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首页> 美国卫生研究院文献>Proceedings of the National Academy of Sciences of the United States of America >Enzymatic conversion of benzo(a)pyrene leading predominantly to the diol-epoxide r-7t-8-dihydroxy-t-910-oxy-78910-tetrahydrobenzo(a)pyrene through a single enantiomer of r-7 t-8-dihydroxy-78-dihydrobenzo(a)pyrene.
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Enzymatic conversion of benzo(a)pyrene leading predominantly to the diol-epoxide r-7t-8-dihydroxy-t-910-oxy-78910-tetrahydrobenzo(a)pyrene through a single enantiomer of r-7 t-8-dihydroxy-78-dihydrobenzo(a)pyrene.

机译：通过单一对映异构体将苯并（a）py主要转化为二醇-环氧化物r-7t-8-二羟基-t-910-氧基-78910-四氢苯并（a）py r-7t-8-二羟基-78-二氢苯并（a）py的合成。

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Benzo(a)pyrene is metabolically and stereospecifically converted by mixed-function oxidases of rat liver microsomes and epoxide hydratase (glycol hydro-lyase (epoxide-forming), EC 4.2.1.63)to the single enantiomer (-)r-7,t-8-dihydroxy-7,8-dihydrobenzol (A) pyrene. This enantiomer is further metabolized stereoselectively by the mixed-function oxidases to predominantly the diol-epoxide, r-7,t-8-dihydroxy-t-9,10-oxy-7,8,9,10-tetrahydrobenzol(a)pyrene in which the 7-hydroxyl and the 9,10-epoxide are trans. Other unidentified metabolites are also formed from the r-7,t-8-dihydroxy-7,8-dihydrobenzo(a)pyrene. Racemic r-7,t-8-dihydroxy-7,8-dihydrobenzo(a)-pyrene is converted metabolically to both r-7,t-8-dihydroxy-t-9,10-oxy-7,8,9,10-tetrahydrobenzo(a)pyrene and r-7,t-8-dihydroxy-c-9,10-oxy-7,8,9,10-tetrahydrobenzo(a)pyrene. The diol-epoxides are unstable in aqueous medium, and their identification and characterization as r-7,t-8-dihydroxy-t-9,10-oxy-7,8,9,10-tetrahydrobenzo(a)pyrene and r-7,t-8-dihydroxy-c-9,10-oxy-7,8,9,10-tetrahydrobenzo(a)pyrene were accomplished by the identity of their tetrahydroxytetrahydrobenzo(a)pyrenes hydrolysis products with those of the authentic synthetic compounds with respect to mobility on high-pressure liquid chromatography and mass and ultraviolet absorption spectral analysis. The diol-epoxides were also reduced in the presence of NADPH to distinct trihydroxypentahydrobenzo(a)pyrenes. Since the synthetic racemic r-7,t-8-dihydroxy-t-9,10-oxy-7,8,9,10-tetrahydrobenzo(a)pyrene is very highly mutagenic in mammalian cells, we suggest that it is the metabolically formed diol-epoxide that may be an ultimate carcinogenic form of benzo(a)pyrene.
机译：苯并（a）re通过大鼠肝微粒体的混合功能氧化酶和环氧化物水合酶（乙二醇水解酶（环氧化物形成），EC 4.2.1.63）代谢和立体定向转化为单一对映体（-）r-7，t -8-二羟基-7,8-二氢苯甲酰基（A）.。该对映异构体进一步被混合功能氧化酶立体选择性地代谢，主要是二醇-环氧化物，r-7，t-8-二羟基-t-9,10-氧-7,8,9,10-四氢苯并（a）py其中7-羟基和9,10-环氧是反式的。其他未确定的代谢物也由r-7，t-8-二羟基-7,8-二氢苯并（a）formed形成。外消旋的r-7，t-8-二羟基-7,8-二氢苯并（a）-py被代谢转化为r-7，t-8-二羟基-t-9,10-oxy-7,8,9， 10-四氢苯并（a）py和r-7，t-8-二羟基-c-9,10-氧-7,8,9,10-四氢苯并（a）py。二醇环氧化合物在水性介质中不稳定，其鉴定和表征为r-7，t-8-二羟基-t-9,10-氧基-7,8,9,10-四氢苯并（a）py和r- 7，t-8-二羟基-c-9,10-氧基-7,8,9,10-四氢苯并（a）py是通过将它们的四羟基四氢苯并（a）py水解产物与真实的合成化合物鉴定而完成高压液相色谱的迁移率以及质谱和紫外吸收光谱分析。在NADPH存在下，二醇-环氧化合物也被还原成不同的三羟基五氢苯并（a）py。由于合成的外消旋体r-7，t-8-二羟基-t-9,10-氧基-7,8,9,10-四氢苯并（a）py在哺乳动物细胞中具有很高的致突变性，因此我们认为这是代谢性的形成的二醇环氧化合物可能是苯并（a）an的最终致癌形式。

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