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Submit Review2-Cl-IB-MECA
Description: Highly selective A3 agonist
Chemical Name: 1-[2-Chloro-6-[[(3-iodophenyl)methyl]amino]-9H-purin-9-yl]-1-deoxy-N-methyl-β-D-ribofuranuronamide
Purity: ≥98% (HPLC)
Biological Activity for 2-Cl-IB-MECA
2-Cl-IB-MECA is a high affinity and extremely selective A3 adenosine receptor agonist (Ki = 0.33 nM). Displays 2500- and 1400-fold selectivity over A1 and A2A receptors respectively. Exhibits high selectivity over the Na+-independent adenosine transporter.
Licensing Information
Sold with the permission of the NIH, US Patent 08/091,109
Technical Data for 2-Cl-IB-MECA
| M. Wt | 544.74 |
| Formula | C18H18ClIN6O4 |
| Storage | Desiccate at +4°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 163042-96-4 |
| PubChem ID | 3035850 |
| InChI Key | IPSYPUKKXMNCNQ-PFHKOEEOSA-N |
| Smiles | O[C@@H]1[C@@H]([C@](NC)=O)O[C@@H](N(C=N4)C2=C4C(NCC3=CC(I)=CC=C3)=NC(Cl)=N2)[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 for 2-Cl-IB-MECA
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 100 |
Preparing Stock Solutions for 2-Cl-IB-MECA
The following data is based on the product molecular weight 544.74. 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 | 1.84 mL | 9.18 mL | 18.36 mL |
| 5 mM | 0.37 mL | 1.84 mL | 3.67 mL |
| 10 mM | 0.18 mL | 0.92 mL | 1.84 mL |
| 50 mM | 0.04 mL | 0.18 mL | 0.37 mL |
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Product Datasheets for 2-Cl-IB-MECA
References for 2-Cl-IB-MECA
References are publications that support the biological activity of the product.
Jacobson (1998) Adenosine A3 receptors: novel ligands and paradoxical effects. TiPS 19 184 PMID: 9652191
Kim et al (1994) 2-Substitution of N6-benzyladenosine-5'-uronamides enhances selectivity for A3 adenosine receptors. J.Med.Chem. 37 3614 PMID: 7932588
Schaick et al (1996) Hemodynamic effects of histamine release elicited by the selective adenosine A3 receptor agonist 2-Cl-IB-MECA in conscious rats. Eur.J.Pharmacol. 308 311 PMID: 8858305
If you know of a relevant reference for 2-Cl-IB-MECA, please let us know.
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Keywords: 2-Cl-IB-MECA, 2-Cl-IB-MECA supplier, selective, A3, agonists, Receptors, adenosines, 2ClIBMECA, Adenosine, 1104, Tocris Bioscience
13 Citations for 2-Cl-IB-MECA
Citations are publications that use Tocris products. Selected citations for 2-Cl-IB-MECA include:
Corriden et al (2013) Adenosine-A3 receptors in neutrophil microdomains promote the formation of bacteria-tethering cytonemes. Biochim Biophys Acta 14 726 PMID: 23817552
Bhanu et al (2008) Inhibition of erythroblast growth and fetal hemoglobin production by ribofuranose-substituted adenosine derivatives. J Pharmacol Exp Ther 1782 504 PMID: 18586086
Iannone et al (2014) Adenosine limits the therapeutic effectiveness of anti-CTLA4 mAb in a mouse melanoma model. EMBO Rep 4 172 PMID: 24660106
Vincenzi et al (2013) Pulsed electromagnetic fields increased the anti-inflammatory effect of A2A and A3 adenosine receptors in human T/C-28a2 chondrocytes and hFOB 1.19 osteoblasts. PLoS One 8 e65561 PMID: 23741498
Jinka et al (2011) Season primes the brain in an arctic hibernator to facilitate entrance into torpor mediated by adenosine A(1) receptors. J Neurosci 31 10752 PMID: 21795527
Angelantonio et al (2015) Basal adenosine modulates the functional properties of AMPA receptors in mouse hippocampal neurons through the activation of A1R A2AR and A3R. Sci Rep 9 409 PMID: 26528137
Ren et al (2015) An adenosine A3 receptor agonist inhibits DSS-induced colitis in mice through modulation of the NF-κB signaling pathway. J Neurosci 5 9047 PMID: 25762375
Kan et al (2012) Imiquimod suppresses propagation of herpes simplex virus 1 by upregulation of cystatin A via the adenosine receptor A1 pathway. J Virol 86 10338 PMID: 22787201
Montinaro et al (2012) Adoptive immunotherapy with Cl-IB-MECA-treated CD8+ T cells reduces melanoma growth in mice. PLoS One 7 e45401 PMID: 23028986
Rosito et al (2012) CXCL16 orchestrates adenosine A3 receptor and MCP-1/CCL2 activity to protect neurons from excitotoxic cell death in the CNS. Neoplasia 32 3154 PMID: 22378888
Morello et al (2011) NK1.1 cells and CD8 T cells mediate the antitumor activity of Cl-IB-MECA in a mouse melanoma model. Am J Cancer Res 13 365 PMID: 21472141
Man et al (2003) Alteration of the purinergic modulation of enteric neurotransmission in the mouse ileum during chronic intestinal inflammation. Br J Pharmacol 139 172 PMID: 12746236
Germack and Dickenson (2004) Characterization of ERK1/2 signalling pathways induced by adenosine receptor subtypes in newborn rat cardiomyocytes. Br J Pharmacol 141 329 PMID: 14751870
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