芳烃代谢模型中自由基阳离子的形成。

Formation of radical cations in a model for the metabolism of aromatic hydrocarbons.

作者信息

Lehner Andreas F, Horn Jamie, Flesher James W

机构信息

Experimental Cancer Research Laboratory, Department of Veterinary Science, University of Kentucky, Lexington, KY 40536, USA.

出版信息

Biochem Biophys Res Commun. 2004 Sep 24;322(3):1018-23. doi: 10.1016/j.bbrc.2004.08.017.

DOI:10.1016/j.bbrc.2004.08.017

PMID:15336566

Abstract

To test the hypothesis that electrophilic radical cations are the major ultimate electrophilic and carcinogenic forms of benz[a]anthracene (BA), dibenz[a,h]anthracene (DBA), and benzo[a]pyrene (BP), we have focused on a chemical model of metabolism which parallels and duplicates known or potential metabolites of some polycyclic hydrocarbons formed in cells. Studies of this model system show that radical cations are hardly formed, if at all, in the case of BA or DBA but are definitely formed in the cases of the carcinogen BP as well as the non-carcinogenic hydrocarbons, pyrene and perylene. We conclude that the carcinogenicities of BA, DBA, BP, pyrene, and perylene are independent of one-electron oxidation to radical cation intermediates.

摘要

为了验证亲电自由基阳离子是苯并[a]蒽（BA）、二苯并[a,h]蒽（DBA）和苯并[a]芘（BP）的主要最终亲电及致癌形式这一假设，我们着重研究了一种代谢化学模型，该模型与细胞中某些多环烃已知的或潜在的代谢产物相似且重复。对这个模型系统的研究表明，在BA或DBA的情况下，几乎不会形成自由基阳离子（即便形成也极少），但在致癌物质BP以及非致癌烃芘和苝的情况下，肯定会形成自由基阳离子。我们得出结论，BA、DBA、BP、芘和苝的致癌性与单电子氧化形成自由基阳离子中间体无关。