Keywords: 4 (4 Acetamidophenylsulfonamido)benzoic Acid, 4 (4 Aminophenylsulfonamido)benzoic Acid, 4 [4 (sulfamoylamino)phenylsulfonamido] N (4 Sulfamoylphenethyl)benzamide, Acetazolamide, Carbonate Dehydratase Ii, Carbonate Dehydratase Inhibitor, Diclofenamide, Ethoxzolamide, N Sulfamoyl 4 Aminobenzene Sulfonamide, Sulfanilamide, Unclassified Drug, Zinc Ion, Article, Controlled Study, Drug Potency, Drug Protein Binding, Drug Structure, Enzyme Active Site, Structure Analysis, X Ray Crystallography, Carbonic Anhydrase Inhibitors, X-Ray, Enzyme Assays, Humans, Isoenzymes, Models, Molecular, Protein Conformation, Structure-Activity Relationship, 4 (4 Acetamidophenylsulfonamido) Benzoic Acid, 4 (4 Aminophenylsulfonamido) Benzoic Acid, 4 [4 (sulfamoylamino) Phenylsulfonamido] N (4 Sulfamoylphenethyl) Benzamide,
Affiliations: *** IBB - CNR ***
Istituto di Biostrutture e Bioimmagini-CNR, via Mezzocannone 16, 80134 Napoli, Italy
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, CNRS-UM1-UM2, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex, France
Universitaè Degli Studi di Firenze, Laboratorio di Chimica Bioinorganica, Via della Lastruccia 3, I-50019 Sesto Fiorentino (Firenze), Italy
Universita Degli Studi di Firenze, Laboratorio di Chimica Bioinorganica, Via della Lastruccia 3, I-50019 Sesto Fiorentino (Firenze), Italy
References: Alterio, V., Di Fiore, A., D'Ambrosio, K., Supuran, C.T., De Simone, G., Multiple Binding Modes of Inhibitors to Carbonic Anhydrases: How to Design Specific Drugs Targeting 15 Different Isoforms? (2012) Chem. Rev., 112. , DOI: 10.1021/cr200176
Supuran, C.T., Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators (2008) Nat. Rev. Drug Discovery, 7, pp. 168-181
MacK, E.T., Snyder, P.W., Perez-Castillejos, R., Bilgicer, B., Moustakas, D.T., Butte, M.J., Whitesides, G.M., Dependence of Avidity on Linker Length for a Bivalent Ligand-Bivalent Receptor Model System (2012) J. Am. Chem. Soc., 134, pp. 333-345
Winum, J.Y., Vullo, D., Casini, A., Montero, J.L., Scozzafava, A., Supuran, C.T., Carbonic anhydrase inhibitors. Inhibition of cytosolic isozymes i and II and transmembrane, tumor-associated isozyme IX with sulfamates including EMATE also acting as steroid sulfatase inhibitors (2003) J. Med. Chem., 46, pp. 2197-2204
Abbate, F., Winum, J.Y., Potter, B.V., Casini, A., Montero, J.L., Scozzafava, A., Supuran, C.T., Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with EMATE, a dual inhibitor of carbonic anhydrases and steroid sulfatase (2004) Bioorg. Med. Chem. Lett., 14, pp. 231-234
Winum, J.Y., Scozzafava, A., Montero, J.L., Supuran, C.T., Design of zinc binding functions for carbonic anhydrase inhibitors (2008) Curr. Pharm. Des., 14, pp. 615-621
Supuran, C.T., Diuretics: From classical carbonic anhydrase inhibitors to novel applications of the sulfonamides (2008) Curr. Pharm. Des., 14, pp. 641-648
Mincione, F., Scozzafava, A., Supuran, C.T., (2009) Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications, pp. 139-154. , Supuran, C. T. Winum, J. Y. Wiley: Hoboken
Thiry, A., Dogneè, J.M., Masereel, B., Supuran, C.T., Carbonic Anhydrase Inhibitors as Anticonvulsant Agents (2007) Curr. Top. Med. Chem., 7, pp. 855-864
De Simone, G., Di Fiore, A., Supuran, C.T., Are carbonic anhydrase inhibitors suitable for obtaining antiobesity drugs? (2008) Curr. Pharm. Des., 14, pp. 655-660
