Synthesis, characterization, and 32p-postlabeling analysis of DNA adducts derived from the environmental contaminant 3-nitrobenzanthrone.

@article{Osborne2005SynthesisCA,
  title={Synthesis, characterization, and 32p-postlabeling analysis of DNA adducts derived from the environmental contaminant 3-nitrobenzanthrone.},
  author={Martin R. Osborne and Volker Manfred Arlt and Christian Kliem and William E. Hull and Amin Mirza and Christian A. Bieler and Heinz H. Schmeiser and David H. Phillips},
  journal={Chemical research in toxicology},
  year={2005},
  volume={18 6},
  pages={
          1056-70
        }
}
3-Nitrobenzanthrone (3-NBA) is a potent mutagen and potential human carcinogen identified in diesel exhaust and ambient air particulate matter. 3-NBA forms DNA adducts in rodent tissues that arise principally through reduction to N-hydroxy-3-aminobenzanthrone (N-OH-ABA), esterification to its acetate or sulfate ester, and reaction of this activated ester with DNA. We detected 3-NBA-derived DNA adducts in rodent tissues by (32)P-postlabeling and generated them chemically by acid-catalyzed… 
Structural identification of DNA adducts derived from 3-nitrobenzanthrone, a potent carcinogen present in the atmosphere.
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
Theoretical investigations on the formation of nitrobenzanthrone-DNA adducts.
TLDR
2-nitrobenzanthrone, an isomer of 3-NBA, was also included in the calculations; it has a higher abundance in ambient air than 3- NBA, but a much lower genotoxic potency.
Quantification of 3-nitrobenzanthrone-DNA adducts using online column-switching HPLC-electrospray tandem mass spectrometry.
TLDR
The mass spectrometric method developed is a faster, more automated analytical approach that also provides structural confirmation of the adducts detected by (32)P-postlabeling, and it has sufficient sensitivity and precision to analyze DNAAdducts in animals exposed to 3-NBA or its hydroxylamine metabolite.
S-(3-Aminobenzanthron-2-yl)cysteine in the globin of rats as a novel type of adduct and possible biomarker of exposure to 3-nitrobenzanthrone, a potent environmental carcinogen
TLDR
3-ABA-Cys is the first example of arylnitrenium-cysteine adduct in globin representing a new promising class of biomarkers to assess cumulative exposures to aromatic amines, nitroaromatics and heteroaromatic amines.
Mechanisms of Enzyme-Catalyzed Reduction of Two Carcinogenic Nitro-Aromatics, 3-Nitrobenzanthrone and Aristolochic Acid I: Experimental and Theoretical Approaches
TLDR
It is demonstrated that a combination of experimental and theoretical approaches is a useful tool to study the enzyme-mediated reaction mechanisms of 3-NBA and AAI reduction.
Erratum to: S-(3-Aminobenzanthron-2-yl)cysteine in the globin of rats as a novel type of adduct and possible biomarker of exposure to 3-nitrobenzanthrone, a potent environmental carcinogen
TLDR
A novel type of cysteine adduct, 3-aminobenzanthron-2-ylcysteine (3-ABA-Cys), confirmed using a synthesised standard is identified and is of great concern as a potent carcinogen as shown by a dose-dependent tumour formation reported in rats after intratracheal instillation.
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