Quisqualic acid

Quisqualic acid
Names
	IUPAC name (2S)-2-amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid
Identifiers
CAS Number	52809-07-1 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL279956 ;
ChemSpider	37038 ;
DrugBank	DB02999 ;
ECHA InfoCard	100.164.809
IUPHAR/BPS	1372; 1370;
KEGG	C08296 ;
MeSH	Quisqualic+Acid
PubChem CID	40539;
UNII	8OC22C1B99 ;
CompTox Dashboard (EPA)	DTXSID20896927 ;
	InChI 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 Key: ASNFTDCKZKHJSW-REOHCLBHSA-N ; 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;
	SMILES O=C1NC(=O)ON1C[C@H](N)C(=O)O;
Properties
Chemical formula	C5H7N3O5
Molar mass	189.126 g/mol
Melting point	187 to 188 °C (369 to 370 °F; 460 to 461 K) decomposes
	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

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.[1][2][3][4] It causes excitotoxicity and is used in neuroscience to selectively destroy neurons in the brain or spinal cord.[5][6][7] 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.[8][9] Quisqualic acid is thought to mimic L-glutamic acid, which is a neurotransmitter in the insect neuromuscular junction and mammalian central nervous system.[10]

References

Jin, Rongsheng; Horning, Michelle; Mayer, Mark L.; Gouaux, Eric (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, Donghui; Hampson, David R. (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, Wei; Robert, Antoine; Vogensen, Stine B.; Howe, James R. (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, Christopher F; Boxer, Peter A; Ortwine, Daniel F (August 1996). "AMPA/Kainate Receptors". Current Pharmaceutical Design. 2 (4): 397–412.
Muir, Janice L.; Page, Keith J.; Sirinathsinghji, D.J.S.; Robbins, Trevor W.; Everitt, Barry J. (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, Jeung Woon; Furmanski, Orion; Castellanos, Daniel A.; Daniels, Linda A.; Hama, Aldric T.; Sagen, Jacqueline (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.
Geraniums and Begonias: New Research on Old Garden Favorites (the March 2010 issue of Agricultural Research magazine.)
Ranger, Christopher M.; Winter, Rudolph E.; Singh, Ajay P.; Reding, Michael E.; Frantz, Jonathan M.; Locke, James C.; Krause, Charles R. (31 December 2010). "Rare excitatory amino acid from flowers of zonal geranium responsible for paralyzing the Japanese beetle". Proceedings of the National Academy of Sciences. 108 (4): 1217–1221. doi:10.1073/pnas.1013497108. PMC 3029778. PMID 21205899.
Usherwood, P. N. R. (1 January 1994). "Insect Glutamate Receptors". Advances in Insect Physiology. 24: 309–341. doi:10.1016/S0065-2806(08)60086-7. ISBN 9780120242245.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[1] Jin, Rongsheng; Horning, Michelle; Mayer, Mark L.; Gouaux, Eric (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.

[2] Kuang, Donghui; Hampson, David R. (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.

[3] Zhang, Wei; Robert, Antoine; Vogensen, Stine B.; Howe, James R. (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.

[Publishers1996-4] Bigge, Christopher F; Boxer, Peter A; Ortwine, Daniel F (August 1996). "AMPA/Kainate Receptors". Current Pharmaceutical Design. 2 (4): 397–412.

[5] Muir, Janice L.; Page, Keith J.; Sirinathsinghji, D.J.S.; Robbins, Trevor W.; Everitt, Barry J. (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.

[6] 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.

[7] Lee, Jeung Woon; Furmanski, Orion; Castellanos, Daniel A.; Daniels, Linda A.; Hama, Aldric T.; Sagen, Jacqueline (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.

[8] Geraniums and Begonias: New Research on Old Garden Favorites (the March 2010 issue of Agricultural Research magazine.)

[9] Ranger, Christopher M.; Winter, Rudolph E.; Singh, Ajay P.; Reding, Michael E.; Frantz, Jonathan M.; Locke, James C.; Krause, Charles R. (31 December 2010). "Rare excitatory amino acid from flowers of zonal geranium responsible for paralyzing the Japanese beetle". Proceedings of the National Academy of Sciences. 108 (4): 1217–1221. doi:10.1073/pnas.1013497108. PMC 3029778. PMID 21205899.

[10] Usherwood, P. N. R. (1 January 1994). "Insect Glutamate Receptors". Advances in Insect Physiology. 24: 309–341. doi:10.1016/S0065-2806(08)60086-7. ISBN 9780120242245.

Quisqualic acid

See also

References