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Free‐Radical Degradation of High‐Molar‐Mass Hyaluronan Induced by Ascorbate plus Cupric Ions: Evaluation of Antioxidative Effect of Cysteine‐Derived Compounds
Author(s) -
Hrabárová Eva,
Valachová Katarína,
Juránek Ivo,
Šoltés Ladislav
Publication year - 2012
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201100046
Subject(s) - chemistry , cysteamine , glutathione , cysteine , thiol , hyaluronic acid , synovial joint , hydroxyl radical , reactive oxygen species , ascorbic acid , biochemistry , radical , enzyme , medicine , osteoarthritis , alternative medicine , food science , pathology , biology , genetics , articular cartilage
Based on our previous findings, the present study has focused on free‐radical‐mediated degradation of the synovial biopolymer hyaluronan. The degradation was induced in vitro by the Weissberger 's system comprising ascorbate plus cupric ions in the presence of oxygen, representing a model of the early phase of acute synovial joint inflammation. The study presents a novel strategy for hyaluronan protection against oxidative degradation with the use of cysteine‐derived compounds. In particular, the work objectives were to evaluate potential protective effects of reduced form of L ‐glutathione, L ‐cysteine, N ‐acetyl‐ L ‐cysteine, and cysteamine, against free‐oxygen‐radical‐mediated degradation of high‐molar‐mass hyaluronan in vitro. The hyaluronan degradation was influenced by variable activity of the tested thiol compounds, also in dependence of their concentration applied. It was found that L ‐glutathione exhibited the most significant protective and chain‐breaking antioxidative effect against the hyaluronan degradation. Thiol antioxidative activity, in general, can be influenced by many factors such as various molecule geometry, type of functional groups, radical attack accessibility, redox potential, thiol concentration and p K a , pH, ionic strength of solution, as well as different ability to interact with transition metals. Antioxidative activity was found to decrease in the following order: L ‐glutathione, cysteamine, N ‐acetyl‐ L ‐cysteine, and L ‐cysteine. These findings might be beneficial in future development of potential drugs in the treatment of synovial hyaluronan depletion‐derived diseases.