Associate Professor Brent Raymond Copp

BSc(Hons-I), PhD (Canterbury)

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Associate Professor

Biography

  • PhD. University of Canterbury (1989, with Murray Munro and John Blunt)
  • Post-doctoral Research Fellow, Cornell University (1990, with Jon Clardy)
  • Post-doctoral Research Fellow, University of Utah (1990-1992, with Chris Ireland)
  • Xenova Ltd, England (1992-1993)
  • Visiting Research Associate Professor, University of Utah, July 1997-February 1998
  • Lecturer, Department of Chemistry, The University of Auckland, 1993-1998
  • Senior Lecturer, Department of Chemistry, The University of Auckland, 1999-2005.
  • Associate Professor, Department of Chemistry, The University of Auckland, 2006-present.

Research | Current

The Natural Products Research Group investigates New Zealand marine organisms as sources of new compounds with potential applications against human diseases including cancer, inflammation and infectious diseases such as tuberculosis and malaria. While bio-assay directed fractionation leads to the isolation of the biologically active constituents of an organism, we are also interested in the intellectual challenge of solving the structures of new natural products whether they exhibit biological activity or not. Exploitation of bioactive natural products requires access to comprehensive bioassays, for which we have collaborations with leading medical research groups targeting anti-inflammatory, antitumour, antitubercular and antimalarial agents.

In addition to natural products chemistry, the group also has a strong interest in the discovery and development of new classes of antituberculosis and antimalarial agents. These projects combine both aspects of natural product drug discovery as well as rational design and synthesis of new compounds.


Current projects

  • Natural products drug discovery
    Marine natural products, the secondary or non-primary metabolites produced by organisms that live in the sea, are of interest to us for two main reasons: as a source of new and unsual organic molecules and as a source of biologically active molecules that can act as templates for the development of new therapeutic agents. We target the isolation of natural products that have activity towards human cancer cell lines, neglected disease targets (Trypanosomiasis, Leishmaniasis, Malaria, Tuberculosis) and inflammatory processes. Bioassay guided fractionation allows the isolation of the biologically active natural products, while the challenge of their structure solution is typically achieved by extensive use of 2-dimensional NMR spectroscopy (including 1H-15N 2-D NMR data sets) and mass spectrometry.
  • Exploiting the potential of bioactive natural products
    Our pure compound screening projects have identified a number of New Zealand marine organism-sourced natural products that exhibit activity towards cancer and neglected diseases. In order to exploit these findings, we are preparing small libraries of molecules designed around our natural products. These libraries are then screened for biological activity with our collaborators leading to the identified of new analogues with enhanced activity. Several projects are available in this area.
  • Natural products as biological tools
    Whilst it is possible to isolate potently bioactive natural products, very few of these compounds will ever be of use as pharmaceuticals themselves due to undesirable pharmacokinetic or toxicity problems. Such natural products can still be of tremendous to help understand biological processes, acting as probes or tools for biological chemical studies. This project is currently focused on two families of cytotoxic marine alkaloids, the discorhabdins and the amphimedines. We aim to prepare fluorescently-tagged analogues, to allow cellular localisation studies to be performed, and biotinylated analogues to facilitate 'pull-down' affinity chromatography experiments.
  • Marine antifouling agents
    It is speculated that the roles played by some marine natural products are to ensure the lack of fouling overgrowth of the organism. Due to the growing need to develop more ecologically friendly marine antifouling paints, we are exploring the discovery and development of marine natural products that can be incorporated into paints.

Research group members

  • Dr A. Norrie Pearce: Research fellow.
  • Jiayi Wang: Doctoral candidate.
  • Michael Pullar: Doctoral candidate.
  • Hugo Fong: Doctoral candidate.
  • Melissa Cadelis: Doctoral candidate.
  • Jessica Fleming: Doctoral candidate.
  • Roy Lai: MSc candidate.
  • Gerry Tan: BSc (Hons) student.
  • Victoria de Guzman: BSc (Hons) student.
  • Narisa Phummarin: BSc (Hons) student.

Postgraduate supervision

The list of research topics above is not exclusive - please see me if you have interests in these fields.

Areas of expertise

  • Organic & Medicinal Chemistry

Selected publications and creative works (Research Outputs)

  • Tempone, A. G., Ferreira, D. D., Lima, M. L., Costa Silva, T. A., Borborema, S. E. T., Reimão JQ, ... Wynne, G. M. (2017). Efficacy of a series of alpha-pyrone derivatives against Leishmania (L.) infantum and Trypanosoma cruzi. European journal of medicinal chemistry, 139, 947-960. 10.1016/j.ejmech.2017.08.055
    Other University of Auckland co-authors: Melissa Cadelis
  • Pearce, A. N., Kaiser, M., & Copp, B. R. (2017). Synthesis and antimalarial evaluation of artesunate-polyamine and trioxolane-polyamine conjugates. European journal of medicinal chemistry, 140, 595-603. 10.1016/j.ejmech.2017.09.040
  • Davidson, S. J., Pearce, A. N., Copp, B. R., & Barker, D. (2017). Total Synthesis of (-)-Bicubebin A, B, (+)-Bicubebin C and Structural Reassignment of (-)-cis-Cubebin. Organic letters10.1021/acs.orglett.7b02644
    Other University of Auckland co-authors: David Barker, Norrie Pearce, Sam Davidson
  • Cadelis, M. M., Bourguet-Kondracki, M.-L., Dubois, J., Kaiser, M., Brunel, J. M., Barker, D., & Copp, B. R. (2017). Structure-activity relationship studies on thiaplidiaquinones A and B as novel inhibitors of Plasmodium falciparum and farnesyltransferase. Bioorganic and Medicinal Chemistry, 25 (16), 4433-4443. 10.1016/j.bmc.2017.06.029
    Other University of Auckland co-authors: Melissa Cadelis, David Barker
  • Fong, H. K. H., Brunel, J. M., Longeon, A., Bourguet-Kondracki, M.-L., Barker, D., & Copp, B. R. (2017). Synthesis and biological evaluation of the ascidian blood-pigment halocyamine A. Organic and Biomolecular Chemistry, 15 (29), 6194-6204. 10.1039/c7ob01122a
    Other University of Auckland co-authors: David Barker
  • Lam, C. F. C., Cadelis, M. M., & Copp, B. R. (2017). Exploration of the influence of spiro-dienone moiety on biological activity of the cytotoxic marine alkaloid discorhabdin P. Tetrahedron, 73 (32), 4779-4785. 10.1016/j.tet.2017.06.057
    Other University of Auckland co-authors: Melissa Cadelis
  • Blunt, J. W., Copp, B. R., Keyzers, R. A., Munro, M. H. G., & Prinsep, M. R. (2017). Marine natural products. Natural Product Reports, 34 (3), 235-294. 10.1039/c6np00124f
    URL: http://hdl.handle.net/2292/35127
  • Cadelis, M. M., Khalil, I. M., Harper, J. L., Shaw, L., Dubois, J., Valentin, A., ... Copp, B. R. (2016). Structure-activity relationships of bioactive marine natural products leading to the identification of more potent non-natural analogues – the meroterpenoids, thiaplidiaquinones A and B. Planta Medica. 10.1055/s-0036-1596124
    Other University of Auckland co-authors: David Barker, Melissa Cadelis

Identifiers

Contact details

Primary location

SCIENCE CENTRE - CHEMISTRY - Bldg 301
Level 6, Room 629A
23 SYMONDS ST
AUCKLAND 1010
New Zealand

Web links