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苯并[c]菲3,4 -二氢二醇1,2 -环氧化物在天然和变性DNA中的加合物

Benzo[c]phenanthrene 3,4-dihydrodiol 1,2-epoxide adducts in native and denatured DNA.

作者信息

Agarwal R, Yagi H, Jerina D M, Dipple A

机构信息

Chemistry of Carcinogenesis Laboratory, ABL-Basic Research Program, NCI-Frederick Cancer Research and Development Center, MD 21702, USA.

出版信息

Carcinogenesis. 1996 Aug;17(8):1773-6. doi: 10.1093/carcin/17.8.1773.

DOI:10.1093/carcin/17.8.1773
PMID:8761442
Abstract

High performance liquid chromatography/UV-absorption and 32P-postlabeling were used to quantitate adducts generated by reaction of the four configurationally isomeric benzo[c]phenanthrene 3,4-dihydrodiol 1,2-epoxides with native or denatured DNA in vitro. For both the 4R, 3S-dihydrodiol 2S,1R-epoxide and the 4S,3R-dihydrodiol 2S,1R-epoxide, the amount of product resulting from trans-opening of the epoxide ring by the exocyclic amino group of deoxyadenosine in denatured DNA was much less than the level found in native DNA, indicating that the native DNA structure probably intercalates the hydrocarbon residue in a fashion that promotes adenine reaction for 2S,1R-epoxides.

摘要

采用高效液相色谱/紫外吸收法和³²P后标记法,对四种构型异构的苯并[c]菲3,4 - 二氢二醇1,2 - 环氧化物与天然或变性DNA在体外反应生成的加合物进行定量分析。对于4R, 3S - 二氢二醇2S,1R - 环氧化物和4S,3R - 二氢二醇2S,1R - 环氧化物而言,变性DNA中脱氧腺苷的环外氨基对环氧环进行反式开环所产生的产物量,远低于天然DNA中的水平,这表明天然DNA结构可能以促进2S,1R - 环氧化物与腺嘌呤反应的方式插入烃类残基。

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引用本文的文献

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In vitro and in vivo modulations of benzo[c]phenanthrene-DNA adducts by DNA mismatch repair system.DNA错配修复系统对苯并[c]菲-DNA加合物的体外和体内调节作用。
Nucleic Acids Res. 2003 Nov 15;31(22):6428-34. doi: 10.1093/nar/gkg875.