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Submit Review(±)-5'-Chloro-5'-deoxy-ENBA
Description: Highly selective A1 agonist
Chemical Name: N-Bicyclo[2.2.1]hept-2-yl-5'-chloro-5'-deoxyadenosine
Purity: ≥98% (HPLC)
Biological Activity for (±)-5'-Chloro-5'-deoxy-ENBA
(±)-5'-Chloro-5'-deoxy-ENBA is a highly selective adenosine A1 receptor agonist (Ki values are 0.51, 1290, 1340 and 2740 nM at A1, A3, A2A and A2B receptors respectively). Reverses formalin-induced nocifensive behavior in mice; antinociceptive.
Compound Libraries for (±)-5'-Chloro-5'-deoxy-ENBA
(±)-5'-Chloro-5'-deoxy-ENBA is also offered as part of the Tocriscreen 2.0 Max. Find out more about compound libraries available from Tocris.
Technical Data for (±)-5'-Chloro-5'-deoxy-ENBA
| M. Wt | 379.84 |
| Formula | C17H22ClN5O3 |
| Storage | Store at -20°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 103626-26-2 |
| PubChem ID | 42636897 |
| InChI Key | PVJGDYDNVNCGBT-STHLEMNDSA-N |
| Smiles | O[C@@H]1[C@H](O)[C@@H](CCl)O[C@H]1N(C=N3)C2=C3C(NC4C5CCC(C5)C4)=NC=N2 |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for (±)-5'-Chloro-5'-deoxy-ENBA
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 37.98 | 100 | |
| ethanol | 37.98 | 100 |
Preparing Stock Solutions for (±)-5'-Chloro-5'-deoxy-ENBA
The following data is based on the product molecular weight 379.84. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 2.63 mL | 13.16 mL | 26.33 mL |
| 5 mM | 0.53 mL | 2.63 mL | 5.27 mL |
| 10 mM | 0.26 mL | 1.32 mL | 2.63 mL |
| 50 mM | 0.05 mL | 0.26 mL | 0.53 mL |
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Product Datasheets for (±)-5'-Chloro-5'-deoxy-ENBA
References for (±)-5'-Chloro-5'-deoxy-ENBA
References are publications that support the biological activity of the product.
Trivedi et al (1989) N6-bicycloalkyladenosines with unusually high potency and selectivity for the adenosine A1 receptor. J.Med.Chem. 32 8 PMID: 2909748
Franchetti et al (2009) 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. 52 2393 PMID: 19317449
If you know of a relevant reference for (±)-5'-Chloro-5'-deoxy-ENBA, please let us know.
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Keywords: (±)-5'-Chloro-5'-deoxy-ENBA, (±)-5'-Chloro-5'-deoxy-ENBA supplier, highly, selective, A1, adenosines, receptors, agonists, (±)-5-Chloro-5-deoxy-ENBA, ENBA, Adenosine, Receptors, 3576, Tocris Bioscience
2 Citations for (±)-5'-Chloro-5'-deoxy-ENBA
Citations are publications that use Tocris products. Selected citations for (±)-5'-Chloro-5'-deoxy-ENBA include:
Cuiying et al (2020) Activation of neuronal adenosine A1 receptors causes hypothermia through central and peripheral mechanisms. PLoS One 15 e0243986 PMID: 33326493
Wei et al (2021) Adenosine A2A Receptor Activation Enhances Blood-Tumor Barrier Permeability in a Rodent Glioma Model. Mol Cancer Res 19 2081-2095 PMID: 34521765
Do you know of a great paper that uses (±)-5'-Chloro-5'-deoxy-ENBA from Tocris? Please let us know.
Reviews for (±)-5'-Chloro-5'-deoxy-ENBA
Average Rating: 5 (Based on 1 Review.)
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Antinociceptive assay and for reducing the development of abnormal involuntary movements L-DOPA induced.
By
Anonymous on 01/08/2018
Assay Type: In Vivo
Species: Mouse
Cell Line/Tissue: CHO cells
In the first work, we demonstrated that 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 A1 adenosine receptor antagonist, without exerting any significant change on the motor coordination or arterial blood pressure (Molecules. 2012, 17, 13712-13726. doi: 10.3390/molecules171213712).Then, the product has been used to clearly demonstrate that functionalA1ARs are expressed in microglia (Glia. 2014, 62,122-132. doi: 10.1002/glia.22592).In addition, we found that 5′Cl5′ d-(±)-ENBA, administered in combination with L-DOPA, reduced the development of abnormal involuntary movements. These results indicate the potential benefit of A1R agonists for the treatment of L-DOPA-induced dyskinesia and hyperkinetic disorders providing a mechanistic framework for the study of the interaction between DA and adenosine in the striatonigral system (Exp Neurol. 2014, 261, 733-43. doi: 10.1016/j.expneurol.2014.08.022).
the product has to be stored in the refrigerator (-20°C) otherwise (room temperature) decompose
