Characterization of 2′-deoxyguanosine oxidation products observed in the Fenton-like system Cu(II)/H2O2/reductant in nucleoside and oligodeoxynucleotide contexts

被引:72
|
作者
Fleming, Aaron M. [1 ]
Muller, James G. [1 ]
Ji, Insun [1 ]
Burrows, Cynthia J. [1 ]
机构
[1] Univ Utah, Dept Chem, 315 S 1400 E, Salt Lake City, UT 84112 USA
关键词
ONE-ELECTRON OXIDATION; DNA-SYNTHESIS OPPOSITE; DOUBLE-STRANDED DNA; GUANINE OXIDATION; HYDROGEN-PEROXIDE; IN-VITRO; EXCISION REPAIR; CROSS-LINKS; DAMAGE; SPIROIMINODIHYDANTOIN;
D O I
10.1039/c1ob05112a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reactive oxygen species attack both base and sugar moieties in DNA with a preference among the bases for reaction at guanine. In the present study, 2 '-deoxyguanosine (dG) was oxidized by a copper-mediated Fenton reaction with the reductants ascorbate or N-acetyl-cysteine, yielding oxidation on both the base and the sugar. The primary oxidized lesions observed in these studies include the 2 '-deoxyribonucleosides of 8-oxo-7,8-dihydroguanosine (dOG), spiroiminodihydantoin (dSp), guanidinohydantoin (dGh), oxazolone (dZ), and 5-carboxamido-5-formamido-2-iminohydantoin (d2Ih), as well as the free base guanine. d2Ih was the major product observed in the nucleoside, single- and double-stranded oligodeoxynucleotide contexts and is proposed to arise from oxidation at C5 of guanine. Product distribution studies provide insight into the role of the reductant in partitioning of dG base oxidation along the C5 and C8 pathways.
引用
收藏
页码:3338 / 3348
页数:11
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