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Dithiocarbamates strongly inhibit the β-class carbonic anhydrases from Mycobacterium tuberculosis

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Pages 407-411 | Received 16 Oct 2011, Accepted 10 Nov 2011, Published online: 06 Dec 2011

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Simone Giovannuzzi, Viviana De Luca, Alessio Nocentini, Clemente Capasso & Claudiu T. Supuran. (2022) Coumarins inhibit η-class carbonic anhydrase from Plasmodium falciparum. Journal of Enzyme Inhibition and Medicinal Chemistry 37:1, pages 680-685.
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Mikhail Krasavin, Raivis Žalubovskis, Aiga Grandāne, Ilona Domračeva, Petr Zhmurov & Claudiu T. Supuran. (2020) Sulfocoumarins as dual inhibitors of human carbonic anhydrase isoforms IX/XII and of human thioredoxin reductase. Journal of Enzyme Inhibition and Medicinal Chemistry 35:1, pages 506-510.
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Ashok Aspatwar, Milka Hammaren, Mataleena Parikka, Seppo Parkkila, Fabrizio Carta, Murat Bozdag, Daniela Vullo & Claudiu T. Supuran. (2020) In vitro inhibition of Mycobacterium tuberculosis β-carbonic anhydrase 3 with Mono- and dithiocarbamates and evaluation of their toxicity using zebrafish developing embryos. Journal of Enzyme Inhibition and Medicinal Chemistry 35:1, pages 65-71.
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Benoit Métayer, Andrea Angeli, Agnès Mingot, Kévin Jouvin, Gwilherm Evano, Claudiu T. Supuran & Sébastien Thibaudeau. (2018) Fluoroenesulphonamides: N-sulphonylurea isosteres showing nanomolar selective cancer-related transmembrane human carbonic anhydrase inhibition. Journal of Enzyme Inhibition and Medicinal Chemistry 33:1, pages 804-808.
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Claudiu T. Supuran. (2018) Carbon- versus sulphur-based zinc binding groups for carbonic anhydrase inhibitors?. Journal of Enzyme Inhibition and Medicinal Chemistry 33:1, pages 485-495.
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Daniela Vullo, Leo Syrjänen, Marianne Kuuslahti, Seppo Parkkila & Claudiu T. Supuran. (2018) Anion inhibition studies of a beta carbonic anhydrase from the malaria mosquito Anopheles gambiae. Journal of Enzyme Inhibition and Medicinal Chemistry 33:1, pages 359-363.
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Alessio Nocentini, Daniela Vullo, Sonia Del Prete, Sameh M. Osman, Fatmah A.S. Alasmary, Zeid AlOthman, Clemente Capasso, Fabrizio Carta, Paola Gratteri & Claudiu T. Supuran. (2017) Inhibition of the β-carbonic anhydrase from the dandruff-producing fungus Malassezia globosa with monothiocarbamates. Journal of Enzyme Inhibition and Medicinal Chemistry 32:1, pages 1064-1070.
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Mikhail Krasavin, Mikhail Korsakov, Oksana Ronzhina, Tiziano Tuccinardi, Stanislav Kalinin, Muhammet Tanç & Claudiu T. Supuran. (2017) Primary mono- and bis-sulfonamides obtained via regiospecific sulfochlorination of N-arylpyrazoles: inhibition profile against a panel of human carbonic anhydrases. Journal of Enzyme Inhibition and Medicinal Chemistry 32:1, pages 920-934.
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Ashok Aspatwar, Milka Hammarén, Sanni Koskinen, Bruno Luukinen, Harlan Barker, Fabrizio Carta, Claudiu T. Supuran, Mataleena Parikka & Seppo Parkkila. (2017) β-CA-specific inhibitor dithiocarbamate Fc14–584B: a novel antimycobacterial agent with potential to treat drug-resistant tuberculosis. Journal of Enzyme Inhibition and Medicinal Chemistry 32:1, pages 832-840.
