An adduct between peroxynitrite and 2'-deoxyguanosine: 4,5-dihydro-5-hydroxy-4-(nitrosooxy)-2'-deoxyguanosine

被引:96
作者
Douki, T [1 ]
Cadet, J [1 ]
Ames, BN [1 ]
机构
[1] UNIV CALIF BERKELEY, DIV BIOCHEM & MOLEC BIOL, BERKELEY, CA 94720 USA
关键词
NITRIC-OXIDE; SUPEROXIDE-DISMUTASE; NITRATION; OXIDANTS;
D O I
10.1021/tx950126n
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The reactivity of peroxynitrite (OONO-) with DNA is of interest because it is released during chronic inflammation, a major contributor to cancer. Peroxynitrite was found to undergo homolytic addition to the C4-C5 double bond of 2'-deoxyguanosine with formation of 4,5-dihydro-5-hydroxy-4-(nitrosooxy)-2'-deoxyguanosine (nox-dG). This adduct may be a useful marker in the study of the chemical processes associated with the mutagenicity of peroxynitrite.
引用
收藏
页码:3 / 7
页数:5
相关论文
共 38 条
[1]   THE CAUSES AND PREVENTION OF CANCER [J].
AMES, BN ;
GOLD, LS ;
WILLETT, WC .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1995, 92 (12) :5258-5265
[2]   OXIDANTS, ANTIOXIDANTS, AND THE DEGENERATIVE DISEASES OF AGING [J].
AMES, BN ;
SHIGENAGA, MK ;
HAGEN, TM .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (17) :7915-7922
[3]   MUTAGENICITY OF NITRIC-OXIDE AND ITS INHIBITION BY ANTIOXIDANTS [J].
ARROYO, PL ;
HATCHPIGOTT, V ;
MOWER, HF ;
COONEY, RV .
MUTATION RESEARCH, 1992, 281 (03) :193-202
[4]   APPARENT HYDROXYL RADICAL PRODUCTION BY PEROXYNITRITE - IMPLICATIONS FOR ENDOTHELIAL INJURY FROM NITRIC-OXIDE AND SUPEROXIDE [J].
BECKMAN, JS ;
BECKMAN, TW ;
CHEN, J ;
MARSHALL, PA ;
FREEMAN, BA .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1990, 87 (04) :1620-1624
[5]   ALS, SOD AND PEROXYNITRITE [J].
BECKMAN, JS ;
CARSON, M ;
SMITH, CD ;
KOPPENOL, WH .
NATURE, 1993, 364 (6438) :584-584
[6]   KINETICS OF SUPEROXIDE DISMUTASE-CATALYZED AND IRON-CATALYZED NITRATION OF PHENOLICS BY PEROXYNITRITE [J].
BECKMAN, JS ;
ISCHIROPOULOS, H ;
ZHU, L ;
VANDERWOERD, M ;
SMITH, C ;
CHEN, J ;
HARRISON, J ;
MARTIN, JC ;
TSAI, M .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1992, 298 (02) :438-445
[7]   REACTION OF SUPEROXIDE WITH NITRIC-OXIDE TO FORM PEROXONITRITE IN ALKALINE AQUEOUS-SOLUTION [J].
BLOUGH, NV ;
ZAFIRIOU, OC .
INORGANIC CHEMISTRY, 1985, 24 (22) :3502-3504
[8]   THE COMPARATIVE TOXICITY OF NITRIC-OXIDE AND PEROXYNITRITE TO ESCHERICHIA-COLI [J].
BRUNELLI, L ;
CROW, JP ;
BECKMAN, JS .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1995, 316 (01) :327-334
[9]   DETECTION OF DEOXYRIBONUCLEOSIDES ON PAPER CHROMATOGRAMS [J].
BUCHANAN, JG .
NATURE, 1951, 168 (4286) :1091-1091
[10]   2,2-DIAMINO-4-[(3,5-DI-O-ACETYL-2-DEOXY-BETA-D-ERYTHROPENTOFURANOSYL) AMINO]-5-(2H)-OXAZOLONE - A NOVEL AND PREDOMINANT RADICAL OXIDATION-PRODUCT OF 3',5'-DI-O-ACETYL-2'-DEOXYGUANOSINE [J].
CADET, J ;
BERGER, M ;
BUCHKO, GW ;
JOSHI, PC ;
RAOUL, S ;
RAVANAT, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (16) :7403-7404