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 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.
Rogan
E G
EG
Eppley Institute for Research in Cancer, University of Nebraska Medical Center, Omaha 68198-6805.
RamaKrishna
N V
NV
Higginbotham
S
S
Cavalieri
E L
EL
Jeong
H
H
Jankowiak
R
R
Small
G J
GJ
D000818:Animals; D001564:Benzo(a)pyrene / Q000032:analysis* / Q000378:metabolism*; D002274:Carcinogens, Environmental / Q000032:analysis* / Q000652:urine; D004247:DNA / Q000032:analysis* / Q000378:metabolism / Q000652:urine; D018736:DNA Adducts; D005243:Feces / Q000737:chemistry*; D006147:Guanine / Q000378:metabolism*; D051381:Rats; D011919:Rats, Inbred Strains
D002274:Carcinogens, Environmental; D018736:DNA Adducts; C056612:benzo(a)pyrene-DNA adduct; D001564:Benzo(a)pyrene; D006147:Guanine; D004247:DNA