Carbonic anhydrase inhibitors. Biphenylsulfonamides with inhibitory action towards the transmembrane, tumor-associated isozymes IX possess cytotoxic activity against human colon, lung and breast cancer cell lines

References

• CT Supuran. (2008). Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators. Nature Rev Drug Discov 7:168–181.
   PubMed Web of Science ®Google Scholar
• A Scozzafava, A Mastrolorenzo, and CT Supuran. (2006). Carbonic anhydrase inhibitors and activators and their use in therapy. Expert Opin Therap Pat 16:1627–1664.
   Web of Science ®Google Scholar
• CT Supuran, A Scozzafava, and A Casini. (2003). Carbonic anhydrase inhibitors. Med Res Rev 23:146–189.
   PubMed Web of Science ®Google Scholar
• CT Supuran. (2008). Carbonic anhydrases–an overview. Curr Pharm Des 14:603–614.
   PubMed Web of Science ®Google Scholar
• F Mincione, A Scozzafava, and CT Supuran. (2008). The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents. Curr Pharm Des 14:649–654.
   PubMed Web of Science ®Google Scholar
• G De Simone, and CT Supuran. (2007). Antiobesity carbonic anhydrase inhibitors. Curr Top Med Chem 7:879–884.
   PubMed Web of Science ®Google Scholar
• A Thiry, JM Dogné, CT Supuran, and B Masereel. (2008). Anticonvulsant sulfonamides/sulfamates/ sulfamides with carbonic anhydrase inhibitory activity: Drug design and mechanism of action. Curr Pharm Des 14:661–671.
   PubMed Web of Science ®Google Scholar
• A Thiry, JM Dogné, B Masereel, and CT Supuran. (2006). Targeting tumor-associated carbonic anhydrase IX in cancer therapy. Trends Pharmacol Sci 27:566–573.
   PubMed Web of Science ®Google Scholar
• E Švastová, A Hulíková, M Rafajová, M Zatovicová, A Gibadulinová, A Casini, A Cecchi, A Scozzafava, CT Supuran, J Pastorek, and S Pastoreková. (2004). Hypoxia activates the capacity of tumor-associated carbonic anhydrase IX to acidify extracellular pH. EBS Lett 577:439–445.
   PubMed Web of Science ®Google Scholar
• A Cecchi, and CT Supuran. (2008). Fluorescence- and spin-labeled carbonic anhydrase inhibitors. Curr Pharm Des 14:99–707.
   Google Scholar
• L Dubois, K Douma, CT Supuran, RK Chiu, MA van Zandvoort, S Pastoreková, A Scozzafava, BG Wouters, and P Lambin. (2007). Imaging the hypoxia surrogate marker CA IX requires expression and catalytic activity for binding fluorescent sulfonamide inhibitors. Radiother Oncol 83:367–373.
   PubMed Web of Science ®Google Scholar
• V Alterio, RM Vitale, SM Monti, C Pedone, A Scozzafava, A Cecchi, G De Simone, and CT Supuran. (2006). Carbonic anhydrase inhibitors: X-ray and molecular modeling study for the interaction of a fluorescent antitumor sulfonamide with isozyme II and IX. J Am Chem Soc 128:8329–8335.
   PubMed Web of Science ®Google Scholar
• J Krungkrai, and CT Supuran. (2008). The alpha-carbonic anhydrase from the malaria parasite and its inhibition. Curr Pharm Des 14:631–640.
   PubMed Web of Science ®Google Scholar
• I Nishimori, S Onishi, H Takeuchi, and CT Supuran. (2008). The alpha and beta classes carbonic anhydrases from Helicobacter pylori as novel drug targets. Curr Pharm Des 14:622–630.
   PubMed Web of Science ®Google Scholar
• T Klengel, WJ Liang, J Chaloupka, C Ruoff, K Schröppel, JR Naglik, SE Eckert, EG Mogensen, K Haynes, MF Tuite, LR Levin, J Buck, and FA Mühlschlegel. (2005). Fungal adenylyl cyclase integrates CO2 sensing with cAMP signaling and virulence. Curr Biol 15:2021–2026.
   PubMed Web of Science ®Google Scholar
• EG Mogensen, G Janbon, J Chaloupka, C Steegborn, MS Fu, F Moyrand, T Klengel, DS Pearson, MA Geeves, J Buck, LR Levin, and FA Mühlschlegel. (2006). Cryptococcus neoformans senses CO2 through the carbonic anhydrase Can2 and the adenylyl cyclase Cac1. Eukaryot Cell 5:103–111.
   PubMed Web of Science ®Google Scholar
• YS Bahn, and FA Muhlschlegel. (2006). CO2 sensing in fungi and beyond. Curr Opin Microbiol 9:572–578.
