Quisqualic acid
Names
IUPAC name
3-(3,5-Dioxo-1,2,4-oxadiazolidin-2-yl)-L -alanine
Systematic IUPAC name
(2S )-2-Amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid
Identifiers
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard
100.164.809
EC Number
KEGG
MeSH
Quisqualic+Acid
UNII
InChI=1S/C5H7N3O5/c6-2(3(9)10)1-8-4(11)7-5(12)13-8/h2H,1,6H2,(H,9,10)(H,7,11,12)/t2-/m0/s1
Y Key: ASNFTDCKZKHJSW-REOHCLBHSA-N
Y InChI=1/C5H7N3O5/c6-2(3(9)10)1-8-4(11)7-5(12)13-8/h2H,1,6H2,(H,9,10)(H,7,11,12)/t2-/m0/s1
Key: ASNFTDCKZKHJSW-REOHCLBHBE
O=C1NC(=O)ON1C[C@H](N)C(=O)O
Properties
C5 H7 N3 O5
Molar mass
189.126 g/mol
Melting point
187 to 188 °C (369 to 370 °F; 460 to 461 K) decomposes
Hazards
GHS labelling :[ 1]
Warning
H302 , H312 , H332
P261 , P264 , P270 , P271 , P280 , P301+P317 , P302+P352 , P304+P340 , P317 , P321 , P330 , P362+P364 , P501
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Quisqualic acid is an agonist of the AMPA , kainate , and group I metabotropic glutamate receptors . It is one of the most potent AMPA receptor agonists known.[ 2] [ 3] [ 4] [ 5] It causes excitotoxicity and is used in neuroscience to selectively destroy neurons in the brain or spinal cord.[ 6] [ 7] [ 8] Quisqualic acid occurs naturally in the seeds of Quisqualis species.
Research conducted by the USDA Agricultural Research Service , has demonstrated quisqualic acid is also present within the flower petals of zonal geranium (Pelargonium x hortorum ) and is responsible for causing rigid paralysis of the Japanese beetle .[ 9] [ 10] Quisqualic acid is thought to mimic L-glutamic acid , which is a neurotransmitter in the insect neuromuscular junction and mammalian central nervous system.[ 11]
^ "Quisqualic acid" . pubchem.ncbi.nlm.nih.gov .
^ Jin R, Horning M, Mayer ML, Gouaux E (December 2002). "Mechanism of activation and selectivity in a ligand-gated ion channel: structural and functional studies of GluR2 and quisqualate". Biochemistry . 41 (52): 15635–15643. doi :10.1021/bi020583k . PMID 12501192 .
^ Kuang D, Hampson DR (June 2006). "Ion dependence of ligand binding to metabotropic glutamate receptors" . Biochemical and Biophysical Research Communications . 345 (1): 1–6. doi :10.1016/j.bbrc.2006.04.064 . PMID 16674916 .
^ Zhang W, Robert A, Vogensen SB, Howe JR (August 2006). "The relationship between agonist potency and AMPA receptor kinetics" . Biophysical Journal . 91 (4): 1336–1346. Bibcode :2006BpJ....91.1336Z . doi :10.1529/biophysj.106.084426 . PMC 1518651 . PMID 16731549 .
^ Bigge CF, Boxer PA, Ortwine DF (August 1996). "AMPA/Kainate Receptors" . Current Pharmaceutical Design . 2 (4): 397–412. doi :10.2174/1381612802666220925204342 . S2CID 252560966 .
^ Muir JL, Page KJ, Sirinathsinghji DJ, Robbins TW, Everitt BJ (November 1993). "Excitotoxic lesions of basal forebrain cholinergic neurons: effects on learning, memory and attention". Behavioural Brain Research . 57 (2): 123–131. doi :10.1016/0166-4328(93)90128-d . PMID 7509608 . S2CID 3994174 .
^ Giovannelli L, Casamenti F, Pepeu G (4 November 1998). "C-fos expression in the rat nucleus basalis upon excitotoxic lesion with quisqualic acid: a study in adult and aged animals". Journal of Neural Transmission . 105 (8–9): 935–948. doi :10.1007/s007020050103 . PMID 9869327 . S2CID 24942954 .
^ Lee JW, Furmanski O, Castellanos DA, Daniels LA, Hama AT, Sagen J (July 2008). "Prolonged nociceptive responses to hind paw formalin injection in rats with a spinal cord injury" . Neuroscience Letters . 439 (2): 212–215. doi :10.1016/j.neulet.2008.05.030 . PMC 2680189 . PMID 18524486 .
^ Flores A (March 2010). "Geraniums and Begonias: New Research on Old Garden Favorites" . Agricultural Research Magazine .
^ Ranger CM, Winter RE, Singh AP, Reding ME, Frantz JM, Locke JC, Krause CR (January 2011). "Rare excitatory amino acid from flowers of zonal geranium responsible for paralyzing the Japanese beetle" . Proceedings of the National Academy of Sciences of the United States of America . 108 (4): 1217–1221. Bibcode :2011PNAS..108.1217R . doi :10.1073/pnas.1013497108 . PMC 3029778 . PMID 21205899 .
^ Usherwood PN (1 January 1994). "Insect Glutamate Receptors". Advances in Insect Physiology . 24 : 309–341. doi :10.1016/S0065-2806(08)60086-7 . ISBN 9780120242245 .