Carbonic anhydrase inhibitors: Hypoxia-activatable sulfonamides incorporating disulfide bonds that target the tumor-associated isoform IX (474 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2006 Sep 7; 49(18): 5544-5551.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 5.115, 5-year impact factor: 5.504
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-33748541296&partnerID=40&md5=49954404a83f3962637179b83a2a6e38
Keywords: Acetazolamide, Carbonate Dehydratase Inhibitor, Diclofenamide, Ethoxzolamide, Glutamine, Indisulam, Isoenzyme, Leucine, Nitrogen Derivative, Phenylalanine, Proline, Propionamide Derivative, Sulfonamide, Sulpiride, Thiobenzamide Derivative, Thiol Derivative, Threonine, Valine, Zinc Ion, Zonisamide, Article, Concentration Response, Crystal Structure, Cytosol, Disulfide Bond, Drug Protein Binding, Drug Targeting, Enzyme Inhibition, Hydrogen Bond, Hydrophobicity, Hypoxia, Molecular Interaction, Structure Activity Relation, X Ray Crystallography, Anoxia, Antigens, Neoplasm, Carbonic Anhydrase Ii, Carbonic Anhydrase Inhibitors, X-Ray, Enzyme Activation, Humans, Hydrogen Bonding, Models, Molecular Structure, Prodrugs, Structure-Activity Relationship, Sulfhydryl Compounds,
Affiliations:
*** IBB - CNR ***
Istituto di Biostrutture e Bioimmagini-CNR, Via Mezzocannone 16, 80134 Naples, Italy
Dipartimento delle Scienze Biologiche-Sezione Biostrutture, University of Naples Federico II, Via Mezzocannone 16, 80134 Naples, Italy
Polo Scientifico, Laboratorio di Chimica Bioinorganica, Universita degli Studi di Firenze, Via della Lastruccia 3, 50019 Sesto Fiorentino, Florence, Italy
Laboratoire de Chimie Biomoléculaire, Ecole Nationale Supérieure de Chimie de Montpellier, Université Montpellier II, 8 Rue de l'Ecole Normale, 34296 Montpellier Cedex, France
References:
Pastorekova, S., Pastorek, J., Cancer-related carbonic anhydrase isozymes (2004) Carbonic Anhydrase. Its Inhibitors and Activators, pp. 253-280. , Supuran, C. T., Scozzafava, A., Conway, J., Eds.
CRC Press: Boca Raton, F
Supuran, C.T., Scozzafava, A., Casini, A., Carbonic anhydrase inibitors (2003) Med. Res. Rev., 23, pp. 146-189
Casini, A., Scozzafava, A., Mastrolorenzo, A., Supuran, C.T., Sulfonamides and sulfonylated derivatives as anticancer agents (2002) Curr. Cancer Drug Targets, 2, pp. 55-75
Wykoff, C.C., Beasley, N.J., Watson, P.H., Turner, K.J., Pastorek, J., Sibtain, A., Wilson, G.D., Harris, A.L., Hypoxia-inducible regulation of tumor-associated carbonic anhydrases (2000) Cancer Res., 60, pp. 7075-7083
Potter, C.P.S., Harris, A.L., Diagnostics, prognostics and therapeutic implications of carbonic anhydrases in cancer (2003) Br. J. Cancer, 89, pp. 2-7
Jain, R.K., Normalization of tumor vasculature: An emerging concept in antiangiogenic therapy (2005) Science, 307, pp. 58-62
Pastorek, J., Pastorekova, S., Callebaut, I., Mornon, J.P., Zelnik, V., Opavsky, R., Zatovicova, M., Kettmann, R., 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. 2788-2888
Opavský, R., Pastorekova, S., Zelnik, V., Gibadulinova, A., Stanbridge, E.J., Zavada, J., Kettmann, R., Pastorek, J., Human MN/CA9 gene, a novel member of the carbonic anhydrase family: Structure and exon to protein domain relationship (1996) Genomics, 33, pp. 480-487
Maxwell, P.H., Wiesener, M.S., Chang, G.W., Clifford, S.C., Vaux, E.C., Cockman, M.E., Wykoff, C.C., Ratcliffe, P.J., The tumour suppressor protein VHL targets hypoxia-inducible factors for oxygen-dependent proteolysis (1999) Nature, 399, pp. 271-275
Epstein, A.C.R., Gleadle, J.M., McNeil, L.A., C. elegans EGL-9 and mammalian homologs define a family of dioxygenases that regulate HIF by prolyl hydroxylation (2001) Cell, 107, pp. 43-54
Ratcliffe, P.J., Pugh, C.W., Maxwell, P.H., Targeting tumors through the HIF system (2000) Nat. Med., 6, pp. 1315-1316
Jaakkola, P., Mole, D.R., Tian, Y.M., Wilson, M.I., Gielbert, J., Gaskell, S.J., Kriegsheim, A.V., Ratcliffe, P.J., Targeting of HIF-α to the von Hippel Lindau ubiquitilation complex by O2-regulated prolyl hydroxylation (2001) Science, 292, pp. 468-472
