Characterization of 2'-Deoxycytidine Adducts Derived from 4-Oxo-2-nonenal, a Novel Lipid Peroxidation Product
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- 作者：Michael Pollack ; Tomoyuki Oe ; Seon Hwa Lee ; Maria Victoria Silva Elipe ; Byron H. Arison ; and Ian A. Blair
- 刊名：Chemical Research in Toxicology
- 出版年：2003
- 出版时间：July 2003
- 年：2003
- 卷：16
- 期：7
- 页码：893 - 900
- 全文大小：189K
- 年卷期：v.16,no.7(July 2003)
- ISSN：1520-5010
文摘
Analysis of the reaction between 2'-deoxycytidine and 4-oxo-2-nonenal by LC/MS revealedthe presence of three major products (adducts A1, A2, and B; [M + H]+ = 364). Adducts A1 andA2 were isomeric, and each dehydrated to form adduct B. The structure of adduct B was shownby LC/MS and NMR spectroscopy to be an etheno-2'-deoxycytidine adduct 1' '-[1-(2'-deoxy-
-D-erythro-pentofuranosyl)-1H-imidazo[2,1-c]pyrimidin-2-oxo-4-yl]heptane-2' '-one. A time courseexperiment performed at 65 
C (pH 5-8) showed that the transformation of both A1 and A2was pH-dependent. In acidic conditions, adducts A1 and A2 dehydrated primarily to adduct B.In contrast, in basic conditions, adducts A1 and A2 hydrolyzed primarily to dCyd. The data areconsistent with adducts A1 and A2 being substituted ethano adducts that dehydrate to adductB, a substituted 3,N4-etheno-2'-deoxycytidine adduct.
-D-erythro-pentofuranosyl)-1H-imidazo[2,1-c]pyrimidin-2-oxo-4-yl]heptane-2' '-one. A time courseexperiment performed at 65 C (pH 5-8) showed that the transformation of both A1 and A2was pH-dependent. In acidic conditions, adducts A1 and A2 dehydrated primarily to adduct B.In contrast, in basic conditions, adducts A1 and A2 hydrolyzed primarily to dCyd. The data areconsistent with adducts A1 and A2 being substituted ethano adducts that dehydrate to adductB, a substituted 3,N4-etheno-2'-deoxycytidine adduct.