Carbonic anhydrase inhibitors: Stacking with Phe131 determines active site binding region of inhibitors as exemplified by the X-ray crystal structure of a membrane-impermeant antitumor sulfonamide complexed with isozyme II (478 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2005 Sep 8; 48(18): 5721-5727.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 4.926, 5-year impact factor: 5.504
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-24744467784&partnerID=40&md5=1c4ee242723e3de5189fb90a3acd55d9
Keywords: 1 N (4 Sulfamoylphenylethyl) 2, 6 Trimethylpyridinium Perchlorate, Carbonate Dehydratase Ii, Carbonate Dehydratase Inhibitor, Carbonate Dehydratase Xii, Glutamine, Isoenzyme, Leucine, Phenylalanine, Sulfonamide, Threonine, Unclassified Drug, Valine, Amino Acid Sequence, Antineoplastic Activity, Article, Complex Formation, Crystal Structure, Drug Binding Site, Drug Structure, Hydrophilicity, Hydrophobicity, Protein Expression, Protein Targeting, Structure Analysis, X Ray Crystallography, Antigens, Antineoplastic Agents, Carbonic Anhydrase Ii, Cell Membrane Permeability, X-Ray, Humans, Models, Molecular, Molecular Structure, Protein Binding, Pyridinium Compounds, Quantitative Structure-Activity Relationship, Recombinant Proteins, Tumor Markers, Biological,
Affiliations:
*** IBB - CNR ***
Istituto di Biostrutture e Bioimmagini, CNR, via Mezzocannone 16, 80134 Naples, Italy
Bioindustry Park del Canavese Spa, Via Ribes 5, 10010 Colleretto Giacosa (Torino), Italy
Dipartimento delle Scienze Biologiche, Sezione Biostrutture, University of Naples Federico II, via Mezzocannone 16, 80134 Naples, Italy
Università degli Studi di Firenze, Polo Scientifico, Laboratorio di Chimica Bioinorganica, Via della Lastruccia 3, 50019 Sesto Fiorentino (Florence), Italy
Universit degli Studi di Firenze, Polo Scientifico, Laboratorio di Chimica Bioinorganica, Via della Lastruccia 3, 50019 Sesto Fiorentino (Florence), Italy
References:
Supuran, C.T., Scozzafava, A., Conway, J., (2004) Carbonic Anhydrase - Its Inhibitors and Activators, pp. 1-363. , CRC Press: Boca Rato
Scozzafava, A., Mastrolorenzo, A., Supuran, C.T., Modulation of carbonic anhydrase activity and its applications in therapy (2004) Expert Opin. Ther. Pat., 14, pp. 667-702
Pastorekova, S., Parkkila, S., Pastorek, J., Supuran, C.T., Carbonic anhydrases: Current state of the art, therapeutic applications and future prospects (2004) J. Enzyme. Inhib. Med. Chem., 19, pp. 199-229
Marquis, R.E., Whitson, J.T., Management of glaucoma: Focus on pharmacological therapy (2005) Drugs Aging, 22, pp. 1-21
Vullo, D., Innocenti, A., Nishimori, I., Pastorek, J., Scozzafava, A., Pastorekova, S., Supuran, C.T., Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides - A new target for the design of antitumor and antiglaucoma drugs? (2005) Bioorg. Med. Chem. Lett., 15, pp. 963-969
Supuran, C.T., Casini, A., Scozzafava, A., Development of sulfonamide carbonic anhydrase inhibitors (CAIs) (2004) Carbonic Anhydrase - Its Inhibitors and Activators, pp. 67-148. , Supuran, C. T., Scozzafava, A., Conway, J.
Eds., CRC Press: Boca Raton (FL), USA
Loiselle, F.B., Morgan, P.E., Alvarez, B.V., Casey, J.R., Regulation of the human NBC3 Na+/HCO3- Cotransporter by carbonic anhydrase II and PKA (2004) Am. J. Physiol. Cell Physiol., 286, pp. C1423-C1433
Rivera, C., Voipio, J., Kaila, K., Two developmental switches in GABAergic signalling: The K+-Cl- Cotransporter KCC2 and carbonic anhydrase CAVII (2005) J. Physiol., 562, pp. 27-36
Vullo, D., Voipio, J., Innocenti, A., Rivera, C., Ranki, H., Scozzafava, A., Kaila, K., Supuran, C.T., Carbonic anhydrase inhibitors. Inhibition of the human cytosolic isozyme VII with aromatic and heterocyclic sulfonamides (2005) Bioorg. Med. Chem. Lett., 15, pp. 971-976
Lyons, K.E., Pahwa, R., Cornelia, C.L., Eisa, M.S., Elble, R.J., Fahn, S., Jankovic, J., Watts, R.L., Benefits and risks of pharmacological treatments for essential tremor (2003) Drug Saf., 26, pp. 461-481
Garske, L.A., Brown, M.G., Morrison, S.C., Acetazolamide reduces exercise capacity and increases leg fatigue under hypoxic conditions (2003) J. Appl. Physiol., 94, pp. 991-996
Hori, K., Ishida, S., Inoue, M., Shinoda, K., Kawashima, S., Kitamura, S., Oguchi, Y., Treatment of cystoid macular edema with oral acetazolamide in a patient with best vitelliform macular dystrophy (2004) Retina, 24, pp. 481-482
Winum, J.Y., Scozzafava, A., Montera, J.L., Supuran, C.T., Sulfamates and their therapeutic potential (2005) Med. Res. Rev., 25, pp. 186-228
Svastova, E., Hulikova, A., Rafajova, M., Zat'ovicova, M., Gibadulinova, A., Casini, A., Cecchi, A., Pastorekova, S., Hypoxia activates the capacity of tumor-associated carbonic anhydrase IX to acidify extracellular pH (2004) FEBS Lett., 577, pp. 439-445
Pastorek, J., Pastorekova, S., Callebaut, I., Mornon, J.P., Zelnik, V., Opavsky, R., Zat'ovicova, M., Stanbridge, E.J., Cloning and characterization of MN, a human tumor-associated protein with a domain homologous to carbonic anhydrase and a putative helix-loop-helix DNA binding segment (1994) Oncogene, 9, pp. 2877-2888
Rafajova, M., Zatovicova, M., Kettmann, R., Pastorek, J., Pastorekova, S., Induction by hypoxia combined with low glucose or low bicarbonate and high posttranslational stability upon reoxygenation contribute to carbonic anhydrase IX expression in cancer cells (2004) Int. J. Oncol., 24, pp. 995-1004
Ivanov, S., Liao, S.Y., Ivanova, A., Danilkovitch-Miagkova, A., Tarasova, N., Weirich, G., Merrill, M.J., Stanbridge, E.J., Expression of hypoxia-inducible cell-surface transmembrane carbonic anhydrases in human cancer (2001) Am. J. Pathol., 158, pp. 905-919
Winum, J.Y., Pastorekova, S., Jakubickova, L., Montero, J.L., Scozzafava, A., Pastorek, J., Vullo, D., Supuran, C.T., Carbonic anhydrase inhibitors: Synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with bis-sulfamates (2005) Bioorg. Med. Chem. Lett., 15, pp. 579-584
