Kynurenic acid - CAS 492-27-3
Category: Inhibitor
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Molecular Formula:
C10H7NO3
Molecular Weight:
189.17
COA:
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Targets:
AMPAR | NMDA Receptor
Description:
Kynurenic acid is a product of L-Tryptophan metabolism. It is a non-selective antagonist at NMDA and AMPA/kainate receptors. It could block kainic acid neurotoxicity. It has neruoactive activity having anticonvulsant and antiexcitotoxic properties.
Purity:
≥98% by HPLC
Synonyms:
4-Hydroxy-2-quinolinecarboxylic Acid; 4-Hydroxy-quinaldic Acid; 2-Carboxy-4-hydroxyquinoline; 4-Hydroxyquinaldic Acid; Quinurenic Acid; NSC 58973; 4-Hydroxyquinoline-2-carboxylic acid
MSDS:
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InChIKey:
HCZHHEIFKROPDY-UHFFFAOYSA-N
InChI:
InChI=1S/C10H7NO3/c12-9-5-8(10(13)14)11-7-4-2-1-3-6(7)9/h1-5H,(H,11,12)(H,13,14)
Canonical SMILES:
C1=CC=C2C(=C1)C(=O)C=C(N2)C(=O)O
1.Microbial metabolism of quinoline and related compounds. XX. Quinaldic acid 4-oxidoreductase from Pseudomonas sp. AK-2 compared to other procaryotic molybdenum-containing hydroxylases.
Sauter M1, Tshisuaka B, Fetzner S, Lingens F. Biol Chem Hoppe Seyler. 1993 Nov;374(11):1037-46.
Quinaldic acid 4-oxidoreductase from Pseudomonas sp. AK-2 catalyses the hydroxylation of quinoline 2-carboxylic (quinaldic acid) to 4-hydroxyquinoline 2-carboxylic acid (kynurenic acid) with concomitant reduction of a suitable electron acceptor. An analogous hydroxylation in para-position relative to the N-heteroatom was only recently described for quinaldine 4-oxidoreductase (de Beyer & Lingens, 1993, Biol. Chem. Hoppe-Seyler 374, 101-110) and for quinaldic acid 4-oxidoreductase from Serratia marcescens 2CC-1 (Fetzner & Lingens, 1993, Biol. Chem. Hoppe-Seyler 374, 363-376). Quinaldic acid 4-oxidoreductase from Pseudomonas putida AK-2 was purified 78-fold to electrophoretic homogeneity with a recovery of 22%. The native enzyme (300 kDa) was composed of three subunits with molecular masses of 90, 34 and 20 kDa, indicating an alpha 2 beta 2 gamma 2 structure. Quinaldic acid 4-oxidoreductase contained FAD, molybdenum, iron and acid-labile sulfur in a ratio of 2:2:8:8.
2.Effects of selected pharmacological agents on avian auditory and vestibular compound action potentials.
Irons-Brown SR1, Jones TA. Hear Res. 2004 Sep;195(1-2):54-66.
Glutamate is currently the consensus candidate for the hair cell transmitter in the inner ear of vertebrates. However, other candidate transmitter systems have been proposed and there may be differences in this regard for auditory and vestibular neuroepithelia. In the present study, perilymphatic perfusion was used to deliver prescribed concentrations of ten drugs to the interstitial fluids of the inner ear of hatchling chickens (n = 124). Dose-response curves were obtained for four of these pharmacological agents. The work was carried out in part to distinguish further the neuroepithelial chemical receptors mediating auditory and vestibular compound action potentials (CAPs). Kainic acid (KA) eliminated both auditory and vestibular responses. D-alpha-Aminoadipic acid (DAA) and dizocilpine maleate (MK-801), both NMDA-specific antagonists, failed to alter vestibular CAPs at any concentration. MK-801 significantly and selectively reduced auditory CAPs at concentrations equal to or greater than 1 mM.
3.Complex formation in aqueous solution and in the solid state of the potent insulin-enhancing V(IV)O2+ compounds formed by picolinate and quinolinate derivatives.
Lodyga-Chruscinska E1, Micera G, Garribba E. Inorg Chem. 2011 Feb 7;50(3):883-99. doi: 10.1021/ic101475x. Epub 2011 Jan 12.
The complexation of V(IV)O(2+) ion with 10 picolinate and quinolinate derivatives, provided with the donor set (N, COO(-)), was studied in aqueous solution and in the solid state through the combined application of potentiometric (pH-titrations), spectroscopic (EPR, UV/vis and IR spectroscopy), and computational (density functional theory (DFT) calculations) methods. Such derivatives, that form potent insulin-enhancing V(IV)O(2+) compounds, are picolinic (picH), 6-methylpicolinic (6-mepicH), 3-methylpicolinic (3-mepicH), 5-butylpicolinic or fusaric (fusarH), 6-methyl-2,3-pyridindicarboxylic (6-me-2,3-pdcH(2)), 2-pyridylacetic (2-pyacH), 2-quinolinecarboxylic or quinaldic (quinH), 4-hydroxyquinoline-2-carboxylic or kynurenic (kynurH), 1-isoquinolinecarboxylic (1-iqcH) and 3-isoquinolinecarboxylic (3-iqcH) acid. On the basis of the potentiometric, spectroscopic, and DFT results, they were divided into the classes A, B, and C. The ligands belonging to class A (3-mepicH, 1-iqcH, 2-pyacH) form square pyramidal complexes in aqueous solution and in the solid state, and those belonging to class B (picH, fusarH, 3-iqcH) form cis-octahedral species, in which the two ligands adopt an (equatorial-equatorial) and an (equatorial-axial) arrangement and one water molecule occupies an equatorial site in cis position with respect to the V═O bond.
4.Behavioral and neurochemical actions of the strychnine-insensitive glycine receptor antagonist, 7-chlorokynurenate, in rats.
Kretschmer BD1, Bubser M, Schmidt WJ. Eur J Pharmacol. 1995 Jun 23;280(1):37-45.
The present study investigated if blockade of the modulatory glycine receptor of the NMDA receptor complex influences the expression of behavior (sniffing stereotypy and locomotion) and dopamine metabolism in rats as it has been shown for NMDA receptor antagonists. The glycine receptor antagonist, 7-chlorokynurenate (7-chloro-4-hydroxyquinoline-2-carboxylic acid), induced a dose-dependent sniffing stereotypy but had no effect on locomotion when it was given i.c.v. The glycine receptor agonist, D-cycloserine (D-4-amino-3-isoxazolidinone), antagonized the sniffing stereotypy. 7-Chlorokynurenate had no influence on dopamine metabolism in the striatum and the nucleus accumbens, but moderately decreased the metabolism in the prefrontal cortex. Comparison of behavioral and neurochemical outcomes suggests that the failure to induce locomotion correlates with the unchanged dopamine metabolism in the basal ganglia, while sniffing stereotypy does not.
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CAS 492-27-3 Kynurenic acid

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