MRE 3008-F20 | CAS#252979-43-4 | adenosine receptor antagonist

MedKoo Cat#: 563155 | Name: MRE 3008-F20

Description:

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

MRE 3008-F20 is a potent antagonist of the human A3 adenosine receptors.

Chemical Structure

MRE 3008-F20

CAS#252979-43-4

Theoretical Analysis

MedKoo Cat#: 563155

Name: MRE 3008-F20

CAS#: 252979-43-4

Chemical Formula: C21H20N8O3

Exact Mass: 432.1658

Molecular Weight: 432.44

Elemental Analysis: C, 58.33; H, 4.66; N, 25.91; O, 11.10

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Synonym

MRE 3008-F20; MRE 3008F20; MRE 3008 F20; MRE-3008-F20; MRE3008F20; MRE3008F20; MCP-NECA; MCP NECA; MCPNECA;

IUPAC/Chemical Name

1-(2-Furan-2-yl-8-propyl-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-yl)-3-(4-methoxy-phenyl)-urea

InChi Key

CJRNHKSLHHWUAB-UHFFFAOYSA-N

InChi Code

InChI=1S/C21H20N8O3/c1-3-10-28-12-15-17(26-28)24-20(25-21(30)22-13-6-8-14(31-2)9-7-13)29-19(15)23-18(27-29)16-5-4-11-32-16/h4-9,11-12H,3,10H2,1-2H3,(H2,22,24,25,26,30)

SMILES Code

O=C(NC1=CC=C(OC)C=C1)NC2=NC3=NN(CCC)C=C3C4=NC(C5=CC=CO5)=NN24

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

>3 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).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

MRE3008F20 is a highly efficient, highly selective and radioactive adenosine A3 receptor (AA3R) antagonist (Ki=1.8 nM).

In vitro activity:

A3 receptors were studied with the new A3 adenosine receptor antagonist [3H]-MRE 3008F20, the only A3 selective radioligand currently available. Saturation experiments revealed a single high affinity binding site with KD of 3.3+/-0.7 nM and Bmax of 291+/-50 fmol x mg(-1) of protein. Reference: Br J Pharmacol. 2001 Nov;134(6):1215-26. https://pubmed.ncbi.nlm.nih.gov/11704641/

In vivo activity:

TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 432.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Merighi S, Varani K, Gessi S, Cattabriga E, Iannotta V, Ulouglu C, Leung E, Borea PA. Pharmacological and biochemical characterization of adenosine receptors in the human malignant melanoma A375 cell line. Br J Pharmacol. 2001 Nov;134(6):1215-26. doi: 10.1038/sj.bjp.0704352. PMID: 11704641; PMCID: PMC1573044. 2. Gessi S, Varani K, Merighi S, Morelli A, Ferrari D, Leung E, Baraldi PG, Spalluto G, Borea PA. Pharmacological and biochemical characterization of A3 adenosine receptors in Jurkat T cells. Br J Pharmacol. 2001 Sep;134(1):116-26. doi: 10.1038/sj.bjp.0704254. PMID: 11522603; PMCID: PMC1572937.

In vitro protocol:

In vivo protocol:

TBD

1: Kim SK, Gao ZG, Jeong LS, Jacobson KA. Docking studies of agonists and antagonists suggest an activation pathway of the A3 adenosine receptor. J Mol Graph Model. 2006 Dec;25(4):562-77. Epub 2006 May 9. PubMed PMID: 16793299. 2: Merighi S, Benini A, Mirandola P, Gessi S, Varani K, Leung E, Maclennan S, Borea PA. Adenosine modulates vascular endothelial growth factor expression via hypoxia-inducible factor-1 in human glioblastoma cells. Biochem Pharmacol. 2006 Jun 28;72(1):19-31. Epub 2006 Mar 29. PubMed PMID: 16682012. 3: Merighi S, Varani K, Gessi S, Klotz KN, Leung E, Baraldi PG, Borea PA. Binding thermodynamics at the human A(3) adenosine receptor. Biochem Pharmacol. 2002 Jan 15;63(2):157-61. PubMed PMID: 11841789. 4: Gessi S, Varani K, Merighi S, Cattabriga E, Iannotta V, Leung E, Baraldi PG, Borea PA. A(3) adenosine receptors in human neutrophils and promyelocytic HL60 cells: a pharmacological and biochemical study. Mol Pharmacol. 2002 Feb;61(2):415-24. PubMed PMID: 11809867. 5: Merighi S, Varani K, Gessi S, Cattabriga E, Iannotta V, Ulouglu C, Leung E, Borea PA. Pharmacological and biochemical characterization of adenosine receptors in the human malignant melanoma A375 cell line. Br J Pharmacol. 2001 Nov;134(6):1215-26. PubMed PMID: 11704641; PubMed Central PMCID: PMC1573044. 6: Gessi S, Varani K, Merighi S, Morelli A, Ferrari D, Leung E, Baraldi PG, Spalluto G, Borea PA. Pharmacological and biochemical characterization of A3 adenosine receptors in Jurkat T cells. Br J Pharmacol. 2001 Sep;134(1):116-26. PubMed PMID: 11522603; PubMed Central PMCID: PMC1572937. 7: Varani K, Merighi S, Gessi S, Klotz KN, Leung E, Baraldi PG, Cacciari B, Romagnoli R, Spalluto G, Borea PA. [(3)H]MRE 3008F20: a novel antagonist radioligand for the pharmacological and biochemical characterization of human A(3) adenosine receptors. Mol Pharmacol. 2000 May;57(5):968-75. PubMed PMID: 10779381. 8: Baraldi PG, Cacciari B, Romagnoli R, Varani K, Merighi S, Gessi S, Borea PA, Leung E, Hickey SL, Spalluto G. Synthesis and preliminary biological evaluation of [3H]-MRE 3008-F20: the first high affinity radioligand antagonist for the human A3 adenosine receptors. Bioorg Med Chem Lett. 2000 Feb 7;10(3):209-11. Erratum in: Bioorg Med Chem Lett 2000 Jun 19;10(12):1403. PubMed PMID: 10698437.

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