This article is about the chemical compound. For the Star Wars Rebels TV series character, see AP-5.
AP5 (also known as APV, (2R)-amino-5-phosphonovaleric acid, or (2R)-amino-5-phosphonopentanoate) is a chemical compound used as a biochemical tool to study various cellular processes. It 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 Aplysialong-term potentiation (LTP), since NMDA receptors are required for both.[2] It is sometimes used in conjunction with the calciumchelatorBAPTA 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.[3]
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.
^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
^Cellular Analog of Differential Classical Conditioning in Aplysia: Disruption by the NMDA Receptor Antagonist DL-2-Amino-5-Phosphonovalerate
^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
External linksedit
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.
December 15, 2023
this, article, about, chemical, compound, star, wars, rebels, series, character, also, known, amino, phosphonovaleric, acid, amino, phosphonopentanoate, chemical, compound, used, biochemical, tool, study, various, cellular, processes, selective, nmda, receptor. This article is about the chemical compound For the Star Wars Rebels TV series character see AP 5 AP5 also known as APV 2R amino 5 phosphonovaleric acid or 2R amino 5 phosphonopentanoate is a chemical compound used as a biochemical tool to study various cellular processes It 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 mM AP5 NamesPreferred IUPAC name 2R 2 Amino 5 phosphonopentanoic acidIdentifiersCAS Number 76326 31 3 Y3D model JSmol Interactive imageChemSpider 119225 YECHA InfoCard 100 150 904PubChem CID 135342UNII 39PJ29YY8Z YCompTox Dashboard EPA DTXSID201000239InChI 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 YKey VOROEQBFPPIACJ SCSAIBSYSA N YInChI 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 s1Key VOROEQBFPPIACJ SCSAIBSYBESMILES O P O O CCC C H N C O OPropertiesChemical formula C5H12NO5PMolar mass 197 13 g molAppearance white solidDensity 1 529 g mLBoiling point 482 1 C 899 8 F 755 2 K Solubility in water Ammonium hydroxide 50 mg mLExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references 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 2 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 3 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 See also editAMPA AP7 drug KainateReferences edit 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 Cellular Analog of Differential Classical Conditioning in Aplysia Disruption by the NMDA Receptor Antagonist DL 2 Amino 5 Phosphonovalerate Gustafsson B Wigstrom 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 780External links editLaube 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 Retrieved from https en wikipedia org w index php title AP5 amp oldid 1175809184, wikipedia, wiki, book, books, library,
