NDLI: RAFT-derived antimicrobial polymethacrylates: elucidating the impact of end-groups on activity and cytotoxicity

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RAFT-derived antimicrobial polymethacrylates: elucidating the impact of end-groups on activity and cytotoxicity

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Polymer Chemistry Vol - 5 Issue - 9

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RAFT-derived antimicrobial polymethacrylates: elucidating the impact of end-groups on activity and cytotoxicity

Content Provider	Royal Society of Chemistry (RSC)
Author	Locock, Katherine E. S. Meagher, Laurence Griesser, Hans J. Hayball, John D. Stevens, Natalie Emilia Traven, Ana Qu, Yue Haeussler, Matthias Vasilev, Krasimir Michl, Thomas D. Postma, Almar
Copyright Year	2014
Abstract	Antimicrobial polymers as mimics of natural antimicrobial peptides are emerging as an alternative to classic antibiotics due to their potency, selectivity and lower susceptibility to resistance. The key chemical aspects necessary to confer high activity and selectivity to the polymer chain composition are largely known. However, little attention has been paid to how end-groups affect the overall biological activity. Here we report the use of RAFT polymerization to obtain eight well-defined cationic methacrylate polymers which bear either amine (PA1–4) or guanidine (PG1–4) pendant groups, while systematically varying the R- and Z-RAFT end-groups. These polymers were assessed in haemotoxicity assays as well as antimicrobial testing against clinically relevant pathogens; such as a vigorously biofilm forming strain of Staphylococcus epidermidis (S. epidermidis) and a vancomycin and methicillin resistant strain of Staphylococcus aureus (VISA) as well as the opportunistic fungus Candida albicans (C. albicans). The R-group was found to dominate the measured toxicity of polymers. Replacement of the anionic cyanovaleric acid R-group (PA1) with the neutral isobutyronitrile (PA3) led to over a 20 fold increase in the haemolytic activity of the polymers. The Z-group, however, was found to have more influence on the antimicrobial activity of the polymers against both VISA and C. albicans, whereby polymers with a long, lipophilic dodecylsulfanyl Z-group (PA1) were found to be more potent than those with either an ethylsulfanyl or no ZCS2-group. These results indicate that chemical control over the end-groups is a key element for achieving the desired high biological activity and selectivity, particularly when low molecular weights are required for maximum antibacterial activity.
Starting Page	5813
Ending Page	5822
Page Count	10
File Format	HTM / HTML PDF
ISSN	17599954
Volume Number	5
Issue Number	19
Journal	Polymer Chemistry
DOI	10.1039/c4py00652f
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Antimicrobial Candida albicans Hemolysis Guanidine Polymerization Polymer Vancomycin Methicillin Staphylococcus epidermidis Aureus Carboxylic acid Methicillin-resistant Staphylococcus aureus Z-group Biofilm Lipophilicity
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Bioengineering Biomedical Engineering Polymers and Plastics

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RAFT-derived antimicrobial polymethacrylates: elucidating the impact of end-groups on activity and cytotoxicity

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RAFT-derived antimicrobial polymethacrylates: elucidating the impact of end-groups on activity and cytotoxicity