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MRS 5698

Cat. No. 5428 Submit a Review Datasheet / COA / SDS
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Cat.No. 5428 - MRS 5698 | C28H23ClF2N6O3 | CAS No. 1377273-00-1
Description: High affinity and selective A3 adenosine receptor agonist
Chemical Name: (1S,2R,3S,4R,5S)-4-[6-[[(3-Chlorophenyl)methyl]amino]-2-[2-(3,4-difluorophenyl)ethynyl]-9H-purin-9-yl]-2,3-dihydroxy-N-methylbicyclo[3.1.0]hexane-1-carboxamide
Purity: ≥96% (HPLC)
Datasheet
Citations
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Literature
Biological Activity Technical Data Solubility Calculators Datasheets References

Biological Activity

High affinity and selective A3 adenosine receptor agonist (Ki ~ 3 nM); displays >1000-fold selectivity over A1 and A2A adenosine receptors. Reverses mechanoallodynia in several neuropathic pain models in vivo. Orally bioavailable.

Technical Data

M. Wt 564.97
Formula C28H23ClF2N6O3
Storage Store at -20°C
Purity ≥96% (HPLC)
CAS Number 1377273-00-1
PubChem ID 57523213
InChI Key LYLLLJJYBWLGHW-CIZVZKTGSA-N
Smiles O=[C@](NC)[C@@]1(C2)[C@H]2[C@@H](N3C(N=C(C#CC6=CC(F)=C(F)C=C6)N=C4NCC5=CC(Cl)=CC=C5)=C4N=C3)[C@H](O)[C@@H]1O

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 5.65 10

Preparing Stock Solutions

The following data is based on the product molecular weight 564.97. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
0.1 mM 17.7 mL 88.5 mL 177 mL
0.5 mM 3.54 mL 17.7 mL 35.4 mL
1 mM 1.77 mL 8.85 mL 17.7 mL
5 mM 0.35 mL 1.77 mL 3.54 mL

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References

References are publications that support the biological activity of the product.

Little et al (2015) Endogenous adenosine A3 receptor activation selectively alleviates persistent pain states. Brain 138 28 PMID: 25414036

Tosh et al (2012) Structure-guided design of A3 adenosine receptor-selective nucleosides: combination of 2-arylethynyl and bicyclo[3.1.0]hexane substitutions. J.Med.Chem. 55 4847 PMID: 22559880

Tosh et al (2015) Efficient, large-scale synthesis and preclinical studies of MRS5698, a highly selective A3 adenosine receptor agonist that protects against chronic neuropathic pain. Purinergic Signal. 11 371 PMID: 26111639

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