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Erol Licsandru, Muhammet Tanc, Istvan Kocsis, Mihail Barboiu & Claudiu T. Supuran. (2017) A class of carbonic anhydrase I – selective activators. Journal of Enzyme Inhibition and Medicinal Chemistry 32:1, pages 37-46.
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Alessio Nocentini, Mariangela Ceruso, Fabrizio Carta & Claudiu T. Supuran. (2016) 7-Aryl-triazolyl-substituted sulfocoumarins are potent, selective inhibitors of the tumor-associated carbonic anhydrase IX and XII. Journal of Enzyme Inhibition and Medicinal Chemistry 31:6, pages 1226-1233.
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Ayşenur Eminoğlu, Daniela Vullo, Aycan Aşık, Dilşat Nigar Çolak, Claudiu T. Supuran, Sabriye Çanakçı & Ali Osman Beldüz. (2016) Cloning, expression and biochemical characterization of a β-carbonic anhydrase from the soil bacterium Enterobacter sp. B13. Journal of Enzyme Inhibition and Medicinal Chemistry 31:6, pages 1111-1118.
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Claudiu T. Supuran, Stanislav Kalinin, Muhammet Tanç, Pakornwit Sarnpitak, Prashant Mujumdar, Sally-Ann Poulsen & Mikhail Krasavin. (2016) Isoform-selective inhibitory profile of 2-imidazoline-substituted benzene sulfonamides against a panel of human carbonic anhydrases. Journal of Enzyme Inhibition and Medicinal Chemistry 31:sup1, pages 197-202.
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Claudiu T. Supuran. (2016) CA IX stratification based on cancer treatment: a patent evaluation of US2016/0002350. Expert Opinion on Therapeutic Patents 26:10, pages 1105-1109.
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Claudiu T. Supuran. (2016) How many carbonic anhydrase inhibition mechanisms exist?. Journal of Enzyme Inhibition and Medicinal Chemistry 31:3, pages 345-360.
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Claudiu T. Supuran. (2016) Drug interaction considerations in the therapeutic use of carbonic anhydrase inhibitors. Expert Opinion on Drug Metabolism & Toxicology 12:4, pages 423-431.
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Murat Bozdag, Fabrizio Carta, Daniela Vullo, Semra Isik, Zeid AlOthman, Sameh M. Osman, Andrea Scozzafava & Claudiu T. Supuran. (2016) Dithiocarbamates with potent inhibitory activity against the Saccharomyces cerevisiae β-carbonic anhydrase. Journal of Enzyme Inhibition and Medicinal Chemistry 31:1, pages 132-136.
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Clemente Capasso & Claudiu T Supuran. (2015) Bacterial, fungal and protozoan carbonic anhydrases as drug targets. Expert Opinion on Therapeutic Targets 19:12, pages 1689-1704.
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Leonardo E. Riafrecha, Daniela Vullo, Safia Ouahrani-Bettache, Stephan Köhler, Pascal Dumy, Jean-Yves Winum, Claudiu T. Supuran & Pedro A. Colinas. (2015) Inhibition of β-carbonic anhydrases from Brucella suis with C-cinnamoyl glycosides incorporating the phenol moiety. Journal of Enzyme Inhibition and Medicinal Chemistry 30:6, pages 1017-1020.
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Joanna Ombouma, Daniela Vullo, Stephan Köhler, Pascal Dumy, Claudiu T. Supuran & Jean-Yves Winum. (2015) N-glycosyl-N-hydroxysulfamides as potent inhibitors of Brucella suis carbonic anhydrases. Journal of Enzyme Inhibition and Medicinal Chemistry 30:6, pages 1010-1012.
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Mehmet Arslan, Murat Şentürk, İsmail Fidan, Oktay Talaz, Deniz Ekinci, Sedat Coşgun & Claudiu T. Supuran. (2015) Synthesis of 3,4-dihydroxypyrrolidine-2,5-dione and 3,5-dihydroxybenzoic acid derivatives and evaluation of the carbonic anhydrase I and II inhibition. Journal of Enzyme Inhibition and Medicinal Chemistry 30:6, pages 896-900.
