, 'Is 2,3,4,5-Tetramethoxybenzoyl Chloride a Natural Product?', JOURNAL OF NATURAL PRODUCTS, 74, pp. 1348–1350. Detail MCILDOWIE, M., GANDY, M.N., SKELTON, B.W., BROTCHIE, J.M., KOUTSANTONIS, G.A., SPACKMAN, M.A., PIGGOTT, M.J. 2010, 'Physical and Crystallographic Characterisation of the mGlu5 Antagonist MTEP and Its Monohydrochloride', Journal of Pharmaceutical Sciences, 99, pp. 234-245. Detail JOHNSTON, T.H., FOX, S.H., MCILDOWIE, M., PIGGOTT, M.J., BROTCHIE, J.M. 2010, 'Reduction of L-DOPA-induced dyskinesia by the selective metabotropic glutamate receptor 5 antagonist 3-[(2-methyl-1,3-thiazol-4-yl)ethynyl]pyridine in the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-lesioned macaque model of Parkinson's disease', The Journal of Pharmacology and Experimental Therapeutics, 333, 3, pp. 865-873. Detail GANDY, M.N., MCILDOWIE, M., LEWIS, K., WASIK, A.M., SALOMONCZYK, D., WAGG, K., MILLAR, Z.A., TINDIGLIA, D., HUOT, P., JOHNSTON, T., THIELE, S., NGUYEN, B., BARNES, N.M., BROTCHIE, J.M., MARTIN-IVERSON, M.T., NASH, J., GORDON, J., PIGGOTT, M.J. 2010, 'Redesigning the designer drug ecstasy: non-psychoactive MDMA analogues exhibiting Burkitt's lymphoma cytotoxicity', MEDCHEMCOMM, 1, 4, pp. 287-293. Detail JOHNSTON, T.H., FOX, S.H., PIGGOTT, M.J., SAVOLA, J., BROTCHIE, J.M. 2010, 'The _a2 Adrenergic Antagonist Fipamezole Improves Quality of Levodopa Action in Parkinsonian Primates', Movement Disorders, 25, 13, pp. 2084-2093. Detail WATERS, F.J., SHAVLAKADZE, T., MCILDOWIE, M.J., PIGGOTT, M.J., GROUNDS, M.D. 2010, 'Use of pifithrin to inhibit p53-mediated signalling of TNF in dystrophic muscles of mdx mice', Molecular and Cellular Biochemistry: an international journal for chemical biology in health and disease, 337, pp. 119-131. Detail