2′-deoxyguanosine (DG) oxidation and strand-break formation in DNA by the radicals released in the photolysis of N-tert-butoxy-2-pyridone.: Are tert-butoxyl or methyl radicals responsible for the photooxidative damage in aqueous media?

被引:14
作者
Adam, W
Marquardt, S
Kemmer, D
Saha-Möller, CR
Schreier, P
机构
[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
[2] Univ Wurzburg, Inst Lebensmittelchem, D-97074 Wurzburg, Germany
关键词
D O I
10.1021/ol016955j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The photolysis of pyridone 3b (photo-Fenton reagent) in benzene releases tent-butoxyl radicals, which have been trapped by DMPO and EPR-spectrally identified. In, aqueous solution, however, the fragmentation of the tent-butoxyl into methyl radicals prevails and the former radicals are of no direct consequence in the photooxidation of 2'-deoxyguanosine (dG) and pBR 322 DNA. The photooxidative damage of nucleic acids is caused by the oxyl radical species generated from the methyl radicals with oxygen.
引用
收藏
页码:225 / 228
页数:4
相关论文
共 22 条
  • [1] Oxidative DNA damage in the photolysis of N-hydroxy-2-pyridone, a specific hydroxyl-radical source
    Adam, W
    Marquardt, S
    Saha-Möller, CR
    [J]. PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1999, 70 (03) : 287 - 291
  • [2] Are pyridinethiones reliable photochemical oxyl-radical sources for photobiological studies?: The importance of secondary photolysis products in the guanine oxidation of 2′-deoxyguanosine and cell-free DNA
    Adam, W
    Grimm, GN
    Marquardt, S
    Saha-Möller, CR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (06) : 1179 - 1185
  • [3] DNA damage by tert-butoxyl radicals generated in the photolysis of a water-soluble, DNA-binding peroxyester acting as a radical source
    Adam, W
    Grimm, GN
    Saha-Möller, CR
    Dall'Acqua, F
    Miolo, G
    Vedaldi, D
    [J]. CHEMICAL RESEARCH IN TOXICOLOGY, 1998, 11 (09) : 1089 - 1097
  • [4] 4-tert-butylperoxymethyl-9-methoxypsoralen as intercalating photochemical alkoxyl-radical source for oxidative DNA damage
    Adam, W
    Arnold, MA
    Grimm, GN
    Saha-Möller, CR
    Dall'Acqua, F
    Miolo, G
    Vedaldi, D
    [J]. PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1998, 68 (04) : 511 - 518
  • [5] ADAM W, 1989, FREE RADICAL BIO MED, V24, P234
  • [6] ALKYLATION AND CLEAVAGE OF DNA BY CARBON-CENTERED RADICAL METABOLITES
    AUGUSTO, O
    [J]. FREE RADICAL BIOLOGY AND MEDICINE, 1993, 15 (03) : 329 - 336
  • [7] Photochemistry of N-hydroxy-2(1H)-pyridone, a more selective source of hydroxyl radicals than N-hydroxypyridine-2(1H)-thione
    Aveline, BM
    Kochevar, IE
    Redmond, RW
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (42) : 10124 - 10133
  • [8] RADICAL SPECIES PRODUCED FROM THE PHOTOLYTIC AND PULSE-RADIOLYTIC DEGRADATION OF TERT-BUTYL HYDROPEROXIDE - AN EPR SPIN TRAPPING INVESTIGATION
    BORS, W
    MICHEL, C
    STETTMAIER, K
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (09): : 1513 - 1517
  • [9] ABSOLUTE RATE CONSTANTS OF ALKOXYL RADICAL REACTIONS IN AQUEOUS-SOLUTION
    ERBENRUSS, M
    MICHEL, C
    BORS, W
    SARAN, M
    [J]. JOURNAL OF PHYSICAL CHEMISTRY, 1987, 91 (09) : 2362 - 2365
  • [10] Gutteridge J. M. C., 1989, FREE RADICALS BIOL M