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2-Chloro-N6-cyclopentyladenosine

(Synonyms: 2-氯-N6-环戊基腺苷) 目录号 : GC11665

An adenosine A1 receptor antagonist

2-Chloro-N6-cyclopentyladenosine Chemical Structure

Cas No.:37739-05-2

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50mg
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产品描述

2-Chloro-N6-cyclopentyladenosine is a potent and selective agonist of adenosine A1 receptor [1].

The adenosine A1 receptor is a G protein-coupled receptor for adenosine and plays an important role in sleep promotion.

2-Chloro-N6-cyclopentyladenosine (CCPA) is a potent and selective agonist of adenosine A1 receptor. CCPA inhibited [3H]PIA binding to A1 receptors of rat brain membranes and [3H]NECA binding to A2 receptors of rat striatal membranes with Ki values of 0.4 and 3900 nM, respectively.

Also, CCPA inhibited adenylate cyclase in rat fat cell membranes with IC50 value of 33 nM and stimulated adenylate cyclase activity in human platelet membranes with EC50 value of 3500 nM [1]. In rat and bovine brain, CCPA exhibited high affinity for A1 receptors with Ki values of 1.3 and 0.5 nM, respectively. In spontaneously beating rat atria, CCPA inhibited chronotropic activity with EC50 value of 8.2 nM [2].

In ischemia/reperfusion rat model, CCPA significantly inhibited the rise of coronary perfusion pressure and diastolic pressure [2]. In rabbits, CCPA reduced mean blood pressure by 40-50% and also lowered heart rate [3]. In mice, CCPA (1.4-27.6 µmol/kg) increased [35S]TBPS binding in membranes from the substantia nigra, hippocampus, cerebral cortex and striatum mediated by A1 receptor. CCPA reduced GABA-coupled chloride channel function and induced anticonvulsant activity [4].

References:
[1].  Lohse MJ, Klotz KN, Schwabe U, et al. 2-Chloro-N6-cyclopentyladenosine: a highly selective agonist at A1 adenosine receptors. Naunyn Schmiedebergs Arch Pharmacol, 1988, 337(6): 687-689.
[2].  Monopoli A, Conti A, Dionisotti S, et al. Pharmacology of the highly selective A1 adenosine receptor agonist 2-chloro-N6-cyclopentyladenosine. Arzneimittelforschung, 1994, 44(12): 1305-1312.
[3].  Concas A, Santoro G, Mascia MP, et al. Anticonvulsant doses of 2-chloro-N6-cyclopentyladenosine, an adenosine A1 receptor agonist, reduce GABAergic transmission in different areas of the mouse brain. J Pharmacol Exp Ther, 1993, 267(2): 844-851.
[4].  Sandoli D, Chiu PJ, Chintala M, et al. In vivo and ex vivo effects of adenosine A1 and A2 receptor agonists on platelet aggregation in the rabbit. Eur J Pharmacol, 1994, 259(1): 43-49.

Chemical Properties

Cas No. 37739-05-2 SDF
别名 2-氯-N6-环戊基腺苷
化学名 (2R,3R,4S,5R)-2-(2-chloro-6-(cyclopentylamino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
Canonical SMILES ClC(N=C12)=NC(NC3CCCC3)=C2N=CN1[C@@H]([C@@H]4O)O[C@H](CO)[C@H]4O
分子式 C15H20ClN5O4 分子量 369.81
溶解度 <36.98mg/ml in ethanol; <36.98mg/ml in DMSO 储存条件 Store at -20°C
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1 mM 2.7041 mL 13.5205 mL 27.0409 mL
5 mM 0.5408 mL 2.7041 mL 5.4082 mL
10 mM 0.2704 mL 1.352 mL 2.7041 mL
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