New Designer Biocides

D/Prof Margaret Brimble

Dr Zoran Zujovic

Inventing the future generation of antimicrobials

Developing new molecules using biodegradable linkers for reduced environmental impact, higher potency and slower release

Synthesis of New Cyclic Lipopeptide-Based Antimicrobial Agents

Lipopeptides are expressed by bacteria in nature in response to microbes competing for the same source of nutrients. Some of these have been exploited for its antimicrobial properties, such as the Iturins family of antifungals and the antibiotic Battacin.

Analogues of these lipopeptides can be chemically accessed with a technique called CLipPA, by using commercially available building blocks. These analogues will be put to the test against the pathogens to determine their efficacy as antimicrobial compounds. This will set the basis for facile access to lipopeptides and discovery of new biocides

Victor's research will be applicable in expediting the process of synthesizing antimicrobial agents.

PhD student Victor Yim

Victor received an MSc in chemistry at University of Auckland, and he is passionate about synthesis of peptides and following applications with antibiotics.

New Designer Bactericidal Polymers

Chloe’s project aims to design and synthesise high performance, low cost, colourless guanidine containing antimicrobial biodegradable polymers through various polymerisation techniques.

Chloe is supervised by Dr Jianyong Jin, and her project is composed of four major parts:

1. Design and Synthesis the novel guanidine monomer

2. Ring openning Polymerisation of guanidine cyclic monomers

3. Co-Polymerisation with other functional monomers

4. Evaluate and Analysis of guanidine containing polymers on antimicrobial potency, stability, biodegradation and cytotoxicity

A possible application for this enhanced compound is in antimicrobial handwash and liquid soaps, as it is also water soluble.

Chloe received a BS(Honors) in Chemistry at the University of Auckland. She is passionate about Organic, Polymer and Surface Chemistry

PhD student Chloe Cho

Short Peptides as Eco-Friendly Marine Anti-Fouling Agents

Developing new eco-friendly co-biocides that could help preventing the growth of micro and macroscopic organisms on submerged surfaces (marine biofouling).

These compounds will be incorporated in biocide-laced paints and should have characteristics such as biodegradability and absence of toxicity for the marine environment.

Lead compounds from the literature have been identified and our initial interest is focusing on micropeptides, based on truncated portions of Lactoferrin, that showed antibacterial properties at nM concentrations and that have been recently tested for antifouling assays on the macrofouler barnacle Balanus improvisus with good results.

PhD student Thomas Grant

Thomas received a BSc(Honors) in Medicinal Chemistry at the University of Auckland. He is passionate about synthetic chemistry and protecting the environment

Published Work

Brimble, M.A., Edwards P.J., Harris, P.W.R., Norris, G.E., Patchett, M.L., Wright, T.H., Yang, S.-H., Carley, S.E. (2015). Synthesis of the antimicrobial S-linked glycopeptide, Glycocin F. Chemistry – A European Journal 21: 3556-3561.

Jin J.; Cooney R.; Fu, Q., Qiao, G.G., Thomas, S., Merkel, T.C. (2015). Synthesis of perfectly alternating copolymers for polymers of intrinsic microporosity Polymer Chemistry 6(28): 5003-5008.

De Leon Rodriguez, L.M., Kaur, H., Brimble, M.A. (2016). Synthesis and bioactivity of antitubercular peptides and peptidomimetics: an update, Organic and Biomolecular Chemistry 14, 1177-1187.

De Leon Rodriguez, L.M., Weidkamp, A.J., Brimble, M.A. (2015). An update on new methods to synthesize cyclotetrapeptides, Organic and Biomolecular Chemistry 13: 6906-6921.

Dolan, C., Naysmith, B., Hinkley, S.F.R., Sims, I. M., Brimble, M.A., Williams, D.E., Jin, J. (2015). Synthesis of novel triazole-containing phosphonate polymers, Australian Journal of Chemistry 68: 680-686.

Harris, P.W.R., Squire, C., Young, P.G., Brimble, M.A. (2015). Chemical Synthesis of gamma-secretase activating protein using pseudo-glutamines as ligation sites, Biopolymers (Peptide Science) 104: 37-45.

Kamalov, M., Kaur, H., Brimble, M.A. (2016). Intermolecular peptide cross-linking by using diaminodicarboxylic acids. Chemistry - A European Journal 22: 3622-3631.

Kaur, H., Harris, P.W.R., Little P.J., Brimble, M.A. (2015). Total synthesis of the cyclic depsipeptide YM-280193, a platelet aggregation inhibitor, Organic Letters 17: 492-495.

Medini, K., Harris, P.W.R., Hards, K., Dingley, A.J.G., Cook, M., Brimble, M.A. (2015). Chemical synthesis of a pore-forming antimicrobial protein, Caenopore-5, by using native chemical ligation at a Glu-Cys site, ChemBioChem 16: 328-336.

Yang, S.-H., Harris, P.W.R., Williams, G.M., Brimble, M.A. (2016). Lipidation of Cysteine or Cysteine-Containing Peptides Using the Thiol-ene Reaction (CLipPA), European Journal of Organic Chemistry 33, 2608-2616.