Hodgson R M, Seidel A, Bochnitschek W, Glatt H R, Oesch F, Grover P L
Carcinogenesis. 1985 Jan;6(1):135-9. doi: 10.1093/carcin/6.1.135.
9-Hydroxy-trans-1,2-dihydro-1,2-dihydroxychrysene (9-hydroxychrysene-1,2-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-1,2-diol was added during the incubation of 3H-labelled chrysene with rat-liver 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 with m-chloroperoxybenzoic acid, the synthetic 9-hydroxychrysene-1,2-diol formed products that possessed alkylating activity and that reacted with DNA in vitro. Examination of the triol-epoxides produced by oxidation of a mixture of synthetic and metabolic 9-hydroxychrysene-1,2-diol by t.l.c. suggested that the anti-isomer was formed.
9-羟基-反式-1,2-二氢-1,2-二羟基屈（9-羟基屈-1,2-二醇），它可能是小鼠皮肤中参与形成屈三醇环氧化物-DNA加合物的三醇，当屈与大鼠肝脏微粒体制剂一起孵育时未被检测到。在单独的实验中，在3H标记的屈与大鼠肝脏微粒体孵育期间加入过量的合成9-羟基屈-1,2-二醇，然后重新分离。发现该三醇含有一种放射性产物，在用反相高效液相色谱法、乙酰化前后通过正相高效液相色谱法以及氧化前后通过薄层色谱法检测时，其色谱性质与9-羟基屈-1,2-二醇相同。当用间氯过氧苯甲酸处理时，合成的9-羟基屈-1,2-二醇形成具有烷基化活性并在体外与DNA反应的产物。通过薄层色谱法对合成的和代谢产生的9-羟基屈-1,2-二醇混合物氧化产生的三醇环氧化物进行检测，结果表明形成了反式异构体。
