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

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

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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@article{0104b374b7fe48ac9102f229fc269f5b,

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",

month = oct,

doi = "10.1093/carcin/13.10.1909",

language = "English (US)",

volume = "13",

pages = "1909--1911",

journal = "Carcinogenesis",

issn = "0143-3334",

publisher = "Oxford University Press",

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TY - JOUR

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.

UR - https://www.scopus.com/pages/publications/0026644786

UR - https://www.scopus.com/pages/publications/0026644786#tab=citedBy

U2 - 10.1093/carcin/13.10.1909

DO - 10.1093/carcin/13.10.1909

M3 - Article

C2 - 1423852

AN - SCOPUS:0026644786

SN - 0143-3334

VL - 13

SP - 1909

EP - 1911

JO - Carcinogenesis

JF - Carcinogenesis

IS - 10

ER -

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

Abstract

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