DNA and protein modification and disturbance on cell system with NO produced from photo-reactivation of N-nitrosated amino acids

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The N-nitroso moiety of N-dialkylnitrosamines absorbs UVA photons, UVA-photolysis of N-dialkylnitrosamines brings release of nitric oxide, and subsequent production of alkyl radical cations and active oxygen species follow as secondary events, which cause DNA strand breaks, oxidative and alkylative DNA damages and mutation.Photoproducts from NPRO and dA were isolated, analyzed by MS and NMR, and identified as deoxyinosine and(R)-,(S)-2-(2-pyrrolidyl)-2'-deoxyadenosine. When UV light of 365 nm was irradiated to a neutral mixture of N-nitrosoproline, gluthathione and tyrosine, S-nitrosoglutathione and 3-nitrotyrosine were generated. These results suggest that N-nitrosoproline may induce nitrosation and nitration of cellular components in humans with sunlight.