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I146

Sigma-Aldrich

IB-MECA

solid, ≥98% (HPLC)

Sinonimo/i:

1-Deoxy-1-[6-[((3-Iodophenyl)methyl)amino]-9H-purin-9-yl]-N-methyl-β-D-ribofuranuronamide, N6-(3-Iodobenzyl)adenosine-5′-N-methyluronamide

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About This Item

Formula empirica (notazione di Hill):
C18H19IN6O4
Numero CAS:
152918-18-8
Peso molecolare:
510.29
Numero MDL:
MFCD00671785
Codice UNSPSC:
12352200
ID PubChem:
24277717
NACRES:
NA.32

Livello qualitativo

100

Saggio

≥98% (HPLC)

Stato

solid

Colore

white

Solubilità

ethanol: >10 mg/mL (hot)
DMSO: >5 mg/mL
H2O: insoluble
aqueous acid: insoluble
aqueous base: insoluble

Temperatura di conservazione

2-8°C

Stringa SMILE

CNC(=O)[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(NCc4cccc(I)c4)ncnc23

InChI

1S/C18H19IN6O4/c1-20-17(28)14-12(26)13(27)18(29-14)25-8-24-11-15(22-7-23-16(11)25)21-6-9-3-2-4-10(19)5-9/h2-5,7-8,12-14,18,26-27H,6H2,1H3,(H,20,28)(H,21,22,23)/t12-,13+,14-,18+/m0/s1
HUJXGQILHAUCCV-MOROJQBDSA-N

Informazioni sul gene

human ... ADORA1(134) , ADORA2A(135) , ADORA2B(136) , ADORA3(140)
rat ... Adora1(29290) , Adora2a(25369) , Adora3(25370)

Applicazioni

IB-MECA has been used for intraocular pressure and corneal thickness measurements in rabbits.

Azioni biochim/fisiol

Selective A3 adenosine receptor agonist.

Note legali

Sold under license from the National Institutes of Health.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
042M4610V
117K4605
057K4631
051K4607

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John A Auchampach et al.
American journal of physiology. Heart and circulatory physiology, 285(2), H607-H613 (2003-04-12)
We examined the effect of the A3 adenosine receptor (AR) agonist IB-MECA on infarct size in an open-chest anesthetized dog model of myocardial ischemia-reperfusion injury. Dogs were subjected to 60 min of left anterior descending (LAD) coronary artery occlusion and
Athena M Keene et al.
Biochemical pharmacology, 80(2), 188-196 (2010-03-30)
Multivalent dendrimeric conjugates of GPCR ligands may have increased potency or selectivity in comparison to monomeric ligands, a phenomenon that was tested in a model of cytoprotection in mouse HL-1 cardiomyocytes. Quantitative RT-PCR indicated high expression levels of endogenous A(1)
P Mlejnek et al.
Acta physiologica (Oxford, England), 199(2), 171-179 (2010-02-04)
The sensitivity of cancer cells which exhibit multi-drug resistance phenotype to A3 adenosine receptor (A3AR) agonist N(6)-(3-iodobenzyl)-adenosine-5'-N-methylcarboxamide (IB-MECA) was studied. To establish direct relationship between P-glycoprotein (P-gp, ABCB1 and MDR1) expression and IB-MECA induced cell death, a straightforward method for
Michal Hofer et al.
International journal of radiation biology, 86(8), 649-656 (2010-07-01)
Research areas of 'post-exposure treatment' and 'cytokines and growth factors' have top priority among studies aimed at radiological nuclear threat countermeasures. The experiments were aimed at testing the ability of N(6)-(3-iodobenzyl)adenosine-5'-N-methyluronamide (IB-MECA), an adenosine A(3) receptor agonist, to modulate hematopoiesis
Jorge Guzman et al.
Inflammatory bowel diseases, 12(8), 766-789 (2006-08-19)
Adenosine A3 receptors (ADOA3Rs) are emerging as novel purinergic targets for treatment of inflammatory diseases. Our goal was to assess the protective effect of the ADOA3R agonist N(6)-(3-iodobenzyl)-adenosine-5-N-methyluronamide (IB-MECA) on gene dysregulation and injury in a rat chronic model of
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