Vullo, D., Franchi, M., Gallon, E., Pastorek, J., Scozzafava, A., Pastorekova, S., Supuran, C.T., Carbonic anhydrase inhibitors: Inhibition of the tumor-associated isozyme IX with aromatic and heterocyclic sulfonamides (2003) Bioorg. Med. Chem. Lett., 13, pp. 1005-1009
Krungkrai, J., Scozzafava, A., Reungprapavut, S., Krungkrai, S.R., Rattanajak, R., Kamchonwongpaisan, S., Supuran, C.T., Carbonic anhydrase inhibitors. Inhibition of Plasmodium falciparum carbonic anhydrase with aromatic sulfonamides: Towards antimalarials with a novel mechanism of action? (2005) Bioorg Med. Chem., 13, pp. 483-489
Covarrubias Suarez, A., Larsson, A.M., Ho Gbom, M., Lindberg, J., Bergfors, T., Bjo Rkelid, C., Mowbray, S.L., Jones, T.A., Structure and function of carbonic anhydrases from mycobacterium tuberculosis (2005) J. Biol. Chem., 280, pp. 18782-18789
Chakravarty, S., Kannan, K.K., Drug-protein interactions. Refined structures of three sulfonamide drug complexes of human carbonic anhydrase I enzyme (1994) J. Mol. Biol., 243, pp. 298-309
Vidgren, J., Svensson, A., Liljas, A., Refined structure of the aminobenzolamide complex of human carbonic anhydrase II at 1.9 A and sulphonamide modelling of bovine carbonic anhydrase III (1993) Int. J. Biol. Macromol., 15, pp. 97-100
Eriksson, A.E., Jones, T.A., Liljas, A., Refined structure of human carbonic anhydrase II at 2.0 Å resolution (1988) Proteins Struct. Funct., 4, pp. 274-282
Boriack, P.A., Christianson, D.W., Kingery-Wood, J., Whitesides, G.M., Secondary interactions significantly removed from the sulfonamide binding pocket of carbonic anhydrase II influence inhibitor binding constants (1995) J. Med. Chem., 38, pp. 2286-2291
Stams, T., Chen, Y., Boriack-Sjodin, P.A., Hurt, J.D., Liao, J., May, J.A., Dean, T., Christianson, D.W., Structures of murine carbonic anhydrase IV and human carbonic anhydrase II complexed with brinzolamide: Molecular basis of isozyme-drug discrimination (1998) Protein Sci., 7, pp. 556-563
Kim, C.Y., Chandra, P.P., Jain, A., Christianson, D.W., Fluoroaromatic-fluoroaromatic interactions between inhibitors bound in the crystal lattice of human carbonic anhydrase II (2001) J. Am. Chem. Soc., 123, pp. 9620-9627
Di Fiore, A., De Simone, G., Menchise, V., Pedone, C., Casini, A., Scozzafava, A., Supuran, C.T., Carbonic anhydrase inhibitors: X-ray crystal structure of a benzenesulfonamide strong CA II and CA IX inhibitor bearing a pentafluorophenylaminothioureido tail in complex with isozyme II (2005) Bioorg. Med. Chem. Lett., 15, pp. 1937-1942
Abbate, F., Casini, A., Scozzafava, A., Supuran, C.T., Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with the perfluorobenzoyl analogue of methazolamide. Implications for the drug design of fluorinated inhibitors (2003) J. Enzyme. Inhib. Med. Chem., 18, pp. 303-308
Casini, A., Abbate, F., Scozzafava, A., Supuran, C.T., Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with a bis-sulfonamide-two heads are better than one? (2003) Bioorg. Med. Chem. Lett., 13, pp. 2759-2763
Casini, A., Antel, J., Abbate, F., Scozzafava, A., David, S., Waldeck, H., Schafer, S., Supuran, C.T., Carbonic anhydrase inhibitors: SAR and X-ray crystallographic study for the interaction of sugar sulfamates/sulfamides with isozymes I, II and IV (2003) Bioorg. Med. Chem. Lett., 13, pp. 841-845
Abbate, F., Coetzee, A., Casini, A., Ciattini, S., Scozzafava, A., Supuran, C.T., Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with the antipsychotic drug sulpiride (2004) Bioorg. Med. Chem. Lett., 14, pp. 337-341
Abbate, F., Winum, J.Y., Potter, B.V., Casini, A., Montera, 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
Weber, A., Casini, A., Heine, A., Kuhn, D., Supuran, C.T., Scozzafava, A., Klebe, G., Unexpected nanomolar inhibition of carbonic anhydrase by COX-2-selective celecoxib: New pharmacological opportunities due to related binding site recognition (2004) J. Med. Chem., 47, pp. 550-557
Pastorekova, S., Casini, A., Scozzafava, A., Vullo, D., Pastorek, J., Supuran, C.T., Carbonic anhydrase inhibitors: The first selective, membrane-impermeant inhibitors targeting the tumor-associated isozyme IX (2004) Bioorg. Med. Chem. Lett., 14, pp. 869-873
Scozzafava, A., Briganti, F., Hies, M.A., Supuran, C.T., Carbonic anhydrase inhibitors: Synthesis of membrane-impermeant low molecular weight sulfonamides possessing in vivo selectivity for the membrane-bound versus cytosolic isozymes (2000) J. Med. Chem., 43, pp. 292-300
Casey, J.R., Morgan, P.E., Vullo, D., Scozzafava, A., Mastrolorenzo, A., Supuran, C.T., Carbonic anhydrase inhibitors. Design of selective, membrane-impermeant inhibitors targeting the human tumor-associated isozyme IX (2004) J. Med. Chem., 47, pp. 2337-2347
Balaban, A.T., Dinculescu, A., Dorofeenko, G.N., Fischer, G.W., Koblik, A.V., Mezheritskii, V.V., Schroth, W., Pyrylium salts: Syntheses, reactions and physical properties (1982) Advances in Heterocyclic Chemistry, pp. 8-360. , Katritzky, A. R. (Ed.). Academic Press: New York
Supuran, C.T., Manole, G., Dinculescu, A., Schiketanz, A., Gheorghiu, M.D., Puscas, I., Balaban, A.T., Carbonic anhydrase inhibitors. V: Pyrylium salts in the synthesis of isozyme-specific inhibitors (1992) J. Pharm. Sci., 81, pp. 716-719
Khalifah, R.G., The carbon dioxide hydration activity of carbonic anhydrase (1971) J. Biol. Chem., 246, pp. 2561-2573
Brimger, 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
Otwinowski, Z., Minor, W., Processing of X-ray diffraction data collected in oscillation mode (1997) Methods Enzymol., 276, pp. 307-326
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
Engh, R.A., Huber, R., Accurate bond and angle parameters for X-ray protein structure refinement (1991) Acta Crystallogr. Sect. A, 47, pp. 392-400
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
Marquis, R. E., Whitson, J. T., Management of glaucoma: Focus on pharmacological therapy (2005) Drugs Aging, 22, pp. 1-21
Supuran, C. T., Casini, A., Scozzafava, A., Development of sulfonamide carbonic anhydrase inhibitors (CAIs) (2004) Carbonic Anhydrase - Its Inhibitors and Activators, pp. 67-148. , Supuran, C. T., Scozzafava, A., Conway, J.