Semenza, G.L., Targeting HIF-1 for cancer therapy (2003) Nat. Rev. Cancer, 3, pp. 721-732
Svastova, E., Hulikova, A., Rafajova, M., Zatovicova, 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
Cecchi, A., Hulikova, A., Pastorek, J., Pastorekova, S., Scozzafava, A., Winum, J.-Y., Montero, J.-L., Supuran, C.T., 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 (2005) J. Med. Chem., 48, pp. 4834-4841
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
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
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
Winum, J.Y., Scozzafava, A., Montero, J.L., Supuran, C.T., Sulfamates and their therapeutic potential (2005) Med. Res. Rev., 25, pp. 186-228
Abbate, F., Casini, A., Owa, T., Scozzafava, A., Supuran, C.T., Carbonic anhydrase inhibitors: E7070, a sulfonamide anticancer agent, potently inhibits cytosolic isozymes I and II, and transmembrane, tumor-associated isozyme IX (2004) Bioorg. Med. Chem. Lett., 14, pp. 217-223
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
Supuran, C.T., Briganti, F., Tilli, S., Chegwidden, W.R., Scozzafava, A., Carbonic anhydrase inhibitors: Sulfonamides as antitumor agents? (2001) Bioorg. Med. Chem., 9, pp. 703-714
Parkkila, S., Rajaniemi, H., Parkkila, A.K., Kivela, J., Waheed, A., Pastorekova, S., Pastorek, J., Sly, W.S., Carbonic anhydrase inhibitor suppresses invasion of renal cancer cells in vitro (2000) Proc. Natl. Acad. Sci. U.S.A., 97, pp. 2220-2224
Denny, W.A., Tumor-activated prodrugs. A new approach to cancer therapy (2004) Cancer Invest., 22, pp. 604-619
Stratford, I.J., Williams, K.J., Cowen, R.L., Jaffar, M., Combining bioreductive drugs and radiation for the treatment of solid tumors (2003) Semin. Radiat. Oncol., 13, pp. 42-52
Frein, D., Schildknecht, S., Bachschmid, M., Ullrich, V., Redox regulation: A new challenge for pharmacology (2005) Biochem. Pharmacol., 70, pp. 811-823
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Hay, M.P., Pruijn, F.B., Gamage, S.A., Liyanage, H.D., Kovacs, M.S., Patterson, A.V., Wilson, W.R., Denny, W.A., DNA-targeted 1,2,4-benzotriazine 1,4-dioxides: Potent analogues of the hypoxia-selective cytotoxin tirapazamine (2004) J. Med. Chem., 47, pp. 475-488
Seow, H.A., Penketh, P.G., Shyam, K., Rockwell, S., Sartorelli, A.C., 1,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-[[1-(4-nitrophenyl)-ethoxy] carbonyl]hydrazine: An anticancer agent targeting hypoxic cells (2005) Proc. Natl. Acad. Sci. U.S.A., 102, pp. 9282-9287
Nomura, M., Shuto, S., Matsuda, A., Synthesis of the cyclic and acyclic acetal derivatives of 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine, a potent antitumor nucleoside. Design of prodrugs to be selectively activated in tumor tissues via the bio-reduction-hydrolysis mechanism (2003) Bioorg. Med. Chem., 11, pp. 2453-2461
Phillips, R.M., Jaffar, M., Maitland, D.J., Loadman, P.M., Shnyder, S.D., Steans, G., Cooper, P.A., Stratford, I.J., Pharmacological and biological evaluation of a series of substituted 1,4-naphthoquinone bioreductive drugs (2004) Biochem. Pharmacol., 68, pp. 2107-2116
Welsh, S.J., Williams, R.R., Birmingham, A., Newman, D.J., Kirkpatrick, D.L., Powis, G., The thioredoxin redox inhibitors 1-methylpropyl 2-imidazolyl disulfide and pleurotin inhibit hypoxia-induced factor 1-alpha and vascular endothelial growth factor formation (2003) Mol. Cancer Ther., 2, pp. 235-243
Scozzafava, A., Menabuoni, L., Mincione, F., Briganti, F., Mincione, G., Supuran, C.T., Carbonic anhydrase inhibitors. Synthesis of water-soluble, topically effective, intraocular pressure-lowering aromatic/heterocyclic sulfonamides containing cationic or anionic moieties: Is the tail more important than the ring? (1999) J. Med. Chem., 42, pp. 2641-2650
