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Chemical Compound Review

IB-MECA     (2S,3S,4R,5R)-3,4-dihydroxy- 5-[6-[(3...

Synonyms: N(6)-Ibamu, SureCN465039, CF-101, CHEBI:73286, CTK8E8477, ...
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Disease relevance of IB-MECA

  • In addition, in melanoma tumor lesions derived from IB-MECA-treated mice, the expression level A3AR and the downstream key signaling proteins were modulated in the same pattern as was seen in vitro [1].
  • Higher doses of IB-MECA were lethal in C57 mice subjected to renal ischemia [2].
  • In addition, IB-MECA was able to inhibit forskolin-stimulated cAMP levels, which indicate the functional form of A3 receptor on the cell surface of these breast cancer cell lines [3].
  • 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 [4].
  • Weak activity of APNEA and IB-MECA discounts involvement of A3 receptors [5].

Psychiatry related information on IB-MECA

  • IB-MECA significantly diminished scopolamine- and MK-801-induced impairment of spontaneous alternation in Y-maze and learning abilities in passive avoidance task as well as reduced higher locomotor activity in MK-801-treated group [6].

High impact information on IB-MECA

  • METHODS: Rats received intraperitoneal injections of selective agonists of A1, A2a, and A3 adenosine receptors: 2-chloro-N(6)-cyclopentyladenosine (CCPA), CGS-21680 (CGS), or 1-deoxy-1-[6-[[(3-iodophenyl)methyl]amino]-9H-purin-9-yl]-N-methyl-be ta-D-ribofuranuronamide (IB-MECA), respectively [7].
  • Stimulation with the GiPCR ligands C5a and 1-deoxy-1-[6-[(3-iodophenyl)methyl]amino]-9H-purine-9-y1]-N-methyl-beta-D-ribofuranuronamide (IB-MECA) blocked the production of IL-12 p70 by human monocytes stimulated with LPS and IFN-gamma [8].
  • Nebulized IB-MECA directly induced lung mast cell degranulation in wild-type mice while having no effect in A(3) receptor knockout mice [9].
  • Accordingly, the level of beta-catenin responsive cell growth regulatory genes including c-myc and cyclin D1 was severely declined upon treatment of the cells with IB-MECA [10].
  • Here we demonstrate the ability of IB-MECA to decrease the levels of protein kinase A, a downstream effector of cAMP, and protein kinase B/Akt in melanoma cells [10].

Chemical compound and disease context of IB-MECA


Biological context of IB-MECA

  • Evaluation of beta-catenin, a key component of Wnt signaling pathway which, upon phosphorylation by GSK-3beta rapidly ubiquitinates, showed a substantial decrease in its level after IB-MECA treatment [10].
  • In addition, DNA breaks in cardiomyocytes undergoing apoptosis following treatment by IB-MECA were identified in situ using the nick end labeling of DNA ("TUNEL"-like) assay [13].
  • This result was further corroborated by showing that the two selective A1 and A3 receptor agonists, N-cyclopentyladenosine (CPA) and 1-deoxy-1-[6-[[(3-iodophenyl)methyl]amino]-9H-purin-9-yl]-N-methyl-be ta-D-ribofuranuronamide (IB-MECA) respectively, induced bone marrow cell proliferation in a manner similar to adenosine [14].
  • Administration of IB-MECA had no effect on any hemodynamic parameter measured including heart rate, first derivative of left ventricular pressure, aortic pressure, LAD coronary blood flow, or coronary collateral blood flow [4].
  • 2. Intradermal (i.d.) injection of adenosine and analogues induced increased microvascular permeability in a dose-dependent manner (IB-MECA > NECA > CPA > adenosine) [15].

Anatomical context of IB-MECA


Associations of IB-MECA with other chemical compounds


Gene context of IB-MECA

  • The high affinity adenosine A3 receptor agonist IB-MECA (1-deoxy-1-[6-[[(3-iodophenyl)methyl]amino]-9H-purin-9-yl]-N-methyl-beta-D-ribofuranuronamide) stimulated time (peak activation occurring after 5 min) and concentration-dependent (pEC50=9.0+/-0.2) increases in p42/p44 MAPK in CHO-A3 cells [12].
  • Using ADO receptor-specific analogs, we showed that highly selective A3 agonist N6-(3-iodobenzyl)-adenosine-5'-N'-methyluronamide (IB-MECA) inhibited LPS-induced TF activity expression more potently than A1 agonist R-phenylisopropyladenosine (R-PIA) and A2 agonist CGS 2180 [20].
  • Expression of iNOS mRNA and NO production were enhanced after 6 and 24 h respectively of IB-MECA treatment [21].
  • In contrast, the selective A3 agonist IB-MECA (EC50 1 nmol/L) stimulated angiopoietin-2 expression [22].
  • IB-MECA 100 microM downregulated HIAP1, NAIP and survivin mRNAs in HL-60, but not in HL-60R cells [23].

