Antimicrobial agents that are dispersed throughout a polymeric network traditionally suffer from unwanted leaching, low loading, and uncontrolled burst release. In this work, we describe the synthesis of new acetal containing monomers derived from intrinsically antimicrobial compounds. Upon polymerization, these active agents are fully incorporated within a stable thiol-ene network. However, exposure to aqueous environments results in rapid degradation and release of the antibiotic in its active form. Herein, we demonstrate the synthesis of a library of monomers, photopolymerization kinetics, degradation kinetics, and antimicrobial evaluation of both the monomers and their films. We then incorporate this network chemistry into highly monodisperse microparticles to evaluate antimicrobial activity. The antimicrobial activity is shown to increase with increasing concentration of the acetal monomer for gram-positive (S. aureus) and gram-negative (E. coli, P. aeruginosa and B. cenocepacia) bacteria. This thiol-ene system represents a new approach for tailoring the release of antimicrobial agents from crosslinked polymeric microparticles.

Pro-Antimicrobial Networks with Degradable Acetals (PANDAs) prepared via thiol-ene photopolymerization

253rd National Meeting (2017)

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