Xanthurenic acid

Xanthurenic acid ^[1]

Names
Preferred IUPAC name 4,8-Dihydroxyquinoline-2-carboxylic acid
Other names Xanthuric acid Xanthurenate 8-Hydroxykynurenic acid 4,8-Dihydroxyquinaldic acid
Identifiers
CAS Number	59-00-7  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:10072  N
ChemSpider	5497  N
ECHA InfoCard	100.000.373
EC Number	200-410-1
KEGG	C02470  N
PubChem CID	5699
UNII	58LAB1BG8J  Y
CompTox Dashboard (EPA)	DTXSID90207728
InChI InChI=1S/C10H7NO4/c12-7-3-1-2-5-8(13)4-6(10(14)15)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15) N Key: FBZONXHGGPHHIY-UHFFFAOYSA-N N InChI=1/C10H7NO4/c12-7-3-1-2-5-8(13)4-6(10(14)15)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15) Key: FBZONXHGGPHHIY-UHFFFAOYAE
SMILES OC2=CC(C(O)=O)=NC1=C(O)C=CC=C12
Properties
Chemical formula	C10H7NO4
Molar mass	205.169 g·mol−1
Appearance	Yellow crystals
Melting point	286 °C (547 °F; 559 K)
Solubility in water	Insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

Xanthurenic acid, or xanthurenate, is a metabolic intermediate that accumulates and is excreted by pyridoxine (vitamin B₆) deficient animals after the ingestion of tryptophan. ^{[1] [2]}

Xanthurenic acid is suspected to be an endogenous agonist for Group II metabotropic glutamate receptors in humans. ^[3] 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 (K_i = 0.19 mM). ^[4]

In 2015 ^[update] researchers reported a marked reduction of xanthurenic acid levels in the serum of patients with schizophrenia. ^[5] A recent meta-analysis showed that blood xanthurenic acid levels are lower in individuals suffering from bipolar disorder as well. ^[6]

Xanthurenic acid has also been shown to induce gametogenesis of Plasmodium falciparum , the parasite that causes malaria. ^{[7] [8]} It is found in the gut of the Anopheles mosquito.

See also

• Kynurenic acid
• 7-Chlorokynurenic acid

References

1. Merck Index , 11th Edition, 9977.
2. Xanthurenic acid at Sigma-Aldrich
3. 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. S2CID   37921378.
4. 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. S2CID   39853026.
5. 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. Bibcode:2015NatSR...517799F. doi:10.1038/srep17799. PMC   4672300 . PMID   26643205.
6. Bartoli, F; Misiak, B; Callovini, T; Cavaleri, D; Cioni, RM; Crocamo, C; Savitz, JB; Carrà, G (19 October 2020). "The kynurenine pathway in bipolar disorder: a meta-analysis on the peripheral blood levels of tryptophan and related metabolites". Molecular Psychiatry. 26 (7): 3419–3429. doi:10.1038/s41380-020-00913-1. PMID   33077852. S2CID   224314102.
7. 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. Bibcode:1998Natur.392..289B. doi:10.1038/32667. PMID   9521324. S2CID   2584314.
8. 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.