L-γ-Glutamyl-S-nitroso-L-cysteinylglycine

Names

[ Name ]:
L-γ-Glutamyl-S-nitroso-L-cysteinylglycine

[Synonym ]:
L-γ-Glutamyl-S-nitroso-L-cysteinylglycine
glycine, N-(N-L-γ-glutamyl-S-nitroso-L-cysteinyl)-
Glycine, L-γ-glutamyl-S-nitroso-L-cysteinyl-
S-Nitroso-L-glutathione
S-NITROSOGLUTATHIONE
MFCD00214341
EINECS 248-170-7

Biological Activity

[Description]:

Nitrosoglutathione (GSNO), a exogenous NO donor and a substrate for rat alcohol dehydrogenase class III isoenzyme, inhibits cerebrovascular angiotensin II-dependent and -independent AT1 receptor responses[1][2][3][4].

[Related Catalog]:

Research Areas >> Cardiovascular Disease

Research Areas >> Inflammation/Immunology

Signaling Pathways >> GPCR/G Protein >> Angiotensin Receptor

[In Vitro]

Nitrosoglutathione (GSNO, 250 μM) prevents 90% of the response to 0.1 μM 5-HT and 40% of the response to 1.0 μM 5-HT in rings treated with LY-83583, indicating an effect of GSNO that was independent of guanylate cyclase activity[5].

[In Vivo]

Nitrosoglutathione (GSNO, 8 mg/kg) significantly decreases systolic, diastolic, and mean arterial pressures in PE-induced rats from day 14 through day 20[3]. Nitrosoglutathione (GSNO, 0.2 and 0.6 mg/kg) significantly inhibits superoxide production and suppressed NF-κB activation, iNOS induction, and 3-nitrotyrosine expression, butup-regulates endothelial NOS expression in the flap vessels[4]. Animal Model: Male Lewis rats[4]. Dosage: 0.2 and 0.6 mg/kg. Administration: Slow intravenous injection via the opposite femoral vein into each rat. Result: Animals treated with 0.2 mg of GSNO per kilogram before reperfusion had an intermediate survival rate (40.2 ± 4.9%). Although 0.6 mg/kg of GSNO showed a better rescuing effect than 150 mg/kg of NAC, there was no significant difference between the groups.

[References]

[1]. Marie-Lynda Bouressam, et al. S-nitrosoglutathione inhibits cerebrovascular angiotensin II-dependent and -independent AT 1 receptor responses: A possible role of S-nitrosation. Br J Pharmacol. 2019 Jun;176(12):2049-2062.

[2]. D E Jensen, et al. S-Nitrosoglutathione is a substrate for rat alcohol dehydrogenase class III isoenzyme. Biochem J. 1998 Apr 15;331 ( Pt 2)(Pt 2):659-68.

[3]. Caneta Brown, et al. The effects of S-nitrosoglutathione and S-nitroso-N-acetyl-D, L-penicillamine in a rat model of pre-eclampsia. J Nat Sci Biol Med. 2013 Jul;4(2):330-5.

[4]. Yur-Ren Kuo, et al. Nitrosoglutathione promotes flap survival via suppression of reperfusion injury-induced superoxide and inducible nitric oxide synthase induction. J Trauma. 2004 Nov;57(5):1025-31.

[5]. Eva Nozik-Grayck, et al. Pulmonary vasoconstriction by serotonin is inhibited by S-nitrosoglutathione. Am J Physiol Lung Cell Mol Physiol. 2002 May;282(5):L1057-65.

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Melting Point ]:
>170ºC (dec.)

[ Molecular Formula ]:
C₁₀H₁₆N₄O₇S

[ Molecular Weight ]:
336.322

[ Exact Mass ]:
336.073975

[ PSA ]:
213.55000

[ LogP ]:
-0.26

[ Index of Refraction ]:
1.656

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: MC0558000

CHEMICAL NAME :: Glycine, N-(N-L-gamma-glutamyl-2-nitroso-L-cysteinyl)-

CAS REGISTRY NUMBER :: 57564-91-7

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C10-H16-N4-O7-S

MOLECULAR WEIGHT :: 336.36

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Salmonella typhimurium

DOSE/DURATION :: 5 umol/plate

REFERENCE :: BCPCA6 Biochemical Pharmacology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1958- Volume(issue)/page/year: 35,3847,1986

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
MC0558000

[ HS Code ]:
2930909090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2930909090

[ Summary ]:
2930909090. other organo-sulphur compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Down regulation of NO signaling in Trypanosoma cruzi upon parasite-extracellular matrix interaction: changes in protein modification by nitrosylation and nitration.

PLoS Negl. Trop. Dis. 9 , e0003683, (2015)

Adhesion of the Trypanosoma cruzi trypomastigotes, the causative agent of Chagas' disease in humans, to components of the extracellular matrix (ECM) is an important step in host cell invasion. The sig...

Lipopolysaccharides Promote S-Nitrosylation and Proteasomal Degradation of Liver Kinase B1 (LKB1) in Macrophages in Vivo.

J. Biol. Chem. 290 , 19011-7, (2015)

LKB1 (liver kinase B1) plays important roles in tumor suppression, energy metabolism, and, recently, in innate immune responses. However, how LKB1 is regulated under physiological or pathological cond...

S-nitrosylation triggers ABI5 degradation to promote seed germination and seedling growth.

Nat. Commun. 6 , 8669, (2015)

Plant survival depends on seed germination and progression through post-germinative developmental checkpoints. These processes are controlled by the stress phytohormone abscisic acid (ABA). ABA regula...