Winum, J.Y., Dogne, J.M., Casini, A., De Leval, X., Montero, J.L., Scozzafava, A., Vullo, D., Supuran, C.T., Carbonic anhydrase inhibitors: Synthesis and inhibition of cytosolic/membrane-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating hydrazino moieties (2005) J. Med. Chem., 48, pp. 2121-2125
Turpin, J.A., Song, Y., Inman, J.K., Huang, M., Wallqvist, A., Maynard, A., Covell, D.G., Appella, E., Synthesis and biological properties of novel pyridinioalkanoyl thiolesters (PATE) as anti-HIV-1 agents that target the viral nucleocapsid protein zinc fingers (1999) J. Med. Chem., 42, pp. 67-86
Innocenti, A., Vullo, D., Scozzafava, A., Supuran, C.T., Carbonic anhydrase inhibitors. Inhibition of isozymes I, II, IV, V and IX with anions isosteric and isoelectronic with sulfate, nitrate and carbonate (2005) Bioorg. Med. Chem. Lett., 15, pp. 567-571
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
Eriksson, A.E., Jones, T.A., Liljas, A., Refined structure of human carbonic anhydrase II at 2.0 Å resolution (1988) Proteins: Struct., Funct., Genet., 4, pp. 274-282
Brünger, 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: Biol. Crystallogr., 54, pp. 905-921
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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
Alterio, V., Vitale, R.M., Monti, S.M., Pedone, C., Scozzafava, A., Cecchi, A., De Simone, G., Supuran, C.T., Carbonic anhydrase inhibitors: X-ray and molecular modeling study for the interaction of a fluorescent antitumor sulfonamide with isozyme II and IX (2006) J. Am. Chem. Soc., 128, pp. 8329-8335
Pearlman, D.A., Case, D.A., Caldwell, J.W., Ross, W.S., Cheatham III, T.E., DeBolt, S., Ferguson, D., Kollman, P., "AMBER", a package of computer programs for applying molecular mechanics, normal mode analysis, molecular dynamics and free energy calculations to stimulate the structural and energetic properties of molecules (1995) Comput. Phys. Commun., 91, pp. 1-42
Wang, J., Cieplak, P., Kollman, P.A., How well does a restrained electrostatic potential (RESP) model perform in calculating conformational energies of organic and biological molecules? (2000) J. Comput. Chem., 21, pp. 1049-1074
Bayly, C.I., Cieplak, P., Cornell, W., Kollman, P.A., A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges: The RESP model (1993) J. Phys. Chem., 97, pp. 10269-10280
Schmidt, M.W., Baldridge, K.K., Boatz, J.A., Elbert, S.T., Gordon, M.S., Jensen, J.H., Koseki, S., Nguyen, K.A., General atomic and molecular electronic structure system (1993) J. Comput. Chem., 14, pp. 1347-1363
Suarez, D., Merz Jr., K.M., Molecular dynamics simulations of the mononuclear zinc-beta-lactamase from Bacillus cereus (2001) J. Am. Chem. Soc., 123, pp. 3759-3770
Hoops, S.C., Anderson, K.W., Merz Jr., K.M., Force field design for metalloproteins (1991) J. Am. Chem. Soc., 113, pp. 8262-8270
Ryckaert, J.P., Ciccotti, G., Berendsen, H.J., Numerical integration of the Cartesian equations of motion of a system with constraints: Molecular dynamics of n-alkanes (1977) C. J. Comput. Phys., 23, pp. 327-341
Koradi, R., Billeter, M., Wuethrich, K., MOLMOL: A program for display and analysis of macromolecular structures (1996) J. Mol. Graphics, 14, pp. 51-55. , plates 29-32
Wykoff, C. C., Beasley, N. J., Watson, P. H., Turner, K. J., Pastorek, J., Sibtain, A., Wilson, G. D., Harris, A. L., Hypoxia-inducible regulation of tumor-associated carbonic anhydrases (2000) Cancer Res., 60, pp. 7075-7083
Potter, C. P. S., Harris, A. L., Diagnostics, prognostics and therapeutic implications of carbonic anhydrases in cancer (2003) Br. J. Cancer, 89, pp. 2-7
Jain, R. K., Normalization of tumor vasculature: An emerging concept in antiangiogenic therapy (2005) Science, 307, pp. 58-62
Opavsk, R., Pastorekova, S., Zelnik, V., Gibadulinova, A., Stanbridge, E. J., Zavada, J., Kettmann, R., Pastorek, J., Human MN/CA9 gene, a novel member of the carbonic anhydrase family: Structure and exon to protein domain relationship (1996) Genomics, 33, pp. 480-487
