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PMPA(NAALADaseinhibitor)

CAS No.:
173039-10-6
Catalog Number:
AG00AKR8
Molecular Formula:
C6H11O7P
Molecular Weight:
226.1211
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥95%
1 week
United States
$91
- +
5mg
98%
1 week
United States
$154
- +
10mg
98%
1 week
United States
$210
- +
25mg
98%
1 week
United States
$362
- +
50mg
98%
1 week
United States
$501
- +
100mg
98%
1 week
United States
$779
- +
Product Description
Catalog Number:
AG00AKR8
Chemical Name:
PMPA(NAALADaseinhibitor)
CAS Number:
173039-10-6
Molecular Formula:
C6H11O7P
Molecular Weight:
226.1211
MDL Number:
MFCD00940167
IUPAC Name:
2-(phosphonomethyl)pentanedioic acid
InChI:
InChI=1S/C6H11O7P/c7-5(8)2-1-4(6(9)10)3-14(11,12)13/h4H,1-3H2,(H,7,8)(H,9,10)(H2,11,12,13)
InChI Key:
ISEYJGQFXSTPMQ-UHFFFAOYSA-N
SMILES:
OC(=O)CCC(C(=O)O)CP(=O)(O)O
Properties
Complexity:
267  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
226.024g/mol
Formal Charge:
0
Heavy Atom Count:
14  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
226.121g/mol
Monoisotopic Mass:
226.024g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
132A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0
XLogP3:
-2.2  
Literature
Title Journal
NAAG peptidase inhibitors block cognitive deficit induced by MK-801 and motor activation induced by d-amphetamine in animal models of schizophrenia. Translational psychiatry 20120701
Effects of N-acetylaspartylglutamate (NAAG) peptidase inhibition on release of glutamate and dopamine in prefrontal cortex and nucleus accumbens in phencyclidine model of schizophrenia. The Journal of biological chemistry 20120622
Glutamate carboxypeptidase II (GCPII) inhibitor displays anti-glutamate and anti-cocaine effects in an invertebrate assay. Amino acids 20120601
mGluR3 and not mGluR2 receptors mediate the efficacy of NAAG peptidase inhibitor in validated model of schizophrenia. Schizophrenia research 20120401
Group II mGluR agonist LY354740 and NAAG peptidase inhibitor effects on prepulse inhibition in PCP and D-amphetamine models of schizophrenia. Psychopharmacology 20110701
Glutamate carboxypeptidase activity in human skin biopsies as a pharmacodynamic marker for clinical studies. Journal of translational medicine 20110101
Glutamate carboxypeptidase II: an amyloid peptide-degrading enzyme with physiological function in the brain. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20101101
Expression of prostate-specific membrane antigen (PSMA), increases cell folate uptake and proliferation and suggests a novel role for PSMA in the uptake of the non-polyglutamated folate, folic acid. The Prostate 20100215
Oral administration of the NAALADase inhibitor GPI-5693 attenuates cocaine-induced reinstatement of drug-seeking behavior in rats. European journal of pharmacology 20100210
N-acetylaspartylglutamate (NAAG) inhibits intravenous cocaine self-administration and cocaine-enhanced brain-stimulation reward in rats. Neuropharmacology 20100101
Inhibition of NAALADase by 2-PMPA attenuates cocaine-induced relapse in rats: a NAAG-mGluR2/3-mediated mechanism. Journal of neurochemistry 20100101
GCP II inhibition rescues neurons from gp120IIIB-induced neurotoxicity. Journal of neurovirology 20090901
Multivalent scaffolds for affinity maturation of small molecule cell surface binders and their application to prostate tumor targeting. Journal of medicinal chemistry 20090122
Effects of selective inhibition of N-acetylated-alpha-linked-acidic dipeptidase (NAALADase) on mice in learning and memory tasks. European journal of pharmacology 20080128
Intracerebroventricular administration of N-acetylaspartylglutamate (NAAG) peptidase inhibitors is analgesic in inflammatory pain. Molecular pain 20080101
Progress in the discovery and development of glutamate carboxypeptidase II inhibitors. Drug discovery today 20070901
Structural insight into the pharmacophore pocket of human glutamate carboxypeptidase II. Journal of medicinal chemistry 20070712
Human glutamate carboxypeptidase II inhibition: structures of GCPII in complex with two potent inhibitors, quisqualate and 2-PMPA. Acta crystallographica. Section D, Biological crystallography 20070401
Design, synthesis and pharmacological activity of novel enantiomerically pure phosphonic acid-based NAALADase inhibitors. Organic & biomolecular chemistry 20070307
Endogenous N-acetylaspartylglutamate reduced NMDA receptor-dependent current neurotransmission in the CA1 area of the hippocampus. Journal of neurochemistry 20070101
Local administration of N-acetylaspartylglutamate (NAAG) peptidase inhibitors is analgesic in peripheral pain in rats. The European journal of neuroscience 20070101
Effects of NAAG peptidase inhibitor 2-PMPA in model chronic pain - relation to brain concentration. Neuropharmacology 20061201
Unique presynaptic and postsynaptic roles of Group II metabotropic glutamate receptors in the modulation of thalamic network activity. Neuroscience 20060811
Prostate specific membrane antigen (PSMA) expression gives prostate cancer cells a growth advantage in a physiologically relevant folate environment in vitro. The Prostate 20060601
Complex character analysis of heart rate variability following brain asphyxia. Medical engineering & physics 20060501
2-phosphonomethyl-pentanedioic acid (glutamate carboxypeptidase II inhibitor) increases threshold for electroconvulsions and enhances the antiseizure action of valproate against maximal electroshock-induced seizures in mice. European journal of pharmacology 20060215
Glutamate carboxypeptidase II (NAALADase) inhibition as a novel therapeutic strategy. Advances in experimental medicine and biology 20060101
2-MPPA, a selective glutamate carboxypeptidase II inhibitor, attenuates morphine tolerance but not dependence in C57/Bl mice. Psychopharmacology 20051201
Effect of N-acetylaspartylglutamate (NAAG) on non-quantal and spontaneous quantal release of acetylcholine at the neuromuscular synapse of rat. Journal of neurochemistry 20050701
Regulation of glutamate carboxypeptidase II hydrolysis of N-acetylaspartylglutamate (NAAG) in crayfish nervous tissue is mediated by glial glutamate and acetylcholine receptors. Journal of neurochemistry 20050501
Enantiospecificity of glutamate carboxypeptidase II inhibition. Journal of medicinal chemistry 20050407
Inhibition of glutamate carboxypeptidase II (NAALADase) protects against dynorphin A-induced ischemic spinal cord injury in rats. European journal of pharmacology 20050131
2-PMPA, a NAAG peptidase inhibitor, attenuates magnetic resonance BOLD signals in brain of anesthetized mice: evidence of a link between neuron NAAG release and hyperemia. Journal of molecular neuroscience : MN 20050101
N-Acetylated alpha-linked acidic dipeptidase expressed in rat adipocytes is localized in the insulin-responsive glucose transporter (GLUT4) intracellular compartments and involved in the insulin-stimulated GLUT4 recruitment. Archives of biochemistry and biophysics 20040401
Protection against glucose-induced neuronal death by NAAG and GCP II inhibition is regulated by mGluR3. Journal of neurochemistry 20040401
Synthesis of urea-based inhibitors as active site probes of glutamate carboxypeptidase II: efficacy as analgesic agents. Journal of medicinal chemistry 20040325
Effects of GCP-II inhibition on responses of dorsal horn neurones after inflammation and neuropathy: an electrophysiological study in the rat. Neuropeptides 20031001
Synthesis and biological evaluation of hydroxamate-Based inhibitors of glutamate carboxypeptidase II. Bioorganic & medicinal chemistry letters 20030707
NAALADase inhibition protects motor neurons against chronic glutamate toxicity. European journal of pharmacology 20030627
Synthesis and biological evaluation of thiol-based inhibitors of glutamate carboxypeptidase II: discovery of an orally active GCP II inhibitor. Journal of medicinal chemistry 20030508
Morphine tolerance and reward but not expression of morphine dependence are inhibited by the selective glutamate carboxypeptidase II (GCP II, NAALADase) inhibitor, 2-PMPA. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20030301
Glutamate carboxypeptidase II inhibition as a novel therapeutic target. Advances in experimental medicine and biology 20030101
Kinetics and inhibition of glutamate carboxypeptidase II using a microplate assay. Analytical biochemistry 20021101
Deletion of the glutamate carboxypeptidase II gene in mice reveals a second enzyme activity that hydrolyzes N-acetylaspartylglutamate. Journal of neurochemistry 20021001
Molecular modeling of the interactions of glutamate carboxypeptidase II with its potent NAAG-based inhibitors. Journal of medicinal chemistry 20020912
NAALADase (GCP II) inhibition prevents cocaine-kindled seizures. Neuropharmacology 20020901
Neuroprotective effects of N-acetylaspartylglutamate in a neonatal rat model of hypoxia-ischemia. European journal of pharmacology 20020222
Effect of 2-(phosphono-methyl)-pentanedioic acid on allodynia and afferent ectopic discharges in a rat model of neuropathic pain. The Journal of pharmacology and experimental therapeutics 20020201
11C-MCG: synthesis, uptake selectivity, and primate PET of a probe for glutamate carboxypeptidase II (NAALADase). Molecular imaging 20020101
Neuroprotection mediated by glutamate carboxypeptidase II (NAALADase) inhibition requires TGF-beta. European journal of pharmacology 20011026
Binding of the glutamate carboxypeptidase II (NAALADase) inhibitor 2-PMPA to rat brain membranes. European journal of pharmacology 20010914
Neuroprotection afforded by NAAG and NAALADase inhibition requires glial cells and metabotropic glutamate receptor activation. European journal of pharmacology 20010824
Spinal N-acetyl-alpha-linked acidic dipeptidase (NAALADase) inhibition attenuates mechanical allodynia induced by paw carrageenan injection in the rat. Brain research 20010803
Expression and acquisition of the conditioned place preference response to cocaine in rats is blocked by selective inhibitors of the enzyme N-acetylated-alpha-linked-acidic dipeptidase (NAALADASE). Synapse (New York, N.Y.) 20010701
Design of remarkably simple, yet potent urea-based inhibitors of glutamate carboxypeptidase II (NAALADase). Journal of medicinal chemistry 20010201
Inhibition of spinal N-acetylated-alpha-linked acidic dipeptidase produces an antinociceptive effect in the rat formalin test. Neuroscience 20010101
N-acetylaspartylglutamate (NAAG) is the probable mediator of axon-to-glia signaling in the crayfish medial giant nerve fiber. Neuroscience 20010101
Mechanisms for clearance of released N-acetylaspartylglutamate in crayfish nerve fibers: implications for axon-glia signaling. Neuroscience 20010101
Properties