Antibiotic-resistant bacterial infections motivate the search for unconventional antibacterial strategies. A leading approach has been the development of synthetic polymers that mimic the structure and activity of naturally-occuring host defense peptides. We recently introduced a new class of antibacterial polymers with "self-immolative" characteristics, that is, the polymers can be triggered to induce spontaneously end-to-end depolymerization in repsonse to designed chemical, physical, or enzymatic stimuli. In contrast to standard biodegradable polymers, which are degraded by cleavage of sites along the backbone, self-immolative polymers (SIMPs) are inert in the absence of the triggering agent but unzip rapidly in a chain reaction when actiavated at the terminal chain end. In this talk, we report our recent progress on the development of antibacterial and non-toxic SIMPs. Specifically, poly(benzyl ether)s bearing allyl side chain and silyl ether end group were functionalized via thiol-ene click reactions to impart varying degrees of cationic charge, hydrophobicity, hydrophilicity, and cross-linking into network gels. By judicious tuning of the cationic charge and hydrophobicity, potent antibacterial SIMPs with minimal toxicity to red blood cells are accessible. The SIMPs undergo chain unzipping upon exposure to fluoride, into small molecules that are also antibacterial and relatively nontoxic. We are developing new surface coating materials based on these polymers that exhibit the ability to both kill bacteria on contact as well as to mechanical shed or delaminate accumulated biomass from the surface in a specifically triggered manner.

Self-immolative antibacterial polymers

256th National Meeting (2018)

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