Reaction between S-nitrosothiols and thiols: generation of nitroxyl (HNO) and subsequent chemistry.
S-Nitrosothiols have been implicated to play key roles in a variety of physiological processes. The potential physiological importance of S-nitrosothiols prompted us to examine their reaction with thiols. We find that S-nitrosothiols can react with thiols to generate nitroxyl (HNO) and the corresponding disulfide. Further reaction of HNO with the remaining S-nitrosothiol and thiol results in the generation of other species including NO, sulfinamide, and hydroxylamine. Mechanisms are proposed that rationalize the observed products.
Wong
P S
PS
Department of Pharmacology, UCLA School of Medicine, Los Angeles, California 90095-1735, USA.
Hyun
J
J
Fukuto
J M
JM
Shirota
F N
FN
DeMaster
E G
EG
Shoeman
D W
DW
Nagasawa
H T
HT
D000332:Aerobiosis; D000641:Ammonia / Q000378:metabolism; D000975:Antioxidants / Q000737:chemistry / Q000378:metabolism; D005609:Free Radicals / Q000737:chemistry / Q000378:metabolism; D005978:Glutathione / Q000031:analogs & derivatives / Q000737:chemistry; D009569:Nitric Oxide / Q000737:chemistry; D009573:Nitrites / Q000378:metabolism; D009589:Nitrogen Oxides / Q000737:chemistry / Q000378:metabolism*; D009603:Nitroso Compounds / Q000737:chemistry*; D009609:Nitrous Oxide / Q000378:metabolism; D010084:Oxidation-Reduction; D026422:S-Nitrosoglutathione; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D000975:Antioxidants; D005609:Free Radicals; D009573:Nitrites; D009589:Nitrogen Oxides; D009603:Nitroso Compounds; D013438:Sulfhydryl Compounds; D009569:Nitric Oxide; D026422:S-Nitrosoglutathione; D000641:Ammonia; D005978:Glutathione; C039900:nitroxyl; D009609:Nitrous Oxide