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- W2015219317 abstract "Aromatic amines constitute one of the most extensively studied classes of chemical carcinogens. Although monocyclic aromatic amines are generally regarded as weak carcinogens, a recent epidemiologic study of bladder cancer found that the arylamine 3,5-dimethylaniline (3,5-DMA) may play a significant role in the etiology of this disease in man. Investigations using experimental animals also strongly suggested that DNA adducts—of indeterminate structure—formed by 3,5-DMA might account for its presumptive activity. The present study was undertaken to determine the structures of the major DNA adducts formed in vitro by the known, and possibly carcinogenic, N-hydroxylated metabolite. Calf thymus DNA (ct-DNA) was modified by reaction with N-acetoxy-3,5-dimethylaniline (N-AcO-3,5-DMA). After enzymatic hydrolyzis of DNA to individual 2′-deoxyribonucleosides, adduct profiles were determined using HPLC/MS. 3,5-DMA formed four major DNA adducts, one to 2′-deoxyguanosine (dG), two to 2′-deoxyadenosine (dA), and one to 2′-deoxycytidine (dC). Reactions of N-AcO-3,5-DMA with dG, dA, and dC produced the same adducts as reaction with ct-DNA with very similar profiles. Adducts were isolated chromatographically and unambiguously characterized as N-(deoxyguanosin-8-yl)-3,5-dimethylaniline (dG-C8–3,5-DMA), 4-(deoxyadenosin-N6-yl)-3,5-dimethylaniline (dA-N6-3,5-DMA), N-(deoxyadenosin-8-yl)-3,5-dimethylaniline (dA-C8–3,5-DMA), and N-(deoxycytidin-5-yl)-3,5-dimethylaniline (dC-C5–3,5-DMA) by high-resolution mass spectra (HR-MS) and NMR spectroscopy including 1H NMR, 13C NMR, and two-dimensional NMR. This report includes the first detailed description of a dC adduct of an aromatic amine. The present results provide chemical support for a carcinogenic mechanism of action by 3,5-DMA based on N-hydroxylation and the intermediacy of a nitrenium ion in the formation of DNA adducts." @default.
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- W2015219317 date "2007-11-01" @default.
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- W2015219317 title "Identification of Adducts Formed by Reaction of <i>N</i>-Acetoxy-3,5-dimethylaniline with DNA" @default.
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- W2015219317 doi "https://doi.org/10.1021/tx700306c" @default.
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