The formation of 9-hydroxychrysene-1,2-diol as an intermediate in the metabolic activation of chrysene.
The formation of 9-hydroxychrysene-1,2-diol as an intermediate in the metabolic activation of chrysene.
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9-羟基-1,2-二醇的形成作为屈代谢活化的中间体。
DOI：
10.1093/carcin/6.1.135
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发表时间：
1985
期刊：
影响因子：
4.7
通讯作者：
Grover,PL
中科院分区：
文献类型：
--
作者：
Hodgson,RM;Seidel,A;Bochnitschek,W;Glatt,HR;Oesch,F;Grover,PL
9-羟基反式- 1,2 -二氢- 1,2 -二羟基chrysene（9-羟基chrysene- 1,2 -diol）可能是参与小鼠皮肤中三醇三醇环氧化物- dna加合物形成的三醇，当将chrysene与大鼠肝微粒体制备物孵育时未检测到。在单独的实验中，在3h标记的chrysene与猪肝微粒体孵育期间添加过量的合成9-羟基chrysene- 1,2 -diol，然后重新分离。在乙酰化前后用反相高效液相色谱法、氧化前后用正相高效液相色谱法和液相色谱法检测时，发现三醇含有一种放射性产物，其色谱性质与9-羟基蒽-1,2-二醇相同。经-氯过氧苯甲酸处理后，合成的9-羟基蒽-1,2-二醇产物具有烷基化活性，并能与DNAin体外反应。由合成的和代谢的9-羟基丙烯- 1,2 -二醇的混合物氧化产生的三环氧化合物，用t.l.c.检查表明形成了抗异构体。
9-Hydroxy-trans-l,2-dihydro-l,2-dihydroxychrysene (9-hydroxychrysene-l,2-diol), which may be the triol involved in the formation of a chrysene triol-epoxide-DNA adduct in mouse skin, was not detected when chrysene was incubated with rat-liver microsomal preparations. In separate experiments an excess of synthetic 9-hydroxychrysene-l,2-diol was added during the incubation of3H-labelled chrysene with ratliver microsomes and was then re-isolated. The triol was found to contain a radioactive product that had chromatographic properties identical to those of 9-hydroxychrysene-1,2-diol when examined by reverse-phase h.p.l.c, both before and after acetylation, by normal-phase h.p.l.c. and by t.l.c. both before and after oxidation. When treated withm-chloroperoxybenzoic acid, the synthetic 9-hydroxychrysene-1,2-diol formed products that possessed alkylating activity and that reacted with DNAin vitro. Examination of the triolepoxides produced by oxidation of a mixture of synthetic and metabolic 9-hydroxychrysene-l,2-diol by t.l.c. suggested that theanti-isomer was formed.