Our Research
Our group investigates synthetic organic chemistry, including the total synthesis of complex, biologically active natural products, the development of stereoselective synthetic methodology, and the synthesis of compounds with potential therapeutic value. Research in the group involves: (i) the development of new and general synthetic methodologies with particular emphasis on efficiency and selectivity; (ii) application of these methods to the synthesis of complex, biologically active natural products, and; (iii) design and synthesis of natural product analogues as potential therapeutic agents. Applications include:
Molecular probes for pancreatic cancer
Pancreatic cancer is the most deadly human cancer and remains a major challenge for global healthcare. Worldwide, over 600,000 people die from pancreatic cancers each year with an overall 5-year survival rate of less than 5%. Despite improvements in treatment of other cancers, the outlook for pancreatic cancer has not improved in over 3 decades. Natural products, such as angelmarin and lasonolide A, have historically proved to be excellent lead compounds in drug discovery. We are developing compounds based on natural products to fight pancreatic cancer cells in collaboration with the Garvan Institute, NSW and National Cancer Center, Japan.
Environmentally sustainable asymmetric synthesis: chiral hydrogen bonding organocatalysts
Asymmetric organocatalysis by chiral hydrogen-bond donors is emerging as a key method of synthesis. This project aims to design, synthesise and evaluate novel chiral hydrogen-bond donor compounds as potential organocatalysts. These compounds have several potential advantages over current catalysts, including their ready preparation, ease of handling, broad functional group tolerance and low environmental impact.
Flexible approaches to natural product synthesis enable the preparation of synthetic analogues with potentially improved properties, and for use as molecular probes to improve our understanding of mechanisms of action.
- Assoc Prof Mark Coster
Study Opportunities
Available student projects:
- Environmentally sustainable asymmetric synthesis
- A concise and unified new strategy for the synthesis of spirocycles
- Pancreatic cancer drugs - mechanism of action investigation
- Molecular probes for pancreatic cancer
- Libraries inspired by natural products
20 Recent Publications
- Aumann, K. M.; Hungerford, N. L.; Coster, M. J. First enantioselective synthesis of methyl (+)-7-methoxyanodendroate, an antitubercular dihydrobenzofuran. Tetrahedron Lett. 2011, 52, 6988-6990.
- Banwell, M.G.; Coster, M. J.; Hungerford, N. L.; Garson, M. J.; Su, S.; Kotze, A. C.; Munro, M. H. G. 3,4'-Linked bis(piperidines) related to the haliclonacyclamine class of marine alkaloids: synthesis using crossed-aldol chemistry and preliminary biological evaluations. Org. Biomol. Chem. 2011, Advance Article (Accepted 22 Sep 2011). http://dx.doi.org/10.1039/C1OB06418E
- Rohlena, J.; Dong, L.-F.; Kluckova, K.; Zobalova, R.; Goodwin, J.; Tilly, D.; Stursa, J.; Pecinova, A.; Philimonenko, A.; Hozak, P.; Banerjee, J.; Ledvina, M.; Sen, C. K.; Houstek, J.; Coster, M. J.; Neuzil, J. Mitochondrially targeted α-tocopheryl succinate is antiangiogenic: Potential benefit against tumor angiogenesis but caution against wound healing. Antioxidants & Redox Signaling 2011, 15, 2923-2935.
- Fischer, J.; Savage, G. P.; Coster, M. J. A Concise Route to Dihydrobenzo[b]furans: Formal Total Synthesis of (+)-Lithospermic Acid. Org. Lett. 2011, 13, 3376–3379.
- Dong, L.-F.; Jameson, V. J. A.; Tilly, D.; Prochazka, L.; Rohlena, J.; Valis, K.; Truksa, J.; Zobalova, R.; Mahdavian, E.; Kluckova, K.; Stantic, M.; Stursa, J.; Freeman, R.; Witting, P. K.; Norberg, E.; Goodwin, J.; Salvatore, B. A.; Novotna, J.; Turanek, J.; Ledvina, M.; Hozak, P.; Zhivotovsky, B.; Coster, M. J.; Ralph, S. J.; Smith, R. A. J.; Neuzil, J. Mitochondrial targeting of α-tocopheryl succinate enhances its pro-apoptotic efficacy: A new paradigm of efficient cancer therapy. Free Radical and Biology Medicine 2011, 50, 1546-1555.
- Aumann, K. M.; Healy, P. C.; Coster, M. J. Arylation of [6,6]-spiroacetal enol ethers: reactivity and rearrangement. Tetrahedron Lett. 2011, 52, 1070-1073.
