119140

NECA

≥99% (HPLC), solid, adenosine receptor agonist, Calbiochem^®

• Synonyme(s) : Adenosine Receptor Agonist, NECA, (2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-N-ethyl-3,4-dihydroxytetrahydrofuran-2-carboxamide
• Formule empirique (notation de Hill) : C₁₂H₁₆N₆O₄
• Numéro CAS: 35920-39-9
• Poids moléculaire : 308.29
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD00069195
• Assay: ≥99% (HPLC)
• Form: solid
• Storage condition: OK to freeze, protect from light

Propriétés

• Nom du produit: Adenosine Receptor Agonist, NECA,
• assay: ≥99% (HPLC)
• Quality Segment: 100
• form: solid
• potency: 14 nM K_i
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, protect from light
• color: white
• solubility: DMSO: 50 mM
• shipped in: wet ice
• storage temp.: 2-8°C
• SMILES string: [n]2(c3ncnc(c3nc2)N)C1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC
• InChI: 1S/C12H16N6O4/c1-2-14-11(21)8-6(19)7(20)12(22-8)18-4-17-5-9(13)15-3-16-10(5)18/h3-4,6-8,12,19-20H,2H2,1H3,(H,14,21)(H2,13,15,16)/t6-,7+,8-,12?/m0/s1
• InChI key: JADDQZYHOWSFJD-QQIVLSGASA-N

Description

General description

A cell-permeable adenosine analog that acts a potent non-selective agonist of adenosine receptors (K_i = 14 nM, 20 nM, 2.4 µM and 6.2 nM for A₁, A_2A, A_2B, A₃, respectively). Increases intracellular cAMP production (EC₅₀ = 3.1 µM in A_2B expressing CHO cells). Shown to increase glucagon release in a dose-dependent manner and inhibit insulin release at low concentrations. Although at higher concentration some insulin release is observed. Also, displays a wide range adenosine-dependent effects, such as blocking platelet aggregation and inhibiting DNA synthesis. When administered at reperfusion, it is shown reduce infarction and block the formation of the mitochondrial permeability transition pore by activating p70S6 kinase.

Biochem/physiol Actions

Reversible: yes

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Forster, K., et al. 2006. Basic Res. Cardiol.101, 319.
de Zwart, M., et al. 1998. Nucleosides Nucleotides.17, 969.
Phillis, J. et al. 1986, Pharm. Biochem. Behavior.24, 263
Durcan, M. J., et al. 1989. Pharmacol Biochem Behav.32, 487.
Bacher, S., et al. 1982. Naunyn Schmiedebergs Arch Pharmacol.329, 67.
Cusack, N., et al. 1981. Br J Pharm.72, 443.
Londos, C., et al. 1980. Proc Natl Acad Sci.77, 2551.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Informations sur la sécurité

• Pictogrammes: GHS06
• Mot-clé: Danger
• Codes de danger: H300
• Mentions de précaution: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 2 Oral
• Classe de stockage: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• Que se passe-t-il ?: WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable