S-Nitrosoglutathione
S-Nitroglutathione acts as a NO donor, displaying antioxidative, bronchodilatory, vasodilatory, and anticancer activities. In the vasculature, S-nitroglutathione attenuates Pannexin-1 channel currents and ATP release. In epithelial cells from cystic fibrosis patients, S-nitroglutathione promotes maturation of the defective CF transmembrane conductance regulator (CFTR), increasing cAMP-induced Cl- efflux and improving defective Cl- transport. Donation of NO to actin results in less effective polymerization but produces a vasodilatory effect. Additionally, donation of NO to proteins involved in insulin signal transduction improves insulin resistance. S-Nitroglutathione also stimulates activation of ERK 1/2 and p38, inducing NO-related apoptosis in colon cancer cells; in this model, glutathione and superoxide dismutase are likely to play a role as well.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18971202
| Cas No. |
57564-91-7 |
|---|---|
| Purity |
≥98% |
| Formula |
C10H16N4O7S |
| Formula Wt. |
336.32 |
| IUPAC Name |
(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-nitrososulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid |
| Melting Point |
185-195°C |
| Appearance |
Pink powder |
Lohman AW, Weaver JL, Billaud M, et al. S-nitrosylation inhibits pannexin 1 channel function. J Biol Chem. 2012 Nov 16;287(47):39602-12. PMID: 23033481.
Servetnyk Z, Krjukova J, Gaston B, et al. Activation of chloride transport in CF airway epithelial cell lines and primary CF nasal epithelial cells by S-nitrosoglutathione. Respir Res. 2006 Oct 5;7:124. PMID: 17022806.
Carvalho-Filho MA, Ueno M, Hirabara SM, et al. S-nitrosation of the insulin receptor, insulin receptor substrate 1, and protein kinase B/Akt: a novel mechanism of insulin resistance. Diabetes. 2005 Apr;54(4):959-67. PMID: 15793233.
Jeon HK, Choi SU, Jung NP. Association of the ERK1/2 and p38 kinase pathways with nitric oxide-induced apoptosis and cell cycle arrest in colon cancer cells. Cell Biol Toxicol. 2005 Mar;21(2):115-25. PMID: 16142585.
Ciriolo MR, Aquilano K, De Martino A, et al. Differential role of superoxide and glutathione in S-nitrosoglutathione-mediated apoptosis: a rationale for mild forms of familial amyotrophic lateral sclerosis associated with less active Cu,Zn superoxide dismutase mutants. J Neurochem. 2001 Jun;77(6):1433-43. PMID: 11413228.
Dalle-Donne I, Milzani A, Giustarini D, et al. S-NO-actin: S-nitrosylation kinetics and the effect on isolated vascular smooth muscle. J Muscle Res Cell Motil. 2000 Feb;21(2):171-81. PMID: 10961840.
Messmer UK, Brüne B. Nitric oxide-induced apoptosis: p53-dependent and p53-independent signalling pathways. Biochem J. 1996 Oct 1;319 ( Pt 1):299-305. PMID: 8870682.