Analytical, diagnostic and therapeutic context of IB-MECA

  • RESULTS: Perfusion with the A1>A3 agonist R-PIA and the A3>A1 agonist IB-MECA was associated with reduced [3H]ryanodine binding, due to reduced B(max) (by about 20%), whereas K(d) and Ca(2+)-dependence of the binding reaction were unaffected [24].
  • An equivalent reduction in infarct size was observed when IB-MECA was administered immediately before reperfusion (13.1 +/- 3.9%) [4].
  • Nevertheless, pretreatment with IB-MECA before coronary occlusion produced a marked reduction in infarct size ( approximately 40% reduction) compared with the control group (13.0 +/- 3.2% vs. 25.2 +/- 3.7% of the area at risk, respectively) [4].
  • The highly selective A3AR agonist, IB-MECA was earlier shown to prevent the clinical and pathological manifestations of arthritis in experimental animal models of collagen and adjuvant induced arthritis (AIA) [25].
  • RT-PCR experiments showed that ryanodine receptor gene expression was not affected by IB-MECA [19].


  1. A3 adenosine receptor activation in melanoma cells: association between receptor fate and tumor growth inhibition. Madi, L., Bar-Yehuda, S., Barer, F., Ardon, E., Ochaion, A., Fishman, P. J. Biol. Chem. (2003) [Pubmed]
  2. A3 adenosine receptor knockout mice are protected against ischemia- and myoglobinuria-induced renal failure. Lee, H.T., Ota-Setlik, A., Xu, H., D'Agati, V.D., Jacobson, M.A., Emala, C.W. Am. J. Physiol. Renal Physiol. (2003) [Pubmed]
  3. An adenosine analog (IB-MECA) inhibits anchorage-dependent cell growth of various human breast cancer cell lines. Panjehpour, M., Karami-Tehrani, F. Int. J. Biochem. Cell Biol. (2004) [Pubmed]
  4. A3 adenosine receptor agonist IB-MECA reduces myocardial ischemia-reperfusion injury in dogs. Auchampach, J.A., Ge, Z.D., Wan, T.C., Moore, J., Gross, G.J. Am. J. Physiol. Heart Circ. Physiol. (2003) [Pubmed]
  5. Analysis of the atypical characteristics of adenosine receptors mediating negative inotropic and chronotropic responses of guinea-pig isolated atria and papillary muscles. Gardner, N.M., Broadley, K.J. Br. J. Pharmacol. (1999) [Pubmed]
  6. The influence of adenosine A3 receptor agonist: IB-MECA, on scopolamine- and MK-801-induced memory impairment. Rubaj, A., Zgodziński, W., Sieklucka-Dziuba, M. Behav. Brain Res. (2003) [Pubmed]
  7. Activation of adenosine A1-receptor pathway induces edema formation in the pancreas of rats. Satoh, A., Shimosegawa, T., Satoh, K., Ito, H., Kohno, Y., Masamune, A., Fujita, M., Toyota, T. Gastroenterology (2000) [Pubmed]
  8. G(i)-protein-dependent inhibition of IL-12 production is mediated by activation of the phosphatidylinositol 3-kinase-protein 3 kinase B/Akt pathway and JNK. la Sala, A., Gadina, M., Kelsall, B.L. J. Immunol. (2005) [Pubmed]
  9. Activation of murine lung mast cells by the adenosine A3 receptor. Zhong, H., Shlykov, S.G., Molina, J.G., Sanborn, B.M., Jacobson, M.A., Tilley, S.L., Blackburn, M.R. J. Immunol. (2003) [Pubmed]
  10. Evidence for involvement of Wnt signaling pathway in IB-MECA mediated suppression of melanoma cells. Fishman, P., Madi, L., Bar-Yehuda, S., Barer, F., Del Valle, L., Khalili, K. Oncogene (2002) [Pubmed]
  11. Distinct KATP channels mediate the antihypertrophic effects of adenosine receptor activation in neonatal rat ventricular myocytes. Xia, Y., Javadov, S., Gan, T.X., Pang, T., Cook, M.A., Karmazyn, M. J. Pharmacol. Exp. Ther. (2007) [Pubmed]
