Szeliga J, Lee H, Harvey R G, Page J E, Ross H L, Routledge M N, Hilton B D, Dipple A
Chemistry of Carcinogenesis Laboratory, PRI, DynCorp, Inc., NCI-Frederick Cancer Research and Development Center, Maryland 21701.
Chem Res Toxicol. 1994 May-Jun;7(3):420-7. doi: 10.1021/tx00039a021.
The spectroscopic characterization of purine deoxyribonucleoside adducts derived from the fjord-region syn-benzo[g]chrysene 11,12-dihydrodiol 13,14-epoxide and the mutagenic specificity of the latter compound for the supF gene in the pSP189 shuttle vector are described. This dihydrodiol epoxide preferentially forms adducts with deoxyadenosine residues in DNA and is preferentially opened trans in reactions with DNA or with deoxyribonucleotides. In common with other fjord-region syn-dihydrodiol epoxides, the most frequently observed mutational changes were A-->T and G-->T changes. This hydrocarbon dihydrodiol epoxide is structurally similar to syn-benzo[c]phenanthrene 3,4-dihydrodiol 1,2-epoxide but has an additional benzene ring annelated distant from the reaction center. As anticipated, there were some common features in the chemistry and mutagenicities of these two compounds, but there were also substantive differences which indicate factors of importance in controlling reactions of these kinds of compounds with DNA.
描述了源自峡湾区顺式苯并[g]屈11,12 - 二氢二醇13,14 - 环氧化物的嘌呤脱氧核糖核苷加合物的光谱表征，以及后一种化合物对pSP189穿梭载体中supF基因的诱变特异性。这种二氢二醇环氧化物优先与DNA中的脱氧腺苷残基形成加合物，并且在与DNA或脱氧核糖核苷酸反应时优先发生反式开环。与其他峡湾区顺式二氢二醇环氧化物一样，最常观察到的突变变化是A→T和G→T变化。这种烃类二氢二醇环氧化物在结构上类似于顺式苯并[c]菲3,4 - 二氢二醇1,2 - 环氧化物，但在远离反应中心的位置有一个额外的稠合苯环。正如预期的那样，这两种化合物在化学性质和诱变性方面有一些共同特征，但也存在实质性差异，这表明在控制这类化合物与DNA反应中重要的因素。