Loiselle, F. B., Morgan, P. E., Alvarez, B. V., Casey, J. R., Regulation of the human NBC3 Na+/HCO3- Cotransporter by carbonic anhydrase II and PKA (2004) Am. J. Physiol. Cell Physiol., 286, pp. C1423-C1433
Lyons, K. E., Pahwa, R., Cornelia, C. L., Eisa, M. S., Elble, R. J., Fahn, S., Jankovic, J., Watts, R. L., Benefits and risks of pharmacological treatments for essential tremor (2003) Drug Saf., 26, pp. 461-481
Garske, L. A., Brown, M. G., Morrison, S. C., Acetazolamide reduces exercise capacity and increases leg fatigue under hypoxic conditions (2003) J. Appl. Physiol., 94, pp. 991-996
Winum, J. Y., Scozzafava, A., Montera, J. L., Supuran, C. T., Sulfamates and their therapeutic potential (2005) Med. Res. Rev., 25, pp. 186-228
Winum, J. Y., Pastorekova, S., Jakubickova, L., Montero, J. L., Scozzafava, A., Pastorek, J., Vullo, D., Supuran, C. T., Carbonic anhydrase inhibitors: Synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with bis-sulfamates (2005) Bioorg. Med. Chem. Lett., 15, pp. 579-584
Eriksson, A. E., Jones, T. A., Liljas, A., Refined structure of human carbonic anhydrase II at 2. 0 resolution (1988) Proteins Struct. Funct., 4, pp. 274-282
Boriack, P. A., Christianson, D. W., Kingery-Wood, J., Whitesides, G. M., Secondary interactions significantly removed from the sulfonamide binding pocket of carbonic anhydrase II influence inhibitor binding constants (1995) J. Med. Chem., 38, pp. 2286-2291
Kim, C. Y., Chandra, P. P., Jain, A., Christianson, D. W., Fluoroaromatic-fluoroaromatic interactions between inhibitors bound in the crystal lattice of human carbonic anhydrase II (2001) J. Am. Chem. Soc., 123, pp. 9620-9627
Casey, J. R., Morgan, P. E., Vullo, D., Scozzafava, A., Mastrolorenzo, A., Supuran, C. T., Carbonic anhydrase inhibitors. Design of selective, membrane-impermeant inhibitors targeting the human tumor-associated isozyme IX (2004) J. Med. Chem., 47, pp. 2337-2347
Balaban, A. T., Dinculescu, A., Dorofeenko, G. N., Fischer, G. W., Koblik, A. V., Mezheritskii, V. V., Schroth, W., Pyrylium salts: Syntheses, reactions and physical properties (1982) Advances in Heterocyclic Chemistry, pp. 8-360. , Katritzky, A. R. (Ed.). Academic Press: New York
Supuran, C. T., Manole, G., Dinculescu, A., Schiketanz, A., Gheorghiu, M. D., Puscas, I., Balaban, A. T., Carbonic anhydrase inhibitors. V: Pyrylium salts in the synthesis of isozyme-specific inhibitors (1992) J. Pharm. Sci., 81, pp. 716-719
Khalifah, R. G., The carbon dioxide hydration activity of carbonic anhydrase (1971) J. Biol. Chem., 246, pp. 2561-2573
Brimger, 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
Engh, R. A., Huber, R., Accurate bond and angle parameters for X-ray protein structure refinement (1991) Acta Crystallogr. Sect. A, 47, pp. 392-400
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
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2005 Sep 8; 48(18): 5721-5727.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 4.926, 5-year impact factor: 5.504
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-24744467784&partnerID=40&md5=1c4ee242723e3de5189fb90a3acd55d9
Keywords: 1 N (4 Sulfamoylphenylethyl) 2, 6 Trimethylpyridinium Perchlorate, Carbonate Dehydratase Ii, Carbonate Dehydratase Inhibitor, Carbonate Dehydratase Xii, Glutamine, Isoenzyme, Leucine, Phenylalanine, Sulfonamide, Threonine, Unclassified Drug, Valine, Amino Acid Sequence, Antineoplastic Activity, Article, Complex Formation, Crystal Structure, Drug Binding Site, Drug Structure, Hydrophilicity, Hydrophobicity, Protein Expression, Protein Targeting, Structure Analysis, X Ray Crystallography, Antigens, Antineoplastic Agents, Carbonic Anhydrase Ii, Cell Membrane Permeability, X-Ray, Humans, Models, Molecular, Molecular Structure, Protein Binding, Pyridinium Compounds, Quantitative Structure-Activity Relationship, Recombinant Proteins, Tumor Markers, Biological,
Affiliations:
*** IBB - CNR ***
Istituto di Biostrutture e Bioimmagini, CNR, via Mezzocannone 16, 80134 Naples, Italy
Bioindustry Park del Canavese Spa, Via Ribes 5, 10010 Colleretto Giacosa (Torino), Italy
Dipartimento delle Scienze Biologiche, Sezione Biostrutture, University of Naples Federico II, via Mezzocannone 16, 80134 Naples, Italy
Università degli Studi di Firenze, Polo Scientifico, Laboratorio di Chimica Bioinorganica, Via della Lastruccia 3, 50019 Sesto Fiorentino (Florence), Italy
Universit degli Studi di Firenze, Polo Scientifico, Laboratorio di Chimica Bioinorganica, Via della Lastruccia 3, 50019 Sesto Fiorentino (Florence), Italy
References:
Supuran, C.T., Scozzafava, A., Conway, J., (2004) Carbonic Anhydrase - Its Inhibitors and Activators, pp. 1-363. , CRC Press: Boca Rato
Scozzafava, A., Mastrolorenzo, A., Supuran, C.T., Modulation of carbonic anhydrase activity and its applications in therapy (2004) Expert Opin. Ther. Pat., 14, pp. 667-702
Pastorekova, S., Parkkila, S., Pastorek, J., Supuran, C.T., Carbonic anhydrases: Current state of the art, therapeutic applications and future prospects (2004) J. Enzyme. Inhib. Med. Chem., 19, pp. 199-229
Marquis, R.E., Whitson, J.T., Management of glaucoma: Focus on pharmacological therapy (2005) Drugs Aging, 22, pp. 1-21
Vullo, D., Innocenti, A., Nishimori, I., Pastorek, J., Scozzafava, A., Pastorekova, S., Supuran, C.T., Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides - A new target for the design of antitumor and antiglaucoma drugs? (2005) Bioorg. Med. Chem. Lett., 15, pp. 963-969
Supuran, C.T., Casini, A., Scozzafava, A., Development of sulfonamide carbonic anhydrase inhibitors (CAIs) (2004) Carbonic Anhydrase - Its Inhibitors and Activators, pp. 67-148. , Supuran, C. T., Scozzafava, A., Conway, J.
