Formation of 7-(4-oxobutyl)guanine in hepatic dna of rats treated with n-nitrosopyrrolidine

Mingyao Wang; Fung Lung Chung; Stephen S. Hecht

doi:10.1093/carcin/13.10.1909

Formation of 7-(4-oxobutyl)guanine in hepatic dna of rats treated with n-nitrosopyrrolidine

Mingyao Wang, Fung Lung Chung, Stephen S. Hecht

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Abstract

We have reported previously the formation of two structurally distinct exocyclic guanine adducts (adducts 1 and 6) in liver DNA of F344 rats treated with N-nitrosopyrrolidine (NPYR). In this study, we detected and characterized a previously unidentified guanine adduct in liver DNA of NPYR-treated rats. The structure of this adduct was established as 7-(4-oxobutyl)guanine (adduct 2) by comparison with the synthetic standard and confirmed by NaBH₄ reduction to 7-(4-hydroxybutyl)guanine. The level of adduct 2 in liver DNA of F344 rats treated with 450 mg/kg of NPYR by i.p. administration was 643 ± 9 μmol/mol guanine, approximately one-third of the level of adduct 1. This study is the first to demonstrate the in vivo formation of a formylalkyl-substituted guanine adduct by a nitrosamine.

Original language	English (US)
Pages (from-to)	1909-1911
Number of pages	3
Journal	Carcinogenesis
Volume	13
Issue number	10
DOIs	https://doi.org/10.1093/carcin/13.10.1909
State	Published - Oct 1992
Externally published	Yes

Bibliographical note

Funding Information:
This work was supported by grants CA-44377 and CA-51830 from the National Cancer Institute. This is paper no. 145 in 'A Study of Chemical Carcinogenesis'.

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10.1093/carcin/13.10.1909

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title = "Formation of 7-(4-oxobutyl)guanine in hepatic dna of rats treated with n-nitrosopyrrolidine",

abstract = "We have reported previously the formation of two structurally distinct exocyclic guanine adducts (adducts 1 and 6) in liver DNA of F344 rats treated with N-nitrosopyrrolidine (NPYR). In this study, we detected and characterized a previously unidentified guanine adduct in liver DNA of NPYR-treated rats. The structure of this adduct was established as 7-(4-oxobutyl)guanine (adduct 2) by comparison with the synthetic standard and confirmed by NaBH4 reduction to 7-(4-hydroxybutyl)guanine. The level of adduct 2 in liver DNA of F344 rats treated with 450 mg/kg of NPYR by i.p. administration was 643 ± 9 μmol/mol guanine, approximately one-third of the level of adduct 1. This study is the first to demonstrate the in vivo formation of a formylalkyl-substituted guanine adduct by a nitrosamine.",

author = "Mingyao Wang and Chung, {Fung Lung} and Hecht, {Stephen S.}",

note = "Funding Information: This work was supported by grants CA-44377 and CA-51830 from the National Cancer Institute. This is paper no. 145 in 'A Study of Chemical Carcinogenesis'.",

year = "1992",

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doi = "10.1093/carcin/13.10.1909",

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T1 - Formation of 7-(4-oxobutyl)guanine in hepatic dna of rats treated with n-nitrosopyrrolidine

AU - Wang, Mingyao

AU - Chung, Fung Lung

AU - Hecht, Stephen S.

N1 - Funding Information: This work was supported by grants CA-44377 and CA-51830 from the National Cancer Institute. This is paper no. 145 in 'A Study of Chemical Carcinogenesis'.

PY - 1992/10

Y1 - 1992/10

N2 - We have reported previously the formation of two structurally distinct exocyclic guanine adducts (adducts 1 and 6) in liver DNA of F344 rats treated with N-nitrosopyrrolidine (NPYR). In this study, we detected and characterized a previously unidentified guanine adduct in liver DNA of NPYR-treated rats. The structure of this adduct was established as 7-(4-oxobutyl)guanine (adduct 2) by comparison with the synthetic standard and confirmed by NaBH4 reduction to 7-(4-hydroxybutyl)guanine. The level of adduct 2 in liver DNA of F344 rats treated with 450 mg/kg of NPYR by i.p. administration was 643 ± 9 μmol/mol guanine, approximately one-third of the level of adduct 1. This study is the first to demonstrate the in vivo formation of a formylalkyl-substituted guanine adduct by a nitrosamine.

AB - We have reported previously the formation of two structurally distinct exocyclic guanine adducts (adducts 1 and 6) in liver DNA of F344 rats treated with N-nitrosopyrrolidine (NPYR). In this study, we detected and characterized a previously unidentified guanine adduct in liver DNA of NPYR-treated rats. The structure of this adduct was established as 7-(4-oxobutyl)guanine (adduct 2) by comparison with the synthetic standard and confirmed by NaBH4 reduction to 7-(4-hydroxybutyl)guanine. The level of adduct 2 in liver DNA of F344 rats treated with 450 mg/kg of NPYR by i.p. administration was 643 ± 9 μmol/mol guanine, approximately one-third of the level of adduct 1. This study is the first to demonstrate the in vivo formation of a formylalkyl-substituted guanine adduct by a nitrosamine.

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JF - Carcinogenesis

IS - 10

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Formation of 7-(4-oxobutyl)guanine in hepatic dna of rats treated with n-nitrosopyrrolidine

Abstract

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