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S-Nitroso-L-glutathione

Cayman Chemical Item Number 82240

GSNO (CAS 57564-91-7)

S-Nitroso-L-glutathione (CAS 57564-91-7)

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Description

S-Nitroso-L-glutathione is an S-nitrosothiol NO donor based on naturally-occurring glutathione. It is a potent smooth muscle relaxant and inhibitor of platelet aggregation. Its stability in solution varies from seconds to hours depending on temperature, buffer composition, and metal content.1,2,3,4

1 Radomski, M.W., Rees, D.D., Dutra, A., et al. S-Nitroso-glutathione inhibits platelet activation in vitro and in vivo. Br J Pharmacol 107 745-749 (1992).

2 Butler, A.R., and Rhodes, P. Chemistry, analysis, and biological roles of S-nitrosothiols. Anal Biochem 249 1-9 (1997).

3 Gasco, A., Fruttero, R., and Sorba, G. NO-donors: An emerging class of compounds in medicinal chemistry. Farmaco 51 617-635 (1996).

4 Cook, J.A., Kim, S.Y., Teague, D., et al. Convenient colorimetric and fluorometric assays for S-nitrosothiols. Anal Biochem 238 150-158 (1996).

Synonyms
  • GSNO
Formal Name N-​(N-​L-​γ-​glutamyl-​S-​nitroso-​L-​cysteinyl)-​glycine
CAS Number 57564-91-7
Molecular Formula C10H16N4O7S
Formula Weight 336.3
Formulation A crystalline solid
Purity >98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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N[C@@H]​(CCC(N([H]​)​[C@H]​(CSN=O)​C(N([H]​)​CC(O)​=O)​=O)​=O)​C(O)​=O

Background Reading

Clark, A.G., and Debnam, P. Inhibition of glutathione S-transferases from rat liver by S-nitroso-L-glutathione. Biochem Pharmacol 37 3199-3201 (1988).

Gibson, A., Babbedge, R., Brave, S.R., et al. An investigation of some S-nitrosothiols, and of hydroxy-arginine, on the mouse anococcygeus. Br J Pharmacol 107 715-721 (1992).

Radomski, M.W., Rees, D.D., Dutra, A., et al. S-Nitroso-glutathione inhibits platelet activation in vitro and in vivo. Br J Pharmacol 107 745-749 (1992).

Gasco, A., Fruttero, R., and Sorba, G. NO-donors: An emerging class of compounds in medicinal chemistry. Farmaco 51 617-635 (1996).

Butler, A.R., and Rhodes, P. Chemistry, analysis, and biological roles of S-nitrosothiols. Anal Biochem 249 1-9 (1997).

Cook, J.A., Kim, S.Y., Teague, D., et al. Convenient colorimetric and fluorometric assays for S-nitrosothiols. Anal Biochem 238 150-158 (1996).

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S-Nitroso-L-glutathione is available in the following screening library:

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