Maxwell, P. H., Wiesener, M. S., Chang, G. W., Clifford, S. C., Vaux, E. C., Cockman, M. E., Wykoff, C. C., Ratcliffe, P. J., The tumour suppressor protein VHL targets hypoxia-inducible factors for oxygen-dependent proteolysis (1999) Nature, 399, pp. 271-275
Epstein, A. C. R., Gleadle, J. M., McNeil, L. A., C. elegans EGL-9 and mammalian homologs define a family of dioxygenases that regulate HIF by prolyl hydroxylation (2001) Cell, 107, pp. 43-54
Ratcliffe, P. J., Pugh, C. W., Maxwell, P. H., Targeting tumors through the HIF system (2000) Nat. Med., 6, pp. 1315-1316
Semenza, G. L., Targeting HIF-1 for cancer therapy (2003) Nat. Rev. Cancer, 3, pp. 721-732
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
Winum, J. Y., Scozzafava, A., Montero, J. L., Supuran, C. T., Sulfamates and their therapeutic potential (2005) Med. Res. Rev., 25, pp. 186-228
Supuran, C. T., Briganti, F., Tilli, S., Chegwidden, W. R., Scozzafava, A., Carbonic anhydrase inhibitors: Sulfonamides as antitumor agents? (2001) Bioorg. Med. Chem., 9, pp. 703-714
Denny, W. A., Tumor-activated prodrugs. A new approach to cancer therapy (2004) Cancer Invest., 22, pp. 604-619
Stratford, I. J., Williams, K. J., Cowen, R. L., Jaffar, M., Combining bioreductive drugs and radiation for the treatment of solid tumors (2003) Semin. Radiat. Oncol., 13, pp. 42-52
Hay, M. P., Pruijn, F. B., Gamage, S. A., Liyanage, H. D., Kovacs, M. S., Patterson, A. V., Wilson, W. R., Denny, W. A., DNA-targeted 1, 2, 4-benzotriazine 1, 4-dioxides: Potent analogues of the hypoxia-selective cytotoxin tirapazamine (2004) J. Med. Chem., 47, pp. 475-488
Seow, H. A., Penketh, P. G., Shyam, K., Rockwell, S., Sartorelli, A. C., 1, 2-Bis (methylsulfonyl) -1- (2-chloroethyl) -2- [[1- (4-nitrophenyl) -ethoxy] carbonyl] hydrazine: An anticancer agent targeting hypoxic cells (2005) Proc. Natl. Acad. Sci. U. S. A., 102, pp. 9282-9287
Phillips, R. M., Jaffar, M., Maitland, D. J., Loadman, P. M., Shnyder, S. D., Steans, G., Cooper, P. A., Stratford, I. J., Pharmacological and biological evaluation of a series of substituted 1, 4-naphthoquinone bioreductive drugs (2004) Biochem. Pharmacol., 68, pp. 2107-2116
Welsh, S. J., Williams, R. R., Birmingham, A., Newman, D. J., Kirkpatrick, D. L., Powis, G., The thioredoxin redox inhibitors 1-methylpropyl 2-imidazolyl disulfide and pleurotin inhibit hypoxia-induced factor 1-alpha and vascular endothelial growth factor formation (2003) Mol. Cancer Ther., 2, pp. 235-243
Winum, J. Y., Dogne, J. M., Casini, A., De Leval, X., Montero, J. L., Scozzafava, A., Vullo, D., Supuran, C. T., Carbonic anhydrase inhibitors: Synthesis and inhibition of cytosolic/membrane-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating hydrazino moieties (2005) J. Med. Chem., 48, pp. 2121-2125
Turpin, J. A., Song, Y., Inman, J. K., Huang, M., Wallqvist, A., Maynard, A., Covell, D. G., Appella, E., Synthesis and biological properties of novel pyridinioalkanoyl thiolesters (PATE) as anti-HIV-1 agents that target the viral nucleocapsid protein zinc fingers (1999) J. Med. Chem., 42, pp. 67-86
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
Eriksson, A. E., Jones, T. A., Liljas, A., Refined structure of human carbonic anhydrase II at 2. 0 resolution (1988) Proteins: Struct., Funct., Genet., 4, pp. 274-282
Br nger, 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: Biol. Crystallogr., 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
Pearlman, D. A., Case, D. A., Caldwell, J. W., Ross, W. S., Cheatham III, T. E., DeBolt, S., Ferguson, D., Kollman, P., "AMBER", a package of computer programs for applying molecular mechanics, normal mode analysis, molecular dynamics and free energy calculations to stimulate the structural and energetic properties of molecules (1995) Comput. Phys. Commun., 91, pp. 1-42
Bayly, C. I., Cieplak, P., Cornell, W., Kollman, P. A., A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges: The RESP model (1993) J. Phys. Chem., 97, pp. 10269-10280
