N2-(4-羟苯基)-2'-脱氧鸟苷3'-磷酸的合成：通过32P后标记法与对苯二酚处理的HL-60细胞中形成的DNA加合物进行比较。
Synthesis of N2-(4-hydroxyphenyl)-2'-deoxyguanosine 3'-phosphate: comparison by 32P-postlabeling with the DNA adduct formed in HL-60 cells treated with hydroquinone.
作者信息
Pongracz K, Bodell W J
机构信息
Department of Neurological Surgery, School of Medicine, University of California, San Francisco 94143, USA.
出版信息
Chem Res Toxicol. 1996 Apr-May;9(3):593-8. doi: 10.1021/tx9500991.
A new adduct has been isolated from the reaction of guanosine 3'-phosphate and p-benzoquinone. The structure of this adduct has been determined as N2-(4-hydroxyphenyl)-guanosine 3'-phosphate. 32P-Postlabeling showed that this adduct is similar to the DNA adduct formed in HL-60 cells treated with hydroquinone. For comparison with the corresponding deoxyribonucleotide, a synthetic procedure was developed for the preparation of N2-substituted derivatives of 2'-deoxyguanosine 3'-phosphate. 2-Bromo-2'-deoxyinosine 3'-phosphate was synthesized with a combination of synthetic and enzymatic methods. Reaction of 2-bromo-2'-deoxyinosine 3'-phosphate with 4-hydroxyaniline gave N2-(4-hydroxyphenyl)-2'-deoxyguanosine 3'-phosphate. Using 32P-postlabeling, we compared this product with the DNA adduct produced in HL-60 cells treated with hydroquinone. The results of these studies suggest that the DNA adduct formed in HL-60 cells treated with hydroquinone corresponds to N2-(4-hydroxyphenyl)-2'-deoxyguanosine 3'-phosphate.
从鸟苷3'-磷酸与对苯醌的反应中分离出了一种新的加合物。该加合物的结构已确定为N2-(4-羟基苯基)-鸟苷3'-磷酸。32P后标记显示，这种加合物与用对苯二酚处理的HL-60细胞中形成的DNA加合物相似。为了与相应的脱氧核糖核苷酸进行比较，开发了一种合成方法来制备2'-脱氧鸟苷3'-磷酸的N2-取代衍生物。采用合成法与酶法相结合合成了2-溴-2'-脱氧肌苷3'-磷酸。2-溴-2'-脱氧肌苷3'-磷酸与4-羟基苯胺反应生成N2-(4-羟基苯基)-2'-脱氧鸟苷3'-磷酸。利用32P后标记，我们将该产物与用对苯二酚处理的HL-60细胞中产生的DNA加合物进行了比较。这些研究结果表明，用对苯二酚处理的HL-60细胞中形成的DNA加合物对应于N2-(4-羟基苯基)-2'-脱氧鸟苷3'-磷酸。
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