Eds., CRC Press: Boca Raton (FL), USA
Loiselle, F.B., Morgan, P.E., Alvarez, B.V., Casey, J.R., Regulation of the human NBC3 Na+/HCO3- Cotransporter by carbonic anhydrase II and PKA (2004) Am. J. Physiol. Cell Physiol., 286, pp. C1423-C1433
Rivera, C., Voipio, J., Kaila, K., Two developmental switches in GABAergic signalling: The K+-Cl- Cotransporter KCC2 and carbonic anhydrase CAVII (2005) J. Physiol., 562, pp. 27-36
Vullo, D., Voipio, J., Innocenti, A., Rivera, C., Ranki, H., Scozzafava, A., Kaila, K., Supuran, C.T., Carbonic anhydrase inhibitors. Inhibition of the human cytosolic isozyme VII with aromatic and heterocyclic sulfonamides (2005) Bioorg. Med. Chem. Lett., 15, pp. 971-976
Lyons, K.E., Pahwa, R., Cornelia, C.L., Eisa, M.S., Elble, R.J., Fahn, S., Jankovic, J., Watts, R.L., Benefits and risks of pharmacological treatments for essential tremor (2003) Drug Saf., 26, pp. 461-481
Garske, L.A., Brown, M.G., Morrison, S.C., Acetazolamide reduces exercise capacity and increases leg fatigue under hypoxic conditions (2003) J. Appl. Physiol., 94, pp. 991-996
Hori, K., Ishida, S., Inoue, M., Shinoda, K., Kawashima, S., Kitamura, S., Oguchi, Y., Treatment of cystoid macular edema with oral acetazolamide in a patient with best vitelliform macular dystrophy (2004) Retina, 24, pp. 481-482
Winum, J.Y., Scozzafava, A., Montera, J.L., Supuran, C.T., Sulfamates and their therapeutic potential (2005) Med. Res. Rev., 25, pp. 186-228
Svastova, E., Hulikova, A., Rafajova, M., Zat'ovicova, M., Gibadulinova, A., Casini, A., Cecchi, A., Pastorekova, S., Hypoxia activates the capacity of tumor-associated carbonic anhydrase IX to acidify extracellular pH (2004) FEBS Lett., 577, pp. 439-445
Pastorek, J., Pastorekova, S., Callebaut, I., Mornon, J.P., Zelnik, V., Opavsky, R., Zat'ovicova, M., Stanbridge, E.J., Cloning and characterization of MN, a human tumor-associated protein with a domain homologous to carbonic anhydrase and a putative helix-loop-helix DNA binding segment (1994) Oncogene, 9, pp. 2877-2888
Rafajova, M., Zatovicova, M., Kettmann, R., Pastorek, J., Pastorekova, S., Induction by hypoxia combined with low glucose or low bicarbonate and high posttranslational stability upon reoxygenation contribute to carbonic anhydrase IX expression in cancer cells (2004) Int. J. Oncol., 24, pp. 995-1004
Ivanov, S., Liao, S.Y., Ivanova, A., Danilkovitch-Miagkova, A., Tarasova, N., Weirich, G., Merrill, M.J., Stanbridge, E.J., Expression of hypoxia-inducible cell-surface transmembrane carbonic anhydrases in human cancer (2001) Am. J. Pathol., 158, pp. 905-919
Winum, J.Y., Pastorekova, S., Jakubickova, L., Montero, J.L., Scozzafava, A., Pastorek, J., Vullo, D., Supuran, C.T., Carbonic anhydrase inhibitors: Synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with bis-sulfamates (2005) Bioorg. Med. Chem. Lett., 15, pp. 579-584
Vullo, D., Franchi, M., Gallon, E., Pastorek, J., Scozzafava, A., Pastorekova, S., Supuran, C.T., Carbonic anhydrase inhibitors: Inhibition of the tumor-associated isozyme IX with aromatic and heterocyclic sulfonamides (2003) Bioorg. Med. Chem. Lett., 13, pp. 1005-1009
Krungkrai, J., Scozzafava, A., Reungprapavut, S., Krungkrai, S.R., Rattanajak, R., Kamchonwongpaisan, S., Supuran, C.T., Carbonic anhydrase inhibitors. Inhibition of Plasmodium falciparum carbonic anhydrase with aromatic sulfonamides: Towards antimalarials with a novel mechanism of action? (2005) Bioorg Med. Chem., 13, pp. 483-489
Covarrubias Suarez, A., Larsson, A.M., Ho Gbom, M., Lindberg, J., Bergfors, T., Bjo Rkelid, C., Mowbray, S.L., Jones, T.A., Structure and function of carbonic anhydrases from mycobacterium tuberculosis (2005) J. Biol. Chem., 280, pp. 18782-18789
Chakravarty, S., Kannan, K.K., Drug-protein interactions. Refined structures of three sulfonamide drug complexes of human carbonic anhydrase I enzyme (1994) J. Mol. Biol., 243, pp. 298-309
Vidgren, J., Svensson, A., Liljas, A., Refined structure of the aminobenzolamide complex of human carbonic anhydrase II at 1.9 A and sulphonamide modelling of bovine carbonic anhydrase III (1993) Int. J. Biol. Macromol., 15, pp. 97-100
Eriksson, A.E., Jones, T.A., Liljas, A., Refined structure of human carbonic anhydrase II at 2.0 Å resolution (1988) Proteins Struct. Funct., 4, pp. 274-282
Boriack, P.A., Christianson, D.W., Kingery-Wood, J., Whitesides, G.M., Secondary interactions significantly removed from the sulfonamide binding pocket of carbonic anhydrase II influence inhibitor binding constants (1995) J. Med. Chem., 38, pp. 2286-2291
Stams, T., Chen, Y., Boriack-Sjodin, P.A., Hurt, J.D., Liao, J., May, J.A., Dean, T., Christianson, D.W., Structures of murine carbonic anhydrase IV and human carbonic anhydrase II complexed with brinzolamide: Molecular basis of isozyme-drug discrimination (1998) Protein Sci., 7, pp. 556-563
Kim, C.Y., Chandra, P.P., Jain, A., Christianson, D.W., Fluoroaromatic-fluoroaromatic interactions between inhibitors bound in the crystal lattice of human carbonic anhydrase II (2001) J. Am. Chem. Soc., 123, pp. 9620-9627
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Abbate, F., Coetzee, A., Casini, A., Ciattini, S., Scozzafava, A., Supuran, C.T., Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with the antipsychotic drug sulpiride (2004) Bioorg. Med. Chem. Lett., 14, pp. 337-341
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Casey, J. R., Morgan, P. E., Vullo, D., Scozzafava, A., Mastrolorenzo, A., Supuran, C. T., Carbonic anhydrase inhibitors. Design of selective, membrane-impermeant inhibitors targeting the human tumor-associated isozyme IX (2004) J. Med. Chem., 47, pp. 2337-2347
Balaban, A. T., Dinculescu, A., Dorofeenko, G. N., Fischer, G. W., Koblik, A. V., Mezheritskii, V. V., Schroth, W., Pyrylium salts: Syntheses, reactions and physical properties (1982) Advances in Heterocyclic Chemistry, pp. 8-360. , Katritzky, A. R. (Ed.). Academic Press: New York
Supuran, C. T., Manole, G., Dinculescu, A., Schiketanz, A., Gheorghiu, M. D., Puscas, I., Balaban, A. T., Carbonic anhydrase inhibitors. V: Pyrylium salts in the synthesis of isozyme-specific inhibitors (1992) J. Pharm. Sci., 81, pp. 716-719
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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
Engh, R. A., Huber, R., Accurate bond and angle parameters for X-ray protein structure refinement (1991) Acta Crystallogr. Sect. A, 47, pp. 392-400
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
Carbonic anhydrase inhibitors: Stacking with Phe131 determines active site binding region of inhibitors as exemplified by the X-ray crystal structure of a membrane-impermeant antitumor sulfonamide complexed with isozyme II
Structure for the adduct of carbonic anhydrase II with 1-N-(4- sulfamoylphenyl-ethyl)-2,4,6-trimethylpyridinium perchlorate, a membrane-impermeant antitumor sulfonamide, is reported. The phenylethyl moiety fills the active site, making van der Waals interactions with side chains of Gln192, Val121, Phe131, Leu198, Thr200. The 2,4,6-trimethylpyridinium functionality is at van der Waals distance from the aliphatic chain of Ile91 being involved in strong offset face-to-face stacking with Phe131. Analyzing X-ray crystal structures of such adducts, two binding modes were observed: some inhibitors bind with their tail within the hydrophobic half of the active site, defined by residues Phe131, Val135, Leu198, Pro202, Leu204. Other derivatives bind with their tail in a different region, pointing toward the hydrophilic half and making strong parallel stacking with Phe131. This interaction orients the inhibitor toward the hydrophilic part of the active site. Impossibility to participate in it leads to its binding within the hydrophobic half. Such findings are relevant for designing better inhibitors targeting isozymes II, IX, and XII, some of which are overexpressed in hypoxic tumors. © 2005 American Chemical Society.
