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I146

Sigma-Aldrich

IB-MECA

solid, ≥98% (HPLC)

Synonyme(s) :

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

Formule empirique (notation de Hill):
C18H19IN6O4
Numéro CAS:
152918-18-8
Poids moléculaire :
510.29
Numéro MDL:
MFCD00671785
Code UNSPSC :
12352200
ID de substance PubChem :
24277717
Nomenclature NACRES :
NA.32

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

solid

Couleur

white

Solubilité

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

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

HUJXGQILHAUCCV-MOROJQBDSA-N

Informations sur le gène

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.

Actions biochimiques/physiologiques

Selective A3 adenosine receptor agonist.

Informations légales

Sold under license from the National Institutes of Health.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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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
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
Shane M Devine et al.
Bioorganic & medicinal chemistry, 18(9), 3078-3087 (2010-04-14)
A number of N(6)-substituted adenosine-5'-N-methylcarboxamides were synthesised and their pharmacology, in terms of their receptor affinity, selectivity and cardioprotective effects, were explored. The first series of compounds, 4a-4f and 5a-5f, showed modest receptor affinity for the A(3)AR with K(i) values
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
L Rath-Wolfson et al.
Clinical and experimental rheumatology, 24(4), 400-406 (2006-09-08)
The anti-inflammatory effect of adenosine is partially mediated via the A3 adenosine receptor (A3AR), a Gi protein associated cell surface receptor. The highly selective A3AR agonist, IB-MECA was earlier shown to prevent the clinical and pathological manifestations of arthritis in
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