M227
MRS 1191
solid
Synonym(s):
3-Ethyl-5-benzyl-2-methyl-4-phenylethynyl-6-phenyl-1,4-(±)-dihydropyridine-3,5-dicarboxylate
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About This Item
Empirical Formula (Hill Notation):
C31H27NO4
CAS Number:
Molecular Weight:
477.55
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
form
solid
color
white
solubility
DMSO: >10 mg/mL
ethanol: >10 mg/mL
H2O: insoluble
storage temp.
−20°C
SMILES string
CCOC(=O)C1=C(C)NC(c2ccccc2)=C(C1C#Cc3ccccc3)C(=O)OCc4ccccc4
InChI
1S/C31H27NO4/c1-3-35-30(33)27-22(2)32-29(25-17-11-6-12-18-25)28(26(27)20-19-23-13-7-4-8-14-23)31(34)36-21-24-15-9-5-10-16-24/h4-18,26,32H,3,21H2,1-2H3
InChI key
SNVFDPHQAOXWJZ-UHFFFAOYSA-N
Biochem/physiol Actions
MRS 1191 is putative A3 adenosine receptor antagonist, highly selective for human A3 receptor vs human A1 receptor. MRS 1067, MRS 1191 and MRS 1220 were found to be competitive in saturation binding studies using the agonist radioligand [125I]AB-MECA at cloned human brain A3 receptors expressed in HEK-293 cells. Antagonism was demonstrated in functional assays consisting of agonist-induced inhibition of adenylate cyclase and the stimulation of binding of [35S]guanosine 5′-O-(3-thiotriphosphate) ([35S]GTP-gamma-S) to the associated G-proteins. Activation of the human A3 receptor in A3R-CHO results in markedly impaired cell cycle progression, suggesting an important role for this adenosine receptor subtype in cell cycle regulation and cell growth. Activation of adenosine A3 receptors by Cl-IBMECA (100 nM) increased the magnitude of theta-burst induced LTP (from 1.2+/-0.6% in the control solution to 25.5+/-0.8% in the presence of Cl-IBMECA) and attenuated LTD (from 30.0+/-5.5% decrease in the control solution to 13.6+/-6.6% decrease in the presence of Cl-IBMECA). The selective adenosine A3 receptor antagonist, MRS 1191 (5-10 μM), prevented the effects of Cl-IBMECA. These findings indicate a functional role for adenosine A3 receptors in the modulation of synaptic plasticity.
Caution
Photosensitive
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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J L Jiang et al.
Journal of medicinal chemistry, 39(23), 4667-4675 (1996-11-08)
An approach to designing dihydropyridines that bind to adenosine receptors without binding to L-type calcium channels has been described. 1,4-Dihydropyridine derivatives substituted with beta-styryl or phenylethynyl groups at the 4-position and aryl groups at the 6-position were synthesized and found
K A Jacobson et al.
Neuropharmacology, 36(9), 1157-1165 (1997-11-19)
The effects of putative A3 adenosine receptor antagonists of three diverse chemical classes (the flavonoid MRS 1067, the 6-phenyl-1,4-dihydropyridines MRS 1097 and MRS 1191, and the triazoloquinazoline MRS 1220) were characterized in receptor binding and functional assays. MRS1067, MRS 1191
Marlon De Ita et al.
Life sciences, 145, 85-92 (2015-12-19)
Almost every eukaryotic cell releases ATP under certain conditions. The idea that ATP induces the release of ATP has been scantly investigated. We explored this possibility by assessing the rate of exogenous ATP breakdown (measured by phosphates production) by human
T V Dunwiddie et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 17(2), 607-614 (1997-01-15)
The adenosine A3 receptor is expressed in brain, but the consequences of activation of this receptor on electrophysiological activity are unknown. We have characterized the actions of a selective adenosine A3 receptor agonist, 2-chloro-N6-(3-lodobenzyl)-adenosine-5'-N-methyluronamide (Cl-IB-MECA), and a selective A3 receptor
Laura Fontenas et al.
Cell reports, 27(1), 115-128 (2019-04-04)
During development, oligodendrocyte progenitor cells (OPCs) migrate extensively throughout the spinal cord. However, their migration is restricted at transition zones (TZs). At these specialized locations, unique glial cells in both zebrafish and mice play a role in preventing peripheral OPC
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