Oxidant-Dependent REDOX Responsiveness of Polysulfides

Authors

  • Paolo Carampin,

    1. School of Pharmacy and Pharmaceutical Sciences, University of Manchester, Oxford Road, Manchester, M13 9PT, United Kingdom
    Search for more papers by this author
  • Enrique Lallana,

    1. School of Materials, University of Manchester, Oxford Road, Manchester, M13 9PT, United Kingdom
    Search for more papers by this author
  • Jureerat Laliturai,

    1. School of Pharmacy and Pharmaceutical Sciences, University of Manchester, Oxford Road, Manchester, M13 9PT, United Kingdom
    Current affiliation:
    1. The Government Pharmaceutical Organization, 75/1 Rama 6 Road, Ratchathewi, Bangkok 10400, Thailand
    Search for more papers by this author
  • Sabrina C. Carroccio,

    1. Istituto di Chimica e Tecnologia dei Polimeri, UOS Catania, Consiglio Nazionale delle Ricerche, Via P. Gaifami 18, 95126 Catania, Italy
    Search for more papers by this author
  • Concetto Puglisi,

    1. Istituto di Chimica e Tecnologia dei Polimeri, UOS Catania, Consiglio Nazionale delle Ricerche, Via P. Gaifami 18, 95126 Catania, Italy
    Search for more papers by this author
  • Nicola Tirelli

    Corresponding author
    1. School of Materials, University of Manchester, Oxford Road, Manchester, M13 9PT, United Kingdom
    2. School of Biomedicine, University of Manchester, Oxford Road, Manchester, M13 9PT, United Kingdom
    • School of Materials, University of Manchester, Oxford Road, Manchester, M13 9PT, United Kingdom.
    Search for more papers by this author

Abstract

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 (H2O2) and hypochlorite (OCl), which are oxidizing species commonly encountered during inflammatory processes. It was found that the oxidation with H2O2 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.

Ancillary