L-AP4

Pricing Availability Delivery Time Qty
Cat.No. 0103 - L-AP4 | C4H10NO5P | CAS No. 23052-81-5
Description: Selective group III mGlu agonist
Chemical Name: L-(+)-2-Amino-4-phosphonobutyric acid
Purity: ≥99% (HPLC)
Datasheet
Citations (43)
Literature

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
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.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
1eq. NaOH 18.31 100
water 0.92 5

Preparing Stock Solutions

The following data is based on the product molecular weight 183.1. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
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

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

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


If you know of a relevant reference for L-AP4, please let us know.

View Related Products by Product Action

View all Glutamate (Metabotropic) Group III Receptor Agonists

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43 Citations for L-AP4

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

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) 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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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


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

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