Chemical Name: N-(N-L-γ-Glutamyl-S-nitroso-L-cysteinyl)glycine
Appearance: Pink powderStorage Condition: -20ºC
Purity: ≥90.0% (HPLC)
MW: 336.32, C10H16N4O7S
Shipping Condition: protect from moisture ambient temperature
Reaction of NO release
Product Description of S-Nitrosothiols
Nitrosothiol compounds release NO and become disulfides under specific physiological conditions. While most of the S-nitrosothiol compounds are unstable, S-Nitrosoglutathione is exceptionally stable. Furthermore, S-Nitrosoglutathione is water-soluble. Although S-nitrosothiol is a good NO donor with no nitrate tolerance, there is evidence that S-nitrosothiol itself has NO-like activity during guanylate cyclase activation. Another important reaction of nitrosothiol is NO transfer to other thiol compounds. Since it depends on the pKa of thiols, this transfer reaction proceeds at physiological pH levels. The relaxation efficiency of these nitrosothiol has been compared using rataprta ring samples:SNAP > S - N i t r o s o g l u t a t h i o n e = S - N i t r o s o - N -acetylcysteine>S-Nitrosocoenzyme A>S-Nitroso-L-cysteine. Dr. Kowaluk and others reported that the spontaneous liberation of NO from SNAP could not account for in vitro vascular relaxation. The spontaneous release of NO from nitrosothiol compounds may not be a key element of vascular relaxation. Metabolites of nitrosothiol generated at the cell membrane might be the essential element for relaxation.
1. A. Gibson, et al., An Investigation of Some S-Nitrosothiols, and of Hydroxy-arginine, on the Mouse Anococcygeus. Br J Pharmacol. 1992;107:715-721.
2. M. W. Radomski, et al., S-Nitroso-glutathione Inhibits Platelet Activation in Vitro and in Vivo. Br J Pharmacol. 1992;107:745-749.
3. R. M. Clancy, et al., Novel Synthesis of S-Nitrosoglutathione and Degradation by Human Neutrophils. Anal Biochem. 1992;204:365-371.
4. J. W. Park, et al., Transnitrosation as a Predominant Mechanism in the Hypotensive Effect of S-Nitrosoglutathione. Biochem Mol Biol Int. 1993;30:885-891.
5. D. Barrachina, et al., Nitric Oxide Donors Preferencially Inhibit Neuronally Mediated Rat Gastric Acid Secretion. Eur J Pharmacol. 1994;262:181-183.
6. E. A. Konorev, et al., S-Nitrosoglutathione Improves Functional Recovery in the Isolated Rat Heart After Cardioplegic Ischemic Arrest-evidence for a Cardioprotective Effect of Nitric Oxide. J Pharmacol Exp Ther. 1995;274:200-2006.
7. S. C. Askew, et al., Catalysis by Cu2+ of Nitric Oxide Release from S-Nitrosothiols (RSNO). J Chem Soc Perkin Trans 2. 1995;741-745.
8. D. J. Banett, et al., NO-group Transfer(Transnitrosation) between S-Nitrosothiols and Thiols. Part 2. J Chem Soc Perkin Trans 2. 1995;1279-1282.
9. J. G. De Man, et al., Effect of Cu2+ on Relaxations to the Nitrergic Neurotransmitter, NO and S-Nitrosothiols in the Rat Gastric Fundus. Br J Pharmacol. 1996;119:990-996.
10. A. P. Dicks, et al., Generation of Nitric Oxide from S-Nitrosothiols Using Protein-bound Cu2+ Sources. Chem Biol. 1996;3:655-659.
11. J. A. Cook, et al., Convenient Colorimetric and Fluorometric Assays for S-Nitrosothiols. Anal Biochem. 1996;238:150-158.
12. S. X. Liu, et al., Nitric Oxide Donors: Effects of S-Nitrosoglutathione and 4-Phenyl-3-furoxancarbonitrile on Ocular Blood Flow and Retinal Function Recovery. J Ocul Pharmacol Ther. 1997;13:105-114.
13. C. Alpert, et al., Detection of S-Nitrosothiols and Other Nitric Oxide Derivatives by Photolysis-chemiluminescence Spectrometry. Anal Biochem. 1997;245:1-7.
14. T. Akaike, et al., Nanomolar Quantification and Identification of Various Nitrosothiols by High Performance Liquid Chromatography Coupled with Flow Reactors of Metals and Griess Reagent. J Biochem. 1997;122:459-466.