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pertaining to or containing any of a group of organic compounds of nitrogen derived from ammonia (同)aminic
the radical -NH2 (同)amino_group

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/11/11 10:58:57」(JST)

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AP5 or APV ((2R)-amino-5-phosphonovaleric acid; (2R)-amino-5-phosphonopentanoate) is a selective NMDA receptor antagonist that competitively inhibits the ligand (glutamate) binding site of NMDA receptors.^[1] AP5 blocks NMDA receptors in micromolar concentrations (~50 µM).

AP5 blocks the cellular analog of classical conditioning in the sea slug Aplysia californica, and has similar effects on Aplysia long-term potentiation (LTP), since NMDA receptors are required for both. It is sometimes used in conjunction with the calcium chelator BAPTA to determine whether NMDARs are required for a particular cellular process. AP5/APV has also been used to study NMDAR-dependent LTP in the mammalian hippocampus.^[2]

In general, AP5 is very fast-acting within in vitro preparations, and can block NMDA receptor action at a reasonably small concentration. The active isomer of AP5 is considered to be the D configuration, although many preparations are available as a racemic mixture of D- and L-isomers. It is useful to isolate the action of other glutamate receptors in the brain, i.e., AMPA and kainate receptors.

AP5 can block the conversion of a silent synapse to an active one, since this conversion is NMDA receptor-dependent.

AP5 was developed by Jeff Watkins and Harry Olverman.

References

^ Morris RG. Synaptic plasticity and learning: selective impairment of learning rats and blockade of long-term potentiation in vivo by the N-methyl-D-aspartate receptor antagonist AP5. Journal of Neuroscience. 1989 Sep;9(9):3040-57. PMID 2552039
^ Gustafsson B., Wigström H., Abraham W.C., and Huang Y.Y. Long-Term Potentiation in the Hippocampus Using Depolarizing Current Pulses as the Conditioning Stimulus to Single Volley Synaptic Potentials. Journal of Neuroscience. 1987 March;7(3):774-780

Cellular Analog of Differential Classical Conditioning in Aplysia: Disruption by the NMDA Receptor Antagonist DL-2-Amino-5-Phosphonovalerate

^ Laube, B; Hirai H, Sturgess M, Betz H, and Kuhse J (1997). "Molecular determinants of antagonists discrimination by NMDA receptor subunits: Analysis of the glutamate binding site on the NR2B subunit". Neuron 18 (3): 493–503. doi:10.1016/S0896-6273(00)81249-0. PMID 9115742.

UpToDate Contents

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English Journal

Preventive effect of theanine intake on stress-induced impairments of hippocamapal long-term potentiation and recognition memory.

Tamano H, Fukura K, Suzuki M, Sakamoto K, Yokogoshi H, Takeda A.SourceGraduate School of Pharmaceutical Sciences, University of Shizuoka, Global COE, Japan.
Brain research bulletin.Brain Res Bull.2013 Jun;95:1-6. doi: 10.1016/j.brainresbull.2013.02.005. Epub 2013 Feb 28.
Theanine, γ-glutamylethylamide, is one of the major amino acid components in green tea. On the basis of the preventive effect of theanine intake after birth on mild stress-induced attenuation of hippocamapal CA1 long-term potentiation (LTP), the present study evaluated the effect of theanine intake
PMID 23458739

The postsubiculum and spatial learning: the role of postsubicular synaptic activity and synaptic plasticity in hippocampal place cell, object, and object-location memory.

Bett D, Stevenson CH, Shires KL, Smith MT, Martin SJ, Dudchenko PA, Wood ER.SourceCentre for Cognitive and Neural Systems, School of Biomedical Sciences, University of Edinburgh, Edinburgh EH8 9JZ, United Kingdom.
The Journal of neuroscience : the official journal of the Society for Neuroscience.J Neurosci.2013 Apr 17;33(16):6928-43. doi: 10.1523/JNEUROSCI.5476-12.2013.
Visual landmarks exert stimulus control over spatial behavior and the spatially tuned firing of place, head-direction, and grid cells in the rodent. However, the neural site of convergence for representations of landmarks and representations of space has yet to be identified. A potential site of pla
PMID 23595751

Vertebrate intersectin1 is repurposed to facilitate cortical midline connectivity and higher order cognition.

