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Submit ReviewL-AP4
Description: Selective group III mGlu agonist
Chemical Name: L-(+)-2-Amino-4-phosphonobutyric acid
Purity: ≥99% (HPLC)
Biological Activity for L-AP4
L-AP4 is a selective group III metabotropic glutamate receptor agonist that acts at mGlu4, mGlu8, mGlu6 and mGlu7 receptors (EC50 values = 0.1-0.13 μM, 0.29 μM, 1.0-2.4 μM and 249-337 μM, respectively). L-AP4 is a synaptic depressant and inhibits excitatory post-synaptic currents. L-AP4 is also an agonist at the quisqualate-sensitized AP6 site in hippocampus.
DL Mixture and D-isomer also available.
Technical Data for L-AP4
| M. Wt | 183.1 |
| Formula | C4H10NO5P |
| Storage | Store at RT |
| Purity | ≥99% (HPLC) |
| CAS Number | 23052-81-5 |
| PubChem ID | 179394 |
| InChI Key | DDOQBQRIEWHWBT-VKHMYHEASA-N |
| Smiles | [H][C@@](CCP(O)(O)=O)(N)C(O)=O |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for L-AP4
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| water | 0.92 | 5 | |
| 1eq. NaOH | 18.31 | 100 |
Preparing Stock Solutions for L-AP4
The following data is based on the product molecular weight 183.1. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 5.46 mL | 27.31 mL | 54.61 mL |
| 5 mM | 1.09 mL | 5.46 mL | 10.92 mL |
| 10 mM | 0.55 mL | 2.73 mL | 5.46 mL |
| 50 mM | 0.11 mL | 0.55 mL | 1.09 mL |
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Product Datasheets for L-AP4
References for L-AP4
References are publications that support the biological activity of the product.
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
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
Nakanishi (1992) Molecular diversity of glutamate receptors and implications for brain functions. Science 258 597 PMID: 1329206
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
Selvam et al (2018) Increased potency and selectivity for group III metabotropic glutamate receptor agonists binding at dual sites. J.Med.Chem. 61 1969 PMID: 29397723
If you know of a relevant reference for L-AP4, please let us know.
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Keywords: L-AP4, L-AP4 supplier, Selective, group, III, mGlur, agonists, Group, Receptors, mGlu4, mGlu6, mGlu7, mGlu8, mGluR4, mGluR6, mGluR7, mGluR8, Glutamate, Metabotropic, (Metabotropic), 0103, Tocris Bioscience
56 Citations for L-AP4
Citations are publications that use Tocris products. Selected citations for L-AP4 include:
Hellmer et al (2018) A group I metabotropic glutamate receptor controls synaptic gain between rods and rod bipolar cells in the mouse retina. Physiol Rep 6 e13885 PMID: 30338673
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
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
Chaffiol et al (2017) A New Promoter Allows Optogenetic Vision Restoration with Enhanced Sensitivity in Macaque Retina. Mol Ther 25 2546 PMID: 28807567
Mills et al (2014) Three distinct blue-green color pathways in a mammalian retina. J Neurosci 34 1760 PMID: 24478358
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
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
Sabater et al (2021) Voltage-gated potassium channels ensure action potential shape fidelity in distal axons. J Neurosci 41 5372 PMID: 34001627
Maldonado et al (2021) Oxytocin shapes spontaneous activity patterns in the developing visual cortex by activating somatostatin interneurons. Curr Biol 31 322 PMID: 33157028
Scholler (2017) HTS-compatible FRET-based conformational sensors clarify membrane receptor activation. Nat Chem Biol 13 372 PMID: 28135236
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
Kammermeier (2015) Constitutive activity of metabotropic glutamate receptor 7. BMC Neurosci 16 17 PMID: 25881041
Schmidt and Kofuji (2011) Structure and function of bistratified intrinsically photosensitive retinal ganglion cells in the mouse. J Comp Neurol 519 1492 PMID: 21452206
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
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
Reifler et al (2015) The rat retina has five types of ganglion-cell photoreceptors. Exp Eye Res 130 17 PMID: 25450063