Schmidt, M. W., Baldridge, K. K., Boatz, J. A., Elbert, S. T., Gordon, M. S., Jensen, J. H., Koseki, S., Nguyen, K. A., General atomic and molecular electronic structure system (1993) J. Comput. Chem., 14, pp. 1347-1363
Hoops, S. C., Anderson, K. W., Merz Jr., K. M., Force field design for metalloproteins (1991) J. Am. Chem. Soc., 113, pp. 8262-8270
Ryckaert, J. P., Ciccotti, G., Berendsen, H. J., Numerical integration of the Cartesian equations of motion of a system with constraints: Molecular dynamics of n-alkanes (1977) C. J. Comput. Phys., 23, pp. 327-341
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2006 Sep 7; 49(18): 5544-5551.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 5.115, 5-year impact factor: 5.504
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-33748541296&partnerID=40&md5=49954404a83f3962637179b83a2a6e38
Keywords: Acetazolamide, Carbonate Dehydratase Inhibitor, Diclofenamide, Ethoxzolamide, Glutamine, Indisulam, Isoenzyme, Leucine, Nitrogen Derivative, Phenylalanine, Proline, Propionamide Derivative, Sulfonamide, Sulpiride, Thiobenzamide Derivative, Thiol Derivative, Threonine, Valine, Zinc Ion, Zonisamide, Article, Concentration Response, Crystal Structure, Cytosol, Disulfide Bond, Drug Protein Binding, Drug Targeting, Enzyme Inhibition, Hydrogen Bond, Hydrophobicity, Hypoxia, Molecular Interaction, Structure Activity Relation, X Ray Crystallography, Anoxia, Antigens, Neoplasm, Carbonic Anhydrase Ii, Carbonic Anhydrase Inhibitors, X-Ray, Enzyme Activation, Humans, Hydrogen Bonding, Models, Molecular Structure, Prodrugs, Structure-Activity Relationship, Sulfhydryl Compounds,
Affiliations:
*** IBB - CNR ***
Istituto di Biostrutture e Bioimmagini-CNR, Via Mezzocannone 16, 80134 Naples, Italy
Dipartimento delle Scienze Biologiche-Sezione Biostrutture, University of Naples Federico II, Via Mezzocannone 16, 80134 Naples, Italy
Polo Scientifico, Laboratorio di Chimica Bioinorganica, Universita degli Studi di Firenze, Via della Lastruccia 3, 50019 Sesto Fiorentino, Florence, Italy
Laboratoire de Chimie Biomoléculaire, Ecole Nationale Supérieure de Chimie de Montpellier, Université Montpellier II, 8 Rue de l'Ecole Normale, 34296 Montpellier Cedex, France
References:
Pastorekova, S., Pastorek, J., Cancer-related carbonic anhydrase isozymes (2004) Carbonic Anhydrase. Its Inhibitors and Activators, pp. 253-280. , Supuran, C. T., Scozzafava, A., Conway, J., Eds.
CRC Press: Boca Raton, F
Supuran, C.T., Scozzafava, A., Casini, A., Carbonic anhydrase inibitors (2003) Med. Res. Rev., 23, pp. 146-189
Casini, A., Scozzafava, A., Mastrolorenzo, A., Supuran, C.T., Sulfonamides and sulfonylated derivatives as anticancer agents (2002) Curr. Cancer Drug Targets, 2, pp. 55-75
Wykoff, C.C., Beasley, N.J., Watson, P.H., Turner, K.J., Pastorek, J., Sibtain, A., Wilson, G.D., Harris, A.L., Hypoxia-inducible regulation of tumor-associated carbonic anhydrases (2000) Cancer Res., 60, pp. 7075-7083
Potter, C.P.S., Harris, A.L., Diagnostics, prognostics and therapeutic implications of carbonic anhydrases in cancer (2003) Br. J. Cancer, 89, pp. 2-7
Jain, R.K., Normalization of tumor vasculature: An emerging concept in antiangiogenic therapy (2005) Science, 307, pp. 58-62
Pastorek, J., Pastorekova, S., Callebaut, I., Mornon, J.P., Zelnik, V., Opavsky, R., Zatovicova, M., Kettmann, R., 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. 2788-2888
Opavský, R., Pastorekova, S., Zelnik, V., Gibadulinova, A., Stanbridge, E.J., Zavada, J., Kettmann, R., Pastorek, J., Human MN/CA9 gene, a novel member of the carbonic anhydrase family: Structure and exon to protein domain relationship (1996) Genomics, 33, pp. 480-487
Maxwell, P.H., Wiesener, M.S., Chang, G.W., Clifford, S.C., Vaux, E.C., Cockman, M.E., Wykoff, C.C., Ratcliffe, P.J., The tumour suppressor protein VHL targets hypoxia-inducible factors for oxygen-dependent proteolysis (1999) Nature, 399, pp. 271-275
Epstein, A.C.R., Gleadle, J.M., McNeil, L.A., C. elegans EGL-9 and mammalian homologs define a family of dioxygenases that regulate HIF by prolyl hydroxylation (2001) Cell, 107, pp. 43-54
