Probing Molecular Interactions between Human Carbonic Anhydrases (hCAs) and a Novel Class of Benzenesulfonamides (386 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2017 May 25; 60(10): 4316-4326.
Export to BibTeX Export to EndNote
Paper type: Journal Article, Journal Paper,
Impact factor: 6.253, 5-year impact factor: 5.9
Url: doi: 10.1021/acs.jmedchem.7b00264
Keywords: 4 (1 Phenyl 6 Propoxy 3, 4 Dihydro 1h Isoquinoline 2 Carbonyl)benzenesulfonamide, 4 (6 Hydroxy 1 Phenyl 3, 4 (6 Methoxy 1 Phenyl 3, 7 Dihydroxy 1 Phenyl 3, 7 Dimethoxy 1 Phenyl 3, 4 [1 (4 Bromophenyl) 6, 4 Dihydro 1h Isoquinoline 2 Carbonyl]benzenesulfonamide, 4 [1 (4 Chlorophenyl) 6, 4 Dihydro 1h Isoquinoline 2 Carbonyl]benzesulfonamide, 4 [1 (4 Fluorophenyl) 6, 7 Dihydroxy 1 (4 Fluorophenyl) 3, Benzenesulfonamide Derivative, Carbonate Dehydratase Inhibitor, Unclassified Drug, Isoprotein, Isoquinoline Derivative, Article, Drug Design, Drug Structure, Drug Synthesis, Elemental Analysis, Enantiomer, Enantioselectivity, Enzyme Active Site, High Performance Liquid Chromatography, Human, Hydrogen Bond, Molecular Docking, Molecular Interaction, Molecular Model, Proton Nuclear Magnetic Resonance, Racemic Mixture, X Ray Crystallography, Chemistry, Metabolism, Structure Activity Relation, Carbonic Anhydrase Inhibitors, X-Ray, Molecular Docking Simulation, Protein Isoforms, Structure-Activity Relationship,
Affiliations:
*** IBB - CNR ***
Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali (CHIBIOFARAM), Università degli Studi di Messina, Viale Annunziata, Messina, I-98168, Italy
Istituto di Biostrutture e Bioimmagini-CNR, Via Mezzocannone 16, Napoli, I-80134, Italy
Dipartimento NEUROFARBA, Università di Firenze, Via Ugo Schiff 6, Sesto Fiorentino, I-50019, Italy
Centro Nazionale Per il Controllo e la Valutazione Dei Farmaci, Istituto Superiore di Sanità, V.le Regina Elena 299, Roma, I-00161, Italy
References:
Supuran, C.T., Diuretics: from classical carbonic anhydrase inhibitors to novel applications of the sulfonamides (2008) Curr. Pharm. Des., 14, pp. 641-64
Supuran, C.T., Scozzafava, A., Mincione, F., The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents (2008) Curr. Pharm. Des., 14, pp. 649-654
Di Fiore, A., Supuran, C.T., De Simone, G., Are carbonic anhydrase inhibitors suitable for obtaining antiobesity drugs? (2008) Curr. Pharm. Des., 14, pp. 655-660
Thiry, A., Dogne, J.M., Supuran, C.T., Masereel, B., Carbonic anhydrase inhibitors as anticonvulsant agents (2007) Curr. Top. Med. Chem., 7, pp. 855-864
Supuran, C.T., Inhibition of bacterial carbonic anhydrases and zinc proteases: from orphan targets to innovative new antibiotic drugs (2012) Curr. Med. Chem., 19, pp. 831-844
Bao, B., Groves, K., Zhang, J., Handy, E., Kennedy, P., Cuneo, G., Supuran, C.T., Peterson, J.D., In vivo imaging and quantification of carbonic anhydrase IX expression as an endogenous biomarker of tumor hypoxia (2012) PLoS One, 7, p. e50860
Supuran, C.T., Carbonic anhydrase inhibitors as emerging drugs for the treatment of obesity (2012) Expert Opin. Emerging Drugs, 17, pp. 11-15
Thiry, A., Masereel, B., Dogne, J.M., Supuran, C.T., Wouters, J., Michaux, C., Exploration of the binding mode of indanesulfonamides as selective inhibitors of human carbonic anhydrase type VII by targeting Lys 91 (2007) ChemMedChem, 2, pp. 1273-1280
De Simone, G., Scozzafava, A., Supuran, C.T., Which carbonic anhydrases are targeted by the antiepileptic sulfonamides and sulfamates? (2009) Chem. Biol. Drug Des., 74, pp. 317-321
