Quisqualic acid

Quisqualic acid
IUPAC name

(2S)-2-amino-3-(3,5-dioxo-1,2,4-
oxadiazolidin-2-yl)propanoic acid
Identifiers
CAS number 52809-07-1 N
PubChem 40539
ChemSpider 37038 Y
DrugBank DB02999
KEGG C08296 Y
MeSH Quisqualic+Acid
ChEMBL CHEMBL279956 Y
IUPHAR ligand 1370
Jmol-3D images Image 1
Properties
Molecular formula C5H7N3O5
Molar mass 189.126 g/mol
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Quisqualic acid is an agonist for both AMPA receptors and group I metabotropic glutamate receptors.[1][2][3] It causes excitotoxicity and is used in neuroscience to selectively destroy neurons in the brain or spinal cord.[4][5][6] It 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 paralysis of the Japanese beetle.[7][8] Quisqualic acid is thought to mimic L-glutamic acid, which is a neurotransmitter in the insect neuromuscular junction and mammalian central nervous system.[9]

References

  1. ^ Jin R, Horning M, Mayer ML, Gouaux E. Mechanism of activation and selectivity in a ligand-gated ion channel: structural and functional studies of GluR2 and quisqualate. Biochemistry. 2002 Dec 31;41(52):15635-43. PMID 12501192
  2. ^ Kuang D, Hampson DR. Ion dependence of ligand binding to metabotropic glutamate receptors. Biochemical and Biophysical Research Communications. 2006 Jun 23;345(1):1-6. PMID 16674916
  3. ^ Zhang W, Robert A, Vogensen SB, Howe JR. The relationship between agonist potency and AMPA receptor kinetics. Biophysical Journal. 2006 Aug 15;91(4):1336-46. PMID 16731549
  4. ^ Muir JL, Page KJ, Sirinathsinghji DJ, Robbins TW, Everitt BJ. Excitotoxic lesions of basal forebrain cholinergic neurons: effects on learning, memory and attention. Behavioural Brain Research. 1993 Nov 30;57(2):123-31. PMID 7509608
  5. ^ Giovannelli L, Casamenti F, Pepeu G. 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. 1998;105(8-9):935-48. PMID 9869327
  6. ^ Lee JW, Furmanski O, Castellanos DA, Daniels LA, Hama AT, Sagen J. Prolonged nociceptive responses to hind paw formalin injection in rats with a spinal cord injury. Neuroscience Letters. 2008 Jul 11;439(2):212-5. PMID 18524486
  7. ^ Geraniums and Begonias: New Research on Old Garden Favorites (the March 2010 issue of Agricultural Research magazine.)
  8. ^ Ranger, C.M., Winter, R. E., Singh, A. P., Reding, M. E., Frantz, J. M., Locke, J. C., and Krause, C. R. 2011. Rare excitatory amino acid from flowers of zonal geranium responsible for paralyzing the Japanese beetle. Proceedings of the National Academy of Sciences. http://www.pnas.org/content/early/2010/12/29/1013497108.full.pdf+html
  9. ^ Usherwood, P. N. R. 1994. Insect glutamate receptors. Advances in Insect Biochemistry and Physiology. 24: 309-341.