Dubois, L., Lieuwes, N.G., Maresca, A., Thiry, A., Supuran, C.T., Scozzafava, A., Wouters, B.G., Lambin, P., Imaging of CA IX with fluorescent labelled sulfonamides distinguishes hypoxic and (re)-oxygenated cells in a xenograft tumour model (2009) Radiother. Oncol., 92, pp. 423-428
Ahlskog, J.K., Dumelin, C.E., Trüssel, S., Marlind, J., Neri, D., In vivo targeting of tumor-associated carbonic anhydrases using acetazolamide derivatives (2009) Bioorg. Med. Chem. Lett., 19, pp. 4851-4856
Buller, F., Steiner, M., Frey, K., Mircsof, D., Scheuermann, J., Kalisch, M., Bühlmann, P., Neri, D., Selection of Carbonic Anhydrase IX Inhibitors from One Million DNA-Encoded Compounds (2011) ACS Chem. Biol., 6, pp. 336-344
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Abbate, F., Supuran, C.T., Scozzafava, A., Orioli, P., Stubbs, M.T., Klebe, G., Nonaromatic sulfonamide group as an ideal anchor for potent human carbonic anhydrase inhibitors: Role of hydrogen-bonding networks in ligand binding and drug design (2002) J. Med. Chem., 45, pp. 3583-3587
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Thiry, A., Dogné, J.M., Supuran, C.T., Masereel, B., Anticonvulsant sulfonamides/sulfamates/sulfamides with carbonic anhydrase inhibitory activity: Drug design and mechanism of action (2008) Curr. Pharm. Des., 14, pp. 661-671
Cecchi, A., Winum, J.Y., Innocenti, A., Vullo, D., Montero, J.L., Scozzafava, A., Supuran, C.T., Carbonic anhydrase inhibitors: Synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides derived from 4-isothiocyanato-benzolamide (2004) Bioorg. Med. Chem. Lett., 14, pp. 5775-5780
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Casini, A., Winum, J.Y., Montero, J.L., Scozzafava, A., Supuran, C.T., Carbonic anhydrase inhibitors: Inhibition of cytosolic isozymes i and II with sulfamide derivatives (2003) Bioorg. Med. Chem. Lett., 13, pp. 837-840
Supuran, C.T., Clare, B.W., Carbonic anhydrase inhibitors. Part 24. A quantitative structure-activity study of positively-charged sulfonamide inhibitors (1995) Eur. J. Med. Chem., 30, pp. 687-696
Eriksson, A.E., Jones, T.A., Liljas, A., Refined structure of human carbonic anhydrase II at 2.0 Å resolution (1988) Proteins, 4, pp. 274-282
Khalifah, R.G., The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C (1971) J. Biol. Chem., 246, pp. 2561-2573
Pocker, Y., Stone, J.T., The catalytic versatility of erythrocyte carbonic anhydrase. III. Kinetic studies of the enzyme-catalyzed hydrolysis of p-nitrophenyl acetate (1967) Biochemistry, 6, pp. 668-678
Innocenti, A., Supuran, C.T., Paraoxon, 4-nitrophenyl phosphate and acetate are substrates of α- But not of β-, γ- And ζ-carbonic anhydrases (2010) Bioorg. Med. Chem. Lett., 20, pp. 6208-6212
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Okada, M., Iwashita, S., Koizumi, N., Efficient general method for sulfamoylation of a hydroxyl group (2000) Tetrahedron Lett., 41, pp. 7047-7051
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Brunger, A.T., Adams, P.D., Clore, G.M., De Lano, W.L., Gros, P., Grosse-Kunstleve, R.W., Jiang, J.S., Warren, G.L., Crystallography & NMR system: A new software suite for macromolecular structure determination (1998) Acta Crystallogr., Sect. D, 54, pp. 905-921
