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Merck

5.31145

mGlu7 Antagonist, XAP044

Synonym(s):

mGlu7 Antagonist, XAP044, 7-Hydroxy-3-(4-iodophenoxy)-4H-chromen-4-one, 7-Hydroxy-3-(4-iodophenoxy)-chromen-4-one, Metabotropic Glutamate Receptor Subtype 7 Antagonist, XAP-044

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About This Item

Empirical Formula (Hill Notation):
C15H9IO4
CAS Number:
Molecular Weight:
380.13
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
Assay:
≥97% (HPLC)
Form:
powder
Quality level:
Storage condition:
OK to freeze, protect from light
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assay

≥97% (HPLC)

Quality Level

form

powder

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze, protect from light

color

pale yellow

solubility

DMSO: 100 mg/mL

storage temp.

2-8°C

SMILES string

Ic1ccc(cc1)Oc2[c](c3c([o]c2)cc(cc3)O)=O

InChI

1S/C15H9IO4/c16-9-1-4-11(5-2-9)20-14-8-19-13-7-10(17)3-6-12(13)15(14)18/h1-8,17H

InChI key

XXZKJJYWINSUMJ-UHFFFAOYSA-N

General description

A blood-brain barrier permeable and bioavailable chromenone compound that acts as a potent, selective, and reversible antagonist of mGlu7 receptor (IC50 = 3.5 and 2.8 µM for mGlu7a and mGlu7b in CHO cells). Docks within the Venus flytrap domain (VFTD) close to the binding site of L-glutamate and functions as an orthosteric-like antagonist. Reduces DL-2-amino-4-phosphonobutyric acid (DL-AP4)-induced activation of human mGlu7b receptor (IC50 = 2.8 µM), but does not affect DL-AP4-induced activation of [35S]GTPγS binding by mGlu4 and mGlu6. Shown to diminish [35S]GTPγS binding by the human mGlu7/6 chimeric receptor harboring mGlu7 VFTD (IC50 = 2.5 µM). Displays weak binding affinity towards mGlu5 and mGlu8 receptors (IC50 >20 and 33 µM, respectively) and has no effect on GABA-induced activation of [35S]GTPγS binding by GABA-B receptors. Displays antidepressant and anxiolytic-like properties and selectively blocks long-term potentiation (LTP) in the lateral amygdala of wild type (IC50 = 88 nM), but not of mGlu7- deficient mice.

Please note that the molecular weight for this compound is batch-specific due to variable water content.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
mGlu7R
Reversible: yes
Target IC50: 3.5 and 2.8 &micro

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Gee, C.E., et al. 2014. J. Biol. Chem.289, 10975.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)


Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable



Certificates of Analysis (COA)

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