The reaction of (±)‐7α, 8β‐dihydroxy‐9β, 10β‐epoxy‐7,8,9,10‐tetrahydrobenzo(a)pyrene with dna
The reaction of (±)‐7α, 8β‐dihydroxy‐9β, 10β‐epoxy‐7,8,9,10‐tetrahydrobenzo(a)pyrene with dna
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(±)-7α,8β-二羟基-9β,10β-环氧-7,8,9,10-四氢苯并(a)芘与DNA的反应
DOI：
10.1002/ijc.2910180315
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发表时间：
1976
影响因子：
6.4
通讯作者：
R. Harvey
中科院分区：
文献类型：
--
作者：
M. Osborne;P. Brookes;F. Beland;R. Harvey
（±）‐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，然后进行酶解和LH 20 Sephadex柱层析，得到含有嘌呤脱氧核糖核苷连接到7,8,9,10‐四氢苯并(a)芘衍生物的产物。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DNA的结果，以及对产物在酸或碱性介质中的质子化和电离的研究，导致了主要产物作为N2‐取代鸟嘌呤衍生物的配方。BP二醇环氧化物与脱氧腺苷和脱氧鸟苷反应得到更多的核苷衍生物，这些核苷可能是与DNA反应的次要产物。强酸处理意外地将每个分离产物转化为游离鸟嘌呤或腺嘌呤。
The reaction of (±)‐7α,8β‐dihydroxy‐9β,10β‐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.