Xanthurenic acid
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Names | |
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Preferred IUPAC name
4,8-Dihydroxyquinoline-2-carboxylic acid | |
Other names
Xanthuric acid
Xanthurenate 8-Hydroxykynurenic acid 4,8-Dihydroxyquinaldic acid | |
Identifiers | |
3D model (JSmol)
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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.000.373 |
EC Number |
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KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C10H7NO4 | |
Molar mass | 205.169 g·mol−1 |
Appearance | Yellow crystals |
Melting point | 286 °C (547 °F; 559 K) |
Insoluble | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Xanthurenic acid, or xanthurenate, is a chemical shown to induce gametogenesis of Plasmodium falciparum, the parasite that causes malaria.[2][3] It is found in the gut of the Anopheles mosquito.
Xanthurenic acid is a metabolic intermediate that accumulates and is excreted by pyridoxine (vitamin B6) deficient animals after the ingestion of tryptophan.[1][4]
Xanthurenic acid is suspected to be an endogenous agonist for Group II metabotropic glutamate receptors in humans.[5] It is also known to be a potent VGLUT inhibitor, thereby preventing the movement of glutamate from the cytoplasm into synaptic vesicles, an action that it mediates via competitive blockade of vesicular glutamate transporters (Ki = 0.19 mM).[6] In 2015[update] researchers reported a marked reduction of xanthurenic acid levels in the serum of patients with schizophrenia, describing this phenomenon as a potential trait marker for schizophrenia.[7]
See also
References
- ^ a b Merck Index, 11th Edition, 9977.
- ^ Billker, O; Lindo, V; Panico, M; Etienne, AE; Paxton, T; Dell, A; Rogers, M; Sinden, RE; Morris, HR (March 19, 1998). "Identification of xanthurenic acid as the putative inducer of malaria development in the mosquito". Nature. 392 (6673): 289–292. doi:10.1038/32667. PMID 9521324.
- ^ Garcia, GE; Wirtz, RA; Barr, JR; Woolfitt, A; Rosenberg, R (May 15, 1998). "Xanthurenic acid induces gametogenesis in Plasmodium, the malaria parasite". The Journal of Biological Chemistry. 273 (20): 12003–5. doi:10.1074/jbc.273.20.12003. PMID 9575140.
- ^ Xanthurenic acid at Sigma-Aldrich
- ^ Copeland, C. S.; Neale, S. A.; Salt, T. E. (2013). "Actions of Xanthurenic Acid, a putative endogenous Group II metabotropic glutamate receptor agonist, on sensory transmission in the thalamus". Neuropharmacology. 66: 133–142. doi:10.1016/j.neuropharm.2012.03.009. PMID 22491023.
- ^ Bartlett RD, Esslinger CS, Thompson CM, Bridges RJ (1998). "Substituted quinolines as inhibitors of L-glutamate transport into synaptic vesicles". Neuropharmacology. 37 (7): 839–46. doi:10.1016/s0028-3908(98)00080-x. PMID 9776380.
- ^ Fazio, F.; Lionetto, L.; Curto, M. (2015). "Xanthurenic Acid Activates mGlu2/3 Metabotropic Glutamate Receptors and is a Potential Trait Marker for Schizophrenia". Scientific Reports. 5: 17799. doi:10.1038/srep17799. PMC 4672300. PMID 26643205.