L-AP4

Cat. No. 0103

L-AP4 C4H10NO5P [23052-81-5]

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Chemical Name: L-(+)-2-Amino-4-phosphonobutyric acid

Biological Activity

Selective group III metabotropic glutamate receptor agonist. Synaptic depressant. Agonist at the quisqualate-sensitized AP6 site in hippocampus. Also available as part of the Group III mGlu Receptor Tocriset™ and Mixed mGlu Receptor Tocriset™. DL Mixture (Cat. No. 0101) and D-isomer (Cat. No. 0102) also available.

Technical Data

M.Wt:
183.1
Formula:
C4H10NO5P
Solubility:
Soluble to 5 mM in water and to 100 mM in 1eq. NaOH
Purity:
>99 %
Storage:
Store at RT
CAS No:
23052-81-5

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
All Tocris products are intended for laboratory research use only.

Certificate of Analysis / Product Datasheet / Safety Data Sheet

Certificate of Analysis / Product Datasheet
Select another batch:

Bushell et al (1995) Antagonism of the synaptic depressant actions of L-AP4 in the lateral perforant path by MAP4. Neuropharmacology 34 239. PMID: 7617150.

Tones et al (1995) The agonist selectivity of a class III metabotropic glutamate receptor, human mGluR4a, is determined by the N-terminal extracellular domain. NeuroReport 7 117. PMID: 8742431.

Nakanishi (1992) Molecular diversity of glutamate receptors and implications for brain functions. Science 258 597. PMID: 1329206.

Evans et al (1982) The effect of a series of ω-phosphonic-α-carboxylic amino acids on electrically evoked and amino acid induced responses in isolated spinal cord preparations. Br.J.Pharmacol. 75 65. PMID: 7042024.

If you know of a relevant reference for this product please let us know.

Citations are publications that use Tocris products. Selected citations for L-AP4 include:

Prigge et al (2016) M1 ipRGCs Influence Visual Function through Retrograde Signaling in the Retina The Journal of Neuroscience 6 7184. PMID: 27383593.

Jacoby et al (2015) An Amacrine Cell Circuit for Signaling Steady Illumination in the Retina. Cell Rep 13 2663. PMID: 26711334.

Kammermeier (2015) Constitutive activity of metabotropic glutamate receptor 7. BMC Neurosci 16 17. PMID: 25881041.

Macé et al (2015) Targeting channelrhodopsin-2 to ON-bipolar cells with vitreally administered AAV Restores ON and OFF visual responses in blind mice. Mol Ther 23 7. PMID: 25095892.

Montesano et al (2015) Effects of the Concomitant Activation of ON and OFF Retinal Ganglion Cells on the Visual Thalamus: Evidence for an Enhanced Recruitment of GABAergic Cells. Front Neural Circuits 9 77. PMID: 26635537.

Murphy-Baum and Taylor (2015) The Synaptic and Morphological Basis of Orientation Selectivity in a Polyaxonal Amacrine Cell of the Rabbit Retina. J Neurosci 35 13336. PMID: 26424882.

Reifler et al (2015) The rat retina has five types of ganglion-cell photoreceptors. Exp Eye Res 130 17. PMID: 25450063.

Spampinato et al (2015) Glial metabotropic glutamate receptor-4 increases maturation and survival of oligodendrocytes. Front Cell Neurosci 8 462. PMID: 25642169.

Xiong et al (2015) Voriconazole, an antifungal triazol that causes visual side effects, is an inhibitor of TRPM1 and TRPM3 channels. Invest Ophthalmol Vis Sci 56 1367. PMID: 25650413.

Bennett et al (2014) Examination of VLC-PUFA-deficient photoreceptor terminals. Invest Ophthalmol Vis Sci 55 4063. PMID: 24764063.

Mills et al (2014) Three distinct blue-green color pathways in a mammalian retina. J Neurosci 34 1760. PMID: 24478358.

Tse et al (2014) Possible roles of glutamate transporter EAAT5 in mouse cone depolarizing bipolar cell light responses. Vision Res 103 63. PMID: 24972005.

Tse et al (2014) Pharmacological inhibitions of glutamate transporters EAAT1 and EAAT2 compromise glutamate transport in photoreceptor to ON-bipolar cell synapses. Vision Res 103 49. PMID: 25152321.

De-May and Ali (2013) Cell type-specific regulation of inhibition via cannabinoid type 1 receptors in rat neocortex. J Neurophysiol 109 216. PMID: 23054605.

Klatte et al (2013) Impaired D-serine-mediated cotransmission mediates cognitive dysfunction in epilepsy. J Neurosci 33 13066. PMID: 23926260.

Broadstock et al (2012) Antiparkinsonian potential of targeting group III metabotropic glutamate receptor subtypes in the rodent substantia nigra pars reticulata. Br J Pharmacol 165 1034. PMID: 21627638.

Caiati et al (2012) Developmental regulation of CB1-mediated spike-time dependent depression at immature mossy fiber-CA3 synapses. Sci Rep 2 285. PMID: 22368777.

Govea et al (2012) Group III metabotropic glutamate receptors and transient receptor potential vanilloid 1 co-localize and interact on nociceptors. Neuroscience 217 130. PMID: 22609935.

