Xanthurenic acid
 | |
| Names | |
|---|---|
| IUPAC name
8-Hydroxy-4-oxo-1H-quinoline-2-carboxylic acid | |
| Other names
Xanthuric acid Xanthurenate 8-Hydroxykynurenic acid 4,8-Dihydroxyquinaldic acid | |
| Identifiers | |
59-00-7  | |
| 3D model (Jmol) | Interactive image |
| ChEBI | CHEBI:10072  |
| ChemSpider | 5497 |
| ECHA InfoCard | 100.000.373 |
| EC Number | 200-410-1 |
| KEGG | C02470 |
| PubChem | 5699 |
| |
| |
| Properties | |
| C10H7NO4 | |
| Molar mass | 205.17 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). | |
| verify (what is ?) | |
| Infobox references | |
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 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
- 1 2 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.