Jacoby et al (2015) An Amacrine Cell Circuit for Signaling Steady Illumination in the Retina. Cell Rep 13 2663 PMID: 26711334
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
Spampinato et al (2015) Glial metabotropic glutamate receptor-4 increases maturation and survival of oligodendrocytes. Front Cell Neurosci 8 462 PMID: 25642169
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
Bennett et al (2014) Examination of VLC-PUFA-deficient photoreceptor terminals. Invest Ophthalmol Vis Sci 55 4063 PMID: 24764063
Kiyama et al (2019) Essential Roles of Tbr1 in the Formation and Maintenance of the Orientation-Selective J-RGCs and a Group of OFF-Sustained RGCs in Mouse. Cell Rep 27 900 PMID: 30995485
Caiati et al (2013) PrPC controls via protein kinase A the direction of synaptic plasticity in the immature hippocampus. J Neurosci 33 2973 PMID: 23407955
Ichinose and Lukasiewicz (2012) The mode of retinal presynaptic inhibition switches with light intensity. J Neurosci 32 4360 PMID: 22457487
Bonezzi et al (2018) The Development of Mid-Wavelength Photoresponsivity in the Mouse Retina. Curr Eye Res 43 666 PMID: 29447486
Manookin et al (2018) Neural Mechanisms Mediating Motion Sensitivity in Parasol Ganglion Cells of the Primate Retina. Neuron 97 1327 PMID: 29503188
Lee et al (2022) Inhibition, but not excitation, recovers from partial cone loss with greater spatiotemporal integration, synapse density, and frequency. Cell Rep. 38 110317 PMID: 35108533
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
Sher and DeVries (2012) A non-canonical pathway for mammalian blue-green color vision. Nat Neurosci 15 952 PMID: 22634728
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
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
Prigge et al (2016) M1 ipRGCs Influence Visual Function through Retrograde Signaling in the Retina The Journal of Neuroscience 6 7184 PMID: 27383593
Zhang et al (2012) Melanopsin mediates retrograde visual signaling in the retina. PLoS One 7 e42647 PMID: 22880066
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
Peachey et al (2012) Depolarizing bipolar cell dysfunction due to a Trpm1 point mutation. J Neurophysiol 108 2442 PMID: 22896717
Hook et al (2012) DArgic modulation of ganglion-cell photoreceptors in rat. Eur J Neurosci 35 507 PMID: 22304466
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
Zhang et al (2010) RGS7 and -11 complexes accelerate the ON-bipolar cell light response. Invest Ophthalmol Vis Sci 51 1121 PMID: 19797214
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
Maruyama et al (2006) Umami responses in mouse taste cells indicate more than one receptor. J Neurosci 26 2227 PMID: 16495449
Alberdi et al (2006) Activation of kainate receptors sensitizes oligodendrocytes to complement attack. J Neurosci 26 3220 PMID: 16554473
Jiang et al (2006) Activation of group III metabotropic glutamate receptors attenuates rotenone toxicity on DArgic neurons through a microtubule-dependent mechanism. J Neurosci 26 4318 PMID: 16624952
Newman (2005) Calcium increases in retinal glial cells evoked by light-induced neuronal activity. J Neurosci 25 5502 PMID: 15944378
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
Matsui et al (2006) Effects of ethanol on photoreceptors and visual function in developing zebrafish. Invest Ophthalmol Vis Sci 47 4589 PMID: 17003456
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
Sekaran et al (2005) Melanopsin-dependent photoreception provides earliest light detection in the mammalian retina. Curr Biol 15 1099 PMID: 15964274
Do you know of a great paper that uses L-AP4 from Tocris? Please let us know.
Reviews for L-AP4
Average Rating: 5 (Based on 1 Review.)
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Used in inhibitor cocktail.
By
Anonymous on 12/03/2019
Assay Type: In Vitro
Species: Rat
Cell Line/Tissue: Retinal rod bipolar cells
Retinal dissections were performed in HEPES-buffered extracellular solution containing inhibitor cocktail4 umol/L
Literature in this Area
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*Please note that Tocris will only send literature to established scientific business / institute addresses.
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