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Original Article

Carbonic Anhydrase Inhibitors: Synthesis of Sulfonamides Incorporating 2, 4, 6–Trisubstituted-Pyridinium-Ethylcarboxamido Moieties Possessing Membrane-Impermeability and in Vivo Selectivity for the Membrane-Bound (CA IV) Versus the Cytosolic (CA I and CA II) Isozymes

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Pages 381-401 | Received 24 Sep 1999, Published online: 02 Jul 2010

Keep up to date with the latest research on this topic with citation updates for this article.

Read on this site (10)

Sabina Zamanova, Ahmed M Shabana, Utpal K Mondal & Marc A Ilies. (2019) Carbonic anhydrases as disease markers. Expert Opinion on Therapeutic Patents 29:7, pages 509-533.
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Vincenzo Alterio, Davide Esposito, Simona Maria Monti, Claudiu T. Supuran & Giuseppina De Simone. (2018) Crystal structure of the human carbonic anhydrase II adduct with 1-(4-sulfamoylphenyl-ethyl)-2,4,6-triphenylpyridinium perchlorate, a membrane-impermeant, isoform selective inhibitor. Journal of Enzyme Inhibition and Medicinal Chemistry 33:1, pages 151-157.
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Simona Maria Monti, Claudiu T Supuran & Giuseppina De Simone. (2013) Anticancer carbonic anhydrase inhibitors: a patent review (2008 – 2013). Expert Opinion on Therapeutic Patents 23:6, pages 737-749.
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Mayank Aggarwal, Christopher D. Boone, Bhargav Kondeti & Robert McKenna. (2013) Structural annotation of human carbonic anhydrases. Journal of Enzyme Inhibition and Medicinal Chemistry 28:2, pages 267-277.
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Mayank Aggarwal & Robert McKenna. (2012) Update on carbonic anhydrase inhibitors: a patent review (2008 – 2011). Expert Opinion on Therapeutic Patents 22:8, pages 903-915.
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Kalyan K. Sethi, Suvendu K. Sahoo, Jayaprakash N. Pichikala & Padilam Suresh. (2012) Carbonic anhydrase I and II inhibition with natural products: caffeine and piperine. Journal of Enzyme Inhibition and Medicinal Chemistry 27:1, pages 97-100.
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Silvia Pastorekova, Seppo Parkkila, Jaromir Pastorek & Claudiu T. Supuran. (2004) Review Article. Journal of Enzyme Inhibition and Medicinal Chemistry 19:3, pages 199-229.
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Marc A Ilies, Claudiu T Supuran & Andrea Scozzafava. (2002) Therapeutic applications of serine protease inhibitors. Expert Opinion on Therapeutic Patents 12:8, pages 1181-1214.
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Claudiu T Supuran & Andrea Scozzafava. (2002) Applications of carbonic anhydrase inhibitors and activators in therapy. Expert Opinion on Therapeutic Patents 12:2, pages 217-242.
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Antonio Mastrolorenzo, Andrea Scozzafava & Claudiu T Supuran. (2001) Small molecule antagonists of chemokine receptors as emerging anti-HIV agents. Expert Opinion on Therapeutic Patents 11:8, pages 1245-1252.
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Articles from other publishers (34)

