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(±)-5'-Chloro-5'-deoxy-ENBA

adenosine A1 receptor agonist, selective and high-affinity CAS# 103626-26-2

(±)-5'-Chloro-5'-deoxy-ENBA

Catalog No. BCC7716----Order now to get a substantial discount!

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(±)-5'-Chloro-5'-deoxy-ENBA: 5mg $115 In Stock
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Chemical structure

(±)-5'-Chloro-5'-deoxy-ENBA

3D structure

Chemical Properties of (±)-5'-Chloro-5'-deoxy-ENBA

Cas No. 103626-26-2 SDF Download SDF
PubChem ID 15599147 Appearance Powder
Formula C17H22ClN5O3 M.Wt 379.84
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble to 100 mM in DMSO and to 100 mM in ethanol
Chemical Name 2-[6-(3-bicyclo[2.2.1]heptanylamino)purin-9-yl]-5-(chloromethyl)oxolane-3,4-diol
SMILES C1CC2CC1CC2NC3=NC=NC4=C3N=CN4C5C(C(C(O5)CCl)O)O
Standard InChIKey PVJGDYDNVNCGBT-UHFFFAOYSA-N
Standard InChI InChI=1S/C17H22ClN5O3/c18-5-11-13(24)14(25)17(26-11)23-7-21-12-15(19-6-20-16(12)23)22-10-4-8-1-2-9(10)3-8/h6-11,13-14,17,24-25H,1-5H2,(H,19,20,22)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of (±)-5'-Chloro-5'-deoxy-ENBA

DescriptionHighly selective adenosine A1 receptor agonist (Ki values are 0.51, 1290, 1340 and 2740 nM at A1, A3, A2A and A2B receptors respectively). Reverses formaline-induced nocifensive behavior in mice; antinociceptive.

(±)-5'-Chloro-5'-deoxy-ENBA Dilution Calculator

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(±)-5'-Chloro-5'-deoxy-ENBA Molarity Calculator

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Preparing Stock Solutions of (±)-5'-Chloro-5'-deoxy-ENBA

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.6327 mL 13.1634 mL 26.3269 mL 52.6537 mL 65.8172 mL
5 mM 0.5265 mL 2.6327 mL 5.2654 mL 10.5307 mL 13.1634 mL
10 mM 0.2633 mL 1.3163 mL 2.6327 mL 5.2654 mL 6.5817 mL
50 mM 0.0527 mL 0.2633 mL 0.5265 mL 1.0531 mL 1.3163 mL
100 mM 0.0263 mL 0.1316 mL 0.2633 mL 0.5265 mL 0.6582 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on (±)-5'-Chloro-5'-deoxy-ENBA

(±)-5'-Chloro-5'-deoxy-ENBA is a selective and high-affinity adenosine A1 receptor agonist with Ki values of 0.51 [1].
Adenosine A1 receptor mediated neuroand cardioprotection (an antiarrhythmic effect), reduction of lipolysis in adipose tissue and reduction of neuropathic pain [1].
In mice injected with formalin at doses between 1 and 2mg/kg, (±)-5'-Chloro-5'-deoxy-ENBA inhibited the first and the second phases of the nocifensive response induced by formalin [1]. In a mouse model of neuropathic pain (the Spared Nerve Injury (SNI) of the sciatic nerve), (±)-5'-Chloro-5'-deoxy-ENBA (0.5 mg/kg) reduced thermal hyperalgesia and mechanical allodynia 7 and 3 days post-SNI without significantly changed the motor coordination and arterial blood pressure. Also, (±)-5'-Chloro-5'-deoxy-ENBA chronic treatment reduced activated and hypertrophic microglia [2]. In a Parkinson's disease (PD) mouse model, (±)-5'-Chloro-5'-deoxy-ENBA prevented the increase in sIPSC frequency and eIPSC amplitude produced by SKF. In mice with unilateral DA denervation, (±)-5'-Chloro-5'-deoxy-ENBA reduced the development of abnormal involuntary movements induced by L-DOPA [3].
References:
[1]. Franchetti P, Cappellacci L, Vita P, Petrelli R, et al. N6-Cycloalkyl- and N6-bicycloalkyl-C5'(C2')-modified adenosine derivatives as high-affinity and selective agonists at the human A1 adenosine receptor with antinociceptive effects in mice. J Med Chem, 2009, 52(8): 2393-2406.
[2]. Luongo L, Petrelli R, Gatta L, et al. 5'-Chloro-5'-deoxy-(±)-ENBA, a potent and selective adenosine A(1) receptor agonist, alleviates neuropathic pain in mice through functional glial and microglial changes without affecting motor or cardiovascular functions. Molecules, 2012, 17(12): 13712-13726.
[3]. Mango D, Bonito-Oliva A, Ledonne A, et al. Adenosine A1 receptor stimulation reduces D1 receptor-mediated GABAergic transmission from striato-nigral terminals and attenuates l-DOPA-induced dyskinesia in dopamine-denervated mice. Exp Neurol, 2014, 261: 733-743.