Ratcliffe, P.J., Pugh, C.W., Maxwell, P.H., Targeting tumors through the HIF system (2000) Nat. Med., 6, pp. 1315-1316
Jaakkola, P., Mole, D.R., Tian, Y.M., Wilson, M.I., Gielbert, J., Gaskell, S.J., Kriegsheim, A.V., Ratcliffe, P.J., Targeting of HIF-α to the von Hippel Lindau ubiquitilation complex by O2-regulated prolyl hydroxylation (2001) Science, 292, pp. 468-472
Semenza, G.L., Targeting HIF-1 for cancer therapy (2003) Nat. Rev. Cancer, 3, pp. 721-732
Svastova, E., Hulikova, A., Rafajova, M., Zatovicova, 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
Cecchi, A., Hulikova, A., Pastorek, J., Pastorekova, S., Scozzafava, A., Winum, J.-Y., Montero, J.-L., Supuran, C.T., 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 (2005) J. Med. Chem., 48, pp. 4834-4841
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Carbonic anhydrase inhibitors: Hypoxia-activatable sulfonamides incorporating disulfide bonds that target the tumor-associated isoform IX
An approach for designing bioreductive, hypoxia-activatable carbonic anhydrase (CA, EC 4.2.1.1) inhibitors targeting the tumor-associated isoforms is reported. Sulfonamides incorporating 3,3′-dithiodipropionamide/2, 2′-dithiodibenzamido moieties were prepared and reduced enzymatically/chemically in conditions present in hypoxic tumors, leading to thiols. The X-ray crystal structure of the most promising compound, 4-(2-mercaptophenylcarboxamido)benzenesulfonamide, which as disulfide showed a K1 against hCA IX of 653 nM (in reduced form of 9.1 nM), in adduct with hCA II showed the inhibitor making favorable interactions with Gln92, Val121, Phe131, Leu198, Thr199, Thr200, Pro201, and Pro202, whereas the sulfamoyl moiety was coordinated to the Zn2+ ion. The same interactions were preserved in the adduct with hCA IX, but in addition, a hydrogen bond between the SH moiety of the inhibitor and the amide nitrogen of Gln67 was evidenced, which may explain the almost 2 times more effective inhibition of the tumor-associated isozyme over the cytosolic isoform. © 2006 American Chemical Society.
An approach for designing bioreductive, hypoxia-activatable carbonic anhydrase (CA, EC 4.2.1.1) inhibitors targeting the tumor-associated isoforms is reported. Sulfonamides incorporating 3,3′-dithiodipropionamide/2, 2′-dithiodibenzamido moieties were prepared and reduced enzymatically/chemically in conditions present in hypoxic tumors, leading to thiols. The X-ray crystal structure of the most promising compound, 4-(2-mercaptophenylcarboxamido)benzenesulfonamide, which as disulfide showed a K1 against hCA IX of 653 nM (in reduced form of 9.1 nM), in adduct with hCA II showed the inhibitor making favorable interactions with Gln92, Val121, Phe131, Leu198, Thr199, Thr200, Pro201, and Pro202, whereas the sulfamoyl moiety was coordinated to the Zn2+ ion. The same interactions were preserved in the adduct with hCA IX, but in addition, a hydrogen bond between the SH moiety of the inhibitor and the amide nitrogen of Gln67 was evidenced, which may explain the almost 2 times more effective inhibition of the tumor-associated isozyme over the cytosolic isoform. © 2006 American Chemical Society.
Carbonic anhydrase inhibitors: Hypoxia-activatable sulfonamides incorporating disulfide bonds that target the tumor-associated isoform IX
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Carbonic anhydrase inhibitors: Hypoxia-activatable sulfonamides incorporating disulfide bonds that target the tumor-associated isoform IX
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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 (441 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, Truppo E, Supuran CT, Alterio V, Dathan N, Bootorabi F, Parkkila S, Monti SM, De Simone G
* Crystal structure of the C183S/C217S mutant of human CA VII in complex with acetazolamide (325 views)
Bioorg Med Chem Lett (ISSN: 0960-894x), 2010 Sep 1; 20(17): 5023-5026.
