119140

NECA

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

• Synonyma: Adenosine Receptor Agonist, NECA, (2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-N-ethyl-3,4-dihydroxytetrahydrofuran-2-carboxamide
• Empirický vzorec (Hillův zápis): C₁₂H₁₆N₆O₄
• Číslo CAS: 35920-39-9
• Molekulová hmotnost: 308.29
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD00069195

Vlastnosti

• Název produktu: Adenosine Receptor Agonist, NECA,
• 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
• assay: ≥99% (HPLC)
• 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
• Quality Level: 100

Popis

Biochem/physiol Actions

Reversible: yes

Disclaimer

Toxicity: Standard Handling (A)

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.

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.

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.

Legal Information

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

Bezpečnostní informace

• pictograms: GHS06
• signalword: Danger
• hcodes: H300
• pcodes: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 2 Oral
• Skladovací třída: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable