Xanthurenic acid[ 1]
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 N
ChEBI
CHEBI:10072 N
ChemSpider
5497 N
EC Number
200-410-1
Jmol interactive 3D
Image
KEGG
C02470 N
PubChem
5699
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
OC2=CC(C(O)=O)=NC1=C(O)C=CC=C12
Properties
C10 H7 NO4
Molar mass
205.17 g/mol
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).
N verify (what is Y N ?)
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]
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 .
Receptor
(ligands )
AMPA
NMDA
Antagonists: Competitive antagonists: AP5 (APV)
AP7
CGP-37849
CGP-39551
CGP-39653
CGP-40116
CGS-19755
CPP
LY-233,053
LY-235,959
LY-274,614
MDL-100,453
Midafotel (d-CPPene)
NPC-12,626
NPC-17,742
PBPD
PEAQX
Perzinfotel
PPDA
SDZ-220581
Selfotel ; Noncompetitive antagonists: ARR-15,896
Caroverine
Dexanabinol
FPL-12495
FR-115,427
Hodgkinsine
Magnesium
MDL-27,266
NPS-1506
Psychotridine
Zinc ; Uncompetitive pore blockers: 2-MDP
3-HO-PCP
3-MeO-PCE
3-MeO-PCMo
3-MeO-PCP
4-MeO-PCP
8A-PDHQ
18-MC
α-Endopsychosin
Alaproclate
Amantadine
Aptiganel
Arketamine
ARL-12,495
ARL-15,896-AR
ARL-16,247
Budipine
Conaridine
Delucemine
Dexoxadrol
Dextrallorphan
Dieticyclidine
Diphenidine
Dizocilpine
Ephenidine
Esketamine
Etoxadrol
Eticyclidine
Fluorolintane
Gacyclidine
Ibogaine
Ibogamine
Indantadol
Ketamine
Ketobemidone
Lanicemine
Loperamide
Memantine
Methadone (Levomethadone )
Methorphan (Dextromethorphan
Levomethorphan )
Methoxetamine
Methoxphenidine
Milnacipran
Morphanol (Dextrorphan
Levorphanol )
NEFA
Neramexane
Nitromemantine
Nitrous oxide
Noribogaine
Norketamine
Orphenadrine
PCPr
Pethidine (meperidine)
Phencyclamine
Phencyclidine
Propoxyphene
Remacemide
Rhynchophylline
Rimantadine
Rolicyclidine
Sabeluzole
Tabernanthine
Tenocyclidine
Tiletamine
Tramadol
Xenon ; Glycine site antagonists: 4-Cl-KYN (AV-101)
5,7-DCKA
7-CKA
ACC
ACEA-1011
ACEA-1328
AV-101
Carisoprodol
CGP-39653
CNQX
DNQX
Felbamate
Gavestinel
GV-196,771
Kynurenic acid
Kynurenine
L-689,560
L-701,324
Licostinel (ACEA-1021)
LU-73,068
MDL-105,519
Meprobamate
MRZ 2/576
PNQX
ZD-9379 ; NR2B subunit antagonists: Besonprodil
CERC-301 (MK-0657)
CO-101,244 (PD-174,494)
Eliprodil
Haloperidol
Ifenprodil
Isoxsuprine
Nylidrin
Ro8-4304
Ro25-6981
Traxoprodil ; Polyamine site antagonists: Arcaine
Co 101676
Diaminopropane
Diethylenetriamine
Huperzine A
Putrescine
Ro 25-6981 ; Unclassified/unsorted antagonists: Bumetanide
Chloroform
Cyclopropane
D -αAA
Diethyl ether
Enflurane
Ethanol
Flufenamic acid
Flupirtine
Furosemide
Halothane
Isoflurane
Metaphit
Methoxyflurane
Niflumic acid
Piretanide
Toluene
Transcrocetin (saffron )
Trichloroethane
Trichloroethanol
Trichloroethylene
Xylene
Kainate
mGlu1
mGlu2
mGlu3
mGlu4
mGlu5
mGlu6
mGlu7
mGlu8
Transporter
(blockers )
Enzyme
(inhibitors )
Others