Claudiu T. Supuran. (2023) A simple yet multifaceted 90 years old, evergreen enzyme: Carbonic anhydrase, its inhibition and activation. Bioorganic & Medicinal Chemistry Letters 93, pages 129411.
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Amit Kumar, Kiran Siwach, Claudiu T. Supuran & Pawan K. Sharma. (2022) A decade of tail-approach based design of selective as well as potent tumor associated carbonic anhydrase inhibitors. Bioorganic Chemistry 126, pages 105920.
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Pengcheng Lv, Yinyi Cai, Jiayi Luo & Kun Chen. (2022) Recent Advances in the Design and Synthesis of Small Molecule Carbonic Anhydrase IX Inhibitors. Current Topics in Medicinal Chemistry 22:7, pages 550-560.
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Laila Rubab, Sumbal Afroz, Sajjad Ahmad, Saddam Hussain, Iram Nawaz, Ali Irfan, Fozia Batool, Katarzyna Kotwica-Mojzych & Mariusz Mojzych. (2022) An Update on Synthesis of Coumarin Sulfonamides as Enzyme Inhibitors and Anticancer Agents. Molecules 27:5, pages 1604.
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Utpal K. Mondal, Kate Doroba, Ahmed M. Shabana, Rachel Adelberg, Md. Raqibul Alam, Claudiu T. Supuran & Marc A. Ilies. (2021) PEG Linker Length Strongly Affects Tumor Cell Killing by PEGylated Carbonic Anhydrase Inhibitors in Hypoxic Carcinomas Expressing Carbonic Anhydrase IX. International Journal of Molecular Sciences 22:3, pages 1120.
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Jacob T. Andring, Mallorie Fouch, Suleyman Akocak, Andrea Angeli, Claudiu T. Supuran, Marc A. Ilies & Robert McKenna. (2020) Structural Basis of Nanomolar Inhibition of Tumor-Associated Carbonic Anhydrase IX: X-Ray Crystallographic and Inhibition Study of Lipophilic Inhibitors with Acetazolamide Backbone. Journal of Medicinal Chemistry 63:21, pages 13064-13075.
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Suleyman Akocak, Özlen Güzel-Akdemir, Rajesh Kishore Kumar Sanku, Samson S. Russom, Bogdan I. Iorga, Claudiu T. Supuran & Marc A. Ilies. (2020) Pyridinium derivatives of 3-aminobenzenesulfonamide are nanomolar-potent inhibitors of tumor-expressed carbonic anhydrase isozymes CA IX and CA XII. Bioorganic Chemistry 103, pages 104204.
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Ali Irfan, Laila Rubab, Mishbah Ur Rehman, Rukhsana Anjum, Sami Ullah, Mahwish Marjana, Saba Qadeer & Sadia Sana. (2020) Coumarin sulfonamide derivatives: An emerging class of therapeutic agents. Heterocyclic Communications 26:1, pages 46-59.
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Vincenzo Alterio, Markus Kellner, Davide Esposito, Friederike Liesche-Starnecker, Silvia Bua, Claudiu T. Supuran, Simona Maria Monti, Reinhard Zeidler & Giuseppina De Simone. (2019) Biochemical and Structural Insights into Carbonic Anhydrase XII/Fab6A10 Complex. Journal of Molecular Biology 431:24, pages 4910-4921.
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Ahmed M. Shabana & Marc A. Ilies. 2019. Targeted Nanosystems for Therapeutic Applications: New Concepts, Dynamic Properties, Efficiency, and Toxicity. Targeted Nanosystems for Therapeutic Applications: New Concepts, Dynamic Properties, Efficiency, and Toxicity 223 252 .
Marc A. Ilies & Jean-Yves Winum. 2019. Carbonic Anhydrases. Carbonic Anhydrases 331 365 .
Suleyman Akocak, M. Raqibul Alam, Ahmed M. Shabana, Rajesh Kishore Kumar Sanku, Daniela Vullo, Harry Thompson, Erik R. Swenson, Claudiu T. Supuran & Marc A. Ilies. (2016) PEGylated Bis-Sulfonamide Carbonic Anhydrase Inhibitors Can Efficiently Control the Growth of Several Carbonic Anhydrase IX-Expressing Carcinomas. Journal of Medicinal Chemistry 59:10, pages 5077-5088.
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Sarah L. Alderman, Till S. Harter, Jonathan M. Wilson, Claudiu T. Supuran, Anthony P. Farrell & Colin J. Brauner. (2016) Evidence for a plasma-accessible carbonic anhydrase in the lumen of salmon heart that may enhance oxygen delivery to the myocardium. Journal of Experimental Biology 219:5, pages 719-724.
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Mattia Mori, Ylenia Cau, Giulia Vignaroli, Ilaria Laurenzana, Antonella Caivano, Daniela Vullo, Claudiu T. Supuran & Maurizio Botta. (2015) Hit Recycling: Discovery of a Potent Carbonic Anhydrase Inhibitor by in Silico Target Fishing . ACS Chemical Biology 10:9, pages 1964-1969.
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Claudiu T Supuran & Clemente CapassoSuleyman AkocakMarc A Ilies. 2014. Targeting Carbonic Anhydrases. Targeting Carbonic Anhydrases 34 51 .
Vincenzo Alterio, Peiwen Pan, Seppo Parkkila, Martina Buonanno, Claudiu T. Supuran, Simona M. Monti & Giuseppina De Simone. (2014) The structural comparison between membrane-associated human carbonic anhydrases provides insights into drug design of selective inhibitors. Biopolymers 101:7, pages 769-778.
