Catalog Number: 1066
Chemical Name: 1-Deoxy-1-[6-[[(3-iodophenyl)methyl]amino]-9H-purin-9-yl]-N-methyl-β-D-ribofuranuronamide
Biological Activity
Potent and selective A3 adenosine receptor agonist (Ki values are 1.1, 54 and 56 nM for A3, A1 and A2A receptors respectively). Cardioprotective, reduces infarct size upon reperfusion in rats.
Technical Data
  • M.Wt:
    510.29
  • Formula:
    C18H19IN6O4
  • Solubility:
    Soluble to 25 mM in DMSO
  • Purity:
    >97%
  • Storage:
    Desiccate at +4°C
  • CAS No:
    152918-18-8
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 with the permission of the NIH, US Patent 08/091,109
Background References
  1. Structure-activity relationships of N6-benzyladenosine-5'-uronamides as A3-selective adenosine agonists.
    Gallo-Rodriguez et al.
    J.Med.Chem., 1994;37:636
  2. Adenosine receptors and their ligands.
    Klot
    Naunyn Schmiedebergs Arch.Pharmacol., 2000;362:382
  3. N6-(3-iodobenzyl)-adenosine-5'-N-methylcarboxamide confers cardioprotection at reperfusion by inhibiting mitochondrial permeability transition pore opening via glycogen synthase kinase 3β.
    Park et al.
    J.Pharmacol.Exp.Ther., 2006;318:124
Citations:

The citations listed below are publications that use Tocris products. Selected citations for IB-MECA include:

11 Citations: Showing 1 - 10
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  1. Adenosine arrests breast cancer cell motility by A3 receptor stimulation.
    Authors: Ledderose Et al.
    Purinergic Signalling 2016;
  2. Engagement of the GABA to KCC2 signaling pathway contributes to the analgesic effects of A3AR agonists in neuropathic pain.
    Authors: Ford Et al.
    J.Neurosci. 2015;35:6057
  3. Adenosine Receptors Differentially Regulate the Expression of Regulators of G-Protein Signalling (RGS) 2, 3 and 4 in Astrocyte-Like Cells.
    Authors: Eusemann Et al.
    PLoS One 2015;10:e0134934
  4. A3 adenosine receptor agonist prevents the development of paclitaxel-induced neuropathic pain by modulating spinal glial-restricted redox-dependent signaling pathways.
    Authors: Janes Et al.
    Pain 2014;155:2560
  5. Characterization by flow cytometry of fluorescent, selective agonist probes of the A(3) adenosine receptor.
    Authors: Kozma Et al.
    Biochem Pharmacol 2013;85:1171
  6. Adenosine regulates bone metabolism via A1, A2A, and A2B receptors in bone marrow cells from normal humans and patients with multiple myeloma.
    Authors: He Et al.
    FASEB J 2013;27:3446
  7. Fragment screening at adenosine-A(3) receptors in living cells using a fluorescence-based binding assay.
    Authors: Stoddart Et al.
    Chem Biol 2012;19:1105
  8. Multivalent dendrimeric and monomeric adenosine agonists attenuate cell death in HL-1 mouse cardiomyocytes expressing the A(3) receptor.
    Authors: Keene Et al.
    Biochem Pharmacol 2010;80:188
  9. Pharmacological characterisation of the adenosine receptor mediating increased ion transport in the mouse isolated trachea and the effect of allergen challenge.
    Authors: Kornerup Et al.
    Br J Pharmacol 2005;144:1011
  10. Mast cell-mediated stimulation of angiogenesis: cooperative interaction between A2B and A3 adenosine receptors.
    Authors: Feoktistov Et al.
    J Neurosci 2003;92:485
  11. Adenosine-mediated hypotension in in vivo guinea-pig: receptors involved and role of NO.
    Authors: Nieri Et al.
    Br J Pharmacol 2001;134:745
Expand to show all 11 Citations

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