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173039-10-6,MFCD00940167
Catalog No.:AA00AKOG

173039-10-6 | PMPA(NAALADaseinhibitor)

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1mg
≥95%
in stock  
$46.00   $32.00
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5mg
≥95%
in stock  
$143.00   $100.00
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10mg
≥95%
in stock  
$199.00   $139.00
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25mg
≥95%
in stock  
$436.00   $305.00
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50mg
98% (HPLC)
in stock  
$679.00   $475.00
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100mg
98% (HPLC)
in stock  
$1,068.00   $748.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00AKOG
Chemical Name:
PMPA(NAALADaseinhibitor)
CAS Number:
173039-10-6
Molecular Formula:
C6H11O7P
Molecular Weight:
226.1211
MDL Number:
MFCD00940167
SMILES:
OC(=O)CCC(C(=O)O)CP(=O)(O)O
Properties
Properties
 
BP:
538.79°C at 760 mmHg  
Form:
Solid  
Storage:
Keep in dry area;Room Temperature;  

Computed Properties
 
Complexity:
267  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
14  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
6  
Undefined Atom Stereocenter Count:
1  
XLogP3:
-2.2  

Downstream Synthesis Route
CASUnavailable 
  173039-10-6 

[1]Jackson,PaulF.;Cole,DerekC.;Slusher,BarbaraS.;Stetz,SusanL.;Ross,LaurieE.;etal.[JournalofMedicinalChemistry,1996,vol.39,#2,p.619-622]

[1]CurrentPatentAssignee:UNIVERSITYOFMICHIGAN-WO2008/8483,2008,A2Locationinpatent:Page/Pagecolumn103

[1]Jackson,PaulF.;Cole,DerekC.;Slusher,BarbaraS.;Stetz,SusanL.;Ross,LaurieE.;etal.[JournalofMedicinalChemistry,1996,vol.39,#2,p.619-622]

[1]CurrentPatentAssignee:EISAICOLTD-US6384022,2002,B1

[2]CurrentPatentAssignee:EISAICOLTD-US5977090,1999,A

[3]CurrentPatentAssignee:EISAICOLTD-US6017903,2000,A

Literature

Title: NAAG peptidase inhibitors block cognitive deficit induced by MK-801 and motor activation induced by d-amphetamine in animal models of schizophrenia.

Journal: Translational psychiatry 20120701

Title: Effects of N-acetylaspartylglutamate (NAAG) peptidase inhibition on release of glutamate and dopamine in prefrontal cortex and nucleus accumbens in phencyclidine model of schizophrenia.

Journal: The Journal of biological chemistry 20120622

Title: Glutamate carboxypeptidase II (GCPII) inhibitor displays anti-glutamate and anti-cocaine effects in an invertebrate assay.

Journal: Amino acids 20120601

Title: mGluR3 and not mGluR2 receptors mediate the efficacy of NAAG peptidase inhibitor in validated model of schizophrenia.

Journal: Schizophrenia research 20120401

Title: Group II mGluR agonist LY354740 and NAAG peptidase inhibitor effects on prepulse inhibition in PCP and D-amphetamine models of schizophrenia.

Journal: Psychopharmacology 20110701

Title: Glutamate carboxypeptidase activity in human skin biopsies as a pharmacodynamic marker for clinical studies.

Journal: Journal of translational medicine 20110101

Title: Glutamate carboxypeptidase II: an amyloid peptide-degrading enzyme with physiological function in the brain.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20101101

Title: 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.

Journal: The Prostate 20100215

Title: Oral administration of the NAALADase inhibitor GPI-5693 attenuates cocaine-induced reinstatement of drug-seeking behavior in rats.

Journal: European journal of pharmacology 20100210

Title: N-acetylaspartylglutamate (NAAG) inhibits intravenous cocaine self-administration and cocaine-enhanced brain-stimulation reward in rats.

Journal: Neuropharmacology 20100101

Title: Inhibition of NAALADase by 2-PMPA attenuates cocaine-induced relapse in rats: a NAAG-mGluR2/3-mediated mechanism.

Journal: Journal of neurochemistry 20100101

Title: GCP II inhibition rescues neurons from gp120IIIB-induced neurotoxicity.

Journal: Journal of neurovirology 20090901

Title: Multivalent scaffolds for affinity maturation of small molecule cell surface binders and their application to prostate tumor targeting.

Journal: Journal of medicinal chemistry 20090122

Title: Effects of selective inhibition of N-acetylated-alpha-linked-acidic dipeptidase (NAALADase) on mice in learning and memory tasks.

Journal: European journal of pharmacology 20080128

Title: Intracerebroventricular administration of N-acetylaspartylglutamate (NAAG) peptidase inhibitors is analgesic in inflammatory pain.

Journal: Molecular pain 20080101

Title: Progress in the discovery and development of glutamate carboxypeptidase II inhibitors.

Journal: Drug discovery today 20070901

Title: Structural insight into the pharmacophore pocket of human glutamate carboxypeptidase II.

Journal: Journal of medicinal chemistry 20070712

Title: Human glutamate carboxypeptidase II inhibition: structures of GCPII in complex with two potent inhibitors, quisqualate and 2-PMPA.

Journal: Acta crystallographica. Section D, Biological crystallography 20070401

Title: Design, synthesis and pharmacological activity of novel enantiomerically pure phosphonic acid-based NAALADase inhibitors.

Journal: Organic & biomolecular chemistry 20070307

Title: Endogenous N-acetylaspartylglutamate reduced NMDA receptor-dependent current neurotransmission in the CA1 area of the hippocampus.

Journal: Journal of neurochemistry 20070101

Title: Local administration of N-acetylaspartylglutamate (NAAG) peptidase inhibitors is analgesic in peripheral pain in rats.

Journal: The European journal of neuroscience 20070101

Title: Effects of NAAG peptidase inhibitor 2-PMPA in model chronic pain - relation to brain concentration.

Journal: Neuropharmacology 20061201

Title: Unique presynaptic and postsynaptic roles of Group II metabotropic glutamate receptors in the modulation of thalamic network activity.

Journal: Neuroscience 20060811

Title: Prostate specific membrane antigen (PSMA) expression gives prostate cancer cells a growth advantage in a physiologically relevant folate environment in vitro.

Journal: The Prostate 20060601

Title: Complex character analysis of heart rate variability following brain asphyxia.

Journal: Medical engineering & physics 20060501

Title: 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.

Journal: European journal of pharmacology 20060215

Title: Glutamate carboxypeptidase II (NAALADase) inhibition as a novel therapeutic strategy.

Journal: Advances in experimental medicine and biology 20060101

Title: 2-MPPA, a selective glutamate carboxypeptidase II inhibitor, attenuates morphine tolerance but not dependence in C57/Bl mice.

Journal: Psychopharmacology 20051201

Title: Effect of N-acetylaspartylglutamate (NAAG) on non-quantal and spontaneous quantal release of acetylcholine at the neuromuscular synapse of rat.

Journal: Journal of neurochemistry 20050701

Title: Regulation of glutamate carboxypeptidase II hydrolysis of N-acetylaspartylglutamate (NAAG) in crayfish nervous tissue is mediated by glial glutamate and acetylcholine receptors.

Journal: Journal of neurochemistry 20050501

Title: Enantiospecificity of glutamate carboxypeptidase II inhibition.

Journal: Journal of medicinal chemistry 20050407

Title: Inhibition of glutamate carboxypeptidase II (NAALADase) protects against dynorphin A-induced ischemic spinal cord injury in rats.

Journal: European journal of pharmacology 20050131

Title: 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: Journal of molecular neuroscience : MN 20050101

Title: 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.

Journal: Archives of biochemistry and biophysics 20040401

Title: Protection against glucose-induced neuronal death by NAAG and GCP II inhibition is regulated by mGluR3.

Journal: Journal of neurochemistry 20040401

Title: Synthesis of urea-based inhibitors as active site probes of glutamate carboxypeptidase II: efficacy as analgesic agents.

Journal: Journal of medicinal chemistry 20040325

Title: Effects of GCP-II inhibition on responses of dorsal horn neurones after inflammation and neuropathy: an electrophysiological study in the rat.

Journal: Neuropeptides 20031001

Title: Synthesis and biological evaluation of hydroxamate-Based inhibitors of glutamate carboxypeptidase II.

Journal: Bioorganic & medicinal chemistry letters 20030707

Title: NAALADase inhibition protects motor neurons against chronic glutamate toxicity.

Journal: European journal of pharmacology 20030627

Title: Synthesis and biological evaluation of thiol-based inhibitors of glutamate carboxypeptidase II: discovery of an orally active GCP II inhibitor.

Journal: Journal of medicinal chemistry 20030508

Title: Morphine tolerance and reward but not expression of morphine dependence are inhibited by the selective glutamate carboxypeptidase II (GCP II, NAALADase) inhibitor, 2-PMPA.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20030301

Title: Glutamate carboxypeptidase II inhibition as a novel therapeutic target.

Journal: Advances in experimental medicine and biology 20030101

Title: Kinetics and inhibition of glutamate carboxypeptidase II using a microplate assay.

Journal: Analytical biochemistry 20021101

Title: Deletion of the glutamate carboxypeptidase II gene in mice reveals a second enzyme activity that hydrolyzes N-acetylaspartylglutamate.

Journal: Journal of neurochemistry 20021001

Title: Molecular modeling of the interactions of glutamate carboxypeptidase II with its potent NAAG-based inhibitors.

Journal: Journal of medicinal chemistry 20020912

Title: NAALADase (GCP II) inhibition prevents cocaine-kindled seizures.

Journal: Neuropharmacology 20020901

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

Journal: European journal of pharmacology 20020222

Title: Effect of 2-(phosphono-methyl)-pentanedioic acid on allodynia and afferent ectopic discharges in a rat model of neuropathic pain.

Journal: The Journal of pharmacology and experimental therapeutics 20020201

Title: 11C-MCG: synthesis, uptake selectivity, and primate PET of a probe for glutamate carboxypeptidase II (NAALADase).

Journal: Molecular imaging 20020101

Title: Neuroprotection mediated by glutamate carboxypeptidase II (NAALADase) inhibition requires TGF-beta.

Journal: European journal of pharmacology 20011026

Title: Binding of the glutamate carboxypeptidase II (NAALADase) inhibitor 2-PMPA to rat brain membranes.

Journal: European journal of pharmacology 20010914

Title: Neuroprotection afforded by NAAG and NAALADase inhibition requires glial cells and metabotropic glutamate receptor activation.

Journal: European journal of pharmacology 20010824

Title: Spinal N-acetyl-alpha-linked acidic dipeptidase (NAALADase) inhibition attenuates mechanical allodynia induced by paw carrageenan injection in the rat.

Journal: Brain research 20010803

Title: 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).

Journal: Synapse (New York, N.Y.) 20010701

Title: Design of remarkably simple, yet potent urea-based inhibitors of glutamate carboxypeptidase II (NAALADase).

Journal: Journal of medicinal chemistry 20010201

Title: Inhibition of spinal N-acetylated-alpha-linked acidic dipeptidase produces an antinociceptive effect in the rat formalin test.

Journal: Neuroscience 20010101

Title: N-acetylaspartylglutamate (NAAG) is the probable mediator of axon-to-glia signaling in the crayfish medial giant nerve fiber.

Journal: Neuroscience 20010101

Title: Mechanisms for clearance of released N-acetylaspartylglutamate in crayfish nerve fibers: implications for axon-glia signaling.

Journal: Neuroscience 20010101

Title: Rais R, et al. Bioanalytical method for evaluating the pharmacokinetics of the GCP-II inhibitor 2-phosphonomethyl pentanedioic acid (2-PMPA). J Pharm Biomed Anal. 2014 Jan;88:162-9.

Title: Zuo D, et al. Existence of glia mitigated ketamine-induced neurotoxicity in neuron-glia mixed cultures of neonatal rat cortex and the glia-mediated protective effect of 2-PMPA. Neurotoxicology. 2014 Sep;44:218-30.

Title: Baslow MH, et al. 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. J Mol Neurosci. 2005;26(1):1-15.

Title: Nagel J, et al. Effects of NAAG peptidase inhibitor 2-PMPA in model chronic pain-relation to brain concentration. Neuropharmacology. 2006 Dec;51(7-8):1163-71.

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