IB-MECA

Pricing Availability Delivery Time Qty
Cat.No. 1066 - IB-MECA | C18H19IN6O4 | CAS No. 152918-18-8
Description: A3 selective agonist
Chemical Name: 1-Deoxy-1-[6-[[(3-iodophenyl)methyl]amino]-9H-purin-9-yl]-N-methyl-β-D-ribofuranuronamide
Purity: ≥97% (HPLC)
Datasheet
Citations (11)
Literature

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
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.

All Tocris products are intended for laboratory research use only.

Solubility Data

SolubilitySoluble to 25 mM in DMSO

Preparing Stock Solutions

The following data is based on the product molecular weight 510.29. 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.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.96 mL 9.8 mL 19.6 mL
5 mM 0.39 mL 1.96 mL 3.92 mL
10 mM 0.2 mL 0.98 mL 1.96 mL
50 mM 0.04 mL 0.2 mL 0.39 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.

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


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

11 Citations for IB-MECA

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

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

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


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