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Daniela Vullo, Semra Isik, Murat Bozdag, Fabrizio Carta & Claudiu T. Supuran. (2015) 7-Amino-3,4-dihydro-1H-quinolin-2-one, a compound similar to the substituted coumarins, inhibits α-carbonic anhydrases without hydrolysis of the lactam ring. Journal of Enzyme Inhibition and Medicinal Chemistry 30:5, pages 773-777.
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Leonardo E. Riafrecha, Daniela Vullo, Claudiu T. Supuran & Pedro A. Colinas. (2015) C-glycosides incorporating the 6-methoxy-2-naphthyl moiety are selective inhibitors of fungal and bacterial carbonic anhydrases. Journal of Enzyme Inhibition and Medicinal Chemistry 30:5, pages 857-861.
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Claudiu T Supuran. (2015) Nanoparticles for controlled release of anti-biofilm agents WO2014130994 (A1): a patent evaluation. Expert Opinion on Therapeutic Patents 25:8, pages 945-948.
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Ahmed M. Alafeefy, Mariangela Ceruso, Abdul-Malek S. Al-Tamimi, Sonia Del Prete, Claudiu T. Supuran & Clemente Capasso. (2015) Inhibition studies of quinazoline-sulfonamide derivatives against the γ-CA (PgiCA) from the pathogenic bacterium, Porphyromonas gingivalis. Journal of Enzyme Inhibition and Medicinal Chemistry 30:4, pages 592-596.
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Claudia Palmer & Claudiu T Supuran. (2015) A Key Opinion Leader interview: insight into the research and career of Prof. Claudiu T Supuran. Expert Opinion on Therapeutic Patents 25:4, pages 501-505.
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Daniela Vullo, Mladen Milos, Borivoj Galic, Andrea Scozzafava & Claudiu T. Supuran. (2015) Dipotassium-trioxohydroxytetrafluorotriborate, K2[B3O3F4OH], is a potent inhibitor of human carbonic anhydrases. Journal of Enzyme Inhibition and Medicinal Chemistry 30:2, pages 341-344.
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Jean-Yves Winum & Claudiu T. Supuran. (2015) Recent advances in the discovery of zinc-binding motifs for the development of carbonic anhydrase inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry 30:2, pages 321-324.
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Giuseppina De Simone, Vincenzo Alterio & Claudiu T Supuran. (2013) Exploiting the hydrophobic and hydrophilic binding sites for designing carbonic anhydrase inhibitors. Expert Opinion on Drug Discovery 8:7, pages 793-810.
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Emanuela Masini, Fabrizio Carta, Andrea Scozzafava & Claudiu T Supuran. (2013) Antiglaucoma carbonic anhydrase inhibitors: a patent review. Expert Opinion on Therapeutic Patents 23:6, pages 705-716.
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Hany S. Ibrahim, Sahar M. Abou-Seri, Muhammet Tanc, Mahmoud M. Elaasser, Hatem A. Abdel-Aziz & Claudiu T. Supuran. (2015) Isatin-pyrazole benzenesulfonamide hybrids potently inhibit tumor-associated carbonic anhydrase isoforms IX and XII. European Journal of Medicinal Chemistry 103, pages 583-593.
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İbrahim Esirden, Ramazan Ulus, Burak Aday, Muhammet Tanç, Claudiu T. Supuran & Muharrem Kaya. (2015) Synthesis of novel acridine bis-sulfonamides with effective inhibitory activity against the carbonic anhydrase isoforms I, II, IX and XII. Bioorganic & Medicinal Chemistry 23:20, pages 6573-6580.
