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Guanylated Polymethacrylates: A Class of Potent Antimicrobial Polymers with Low Hemolytic Activity

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CSIRO Materials Science and Engineering, Bayview Avenue, Clayton, Victoria 3168, Australia
§ Ian Wark Research Institute, University of South Australia, Mawson Lakes, South Australia 5095, Australia
Mawson Institute, University of South Australia, Mawson Lakes, South Australia 5095, Australia
Sansom Institute, School of Pharmacy and Medical Sciences, University of South Australia, City East, South Australia 5000, Australia
# Department of Biochemistry and Molecular Biology, Monash University, Clayton, Victoria, Australia
Cite this: Biomacromolecules 2013, 14, 11, 4021–4031
Publication Date (Web):October 7, 2013
https://doi.org/10.1021/bm401128r
Copyright © 2013 American Chemical Society

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    Abstract

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    We have synthesized a series of copolymers containing both positively charged (amine, guanidine) and hydrophobic side chains (amphiphilic antimicrobial peptide mimics). To investigate the structure–activity relationships of these polymers, low polydispersity polymethacrylates of varying but uniform molecular weight and composition were synthesized, using a reversible addition–fragmentation chain transfer (RAFT) approach. In a facile second reaction, pendant amine groups were converted to guanidines, allowing for direct comparison of cation structure on activity and toxicity. The guanidine copolymers were much more active against Staphylococcus epidermidis and Candida albicans compared to the amine analogues. Activity against Staphylococcus epidermidis in the presence of fetal bovine serum was only maintained for guanidine copolymers. Selectivity for bacterial over mammalian cells was assessed using hemolytic and hemagglutination toxicity assays. Guanidine copolymers of low to moderate molecular weight and hydrophobicity had high antimicrobial activity with low toxicity. Optimum properties appear to be a balance between charge density, hydrophobic character, and polymer chain length. In conclusion, a suite of guanidine copolymers has been identified that represent a new class of antimicrobial polymers with high potency and low toxicity.

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    Details of 1H NMR, FT-IR, and MALDI-ToF analysis and additional bacterial and toxicity testing are provided. This material is available free of charge via the Internet at http://pubs.acs.org.

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