S-nitroglutathione, a product of the reaction between peroxynitrite and glutathione that generates nitric oxide

被引:117
作者
Balazy, M [1 ]
Kaminski, PM
Mao, KY
Tan, JZ
Wolin, MS
机构
[1] New York Med Coll, Dept Pharmacol, Valhalla, NY 10595 USA
[2] New York Med Coll, Dept Physiol, Valhalla, NY 10595 USA
关键词
D O I
10.1074/jbc.273.48.32009
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Peroxynitrite (ONOO-) has been shown in studies on vascular relaxation and guanylate cyclase activation to react with glutathione (GSH), generating an intermediate product that promotes a time-dependent production of nitric oxide (NO), In this study, reactions of ONOO- with GSH produced a new substance, which was characterized by liquid chromatography, ultraviolet spectroscopy, and electrospray tandem mass spectrometry, The mass spectrometric data provided evidence that the product of this reaction was S-nitroglutathione (GSNO(2)) and that S-nitrosoglutathione (GSNO) was not a detectable product of this reaction. Further evidence was obtained by comparison of the spectral and chromatographic properties with synthetic standards prepared by reaction of GSH with nitrosonium or nitronium borofluorates, Both the synthetic and ONOO-/GSH-derived GSNO(2) generated a protonated ion, GSNO(2)H(+) at mit 353, which was unusually resistant to decomposition under collision activation, and no fragmentation was observed at collision energy of 25 eV, In contrast, an ion at mit 337 (GSNOH(+)), generated from the synthetic GSNO, readily fragmented with the abundant loss of NO at 9 eV, Reactions of ONOO- with GSH resulted in the generation of NO, which was detected by the head space/NO-chemiluminescence analyzer method, The generation of NO was inhibited by the presence of glucose and/or CO2 in the buffers employed. Synthetic GSNO(2) spontaneously generated NO in a manner that was not significantly altered by glucose or CO2. Thus, ONOO- reacts with GSH to form GSNO(2), and GSNO(2) decomposes in a manner that generates NO.
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页码:32009 / 32015
页数:7
相关论文
共 24 条
[1]   Reactivity of thionitrate esters: Putative intermediates in nitrovasodilator activity [J].
Artz, JD ;
Yang, KX ;
Lock, J ;
Sanchez, C ;
Bennett, BM ;
Thatcher, GRJ .
CHEMICAL COMMUNICATIONS, 1996, (08) :927-928
[2]  
Balazy Michael, 1994, Polish Journal of Pharmacology, V46, P593
[3]   Carbon dioxide stimulates peroxynitrite-mediated nitration of tyrosine residues and inhibits oxidation of methionine residues of glutamine synthetase: Both modifications mimic effects of adenylylation [J].
Berlett, BS ;
Levine, RL ;
Stadtman, ER .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1998, 95 (06) :2784-2789
[4]   QUANTITATION OF NITRIC-OXIDE FORMATION FROM NITROVASODILATOR DRUGS BY CHEMILUMINESCENCE ANALYSIS OF HEADSPACE GAS [J].
BRIEN, JF ;
MCLAUGHLIN, BE ;
NAKATSU, K ;
MARKS, GS .
JOURNAL OF PHARMACOLOGICAL METHODS, 1991, 25 (01) :19-27
[5]   ORGANIC NITRATES, THIONITRATES, PEROXYNITRITES, AND NITRIC-OXIDE - A MOLECULAR-ORBITAL STUDY OF THE RXNO(2)REVERSIBLE-ARROW-RXONO (X=O, S) REARRANGEMENT, A REACTION OF POTENTIAL BIOLOGICAL SIGNIFICANCE [J].
CAMERON, DR ;
BORRAJO, AMP ;
BENNETT, BM ;
THATCHER, GRJ .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1995, 73 (10) :1627-1638
[6]   NO elicits prolonged relaxation of bovine pulmonary arteries via endogenous peroxynitrite generation [J].
Davidson, CA ;
Kaminski, PM ;
Wolin, MS .
AMERICAN JOURNAL OF PHYSIOLOGY-LUNG CELLULAR AND MOLECULAR PHYSIOLOGY, 1997, 273 (02) :L437-L444
[7]   Nitrogen dioxide causes pulmonary arterial relaxation via thiol nitrosation and NO formation [J].
Davidson, CA ;
Kaminski, PM ;
Wu, MD ;
Wolin, MS .
AMERICAN JOURNAL OF PHYSIOLOGY-HEART AND CIRCULATORY PHYSIOLOGY, 1996, 270 (03) :H1038-H1043
[8]   Endogenous peroxynitrite generation causes a subsequent suppression of coronary arterial contraction to serotonin [J].
Davidson, CA ;
Kaminski, PM ;
Wolin, MS .
NITRIC OXIDE-BIOLOGY AND CHEMISTRY, 1997, 1 (03) :244-253
[9]   Peroxynitrite reaction with carbon dioxide/bicarbonate: Kinetics and influence on peroxynitrite-mediated oxidations [J].
Denicola, A ;
Freeman, BA ;
Trujillo, M ;
Radi, R .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1996, 333 (01) :49-58
[10]   The effects of peroxynitrite on rat aorta: interaction with glucose and related substances [J].
Dowell, FJ ;
Martin, W .
EUROPEAN JOURNAL OF PHARMACOLOGY, 1997, 338 (01) :43-53