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Cenzo Congiu, Valentina Onnis, Alessandro Deplano, Gianfranco Balboni, Nurcan Dedeoglu & Claudiu T. Supuran. (2015) Synthesis of sulfonamides incorporating piperazinyl-ureido moieties and their carbonic anhydrase I, II, IX and XII inhibitory activity. Bioorganic & Medicinal Chemistry Letters 25:18, pages 3850-3853.
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Cenzo Congiu, Valentina Onnis, Alessandro Deplano, Gianfranco Balboni, Mariangela Ceruso & Claudiu T. Supuran. (2015) Synthesis and carbonic anhydrase I, II, IX and XII inhibitory activity of sulfamates incorporating piperazinyl-ureido moieties. Bioorganic & Medicinal Chemistry 23:17, pages 5619-5625.
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Mikhail Krasavin, Mikhail Korsakov, Mikhail Dorogov, Tiziano Tuccinardi, Nurcan Dedeoglu & Claudiu T. Supuran. (2015) Probing the ‘bipolar’ nature of the carbonic anhydrase active site: Aromatic sulfonamides containing 1,3-oxazol-5-yl moiety as picomolar inhibitors of cytosolic CA I and CA II isoforms. European Journal of Medicinal Chemistry 101, pages 334-347.
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Mariangela Ceruso, Fabrizio Carta, Sameh M. Osman, Zeid Alothman, Simona Maria Monti & Claudiu T. Supuran. (2015) Inhibition studies of bacterial, fungal and protozoan β-class carbonic anhydrases with Schiff bases incorporating sulfonamide moieties. Bioorganic & Medicinal Chemistry 23:15, pages 4181-4187.
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Diaa A. Ibrahim, Deena S. Lasheen, Maysoun Y. Zaky, Amany W. Ibrahim, Daniela Vullo, Mariangela Ceruso, Claudiu T. Supuran & Dalal A. Abou El Ella. (2015) Design and synthesis of benzothiazole-6-sulfonamides acting as highly potent inhibitors of carbonic anhydrase isoforms I, II, IX and XII. Bioorganic & Medicinal Chemistry 23:15, pages 4989-4999.
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Nurcan Dedeoglu, Viviana De Luca, Semra Isik, Hatice Yildirim, Feray Kockar, Clemente Capasso & Claudiu T. Supuran. (2015) Cloning, characterization and anion inhibition study of a β-class carbonic anhydrase from the caries producing pathogen Streptococcus mutans. Bioorganic & Medicinal Chemistry 23:13, pages 2995-3001.
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Nurcan Dedeoglu, Viviana DeLuca, Semra Isik, Hatice Yildirim, Feray Kockar, Clemente Capasso & Claudiu T. Supuran. (2015) Sulfonamide inhibition study of the β-class carbonic anhydrase from the caries producing pathogen Streptococcus mutans. Bioorganic & Medicinal Chemistry Letters 25:11, pages 2291-2297.
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Aiga Grandane, Muhammet Tanc, Lorenzo Di Cesare Mannelli, Fabrizio Carta, Carla Ghelardini, Raivis Žalubovskis & Claudiu T. Supuran. (2015) 6-Substituted Sulfocoumarins Are Selective Carbonic Anhdydrase IX and XII Inhibitors with Significant Cytotoxicity against Colorectal Cancer Cells. Journal of Medicinal Chemistry 58:9, pages 3975-3983.
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Murat Bozdag, Fabrizio Carta, Daniela Vullo, Atilla Akdemir, Semra Isik, Cecilia Lanzi, Andrea Scozzafava, Emanuela Masini & Claudiu T. Supuran. (2015) Synthesis of a new series of dithiocarbamates with effective human carbonic anhydrase inhibitory activity and antiglaucoma action. Bioorganic & Medicinal Chemistry 23:10, pages 2368-2376.
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Dhiman Sankar Pal, Dipon Kumar Mondal & Rupak Datta. (2015) Identification of Metal Dithiocarbamates as a Novel Class of Antileishmanial Agents. Antimicrobial Agents and Chemotherapy 59:4, pages 2144-2152.
