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Mechanism of Nitric Oxide Release from S -Nitrosothiols *

Journal of Biological Chemistry, ISSN: 0021-9258, Vol: 271, Issue: 31, Page: 18596-18603
1996
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S -Nitrosothiols have many biological activities and have been suggested to be intermediates in signal transduction. The mechanism and products of S -nitrosothiol decomposition are of great significance to the understanding of nitric oxide (·NO) biochemistry. S -Nitrosothiols are stable compounds at 37°C and pH 7.4 in the presence of transition metal ion chelators. The presence of trace transition metal ions (present in all buffers) stimulates the catalytic breakdown of S -nitrosothiols to ·NO and disulfide. Thiyl radicals are not formed as intermediates in this process. Photolysis of S -nitrosothiols results in the formation of ·NO and disulfide via the intermediacy of thiyl radicals. Reduced metal ion ( e.g. Cu + ) decomposes S -nitrosothiols more rapidly than oxidized metal ion ( e.g. Cu 2+ ) indicating that reducing agents such as glutathione and ascorbate can stimulate decomposition of S -nitrosothiol by chemical reduction of contaminating transition metal ions. Transnitrosation can also stimulate S -nitrosothiol decomposition if the product S -nitrosothiol is more susceptible to transition metal ion-catalyzed decomposition than the parent S -nitrosothiol. Equilibrium constants for the transnitrosation reactions of reduced glutathione, either with S -nitroso- N -acetyl- DL -penicillamine or with S -nitroso- L -cysteine indicate that S -nitrosoglutathione formation is favored. The biological relevance of S -nitrosothiol decomposition is discussed.

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