（±）-7α，8β-二羟基-9β，10β-环氧-7,8,9,10-四氢苯并（a）芘是苯并（a）芘代谢及与DNA结合过程中的一种中间体。
(+/-)-7alpha,8beta-dihydroxy-9beta,10beta-epoxy-7,8,9,10-tetrahydrobenzo(a)-pyrene is an intermediate in the metabolism and binding to DNA of benzo(a)pyrene.
作者信息
King H W, Osborne M R, Beland F A, Harvey R G, Brookes P
出版信息
Proc Natl Acad Sci U S A. 1976 Aug;73(8):2679-81. doi: 10.1073/pnas.73.8.2679.
Abstract
The addition of borate buffer to the aqueous methanol used to elute hydrocarbon-deoxyribonucleoside derivatives from an LH 20 Sephadex column resulted in the separation of the products of reaction with DNA of the stereoisomers, (+/-)7alpha,8beta-dihydroxy-9alpha,10alpha-epoxy- and (+/-)-7alpha,8beta-dihydroxy-9beta,10beta-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrenes, i.e., the syn- and anti-benzo(a)pyrene-diolepoxide, respecitvely. By this technique it was shown that the microsome-mediated binding to DNA of benzo(a)pyrene-7,8-dihydrodiol involved exclusively the anti-benzo(a)pyrene-diolepoxide. The benzo(a)pyrene binding to DNA that resulted on exposure of BHK21/C13 cells to this carcinogen was also shown to result predominantly by reaction of the anti-benzo(a)pyrene-diolepoxide. However, in this case other derivatives, including the syn-benzo(a)pyrene diolepoxide, might also be involved.
摘要
向用于从LH 20葡聚糖凝胶柱上洗脱烃基脱氧核糖核苷衍生物的甲醇水溶液中添加硼酸盐缓冲液，可分离出立体异构体（±）7α，8β - 二羟基 - 9α，10α - 环氧 - 和（±） - 7α，8β - 二羟基 - 9β，10β - 环氧 - 7,8,9,10 - 四氢苯并（a）芘与DNA反应的产物，即分别为顺式和反式苯并（a）芘 - 二环氧二醇。通过该技术表明，微粒体介导的苯并（a）芘 - 7,8 - 二氢二醇与DNA的结合仅涉及反式苯并（a）芘 - 二环氧二醇。将BHK21 / C13细胞暴露于这种致癌物后导致的苯并（a）芘与DNA的结合也主要显示是由反式苯并（a）芘 - 二环氧二醇的反应引起的。然而，在这种情况下，其他衍生物，包括顺式苯并（a）芘二环氧二醇，也可能参与其中。
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The relation of metabolism to macromolecular binding of the carcinogen benzo[a]pyrene, by mouse embryo cells in culture.培养的小鼠胚胎细胞中代谢作用与致癌物苯并[a]芘大分子结合的关系。
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Metabolic activation of benzo(a)pyrene proceeds by a diol-epoxide.苯并(a)芘的代谢活化通过二醇环氧化物进行。
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Exceptional mutagenicity of a benzo(a)pyrene diol epoxide in cultured mammalian cells.苯并(a)芘二醇环氧化物在培养的哺乳动物细胞中的超强致突变性。
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The reaction of 7,8-dihydro-7,8-dihydroxybenzo (a) pyrene-9,10-oxide with DNA in relation to the benzo (a) pyrene-DNA products isolated from cells.7,8-二氢-7,8-二羟基苯并(a)芘-9,10-氧化物与DNA的反应与从细胞中分离出的苯并(a)芘-DNA产物的关系。
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Rat liver microsome-mediated binding of benzo(a)pyrene metabolites to DNA.大鼠肝微粒体介导的苯并(a)芘代谢产物与DNA的结合。
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Letter: Synthesis of (+/-)-7 beta,8alpha-dihydroxy-9 beta,10beta-epoxy-7,8,-9,10-tetrahydrobenzo(a)pyrene, a potential metabolite of the carcinogen benzo(a)pyrene with stereochemistry related to the antileukemic triptolides.信函：（±）-7β，8α-二羟基-9β，10β-环氧-7,8,-9,10-四氢苯并（a）芘的合成，苯并（a）芘的一种潜在代谢产物，其立体化学与抗白血病雷公藤内酯醇相关 。
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