Literature DB >> 25614109

Saccharin: a lead compound for structure-based drug design of carbonic anhydrase IX inhibitors.

Brian P Mahon1, Alex M Hendon1, Jenna M Driscoll1, Gregory M Rankin2, Sally-Ann Poulsen2, Claudiu T Supuran3, Robert McKenna4.   

Abstract

Carbonic anhydrase IX (CA IX) is a key modulator of aggressive tumor behavior and a prognostic marker and target for several cancers. Saccharin (SAC) based compounds may provide an avenue to overcome CA isoform specificity, as they display both nanomolar affinity and preferential binding, for CA IX compared to CA II (>50-fold for SAC and >1000-fold when SAC is conjugated to a carbohydrate moiety). The X-ray crystal structures of SAC and a SAC-carbohydrate conjugate bound to a CA IX-mimic are presented and compared to CA II. The structures provide substantial new insight into the mechanism of SAC selective CA isoform inhibition. Published by Elsevier Ltd.

Entities:  

Keywords:  CA IX-mimic; Carbonic anhydrase IX; Metalloenzyme; Saccharin; Structure-based drug design

Mesh：

Substances：

Year:  2014        PMID： 25614109      PMCID： PMC4352949          DOI： 10.1016/j.bmc.2014.12.030

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  44 in total

Review 1.  The catalytic mechanism of mammalian carbonic anhydrases.

Authors:  S Lindskog; D N Silverman
Journal:  EXS       Date:  2000

2.  Saccharin inhibits carbonic anhydrases: possible explanation for its unpleasant metallic aftertaste.

Authors:  Karen Köhler; Alexander Hillebrecht; Johannes Schulze Wischeler; Alessio Innocenti; Andreas Heine; Claudiu T Supuran; Gerhard Klebe
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

Review 3.  Carbonic anhydrases: novel therapeutic applications for inhibitors and activators.

Authors:  Claudiu T Supuran
Journal:  Nat Rev Drug Discov       Date:  2008-02       Impact factor: 84.694

4.  Carbonic anhydrases: from biomedical applications of the inhibitors and activators to biotechnological use for CO(2) capture.

Authors:  Claudiu T Supuran
Journal:  J Enzyme Inhib Med Chem       Date:  2013-04       Impact factor: 5.051

Review 5.  Agents described in the Molecular Imaging and Contrast Agent Database for imaging carbonic anhydrase IX expression.

Authors:  Deborah Sneddon; Sally-Ann Poulsen
Journal:  J Enzyme Inhib Med Chem       Date:  2014-02-10       Impact factor: 5.051

6.  A novel class of carbonic anhydrase inhibitors: glycoconjugate benzene sulfonamides prepared by "click-tailing".

Authors:  Brendan L Wilkinson; Laurent F Bornaghi; Todd A Houston; Alessio Innocenti; Claudiu T Supuran; Sally-Ann Poulsen
Journal:  J Med Chem       Date:  2006-11-02       Impact factor: 7.446

7.  Entrapment of carbon dioxide in the active site of carbonic anhydrase II.

Authors:  John F Domsic; Balendu Sankara Avvaru; Chae Un Kim; Sol M Gruner; Mavis Agbandje-McKenna; David N Silverman; Robert McKenna
Journal:  J Biol Chem       Date:  2008-09-02       Impact factor: 5.157

8.  Response of CAIX and CAXII to in vitro re-oxygenation and clinical significance of the combined expression in NSCLC patients.

Authors:  Marius Ilie; Véronique Hofman; Joséphine Zangari; Johanna Chiche; Jérôme Mouroux; Nathalie M Mazure; Jacques Pouysségur; Patrick Brest; Paul Hofman
Journal:  Lung Cancer       Date:  2013-07-30       Impact factor: 5.705

9.  Crystal structure of the catalytic domain of the tumor-associated human carbonic anhydrase IX.

Authors:  Vincenzo Alterio; Mika Hilvo; Anna Di Fiore; Claudiu T Supuran; Peiwen Pan; Seppo Parkkila; Andrea Scaloni; Jaromir Pastorek; Silvia Pastorekova; Carlo Pedone; Andrea Scozzafava; Simona Maria Monti; Giuseppina De Simone
Journal:  Proc Natl Acad Sci U S A       Date:  2009-09-14       Impact factor: 11.205

10.  Inhibition of carbonic anhydrase activity modifies the toxicity of doxorubicin and melphalan in tumour cells in vitro.

