N4148

Sigma-Aldrich

S-Nitrosoglutathione

≥97%

Synonym(s):
GSNO, SNOG
Empirical Formula (Hill Notation):
C10H16N4O7S
CAS Number:
Molecular Weight:
336.32
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

assay

≥97%

form

powder

solubility

water: soluble 19.60-20.40 mg/mL

storage temp.

−20°C

SMILES string

N[C@@H](CCC(=O)N[C@@H](CSN=O)C(=O)NCC(O)=O)C(O)=O

InChI

1S/C10H16N4O7S/c11-5(10(19)20)1-2-7(15)13-6(4-22-14-21)9(18)12-3-8(16)17/h5-6H,1-4,11H2,(H,12,18)(H,13,15)(H,16,17)(H,19,20)/t5-,6-/m0/s1

InChI key

HYHSBSXUHZOYLX-WDSKDSINSA-N

General description

S-Nitrosoglutathione (GSNO) is an endogenous nitrogen oxide and is highly distributed in extracellular fluids of the lung and brain.

Application

S-Nitrosoglutathione (GSNO) has been used:
  • as a standard in reversed phase chromatography coupled to chemical vapour generation and atomic fluorescence detector (RPC-CVGAFS) and reversed phase chromatography fluorimetric (RPC-FD).
  • as a standard in spectrophotometric and high-performance liquid chromatography (HPLC) assay.

Packaging

25 mg in poly bottle
50 mg in glass bottle

Biochem/physiol Actions

S-Nitrosoglutathione (GSNO) inhibits the activity of sarcoplasmic reticulum-bound creatine kinase in rabbit skeletal muscle and eventually reduces ATP driven Ca2+ uptake in sarcoplasmic reticulum vesicles. GSNO in airway cells relaxes airway smooth muscle and enhances airway ciliary motility. It also blocks airway epithelial amiloride-sensitive sodium transport while stimulating calcium-dependent epithelial chloride transport and induces neutrophilic apoptosis. In addition, it also has antimicrobial activity. GSNO concentration is low in cystic fibrosis (CF) airway. It is an NO donor, acts as a smooth muscle relaxant, vasodilator and inhibits platelet activation in vivo.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

C C Chiueh et al.
Free radical research, 31(6), 641-650 (2000-01-12)
Recent results demonstrated that S-nitrosoglutathione (GSNO) and nitric oxide (*NO) protect brain dopamine neurons from hydroxyl radical (*OH)-induced oxidative stress in vivo because they are potent antioxidants. GSNO and *NO terminate oxidant stress in the brain by (i) inhibiting iron-stimulated...
Inhibition of creatine kinase by S-nitrosoglutathione.
Wolosker H
Febs Letters, 392(3), 274-276 (1996)
C A Staab et al.
Cellular and molecular life sciences : CMLS, 65(24), 3950-3960 (2008-11-18)
Alcohol dehydrogenase 3 (ADH3) is highly conserved, ubiquitously expressed in mammals and involved in essential cellular pathways. A large active site pocket entails special substrate specificities: shortchain alcohols are poor substrates, while medium-chain alcohols and particularly the glutathione adducts S-hydroxymethylglutathione...
Acute effects of aerosolized S-nitrosoglutathione in cystic fibrosis.
Snyder AH
American Journal of Respiratory and Critical Care Medicine, 165(7), 922-926 (2002)
A kinetic study of gamma-glutamyltransferase (GGT)-mediated S-nitrosoglutathione catabolism.
Angeli V
Archives of Biochemistry and Biophysics, 481(2), 191-196 (2009)

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