Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C7H5NO4 |
| Molecular Weight | 167.1189 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C1=C(N=CC=C1)C(O)=O
InChI
InChIKey=GJAWHXHKYYXBSV-UHFFFAOYSA-N
InChI=1S/C7H5NO4/c9-6(10)4-2-1-3-8-5(4)7(11)12/h1-3H,(H,9,10)(H,11,12)
| Molecular Formula | C7H5NO4 |
| Molecular Weight | 167.1189 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Quinolinic acid is an endogenous N-methyl-D-aspartate receptor agonist synthesized from L-tryptophan via the kynurenine pathway and thereby has the potential of mediating N-methyl-D-aspartate neuronal damage and dysfunction. Elevated cerebrospinal fluid levels of quinolinic acid are correlated with the severity of neuropsychological deficits in patients who have AIDS. It can act as an endogenous brain excitotoxin when released by activated macrophages. Quinolinic acid is being used as a research tool to examine the role of excitotoxicity in neuronal degeneration associated with a number of neurological diseases (Alzheimer's disease, Huntington's disease, Parkinson's disease) which involve selective neurotransmitter deficits.
CNS Activity
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Comparative analysis of superoxide dismutase activity between acute pharmacological models and a transgenic mouse model of Huntington's disease. | 2001 Apr |
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| IFN-beta1b induces kynurenine pathway metabolism in human macrophages: potential implications for multiple sclerosis treatment. | 2001 Dec |
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| Kynurenine and its metabolites in the rat with experimental renal insufficiency. | 2001 Dec |
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| Metabolic changes in quinolinic acid-lesioned rat striatum detected non-invasively by in vivo (1)H NMR spectroscopy. | 2001 Dec 1 |
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| Neuroprotection by estrogen via extracellular signal-regulated kinase against quinolinic acid-induced cell death in the rat hippocampus. | 2001 Feb |
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| Regional changes in kynurenic acid, quinolinic acid, and glial fibrillary acidic protein concentrations in the fetal sheep brain after experimentally induced placental insufficiency. | 2001 Jan |
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| Expression of brain-derived neurotrophic factor in cortical neurons is regulated by striatal target area. | 2001 Jan 1 |
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| Effects of dietary pyrazinamide, an antituberculosis agent, on the metabolism of tryptophan to niacin and of tryptophan to serotonin in rats. | 2001 Jun |
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| Oligodendrocyte killing by quinolinic acid in vitro. | 2001 Mar 30 |
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| Synthesis and release of neurotoxic kynurenine metabolites by human monocyte-derived macrophages. | 2001 Nov 1 |
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| Influence of adenine-induced renal failure on tryptophan-niacin metabolism in rats. | 2001 Oct |
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| Increased cortical kynurenate content in schizophrenia. | 2001 Oct 1 |
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| The role of the primate amygdala in conditioned reinforcement. | 2001 Oct 1 |
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| Differential expression of active, phosphorylation-dependent MAP kinases, MAPK/ERK, SAPK/JNK and p38, and specific transcription factor substrates following quinolinic acid excitotoxicity in the rat. | 2001 Oct 19 |
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| Basolateral amygdala lesions disrupt latent inhibitionin rats. | 2001 Sep 1 |
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| Neural cells from primary human striatal xenografts migrate extensively in the adult rat CNS. | 2002 Apr |
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| Antioxidant properties of new chalcogenides against lipid peroxidation in rat brain. | 2002 Apr |
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| Excitatory amino acids differentially regulate the expression of GDNF, neurturin, and their receptors in the adult rat striatum. | 2002 Apr |
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| Cloning of human 3-hydroxyanthranilic acid dioxygenase in Escherichia coli: characterisation of the purified enzyme and its in vitro inhibition by Zn2+. | 2002 Apr 29 |
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| Function of the hypothalamo-pituitary-adrenocortical system during ontogenesis in rats with inherited stress-induced arterial hypertension. | 2002 Jan-Feb |
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| Increased sensitivity to N-methyl-D-aspartate receptor-mediated excitotoxicity in a mouse model of Huntington's disease. | 2002 Mar 14 |
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| Excitotoxic and metabolic damage to the rodent striatum: role of the P75 neurotrophin receptor and glial progenitors. | 2002 Mar 18 |
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| Distinct nuclear and cytoplasmic localization of caspase cleavage products in two models of induced apoptotic death in dopamine neurons of the substantia nigra. | 2002 May |
Sample Use Guides
The effects of quinolinic acid (QUIN) on glutamate-induced excitotoxicity were examined in primary cultures of rat cerebellar granule neurons. Exposing these neurons to QUIN (< or =2.5 mM) in the presence of glucose and Mg2+ had no effect on their viability. Although pretreating neurons with QUIN (10 microM) for 6 h did not reduce necrotic death induced by glutamate exposure in the absence of glucose and Mg2+, QUIN pretreatment significantly suppressed glutamate-induced apoptosis by 68% (as indicated by DNA fragmentation) in cultures containing glucose and Mg2+. Furthermore, the N-methyl-D-aspartate (NMDA) receptor antagonist AP-5 reversed QUIN-induced neuroprotection, while the non-NMDA antagonist CNQX had no effect. This study demonstrates that pathophysiologically relevant concentrations of QUIN can protect neurons from apoptosis mediated via the NMDA receptor.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 02:15:33 GMT 2023
by
admin
on
Sat Dec 16 02:15:33 GMT 2023
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| Record UNII |
F6F0HK1URN
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C542
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F6F0HK1URN
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DB01796
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m9460
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201-874-8
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13127
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16675
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QUINOLINIC ACID
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C113236
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