   PubMed Web of Science ®Google Scholar
• AS Covarrubias, T Bergfors, TA Jones, and M Högbom. (2006). Structural mechanics of the pH-dependent activity of beta-carbonic anhydrase from Mycobacterium tuberculosis. J Biol Chem 281:4993–4999.
   PubMed Web of Science ®Google Scholar
• G De Simone, A Di Fiore, V Menchise, C Pedone, J Antel, A Casini, A Scozzafava, M Wurl, and CT Supuran. (2005). Carbonic anhydrase inhibitors. Zonisamide is an effective inhibitor of the cytosolic isozyme II and mitochondrial isozyme V: Solution and X-ray crystallographic studies. Bioorg Med Chem Lett 15:2315–2320.
   PubMed Web of Science ®Google Scholar
• JY Winum, C Temperini, K El Cheikh, A Innocenti, D Vullo, S Ciattini, JL Montero, A Scozzafava, and CT Supuran. (2006). Carbonic anhydrase inhibitors: Clash with Ala65 as a means for designing inhibitors with low affinity for the ubiquitous isozyme II, exemplified by the crystal structure of the topiramate sulfamide analogue. J Med Chem 49:7024–7031.
   PubMed Web of Science ®Google Scholar
• J Antel, A Weber, CA Sotriffer, and G Klebe. Multiple binding modes observed in X-ray structures of carbonic anhydrase inhibitor complexes and other systems: Consequences for structure-based drug design. In: CT Supuran, A Scozzafava, and J Conway, editors. Carbonic anhydrase–Its inhibitors and activators. Boca Raton: CRC Press; (2004). p 45–65.
   Google Scholar
• C Temperini, A Cecchi, A Scozzafava, and CT Supuran. (2008). Carbonic anhydrase inhibitors. Interaction of indapamide and related diuretics with 12 mammalian isozymes and X-ray crystallographic studies for the indapamide-isozyme II adduct. Bioorg Med Chem Lett 18:2567–2573.
   PubMed Web of Science ®Google Scholar
• A Di Fiore, C Pedone, J Antel, H Waldeck, A Witte, M Wurl, A Scozzafava, CT Supuran, and G De Simone. (2008). Carbonic anhydrase inhibitors: The X-ray crystal structure of ethoxzolamide complexed to human isoform II reveals the importance of thr200 and gln92 for obtaining tight-binding inhibitors. Bioorg Med Chem Lett 18:2669–2674.
   PubMed Web of Science ®Google Scholar
• C Temperini, A Cecchi, NA Boyle, A Scozzafava, JE Cabeza, P WentworthJr, GM Blackburn, and CT Supuran. (2008). Carbonic anhydrase inhibitors. Interaction of 2-N,N-dimethylamino-1,3,4-thiadiazole-5-methanesulfonamide with 12 mammalian isoforms: Kinetic and X-ray crystallographic studies. Bioorg Med Chem Lett 18:999–1005.
   PubMed Web of Science ®Google Scholar
• CT Supuran, A Scozzafava, and A Casini. Development of sulfonamide carbonic anhydrase inhibitors. In: CT Supuran, A Scozzafava, and J Conway, editors. Carbonic anhydrase–Its inhibitors and activators. Boca Raton: CRC Press; (2004). p 67–147.
   Google Scholar
• A Badawi, A El-Maghraby, B Haroun, and H Soliman. (1980). Synthesis of biphenylsulfonamides. Pharmazie 35:748–753.
   PubMed Web of Science ®Google Scholar
• CT Supuran, MA Ilies, and A Scozzafava. (1998). Carbonic anhydrase inhibitors. Part 29. Interaction of isozymes I, II and IV with benzolamide-like derivatives. Eur J Med Chem 33:739–752.
   Web of Science ®Google Scholar
• RG Khalifah. (1971). The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C. J Biol Chem 246:2561–2573.
   PubMed Web of Science ®Google Scholar
• BA Teicher. Anticancer drug development guide: Preclinical screening, clinical trials, and approval. Totowa, NJ: Humana Press Inc.; (1997). p 7–125.
   Google Scholar
• CT Supuran, and A Scozzafava. (2000). Carbonic anhydrase inhibitors - Part 94. 1,3,4-Thiadiazole-2-sulfonamide derivatives as antitumor agents ?. Eur J Med Chem 35:867–874.
   PubMed Web of Science ®Google Scholar
• CT Supuran, and A Scozzafava. (2000). Carbonic anhydrase inhibitors: Aromatic sulfonamides and disulfonamides act as efficient tumor growth inhibitors. J Enz Inhib 15:597–610.
   Google Scholar