N6-Cyclopentyladenosine

N6-Cyclopentyladenosine (CPA) is a selective Adenosine A1 receptor agonist, with Ki values of 2.3 nM, 790 nM and 43 nM for human A1, A2A and A3 receptors, respectively. N6-cyclopentyladenosine increases Apoptosis. N6-Cyclopentyladenosine has antitumor activity against leukemia. N6-cyclopentyladenosine improves 5-fluorouracil (HY-90006) -induced hematopoietic damage, regulates sleep, and delays Aminophylline-induced clonic epileptic seizures[1][2][3][4][5][6][7][8][9].

Product Specifications

CAS Number

[41552-82-3]

Product Name Alternative

CPA; UK-80882

UNSPSC

12352005

Target

Adenosine Receptor; Apoptosis

Type

Reference compound

Related Pathways

Apoptosis; GPCR/G Protein

Applications

Neuroscience-Neuromodulation

Field of Research

Cancer; Neurological Disease; Cardiovascular Disease

Assay Protocol

https://www.medchemexpress.com/n6-cyclopentyladenosine.html

Purity

99.95

Solubility

1 M HCl : 100 mg/mL (ultrasonic) |DMSO : 12.5 mg/mL (ultrasonic) |H2O : 2.5 mg/mL (ultrasonic; warming; heat to 60°C)

Smiles

OC[C@@H]1[C@H]([C@H]([C@H](N2C=NC3=C2N=CN=C3NC4CCCC4)O1)O)O

Molecular Formula

C15H21N5O4

Molecular Weight

335.36

References & Citations

[1]Klotz KN, et al. Adenosine receptors and their ligands. Naunyn Schmiedebergs Arch Pharmacol. 2000 Nov;362 (4-5) :382-91.|[2]Soliño M, et al. Adenosine A1 receptor: A neuroprotective target in light induced retinal degeneration. PLoS One. 2018 Jun 18;13 (6) :e0198838.|[3]Mlejnek P, et al. Apoptosis induced by N6-substituted derivatives of adenosine is related to intracellular accumulation of corresponding mononucleotides in HL-60 cells. Toxicol In Vitro. 2005 Oct;19 (7) :985-90.|[4]Pospísil M, et al. N6-cyclopentyladenosine inhibits proliferation of murine haematopoietic progenitor cells in vivo. Eur J Pharmacol. 2005 Jan 10;507 (1-3) :1-6.|[5]Schwierin B, et al. Effects of N6-cyclopentyladenosine and caffeine on sleep regulation in the rat. Eur J Pharmacol. 1996 Apr 11;300 (3) :163-71.|[6]Normile HJ, et al. N6-cyclopentyladenosine impairs passive avoidance retention by selective action at A1 receptors. Brain Res Bull. 1991 Jul;27 (1) :101-4.|[7]Mathôt RA, et al. Pharmacokinetic-pharmacodynamic relationship of the cardiovascular effects of adenosine A1 receptor agonist N6-cyclopentyladenosine in the rat. J Pharmacol Exp Ther. 1994 Feb;268 (2) :616-24.|[8]Mathôt RA, et al. Deoxyribose analogues of N6-cyclopentyladenosine (CPA) : partial agonists at the adenosine A1 receptor in vivo. Br J Pharmacol. 1995 Oct;116 (3) :1957-64.|[9]Jaishree J, et al. Individual and combined effects of N6-cyclopentyladenosine, flunarizine and diazepam on aminophylline-induced recurrent generalized seizures in mice. Pol J Pharmacol. 2003 Jul-Aug;55 (4) :559-64.