Alkyl Chloride-Functionalized Polymers Mediate Oxidation of Thioethers Initiated by Ionizing Radiation.

Abstract

Irradiation of aqueous solutions containing alkyl chlorides generates peroxyl radicals by reactions of alkyl chlorides, aqueous electrons, and dissolved oxygen. The peroxyl radical can oxidize thioethers to sulfoxides, a transformation that has relevance for targeted or triggered drug delivery. However, small-molecule alkyl chlorides can induce liver damage, which limits their potential for application in anticancer therapy. Here, we show that alkyl chlorides bound to a hydrophilic random copolymer chain behave similar to small-molecule alkyl chlorides. Our work shows that using polymeric alkyl chlorides can be an alternative to small-molecule alkyl chlorides provided that the alkyl chloride functionalities are easily accessible to aqueous electrons.