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Elsevier, Free Radical Biology and Medicine, 2(34), p. 196-206, 2003

DOI: 10.1016/s0891-5849(02)01194-2

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Nonradical mechanism of (bi)sulfite reaction with DEPMPO: Cautionary note for SO3-· radical spin trapping

This paper is available in a repository.
This paper is available in a repository.

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Abstract

Knowledge of the formation of radicals from sulfites, in vivo, is of interest in understanding the allergic and inflammatory responses to environmental sulfur dioxide exposure. Sulfite anion trioxide (SO(3)(-*)) radical formation was measured in mice, preloaded with the spin trap, 5-(diethoxy-phosphoryl)-5-methyl-pyrrolidine-N-oxide, (DEPMPO). Based on spin trapping NMR, a surprising quantity of reduced SO(3)(-*)-adduct was observed that did not depend on co-administration of oxidizing agents, suggesting a possible nonradical reaction between (bi)sulfite and DEPMPO. The products of the reversible nucleophylic addition of (bi)sulfite to the nitrone functional group were identified using (31)P-NMR, (1)H-NMR, and (13)C-NMR spectroscopy as cis- and trans- stereoisomers of hydroxylamine and confirmed by quantum chemical calculations. Oxidation of the hydroxylamines results in the formation of two corresponding cis- and trans-isomeric nitroxides, only one of which has been earlier described as the paramagnetic adduct of genuinely trapped SO(3)(-*) radical. The results demonstrate that SO(3)(-*) detection using nitrone spin traps such as DEPMPO and DMPO may involve nonradical addition reactions except in cases when the required controls unambiguously prove a radical mechanism.