2-Cl-IB-MECA

Name: 2-Cl-IB-MECA
Brand: Tocris Bioscience
SKU: 1104
Rating: 4 (0 reviews)

Tocris Bioscience a Bio-Techne Brand

Catalog # 1104

Citations (13)

(1)

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Key Product Details

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)
Molecular Weight:	544.74

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Biological Activity for 2-Cl-IB-MECA

2-Cl-IB-MECA is a high affinity and extremely selective A₃ adenosine receptor agonist (K_i = 0.33 nM). Displays 2500- and 1400-fold selectivity over A₁ and A_2A 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 for 2-Cl-IB-MECA

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
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.

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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References for 2-Cl-IB-MECA

References are publications that support the biological activity of the product.

Jacobson Adenosine A₃ receptors: novel ligands and paradoxical effects. TiPS 1998 PMID: 9652191
Schaick Hemodynamic effects of histamine release elicited by the selective adenosine A₃ receptor agonist 2-Cl-IB-MECA in conscious rats. Eur.J.Pharmacol. 1996 PMID: 8858305
Kim 2-Substitution of N⁶-benzyladenosine-5'-uronamides enhances selectivity for A₃ adenosine receptors. J.Med.Chem. 1994 PMID: 7932588

Citations for 2-Cl-IB-MECA (13)

Showing 1 - 10 of 13 citations Showing All

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

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
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
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
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
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
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

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