N-Acetyl-3-(nitrososulfanyl)valine

Names

[ Name ]:
N-Acetyl-3-(nitrososulfanyl)valine

[Synonym ]:
MFCD00272624
N-Acetyl-3-(nitrososulfanyl)valine
Valine, N-acetyl-3-(nitrosothio)-
snap

Biological Activity

[Description]:

S-Nitroso-N-acetyl-DL-penicillamine (SNAP) is a nitric oxide donor and acts as a stable inhibitor of platelet aggregation[1][2][3][4].

[Related Catalog]:

Research Areas >> Cardiovascular Disease

Signaling Pathways >> Immunology/Inflammation >> NO Synthase

[In Vitro]

S-Nitroso-N-acetyl-DL-penicillamine (10 mM; 8 hours) induces toxicity of about 80% after 6 hours under normoxic conditions by releasing nitric oxide (NO)[1]. S-Nitroso-N-acetyl-DL-penicillamine has a half-time about 6 hours in in isolated rat ventricular myocytes[3]. S-Nitroso-N-acetyl-DL-penicillamine (100 µM; 30 minutes) causes sustained decrease in the basal pHi in isolated rat ventricular myocytes[3]. Cell Viability Assay[1] Cell Line: Rat liver sinusoidal endothelial cells Concentration: 2 mM, 5 mM, 10 mM Incubation Time: 2 hours, 4 hours, 6 hours, 8 hours Result: Exhibited cytotoxicity against cultivated endothelial cells.

[In Vivo]

SNAP (100μM, 300μM) causes small but significant increases of the electrically evoked [3H]-acetylcholine release in guinea-pig tracheal[4].

[References]

[1]. E. Salas, et al. Comparative pharmacology of analogues of S-nitroso-N-acetyl-DL-penicillamine on human platelets. Br J Pharmacol. 1994 Aug;112(4):1071-6.

[2]. Ioannidis I, et al. Enhanced release of nitric oxide causes increased cytotoxicity of S-nitroso-N-acetyl-DL-penicillamine and sodium nitroprusside under hypoxic conditions. Biochem J. 1996 Sep 15;318 ( Pt 3):789-95.

[3]. Pravdic D, et al. Effect of nitric oxide donors S-nitroso-N-acetyl-DL-penicillamine, spermine NONOate and propylamine propylamine NONOate on intracellular pH in cardiomyocytes. Clin Exp Pharmacol Physiol. 2012 Sep;39(9):772-8.

[4]. Mang CF, et al. Modulation of acetylcholine release in the guinea-pig trachea by the nitric oxide donor, S-nitroso-N-acetyl-DL-penicillamine (SNAP). Br J Pharmacol. 2000 Sep;131(1):94-8.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Melting Point ]:
151ºC

[ Molecular Formula ]:
C₇H₁₂N₂O₄S

[ Molecular Weight ]:
220.246

[ Exact Mass ]:
220.051773

[ PSA ]:
121.13000

[ LogP ]:
1.13

[ Index of Refraction ]:
1.560

[ Storage condition ]:
−20°C

[ Water Solubility ]:
H2O: ≥2 mg/mL

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

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Aerobic exercise training prevents heart failure-induced skeletal muscle atrophy by anti-catabolic, but not anabolic actions.

PLoS ONE 9(10) , e110020, (2014)

Heart failure (HF) is associated with cachexia and consequent exercise intolerance. Given the beneficial effects of aerobic exercise training (ET) in HF, the aim of this study was to determine if the ...

Interferon-gamma induced cell death: Regulation and contributions of nitric oxide, cJun N-terminal kinase, reactive oxygen species and peroxynitrite.

Biochim. Biophys. Acta 1843(11) , 2645-61, (2014)

Interferon-gamma (Ifnγ), a known immunomodulatory cytokine, regulates cell proliferation and survival. In this study, the mechanisms leading to the selective susceptibility of some tumor cells to Ifnγ...

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...