Jones, T.A., Zou, J.Y., Cowan, S.W., Kjeldgaard, M., Improved methods for building protein models in electron density maps and the location of errors in these models (1991) Acta Crystallogr., Sect. A, 47, pp. 110-119
Laskowski, R.A., MacArthur, M.W., Moss, D.S., Thornton, J.M., PROCHECK: A program to check the stereochemical quality of protein structures (1993) J. Appl. Crystallogr., 26, pp. 283-291
Supuran, C. T., Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators (2008) Nat. Rev. Drug Discovery, 7, pp. 168-181
MacK, E. T., Snyder, P. W., Perez-Castillejos, R., Bilgicer, B., Moustakas, D. T., Butte, M. J., Whitesides, G. M., Dependence of Avidity on Linker Length for a Bivalent Ligand-Bivalent Receptor Model System (2012) J. Am. Chem. Soc., 134, pp. 333-345
Winum, J. Y., Vullo, D., Casini, A., Montero, J. L., Scozzafava, A., Supuran, C. T., Carbonic anhydrase inhibitors. Inhibition of cytosolic isozymes i and II and transmembrane, tumor-associated isozyme IX with sulfamates including EMATE also acting as steroid sulfatase inhibitors (2003) J. Med. Chem., 46, pp. 2197-2204
Winum, J. Y., Scozzafava, A., Montero, J. L., Supuran, C. T., Design of zinc binding functions for carbonic anhydrase inhibitors (2008) Curr. Pharm. Des., 14, pp. 615-621
Supuran, C. T., Diuretics: From classical carbonic anhydrase inhibitors to novel applications of the sulfonamides (2008) Curr. Pharm. Des., 14, pp. 641-648
Thiry, A., Dogne, J. M., Masereel, B., Supuran, C. T., Carbonic Anhydrase Inhibitors as Anticonvulsant Agents (2007) Curr. Top. Med. Chem., 7, pp. 855-864
Ahlskog, J. K., Dumelin, C. E., Tr ssel, S., Marlind, J., Neri, D., In vivo targeting of tumor-associated carbonic anhydrases using acetazolamide derivatives (2009) Bioorg. Med. Chem. Lett., 19, pp. 4851-4856
Supuran, C. T., Di Fiore, A., De Simone, G., Carbonic anhydrase inhibitors as emerging drugs for the treatment of obesity (2008) Expert Opin. Emerging Drugs, 13, pp. 383-392
Thiry, A., Dogn, J. M., Supuran, C. T., Masereel, B., Anticonvulsant sulfonamides/sulfamates/sulfamides with carbonic anhydrase inhibitory activity: Drug design and mechanism of action (2008) Curr. Pharm. Des., 14, pp. 661-671
Supuran, C. T., Clare, B. W., Carbonic anhydrase inhibitors. Part 24. A quantitative structure-activity study of positively-charged sulfonamide inhibitors (1995) Eur. J. Med. Chem., 30, pp. 687-696
Eriksson, A. E., Jones, T. A., Liljas, A., Refined structure of human carbonic anhydrase II at 2. 0 resolution (1988) Proteins, 4, pp. 274-282
Khalifah, R. G., The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C (1971) J. Biol. Chem., 246, pp. 2561-2573
Brunger, A. T., Adams, P. D., Clore, G. M., De Lano, W. L., Gros, P., Grosse-Kunstleve, R. W., Jiang, J. S., Warren, G. L., Crystallography & NMR system: A new software suite for macromolecular structure determination (1998) Acta Crystallogr., Sect. D, 54, pp. 905-921
Jones, T. A., Zou, J. Y., Cowan, S. W., Kjeldgaard, M., Improved methods for building protein models in electron density maps and the location of errors in these models (1991) Acta Crystallogr., Sect. A, 47, pp. 110-119
Laskowski, R. A., MacArthur, M. W., Moss, D. S., Thornton, J. M., PROCHECK: A program to check the stereochemical quality of protein structures (1993) J. Appl. Crystallogr., 26, pp. 283-291
Development of potent carbonic anhydrase inhibitors incorporating both sulfonamide and sulfamide groups