Literature DB >> 19897367

Bioisosterism of urea-based GCPII inhibitors: Synthesis and structure-activity relationship studies.

Haofan Wang1, Youngjoo Byun, Cyril Barinka, Mrudula Pullambhatla, Hyo-Eun C Bhang, James J Fox, Jacek Lubkowski, Ronnie C Mease, Martin G Pomper.   

Abstract

We report a strategy based on bioisosterism to improve the physicochemical properties of existing hydrophilic, urea-based GCPII inhibitors. Comprehensive structure-activity relationship studies of the P1' site of ZJ-43- and DCIBzL-based compounds identified several glutamate-free inhibitors with K(i) values below 20nM. Among them, compound 32d (K(i)=11nM) exhibited selective uptake in GCPII-expressing tumors by SPECT-CT imaging in mice. A novel conformational change of amino acids in the S1' pharmacophore pocket was observed in the X-ray crystal structure of GCPII complexed with 32d. Copyright 2009 Elsevier Ltd. All rights reserved.

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Year:  2009        PMID： 19897367      PMCID： PMC2818328          DOI： 10.1016/j.bmcl.2009.10.061

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  32 in total

1.  Glutamate carboxypeptidase II levels in rodent brain using [125I]DCIT quantitative autoradiography.

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Journal:  Neurosci Lett       Date:  2005-10-28       Impact factor: 3.046

2.  Selective inhibition of NAALADase, which converts NAAG to glutamate, reduces ischemic brain injury.

Authors:  B S Slusher; J J Vornov; A G Thomas; P D Hurn; I Harukuni; A Bhardwaj; R J Traystman; M B Robinson; P Britton; X C Lu; F C Tortella; K M Wozniak; M Yudkoff; B M Potter; P F Jackson
Journal:  Nat Med       Date:  1999-12       Impact factor: 53.440

3.  Development of a stable radioiodinating reagent to label monoclonal antibodies for radiotherapy of cancer.

Authors:  D S Wilbur; S W Hadley; M D Hylarides; P G Abrams; P A Beaumier; A C Morgan; J M Reno; A R Fritzberg
Journal:  J Nucl Med       Date:  1989-02       Impact factor: 10.057

4.  Mice lacking glutamate carboxypeptidase II are protected from peripheral neuropathy and ischemic brain injury.

Authors:  Dean J Bacich; Krystyna M Wozniak; X-C May Lu; Denize S O'Keefe; Noelle Callizot; Warren D W Heston; Barbara S Slusher
Journal:  J Neurochem       Date:  2005-10       Impact factor: 5.372

Review 5.  The neurotransmitter N-acetylaspartylglutamate in models of pain, ALS, diabetic neuropathy, CNS injury and schizophrenia.

Authors:  Joseph H Neale; Rafal T Olszewski; Laura M Gehl; Barbara Wroblewska; Tomasz Bzdega
Journal:  Trends Pharmacol Sci       Date:  2005-09       Impact factor: 14.819

6.  Interactions between human glutamate carboxypeptidase II and urea-based inhibitors: structural characterization.

Authors:  Cyril Barinka; Youngjoo Byun; Crystal L Dusich; Sangeeta R Banerjee; Ying Chen; Mark Castanares; Alan P Kozikowski; Ronnie C Mease; Martin G Pomper; Jacek Lubkowski
Journal:  J Med Chem       Date:  2008-12-25       Impact factor: 7.446

7.  Structural basis of interactions between human glutamate carboxypeptidase II and its substrate analogs.

Authors:  Cyril Barinka; Klara Hlouchova; Miroslava Rovenska; Pavel Majer; Miroslawa Dauter; Niyada Hin; Yao-Sen Ko; Takashi Tsukamoto; Barbara S Slusher; Jan Konvalinka; Jacek Lubkowski
Journal:  J Mol Biol       Date:  2008-01-05       Impact factor: 5.469

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

Authors:  Cyril Barinka; Miroslava Rovenská; Petra Mlcochová; Klára Hlouchová; Anna Plechanovová; Pavel Majer; Takashi Tsukamoto; Barbara S Slusher; Jan Konvalinka; Jacek Lubkowski
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9.  Synthesis and evaluation of technetium-99m- and rhenium-labeled inhibitors of the prostate-specific membrane antigen (PSMA).

