Identification and quantitation of 7-(benzo[a]pyren-6-yl)guanine in the urine and feces of rats treated with benzo[a]pyrene

The major identified benzo[a]pyrene (BP)-DNA adduct formed by cytochrome P-450 contains BP bound at the C-6 position to the N-7 position of guanine (BP-N7Gua). This adduct is rapidly depurinated from DNA. When rats were treated with [14C]BP, about 0.02% of the administered dose of BP was excreted as...

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Bibliographic Details
Published in:Chemical research in toxicology 1990-09, Vol.3 (5), p.441-444
Main Authors: Rogan, Eleanor G, RamaKrishna, N. V. S, Higginbotham, S, Cavalieri, Ercole L, Jeong, Hyuk, Jankowiak, Ryszard, Small, Gerald J
Format: Article
Language:English
Subjects:
Animals
Benzo(a)pyrene - analysis
Benzo(a)pyrene - metabolism
Carcinogens, Environmental - analysis
Carcinogens, Environmental - urine
DNA - analysis
DNA - metabolism
DNA - urine
DNA Adducts
Feces - chemistry
Guanine - metabolism
Rats
Rats, Inbred Strains
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Summary:The major identified benzo[a]pyrene (BP)-DNA adduct formed by cytochrome P-450 contains BP bound at the C-6 position to the N-7 position of guanine (BP-N7Gua). This adduct is rapidly depurinated from DNA. When rats were treated with [14C]BP, about 0.02% of the administered dose of BP was excreted as BP-N7Gua in feces and urine within 5 days. Chloroform extracts of the urine and feces were analyzed by high-pressure liquid chromatography. The structure of the adduct was established by cochromatography with electrochemically prepared BP-N7Gua and by fluorescence line narrowing spectrometry. This study represents the first demonstration that BP-N7Gua is formed in vivo in animals treated with BP.
ISSN:0893-228X
1520-5010
DOI:10.1021/tx00017a009