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AB120438

IB-MECA, A3 agonist

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(2 Publications)

MW 510.3 Da, Purity >97%. Highly potent and selective A3 agonist (Ki values are 1.1, 12.6 and 56 nM at A3, A1 and A2A receptors, respectively). Produces potent cardioprotective effects against myocardial injury. Mediates suppression of melanoma cells and suppresses human breast cancer cell proliferation.
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Chemical Structure - IB-MECA, A3 agonist (AB120438)
  • Chemical Structure

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Chemical Structure - IB-MECA, A3 agonist (AB120438)

2D chemical structure image of ab120438, IB-MECA, A3 agonist

Key facts

CAS number

152918-18-8

Purity

>97%

Form

Solid

form

Molecular weight

510.3 Da

Molecular formula

C<sub>1</sub><sub>8</sub>H<sub>1</sub><sub>9</sub>IN<sub>6</sub>O<sub>4</sub>

PubChem

123683

Nature

Synthetic

Solubility

Soluble in DMSO to 50 mM

Biochemical name

IB-Meca

Biological description

Highly potent and selective A3 agonist (Ki values are 1.1, 12.6 and 56 nM at A3, A1 and A2A receptors, respectively). Produces potent cardioprotective effects against myocardial injury. Mediates suppression of melanoma cells and suppresses human breast cancer cell proliferation.

Canonical smiles

CNC(=O)C1C(C(C(O1)N2C=NC3=C(N=CN=C32)NCC4=CC(=CC=C4)I)O)O

Isomeric smiles

CNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)NCC4=CC(=CC=C4)I)O)O

InChi

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

IUPAC Name

(2S,3S,4R,5R)-3,4-dihydroxy-5-[6-[(3-iodophenyl)methylamino]purin-9-yl]-N-methyloxolane-2-carboxamide

Properties and storage information

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
+4°C
Appropriate long-term storage conditions
+4°C
Storage information
Store under desiccating conditions|The product can be stored for up to 12 months

Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

Adenosine receptors including the Adenosine A1 Receptor Adenosine A2a Receptor Adenosine A2b Receptor (ADORA2B) and Adenosine A3 Receptor (A3AR) function as G protein-coupled receptors (GPCRs) that modulate a range of cellular responses. These receptors are integral to cell membranes and are expressed in various tissues including the brain heart and vasculature. For instance the Adenosine A1 Receptor regulates heart rate and has a molecular mass of approximately 37 kDa. RXFP1 and 5-HT2B Receptor also part of the GPCR family contribute to different signaling mechanisms. Meanwhile ENT1 (Equilibrative Nucleoside Transporter 1) and SLC5A7 serve as transporters controlling the movement of adenosine and choline respectively. TDP1 although different in function plays a role in DNA repair.
Biological function summary

Adenosine receptors influence various physiological processes like inflammatory response and neurotransmission. They do not operate in isolation but interact with other components in complex networks. For instance the Adenosine A2a Receptor interacts with dopamine receptors affecting motor function and mood regulation. Conversely 5-HT2C Receptor a serotonin receptor modulates mood and appetite by influencing neurotransmitter release in the central nervous system. RXFP1 plays a part in reproductive system signaling. On another front ENT1 and SLC5A7 enable cellular uptake and distribution of key molecules necessary for maintaining cellular and systemic balance.

Pathways

Adenosine receptors participate in the cyclic AMP (cAMP) signaling pathway which is important for regulating metabolic and gene expression processes. These receptors particularly A2a and A2b often couple with Gs proteins to elevate cAMP levels. This influence extends to the Akt/mTOR pathway where the A3AR further modulates cellular survival and growth. Proteins like TDP1 integrate into the DNA damage repair pathway acting alongside other repair proteins ensuring genomic stability. Furthermore 5-HT2B and 5-HT2C receptors link to the phospholipase C pathway which impacts intracellular calcium levels and consequently various cellular activities.

Adenosine receptors are implicated in cardiovascular diseases due to their ability to influence heart rate and vasodilation. For example dysfunction in the Adenosine A1 Receptor can link to arrhythmias. Moreover A2a Receptor overactivity relates to Parkinson's disease as it disrupts dopamine signaling. Similarly alterations in 5-HT2C Receptor activity connect to psychiatric disorders like depression and anxiety owing to its role in serotonin regulation. ENT1's role in nucleoside transport has associations with neurological conditions when malfunctioning while aberrations in TDP1's repair function result in neurodegenerative conditions like Spinocerebellar Ataxia with Axonal Neuropathy (SCAN1).

Product protocols

Publications (2)

Recent publications for all applications. Explore the full list and refine your search

Journal of cellular physiology 235:2441-2451 PubMed31556103

2019

Acupuncture induces adenosine in fibroblasts through energy metabolism and promotes proliferation by activating MAPK signaling pathway via adenosine receptor.

Applications

Unspecified application

Species

Unspecified reactive species

Fei Qu,Yanru Cui,Jie Zeng,Mingyue Zhang,Shaying Qiu,Xiaoting Huang,Aishe Chen

Biochemical and biophysical research communication 497:850-856 PubMed29454963

2018

Adenosine receptors enhance the ATP-induced odontoblastic differentiation of human dental pulp cells.

Applications

Unspecified application

Species

Unspecified reactive species

Xiaosong Yi,Wei Wang,Qiufei Xie
View all publications

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