IB-MECA

• CAT Number: I001908
• CAS Number: 152918-18-8
• Molecular Formula: C18H19IN6O4
• Molecular Weight: 510.29
• Purity: ≥95%
• Target: adenosine A3 receptor
• Solubility: DMSO: ≥ 45 mg/mL
• Storage: 2-8°C
• IC50: 0.11 μM (EC50)
• IUPAC Name: (2S,3S,4R,5R)-3,4-dihydroxy-5-[6-[(3-iodophenyl)methylamino]purin-9-yl]-N-methyloxolane-2-carboxamide
• 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
• SMILES: CNC(=O)C1C(C(C(O1)N2C=NC3=C(N=CN=C32)NCC4=CC(=CC=C4)I)O)O

Piclidenoson (IB-MECA) is a first-in-class, orally active, selective adenosine A3 receptor (A3AR) agonist. Piclidenoson exhibits anti-proliferative and apoptosis-inducing effects in different types of cancer cells such as melanoma and leukemia. Piclidenoson can be used in the research of autoimmune inflammatory diseases and COVID-19.

Reference

1:The infarct-sparing effect of IB-MECA against myocardial ischemia/reperfusion injury in mice is mediated by sequential activation of adenosine A3 and A 2A receptors. Tian Y, Marshall M, French BA, Linden J, Yang Z.Basic Res Cardiol. 2015 Mar;110(2):16. doi: 10.1007/s00395-015-0473-x. Epub 2015 Feb 26. PMID: 25711314 2:Role of nitric oxide in the behavioral and neurochemical effects of IB-MECA in zebrafish. Maximino C, Gemaque J, Benzecry R, Lima MG, Batista Ede J, Picanço-Diniz DW, Oliveira KR, Herculano AM.Psychopharmacology (Berl). 2015 May;232(10):1671-80. doi: 10.1007/s00213-014-3799-4. Epub 2014 Nov 13. PMID: 25388291 3:The combination of Cl-IB-MECA with paclitaxel: a new anti-metastatic therapeutic strategy for melanoma. Soares AS, Costa VM, Diniz C, Fresco P.Cancer Chemother Pharmacol. 2014 Oct;74(4):847-60. doi: 10.1007/s00280-014-2557-y. Epub 2014 Aug 14. PMID: 25119183 4:Mitochondrial and caspase pathways are involved in the induction of apoptosis by IB-MECA in ovarian cancer cell lines. Abedi H, Aghaei M, Panjehpour M, Hajiahmadi S.Tumour Biol. 2014 Nov;35(11):11027-39. doi: 10.1007/s13277-014-2396-9. Epub 2014 Aug 6. PMID: 25095978 5:Agonist of the adenosine A3 receptor, IB-MECA, and inhibitor of cyclooxygenase-2, meloxicam, given alone or in a combination early after total body irradiation enhance survival of γ-irradiated mice. Hofer M, Pospíšil M, Dušek L, Hoferová Z, Komůrková D.Radiat Environ Biophys. 2014 Mar;53(1):211-5. doi: 10.1007/s00411-013-0500-y. Epub 2013 Nov 22. PMID: 24263216 6:Potentiation of cytotoxicity of paclitaxel in combination with Cl-IB-MECA in human C32 metastatic melanoma cells: A new possible therapeutic strategy for melanoma. Soares AS, Costa VM, Diniz C, Fresco P.Biomed Pharmacother. 2013 Oct;67(8):777-89. doi: 10.1016/j.biopha.2013.08.003. Epub 2013 Aug 23. PMID: 24035253 7:Thio-Cl-IB-MECA, a novel A₃ adenosine receptor agonist, suppresses angiogenesis by regulating PI3K/AKT/mTOR and ERK signaling in endothelial cells. Kim GD, Oh J, Jeong LS, Lee SK.Biochem Biophys Res Commun. 2013 Jul 19;437(1):79-86. doi: 10.1016/j.bbrc.2013.06.040. Epub 2013 Jun 21. PMID: 23791876 8:The effects of the adenosine A3 receptor agonist IB-MECA on sodium taurocholate-induced experimental acute pancreatitis. Prozorow-Krol B, Korolczuk A, Czechowska G, Slomka M, Madro A, Celinski K.Arch Pharm Res. 2013 Sep;36(9):1126-32. doi: 10.1007/s12272-013-0126-2. Erratum in: Arch Pharm Res. 2013 Sep;36(9):1167. PMID: 23625750 Free PMC Article9:IB-MECA, an adenosine A(3) receptor agonist, does not influence survival of lethally γ-irradiated mice. Hofer M, Pospíšil M, Dušek L, Hoferová Z, Komůrková D.Physiol Res. 2012;61(6):649-54. Epub 2012 Oct 25. PMID: 23098658 Free Article10:Adoptive immunotherapy with Cl-IB-MECA-treated CD8+ T cells reduces melanoma growth in mice. Montinaro A, Forte G, Sorrentino R, Luciano A, Palma G, Arra C, Adcock IM, Pinto A, Morello S.PLoS One. 2012;7(9):e45401. doi: 10.1371/journal.pone.0045401. Epub 2012 Sep 24. PMID: 23028986 Free PMC Article