Biomaterial Database

Diethyl dithiocarbamate-induced decomposition of S-nitrosothiols. 1997

D R Arnelle, and B J Day, and J S Stamler

Division of Respiratory Medicine, Duke University Medical Center, Durham, North Carolina 27710, USA.

Diethyl dithiocarbamate (DDC) has been used extensively as an inhibitor of CuZn superoxide dismutase (SOD) in the study of superoxide and nitric oxide. Addition of DDC to solutions of the endogenous NO adduct S-nitrosoglutathione (GSNO) causes a rapid decrease in GSNO with concomitant formation of nitrite, nitrate, disulfuram, oxidized glutathione, and mixed disulfide. Nitric oxide and superoxide appear to be produced in the process. Product formation is best explained by a radical mechanism in which S-nitrosation of DDC facilitates disulfide formation following homolytic cleavage. S-Nitrosocysteine and S-nitroso-N-acetylpenicillamine are likewise unstable in the presence of DDC. These findings may complicate interpretation of experiments in which DDC is used to alter NO-mediated responses. Some biological actions of DDC may result from SNO elimination rather than SOD inactivation. Moreover, apparent DDC-induced potentiation of superoxide effects may derive from O2- produced during the conversion of SNO to NO.

UI	MeSH Term	Description	Entries
D007700	Kinetics	The rate dynamics in chemical or physical systems.
D009603	Nitroso Compounds	Organic compounds containing the nitroso (-N	Compounds, Nitroso
D004050	Ditiocarb	A chelating agent that has been used to mobilize toxic metals from the tissues of humans and experimental animals. It is the main metabolite of DISULFIRAM.	Diethyldithiocarbamate,Diethylcarbamodithioic Acid,Diethyldithiocarbamic Acid,Dithiocarb,Ditiocarb Sodium,Ditiocarb, Ammonium Salt,Ditiocarb, Bismuth Salt,Ditiocarb, Lead Salt,Ditiocarb, Potassium Salt,Ditiocarb, Sodium Salt,Ditiocarb, Sodium Salt, Trihydrate,Ditiocarb, Tin(4+) Salt,Ditiocarb, Zinc Salt,Imuthiol,Sodium Diethyldithiocarbamate,Thiocarb,Zinc Diethyldithiocarbamate,Ammonium Salt Ditiocarb,Bismuth Salt Ditiocarb,Diethyldithiocarbamate, Sodium,Diethyldithiocarbamate, Zinc,Lead Salt Ditiocarb,Potassium Salt Ditiocarb,Sodium Salt Ditiocarb,Sodium, Ditiocarb,Zinc Salt Ditiocarb
D004220	Disulfides	Chemical groups containing the covalent disulfide bonds -S-S-. The sulfur atoms can be bound to inorganic or organic moieties.	Disulfide
D004221	Disulfiram	A carbamate derivative used as an alcohol deterrent. It is a relatively nontoxic substance when administered alone, but markedly alters the intermediary metabolism of alcohol. When alcohol is ingested after administration of disulfiram, blood acetaldehyde concentrations are increased, followed by flushing, systemic vasodilation, respiratory difficulties, nausea, hypotension, and other symptoms (acetaldehyde syndrome). It acts by inhibiting aldehyde dehydrogenase.	Tetraethylthiuram Disulfide,Alcophobin,Antabus,Antabuse,Anticol,Bis(diethylthiocarbamoyl) Disulfide,Dicupral,Esperal,Tetraethylthioperoxydicarbonic Diamide, ((H2N)C(S))2S2,Teturam,Disulfide, Tetraethylthiuram
D005978	Glutathione	A tripeptide with many roles in cells. It conjugates to drugs to make them more soluble for excretion, is a cofactor for some enzymes, is involved in protein disulfide bond rearrangement and reduces peroxides.	Reduced Glutathione,gamma-L-Glu-L-Cys-Gly,gamma-L-Glutamyl-L-Cysteinylglycine,Glutathione, Reduced,gamma L Glu L Cys Gly,gamma L Glutamyl L Cysteinylglycine
D013481	Superoxides	Highly reactive compounds produced when oxygen is reduced by a single electron. In biological systems, they may be generated during the normal catalytic function of a number of enzymes and during the oxidation of hemoglobin to METHEMOGLOBIN. In living organisms, SUPEROXIDE DISMUTASE protects the cell from the deleterious effects of superoxides.	Superoxide Radical,Superoxide,Superoxide Anion
D026422	S-Nitrosoglutathione	A sulfur-containing alkyl thionitrite that is one of the NITRIC OXIDE DONORS.	S-Nitroso-GSH