(±)-5'-Chloro-5'-deoxy-ENBA

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Cat.No. 3576 - (±)-5'-Chloro-5'-deoxy-ENBA | C17H22ClN5O3 | CAS No. 103626-26-2
Description: Highly selective A1 agonist
Chemical Name: N-Bicyclo[2.2.1]hept-2-yl-5'-chloro-5'-deoxyadenosine
Purity: ≥98% (HPLC)
Datasheet
Citations
Reviews (1)
Literature (4)

Biological Activity

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 formaline-induced nocifensive behavior in mice; antinociceptive.

Compound Libraries

(±)-5'-Chloro-5'-deoxy-ENBA is also offered as part of the Tocriscreen Plus. Find out more about compound libraries available from Tocris.

Technical Data

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

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 37.98 100
ethanol 37.98 100

Preparing Stock Solutions

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

Certificate of Analysis / Product Datasheet
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References

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


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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

Citations for (±)-5'-Chloro-5'-deoxy-ENBA

Citations are publications that use Tocris products.

Currently there are no citations for (±)-5'-Chloro-5'-deoxy-ENBA. 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

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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

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