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23052-81-5,MFCD00083244
Catalog No.:AA00I4FT

23052-81-5 | L-Ap4

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1mg
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5mg
≥99%
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$139.00   $97.00
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10mg
≥99%
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50mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00I4FT
Chemical Name:
L-Ap4
CAS Number:
23052-81-5
Molecular Formula:
C4H10NO5P
Molecular Weight:
183.0997
MDL Number:
MFCD00083244
SMILES:
OC(=O)[C@H](CCP(=O)(O)O)N
Properties
Computed Properties
 
Complexity:
187  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
11  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
4  
XLogP3:
-5.5  

Literature

Title: Changes in the modulation of retinocollicular transmission through group III mGluRs long after an increase in intraocular pressure in a rat model of glaucoma.

Journal: Visual neuroscience 20120901

Title: Functional and pharmacological characteristics of metabotropic glutamate receptors 2/4 heterodimers.

Journal: Molecular pharmacology 20120901

Title: Gβ3 is required for normal light ON responses and synaptic maintenance.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20120815

Title: Α-amino-β-fluorocyclopropanecarboxylic acids as a new tool for drug development: synthesis of glutamic acid analogs and agonist activity towards metabotropic glutamate receptor 4.

Journal: Bioorganic & medicinal chemistry 20120801

Title: Behavioral responses to glutamate receptor agonists and antagonists implicate the involvement of brain-expressed mGluR4 and mGluR1 in taste transduction for umami in mice.

Journal: Physiology & behavior 20120201

Title: Modulation of glutamate release from parallel fibers by mGlu4 and pre-synaptic GABA(A) receptors.

Journal: Journal of neurochemistry 20120201

Title: mGluR6 transcripts in non-neuronal tissues.

Journal: The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society 20111201

Title: Light-evoked lateral GABAergic inhibition at single bipolar cell synaptic terminals is driven by distinct retinal microcircuits.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20111102

Title: Group III metabotropic glutamate receptors inhibit startle-mediating giant neurons in the caudal pontine reticular nucleus but do not mediate synaptic depression/short-term habituation of startle.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20100804

Title: Active roles of electrically coupled bipolar cell network in the adult retina.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20100707

Title: A virtual screening hit reveals new possibilities for developing group III metabotropic glutamate receptor agonists.

Journal: Journal of medicinal chemistry 20100408

Title: Parallel ON and OFF cone bipolar inputs establish spatially coextensive receptive field structure of blue-yellow ganglion cells in primate retina.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20090701

Title: A transient receptor potential-like channel mediates synaptic transmission in rod bipolar cells.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20090513

Title: Differential metabotropic glutamate receptor expression and modulation in two neocortical inhibitory networks.

Journal: Journal of neurophysiology 20090501

Title: Enhanced sensitivity to group II mGlu receptor activation at corticostriatal synapses in mice lacking the familial parkinsonism-linked genes PINK1 or Parkin.

Journal: Experimental neurology 20090201

Title: Design, synthesis and biological evaluation of novel bicyclo[1.1.1]pentane-based omega-acidic amino acids as glutamate receptors ligands.

Journal: Bioorganic & medicinal chemistry 20090101

Title: State-dependent cAMP sensitivity of presynaptic function underlies metaplasticity in a hippocampal feedforward inhibitory circuit.

Journal: Neuron 20081226

Title: The inhibition of release by mGlu7 receptors is independent of the Ca2+ channel type but associated to GABAB and adenosine A1 receptors.

Journal: Neuropharmacology 20080901

Title: AMN082, an allosteric mGluR7 agonist that inhibits afferent glutamatergic transmission in rat basolateral amygdala.

Journal: Neuropharmacology 20080901

Title: Conformational change of the transmembrane helices II and IV of metabotropic glutamate receptor involved in G protein activation.

Journal: Journal of neurochemistry 20080701

Title: Evaluation of the amino acid binding site of Mycobacterium tuberculosis glutamine synthetase for drug discovery.

Journal: Bioorganic & medicinal chemistry 20080515

Title: Group III metabotropic glutamate receptors act as hetero-receptors modulating evoked GABA release in the globus pallidus in vivo.

Journal: European journal of pharmacology 20080202

Title: mGlu4 potentiation of K(2P)2.1 is dependant on C-terminal dephosphorylation.

Journal: Molecular and cellular neurosciences 20080101

Title: L-(+)-2-Amino-4-thiophosphonobutyric acid (L-thioAP4), a new potent agonist of group III metabotropic glutamate receptors: increased distal acidity affords enhanced potency.

