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Oxidant‐Dependent REDOX Responsiveness of Polysulfides
Author(s) -
Carampin Paolo,
Lallana Enrique,
Laliturai Jureerat,
Carroccio Sabrina C.,
Puglisi Concetto,
Tirelli Nicola
Publication year - 2012
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201200264
Subject(s) - depolymerization , chemistry , oxidizing agent , hydrogen peroxide , macromolecule , redox , sulfoxide , hypochlorite , sodium hypochlorite , sulfide , polymer chemistry , toxicity , photochemistry , organic chemistry , biochemistry
Poly(propylene sulfide) (PPS) is studied as an oxidation‐responsive macromolecular building block, in the perspective of anti‐inflammatory 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 inflammatory 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 fibroblasts); 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.