Sodium nitroprusside: Mechanism of NO release mediated by sulfhydryl-containing molecules

被引:141
作者
Grossi, L [1 ]
D'Angelo, S [1 ]
机构
[1] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy
关键词
D O I
10.1021/jm049857n
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Sodium nitroprusside (SNP) is among the most widely studied nitric oxide donors, and its capability of producing NO seems to depend on its interaction with sulfhydryl-containing molecules present in vivo. The aim of this research has been the study of the mechanism of interaction between SNP and sulfhydryl-containing compounds, such as cysteine and glutathione, through detection by EPR, UV-vis, and IR spectroscopy of both the radical and nonradical species involved. An electron-transfer process can be invoked as the key step, which leads to the formation of the reduced SNP radical, the main detectable radical intermediate, and the corresponding S-nitrosothiol, the ending product of NO that can be considered the real storage and transporters of NO. When cysteine was used, a second radical species (A) is detectable: it can be accounted for by the interaction of a byproduct with unreacted cysteine.
引用
收藏
页码:2622 / 2626
页数:5
相关论文
共 25 条
[1]   FORMATION OF PARAMAGNETIC MONONUCLEAR IRON NITROSYL COMPLEXES FROM DIAMAGNETIC DINUCLEAR AND TETRANUCLEAR IRON SULFUR NITROSYLS - CHARACTERIZATION BY ELECTRON-PARAMAGNETIC-RES SPECTROSCOPY AND STUDY OF THIOLATE AND NITROSYL LIGAND-EXCHANGE REACTIONS [J].
BUTLER, AR ;
GLIDEWELL, C ;
HYDE, AR ;
WALTON, JC .
POLYHEDRON, 1985, 4 (05) :797-809
[2]   Non-heme iron nitrosyls in biology [J].
Butler, AR ;
Megson, IL .
CHEMICAL REVIEWS, 2002, 102 (04) :1155-1165
[3]   Comproportionation and disproportionation reactions in the electrochemical reduction of nitroprusside at a hanging mercury drop electrode in acidic solution [J].
Carapuca, HM ;
Simao, JEJ ;
Fogg, AG .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1998, 455 (1-2) :93-105
[4]   ONE-ELECTRON REDUCTION OF PENTACYANONITROSYLFERRATE(II) ION IN AQUEOUS-SOLUTION [J].
CHENEY, RP ;
SIMIC, MG ;
HOFFMAN, MZ ;
TAUB, IA ;
ASMUS, KD .
INORGANIC CHEMISTRY, 1977, 16 (09) :2187-2192
[5]   Re-examination of the formation of dinitrosyl-iron complexes during reaction of S-nitrosothiols with Fe(II) [J].
Costanzo, S ;
Ménage, S ;
Purrello, R ;
Bonomo, RP ;
Fontecave, M .
INORGANICA CHIMICA ACTA, 2001, 318 (1-2) :1-7
[6]   The use of nitric oxide donors in pharmacological studies [J].
Feelisch, M .
NAUNYN-SCHMIEDEBERGS ARCHIVES OF PHARMACOLOGY, 1998, 358 (01) :113-122
[7]   DEFINITIVE IDENTIFICATION OF THE PRIMARY REDUCTION PRODUCT OF THE NITROPRUSSIDE ION, PENTACYANONITROSYLFERRATE(2-), IN AQUEOUS-SOLUTION [J].
GLIDEWELL, C ;
JOHNSON, IL .
INORGANICA CHIMICA ACTA, 1987, 132 (02) :145-147
[8]   Mechanism of the nitrosation of thiols and amines by oxygenated center dot NO solutions: The nature of the nitrosating intermediates [J].
Goldstein, S ;
Czapski, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (14) :3419-3425
[9]  
Grossi L, 2002, CHEM-EUR J, V8, P380, DOI 10.1002/1521-3765(20020118)8:2<380::AID-CHEM380>3.0.CO
[10]  
2-P