Journal: Journal of medicinal chemistry 20070920

Title: Synthesis and biological evaluation of 1-amino-2-phosphonomethylcyclopropanecarboxylic acids, new group III metabotropic glutamate receptor agonists.

Journal: Journal of medicinal chemistry 20070726

Title: Glutamatergic input is coded by spike frequency at the soma and proximal dendrite of AII amacrine cells in the mouse retina.

Journal: The European journal of neuroscience 20070601

Title: Synthesis and preliminary pharmacological evaluation of the four stereoisomers of (2S)-2-(2'-phosphono-3'-phenylcyclopropyl)glycine, the first class of 3'-substituted trans C1'-2'-2-(2'-phosphonocyclopropyl)glycines.

Journal: Bioorganic & medicinal chemistry 20070501

Title: Compartmentalized Ca(2+) channel regulation at divergent mossy-fiber release sites underlies target cell-dependent plasticity.

Journal: Neuron 20061109

Title: Activation of Group II/III metabotropic glutamate receptors attenuates LPS-induced astroglial neurotoxicity via promoting glutamate uptake.

Journal: Journal of neuroscience research 20060801

Title: High-density presynaptic transporters are required for glutamate removal from the first visual synapse.

Journal: Neuron 20060406

Title: Synthesis and preliminary biological evaluation of (2S,1'R,2'S)- and (2S,1'S,2'R)-2-(2'-phosphonocyclopropyl)glycines, two novel conformationally constrained l-AP4 analogues.

Journal: Bioorganic & medicinal chemistry letters 20060101

Title: Effects of baclofen and L-AP4 in passive avoidance test in rats after hypoxia-induced amnesia.

Journal: Pharmacological reports : PR 20060101

Title: G protein coupling profile of mGluR6 and expression of G alpha proteins in retinal ON bipolar cells.

Journal: Visual neuroscience 20060101

Title: Retinal bipolar cell input mechanisms in giant danio. III. ON-OFF bipolar cells and their color-opponent mechanisms.

Journal: Journal of neurophysiology 20050701

Title: Coupling of metabotropic glutamate receptor 8 to N-type Ca2+ channels in rat sympathetic neurons.

Journal: Molecular pharmacology 20050601

Title: Group III metabotropic glutamate receptors and exocytosed protons inhibit L-type calcium currents in cones but not in rods.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20050420

Title: The photopic ERG of the albino guinea pig (Cavia porcellus): a model of the human photopic ERG.

Journal: Documenta ophthalmologica. Advances in ophthalmology 20050101

Title: Abnormal metabotropic glutamate receptor expression and signaling in the cerebral cortex in diffuse Lewy body disease is associated with irregular alpha-synuclein/phospholipase C (PLCbeta1) interactions.

Journal: Brain pathology (Zurich, Switzerland) 20041001

Title: Depression of GABAergic input to identified hippocampal neurons by group III metabotropic glutamate receptors in the rat.

Journal: The European journal of neuroscience 20040501

Title: Role of the group III metabotropic glutamate receptor in LTP, depotentiation and LTD in dentate gyrus of freely moving rats.

Journal: Neuropharmacology 20040201

Title: (2S,1'S,2'R,3'R)-2-(2'-Carboxy-3'-hydroxymethylcyclopropyl) glycine is a highly potent group 2 and 3 metabotropic glutamate receptor agonist with oral activity.

Journal: Journal of medicinal chemistry 20040115

Title: The human D2 dopamine receptor synergizes with the A2A adenosine receptor to stimulate adenylyl cyclase in PC12 cells.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20030701

Title: Simultaneous analysis of biologically active aminoalkanephosphonic acids.

Journal: Journal of chromatography. A 20030523

Title: Reduction of excitatory postsynaptic responses by persistently active metabotropic glutamate receptors in the hippocampus.

Journal: Journal of neurophysiology 20030401

Title: The role of electrostatic interaction in the molecular recognition of selective agonists to metabotropic glutamate receptors.

Journal: Proteins 20030301

Title: Synergistic responses of the chorda tympani to mixtures of umami and sweet substances in rats.

Journal: Chemical senses 20030301

Title: Group III metabotropic glutamate receptors as autoreceptors in the cerebellar cortex.

Journal: British journal of pharmacology 20030201

Title: Activation of group III metabotropic glutamate receptors presynaptically reduces both GABAergic and glutamatergic transmission in the rat globus pallidus.

Journal: Neuroscience 20030101

Title: Activation of glutamate transporters in rods inhibits presynaptic calcium currents.

Journal: Visual neuroscience 20030101

Title: Common and selective molecular determinants involved in metabotopic glutamate receptor agonist activity.

