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=CC=CN=C1C(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)
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 |
|---|---|---|
| Effects of nerve and fibroblast growth factors on the production of nitric oxide in experimental model of Huntington's disease. | 2002-06-11 |
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| Quinolinic acid stimulates synaptosomal glutamate release and inhibits glutamate uptake into astrocytes. | 2002-06 |
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| Maintenance of susceptibility to neurodegeneration following intrastriatal injections of quinolinic acid in a new transgenic mouse model of Huntington's disease. | 2002-05 |
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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. | 2002-05 |
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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+. | 2002-04-29 |
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| Neural cells from primary human striatal xenografts migrate extensively in the adult rat CNS. | 2002-04 |
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| Antioxidant properties of new chalcogenides against lipid peroxidation in rat brain. | 2002-04 |
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| Positron emission tomography and ex vivo and in vitro autoradiography studies on dopamine D2-like receptor degeneration in the quinolinic acid-lesioned rat striatum: comparison of [11C]raclopride, [11C]nemonapride and [11C]N-methylspiperone. | 2002-04 |
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| Excitatory amino acids differentially regulate the expression of GDNF, neurturin, and their receptors in the adult rat striatum. | 2002-04 |
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| Excitotoxic and metabolic damage to the rodent striatum: role of the P75 neurotrophin receptor and glial progenitors. | 2002-03-18 |
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| Increased sensitivity to N-methyl-D-aspartate receptor-mediated excitotoxicity in a mouse model of Huntington's disease. | 2002-03-14 |
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| Hunting for excitement: NMDA receptors in Huntington's disease. | 2002-03-14 |
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| Quinolinate phosphoribosyltransferase: kinetic mechanism for a type II PRTase. | 2002-03-12 |
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| Mechanisms of the protective effect of L-alanine to D-galactosamine-induced hepatocellular injury: comparative studies of L-alanine and pyruvate. | 2002-03-08 |
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| Blockade of striatal adenosine A2A receptor reduces, through a presynaptic mechanism, quinolinic acid-induced excitotoxicity: possible relevance to neuroprotective interventions in neurodegenerative diseases of the striatum. | 2002-03-01 |
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| The clinical significance of cerebrospinal fluid levels of kynurenine pathway metabolites and lactate in severe malaria. | 2002-03-01 |
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| Endogenous neurotoxine-quinolinic acid is increased in renal allograft recipients. | 2002-03 |
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| Effect of systemic L-DOPA administration on extracellular kynurenate levels in the rat striatum. | 2002-03 |
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| Enhanced neuronal damage by co-administration of quinolinic acid and free radicals, and protection by adenosine A2A receptor antagonists. | 2002-03 |
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| Striatopallidal neurons are selectively protected by neurturin in an excitotoxic model of Huntington's disease. | 2002-03 |
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| Tryptophan metabolism via the kynurenine pathway in experimental chronic renal failure. | 2002-03 |
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| The role of the ventrolateral nucleus of the thalamus in the switching of descending influences to motor activity in the rat. | 2002-02-13 |
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| Function of the hypothalamo-pituitary-adrenocortical system during ontogenesis in rats with inherited stress-induced arterial hypertension. | 2002-02-13 |
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| Immediate-early gene response to methamphetamine, haloperidol, and quinolinic acid is not impaired in Huntington's disease transgenic mice. | 2002-02-01 |
|
| Concurrent quantification of quinolinic, picolinic, and nicotinic acids using electron-capture negative-ion gas chromatography-mass spectrometry. | 2002-02-01 |
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| Ebselen blocks the quinolinic acid-induced production of thiobarbituric acid reactive species but does not prevent the behavioral alterations produced by intra-striatal quinolinic acid administration in the rat. | 2002-02-01 |
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| Identification of CD40 ligand in Alzheimer's disease and in animal models of Alzheimer's disease and brain injury. | 2002-01-05 |
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| Behavioral and morphological comparison of two nonhuman primate models of Huntington's disease. | 2002-01 |
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| The effects of prelimbic and infralimbic lesions on working memory for visual objects in rats. | 2002-01 |
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| Metabolic changes in quinolinic acid-lesioned rat striatum detected non-invasively by in vivo (1)H NMR spectroscopy. | 2001-12-01 |
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| Hypothalamic digoxin mediated model for oncogenesis. | 2001-12 |
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| Neuroprotective effect of interleukin-6 and IL6/IL6R chimera in the quinolinic acid rat model of Huntington's syndrome. | 2001-12 |
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| IFN-beta1b induces kynurenine pathway metabolism in human macrophages: potential implications for multiple sclerosis treatment. | 2001-12 |
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| Kynurenine and its metabolites in the rat with experimental renal insufficiency. | 2001-12 |
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| 17Beta-estradiol attenuates quinolinic acid insult in the rat hippocampus. | 2001-12 |
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| TrkB and TrkC are differentially regulated by excitotoxicity during development of the basal ganglia. | 2001-12 |
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| Immunohistochemical visualization of newly formed quinolinate in the normal and excitotoxically lesioned rat striatum. | 2001-12 |
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| Lesions of the basolateral amygdala disrupt selective aspects of reinforcer representation in rats. | 2001-11-15 |
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| Localizing value of alpha-methyl-L-tryptophan PET in intractable epilepsy of neocortical origin. | 2001-11-13 |
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| Synthesis and release of neurotoxic kynurenine metabolites by human monocyte-derived macrophages. | 2001-11-01 |
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| IGF-1 and bFGF reduce glutaric acid and 3-hydroxyglutaric acid toxicity in striatal cultures. | 2001-11 |
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| The possible crucial role of iron accumulation combined with low tryptophan, zinc and manganese in carcinogenesis. | 2001-11 |
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| Resistance to NMDA toxicity correlates with appearance of nuclear inclusions, behavioural deficits and changes in calcium homeostasis in mice transgenic for exon 1 of the huntington gene. | 2001-11 |
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| Mice transgenic for exon 1 of the Huntington's disease gene display reduced striatal sensitivity to neurotoxicity induced by dopamine and 6-hydroxydopamine. | 2001-11 |
|
| 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. | 2001-10-19 |
|
| Increased cortical kynurenate content in schizophrenia. | 2001-10-01 |
|
| Influence of adenine-induced renal failure on tryptophan-niacin metabolism in rats. | 2001-10 |
|
| Kynurenine production and catabolism in fetal sheep with embolized or nonembolized placentas. | 2001-10 |
|
| Basolateral amygdala lesions disrupt latent inhibitionin rats. | 2001-09-01 |
|
| Hypothalamic digoxin, hemispheric dominance and the acquired immunodeficiency syndrome. | 2001 |
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.
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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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DTXSID8041327
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89-00-9
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D017378
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SUBSTANCE RECORD