  12. Regulation of p42/p44 mitogen-activated protein kinase by the human adenosine A3 receptor in transfected CHO cells. Graham, S., Combes, P., Crumiere, M., Klotz, K.N., Dickenson, J.M. Eur. J. Pharmacol. (2001) [Pubmed]
  13. Induction of apoptosis in cardiac myocytes by an A3 adenosine receptor agonist. Shneyvays, V., Nawrath, H., Jacobson, K.A., Shainberg, A. Exp. Cell Res. (1998) [Pubmed]
  14. Adenosine acts as a chemoprotective agent by stimulating G-CSF production: a role for A1 and A3 adenosine receptors. Fishman, P., Bar-Yehuda, S., Farbstein, T., Barer, F., Ohana, G. J. Cell. Physiol. (2000) [Pubmed]
  15. The plasma protein extravasation induced by adenosine and its analogues in the rat dorsal skin: evidence for the involvement of capsaicin sensitive primary afferent neurones and mast cells. Esquisatto, L.C., Costa, S.K., Camargo, E.A., Ribela, M.T., Brain, S.D., de Nucci, G., Antunes, E. Br. J. Pharmacol. (2001) [Pubmed]
  16. Adenosine-induced apoptosis in glomerular mesangial cells. Zhao, Z., Kapoian, T., Shepard, M., Lianos, E.A. Kidney Int. (2002) [Pubmed]
  17. Pyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidine derivatives as highly potent and selective human A(3) adenosine receptor antagonists: influence of the chain at the N(8) pyrazole nitrogen. Baraldi, P.G., Cacciari, B., Romagnoli, R., Spalluto, G., Moro, S., Klotz, K.N., Leung, E., Varani, K., Gessi, S., Merighi, S., Borea, P.A. J. Med. Chem. (2000) [Pubmed]
  18. Apparent involvement of the A(2A) subtype adenosine receptor in the anti-inflammatory interactions of CGS 21680, cyclopentyladenosine, and IB-MECA with human neutrophils. Visser, S.S., Theron, A.J., Ramafi, G., Ker, J.A., Anderson, R. Biochem. Pharmacol. (2000) [Pubmed]
  19. Modulation of Cardiac Sarcoplasmic Reticulum Calcium Release by Aenosine: A protein Kinase C- Dependent Pathway. Ghelardoni, S., Frascarelli, S., Carnicelli, V., Ronca-Testoni, S., Zucchi, R. Mol. Cell. Biochem. (2006) [Pubmed]
  20. Adenosine inhibits tissue factor expression by LPS-stimulated human monocytes: involvement of the A3 adenosine receptor. Broussas, M., Cornillet-Lefèbvre, P., Potron, G., Nguyên, P. Thromb. Haemost. (2002) [Pubmed]
  21. Late preconditioning elicited by activation of adenosine A(3) receptor in heart: role of NF- kappa B, iNOS and mitochondrial K(ATP) channel. Zhao, T.C., Kukreja, R.C. J. Mol. Cell. Cardiol. (2002) [Pubmed]
  22. Mast cell-mediated stimulation of angiogenesis: cooperative interaction between A2B and A3 adenosine receptors. Feoktistov, I., Ryzhov, S., Goldstein, A.E., Biaggioni, I. Circ. Res. (2003) [Pubmed]
  23. Induction of apoptosis by the adenosine derivative IB-MECA in parental or multidrug-resistant HL-60 leukemia cells: possible relationship to the effects on inhibitor of apoptosis protein levels. Notarbartolo, M., Lo Cicero, S., Meli, M., Poma, P., Labbozzetta, M., Cervello, M., D'Alessandro, N. Chemotherapy. (2005) [Pubmed]
  24. A3 adenosine receptor stimulation modulates sarcoplasmic reticulum Ca(2+) release in rat heart. Zucchi, R., Yu, G., Ghelardoni, S., Ronca, F., Ronca-Testoni, S. Cardiovasc. Res. (2001) [Pubmed]
  25. IB-MECA, an A3 adenosine receptor agonist prevents bone resorption in rats with adjuvant induced arthritis. Rath-Wolfson, L., Bar-Yehuda, S., Madi, L., Ochaion, A., Cohen, S., Zabutti, A., Fishman, P. Clin. Exp. Rheumatol. (2006) [Pubmed]
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