Self-immolative polymers are macromolecules that undergo a specifically triggered end-to-end depolymerization process in response to cleavage of a single bond at the omega end of the polymer chain. This spontenaous unzipping is due to the low ceiling temperature of the polymerization/depolymerization equilibrium. But lowering the temperature, the uzipped monomers can be re-polymerized and end capped again, thus opening the door to dynmaically reconfigurable polymers and polymer networks. In our lab, we are pursuing fucntionalization of such polymers by side chain modification to introduce biological activity. Specifically, conjugation of PEG and cationic group side chains endows water solubility and broad-spectrum bactericidal activity in addition to the stimuli responsive nature of the polymer backbone. We have synthesized a library of such self-immolative polycations and screened their activity against bactera cells as well as their toxicity to red blood cells. In this presentation, we will show how the structure-activity relationships are optimized to give antibacterial polymers capable of unzipping into biologically inactive small molecules.

Antimicrobial self-immolative polymers

254th National Meeting (2017)

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