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References on (±)-5'-Chloro-5'-deoxy-ENBA

5'-Chloro-5'-deoxy-(+/-)-ENBA, a potent and selective adenosine A(1) receptor agonist, alleviates neuropathic pain in mice through functional glial and microglial changes without affecting motor or cardiovascular functions.[Pubmed:23174891]

Molecules. 2012 Nov 22;17(12):13712-26.

This study was undertaken in order to investigate the effect of chronic treatment with 5′-chloro-5′-deoxy-(±)-ENBA, a potent and highly selective agonist of human adenosine A(1) receptor, on thermal hyperalgesia and mechanical allodynia in a mouse model of neuropathic pain, the Spared Nerve Injury (SNI) of the sciatic nerve. Chronic systemic administration of 5′-chloro-5′-deoxy-(±)-ENBA (0.5 mg/kg, i.p.) reduced both mechanical allodynia and thermal hyperalgesia 3 and 7 days post-SNI, in a way prevented by DPCPX (3 mg/kg, i.p.), a selective A(1) adenosine receptor antagonist, without exerting any significant change on the motor coordination or arterial blood pressure. In addition, a single intraperitoneal injection of 5′-chloro-5′-deoxy-(±)-ENBA (0.5 mg/kg, i.p.) 7 days post-SNI also reduced both symptoms for at least two hours. SNI was associated with spinal changes in microglial activation ipsilaterally to the nerve injury. Activated, hypertrophic microglia were significantly reduced by 5′-chloro-5′-deoxy-(±)-ENBA chronic treatment. Our results demonstrated an involvement of adenosine A(1) receptor in the amplified nociceptive thresholds and in spinal glial and microglial changes occurred in neuropathic pain, without affecting motor coordination or blood pressure. Our data suggest a possible use of adenosine A(1) receptor agonist in neuropathic pain symptoms.

Tremorolytic effect of 5'-chloro-5'-deoxy-(+/-)-ENBA, a potent and selective adenosine A1 receptor agonist, evaluated in the harmaline-induced model in rats.[Pubmed:28371468]

CNS Neurosci Ther. 2017 May;23(5):438-446.

AIM: The aim of this study was to examine the role of adenosine A1 receptors in the harmaline-induced tremor in rats using 5'-chloro-5'-deoxy-(+/-)-ENBA (5'Cl5'd-(+/-)-ENBA), a brain-penetrant, potent, and selective adenosine A1 receptor agonist. METHODS: Harmaline was injected at a dose of 15 mg/kg ip and tremor was measured automatically in force-plate actimeters by an increased averaged power in the frequency band of 9-15 Hz (AP2) and by tremor index (a difference in power between AP2 and averaged power in the frequency band of 0-8 Hz). The zif-268 mRNA expression was additionally analyzed by in situ hybridization in several brain structures. RESULTS: 5'Cl5'd-(+/-)-ENBA (0.05-0.5 mg/kg ip) dose dependently reduced the harmaline-induced tremor and this effect was reversed by 8-cyclopentyl-1,3-dipropylxanthine (DPCPX), a selective antagonist of adenosine A1 receptors (1 mg/kg ip). Harmaline increased the zif-268 mRNA expression in the inferior olive, cerebellar cortex, ventroanterior/ventrolateral thalamic nuclei, and motor cortex. 5'Cl5'd-(+/-)-ENBA reversed these increases in all the above structures. DPCPX reduced the effect of 5'Cl5'd-(+/-)-ENBA on zif-268 mRNA in the motor cortex. CONCLUSION: This study suggests that adenosine A1 receptors may be a potential target for the treatment of essential tremor.

N6-Cycloalkyl- and N6-bicycloalkyl-C5'(C2')-modified adenosine derivatives as high-affinity and selective agonists at the human A1 adenosine receptor with antinociceptive effects in mice.[Pubmed:19317449]

J Med Chem. 2009 Apr 23;52(8):2393-406.

To further investigate new potent and selective human A(1) adenosine receptor agonists, we have synthesized a series of 5'-chloro-5'-deoxy- and 5'-(2-fluorophenylthio)-5'-deoxy-N(6)-cycloalkyl(bicycloalkyl)-substituted adenosine and 2'-C-methyladenosine derivatives. These compounds were evaluated for affinity and efficacy at human A(1), A(2A), A(2B), and A(3) adenosine receptors. In the series of N(6)-cyclopentyl- and N(6)-(endo-norborn-2-yl)adenosine derivatives, 5'-chloro-5'-deoxy-CPA (1) and 5'-chloro-5'-deoxy-(+/-)-ENBA (3) displayed the highest affinity in the subnanomolar range and relevant selectivity for hA(1) vs the other human receptor subtypes. The higher affinity and selectivity of 5'-chloro-5'-deoxyribonucleoside derivatives 1 and 3 for hA(1) AR vs hA(3) AR compared to that of the parent 5'-hydroxy compounds CPA and (+/-)-ENBA was rationalized by a molecular modeling analysis. 5'-Chloro-5'-deoxy-(+/-)-ENBA, evaluated for analgesic activity in the formalin test in mice, was found to inhibit the first or the second phases of the nocifensive response induced by intrapaw injection of formalin at doses ranging between 1 and 2 mg/kg i.p.

Description

Highly selective A1 agonist

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