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Aiga Grandane, Muhammet Tanc, Raivis Žalubovskis & Claudiu T. Supuran. (2015) Synthesis of 6-aryl-substituted sulfocoumarins and investigation of their carbonic anhydrase inhibitory action. Bioorganic & Medicinal Chemistry 23:7, pages 1430-1436.
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Jekaterina Ivanova, Janis Leitans, Muhammet Tanc, Andris Kazaks, Raivis Zalubovskis, Claudiu T. Supuran & Kaspars Tars. (2015) X-ray crystallography-promoted drug design of carbonic anhydrase inhibitors. Chemical Communications 51:33, pages 7108-7111.
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Alaa A.-M. Abdel-Aziz, Adel S. El-Azab, Mariangela Ceruso & Claudiu T. Supuran. (2014) Carbonic anhydrase inhibitory activity of sulfonamides and carboxylic acids incorporating cyclic imide scaffolds. Bioorganic & Medicinal Chemistry Letters 24:22, pages 5185-5189.
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Claudiu T Supuran & Clemente CapassoFabrizio CartaMurat BozdagMuhammet TancClaudiu T Supuran. 2014. Targeting Carbonic Anhydrases. Targeting Carbonic Anhydrases 114 130 .
Sonia Del Prete, Daniela Vullo, Gillian M. Fisher, Katherine T. Andrews, Sally-Ann Poulsen, Clemente Capasso & Claudiu T. Supuran. (2014) Discovery of a new family of carbonic anhydrases in the malaria pathogen Plasmodium falciparum —The η-carbonic anhydrases. Bioorganic & Medicinal Chemistry Letters 24:18, pages 4389-4396.
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Daniela Vullo, Sonia Del Prete, Sameh M. Osman, Andrea Scozzafava, Zeid Alothman, Claudiu T. Supuran & Clemente Capasso. (2014) Anion inhibition study of the β-class carbonic anhydrase (PgiCAb) from the oral pathogen Porphyromonas gingivalis. Bioorganic & Medicinal Chemistry Letters 24:18, pages 4402-4406.
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Mehri Haeili, Casey Moore, Christopher J. C. Davis, James B. Cochran, Santosh Shah, Tej B. Shrestha, Yaofang Zhang, Stefan H. Bossmann, William H. Benjamin, Olaf Kutsch & Frank Wolschendorf. (2014) Copper Complexation Screen Reveals Compounds with Potent Antibiotic Properties against Methicillin-Resistant Staphylococcus aureus. Antimicrobial Agents and Chemotherapy 58:7, pages 3727-3736.
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Leo Syrjänen, Seppo Parkkila, Andrea Scozzafava & Claudiu T. Supuran. (2014) Sulfonamide inhibition studies of the β carbonic anhydrase from Drosophila melanogaster. Bioorganic & Medicinal Chemistry Letters 24:13, pages 2797-2801.
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Mostafa M. Ghorab, Mansour S. Alsaid, Mariangela Ceruso, Yassin M. Nissan & Claudiu T. Supuran. (2014) Carbonic anhydrase inhibitors: Synthesis, molecular docking, cytotoxic and inhibition of the human carbonic anhydrase isoforms I, II, IX, XII with novel benzenesulfonamides incorporating pyrrole, pyrrolopyrimidine and fused pyrrolopyrimidine moieties. Bioorganic & Medicinal Chemistry 22:14, pages 3684-3695.
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Isao Nishimori, Daniela Vullo, Tomoko Minakuchi, Andrea Scozzafava, Sameh M. Osman, Zeid AlOthman, Clemente Capasso & Claudiu T. Supuran. (2014) Anion inhibition studies of two new β-carbonic anhydrases from the bacterial pathogen Legionella pneumophila. Bioorganic & Medicinal Chemistry Letters 24:4, pages 1127-1132.
