二苯并[a,e]荧蒽的体外代谢活化。其湾区和准湾区二醇环氧化物优先与鸟苷反应的证据。

The metabolic activation of dibenzo[a,e]fluoranthene in vitro. Evidence that its bay-region and pseudo-bay-region diol-epoxides react preferentially with guanosine.

作者信息

Perin-Roussel O, Croisy A, Ekert B, Zajdela F

出版信息

Cancer Lett. 1984 Apr;22(3):289-98. doi: 10.1016/0304-3835(84)90165-4.

Abstract

Dibenzo[a,e]fluoranthene ( DBF ), a non- alternant carcinogenic polycyclic aromatic hydrocarbon (PAH), binds covalently to DNA. The main adducts were characterized as covalent additions of its bay-region and pseudo-bay-region diol-epoxides. The structure of these 2 adducts was analyzed by mass spectrometry using their persilyl derivatives. 3,4-Dihydroxy-1,2-epoxy-1,2,3,4-tetrahydro- DBF (3,4-diol-1,2-epoxy- DBF ) and 12,13-dihydroxy-10,11-epoxy-10,11,12,13-tetrahydro- DBF (12, 13-diol-10,11-epoxy- DBF ) obtained by synthesis were allowed to react in vitro with calf thymus DNA or with poly(G). The comigration of DNA and poly(G) adducts isolated after acid hydrolysis of DNA and poly(G) was in good agreement with mass spectroscopic results: both bay-region and pseudo-bay-region DBF diol-epoxides reacted with guanine residues.

摘要

二苯并[a,e]荧蒽（DBF）是一种非交替型致癌多环芳烃（PAH），它能与DNA共价结合。主要加合物被鉴定为其湾区和准湾区二醇环氧化物的共价加成物。使用它们的全硅烷基衍生物通过质谱分析了这两种加合物的结构。通过合成得到的3,4 - 二羟基 - 1,2 - 环氧 - 1,2,3,4 - 四氢 - DBF（3,4 - 二醇 - 1,2 - 环氧 - DBF）和12,13 - 二羟基 - 10,11 - 环氧 - 10,11,12,13 - 四氢 - DBF（12,13 - 二醇 - 10,11 - 环氧 - DBF）在体外与小牛胸腺DNA或聚（G）反应。DNA和聚（G）经酸水解后分离得到的加合物的共迁移与质谱结果高度一致：湾区和准湾区DBF二醇环氧化物均与鸟嘌呤残基发生反应。