Monti, S.M., Supuran, C.T., De Simone, G., Carbonic anhydrase IX as a target for designing novel anticancer drugs (2012) Curr. Med. Chem., 19, pp. 821-830
Nishimori, I., Vullo, D., Minakuchi, T., Scozzafava, A., Capasso, C., Supuran, C.T., Restoring catalytic activity to the human carbonic anhydrase (CA) related proteins VIII, X and XI affords isoforms with high catalytic efficiency and susceptibility to anion inhibition (2013) Bioorg. Med. Chem. Lett., 23, pp. 256-260
Said, H.M., Supuran, C.T., Hageman, C., Staab, A., Polat, B., Katzer, A., Scozzafava, A., Vordermark, D., Modulation of carbonic anhydrase 9 (CA9) in human brain cancer (2010) Curr. Pharm. Des., 16, pp. 3288-3299
Guler, O.O., De Simone, G., Supuran, C.T., Drug design studies of the novel antitumor targets carbonic anhydrase IX and XII (2010) Curr. Med. Chem., 17, pp. 1516-1526
Akurathi, V., Dubois, L., Lieuwes, N.G., Chitneni, S.K., Cleynhens, B.J., Vullo, D., Supuran, C.T., Bormans, G.M., Synthesis and biological evaluation of a 99mTc-labelled sulfonamide conjugate for in vivo visualization of carbonic anhydrase IX expression in tumor hypoxia (2010) Nucl. Med. Biol., 37, pp. 557-564
Genis, C., Sippel, K.H., Case, N., Cao, W., Avvaru, B.S., Tartaglia, L.J., Govindasamy, L., McKenna, R., Design of a carbonic anhydrase IX active-site mimic to screen inhibitors for possible anticancer properties (2009) Biochemistry, 48, pp. 1322-1331
Thiry, A., Supuran, C.T., Masereel, B., Dogne, J.M., Recent developments of carbonic anhydrase inhibitors as potential anticancer drugs (2008) J. Med. Chem., 51, pp. 3051-3056
Pastorekova, S., Kopacek, J., Pastorek, J., Carbonic anhydrase inhibitors and the management of cancer (2007) Curr. Top. Med. Chem., 7, pp. 865-878
De Simone, G., Vitale, R.M., Di Fiore, A., Pedone, C., Scozzafava, A., Montero, J.L., Winum, J.Y., Supuran, C.T., Carbonic anhydrase inhibitors: hypoxia-activatable sulfonamides incorporating disulfide bonds that target the tumor-associated isoform IX (2006) J. Med. Chem., 49, pp. 5544-5551
Meijer, T.W., Bussink, J., Zatovicova, M., Span, P.N., Lok, J., Supuran, C.T., Kaanders, J.H., Tumor microenvironmental changes induced by the sulfamate carbonic anhydrase IX inhibitor S4 in a laryngeal tumor model (2014) PLoS One, 9, p. e108068
Krall, N., Pretto, F., Decurtins, W., Bernardes, G.J., Supuran, C.T., Neri, D., A small-molecule drug conjugate for the treatment of carbonic anhydrase IX expressing tumors (2014) Angew. Chem., Int. Ed., 53, pp. 4231-4235
Parkkila, S., Parkkila, A.K., Rajaniemi, H., Shah, G.N., Grubb, J.H., Waheed, A., Sly, W.S., Expression of membrane-associated carbonic anhydrase XIV on neurons and axons in mouse and human brain (2001) Proc. Natl. Acad. Sci. U. S. A., 98, pp. 1918-1923
Alterio, V., Pan, P., Parkkila, S., Buonanno, M., Supuran, C.T., Monti, S.M., De Simone, G., The structural comparison between membrane-associated human carbonic anhydrases provides insights into drug design of selective inhibitors (2014) Biopolymers, 101, pp. 769-778
Alterio, V., Di Fiore, A., D’Ambrosio, K., Supuran, C.T., De Simone, G., Multiple binding modes of inhibitors to carbonic anhydrases: how to design specific drugs targeting 15 different isoforms? (2012) Chem. Rev., 112, pp. 4421-4468
Carta, F., Scozzafava, A., Supuran, C.T., Sulfonamides: a patent review (2008 - 2012) (2012) Expert Opin. Ther. Pat., 22, pp. 747-758
