288104

2′,5′-Dideoxyadenosine

Cell-permeable, non-competitive adenylate cyclase inhibitor (IC50 = 3 µM), that binds to the adenosine P1 binding site.

• Synonym(s): 2′,5′-Dideoxyadenosine, 2ʹ,5ʹ-dd-Ado
• Empirical Formula (Hill Notation): C₁₀H₁₃N₅O₂
• CAS Number: 6698-26-6
• Molecular Weight: 235.24
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD00210904
• Assay: ≥98% (HPLC)
• Form: solid
• Storage condition: OK to freeze

Properties

• Quality Segment: 100
• assay: ≥98% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: white
• solubility: DMSO: 10 mg/mL
• shipped in: ambient
• storage temp.: 2-8°C
• SMILES string: [n]2(c3ncnc(c3nc2)N)[C@@H]1O[C@@H]([C@H](C1)O)C
• InChI: 1S/C10H13N5O2/c1-5-6(16)2-7(17-5)15-4-14-8-9(11)12-3-13-10(8)15/h3-7,16H,2H2,1H3,(H2,11,12,13)/t5-,6+,7-/m1/s1
• InChI key: FFHPXOJTVQDVMO-DSYKOEDSSA-N

Description

General description

Cell-permeable, non-competitive adenylate cyclase inhibitor (IC₅₀ = 3 µM), that binds to the adenosine P1 binding site. Blocks positive inotropic and chronotropic effects of β-adrenergic agents.

Membrane-permeable adenylate cyclase inhibitor that binds non-competitively to the enzyme via the P-site. Its inhibitory effect varies widely among tissues (IC₅₀ = 3 µM for detergent solubilized rat brain membranes; IC₅₀ = 45 µM for purified bovine brain enzyme). Blocks the forskolin-induced activation of adenylate cyclase activity (IC₅₀ = 540 µM) in cultured bovine aortic endothelial cells. Also blocks the positive ionotropic and chronotropic effects of β-adrenergic agents.

Biochem/physiol Actions

Cell permeable: yes

Product does not compete with ATP.

Reversible: no

Target IC₅₀: 3 µM against adenylate cyclase

Other Notes

Ibrahimi, A., et al. 1999. Am. J. Physiol.276, C487.
Hartman, M., and Schrader, J. 1995. J. Mol. Cell. Cardiol. 25, 331.
Bushfield, M., et al. 1990. Mol. Pharmacol.38, 848.
Reid, I.R., et al. 1990. Am. J. Physiol.258, E708.
Legrand, A.B., et al. 1990. Biochem. Pharmacol.40, 1103.
Johnson, R.A., et al. 1989. Mol. Pharmacol.35, 681.
Holgate, S.T., et al. 1980. Proc. Natl. Acad. Sci. USA77, 6800.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable