Kynurenic acidAn antagonist of NMDA and AMPA/kainate receptors

Kynurenic acid (CAS 492-27-3)

Kynurenic acid | CAS 492-27-3 is rated 5.0 out of 5 by 1.
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Synonym: 4-Hydroxyquinoline-2-carboxylic acid
Application: An antagonist of NMDA and AMPA/kainate receptors
CAS Number: 492-27-3
Purity: ≥98%
Molecular Weight: 189.17
Molecular Formula: C10H7NO3
* Refer to Certificate of Analysis for lot specific data (including water content).
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Kynurenic acid is a metabolite of tryptophan in mammals via the kynurenine pathway. Studies have observed that Kynurenic acid acts as a ligand to the GPR35 G protein-coupled receptor. The binding of Kynurenic acid to GPR35 has been noted to affect calcium mobilization and inositol phosphatase synthesis and may indicate potential signaling functions by Kynurenic acid via the GPR35 receptor. Additionally reported to be a broad spectrum, excitatory amino acid (EAA) antagonist. Other studies have reported that Kynurenic acid acts as an antagonist to mammalian ionotropic glutamate receptors especially NMDA (N-methyl-D-aspartate receptors).Kynurenic acid is an inhibitor of AChR α7, GluR and GlyR.

Also available as a Kynurenic acid, sodium salt (sc-358835)


References

1. Pittaluga, A., et al. 1997. J. Pharmacol. Exp. Ther. 283: 82-90. PMID: 9336311
2. Wong, A.Y et al. 2003. J. Neurosci. 23: 4868-4877. PMID: 12832509
3. Brooks, V.L., et al. 2004. Am. J. Physiol. Regul. Integr. Comp. Physiol. 287: R1359-R1368. PMID: 15319216
4. Nasif, F.J., et al. 2005. J. Neurosci. 25: 3674-3679. PMID: 15814798
5. Wang, J., et al. 2006. J. Biol. Chem. 281: 22021-22028. PMID: 16754668
6. Le Floc'h, N., et al. 2010. Amino Acids. [Epub ahead of print]. PMID: 20872026

Appearance :
Powder
Physical State :
Solid
Solubility :
Soluble in water (partly), hot alcohol, DMSO (75 mM), 0.1 M NaOH (50 mg/ml), and methanol.
Storage :
Store at 4° C
Melting Point :
275° C (lit.)(dec.)
Boiling Point :
358.36° C at 760 mmHg (Predicted)
Density :
1.43 g/cm3 (Predicted)
Refractive Index :
n20D 1.64 (Predicted)
IC50 :
Glutamate NMDA receptor: IC50 = 13.8 µM (rat); Glutamate (NMDA) receptor subunit zeta 1: IC50 = 40.2 µM (rat); Glutamate receptor ionotropic, AMPA: IC50 = 101 µM (rat); GPR35: EC5050 = 152 µM (human); Rattus norvegicus: IC50 = 167 µM
Ki Data :
Glutamate (NMDA) receptor subunit zeta 1: Ki= 5.4 µM (rat); Vesicular glutamate transporter 3: Ki= 1.3 mM (rat)
pK Values :
pKa: 3.49 (Predicted), pKb: 0.36 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
VB2080000
PubChem CID :
3845
Merck Index :
14: 5327
MDL Number :
MFCD00006753
EC Number :
207-751-5
Beilstein Registry :
147451
SMILES :
C1=CC=C2C(=C1)C(=O)C=C(N2)C(=O)O

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Certificate of Analysis

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Kynurenic acid  Product Citations

See how others have used Kynurenic acid. Click on the entry to view the PubMed entry .

Citations 1 to 2 of 2 total

PMID: # 23467467  Uwai, Y. et al. 2013. Int J Tryptophan Res. 6: 1-6.

PMID: # 22108572  Uwai, Y. et al. 2012. Pharmacol. Res. 65: 254-60.

Citations 1 to 2 of 2 total
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Rated 5 out of 5 by from Wang et al Wang et al. (PubMed ID 16754668) found that Kynurenic acid elicited calcium mobilization and inositol phosphate production in a GPR35-dependent manner in the presence of G(qi/o) chimeric G proteins and also inhibited lipopolysaccharide-induced tumor necrosis factor-alpha secretion in peripheral blood mononuclear cells. -SCBT Publication Review
Date published: 2015-01-22
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