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 / Safety Data Sheet

Certificate of Analysis: View current batch
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Safety Data Sheet: View Safety Data Sheet

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.

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.

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.

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.

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

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.

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.

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.

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.

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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