Impact Factor: 2.661
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Turi I, Kállay C, Szikszai D, Pappalardo G, Di Natale G, De Bona P, Rizzarelli E, Sóvágó I
* Nickel(II) complexes of the multihistidine peptide fragments of human prion protein (480 views)
J Chem Res (ISSN: 1873-3344, 0162-0134, 0162-0134print), 2010 Sep; 104(8): 885-891.
Impact Factor: 3.317
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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 (471 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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Kapucu OL, Nobili F, Varrone A, Booij J, Vander Borght T, Nagren K, Darcourt J, Tatsch K, Van Laere KJ
* EANM procedure guideline for brain perfusion SPECT using Tc-99m-labelled radiopharmaceuticals, version (571 views)
Eur J Nucl Med (ISSN: 1619-7070, 1619-7089, 0340-6997), 2009 Dec; 36(12): 2093-2102.
Impact Factor: 4.531
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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 (462 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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Alterio V, Hilvo M, Di Fiore A, Supuran CT, Pan P, Parkkila S, Scaloni A, Pastorek J, Pastorekova S, Pedone C, Scozzafava A, Monti SM, De Simone G
* Crystal structure of the catalytic domain of the tumor-associated human carbonic anhydrase IX (571 views)
P Natl Acad Sci Usa (ISSN: 0027-8424, 1091-6490, 0027-8424print), 2009 Sep 22; 106(38): 16233-16238.
Impact Factor: 9.432
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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 (527 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 (823 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 (560 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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De Simone G, Di Fiore A, Supuran CT
* Are carbonic anhydrase inhibitors suitable for obtaining antiobesity drugs? (472 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
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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 (479 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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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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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 (474 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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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 (310 views)
Bioorganic & Medicinal Chemistry Letters (ISSN: 0960-894x), 2006 Dec 15; 16(24): 6204-6208.
Impact Factor: 2.538
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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 (484 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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Menchise V, De Simone G, Alterio V, Di Fiore A, Pedone C, Scozzafava A, Supuran CT
* 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 (481 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2005 Sep 8; 48(18): 5721-5727.
Impact Factor: 4.926
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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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Soricelli A, Postiglione A, Cuocolo A, De Chiara S, Ruocco A, Brunetti A, Salvatore M, Ell PJ
EFFECT OF ADENOSINE ON CEREBRAL BLOOD-FLOW AS EVALUATED BY SINGLE-PHOTON EMISSION COMPUTED-TOMOGRAPHY IN NORMAL SUBJECTS AND IN PATIENTS WITH OCCLUSIVE CAROTID DISEASE - A COMPARISON WITH ACETAZOLAMIDE (256 views)
Stroke (ISSN: 0039-2499), 1995 Sep; 26(9): 1572-1576.
Impact Factor: 4.323
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Mancini M, De Chiara S, Ferrara LA, Gallotta G, Postiglione A
TRANSCRANIAL DOPPLER EVALUATION OF CEREBROVASCULAR REACTIVITY TO ACETAZOLAMIDE IN NORMAL SUBJECTS (665 views)
15th World Congress Angiology Rome, 1989; 20(4): 284-284.
Impact Factor: 0
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* Inhibition of the β-carbonic anhydrase from the protozoan pathogen Trichomonas vaginalis with sulphonamides (148 views)
J Enzym Inhib Med Ch (ISSN: 1475-6366linking, 1475-6374electronic), 2021 Dec; 36(1): 329-334.
Impact Factor: 4.673
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Alterio V, Langella E, Buonanno M, Esposito D, Nocentini A, Berrino E, Bua S, Polentarutti M, Supuran CT, Monti SM, De Simone G
* Zeta-carbonic anhydrases show CS(2) hydrolase activity: A new metabolic carbon acquisition pathway in diatoms? (26 views)
Comput Struct Biotechnol J (ISSN: 2001-0370linking), 2021 Jun 5; 19: 3427-3436.
Impact Factor: 7.271
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De Simone G, Bua S, Supuran CT, Alterio V
* Benzyl alcohol inhibits carbonic anhydrases by anchoring to the zinc coordinated water molecule (11 views)
Biochem Biophys Res Commun (ISSN: 0006-291xlinking), 2021 Apr 9; 548: 217-221.
Impact Factor: 3.575
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De Simone G, Angeli A, Bozdag M, Supuran CT, Winum JY, Monti SM, Alterio V
* 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 (825 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 (301 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) (573 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 (406 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 (367 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 (423 views)
Biomed Res Int (ISSN: 2314-6133, 2314-6141), 2015; 2015: 174178-174178.