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Nadia Lounnas, Célia Rosilio, Marielle Nebout, Didier Mary, Emmanuel Griessinger, Zouhour Neffati, Johanna Chiche, Hergen Spits, Thijs J. Hagenbeek, Vahid Asnafi, Sally-Ann Poulsen, Claudiu T. Supuran, Jean-François Peyron & Véronique Imbert. (2013) Pharmacological inhibition of carbonic anhydrase XII interferes with cell proliferation and induces cell apoptosis in T-cell lymphomas. Cancer Letters 333:1, pages 76-88.
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Mayank Aggarwal, Bhargav Kondeti & Robert McKenna. (2013) Insights towards sulfonamide drug specificity in α-carbonic anhydrases. Bioorganic & Medicinal Chemistry 21:6, pages 1526-1533.
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Vincenzo Alterio, Anna Di Fiore, Katia D’Ambrosio, Claudiu T. Supuran & Giuseppina De Simone. (2012) Multiple Binding Modes of Inhibitors to Carbonic Anhydrases: How to Design Specific Drugs Targeting 15 Different Isoforms?. Chemical Reviews 112:8, pages 4421-4468.
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Fabrizio Carta, Mayank Aggarwal, Alfonso Maresca, Andrea Scozzafava, Robert McKenna, Emanuela Masini & Claudiu T. Supuran. (2012) Dithiocarbamates Strongly Inhibit Carbonic Anhydrases and Show Antiglaucoma Action in Vivo. Journal of Medicinal Chemistry 55:4, pages 1721-1730.
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Khyati Dave, Marc A. Ilies, Andrea Scozzafava, Claudia Temperini, Daniela Vullo & Claudiu T. Supuran. (2011) An inhibitor-like binding mode of a carbonic anhydrase activator within the active site of isoform II. Bioorganic & Medicinal Chemistry Letters 21:9, pages 2764-2768.
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Khyati Dave, Andrea Scozzafava, Daniela Vullo, Claudiu T. Supuran & Marc A. Ilies. (2011) Pyridinium derivatives of histamine are potent activators of cytosolic carbonic anhydrase isoforms I, II and VII. Organic & Biomolecular Chemistry 9:8, pages 2790.
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Fabrizio Carta, Alfonso Maresca, Andrea Scozzafava, Daniela Vullo & Claudiu T. Supuran. (2009) Carbonic anhydrase inhibitors. Diazenylbenzenesulfonamides are potent and selective inhibitors of the tumor-associated isozymes IX and XII over the cytosolic isoforms I and II. Bioorganic & Medicinal Chemistry 17:20, pages 7093-7099.
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Vincenzo Alterio, Anna Di Fiore, Katia D'Ambrosio, Claudiu T. Supuran & Giuseppina De Simone. 2009. Drug Design of Zinc‐Enzyme Inhibitors. Drug Design of Zinc‐Enzyme Inhibitors 138 66 .
Claudiu T. Supuran & Jean‐Yves Winum. 2009. Drug Design of Zinc‐Enzyme Inhibitors. Drug Design of Zinc‐Enzyme Inhibitors 399 413 .
Özlen Güzel, Alfonso Maresca, Andrea Scozzafava, Aydın Salman, Alexandru T. Balaban & Claudiu T. Supuran. (2009) Discovery of Low Nanomolar and Subnanomolar Inhibitors of the Mycobacterial β-Carbonic Anhydrases Rv1284 and Rv3273. Journal of Medicinal Chemistry 52:13, pages 4063-4067.
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Özlen Güzel, Alfonso Maresca, Andrea Scozzafava, Aydın Salman, Alexandru T. Balaban & Claudiu T. Supuran. (2009) Carbonic anhydrase inhibitors. Synthesis of 2,4,6-trimethylpyridinium derivatives of 2-(hydrazinocarbonyl)-3-aryl-1H-indole-5-sulfonamides acting as potent inhibitors of the tumor-associated isoform IX and XII. Bioorganic & Medicinal Chemistry Letters 19:11, pages 2931-2934.
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Claudiu T. Supuran. (2008) Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nature Reviews Drug Discovery 7:2, pages 168-181.
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Claudiu T. Supuran & Andrea Scozzafava. (2007) Carbonic anhydrases as targets for medicinal chemistry. Bioorganic & Medicinal Chemistry 15:13, pages 4336-4350.
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Claudiu T Supuran. (2007) Therapeutic applications of the carbonic anhydrase inhibitors. Therapy 4:3, pages 355-378.
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Alexander Hillebrecht, Claudiu T. Supuran & Gerhard Klebe. (2006) Integrated Approach Using Protein and Ligand Information to Analyze Selectivity- and Affinity-Determining Features of Carbonic Anhydrase Isozymes. ChemMedChem 1:8, pages 839-853.
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Daniela Vullo, Bente Steffansen, Birger Brodin, Claudiu T. Supuran, Andrea Scozzafava & Carsten Uhd Nielsen. (2006) Carbonic anhydrase inhibitors: Transepithelial transport of thioureido sulfonamide inhibitors of the cancer-associated isozyme IX is dependent on efflux transporters. Bioorganic & Medicinal Chemistry 14:7, pages 2418-2427.
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Silvia Pastorekova, Angela Casini, Andrea Scozzafava, Daniela Vullo, Jaromir Pastorek & Claudiu T. Supuran. (2004) Carbonic anhydrase inhibitors: The first selective, membrane-impermeant inhibitors targeting the tumor-associated isozyme IX. Bioorganic & Medicinal Chemistry Letters 14:4, pages 869-873.
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Claudiu T. Supuran, Andrea Scozzafava & Angela Casini. (2002) Carbonic anhydrase inhibitors. Medicinal Research Reviews 23:2, pages 146-189.
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