Carbonic anhydrase inhibitors. N-Cyanomethylsulfonamides—a new zinc binding group in the design of inhibitors targeting cytosolic and membrane-anchored isoforms

References

• Supuran CT, Scozzafava A, Conway J. Carbonic anhydrase—its inhibitors and activators, HJ Smith, C Simons, Series. CRC Press, Boca Raton, New York, London 2004; 1–363
   Google Scholar
• Pastorekova S, Parkkila S, Pastorek J, Supuran CT. Carbonic anhydrases: Current state of the art, therapeutic applications and future prospects. J Enz Inhib Med Chem 2004; 19: 199–229
   PubMed Web of Science ®Google Scholar
• Supuran CT, Scozzafava A, Casini A. Carbonic anhydrase inhibitors. Med Res Rev 2003; 23: 146–189
   PubMed Web of Science ®Google Scholar
• Scozzafava A, Mastrolorenzo A, Supuran CT. Modulation of carbonic anhydrase activity and its applications in therapy. Expert Opin Ther Pat 2004; 14: 667–702
   Web of Science ®Google Scholar
• Sly WS, Hu PY. Human carbonic anhydrases and carbonic anhydrase deficiencies. Annu Rev Biochem 1995; 64: 375–401
   PubMed Web of Science ®Google Scholar
• Lehtonen J, Shen B, Vihinen M, Casini A, Scozzafava A, Supuran CT, Parkkila AK, Saarnio J, Kivela AJ, Waheed A, Sly WS, Parkkila S. Characterization of CA XIII, a novel member of the carbonic anhydrase isozyme family. Biol Chem 2004; 279: 2719–2727
   Google Scholar
• Fujikawa-Adachi K, Nishimori I, Taguchi T, Onishi S. Human mitochondrial carbonic anhydrase VB. CDNA cloning, mRNA expression, subcellular localization, and mapping to chromosome X. J Biol Chem 1999; 274: 21228–21233
   PubMed Web of Science ®Google Scholar
• Fujikawa-Adachi K, Nishimori I, Taguchi T, Onishi S. Human carbonic anhydrase XIV (CA14): cDNA cloning, mRNA expression, and mapping to chromosome 1. Genomics 1999; 61: 74–81
   PubMed Web of Science ®Google Scholar
• Nishimori I, Vullo D, Innocenti A, Scozzafava A, Mastrolorenzo A, Supuran CT. Carbonic anhydrase inhibitors. The mitochondrial isozyme VB as a new target for sulfonamide and sulfamate inhibitors. J Med Chem 2005; 48: 7860–7866
   PubMed Web of Science ®Google Scholar
• Pastorekova S, Casini A, Scozzafava A, Vullo D, Pastorek J, Supuran CT. Carbonic anhydrase inhibitors: The first selective, membrane-impermeant inhibitors targeting the tumor-associated isozyme IX. Bioorg Med Chem Lett 2004; 14: 869–873
   PubMed Web of Science ®Google Scholar
• Vullo D, Voipio J, Innocenti A, Rivera C, Ranki H, Scozzafava A, Kaila K, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of the human cytosolic isozyme VII with aromatic and heterocyclic sulfonamides. Bioorg Med Chem Lett 2005; 15: 971–976
   PubMed Web of Science ®Google Scholar
• Vullo D, Innocenti A, Nishimori I, Pastorek J, Scozzafava A, Pastorekova S, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides—a new target for the design of antitumor and antiglaucoma drugs?. Bioorg Med Chem Lett 2005; 15: 963–969
   PubMed Web of Science ®Google Scholar
• Cecchi A, Hulikova A, Pastorek J, Pastorekova S, Scozzafava A, Winum J-Y, Montero J-L, Supuran CT. Carbonic anhydrase inhibitors. Sulfonamides inhibit isozyme IX mediated acidification of hypoxic tumors. Fluorescent sulfonamides design as probes of membrane-bound carbonic anhydrase isozymes involvement in tumorigenesis. J Med Chem 2005; 48: 4834–4841
   PubMed Web of Science ®Google Scholar
