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I146

IB-MECA

Name: IB-MECA
Brand: SIGMA

solid, ≥98% (HPLC)

Synonym(e):

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

Empirische Formel (Hill-System):

C₁₈H₁₉IN₆O₄

CAS-Nummer:

152918-18-8

Molekulargewicht:

510.29

MDL-Nummer:

MFCD00671785

UNSPSC-Code:

12352200

PubChem Substanz-ID:

24277717

NACRES:

NA.32

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Sigma-Aldrich

K0250

Kainic acid monohydrate

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

solid

Farbe

white

Löslichkeit

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

Lagertemp.

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

InChIKey

HUJXGQILHAUCCV-MOROJQBDSA-N

Angaben zum Gen

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

Anwendung

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

Biochem./physiol. Wirkung

Selective A₃ adenosine receptor agonist.

Rechtliche Hinweise

Sold under license from the National Institutes of Health.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

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Enhancing pigmentation via activation of A3 adenosine receptors in B16 melanoma cells and in human skin explants.

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

Cardioprotection induced by adenosine A1 receptor agonists in a cardiac cell ischemia model involves cooperative activation of adenosine A2A and A2B receptors by endogenous adenosine.

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

Activation of adenosine A(3) receptors supports hematopoiesis-stimulating effects of granulocyte colony-stimulating factor in sublethally irradiated mice.

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

ADOA3R as a therapeutic target in experimental colitis: proof by validated high-density oligonucleotide microarray analysis.

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

Adenosine A(3) receptor suppresses prostate cancer metastasis by inhibiting NADPH oxidase activity.

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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