Catalog Number: 2158
Chemical Name: (1R*,2S*)-4-[2-Chloro-6-(methylamino)-9H-purin-9-yl]-2-(phosphonooxy)bicyclo[3.1.0]hexane-1-methanol dihydrogen phosphate ester diammonium salt
Biological Activity
Selective, high affinity competitive antagonist of the P2Y1 receptor (Ki = 2.5 nM; IC50 = 51.6 nM). Fails to block nucleotide signaling at most other P2Y receptors (P2Y2, P2Y4, P2Y6, P2Y11 and P2Y12) and potently inhibits ADP-induced aggregation of human blood platelets in vitro (pKB = 8.05).
Technical Data
  • M.Wt:
    503.78
  • Formula:
    C13H18ClN5O8P2.2NH3
  • Solubility:
    Soluble to 100 mM in water
  • Purity:
    >98%
  • Storage:
    Desiccate at -20°C
  • CAS No:
    367909-40-8
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis. All Tocris products are intended for laboratory research use only.
Additional Information
Licensing Caveats:
Sold under license from the NIH, US Patent 10/169975
Background References
  1. 2-Substitution of adenine nucleotide analogues containing a bicyclo[3.1.0]hexane ring system locked in a northern conformation: enhanced potency as P2Y1 receptor antagonists.
    Kim et al.
    J.Med.Chem, 2003;46:4974
  2. Synthesis, biological activity, and molecular modeling of ribose-modified deoxyadenosine bisphosphate analogues as P2Y1 receptor ligands.
    Nandanan et al.
    J.Med.Chem., 2000;43:829
  3. 2-Chloro N6-methyl-(N)-methanocarba-2'-deoxyadenosine-3',5'-bisphosphate is a selective high affinity P2Y1 receptor antagonist.
    Boyer et al.
    Br.J.Pharmacol., 2002;135:2004
Citations:

The citations listed below are publications that use Tocris products. Selected citations for MRS 2279 include:

3 Citations: Showing 1 - 3
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  1. Increase of intracellular Ca2+ by purinergic receptors in cultured rat lacrimal gland myoepithelial cells.
    Authors: Ohtomo Et al.
    Invest Ophthalmol Vis Sci 2011;52:9503
  2. Astrocytic P2Y(1) receptor is involved in the regulation of cytokine/chemokine transcription and cerebral damage in a rat model of cerebral ischemia.
    Authors: Kuboyama Et al.
    Cell Death Dis 2011;31:1930
  3. Protein kinase Ctheta negatively regulates store-independent Ca2+ entry and phosphatidylserine exposure downstream of glycoprotein VI in platelets.
    Authors: Harper and Poole
    J Biol Chem 2010;285:19865

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