Hook et al (2012) Dopaminergic modulation of ganglion-cell photoreceptors in rat. Eur J Neurosci 35 507. PMID: 22304466.

Ichinose and Lukasiewicz (2012) The mode of retinal presynaptic inhibition switches with light intensity. J Neurosci 32 4360. PMID: 22457487.

Peachey et al (2012) Depolarizing bipolar cell dysfunction due to a Trpm1 point mutation. J Neurophysiol 108 2442. PMID: 22896717.

Sher and DeVries (2012) A non-canonical pathway for mammalian blue-green color vision. Nat Neurosci 15 952. PMID: 22634728.

Zhang et al (2012) Melanopsin mediates retrograde visual signaling in the retina. PLoS One 7 e42647. PMID: 22880066.

Pearring et al (2011) A role for nyctalopin, a small leucine-rich repeat protein, in localizing the TRP melastatin 1 channel to retinal depolarizing bipolar cell dendrites. J Neurosci 31 10060. PMID: 21734298.

Schmidt and Kofuji (2011) Structure and function of bistratified intrinsically photosensitive retinal ganglion cells in the mouse. J Comp Neurol 519 1492. PMID: 21452206.

Taman and Ribeiro (2011) Characterization of a truncated metabotropic glutamate receptor in a primitive metazoan, the parasitic flatworm Schistosoma mansoni. PLoS One 6 e27119. PMID: 22069494.

Maier et al (2010) Sustained glutamate receptor activation down-regulates GABAB receptors by shifting the balance from recycling to lysosomal degradation. J Biol Chem 285 35606. PMID: 20826795.

Maurer et al (2010) Distinct retinal deficits in a zebrafish pyruvate dehydrogenase-deficient mutant. J Neurosci 30 11962. PMID: 20826660.

Zhang et al (2010) RGS7 and -11 complexes accelerate the ON-bipolar cell light response. Invest Ophthalmol Vis Sci 51 1121. PMID: 19797214.

Krock et al (2009) Retrograde intraflagellar transport by cytoplasmic dynein-2 is required for outer segment extension in vertebrate photoreceptors but not arrestin translocation. Invest Ophthalmol Vis Sci 50 5463. PMID: 19474410.

Pickard et al (2009) Light-induced fos expression in intrinsically photosensitive retinal ganglion cells in melanopsin knockout (opn4) mice. PLoS One 4 e4984. PMID: 19319185.

Romo-Parra et al (2008) GABA actions in hippocampal area CA3 during postnatal development: differential shift from depolarizing to hyperpolarizing in somatic and dendritic compartments. J Neurophysiol 99 1523. PMID: 18216229.

Suh et al (2008) Corequirement of PICK1 binding and PKC phosphorylation for stable surface expression of the metabotropic glutamate receptor mGluR7. Neuron 58 736. PMID: 18549785.

Bender et al (2007) Localization of HCN1 channels to presynaptic compartments: novel plasticity that may contribute to hippocampal maturation. J Neurosci 27 4697. PMID: 17460082.

El-Kouhen et al (2006) Blockade of mGluR1 receptor results in analgesia and disruption of motor and cognitive performances: effects of A-841720, a novel non-competitive mGluR1 receptor antagonist. Br J Pharmacol 149 761. PMID: 17016515.

Galici et al (2006) Biphenyl-indanone A, a positive allosteric modulator of the metabotropic glutamate receptor subtype 2, has antipsychotic- and anxiolytic-like effects in mice. J Pharmacol Exp Ther 318 173. PMID: 16608916.

Matsui et al (2006) Effects of ethanol on photoreceptors and visual function in developing zebrafish. Invest Ophthalmol Vis Sci 47 4589. PMID: 17003456.

Newman (2005) Calcium increases in retinal glial cells evoked by light-induced neuronal activity. J Neurosci 25 5502. PMID: 15944378.

Sekaran et al (2005) Melanopsin-dependent photoreception provides earliest light detection in the mammalian retina. Curr Biol 15 1099. PMID: 15964274.

Fujino and Oertel (2003) Bidirectional synaptic plasticity in the cerebellum-like mammalian dorsal cochlear nucleus. Proc Natl Acad Sci U S A 100 265. PMID: 12486245.

Mathiesen et al (2003) Positive allosteric modulation of the human metabotropic glutamate receptor 4 (hmGluR4) by SIB-1893 and MPEP. Br J Pharmacol 138 1026. PMID: 12684257.

Nishi et al (2003) Metabotropic mGlu5 receptors regulate adenosine A2A receptor signaling. Proc Natl Acad Sci U S A 100 1322. PMID: 12538871.

Collard et al (2002) Neutrophil-derived glutamate regulates vascular endothelial barrier function. J Biol Chem 277 14801. PMID: 11847215.

Do you know of a great paper that uses L-AP4 from Tocris? If so please let us know.show all ▼show less ▲

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Keywords: L-AP4, supplier, Selective, group, III, mGlur, agonists, Group, Receptors, mGlu4, mGlu6, mGlu7, mGlu8, mGluR4, mGluR6, mGluR7, mGluR8, Glutamate, Metabotropic, Tocris Bioscience, Glutamate (Metabotropic) Group III Receptor Agonist products

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