AB-MECA

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 571317

CAS#: 152918-27-9

Description: AB-MECA is a binding molecule to A3 adenosine receptors, i.e. an agonist ligand. AB-MECA labels primarily A1 and A2A adenosine receptors in rat brain.


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AB-MECA is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 571317
Name: AB-MECA
CAS#: 152918-27-9
Chemical Formula: C18H20IN7O4
Exact Mass: 525.0621
Molecular Weight: 525.31
Elemental Analysis: C, 41.16; H, 3.84; I, 24.16; N, 18.67; O, 12.18


Synonym: AB-MECA

IUPAC/Chemical Name: beta-D-Ribofuranuronamide, 1-(6-(((4-amino-3-iodophenyl)methyl)amino)-9H-purin-9-yl)-1-deoxy-N-methyl-

InChi Key: LOGOEBMHHXYBID-MOROJQBDSA-N

InChi Code: InChI=1S/C18H20IN7O4/c1-21-17(29)14-12(27)13(28)18(30-14)26-7-25-11-15(23-6-24-16(11)26)22-5-8-2-3-10(20)9(19)4-8/h2-4,6-7,12-14,18,27-28H,5,20H2,1H3,(H,21,29)(H,22,23,24)/t12-,13+,14-,18+/m0/s1

SMILES Code: O[C@H]1[C@H](N2C=NC3=C(NCC4=CC=C(N)C(I)=C4)N=CN=C23)O[C@H](C(NC)=O)[C@H]1O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

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2: Olah ME, Gallo-Rodriguez C, Jacobson KA, Stiles GL. 125I-4-aminobenzyl-5'-N-methylcarboxamidoadenosine, a high affinity radioligand for the rat A3 adenosine receptor. Mol Pharmacol. 1994 May;45(5):978-82. PubMed PMID: 8190112; PubMed Central PMCID: PMC5553074.

3: Mikus EG, Szeredi J, Boer K, Tímári G, Finet M, Aranyi P, Galzin AM. Evaluation of SSR161421, a novel orally active adenosine A3 receptor antagonist on pharmacology models. Eur J Pharmacol. 2013 Jan 15;699(1-3):172-9. doi: 10.1016/j.ejphar.2012.11.049. Epub 2012 Dec 5. PubMed PMID: 23219796.

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7: Fossetta J, Jackson J, Deno G, Fan X, Du XK, Bober L, Soudé-Bermejo A, de Bouteiller O, Caux C, Lunn C, Lundell D, Palmer RK. Pharmacological analysis of calcium responses mediated by the human A3 adenosine receptor in monocyte-derived dendritic cells and recombinant cells. Mol Pharmacol. 2003 Feb;63(2):342-50. PubMed PMID: 12527805.

8: Taliani S, Trincavelli ML, Cosimelli B, Laneri S, Severi E, Barresi E, Pugliesi I, Daniele S, Giacomelli C, Greco G, Novellino E, Martini C, Da Settimo F. Modulation of A2B adenosine receptor by 1-Benzyl-3-ketoindole derivatives. Eur J Med Chem. 2013 Nov;69:331-7. doi: 10.1016/j.ejmech.2013.09.001. Epub 2013 Sep 8. PubMed PMID: 24077183.

9: Kozma E, Kumar TS, Federico S, Phan K, Balasubramanian R, Gao ZG, Paoletta S, Moro S, Spalluto G, Jacobson KA. Novel fluorescent antagonist as a molecular probe in A(3) adenosine receptor binding assays using flow cytometry. Biochem Pharmacol. 2012 Jun 1;83(11):1552-61. doi: 10.1016/j.bcp.2012.02.019. Epub 2012 Mar 1. PubMed PMID: 22402302; PubMed Central PMCID: PMC3322254.

10: Lane JR, Beukers MW, Mulder-Krieger T, Ijzerman AP. The endocannabinoid 2-arachidonylglycerol is a negative allosteric modulator of the human A3 adenosine receptor. Biochem Pharmacol. 2010 Jan 1;79(1):48-56. doi: 10.1016/j.bcp.2009.07.024. Epub 2009 Aug 7. PubMed PMID: 19665453.

11: Gao ZG, Van Muijlwijk-Koezen JE, Chen A, Müller CE, Ijzerman AP, Jacobson KA. Allosteric modulation of A(3) adenosine receptors by a series of 3-(2-pyridinyl)isoquinoline derivatives. Mol Pharmacol. 2001 Nov;60(5):1057-63. PubMed PMID: 11641434; PubMed Central PMCID: PMC3953614.

12: Giannaccini G, Betti L, Palego L, Fabbrini L, Schmid L, Castagna M, Giusti L, Mascia G, Lucacchini A. Species comparison of adenosine receptor subtypes in brain and testis. Neurochem Res. 2008 May;33(5):852-60. Epub 2007 Nov 7. PubMed PMID: 17987385.

13: Varani K, Cacciari B, Baraldi PG, Dionisotti S, Ongini E, Borea PA. Binding affinity of adenosine receptor agonists and antagonists at human cloned A3 adenosine receptors. Life Sci. 1998;63(5):PL 81-7. PubMed PMID: 9714428.

14: Yates L, Clark JH, Martin TJ, James S, Broadley KJ, Kidd EJ. Radioligand binding and functional responses of ligands for human recombinant adenosine A(3) receptors. Auton Autacoid Pharmacol. 2006 Apr;26(2):191-200. PubMed PMID: 16553647.

15: Buenestado A, Grassin Delyle S, Arnould I, Besnard F, Naline E, Blouquit-Laye S, Chapelier A, Bellamy JF, Devillier P. The role of adenosine receptors in regulating production of tumour necrosis factor-alpha and chemokines by human lung macrophages. Br J Pharmacol. 2010 Mar;159(6):1304-11. doi: 10.1111/j.1476-5381.2009.00614.x. Epub 2010 Feb 5. PubMed PMID: 20136829; PubMed Central PMCID: PMC2848934.

16: Saki M, Tsumuki H, Nonaka H, Shimada J, Ichimura M. KF26777 (2-(4-bromophenyl)-7,8-dihydro-4-propyl-1H-imidazo[2,1-i]purin-5(4H)-one dihydrochloride), a new potent and selective adenosine A3 receptor antagonist. Eur J Pharmacol. 2002 May 31;444(3):133-41. PubMed PMID: 12063073.

17: Jacobson KA, Nikodijević O, Shi D, Gallo-Rodriguez C, Olah ME, Stiles GL, Daly JW. A role for central A3-adenosine receptors. Mediation of behavioral depressant effects. FEBS Lett. 1993 Dec 20;336(1):57-60. PubMed PMID: 8262217; PubMed Central PMCID: PMC4287251.

18: Ji XD, Melman N, Jacobson KA. Interactions of flavonoids and other phytochemicals with adenosine receptors. J Med Chem. 1996 Feb 2;39(3):781-8. PubMed PMID: 8576921.

19: Brandon CI, Vandenplas M, Dookwah H, Murray TF. Cloning and pharmacological characterization of the equine adenosine A3 receptor. J Vet Pharmacol Ther. 2006 Aug;29(4):255-63. PubMed PMID: 16846462.

20: Ongini E, Dionisotti S, Gessi S, Irenius E, Fredholm BB. Comparison of CGS 15943, ZM 241385 and SCH 58261 as antagonists at human adenosine receptors. Naunyn Schmiedebergs Arch Pharmacol. 1999 Jan;359(1):7-10. PubMed PMID: 9933143.