D’Ambrosio, K., Smaine, F.Z., Carta, F., De Simone, G., Winum, J.Y., Supuran, C.T., Development of potent carbonic anhydrase inhibitors incorporating both sulfonamide and sulfamide groups (2012) J. Med. Chem., 55, pp. 6776-6783
Marini, A.M., Maresca, A., Aggarwal, M., Orlandini, E., Nencetti, S., Da Settimo, F., Salerno, S., Supuran, C.T., Tricyclic sulfonamides incorporating benzothiopyrano[4,3-c]pyrazole and pyridothiopyrano[4,3-c]pyrazole effectively inhibit alpha- and beta-carbonic anhydrase: X-ray crystallography and solution investigations on 15 isoforms (2012) J. Med. Chem., 55, pp. 9619-9629
Schulze Wischeler, J., Innocenti, A., Vullo, D., Agrawal, A., Cohen, S.M., Heine, A., Supuran, C.T., Klebe, G., Bidentate Zinc chelators for alpha-carbonic anhydrases that produce a trigonal bipyramidal coordination geometry (2010) ChemMedChem, 5, pp. 1609-1615
Winum, J.Y., Scozzafava, A., Montero, J.L., Supuran, C.T., Therapeutic potential of sulfamides as enzyme inhibitors (2006) Med. Res. Rev., 26, pp. 767-792
Pala, N., Micheletto, L., Sechi, M., Aggarwal, M., Carta, F., McKenna, R., Supuran, C.T., Carbonic anhydrase inhibition with benzenesulfonamides and tetrafluorobenzenesulfonamides obtained via click chemistry (2014) ACS Med. Chem. Lett., 5, pp. 927-930
Carta, F., Supuran, C.T., Scozzafava, A., Sulfonamides and their isosters as carbonic anhydrase inhibitors (2014) Future Med. Chem., 6, pp. 1149-1165
Gitto, R., Agnello, S., Ferro, S., De Luca, L., Vullo, D., Brynda, J., Mader, P., Chimirri, A., Identification of 3,4-Dihydroisoquinoline-2(1H)-sulfonamides as potent carbonic anhydrase inhibitors: synthesis, biological evaluation, and enzyme--ligand X-ray studies (2010) J. Med. Chem., 53, pp. 2401-2408
Mader, P., Brynda, J., Gitto, R., Agnello, S., Pachl, P., Supuran, C.T., Chimirri, A., Rezacova, P., Structural basis for the interaction between carbonic anhydrase and 1,2,3,4-tetrahydroisoquinolin-2-ylsulfonamides (2011) J. Med. Chem., 54, pp. 2522-2526
Fisher, S.Z., Govindasamy, L., Boyle, N., Agbandje-McKenna, M., Silverman, D.N., Blackburn, G.M., McKenna, R., X-ray crystallographic studies reveal that the incorporation of spacer groups in carbonic anhydrase inhibitors causes alternate binding modes (2006) Acta Crystallogr., Sect. F: Struct. Biol. Cryst. Commun., 62, pp. 618-622
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
Menchise, V., De Simone, G., Alterio, V., Di Fiore, A., Pedone, C., Scozzafava, A., Supuran, C.T., 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 (2005) J. Med. Chem., 48, pp. 5721-5727
Bozdag, M., Ferraroni, M., Nuti, E., Vullo, D., Rossello, A., Carta, F., Scozzafava, A., Supuran, C.T., Combining the tail and the ring approaches for obtaining potent and isoform-selective carbonic anhydrase inhibitors: solution and X-ray crystallographic studies (2014) Bioorg. Med. Chem., 22, pp. 334-340
Di Fiore, A., Monti, S.M., Hilvo, M., Parkkila, S., Romano, V., Scaloni, A., Pedone, C., De Simone, G., Crystal structure of human carbonic anhydrase XIII and its complex with the inhibitor acetazolamide (2009) Proteins: Struct., Funct., Genet., 74, pp. 164-175
Alterio, V., Hilvo, M., Di Fiore, A., Supuran, C.T., Pan, P., Parkkila, S., Scaloni, A., De Simone, G., Crystal structure of the catalytic domain of the tumor-associated human carbonic anhydrase IX (2009) Proc. Natl. Acad. Sci. U. S. A., 106, pp. 16233-16238
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J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2017 May 25; 60(10): 4316-4326.
