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Description: A3 selective agonist
Alternative Names: CF 101,Piclidenoson
Chemical Name: 1-Deoxy-1-[6-[[(3-iodophenyl)methyl]amino]-9H-purin-9-yl]-N-methyl-β-D-ribofuranuronamide
Purity: ≥97% (HPLC)
Biological Activity for IB-MECA
IB-MECA is a 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.
Licensing Information
Sold with the permission of the NIH, US Patent 08/091,109
Technical Data for IB-MECA
| M. Wt | 510.29 |
| Formula | C18H19IN6O4 |
| Storage | Desiccate at +4°C |
| Purity | ≥97% (HPLC) |
| CAS Number | 152918-18-8 |
| PubChem ID | 123683 |
| InChI Key | HUJXGQILHAUCCV-MOROJQBDSA-N |
| Smiles | IC1=CC=CC(CNC2=NC=NC3=C2N=CN3[C@@H]4O[C@H]([C@@](NC)=O)[C@@H](O)[C@H]4O)=C1 |
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 IB-MECA
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 25 |
Preparing Stock Solutions for IB-MECA
The following data is based on the product molecular weight 510.29. 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 |
|---|---|---|---|
| 0.25 mM | 7.84 mL | 39.19 mL | 78.39 mL |
| 1.25 mM | 1.57 mL | 7.84 mL | 15.68 mL |
| 2.5 mM | 0.78 mL | 3.92 mL | 7.84 mL |
| 12.5 mM | 0.16 mL | 0.78 mL | 1.57 mL |
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Product Datasheets for IB-MECA
References for IB-MECA
References are publications that support the biological activity of the product.
Gallo-Rodriguez et al (1994) Structure-activity relationships of N6-benzyladenosine-5'-uronamides as A3-selective adenosine agonists. J.Med.Chem. 37 636 PMID: 8126704
Klotz (2000) Adenosine receptors and their ligands. Naunyn Schmiedebergs Arch.Pharmacol. 362 382 PMID: 11111832
Park et al (2006) N6-(3-iodobenzyl)-adenosine-5'-N-methylcarboxamide confers cardioprotection at reperfusion by inhibiting mitochondrial permeability transition pore opening via glycogen synthase kinase 3β. J.Pharmacol.Exp.Ther. 318 124 PMID: 16611852
If you know of a relevant reference for IB-MECA, please let us know.
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Keywords: IB-MECA, IB-MECA supplier, A3, selective, agonists, Receptors, adenosines, CF, 101, Piclidenoson, Adenosine, 1066, Tocris Bioscience
12 Citations for IB-MECA
Citations are publications that use Tocris products. Selected citations for IB-MECA include:
Eusemann et al (2015) Adenosine Receptors Differentially Regulate the Expression of Regulators of G-Protein Signalling (RGS) 2, 3 and 4 in Astrocyte-Like Cells. PLoS One 10 e0134934 PMID: 26263491
Janes et al (2014) A3 adenosine receptor agonist prevents the development of PacT.-induced neuropathic pain by modulating spinal glial-restricted redox-dependent signaling pathways. Pain 155 2560 PMID: 25242567
He et al (2013) Adenosine regulates bone metabolism via A1, A2A, and A2B receptors in bone marrow cells from normal humans and patients with multiple myeloma. FASEB J 27 3446 PMID: 23682121
Kozma et al (2013) Characterization by flow cytometry of fluorescent, selective agonist probes of the A(3) adenosine receptor. Biochem Pharmacol 85 1171 PMID: 23376019
Ford et al (2015) Engagement of the GABA to KCC2 signaling pathway contributes to the analgesic effects of A3AR agonists in neuropathic pain. J.Neurosci. 35 6057 PMID: 25878279
Park et al (2012) Proximal tubule sphingosine kinase-1 has a critical role in A1 adenosine receptor-mediated renal protection from ischemia. Kidney Int 82 878 PMID: 22695326
Ledderose et al (2016) Adenosine arrests breast cancer cell motility by A3 receptor stimulation. Purinergic Signalling PMID: 27577957
Keene et al (2010) Multivalent dendrimeric and monomeric adenosine agonists attenuate cell death in HL-1 mouse cardiomyocytes expressing the A(3) receptor. Biochem Pharmacol 80 188 PMID: 20346920
Stoddart et al (2012) Fragment screening at adenosine-A(3) receptors in living cells using a fluorescence-based binding assay. Chem Biol 19 1105 PMID: 22999879
Nieri et al (2001) Adenosine-mediated hypotension in in vivo guinea-pig: receptors involved and role of NO. Br J Pharmacol 134 745 PMID: 11606314
Feoktistov et al (2003) Mast cell-mediated stimulation of angiogenesis: cooperative interaction between A2B and A3 adenosine receptors. J Neurosci 92 485 PMID: 12600879
Kornerup et al (2005) Pharmacological characterisation of the adenosine receptor mediating increased ion transport in the mouse isolated trachea and the effect of allergen challenge. Br J Pharmacol 144 1011 PMID: 15685200
Do you know of a great paper that uses IB-MECA from Tocris? Please let us know.
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