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首页> 外文期刊>International Journal of Environmental Research and Public Health >Photochemical Reaction of 7,12-Dimethylbenz[a]anthracene (DMBA) and Formation of DNA Covalent Adducts
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Photochemical Reaction of 7,12-Dimethylbenz[a]anthracene (DMBA) and Formation of DNA Covalent Adducts

机译：7,12-二甲基苯并[a]蒽（DMBA）的光化学反应和DNA共价加合物的形成

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DMBA, 7,12-dimethylbenz[a]anthracene, is a widely studied polycyclic aromatic hydrocarbon that has long been recognized as a probable human carcinogen. It has been found that DMBA is phototoxic in bacteria as well as in animal or human cells and photomutagenic in Salmonella typhimurium strain TA102. This article tempts to explain the photochemistry and photomutagenicity mechanism. Light irradiation converts DMBA into several photoproducts including benz[a]anthracene-7,12-dione, 7-hydroxy-12-keto-7-methylbenz[a]anthracene, 7,12-epidioxy-7,12-dihydro-DMBA, 7-hydroxymethyl-12-methylbenz[a]anthracene and 12-hydroxymethyl-7-methylbenz[a]anthracene. Structures of these photoproducts have been identified by either comparison with authentic samples or by NMR/MS. At least four other photoproducts need to be assigned. Photo-irradiation of DMBA in the presence of calf thymus DNA was similarly conducted and light-induced DMBA-DNA adducts were analyzed by 32P-postlabeling/TLC, which indicates that multiple DNA adducts were formed. This indicates that formation of DNA adducts might be the source of photomutagenicity of DMBA. Metabolites obtained from the metabolism of DMBA by rat liver microsomes were reacted with calf thymus DNA and the resulting DNA adducts were analyzed by 32P-postlabeling/TLC under identical conditions. Comparison of the DNA adduct profiles indicates that the DNA adducts formed from photo-irradiation are different from the DNA adducts formed due to the reaction of DMBA metabolites with DNA. These results suggest that photo-irradiation of DMBA can lead to genotoxicity through activation pathways different from those by microsomal metabolism of DMBA.
机译：DMBA，7,12-二甲基苯并[a]蒽，是一种经过广泛研究的多环芳烃，长期以来一直被认为是可能的人类致癌物。已经发现DMBA在细菌以及动物或人细胞中是光毒性的，并且在鼠伤寒沙门氏菌TA102菌株中是光致突变的。本文试图解释光化学和光致突变性机制。光照射将DMBA转化为几种光产物，包括苯并[a]蒽-7,12-二酮，7-羟基-12-酮-7-甲基苯并[a]蒽，7,12-环氧二氧基-7,12-二氢-DMBA， 7-羟甲基-12-甲基苯并[a]蒽和12-羟甲基-7-甲基苯并[a]蒽。这些光产物的结构已通过与真实样品进行比较或通过NMR / MS进行了鉴定。至少需要分配四个其他照相产品。类似地进行了在小牛胸腺DNA存在下对DMBA的光照射，并通过32P后标记/ TLC分析了光诱导的DMBA-DNA加合物，表明形成了多个DNA加合物。这表明DNA加合物的形成可能是DMBA的光致突变性的来源。将大鼠肝微粒体从DMBA代谢中获得的代谢物与小牛胸腺DNA反应，并在相同条件下通过32P后标记/ TLC分析所得的DNA加合物。 DNA加合物谱的比较表明，光辐照形成的DNA加合物与DMBA代谢产物与DNA反应形成的DNA加合物不同。这些结果表明，DMBA的光辐照可以通过不同于DMBA微粒体代谢的激活途径而导致遗传毒性。

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