IB-MECA

Names

[ Name ]:
IB-MECA

[Synonym ]:
UNII-30679UMI0N
Piclidenoson
(2S,3S,4R,5R)-3,4-Dihydroxy-5-{6-[(3-iodobenzyl)amino]-9H-purin-9-yl}-N-methyltetrahydro-2-furancarboxamide
IBMECA
(2S,3S,4R,5R)-3,4-Dihydroxy-5-{6-[(3-iodobenzyl)amino]-9H-purin-9-yl}-N-methyltetrahydrofuran-2-carboxamide (non-preferred name)
CF 101
3-IB-Meca
IB-MECA
CF101

Biological Activity

[Description]:

Piclidenoson (IB-MECA) is an agonist of the adenosine A3 receptor with EC50 values of 0.11 μM. IC50 value: 0.11 μM (EC50) [3]Target: adenosine A3 receptorin vitro: Piclidenoson has been shown to play important roles in cell proliferation and apoptosis in a variety of cancer cell lines. ThePiclidenoson was capable of decreasing intracellular cyclic adenosine monophosphate (cAMP) that was the reason for the presence of functional A3 adenosine receptor on the cell lines. Piclidenoson significantly reduced cell viability in a dose-dependent manner. Piclidenoson, an A3AR agonist, inhibits the growth of different cancer cell types like melanoma, colon, breast, leukemia, and prostatePiclidenoson was able to inhibit forskolin-stimulated cAMP levels with an EC50 value of 0.82 μM in OVCAR-3 cells. Piclidenoson was able to inhibit forskolin-stimulated cAMP levels with an EC50 value of 1.2 μM in Caov-4 cells.in vivo: Administrations of single intraperitoneal doses of either Piclidenoson 0.5 h post-irradiation resulted in statistically significant increases of MST in comparison with the control irradiated mice.[2]

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Adenosine Receptor

Research Areas >> Cancer

[References]

[1]. Hofer M, et al. Agonist of the adenosine A3 receptor, IB-MECA, and inhibitor of cyclooxygenase-2, meloxicam, given alone or in a combination early after total body irradiation enhance survival of γ-irradiated mice. Radiat Environ Biophys. 2014 Mar;53(1):211-215.

[2]. Abedi H, et al. Mitochondrial and caspase pathways are involved in the induction of apoptosis by IB-MECA in ovarian cancer cell lines. Tumour Biol. 2014 Nov;35(11):11027-11039.

[3]. Shin Y, et al. Activation of Phosphoinositide Breakdown and Elevation of Intracellular Calcium in a Rat RBL-2H3 Mast Cell Line by Adenosine Analogs: Involvement of A(3)-Adenosine Receptors? Drug Dev Res. 1996 Sep 1;39(1):36-46.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
2.0±0.1 g/cm3

[ Molecular Formula ]:
C₁₈H₁₉IN₆O₄

[ Molecular Weight ]:
510.286

[ Exact Mass ]:
510.051239

[ PSA ]:
134.42000

[ LogP ]:
2.08

[ Index of Refraction ]:
1.808

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2934999090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Equilibrium and kinetic selectivity profiling on the human adenosine receptors.

Biochem. Pharmacol. 105 , 34-41, (2016)

Classical evaluation of target selectivity is usually undertaken by measuring the binding affinity of lead compounds against a number of potential targets under equilibrium conditions, without conside...

Activation of A1, A2A, or A3 adenosine receptors attenuates lung ischemia-reperfusion injury.

J. Thorac. Cardiovasc. Surg. 140(2) , 440-6, (2010)

Adenosine and the activation of specific adenosine receptors are implicated in the attenuation of inflammation and organ ischemia-reperfusion injury. We hypothesized that activation of A(1), A(2A), or...

Activation of adenosine low-affinity A3 receptors inhibits the enteric short interplexus neural circuit triggered by histamine.

Am. J. Physiol. Gastrointest. Liver Physiol. 297(6) , G1147-62, (2009)

We tested the novel hypothesis that endogenous adenosine (eADO) activates low-affinity A3 receptors in a model of neurogenic diarrhea in the guinea pig colon. Dimaprit activation of H2 receptors was u...