Oxidant-Dependent REDOX Responsiveness of Polysulfides

Poly(propylene sulfi de) (PPS) is studied as an oxidation-responsive macromolecular building block, in the perspective of anti-infl ammatory therapies. Here, we show that the nature of the oxidant has profound effects on the outcome of the oxidation process. PPS was exposed to hydrogen peroxide (H 2 O 2 ) and hypochlorite (OCl - ), which are oxidizing species commonly encountered during infl ammatory processes. It was found that the oxidation with H 2 O 2 converted thioethers into sulfoxides, producing water-soluble macromolecular products with extremely low toxicity (L929 fi broblasts); on the contrary, the reaction with NaOCl produced sulfones in addition to sulfoxides, and this was accompanied by depolymerization, which appears to considerably affect the toxicity of the oxidation products.