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Andrea Scozzafava & Claudiu T. Supuran. 2014. Carbonic Anhydrase: Mechanism, Regulation, Links to Disease, and Industrial Applications. Carbonic Anhydrase: Mechanism, Regulation, Links to Disease, and Industrial Applications 349 359 .
Robert McKenna & Claudiu T. Supuran. 2014. Carbonic Anhydrase: Mechanism, Regulation, Links to Disease, and Industrial Applications. Carbonic Anhydrase: Mechanism, Regulation, Links to Disease, and Industrial Applications 291 323 .
Daniela Vullo, R. Siva Sai Kumar, Andrea Scozzafava, Clemente Capasso, James G. Ferry & Claudiu T. Supuran. (2013) Anion inhibition studies of a β-carbonic anhydrase from Clostridium perfringens. Bioorganic & Medicinal Chemistry Letters 23:24, pages 6706-6710.
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Janis Leitans, Agnese Sprudza, Muhammet Tanc, Igor Vozny, Raivis Zalubovskis, Kaspars Tars & Claudiu T. Supuran. (2013) 5-Substituted-(1,2,3-triazol-4-yl)thiophene-2-sulfonamides strongly inhibit human carbonic anhydrases I, II, IX and XII: Solution and X-ray crystallographic studies. Bioorganic & Medicinal Chemistry 21:17, pages 5130-5138.
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Peiwen Pan, Alane Beatriz Vermelho, Andrea Scozzafava, Seppo Parkkila, Clemente Capasso & Claudiu T. Supuran. (2013) Anion inhibition studies of the α-carbonic anhydrase from the protozoan pathogen Trypanosoma cruzi, the causative agent of Chagas disease. Bioorganic & Medicinal Chemistry 21:15, pages 4472-4476.
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Muhammet Tanc, Fabrizio Carta, Murat Bozdag, Andrea Scozzafava & Claudiu T. Supuran. (2013) 7-Substituted-sulfocoumarins are isoform-selective, potent carbonic anhydrase II inhibitors. Bioorganic & Medicinal Chemistry 21:15, pages 4502-4510.
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Fabrizio Carta, Atilla Akdemir, Andrea Scozzafava, Emanuela Masini & Claudiu T. Supuran. (2013) Xanthates and Trithiocarbonates Strongly Inhibit Carbonic Anhydrases and Show Antiglaucoma Effects in Vivo. Journal of Medicinal Chemistry 56:11, pages 4691-4700.
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Daniela Vullo, Worraanong Leewattanapasuk, Fritz A. Mühlschlegel, Antonio Mastrolorenzo, Clemente Capasso & Claudiu T. Supuran. (2013) Carbonic anhydrase inhibitors: Inhibition of the β-class enzyme from the pathogenic yeast Candida glabrata with sulfonamides, sulfamates and sulfamides. Bioorganic & Medicinal Chemistry Letters 23:9, pages 2647-2652.
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Peiwen Pan, Alane Beatriz Vermelho, Giseli Capaci Rodrigues, Andrea Scozzafava, Martti E. E. Tolvanen, Seppo Parkkila, Clemente Capasso & Claudiu T. Supuran. (2013) Cloning, Characterization, and Sulfonamide and Thiol Inhibition Studies of an α-Carbonic Anhydrase from Trypanosoma cruzi , the Causative Agent of Chagas Disease . Journal of Medicinal Chemistry 56:4, pages 1761-1771.
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Daniela Vullo, Viviana De Luca, Andrea Scozzafava, Vincenzo Carginale, Mosè Rossi, Claudiu T. Supuran & Clemente Capasso. (2012) Anion inhibition studies of the fastest carbonic anhydrase (CA) known, the extremo-CA from the bacterium Sulfurihydrogenibium azorense. Bioorganic & Medicinal Chemistry Letters 22:23, pages 7142-7145.
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Giuseppina De Simone & Claudiu T. Supuran. (2012) (In)organic anions as carbonic anhydrase inhibitors. Journal of Inorganic Biochemistry 111, pages 117-129.
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