A metabolite of the carcinogen 7,12-dimethylbenz[a]anthracene that reacts predominantly with adenine residues in DNA

Four 7,12-dimethylbenz[α]anthracene-deoxyribonucleoside adducts formed in mouse epidermis in vivo arise from the syn dihydrodiol epoxide metabolite of this carcinogen. With the synthetic syn dihydrodiol epoxide it was possible to identify three of these as deoxyadenosine adducts and to establish the...

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Bibliographic Details
Published in:Carcinogenesis (New York) 1988-09, Vol.9 (9), p.1721-1723
Main Authors: Cheng, S.C., Prakash, A.S., Pigott, M.A., Hilton, B.D., Lee, H., Harvey, R.G., Dipple, A.
Format: Article
Language:English
Subjects:
9,10-Dimethyl-1,2-benzanthracene - analogs & derivatives
9,10-Dimethyl-1,2-benzanthracene - metabolism
Adenine
Animals
Biological and medical sciences
Carcinogenesis, carcinogens and anticarcinogens
Chemical agents
Chromatography, High Pressure Liquid
Circular Dichroism
Deoxyadenosines - analogs & derivatives
DNA
Epidermis - metabolism
Epoxy Compounds
Magnetic Resonance Spectroscopy
Medical sciences
Mice
Tumors
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Summary:Four 7,12-dimethylbenz[α]anthracene-deoxyribonucleoside adducts formed in mouse epidermis in vivo arise from the syn dihydrodiol epoxide metabolite of this carcinogen. With the synthetic syn dihydrodiol epoxide it was possible to identify three of these as deoxyadenosine adducts and to establish their structures. These three adducts account for the large majority of DNA adduct arising from this metabolite in vivo. The in vivo metabolite is unusual, therefore, in that it reacts almost exclusively with adenine residues in DNA while most carcinogen metabolites react preferentially with guanine residues.
ISSN:0143-3334
1460-2180
DOI:10.1093/carcin/9.9.1721