Structure for the adduct of carbonic anhydrase II with 1-N-(4- sulfamoylphenyl-ethyl)-2,4,6-trimethylpyridinium perchlorate, a membrane-impermeant antitumor sulfonamide, is reported. The phenylethyl moiety fills the active site, making van der Waals interactions with side chains of Gln192, Val121, Phe131, Leu198, Thr200. The 2,4,6-trimethylpyridinium functionality is at van der Waals distance from the aliphatic chain of Ile91 being involved in strong offset face-to-face stacking with Phe131. Analyzing X-ray crystal structures of such adducts, two binding modes were observed: some inhibitors bind with their tail within the hydrophobic half of the active site, defined by residues Phe131, Val135, Leu198, Pro202, Leu204. Other derivatives bind with their tail in a different region, pointing toward the hydrophilic half and making strong parallel stacking with Phe131. This interaction orients the inhibitor toward the hydrophilic part of the active site. Impossibility to participate in it leads to its binding within the hydrophobic half. Such findings are relevant for designing better inhibitors targeting isozymes II, IX, and XII, some of which are overexpressed in hypoxic tumors. © 2005 American Chemical Society.
Carbonic anhydrase inhibitors: Stacking with Phe131 determines active site binding region of inhibitors as exemplified by the X-ray crystal structure of a membrane-impermeant antitumor sulfonamide complexed with isozyme II
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Carbonic anhydrase inhibitors: Stacking with Phe131 determines active site binding region of inhibitors as exemplified by the X-ray crystal structure of a membrane-impermeant antitumor sulfonamide complexed with isozyme II
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* Carbonic anhydrase inhibitors: Binding of indanesulfonamides to the human isoform II (378 views)
Chemmedchem (ISSN: 1860-7179, 1860-7187, 1860-7187electronic), 2008 Mar; 3(3): 473-477.
Impact Factor: 3.15
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Hilvo M, Innocenti A, Monti SM, De Simone G, Supuran CT, Parkkila S
* Recent advances in research on the most novel carbonic anhydrases, CA XIII and XV (462 views)
Curr Pharm Des Current Pharmaceutical Design (ISSN: 1381-6128, 1873-4286), 2008; 14(7): 672-678.
Impact Factor: 4.399
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Calabrese V, Mancuso C, Calvani M, Rizzarelli E, Butterfield DA, Stella AM
* Nitric oxide in the central nervous system: neuroprotection versus neurotoxicity (698 views)
Nature Reviews Neuroscience (ISSN: 1471-0048), 2007 Oct; 8(10): 766-775.
Impact Factor: 24.52
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Alterio V, De Simone G, Monti SM, Scozzafava A, Supuran CT
* Carbonic anhydrase inhibitors: Inhibition of human, bacterial, and archaeal isozymes with benzene-1, 3-disulfonamides-Solution and crystallographic studies (329 views)
Bioorg Med Chem Lett Bioorganic And Medicinal Chemistry Letters (ISSN: 0960-894x), 2007 Sep 1; 17(15): 4201-4207.
Impact Factor: 2.604
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Vitale RM, Pedone C, Amodeo P, Antel J, Wurl M, Scozzafava A, Supuran CT, De Simone G
* Molecular modeling study for the binding of zonisamide and topiramate to the human mitochondrial carbonic anhydrase isoform VA (335 views)
Bioorg Med Chem (ISSN: 0968-0896, 1464-3391, 1464-3391electronic), 2007 Jun 15; 15(12): 4152-4158.
Impact Factor: 2.662
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Di Fiore A, Scozzafava A, Winum JY, Montero JL, Pedone C, Supuran CT, De Simone G
* Carbonic anhydrase inhibitors: binding of an antiglaucoma glycosyl-sulfanilamide derivative to human isoform II and its consequences for the drug design of enzyme inhibitors incorporating sugar moieties (410 views)
Bioorg Med Chem Lett Bioorganic And Medicinal Chemistry Letters (ISSN: 0960-894x), 2007 Mar 15; 17(6): 1726-1731.
Impact Factor: 2.604
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De Simone G, Supuran CT
* Antiobesity carbonic anhydrase inhibitors (438 views)
Curr Top Med Chem (ISSN: 1568-0266, 1568-0266linking, 1873-4294electronic), 2007; 7(9): 879-884.
Impact Factor: 4.325
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Leese MP, Leblond B, Smith A, Newman SP, Di Fiore A, De Simone G, Supuran CT, Purohit A, Reed MJ, Potter BVL
* 2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity (922 views)
J Med Chem (ISSN: 0022-2623print, 0022-2623linking, 1520-4804), 2006 Dec 28; 49(26): 7683-7696.
Impact Factor: 5.115
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Menchise V, De Simone G, Di Fiore A, Scozzafava A, Supuran CT
* Carbonic anhydrase inhibitors: X-ray crystallographic studies for the binding of 5-amino-1, 3, 4-thiadiazole-2-sulfonamide and 5-(4-amino-3-chloro-5-fluorophenylsulfonamido)1, 3, 4-thiadiazole-2-sulfon amide to human isoform II (308 views)
Bioorganic & Medicinal Chemistry Letters (ISSN: 0960-894x), 2006 Dec 15; 16(24): 6204-6208.
Impact Factor: 2.538
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De Simone G, Vitale RM, Di Fiore A, Pedone C, Scozzafava A, Montero JL, Winum JY, Supuran CT
* Carbonic anhydrase inhibitors: Hypoxia-activatable sulfonamides incorporating disulfide bonds that target the tumor-associated isoform IX (473 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2006 Sep 7; 49(18): 5544-5551.
Impact Factor: 5.115
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Alterio V, Vitale RM, Monti SM, Pedone C, Scozzafava A, Cecchi A, De Simone G, Supuran CT
* Carbonic anhydrase inhibitors: X-ray and molecular modeling study for the interaction of a fluorescent antitumor sulfonamide with isozyme II and IX (475 views)
J Am Chem Soc (ISSN: 0002-7863, 0002-2786, 1520-5126), 2006 Jun 28; 128(25): 8329-8335.
Impact Factor: 7.696
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Di Fiore A, Pedone C, D'Ambrosio K, Scozzafava A, De Simone G, Supuran CT
* Carbonic anhydrase inhibitors: Valdecoxib binds to a different active site region of the human isoform II as compared to the structurally related cyclooxygenase II 'selective' inhibitor celecoxib (323 views)
Bioorg Med Chem Lett Bioorganic And Medicinal Chemistry Letters (ISSN: 0960-894x), 2006 Jan 15; 16(2): 437-442.