Impact Factor: 2.134
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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" (449 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 (416 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 (546 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) (468 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? (452 views)
Chem Rev (ISSN: 0009-2665), 2012 Sep; 112(8): 4421-4468.
Impact Factor: 41.298
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Jószai V, Turi I, Kállay C, Pappalardo G, Di Natale G, Rizzarelli E, Sóvágó I
* Mixed metal copper(II)-nickel(II) and copper(II)-zinc(II) complexes of multihistidine peptide fragments of human prion protein (481 views)
J Chem Res (ISSN: 1873-3344, 0162-0134, 0162-0134print), 2012 Jul; 112: 17-24.
Impact Factor: 3.197
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De Simone G, Supuran CT
* (In)organic anions as carbonic anhydrase inhibitors (378 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 (441 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, Truppo E, Supuran CT, Alterio V, Dathan N, Bootorabi F, Parkkila S, Monti SM, De Simone G
* Crystal structure of the C183S/C217S mutant of human CA VII in complex with acetazolamide (325 views)
Bioorg Med Chem Lett (ISSN: 0960-894x), 2010 Sep 1; 20(17): 5023-5026.
Impact Factor: 2.661
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Turi I, Kállay C, Szikszai D, Pappalardo G, Di Natale G, De Bona P, Rizzarelli E, Sóvágó I
* Nickel(II) complexes of the multihistidine peptide fragments of human prion protein (480 views)
J Chem Res (ISSN: 1873-3344, 0162-0134, 0162-0134print), 2010 Sep; 104(8): 885-891.
Impact Factor: 3.317
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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 (471 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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Kapucu OL, Nobili F, Varrone A, Booij J, Vander Borght T, Nagren K, Darcourt J, Tatsch K, Van Laere KJ
* EANM procedure guideline for brain perfusion SPECT using Tc-99m-labelled radiopharmaceuticals, version (571 views)
Eur J Nucl Med (ISSN: 1619-7070, 1619-7089, 0340-6997), 2009 Dec; 36(12): 2093-2102.
Impact Factor: 4.531
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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 (462 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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Alterio V, Hilvo M, Di Fiore A, Supuran CT, Pan P, Parkkila S, Scaloni A, Pastorek J, Pastorekova S, Pedone C, Scozzafava A, Monti SM, De Simone G
* Crystal structure of the catalytic domain of the tumor-associated human carbonic anhydrase IX (571 views)
P Natl Acad Sci Usa (ISSN: 0027-8424, 1091-6490, 0027-8424print), 2009 Sep 22; 106(38): 16233-16238.
Impact Factor: 9.432
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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 (527 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 (823 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 (560 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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De Simone G, Di Fiore A, Supuran CT
* Are carbonic anhydrase inhibitors suitable for obtaining antiobesity drugs? (472 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
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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 (479 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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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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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 (474 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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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 (310 views)
Bioorganic & Medicinal Chemistry Letters (ISSN: 0960-894x), 2006 Dec 15; 16(24): 6204-6208.
Impact Factor: 2.538
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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 (484 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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Menchise V, De Simone G, Alterio V, Di Fiore A, Pedone C, Scozzafava A, Supuran CT
* 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 (481 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2005 Sep 8; 48(18): 5721-5727.
Impact Factor: 4.926
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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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Soricelli A, Postiglione A, Cuocolo A, De Chiara S, Ruocco A, Brunetti A, Salvatore M, Ell PJ
EFFECT OF ADENOSINE ON CEREBRAL BLOOD-FLOW AS EVALUATED BY SINGLE-PHOTON EMISSION COMPUTED-TOMOGRAPHY IN NORMAL SUBJECTS AND IN PATIENTS WITH OCCLUSIVE CAROTID DISEASE - A COMPARISON WITH ACETAZOLAMIDE (256 views)
Stroke (ISSN: 0039-2499), 1995 Sep; 26(9): 1572-1576.
Impact Factor: 4.323
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Mancini M, De Chiara S, Ferrara LA, Gallotta G, Postiglione A
TRANSCRANIAL DOPPLER EVALUATION OF CEREBROVASCULAR REACTIVITY TO ACETAZOLAMIDE IN NORMAL SUBJECTS (665 views)
15th World Congress Angiology Rome, 1989; 20(4): 284-284.
Impact Factor: 0
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54 Records (53 excluding Abstracts).
Total impact factor: 254.525 (254.525 excluding Abstracts).
Total 5 year impact factor: 248.807 (248.807 excluding Abstracts).
Total impact factor: 254.525 (254.525 excluding Abstracts).
Total 5 year impact factor: 248.807 (248.807 excluding Abstracts).
474 views. Last view on Thursday 16 February 2023, 7:54:22
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