Osborne M R, Beland F A, Harvey R G, Brookes P
Int J Cancer. 1976 Sep 15;18(3):362-8. doi: 10.1002/ijc.2910180315.
The reaction of (+/-)-7alpha,8beta-dihydroxy-9beta,10beta-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene (BP diol epoxide) with DNA, followed by enzymatic hydrolysis and LH 20 Sephadex column chromatography, yielded products containing a purine deoxyribonucleoside linked to a 7,8,9,10-tetrahydrobenzo(a)pyrene derivative. DNA containing tritiated adenine or pyrimidines gave little or no tritiated products, showing that reaction occurred chiefly with the guanine residues. Results with 8-(3H)-guanine-labelled DNA, and studies on the protonation and ionization of the products in acid or alkaline media, led to the formulation of the main product as an N2-substituted guanine derivative. The reaction of BP diol epoxide with deoxyadenosine and deoxyguanosine gave further nucleoside derivatives which were probably minor products in the reaction with DNA. Treatment with strong acid unexpectedly converted each of the isolated products to free guanine or adenine.
（±）-7α，8β-二羟基-9β，10β-环氧-7，8，9，10-四氢苯并（a）芘（BP二醇环氧化物）与DNA反应，随后进行酶促水解和LH 20葡聚糖凝胶柱色谱分析，得到的产物含有与7，8，9，10-四氢苯并（a）芘衍生物相连的嘌呤脱氧核糖核苷。含有氚化腺嘌呤或嘧啶的DNA产生很少或没有氚化产物，表明反应主要发生在鸟嘌呤残基上。用8-（3H）-鸟嘌呤标记的DNA得到的结果，以及对产物在酸性或碱性介质中的质子化和电离的研究，得出主要产物为N2-取代鸟嘌呤衍生物的结论。BP二醇环氧化物与脱氧腺苷和脱氧鸟苷的反应产生了进一步的核苷衍生物，它们可能是与DNA反应中的次要产物。用强酸处理意外地将每种分离产物转化为游离鸟嘌呤或腺嘌呤。
