Degradation of Peroxynitrite by Simple, Recyclable Selenolanes

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Abstract

<jats:title>Abstract</jats:title> <jats:p>Two cyclic organoselenium compounds, DHS (trans-3,4-dihydroxy-1-selenolane) and MAS (3-amino-1-selenolane) were examined for their reaction with peroxynitrite. Both DHS and MAS scavenge peroxynitrite with rate constants of the order of 103 M−1 s−1. Additionally the two compounds efficiently react with carbonate (CO3•−) radical (formed by reaction of peroxynitrite with carbon dioxide) by one-electron oxidation and their selenoxides convert the nitrite formed by peroxynitrite reduction to nitrate. Even though the reactivity of DHS/MAS was fairly the same with peroxynitrite and its derived radicals, they differ in their ability to protect plasmid pBR322 DNA and CHO cells from peroxynitrite induced toxicity. To understand this, analysis of crucial products formed during peroxynitrite reaction was carried out. On reaction with peroxynitrite, both the compounds were converted to their corresponding selenoxide, identified and estimated by NMR and HPLC. Comparing the relative yields of the selenoxides, it has been confirmed that DHS produced significantly higher amount of selenoxide than MAS. The selenoxide can be regenerated back to the parent compound, either by thiols or by nitrite. Based on these results it is concluded that formation of stable and recyclable selenoxide makes selenolanes, a novel class of selenium compounds as antioxidants for peroxynitrite degradation.</jats:p>

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