2-Cl-IB-MECA

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Cat.No. 1104 - 2-Cl-IB-MECA | C18H18ClIN6O4 | CAS No. 163042-96-4
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)
Datasheet
Citations (12)
Literature

Biological Activity

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

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.

All Tocris products are intended for laboratory research use only.

Solubility Data

SolubilitySoluble to 100 mM in DMSO

Preparing Stock Solutions

The following data is based on the product molecular weight 544.74. 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.

Select a batch to recalculate based on the batch molecular weight:
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

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

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


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Keywords: 2-Cl-IB-MECA, supplier, selective, A3, agonists, Receptors, adenosines, 2ClIBMECA, Adenosine, A3, Receptors, Tocris Bioscience

12 Citations for 2-Cl-IB-MECA

Citations are publications that use Tocris products. Selected citations for 2-Cl-IB-MECA include:

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

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

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

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

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

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

Corriden et al (2013) Adenosine-A3 receptors in neutrophil microdomains promote the formation of bacteria-tethering cytonemes. Biochim Biophys Acta 14 726 PMID: 23817552

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


Do you know of a great paper that uses 2-Cl-IB-MECA from Tocris? If so please let us know.

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