Impact Factor: 2.538
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De Simone G, Di Fiore A, Menchise V, Pedone C, Antel J, Casini A, Scozzafava A, Wurl M, Supuran CT
* Carbonic anhydrase inhibitors. Zonisamide is an effective inhibitor of the cytosolic isozyme II and mitochondrial isozyme V: solution and X-ray crystallographic studies (420 views)
Bioorg Med Chem Lett Bioorganic And Medicinal Chemistry Letters (ISSN: 0960-894x), 2005 May 2; 15(9): 2315-2320.
Impact Factor: 2.478
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Di Fiore A, De Simone G, Menchise V, Pedone C, Casini A, Scozzafava A, Supuran CT
* Carbonic anhydrase inhibitors: X-ray crystal structure of a benzenesulfonamide strong CA II and CA IX inhibitor bearing a pentafluorophenylaminothioureido tail in complex with isozyme II (489 views)
Bioorg Med Chem Lett Bioorganic And Medicinal Chemistry Letters (ISSN: 0960-894x), 2005 Apr 1; 15(7): 1937-1942.
Impact Factor: 2.478
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* Inhibition of carbonic anhydrases by a substrate analog: benzyl carbamate directly coordinates the catalytic zinc ion mimicking bicarbonate binding (243 views)
Chem Commun (ISSN: 1364-548xelectronic, 1359-7345linking), 2018 Sep 11; 54(73): 10312-10315.
Impact Factor: 6.169
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Brunò E, Buemi MR, Di Fiore A, De LucaL, Ferro S, Angeli A, Cirilli R, Sadutto D, Alterio V, Monti SM, Supuran CT, De Simone G, Gitto R
* Probing Molecular Interactions between Human Carbonic Anhydrases (hCAs) and a Novel Class of Benzenesulfonamides (385 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2017 May 25; 60(10): 4316-4326.
Impact Factor: 6.253
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Mishra CB, Kumari S, Angeli A, Monti SM, Buonanno M, Tiwari M, Supuran CT
* Discovery of Benzenesulfonamides with Potent Human Carbonic Anhydrase Inhibitory and Effective Anticonvulsant Action: Design, Synthesis, and Pharmacological Assessment (818 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2017 Mar 23; 60(6): 2456-2469.
Impact Factor: 6.253
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Altug C, Gunes H, Nocentini A, Monti SM, Buonanno M, Supuran CT
* Synthesis of isoxazole-containing sulfonamides with potent carbonic anhydrase II and VII inhibitory properties (299 views)
Bioorg Med Chem (ISSN: 0968-0896, 1464-3391, 0968-0896linking), 2017 Feb 15; 25(4): 1456-1464.
Impact Factor: 2.881
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Angapelly S, Ramya PVS, Angeli A, Monti SM, Buonanno M, Alvala M, Supuran CT, Arifuddin M
* Discovery of 4-sulfamoyl-phenyl-β-lactams as a new class of potent carbonic anhydrase isoforms I, II, IV and VII inhibitors: The first example of subnanomolar CA IV inhibitors (255 views)
Bioorg Med Chem (ISSN: 0968-0896, 1464-3391, 0968-0896linking), 2017; 25(2): 539-544.
Impact Factor: 2.881
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Monti SM, Supuran CT, De Simone G
* DPP-4 inhibitors: a patent review (2012 - 2014) (387 views)
Expert Opin Ther Pat (ISSN: 1354-3776, 1744-7674electronic), 2015 Feb; 25(2): 209-236.
Impact Factor: 4.626
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D'Ambrosio K, Carradori S, Monti SM, Buonanno M, Secci D, Vullo D, Supuran CT, De Simone G
* Out of the active site binding pocket for carbonic anhydrase inhibitors (390 views) (PDF 237 views)
Chem Commun (ISSN: 1359-7345, 1364-548x, 1364-548xelectronic), 2015 Jan 7; 51(2): 302-305.
Impact Factor: 6.567
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Ceruso M, Carta F, Osman SM, Alothman Z, Monti SM, Supuran CT
* Inhibition studies of bacterial, fungal and protozoan β-class carbonic anhydrases with Schiff bases incorporating sulfonamide moieties (366 views)
Bioorg Med Chem (ISSN: 0968-0896, 1464-3391, 0968-0896linking), 2015; 23(15): 4181-4187.
Impact Factor: 2.923
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Iqbal J, Al-rashida M, Durdagi S, Alterio V, Di Fiore A
* Recent developments of carbonic anhydrase inhibitors as potential drugs (408 views)
Biomed Res Int (ISSN: 2314-6133, 2314-6141), 2015; 2015: 174178-174178.
Impact Factor: 2.134
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Di Fiore A, Alterio V, Monti SM, De Simone G, D’Ambrosio K
* Thermostable carbonic anhydrases in biotechnological applications (475 views)
Int J Mol Sc (ISSN: 1422-0067, 1661-6596, 1422-0067linking), 2015; 16(7): 15456-15480.
Impact Factor: 3.257
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Dathan NA, Alterio V, Troiano E, Vullo D, Ludwig M, De Simone G, Supuran CT, Monti SM
* Biochemical Characterization Of The Chloroplastic β-Carbonic Anhydrase From Flaveria Bidentis (l. ) "kuntze" (386 views)
J Enzym Inhib Med Ch (ISSN: 1475-6366, 1475-6374electronic, 1475-6366linking), 2014; 29(4): 500-504.
Impact Factor: 2.332
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Alterio V, Pan P, Parkkila S, Buonanno M, Supuran CT, Monti SM, De Simone G
* The Structural Comparison Between Membrane-Associated Human Carbonic Anhydrases Provides Insights Into Drug Design Of Selective Inhibitors (407 views)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 2014; 101(7): 769-778.
Impact Factor: 2.385
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Rami M, Dubois L, Parvathaneni NK, Alterio V, van Kuijk SJ, Monti SM, Lambin P, De Simone G, Supuran CT, Winum JY
* Hypoxia-targeting carbonic anhydrase IX inhibitors by a new series of nitroimidazole-sulfonamides/sulfamides/sulfamates (544 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2013 Nov 14; 56(21): 8512-8520.
Impact Factor: 5.48
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De Simone G, Alterio V, Supuran CT
* Exploiting the hydrophobic and hydrophilic binding sites for designing carbonic anhydrase inhibitors (507 views)
Expert Opin Drug Discov (ISSN: 1746-0441), 2013 Jul; 8(7): 793-810.
Impact Factor: 3.467
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Monti SM, Supuran CT, De Simone G
* Anticancer carbonic anhydrase inhibitors: A patent review (2008-2013) (461 views)
Expert Opin Ther Pat (ISSN: 1354-3776, 1744-7674electronic), 2013 Jun; 23(6): 737-749.
Impact Factor: 3.441
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Alterio V, Di Fiore A, D'Ambrosio K, Supuran CT, De Simone G
* Multiple binding modes of inhibitors to carbonic anhydrases: How to design specific drugs targeting 15 different isoforms? (440 views)
Chem Rev (ISSN: 0009-2665), 2012 Sep; 112(8): 4421-4468.
Impact Factor: 41.298
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De Simone G, Supuran CT
* (In)organic anions as carbonic anhydrase inhibitors (362 views)
J Chem Res (ISSN: 0162-0134, 1873-3344, 0162-0134print), 2012 Jun; 111: 117-129.
Impact Factor: 3.197
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Truppo E, Supuran CT, Sandomenico A, Vullo D, Innocenti A, Di Fiore A, Alterio V, De Simone G, Monti SM
* Carbonic anhydrase VII is S-glutathionylated without loss of catalytic activity and affinity for sulfonamide inhibitors (384 views)
Bioorg Med Chem Lett Bioorganic And Medicinal Chemistry Letters (ISSN: 0960-894x), 2012 Feb 15; 22(4): 1560-1564.