Authors:  Sangeeta R Banerjee; Catherine A Foss; Mark Castanares; Ronnie C Mease; Youngjoo Byun; James J Fox; John Hilton; Shawn E Lupold; Alan P Kozikowski; Martin G Pomper
Journal:  J Med Chem       Date:  2008-07-19       Impact factor: 7.446

10.  Structure of glutamate carboxypeptidase II, a drug target in neuronal damage and prostate cancer.

Authors:  Jeroen R Mesters; Cyril Barinka; Weixing Li; Takashi Tsukamoto; Pavel Majer; Barbara S Slusher; Jan Konvalinka; Rolf Hilgenfeld
Journal:  EMBO J       Date:  2006-02-09       Impact factor: 11.598
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  28 in total

Review 1.  GCPII imaging and cancer.

Authors:  C A Foss; R C Mease; S Y Cho; H J Kim; M G Pomper
Journal:  Curr Med Chem       Date:  2012       Impact factor: 4.530

2.  A remote arene-binding site on prostate specific membrane antigen revealed by antibody-recruiting small molecules.

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Journal:  J Am Chem Soc       Date:  2010-09-15       Impact factor: 15.419

3.  [(18)F]Fluorobenzoyllysinepentanedioic Acid Carbamates: New Scaffolds for Positron Emission Tomography (PET) Imaging of Prostate-Specific Membrane Antigen (PSMA).

Authors:  Xing Yang; Ronnie C Mease; Mrudula Pullambhatla; Ala Lisok; Ying Chen; Catherine A Foss; Yuchuan Wang; Hassan Shallal; Hannah Edelman; Adam T Hoye; Giorgio Attardo; Sridhar Nimmagadda; Martin G Pomper
Journal:  J Med Chem       Date:  2015-12-16       Impact factor: 7.446

Review 4.  Current use of PSMA-PET in prostate cancer management.

Authors:  Tobias Maurer; Matthias Eiber; Markus Schwaiger; Jürgen E Gschwend
Journal:  Nat Rev Urol       Date:  2016-02-23       Impact factor: 14.432

Review 5.  PET imaging in prostate cancer: focus on prostate-specific membrane antigen.

Authors:  Ronnie C Mease; Catherine A Foss; Martin G Pomper
Journal:  Curr Top Med Chem       Date:  2013       Impact factor: 3.295

Review 6.  Glutamate carboxypeptidase II in diagnosis and treatment of neurologic disorders and prostate cancer.

Authors:  C Bařinka; C Rojas; B Slusher; M Pomper
Journal:  Curr Med Chem       Date:  2012       Impact factor: 4.530

7.  MR-Guided Delivery of Hydrophilic Molecular Imaging Agents Across the Blood-Brain Barrier Through Focused Ultrasound.

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Journal:  Mol Imaging Biol       Date:  2017-02       Impact factor: 3.488

8.  2-Aminoadipic Acid-C(O)-Glutamate Based Prostate-Specific Membrane Antigen Ligands for Potential Use as Theranostics.

Authors:  Ryo Nakajima; Zora Nováková; Werner Tueckmantel; Lucia Motlová; Cyril Bařinka; Alan P Kozikowski
Journal:  ACS Med Chem Lett       Date:  2018-10-24       Impact factor: 4.345

9.  Novel substrate-based inhibitors of human glutamate carboxypeptidase II with enhanced lipophilicity.

Authors:  Anna Plechanovová; Youngjoo Byun; Glenda Alquicer; L'ubica Skultétyová; Petra Mlčochová; Adriana Němcová; Hyung-Joon Kim; Michal Navrátil; Ronnie Mease; Jacek Lubkowski; Martin Pomper; Jan Konvalinka; Lubomír Rulíšek; Cyril Bařinka
Journal:  J Med Chem       Date:  2011-10-11       Impact factor: 7.446

Review 10.  The therapeutic and diagnostic potential of the prostate specific membrane antigen/glutamate carboxypeptidase II (PSMA/GCPII) in cancer and neurological disease.

Authors:  James C Evans; Meenakshi Malhotra; John F Cryan; Caitriona M O'Driscoll
Journal:  Br J Pharmacol       Date:  2016-09-23       Impact factor: 8.739
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