Export to BibTeX Export to EndNote
Paper type: Journal Article, Journal Paper,
Impact factor: 6.253, 5-year impact factor: 5.9
Url: doi: 10.1021/acs.jmedchem.7b00264
Keywords: 4 (1 Phenyl 6 Propoxy 3, 4 Dihydro 1h Isoquinoline 2 Carbonyl)benzenesulfonamide, 4 (6 Hydroxy 1 Phenyl 3, 4 (6 Methoxy 1 Phenyl 3, 7 Dihydroxy 1 Phenyl 3, 7 Dimethoxy 1 Phenyl 3, 4 [1 (4 Bromophenyl) 6, 4 Dihydro 1h Isoquinoline 2 Carbonyl]benzenesulfonamide, 4 [1 (4 Chlorophenyl) 6, 4 Dihydro 1h Isoquinoline 2 Carbonyl]benzesulfonamide, 4 [1 (4 Fluorophenyl) 6, 7 Dihydroxy 1 (4 Fluorophenyl) 3, Benzenesulfonamide Derivative, Carbonate Dehydratase Inhibitor, Unclassified Drug, Isoprotein, Isoquinoline Derivative, Article, Drug Design, Drug Structure, Drug Synthesis, Elemental Analysis, Enantiomer, Enantioselectivity, Enzyme Active Site, High Performance Liquid Chromatography, Human, Hydrogen Bond, Molecular Docking, Molecular Interaction, Molecular Model, Proton Nuclear Magnetic Resonance, Racemic Mixture, X Ray Crystallography, Chemistry, Metabolism, Structure Activity Relation, Carbonic Anhydrase Inhibitors, X-Ray, Molecular Docking Simulation, Protein Isoforms, Structure-Activity Relationship,
Affiliations:
*** IBB - CNR ***
Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali (CHIBIOFARAM), Università degli Studi di Messina, Viale Annunziata, Messina, I-98168, Italy
Istituto di Biostrutture e Bioimmagini-CNR, Via Mezzocannone 16, Napoli, I-80134, Italy
Dipartimento NEUROFARBA, Università di Firenze, Via Ugo Schiff 6, Sesto Fiorentino, I-50019, Italy
Centro Nazionale Per il Controllo e la Valutazione Dei Farmaci, Istituto Superiore di Sanità, V.le Regina Elena 299, Roma, I-00161, Italy
References:
Supuran, C.T., Diuretics: from classical carbonic anhydrase inhibitors to novel applications of the sulfonamides (2008) Curr. Pharm. Des., 14, pp. 641-64
Supuran, C.T., Scozzafava, A., Mincione, F., The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents (2008) Curr. Pharm. Des., 14, pp. 649-654
Di Fiore, A., Supuran, C.T., De Simone, G., Are carbonic anhydrase inhibitors suitable for obtaining antiobesity drugs? (2008) Curr. Pharm. Des., 14, pp. 655-660
Thiry, A., Dogne, J.M., Supuran, C.T., Masereel, B., Carbonic anhydrase inhibitors as anticonvulsant agents (2007) Curr. Top. Med. Chem., 7, pp. 855-864
Supuran, C.T., Inhibition of bacterial carbonic anhydrases and zinc proteases: from orphan targets to innovative new antibiotic drugs (2012) Curr. Med. Chem., 19, pp. 831-844
Bao, B., Groves, K., Zhang, J., Handy, E., Kennedy, P., Cuneo, G., Supuran, C.T., Peterson, J.D., In vivo imaging and quantification of carbonic anhydrase IX expression as an endogenous biomarker of tumor hypoxia (2012) PLoS One, 7, p. e50860
Supuran, C.T., Carbonic anhydrase inhibitors as emerging drugs for the treatment of obesity (2012) Expert Opin. Emerging Drugs, 17, pp. 11-15
Thiry, A., Masereel, B., Dogne, J.M., Supuran, C.T., Wouters, J., Michaux, C., Exploration of the binding mode of indanesulfonamides as selective inhibitors of human carbonic anhydrase type VII by targeting Lys 91 (2007) ChemMedChem, 2, pp. 1273-1280