Impact Factor: 2.338
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D'Ambrosio K, Smaine F-Z, Carta F, De Simone G, Winum J-Y, Supuran CT
* Development of potent carbonic anhydrase inhibitors incorporating both sulfonamide and sulfamide groups (467 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2012; 55(15): 6776-6783.
Impact Factor: 5.614
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Di Fiore A, Maresca A, Supuran CT, De Simone G
* Hydroxamate represents a versatile zinc binding group for the development of new carbonic anhydrase inhibitors (361 views)
Chem Commun (ISSN: 1359-7345, 1364-548x, 1364-548xelectronic), 2012; 48(70): 8838-8840.
Impact Factor: 6.378
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Di Fiore A, Maresca A, Alterio V, Supuran CT, De Simone G
* Carbonic anhydrase inhibitors: X-ray crystallographic studies for the binding of N-substituted benzenesulfonamides to human isoform II (338 views)
Chem Commun (ISSN: 1359-7345, 1364-548x, 1364-548xelectronic), 2011; 47(42): 11636-11638.
Impact Factor: 6.169
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Viparelli F, Monti SM, De Simone G, Innocenti A, Scozzafava A, Xu Y, Morel FMM, Supuran CT
* Inhibition Of The R1 Fragment Of The Cadmium-Containing Zeta-Class Carbonic Anhydrase From The Diatom Thalassiosira Weissflogii With Anions (333 views)
Bioorganic & Medicinal Chemistry Letters (ISSN: 0960-894x), 2010 Sep 15; 20(16): 4745-4748.
Impact Factor: 2.661
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Alterio V, Monti SM, Truppo E, Pedone C, Supuran CT, De Simone G
* The first example of a significant active site conformational rearrangement in a carbonic anhydrase-inhibitor adduct: The carbonic anhydrase I-topiramate complex (409 views)
Org Biomol Chem (ISSN: 1477-0520, 1477-0539, 1477-0539electronic), 2010 Sep 7; 8(15): 3528-3533.
Impact Factor: 3.451
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Di Fiore A, Monti SM, Innocenti A, Winum J-Y, De Simone G, Supuran CT
* Carbonic anhydrase inhibitors: Crystallographic and solution binding studies for the interaction of a boron-containing aromatic sulfamide with mammalian isoforms I-XV (352 views)
Bioorg Med Chem Lett Bioorganic And Medicinal Chemistry Letters (ISSN: 0960-894x), 2010 Jun 15; 20(12): 3601-3605.
Impact Factor: 2.661
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Guler OO, De Simone G, Supuran CT
* Drug design studies of the novel antitumor targets carbonic anhydrase IX and XII (540 views)
Curr Med Chem (ISSN: 0929-8673, 1875-533x, 1875-533xelectronic), 2010; 17(15): 1516-1526.
Impact Factor: 4.63
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Supuran CT, Di Fiore A, Alterio V, Monti SM, De Simone G
* Recent advances in structural studies of the carbonic anhydrase family: The crystal structure of human CA IX and CA XIII (456 views)
Curr Pharm Des Current Pharmaceutical Design (ISSN: 1381-6128, 1873-4286), 2010; 16(29): 3246-3254.
Impact Factor: 4.774
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Vitale RM, Alterio V, Innocenti A, Winum JY, Monti SM, De Simone G, Supuran CT
* Carbonic anhydrase inhibitors. Comparison of aliphatic sulfamate/bis- sulfamate adducts with isozymes II and IX as a platform for designing tight-binding, more isoform-selective inhibitors (420 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2009 Oct 8; 52(19): 5990-5998.
Impact Factor: 4.802
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De Simone G, Scozzafava A, Supuran CT
* Which Carbonic Anhydrases are Targeted by the Antiepileptic Sulfonamides and Sulfamates? (352 views)
Chem Biol Drug Des (ISSN: 1747-0277, 1747-0285), 2009 Sep; 74(3): 317-321.
Impact Factor: 2.473
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Di Fiore A, Monti SM, Hilvo M, Parkkila S, Romano V, Scaloni A, Pedone C, Scozzafava A, Supuran CT, De Simone G
* Crystal structure of human carbonic anhydrase XIII and its complex with the inhibitor acetazolamide (465 views)
Proteins (ISSN: 1097-0134, 0887-3585, 1097-0134electronic), 2009 Jan; 74(1): 164-175.
Impact Factor: 3.085
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Hilvo M, Baranauskiene L, Salzano AM, Scaloni A, Matulis D, Innocenti A, Scozzafava A, Monti SM, Di Fiore A, De Simone G, Lindfors M, Janis J, Valjakka J, Pastorekova S, Pastorek J, Kulomaa MS, Nordlund HR, Supuran CT, Parkkila S
* Biochemical characterization of CA IX, one of the most active carbonic anhydrase isozymes (459 views)
Jbc Papers (ISSN: 0021-9258, 1083-351x, 0021-9258linking), 2008 Oct 10; 283(41): 27799-27809.
Impact Factor: 5.52
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D'Ambrosio K, Vitale R, Dogne J, Masereel B, Innocenti A, Scozzafava A, De Simone G, Supuran CT
* Ccarbonic Anhydrase Inhibitors: Bioreductive Nitro-Containing Sulfonamides With Selectivity For Targeting The Tumor Associated Isoforms Ix And Xii (814 views)
J Med Chem (ISSN: 1520-4804, 0022-2623, 0022-2623print), 2008 Jun 12; 51(11): 3230-3237.
Impact Factor: 4.898
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Supuran CT, Di Fiore A, De Simone G
* Carbonic anhydrase inhibitors as emerging drugs for the treatment of obesity (556 views)
Expert Opin Emerg Drugsexpert Opinion On Emerging Drugs (ISSN: 1472-8214), 2008 Jun; 13(2): 383-392.
Impact Factor: 3.08
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Di Fiore A, Pedone C, Antel J, Waldeck H, Witte A, Wurl M, Scozzafava A, Supuran CT, De Simone G
* 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 (385 views)
Bioorg Med Chem Lett (ISSN: 1464-3405, 0960-894x, 1464-3405electronic), 2008 Apr 15; 18(8): 2669-2674.
Impact Factor: 2.531
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Innocenti A, Scozzafava A, Parkkila S, Puccetti L, De Simone G, Supuran CT
* Investigations of the esterase, phosphatase, and sulfatase activities of the cytosolic mammalian carbonic anhydrase isoforms I, II, and XIII with 4-nitrophenyl esters as substrates (360 views)
Bioorg Med Chem Lett Bioorganic And Medicinal Chemistry Letters (ISSN: 0960-894x), 2008 Apr 1; 18(7): 2267-2271.
Impact Factor: 2.531
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Leese MP, Jourdan FL, Gaukroger K, Mahon MF, Newman SP, Foster PA, Stengel C, Regis-Lydi S, Ferrandis E, Di Fiore A, De Simone G, Supuran CT, Purohit A, Reed MJ, Potter BVL
* Structure-activity relationships of C-17 cyano-substituted estratrienes as anticancer agents (462 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2008 Mar 13; 51(5): 1295-1308.
