7-Chlorokynurenic acid - CAS 18000-24-3
Category: Inhibitor
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Molecular Formula:
C10H6ClNO3
Molecular Weight:
223.62
COA:
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Targets:
NMDA Receptor
Description:
7-Chlorokynurenic acid is a water-soluble and very potent NMDA receptor antagonist acting at the strychnine-insensitive glycine binding site. It is also a potent competitive inhibitor of L-glutamate transport into synaptic vesicles. It is used in studies of schizophrenia and neuroprotection.
Purity:
≥98% by HPLC
Synonyms:
7-Chloro-4-hydroxyquinoline-2-carboxylic acid
MSDS:
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InChIKey:
UAWVRVFHMOSAPU-UHFFFAOYSA-N
InChI:
InChI=1S/C10H6ClNO3/c11-5-1-2-6-7(3-5)12-8(10(14)15)4-9(6)13/h1-4H,(H,12,13)(H,14,15)
Canonical SMILES:
C1=CC2=C(C=C1Cl)NC(=CC2=O)C(=O)O
1.Agonist-like character of the (R)-enantiomer of 1-hydroxy-3-amino-pyrrolid-2-one (HA-966).
Pullan LM;Verticelli AM;Paschetto KA Eur J Pharmacol. 1991 Sep 12;208(1):25-9.
HA-966 (1-hydroxy-3-amino-pyrrolid-2-one), an antagonist at the strychnine-insensitive glycine site on the N-methyl-D-aspartate (NMDA) receptor complex, only partially inhibits the binding of noncompetitive antagonists to the NMDA receptor but enhances the binding of the NMDA competitive antagonist CPP (3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic acid). Here we report that the IC50 of the active (R)-enantiomer of HA-966 for displacement of [3H]glycine binding is decreased in the presence of spermine, suggesting that spermine increases the affinity of (R)-HA-966 at the [3H]glycine binding site. The IC50 values of the agonist glycine and the partial agonist 1-aminocyclopropane-1-carboxylate are also decreased. The IC50 values of glycine antagonists 6,7-dinitroquinoxalin-2,3-dione and 7-chlorokynurenic acid are not significantly altered. The spermine shift represents the first demonstration of the agonist-like character of the (R)-enantiomer of HA-966 at the glycine site.
2.A slow intravenous infusion of N-methyl-DL-aspartate as a seizure model in the mouse.
Singh L;Oles RJ;Vass CA;Woodruff GN J Neurosci Methods. 1991 May;37(3):227-32.
A seizure model involving slow i.v. infusion of the excitatory amino acid N-methyl-DL-aspartate (NMDLA) in the mouse is described. It allows determination of the threshold doses of NMDLA required to elicit clonic and tonic seizures in individual mice. The NMDA receptor antagonists MK-801, CPP, ifenprodil and 7-chlorokynurenic acid (7-CLK), and diazepam dose-dependently increased the dose of NMDLA required to elicit a tonic seizure. CPP, 7-CLK and diazepam also increased the dose of NMDLA inducing clonic seizures. In contrast, ifenprodil at doses which antagonised tonic seizures had no effect on clonic seizures. The glycine and polyamine modulatory site agonists, D-serine and spermidine respectively, dose-dependently reduced the dose of NMDLA required to induce clonic and tonic seizures. The NMDLA infusion model appears to be more sensitive than the classical bolus injection test and can detect both anticonvulsant and proconvulsant actions mediated by the NMDA receptor complex.
3.A comparison of the effects of ethanol and the competitive glycine antagonist 7-chlorokynurenic acid on N-methyl-D-aspartic acid-induced neurotransmitter release from rat hippocampal slices.
Woodward JJ J Neurochem. 1994 Mar;62(3):987-91.
N-Methyl-D-aspartate (NMDA; 500 microM) stimulated the net release of preloaded tritiated norepinephrine from rat hippocampal slices. Both ethanol and the competitive glycine antagonist 7-chlorokynurenic acid (7-CK) dose-dependently inhibited NMDA-stimulated release without affecting basal, nonstimulated efflux. These inhibitory effects were readily reversed upon washout of the drugs. Over the concentration range tested (25-200 mM), ethanol inhibited approximately 65% of NMDA-stimulated release with an estimated IC50 of approximately 70 mM. In contrast, 7-CK fully inhibited release (> 95%) at a concentration of 30 microM with half-maximal inhibition occurring at approximately 2 microM. The combination of 7-CK (1-30 microM) and ethanol (25-100 mM) had an additive inhibitory effect on NMDA-stimulated release but did not alter the inhibitory potency of 7-CK. Calculated IC50 values for 7-CK in the presence of 25, 50, or 100 mM ethanol were (mean +/- SEM; microM) 2.33 (0.11), 2.38 (0.23), and 1.99 (0.30), respectively. 7-CK (3 microM) inhibited NMDA-stimulated [3H]norepinephrine release by approximately 50%. This inhibition was fully attenuated by the addition of the glycine agonist D-serine with complete reversal occurring at 30 microM D-serine.
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Chemical Structure

CAS 18000-24-3 7-Chlorokynurenic acid

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