IB-MECAA potent and selective Adenosine A3-R agonist

IB-MECA (CAS 152918-18-8)

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Synonym: N6-(3-Iodobenzyl)adenosine-5′-N-methyluronamide
Application: A potent and selective Adenosine A3-R agonist
CAS Number: 152918-18-8
Purity: ≥97%
Molecular Weight: 510.29
Molecular Formula: C18H19IN6O4
* Refer to Certificate of Analysis for lot specific data (including water content).
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IB-MECA has been shown to act as a potent and selective Adenosine A3-R agonist with Ki values of 1.1, 54 and 56 nM for Adenosine A3-R, Adenosine A1-R and Adenosine A2A-R, respectively. This compound has demonstrated cardioprotective activity.


References

1. Gallo-Rodriguez, C., et al. 1996. J. Org. Chem. 61: 1886-1889. PMID: 11667072
2. Klotz, K.N. 2000. Naunyn-Schmied. Arch. Pharmacol. 362: 382-391. PMID: 11111832
3. Park, S.S., et al. 2006. J. Pharmacol. Exp. Ther. 318: 124-131. PMID: 16611852

Physical State :
Solid
Solubility :
Soluble in DMSO (50 mM), and hot ethanol (>10 mg/ml). Insoluble in water, aqueous acid, and aqueous base.
Storage :
Store at 4° C
Density :
1.98 g/cm3 (Predicted)
Refractive Index :
n20D 1.81 (Predicted)
IC50 :
Inhibition of isoproterenol-stimulated cAMP accumulation: EC5050 = 1 nM (HEK 293 cells expressing human Adenosine A3 receptor); Adenosine A3-R: IC50 = 1.2 nM (human); Effect on forskolin-stimulated cyclic AMP production: EC5050 = 3.6 nM (intact CHO cell expressing the human Adenosine A3 receptor); Activation of adenosine A2B receptor: EC5050 ≥10 µM (mouse); Effective concentration for cAMP production: EC5050 = 11 µM (CHO-KI cells stably transfected with human adenosine A2B receptor cDNA)
Ki Data :
Adenosine A3-R: Ki= 1.1 nM; Adenosine A1-R: Ki= 12.6 nM; Adenosine A2A-R: Ki= 56 nM
pK Values :
pKa: 12.72 (Predicted), pKb: 3.02 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
VJ2247100
PubChem CID :
123683
MDL Number :
MFCD00671785
SMILES :
CNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C2N=CN=C3NCC4=CC(=CC=C4)I)O)O

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Certificate of Analysis

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