Impact Factor: 4.898
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De Simone G, Di Fiore A, Supuran CT
* Are carbonic anhydrase inhibitors suitable for obtaining antiobesity drugs? (469 views)
Curr Pharm Des Current Pharmaceutical Design (ISSN: 1381-6128, 1873-4286), 2008 Mar; 14(7): 655-660.
Impact Factor: 4.399
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D'Ambrosio K, Masereel B, Thiry A, Scozzafava A, Supuran CT, De Simone G
* Carbonic anhydrase inhibitors: Binding of indanesulfonamides to the human isoform II (378 views)
Chemmedchem (ISSN: 1860-7179, 1860-7187, 1860-7187electronic), 2008 Mar; 3(3): 473-477.
Impact Factor: 3.15
View Export to BibTeX Export to EndNote
Hilvo M, Innocenti A, Monti SM, De Simone G, Supuran CT, Parkkila S
* Recent advances in research on the most novel carbonic anhydrases, CA XIII and XV (462 views)
Curr Pharm Des Current Pharmaceutical Design (ISSN: 1381-6128, 1873-4286), 2008; 14(7): 672-678.
Impact Factor: 4.399
View Export to BibTeX Export to EndNote
Calabrese V, Mancuso C, Calvani M, Rizzarelli E, Butterfield DA, Stella AM
* Nitric oxide in the central nervous system: neuroprotection versus neurotoxicity (698 views)
Nature Reviews Neuroscience (ISSN: 1471-0048), 2007 Oct; 8(10): 766-775.
Impact Factor: 24.52
View Export to BibTeX Export to EndNote
Alterio V, De Simone G, Monti SM, Scozzafava A, Supuran CT
* Carbonic anhydrase inhibitors: Inhibition of human, bacterial, and archaeal isozymes with benzene-1, 3-disulfonamides-Solution and crystallographic studies (329 views)
Bioorg Med Chem Lett Bioorganic And Medicinal Chemistry Letters (ISSN: 0960-894x), 2007 Sep 1; 17(15): 4201-4207.
Impact Factor: 2.604
View Export to BibTeX Export to EndNote
Vitale RM, Pedone C, Amodeo P, Antel J, Wurl M, Scozzafava A, Supuran CT, De Simone G
* Molecular modeling study for the binding of zonisamide and topiramate to the human mitochondrial carbonic anhydrase isoform VA (335 views)
Bioorg Med Chem (ISSN: 0968-0896, 1464-3391, 1464-3391electronic), 2007 Jun 15; 15(12): 4152-4158.
Impact Factor: 2.662
View Export to BibTeX Export to EndNote
Di Fiore A, Scozzafava A, Winum JY, Montero JL, Pedone C, Supuran CT, De Simone G
* Carbonic anhydrase inhibitors: binding of an antiglaucoma glycosyl-sulfanilamide derivative to human isoform II and its consequences for the drug design of enzyme inhibitors incorporating sugar moieties (410 views)
Bioorg Med Chem Lett Bioorganic And Medicinal Chemistry Letters (ISSN: 0960-894x), 2007 Mar 15; 17(6): 1726-1731.
Impact Factor: 2.604
View Export to BibTeX Export to EndNote
De Simone G, Supuran CT
* Antiobesity carbonic anhydrase inhibitors (438 views)
Curr Top Med Chem (ISSN: 1568-0266, 1568-0266linking, 1873-4294electronic), 2007; 7(9): 879-884.
Impact Factor: 4.325
View Export to BibTeX Export to EndNote
Leese MP, Leblond B, Smith A, Newman SP, Di Fiore A, De Simone G, Supuran CT, Purohit A, Reed MJ, Potter BVL
* 2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity (922 views)
J Med Chem (ISSN: 0022-2623print, 0022-2623linking, 1520-4804), 2006 Dec 28; 49(26): 7683-7696.
Impact Factor: 5.115
View Export to BibTeX Export to EndNote
Menchise V, De Simone G, Di Fiore A, Scozzafava A, Supuran CT
* Carbonic anhydrase inhibitors: X-ray crystallographic studies for the binding of 5-amino-1, 3, 4-thiadiazole-2-sulfonamide and 5-(4-amino-3-chloro-5-fluorophenylsulfonamido)1, 3, 4-thiadiazole-2-sulfon amide to human isoform II (308 views)
Bioorganic & Medicinal Chemistry Letters (ISSN: 0960-894x), 2006 Dec 15; 16(24): 6204-6208.
Impact Factor: 2.538
View Export to BibTeX Export to EndNote
De Simone G, Vitale RM, Di Fiore A, Pedone C, Scozzafava A, Montero JL, Winum JY, Supuran CT
* Carbonic anhydrase inhibitors: Hypoxia-activatable sulfonamides incorporating disulfide bonds that target the tumor-associated isoform IX (473 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2006 Sep 7; 49(18): 5544-5551.
Impact Factor: 5.115
View Export to BibTeX Export to EndNote
Alterio V, Vitale RM, Monti SM, Pedone C, Scozzafava A, Cecchi A, De Simone G, Supuran CT
* Carbonic anhydrase inhibitors: X-ray and molecular modeling study for the interaction of a fluorescent antitumor sulfonamide with isozyme II and IX (475 views)
J Am Chem Soc (ISSN: 0002-7863, 0002-2786, 1520-5126), 2006 Jun 28; 128(25): 8329-8335.
Impact Factor: 7.696
View Export to BibTeX Export to EndNote
Di Fiore A, Pedone C, D'Ambrosio K, Scozzafava A, De Simone G, Supuran CT
* Carbonic anhydrase inhibitors: Valdecoxib binds to a different active site region of the human isoform II as compared to the structurally related cyclooxygenase II 'selective' inhibitor celecoxib (323 views)
Bioorg Med Chem Lett Bioorganic And Medicinal Chemistry Letters (ISSN: 0960-894x), 2006 Jan 15; 16(2): 437-442.
Impact Factor: 2.538
View Export to BibTeX Export to EndNote
De Simone G, Di Fiore A, Menchise V, Pedone C, Antel J, Casini A, Scozzafava A, Wurl M, Supuran CT
* Carbonic anhydrase inhibitors. Zonisamide is an effective inhibitor of the cytosolic isozyme II and mitochondrial isozyme V: solution and X-ray crystallographic studies (420 views)
Bioorg Med Chem Lett Bioorganic And Medicinal Chemistry Letters (ISSN: 0960-894x), 2005 May 2; 15(9): 2315-2320.
Impact Factor: 2.478
View Export to BibTeX Export to EndNote
Di Fiore A, De Simone G, Menchise V, Pedone C, Casini A, Scozzafava A, Supuran CT
* Carbonic anhydrase inhibitors: X-ray crystal structure of a benzenesulfonamide strong CA II and CA IX inhibitor bearing a pentafluorophenylaminothioureido tail in complex with isozyme II (489 views)
Bioorg Med Chem Lett Bioorganic And Medicinal Chemistry Letters (ISSN: 0960-894x), 2005 Apr 1; 15(7): 1937-1942.
Impact Factor: 2.478
View Export to BibTeX Export to EndNote
50 Records (49 excluding Abstracts).
Total impact factor: 254.659 (249.544 excluding Abstracts).
Total 5 year impact factor: 259.661 (254.157 excluding Abstracts).
Total impact factor: 254.659 (249.544 excluding Abstracts).
Total 5 year impact factor: 259.661 (254.157 excluding Abstracts).
478 views. Last view on Saturday 28 January 2023, 8:02:13
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