• Krungkrai J, Scozzafava A, Reungprapavut S, Krungkrai SR, Rattanajak R, Kamchonwongpaisan S, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of Plasmodium falciparum carbonic anhydrase with aromatic sulfonamides: Towards antimalarials with a novel mechanism of action?. Bioorg Med Chem 2005; 13: 483–489
   PubMed Web of Science ®Google Scholar
• Suarez Covarrubias A, Larsson AM, Hogbom M, Lindberg J, Bergfors T, Bjorkelid C, Mowbray SL, Unge T, Jones TA. Structure and function of carbonic anhydrases from Mycobacterium tuberculosis. J Biol Chem 2005; 280: 18782–18789
   PubMed Web of Science ®Google Scholar
• Klengel T, Liang WJ, Chaloupka J, Ruoff C, Schroppel K, Naglik JR, Eckert SE, Mogensen EG, Haynes K, Tuite MF, Levin LR, Buck J, Muhlschlegel FA. Fungal adenylyl cyclase integrates CO2 sensing with cAMP signaling and virulence. Curr Biol 2005; 15: 2021–2026
   PubMed Web of Science ®Google Scholar
• Bahn YS, Cox GM, Perfect JR, Heitman J. Carbonic anhydrase and CO2 sensing during Cryptococcus neoformans growth, differentiation, and virulence. Curr Biol 2005; 15: 2013–2020
   PubMed Web of Science ®Google Scholar
• Briganti F, Pierattelli R, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. Part 37. Novel classes of carbonic anhydrase inhibitors and their interaction with the native and cobalt-substituted enzyme: Kinetic and spectroscopic investigations. Eur J Med Chem 1996; 31: 1001–1010
   Web of Science ®Google Scholar
• Winum JY, Scozzafava A, Montero JL, Supuran CT. Sulfamates and their therapeutic potential. Med Res Rev 2005; 25: 186–228
   PubMed Web of Science ®Google Scholar
• Bonnac L, Innocenti A, Winum JY, Casini A, Montero JL, Scozzafava A, Barragan V, Supuran CT. Carbonic anhydrase inhibitors: Aliphatic N-phosphorylated sulfamates—a novel zinc-anchoring group leading to nanomolar inhibitors. J Enz Inhib Med Chem 2004; 19: 275–278
   PubMed Web of Science ®Google Scholar
• Casini A, Winum JY, Montero JL, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: Inhibition of cytosolic isozymes I and II with sulfamide derivatives. Bioorg Med Chem Lett 2003; 13: 837–840
   PubMed Web of Science ®Google Scholar
• Winum JY, Scozzafava A, Montero JL, Supuran CT. The sulfamide motif in the design of enzyme inhibitors. Expert Opin Ther Pat 2006; 16: 27–47
   PubMed Web of Science ®Google Scholar
• Winum J-Y, Innocenti A, Nasr J, Montero J-L, Scozzafava A, Vullo D, Supuran CT. Carbonic anhydrase inhibitors: Synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, IX and XII with N-hydroxy-sulfamides—A new zinc binding function in the design of inhibitors. Biorg Med Chem Lett 2005; 15: 2353–2358
   PubMed Web of Science ®Google Scholar
• Supuran CT, Scozzafava A, Briganti F. Carbonic anhydrase inhibitors. N-Cyanosulfonamides: a new class of high affinity isozyme II and IV inhibitors. J Enz Inhib 1999; 14: 289–306
   Google Scholar
• Khalifah RG. The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C. J Biol Chem 1971; 246: 2561–2573
   PubMed Web of Science ®Google Scholar
• Vullo D, Franchi M, Gallori E, Pastorek J, Scozzafava A, Pastorekova S, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of the tumor-associated isozyme IX with aromatic and heterocyclic sulfonamides. Bioorg Med Chem Lett 2003; 13: 1005–1009
   PubMed Web of Science ®Google Scholar