2-Chloroadenosine

2-Chloroadenosine is an adenosine analog, a transporter permeabilizer of nucleoside transporters, and a competitive uridine influx inhibitor (apparent Ki=33 μM) . 2-Chloroadenosine binds to nitrobenzylthioinosine with high affinity (apparent Ki=0.18 mM) . 2-Chloroadenosine promotes Apoptosis and increases cerebral blood flow. 2-Chloroadenosine has anticonvulsant properties. 2-Chloroadenosine is used to study infection, inflammatory diseases, cancer, blood-related diseases, lung injury, epilepsy, and kidney disease[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17].

Product Specifications

CAS Number

[146-77-0]

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

Apoptosis; Nucleoside Antimetabolite/Analog

Type

Reference compound

Related Pathways

Apoptosis; Cell Cycle/DNA Damage

Field of Research

Cancer; Infection; Inflammation/Immunology; Neurological Disease; Cardiovascular Disease

Assay Protocol

https://www.medchemexpress.com/2-chloroadenosine.html

Purity

99.79

Solubility

DMSO : 100 mg/mL (ultrasonic) |H2O : 33.33 mg/mL (ultrasonic)

Smiles

OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C=NC3=C2N=C(Cl)N=C3N)O1

Molecular Formula

C10H12ClN5O4

Molecular Weight

301.69

Precautions

H302, H315, H319, H335

References & Citations

[1]Jarvis SM,2-Chloroadenosine, a permeant for the nucleoside transporter.Biochem Pharmacol. 1985 Sep 15;34 (18) :3237-41.|[2]Zhai XF, et al. MiR-181a contributes to bufalin-induced apoptosis in PC-3 prostate cancer cells. BMC Complement Altern Med. 2013 Nov 23;13:325.|[3]Bastin-Coyette L, et al. Mechanisms of cell death induced by 2-chloroadenosine in leukemic B-cells. Biochem Pharmacol. 2008 Apr 1;75 (7) :1451-60.|[4]Koshiba M, et al. 2-Chloroadenosine but not adenosine induces apoptosis in rheumatoid fibroblasts independently of cell surface adenosine receptor signalling. Br J Pharmacol. 2002 Mar;135 (6) :1477-86.|[5]Szondy Z. Methylprednisolone and 2-chloroadenosine induce DNA fragmentation at different stages of human T-lymphocyte development. Immunol Lett. 1997 Jun;58 (1) :59-65.|[6]Szondy Z. The 2-chlorodeoxyadenosine-induced cell death signalling pathway in human thymocytes is different from that induced by 2-chloroadenosine. Biochem J. 1995 Oct 15;311 (Pt 2) (Pt 2) :585-8.|[7]Saito T, et al. 2-Chloroadenosine: a selective lethal effect to mouse macrophages and its mechanism. J Immunol. 1985 Mar;134 (3) :1815-22.|[8]Evans MC, et al. An adenosine analogue, 2-chloroadenosine, protects against long term development of ischaemic cell loss in the rat hippocampus. Neurosci Lett. 1987 Dec 29;83 (3) :287-92.|[9]Kochanek PM, et al. Assessment of the effect of 2-chloroadenosine in normal rat brain using spin-labeled MRI measurement of perfusion. Magn Reson Med. 2001 May;45 (5) :924-9.|[10]Tse SY, et al. Inhibition of the shake response in rats by adenosine and 2-chloroadenosine. Psychopharmacology (Berl) . 1986;90 (3) :322-6.|[11]Pometlová M, et al. Effects of 2-chloroadenosine on cortical epileptic afterdischarges in immature rats. Pharmacol Rep. 2010 Jan-Feb;62 (1) :62-7.|[12]Marts BC, et al. Protective effect of 2-chloroadenosine on lung ischemia reperfusion injury. J Surg Res. 1993 Jun;54 (6) :523-9.|[13]Churchill PC. Renal effects of 2-chloroadenosine and their antagonism by aminophylline in anesthetized rats. J Pharmacol Exp Ther. 1982 Aug;222 (2) :319-23.|[14]Muhonen MG, et al. Effects of adenosine and 2-chloroadenosine on cerebral collateral vessels. J Cereb Blood Flow Metab. 1995 Nov;15 (6) :1075-81.|[15]Borowicz KK, et al. 2-Chloroadenosine, a preferential agonist of adenosine A1 receptors, enhances the anticonvulsant activity of carbamazepine and clonazepam in mice. Eur Neuropsychopharmacol. 2002 Apr;12 (2) :173-9.|[16]Kumar V, et al. Protective potential of 2-chloroadenosine in Klebsiella pneumoniae B5055 induced sepsis in BALB/c mice. Critical Care, 2008, 12: 1-1. |[17]Sakamaki F, et al. Attenuation by intravenous 2-chloroadenosine of acute lung injury induced by live escherichia coli or latex particles added to endotoxin in the neutropenic state. J Lab Clin Med. 2003 Aug;142 (2) :128-35.