Authors:  Roben G Gieling; Catriona A Parker; Lisa A De Costa; Naomi Robertson; Adrian L Harris; Ian J Stratford; Kaye J Williams
Journal:  J Enzyme Inhib Med Chem       Date:  2012-11-19       Impact factor: 5.051
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  15 in total

1.  Synthesis of saccharin-glycoconjugates targeting carbonic anhydrase using a one-pot cyclization/deprotection strategy.

Authors:  Akilah B Murray; Marta Quadri; Haoxi Li; Robert McKenna; Nicole A Horenstein
Journal:  Carbohydr Res       Date:  2019-03-19       Impact factor: 2.104

2.  Saccharin Aza Bioisosteres-Synthesis and Preclinical Property Comparisons.

Authors:  Yantao Chen; Carl-Johan Aurell; Anna Pettersen; Richard J Lewis; Martin A Hayes; Matti Lepistö; Anna C Jonson; Hanna Leek; Linda Thunberg
Journal:  ACS Med Chem Lett       Date:  2017-05-01       Impact factor: 4.345

3.  Structure activity study of carbonic anhydrase IX: Selective inhibition with ureido-substituted benzenesulfonamides.

Authors:  Mam Y Mboge; Brian P Mahon; Nicole Lamas; Lillien Socorro; Fabrizio Carta; Claudiu T Supuran; Susan C Frost; Robert McKenna
Journal:  Eur J Med Chem       Date:  2017-03-19       Impact factor: 6.514

Review 4.  New Developments in Carbonic Anhydrase IX-Targeted Fluorescence and Nuclear Imaging Agents.

Authors:  Kuo-Ting Chen; Yann Seimbille
Journal:  Int J Mol Sci       Date:  2022-05-30       Impact factor: 6.208

5.  Sweet Binders: Carbonic Anhydrase IX in Complex with Sucralose.

Authors:  Carrie L Lomelino; Akilah B Murray; Claudiu T Supuran; Robert McKenna
Journal:  ACS Med Chem Lett       Date:  2018-05-10       Impact factor: 4.345

6.  Observed surface lysine acetylation of human carbonic anhydrase II expressed in Escherichia coli.

Authors:  Brian P Mahon; Carrie L Lomelino; Antonieta L Salguero; Jenna M Driscoll; Melissa A Pinard; Robert McKenna
Journal:  Protein Sci       Date:  2015-09-15       Impact factor: 6.725

7.  Synthesis of Novel Saccharin Derivatives.

Authors:  Gregory M Rankin; Sally-Ann Poulsen
Journal:  Molecules       Date:  2017-03-23       Impact factor: 4.411

Review 8.  Crystallography and Its Impact on Carbonic Anhydrase Research.

Authors:  Carrie L Lomelino; Jacob T Andring; Robert McKenna
Journal:  Int J Med Chem       Date:  2018-09-13

9.  Selective inhibition of carbonic anhydrase IX over carbonic anhydrase XII in breast cancer cells using benzene sulfonamides: Disconnect between activity and growth inhibition.

Authors:  Mam Y Mboge; Zhijuan Chen; Alyssa Wolff; John V Mathias; Chingkuang Tu; Kevin D Brown; Murat Bozdag; Fabrizio Carta; Claudiu T Supuran; Robert McKenna; Susan C Frost
Journal:  PLoS One       Date:  2018-11-19       Impact factor: 3.240

Review 10.  Cancer Drug Development of Carbonic Anhydrase Inhibitors beyond the Active Site.

Authors:  Srishti Singh; Carrie L Lomelino; Mam Y Mboge; Susan C Frost; Robert McKenna
Journal:  Molecules       Date:  2018-04-30       Impact factor: 4.411
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