Journal: Journal of medicinal chemistry 20020718

Title: Neuroprotective effects of N-acetylaspartylglutamate in a neonatal rat model of hypoxia-ischemia.

Journal: European journal of pharmacology 20020222

Title: Glutamate uptake inhibition modulates dorsal horn neurotransmission: a comparison between normal and arthritic rats.

Journal: Neuroreport 20011221

Title: Modulation of primary afferent-mediated neurotransmission and Fos expression by glutamate uptake inhibition in rat spinal neurones in vitro.

Journal: Neuropharmacology 20011001

Title: Cyclic AMP-dependent protein kinase phosphorylates group III metabotropic glutamate receptors and inhibits their function as presynaptic receptors.

Journal: Journal of neurochemistry 20010801

Title: Priming stimulation of group II metabotropic glutamate receptors inhibits the subsequent induction of rat hippocampal long-term depression in vitro.

Journal: Neuroscience letters 20010706

Title: Frequency dependence of endocytosis in aortic baroreceptor neurons and role of group III mGluRs.

Journal: American journal of physiology. Heart and circulatory physiology 20010701

Title: Inhibition of choline acetyltransferase by excitatory amino acids as a possible mechanism for cholinergic dysfunction in the central nervous system.

Journal: Journal of neurochemistry 20010501

Title: Behavioral taste similarities and differences among monosodium L-glutamate and glutamate receptor agonists in C57BL mice.

Journal: Journal of nutritional science and vitaminology 20010401

Title: (S)-3,4-DCPG, a potent and selective mGlu8a receptor agonist, activates metabotropic glutamate receptors on primary afferent terminals in the neonatal rat spinal cord.

Journal: Neuropharmacology 20010301

Title: An in vivo eyecup preparation for the rat.

Journal: Journal of neuroscience methods 20010215

Title: Pharmacological profiles of the metabotropic glutamate receptor ligands.

Journal: Neuropharmacology 20010101

Title: cAMP-dependent presynaptic regulation of spontaneous glycinergic IPSCs in mechanically dissociated rat spinal cord neurons.

Journal: Journal of neurophysiology 20010101

Title: Binding of [3H](2S,1'S,2'S)-2-(9-xanthylmethyl)-2-(2'-carboxycyclopropyl) glycine ([3H]LY341495) to cell membranes expressing recombinant human group III metabotropic glutamate receptor subtypes.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20001201

Title: Effect of the umami peptides on the ligand binding and function of rat mGlu4a receptor might implicate this receptor in the monosodium glutamate taste transduction.

Journal: British journal of pharmacology 19991101

Title: Cloning and functional expression of alternative spliced variants of the human metabotropic glutamate receptor 8.

Journal: Brain research. Molecular brain research 19990420

Title: Ligand binding to the amino-terminal domain of the mGluR4 subtype of metabotropic glutamate receptor.

Journal: The Journal of biological chemistry 19990409

Title: Group III human metabotropic glutamate receptors 4, 7 and 8: molecular cloning, functional expression, and comparison of pharmacological properties in RGT cells.

Journal: Brain research. Molecular brain research 19980101

Title: (S)-homo-AMPA, a specific agonist at the mGlu6 subtype of metabotropic glutamic acid receptors.

Journal: Journal of medicinal chemistry 19971024

Title: Cloning, distribution and functional expression of the human mGlu6 metabotropic glutamate receptor.

Journal: Neuropharmacology 19970201

Title: Cloning and expression of rat metabotropic glutamate receptor 8 reveals a distinct pharmacological profile.

Journal: Molecular pharmacology 19970101

Title: Cloning and characterization of a metabotropic glutamate receptor, mGluR4b.

Journal: Neuropharmacology 19970101

Title: [3H]-L-2-amino-4-phosphonobutyrate labels a metabotropic glutamate receptor, mGluR4a.

Journal: British journal of pharmacology 19951201

Title: Signal transduction, pharmacological properties, and expression patterns of two rat metabotropic glutamate receptors, mGluR3 and mGluR4.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 19930401

Title: Selvam C, et al. Increased Potency and Selectivity for Group III Metabotropic Glutamate Receptor Agonists Binding at Dual sites. J Med Chem. 2018 Mar 8;61(5):1969-1989.

Title: Chen SR, et al. Distinct roles of group III metabotropic glutamate receptors in control of nociception and dorsal horn neurons in normal and nerve-injured Rats. J Pharmacol Exp Ther. 2005 Jan;312(1):120-6.

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Tags:23052-81-5 Molecular Formula|23052-81-5 MDL|23052-81-5 SMILES|23052-81-5 L-Ap4