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I146

Sigma-Aldrich

IB-MECA

solid, ≥98% (HPLC)

Sinónimos:

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

Fórmula empírica (notación de Hill):
C18H19IN6O4
Número de CAS:
152918-18-8
Peso molecular:
510.29
MDL number:
MFCD00671785
UNSPSC Code:
12352200
PubChem Substance ID:
24277717
NACRES:
NA.32

Quality Level

100

assay

≥98% (HPLC)

form

solid

color

white

solubility

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

storage temp.

2-8°C

SMILES string

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

InChI key

HUJXGQILHAUCCV-MOROJQBDSA-N

Gene Information

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

Application

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

Biochem/physiol Actions

Selective A3 adenosine receptor agonist.

Legal Information

Sold under license from the National Institutes of Health.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Lea Madi et al.
Experimental dermatology, 22(1), 74-77 (2012-10-24)
A3 adenosine receptor, A3AR, belongs to the Gi proteins coupled receptors. Activation of A3AR by its agonist, IB-MECA, decreases cAMP and was expected to reduce melanin level. Unexpectedly, B16 melanoma cells exposed to IB-MECA increased melanin levels in a dose-dependent
Vijay B Urmaliya et al.
Journal of cardiovascular pharmacology, 53(5), 424-433 (2009-04-01)
Extracellular adenosine concentrations increase within the heart during ischemia, and any exogenous adenosine receptor agonists therefore work in the context of significant local agonist concentrations. We evaluated the interactions between A1, A2A, A2B, and A3 receptors in the presence and
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
Sarvesh Jajoo et al.
Neoplasia (New York, N.Y.), 11(11), 1132-1145 (2009-11-03)
Prostate cancer is the most commonly diagnosed and second most lethal malignancy in men, due mainly to a lack of effective treatment for the metastatic disease. A number of recent studies have shown that activation of the purine nucleoside receptor
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