We describe the design and synthesis of degradable, dual-release, pro-antimicrobial poly(thioether acetal) networks derived from synergistic pairs of aromatic terpene aldehydes. Initially, we identified pairs of aromatic terpene aldehydes derivatives exhibiting synergistic antimicrobial activity against <i>Pseudomonas</i> <i>aeruginosa</i> by determining fractional inhibitory concentrations. Synergistic aldehydes were converted into dialkene acetal monomers and copolymerized at various ratios with a multifunctional thiol via thiol-ene photopolymerization. The step-growth nature of the thiol-ene polymerization ensures every crosslink junction contains a degradable acetal linkage enabling a fully crosslinked polymer network to revert into its small molecule constituents upon hydrolysis, releasing the synergistic aldehydes as active antimicrobial compounds. Using a transposon mutagenesis assay, we show that these aldehydes target porins and multidrug efflux pumps.

Using aldehyde synergism to direct the design of degradable pro-antimicrobial polymer networks

2019 Spring National Meeting

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.