使君子氨酸

化合物

使君子氨酸(英語:Quisqualic acid)是一种AMPA受体、红藻氨酸受体和I型代谢型谷氨酸受体激动剂,也是已知最强的AMPA受体激动剂[1][2][3][4]。由于它具有兴奋毒性,被广泛用于神经科学研究中,选择性地破坏大脑中的神经元或脊髓[5][6][7]。使君子氨酸存在于使君子科物种的种子中。 一项由美国农业部进行的研究显示,使君子氨酸也存在于天竺葵属的花瓣中,并能使其天敌甲壳虫神经系统瘫痪[8][9]。其作用机理为,使君子氨酸可被视为L-谷氨酸的类似物,可以作为昆虫神经肌肉结和哺乳动物中枢神经系统的神经递质[10]

使君子氨酸
IUPAC名
(2S)-2-amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid
识别
CAS号 52809-07-1  checkY
PubChem 40539
ChemSpider 37038
SMILES
 
  • O=C1NC(=O)ON1C[C@H](N)C(=O)O
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
InChIKey ASNFTDCKZKHJSW-REOHCLBHBE
DrugBank DB02999
KEGG C08296
MeSH Quisqualic+Acid
IUPHAR配体 1372
性质
化学式 C5H7N3O5
摩尔质量 189.126 g/mol g·mol⁻¹
熔点 187 - 188 °C(272 K)
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

另见

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参考文献

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  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. ^ Bentham Science Publishers. Current Pharmaceutical Design. Bentham Science Publishers. August 1996: 399– [2018-09-07]. (原始内容存档于2019-03-13). 
  5. ^ 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
  6. ^ 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
  7. ^ 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
  8. ^ Geraniums and Begonias: New Research on Old Garden Favorites页面存档备份,存于互联网档案馆) (the March 2010 issue of Agricultural Research magazine.)
  9. ^ 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
  10. ^ Usherwood, P. N. R. 1994. Insect glutamate receptors. Advances in Insect Biochemistry and Physiology. 24: 309-341.