- Dong, L.-F.; Jameson, V. J. A.; Tilly, D.; Cerny, J.; Mahdavian, E.; Marin-Hernandez, A.; Hernandez-Esquivel, L.; Rodriguez-Enriquez, S.; Stursa, J.; Witting, P. K.; Stantic, B.; Rohlena, J.; Truksa, J.; Kluckova, K.; Dyason, F. C.; Ledvina, M.; Salvatore, B. A.; Moreno-Sanchez, R.; Coster, M. J.; Ralph, S. J.; Smith, R. A. J.; Neuzil, J. Mitochondrial targeting of vitamin E succinate enhances its pro-apoptotic and anti-cancer activity. J. Biol. Chem. 2011, 286, 3717-3728.
- Magolan, J.; Coster, M. J. Targeting the resistance of pancreatic cancer cells to nutrient deprivation: anti-austerity compounds. Current Drug Deliv. 2010, 7, 355-369.
- Banister, S. D.; Moussa, I. A.; Jordan, M. J. T.; Coster, M. J.; Kassiou, M. Oxo-bridged isomers of aza-trishomocubane sigma (σ) receptor ligands: synthesis, binding, and molecular modelling. Bioorg. Med. Chem. Lett. 2010, 20, 145-148.
- Magolan, J.; Coster, M. J. Total Synthesis of (+)-Angelmarin. J. Org. Chem. 2009, 74, 5083-5086.
- Gunosewoyo, H; Coster, MJ; Bennett, MR; Kassiou, M. Purinergic P2X7 receptor antagonists: Chemistry and Fundamentals of Biological Screening. Bioorg. Med. Chem. 2009, 17, 4861-4865.
- Truong, L.; Allbutt, H. N.; Coster, M. J.; Kassiou, M.; Henderson, J.M. Behavioural effects of a selective NMDA NR1A/2B receptor antagonist in rats with unilateral 6-OHDA + parafascicular lesions. Brain Research Bulletin 2009, 78, 91-96.
- Warraich, S. T.; Allbutt, H. N.; Billing, R.; Radford, J.; Coster, M. J.; Kassiou, M.; Henderson, J.M. Evaluation of behavioural effects of a selective NMDA NR1A/2B receptor antagonist in the unilateral 6-OHDA lesion rat model. Brain Research Bulletin 2009, 78, 85-90.
- Dolle, F.; Langle, S.; Roger, G.; Fulton, R. R.; Lagnel-de Bruin, B.; Henderson, D. J.; Hinnen, F.; Paine, T.; Coster, M. J.; Valette, H.; Bottlaender, M.; Kassiou, M. Synthesis and In-Vivo Evaluation of [11C]p-PVP-MEMA as a PET Radioligand for Imaging Nicotinic Receptors. Aust. J. Chem. 2008, 61, 438-445.
- Gunosewoyo, H.; Guo, J. L.; Bennett, M. R.; Coster, M. J.; Kassiou, M. Cubyl amides: Novel P2X7 receptor antagonists. Bioorg. Med. Chem. Lett. 2008, 18, 3720-3723.
- Cergol, K. M.; Coster, M. J. Asymmetric aldol reaction using boron enolates. Nature Protocols 2007, 2, 2568-2573.
- Gunosewoyo, H.; Coster, M. J.; Kassiou, M. Molecular Probes for P2X7 Receptor Studies.Curr. Med. Chem. 2007, 14, 1505-1523.
- Liu, X.; Banister, S. D.; Christie, M. J.; Banati, R.; Meikle, S.; Coster, M. J.; Kassiou, M. Trishomocubanes: Novel s ligands modulate cocaine-induced behavioral effects. European Journal of Pharmacology 2007, 555, 37-42.
- Cergol, K. M.; Jensen, P.; Turner, P.; Coster, M. J. Reversibility in the boron-mediated ketone-ketone aldol reaction. Chemical Communications (Cambridge, United Kingdom) 2007, 1363-1365.
- Banister, S. D.; Clegg, J. K.; Coster, M. J.; Jolliffe, K. A.; Kassiou, M. (1R,2S,3R,6S,7R,8S)-Tricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-diol. Acta Crystallographica, Section E: Structure Reports Online 2007, E63, o92-o93.
Research staff
- Associate Professor Mark Coster (Research Member)
- Ms Melissa Barnier (PhD Student)
- Dr Natasha Hungerford (Research Fellow)
- Ms Samantha James (PhD Student)
- Mr Adam Pigott (PhD Student)
- Dr Jan Stursa (Research Fellow)