Sengar AS, Ellegood J, Yiu AP, Wang H, Wang W, Juneja SC, Lerch JP, Josselyn SA, Henkelman RM, Salter MW, Egan SE.SourceProgram in Neurosciences and Mental Health, Hospital for Sick Children, Toronto, Ontario M5G 1X8, Canada.
The Journal of neuroscience : the official journal of the Society for Neuroscience.J Neurosci.2013 Feb 27;33(9):4055-65. doi: 10.1523/JNEUROSCI.4428-12.2013.
Invertebrate studies have highlighted a role for EH and SH3 domain Intersectin (Itsn) proteins in synaptic vesicle recycling and morphology. Mammals have two Itsn genes (Itsn1 and Itsn2), both of which can undergo alternative splicing to include DBL/PH and C2 domains not present in invertebrate Itsn
PMID 23447614

Japanese Journal

ATP-and Adenosine-Mediated Signaling in the Central Nervous System : The Role of Extracellular ATP in Hippocampal Long-Term Potentiation

Fujii Satoshi
Journal of pharmacological sciences 94(2), 103-106, 2004-02-01
… This ATP-induced LTP was blocked by addition of an N-methyl-<sc>D</sc>-aspartate (NMDA) glutamate receptor antagonist, <sc>D</sc>,<sc>L</sc>-2-amino-5-phosphonovalerate (5 μM). …
NAID 130000073859

海馬スライスにおける非線形リズムの周波数調節 : 興奮性シナプスと抑制性シナプスの活性バランスとリズム

新井潤,夏目季代久
電子情報通信学会技術研究報告. NLP, 非線形問題 103(504), 1-4, 2003-12-12
… このβ波に対してα-amino-3-hydroxy-5-methyl-4-isoxazole propionate(AMPA)受容体阻害薬である6-cyano-7-nitroquinoxaline-2,3-dione(CNQX)を投与することによって、β波は阻害された。 … また、N-methyl-D-aspartate(NMDA)受容体阻害薬である2-amino-5-phosphonovalerate(APV)を投与すると、β波の周波数は高くなった。 …
NAID 110003291370

Low Concentration of _<DL>-2-Amino-5-phosphonovalerate Induces Epileptiform Activity in Guinea Pig Hippocampal Slices

GORJI Ali,SPECKMANN Erwin-Josef
Epilepsia : journal of the International League against Epilepsy 42(10), 1228-1230, 2001-10-01
NAID 10010859681

Related Pictures

★リンクテーブル★

リンク元	「2-アミノ-5-ホスホノ吉草酸」「2-amino-5-phosphonovaleric acid」

「2-アミノ-5-ホスホノ吉草酸」

AP5
Names
	IUPAC name 2-amino-5-phosphonopentanoic acid
Identifiers
CAS Registry Number	76326-31-3
ChemSpider	119225
	InChI InChI=1S/C5H12NO5P/c6-4(5(7)8)2-1-3-12(9,10)11/h4H,1-3,6H2,(H,7,8)(H2,9,10,11)/t4-/m1/s1 ; Key: VOROEQBFPPIACJ-SCSAIBSYSA-N ; InChI=1/C5H12NO5P/c6-4(5(7)8)2-1-3-12(9,10)11/h4H,1-3,6H2,(H,7,8)(H2,9,10,11)/t4-/m1/s1; Key: VOROEQBFPPIACJ-SCSAIBSYBE ;
Jmol-3D images	Image
PubChem	135342
	SMILES O=P(O)(O)CCC[C@@H](N)C(=O)O ;
Properties
Chemical formula	C5H12NO5P
Molar mass	197.13 g/mol
Appearance	white solid
Density	1.529 g/mL
Boiling point	482.1 °C (899.8 °F; 755.2 K)
Solubility in water	Ammonium hydroxide, 50 mg/mL
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references