New DNA adducts of crotonaldehyde and acetaldehyde

被引:71
作者
Hecht, SS [1 ]
McIntee, EJ [1 ]
Wang, MY [1 ]
机构
[1] Univ Minnesota, Ctr Canc, Minneapolis, MN 55455 USA
关键词
acetaldehyde; aldoxane; crotonaldehyde; DNA adducts; paraldol;
D O I
10.1016/S0300-483X(01)00436-X
中图分类号
R9 [药学];
学科分类号
1007 ;
摘要
This paper summarizes our recent studies on adducts produced in the reactions of the carcinogens crotonaldehyde (2-butenal) and acetaldehyde with deoxyguanosine (dG) and DNA. Human exposure to these carcinogens can be considerable, from both exogenous and endogenous sources. Crotonaldehyde reacts with DNA to form Michael addition products, a pathway that has been well described. We describe a second major pathway, in which 3-hydroxybutanal, formed by addition of H(2)O to crotonaldehyde, reacts with DNA to produce the Schiff base N(2)-(3-hydroxbut-1-ylidene)dG as well as several diastercomers of N(2)-paraldol-dG. Acetaldehyde reacts with DNA and dG giving a major Schiff base adduc, N(2)-ethylidene-dG. A cross-linked adduct of acetadehyde has been characterized for the first time, and other adducts resulting from the reaction of two and three molecules of acetaldehyde with dG have been observed. The results of these studies demonstrate that some structurally unique adducts are formed from these carcinogenic aldehydes and suggest some new directions for research on the potential role of aldehydes in human cancer. (C) 2001 Elsevier Science Ireland Ltd. All rights reserved.
引用
收藏
页码:31 / 36
页数:6
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