Polymer chemistry has been dedicated to assemble small molecules together to construct long macromolecules. Interestingly, “self-immolative” polymers (SIMPs) just do the opposite. They are long chain macromolecules, which spontaneously unzip into monomers upon the cleavage of the stimuli-responsive endcaps. In contrast to conventional biodegradable polymers, SIMPs can undergo rapid and complete depolymerization only at specific sites within the backbone by specific triggering events (light, enzymes, pH change etc.), yet stay stable under normal operational conditions. This novel class of materials have been utilized in various applications including, biosensors, drug delivery, dynamic plastics, and microfluidics, but not as antimicrobials until very recently. Our group developed the first example of a self-immolative polymer that exerts potent antibacterial activity coupled with relatively low hemolytic toxicity. Self-immolative poly(benzyl ether)s bearing pendant cationic ammonium groups and grafted poly(ethylene glycol) (either 800 or 2000 g/mol) in their side chains were prepared via post-polymerization photo-activated thiol–ene chemistry. The molar composition of the resulting statistical copolymers varied from 0 to 100% PEG side chains. Here, we demonstrate that systematic tuning of the PEG graft density and chain length is a highly effective strategy to modulate the polymer hydrophobicity and to enhance their cell-type selectivity. We envision that these materials may be useful in a broad range of antibacterial and anti-biofouling coatings with unique ‘‘triggered-cleaning’’ characteristics. <br/>

Self-immolative polymers with potent and selective antibacterial activity by hydrophilic side chain grafting

2019 Spring National Meeting

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