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  • Title: Structural identification of DNA adducts derived from 3-nitrobenzanthrone, a potent carcinogen present in the atmosphere.
    Author: Takamura-Enya T, Kawanishi M, Yagi T, Hisamatsu Y.
    Journal: Chem Asian J; 2007 Sep 03; 2(9):1174-85. PubMed ID: 17712830.
    Abstract:
    3-Nitrobenzanthrone is a powerful bacterial mutagen and carcinogen to mammals. To obtain precise information on DNA-adduct formation by 3-nitrobenzanthrone, a number of DNA adducts, including N-(2'-deoxyguanosin-8-yl)-3-aminobenzanthrone (13 a), 2-(2'-deoxyguanosin-N2-yl)-3-aminobenzanthrone (14 a), N-(2'-deoxyadenosin-8-yl)-3-aminobenzanthrone (15 a), 2-(2'-deoxyadenosin-N6-yl)-3-aminobenzanthrone (16 a), and their N-acetylated counterparts 13 b, 14 b, 15 b, and 16 b were synthesized by palladium-catalyzed aryl amination of the corresponding nucleoside and bromobenzanthrone derivatives. Among these DNA adducts, DNA adducts 13 a, 13 b, 14 a, 14 b, and 16 a were identified in the reaction mixture of nucleosides (2'-deoxyguanosine, 2'-deoxyadenosine, or DNA) with N-acetoxy-3-aminobenzanthrone or N-acetyl-N-acetoxy-3-aminobenzanthrone, both of which are recognized as activated metabolites of 3-nitrobenzanthrone. The formation of these multiple DNA adducts may help explain the potent mutacarcinogenicity of 3-nitrobenzanthrone.
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