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

Eleanor G. Rogan; N. V.S. Ramakrishna; Sheila Higginbotham; Ercole L. Cavalieri; Hyuk Jeong; Ryszard Jankowiak; Gerald J. Small

doi:10.1021/tx00017a009

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

Eleanor G. Rogan, N. V.S. Ramakrishna, Sheila Higginbotham, Ercole L. Cavalieri, Hyuk Jeong, Ryszard Jankowiak, Gerald J. Small

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Abstract

The major identified benzo[o]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.

Original language	English (US)
Pages (from-to)	441-444
Number of pages	4
Journal	Chemical Research in Toxicology
Volume	3
Issue number	5
DOIs	https://doi.org/10.1021/tx00017a009
State	Published - 1990

ASJC Scopus subject areas

Toxicology

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

abstract = "The major identified benzo[o]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.",

author = "Rogan, {Eleanor G.} and Ramakrishna, {N. V.S.} and Sheila Higginbotham and Cavalieri, {Ercole L.} and Hyuk Jeong and Ryszard Jankowiak and Small, {Gerald J.}",

year = "1990",

doi = "10.1021/tx00017a009",

language = "English (US)",

volume = "3",

pages = "441--444",

journal = "Chemical Research in Toxicology",

issn = "0893-228X",

publisher = "American Chemical Society",

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T1 - Identification and quantitation of 7-(Benzo[a-]pyren-6-yl)guanine in the urine and feces of rats treated with benzo[a]pyrene

AU - Rogan, Eleanor G.

AU - Ramakrishna, N. V.S.

AU - Higginbotham, Sheila

AU - Cavalieri, Ercole L.

AU - Jeong, Hyuk

AU - Jankowiak, Ryszard

AU - Small, Gerald J.

PY - 1990

Y1 - 1990

N2 - The major identified benzo[o]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.

AB - The major identified benzo[o]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.

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DO - 10.1021/tx00017a009

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

Abstract

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