IB-MECA

Cat. No. 1066

IB-MECA C18H19IN6O4 [152918-18-8]

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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.

Licensing Information

Sold with the permission of the NIH, US Patent 08/091,109

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.

Certificate of Analysis / Product Datasheet / Safety Data Sheet

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.

Klotz (2000) Adenosine receptors and their ligands. Naunyn Schmiedebergs Arch.Pharmacol. 362 382. PMID: 11111832.

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.

If you know of a relevant reference for this product please let us know.

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

Ledderose et al (2016) Adenosine arrests breast cancer cell motility by A3 receptor stimulation. Purinergic Signalling. PMID: 27577957.

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.

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.

Janes et al (2014) A3 adenosine receptor agonist prevents the development of paclitaxel-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.

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.

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.

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.

Feoktistov et al (2003) Mast cell-mediated stimulation of angiogenesis: cooperative interaction between A2B and A3 adenosine receptors. J Neurosci 92 485. PMID: 12600879.

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.

Do you know of a great paper that uses IB-MECA from Tocris? If so please let us know.show all ▼show less ▲

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