De Simone, G., Scozzafava, A., Supuran, C.T., Which carbonic anhydrases are targeted by the antiepileptic sulfonamides and sulfamates? (2009) Chem. Biol. Drug Des., 74, pp. 317-321
Monti, S.M., Supuran, C.T., De Simone, G., Carbonic anhydrase IX as a target for designing novel anticancer drugs (2012) Curr. Med. Chem., 19, pp. 821-830
Nishimori, I., Vullo, D., Minakuchi, T., Scozzafava, A., Capasso, C., Supuran, C.T., Restoring catalytic activity to the human carbonic anhydrase (CA) related proteins VIII, X and XI affords isoforms with high catalytic efficiency and susceptibility to anion inhibition (2013) Bioorg. Med. Chem. Lett., 23, pp. 256-260
Said, H.M., Supuran, C.T., Hageman, C., Staab, A., Polat, B., Katzer, A., Scozzafava, A., Vordermark, D., Modulation of carbonic anhydrase 9 (CA9) in human brain cancer (2010) Curr. Pharm. Des., 16, pp. 3288-3299
Guler, O.O., De Simone, G., Supuran, C.T., Drug design studies of the novel antitumor targets carbonic anhydrase IX and XII (2010) Curr. Med. Chem., 17, pp. 1516-1526
Akurathi, V., Dubois, L., Lieuwes, N.G., Chitneni, S.K., Cleynhens, B.J., Vullo, D., Supuran, C.T., Bormans, G.M., Synthesis and biological evaluation of a 99mTc-labelled sulfonamide conjugate for in vivo visualization of carbonic anhydrase IX expression in tumor hypoxia (2010) Nucl. Med. Biol., 37, pp. 557-564
Genis, C., Sippel, K.H., Case, N., Cao, W., Avvaru, B.S., Tartaglia, L.J., Govindasamy, L., McKenna, R., Design of a carbonic anhydrase IX active-site mimic to screen inhibitors for possible anticancer properties (2009) Biochemistry, 48, pp. 1322-1331
Thiry, A., Supuran, C.T., Masereel, B., Dogne, J.M., Recent developments of carbonic anhydrase inhibitors as potential anticancer drugs (2008) J. Med. Chem., 51, pp. 3051-3056
Pastorekova, S., Kopacek, J., Pastorek, J., Carbonic anhydrase inhibitors and the management of cancer (2007) Curr. Top. Med. Chem., 7, pp. 865-878
De Simone, G., Vitale, R.M., Di Fiore, A., Pedone, C., Scozzafava, A., Montero, J.L., Winum, J.Y., Supuran, C.T., Carbonic anhydrase inhibitors: hypoxia-activatable sulfonamides incorporating disulfide bonds that target the tumor-associated isoform IX (2006) J. Med. Chem., 49, pp. 5544-5551
Meijer, T.W., Bussink, J., Zatovicova, M., Span, P.N., Lok, J., Supuran, C.T., Kaanders, J.H., Tumor microenvironmental changes induced by the sulfamate carbonic anhydrase IX inhibitor S4 in a laryngeal tumor model (2014) PLoS One, 9, p. e108068
Krall, N., Pretto, F., Decurtins, W., Bernardes, G.J., Supuran, C.T., Neri, D., A small-molecule drug conjugate for the treatment of carbonic anhydrase IX expressing tumors (2014) Angew. Chem., Int. Ed., 53, pp. 4231-4235
Parkkila, S., Parkkila, A.K., Rajaniemi, H., Shah, G.N., Grubb, J.H., Waheed, A., Sly, W.S., Expression of membrane-associated carbonic anhydrase XIV on neurons and axons in mouse and human brain (2001) Proc. Natl. Acad. Sci. U. S. A., 98, pp. 1918-1923
Alterio, V., Pan, P., Parkkila, S., Buonanno, M., Supuran, C.T., Monti, S.M., De Simone, G., The structural comparison between membrane-associated human carbonic anhydrases provides insights into drug design of selective inhibitors (2014) Biopolymers, 101, pp. 769-778
Alterio, V., Di Fiore, A., D’Ambrosio, K., Supuran, C.T., De Simone, G., Multiple binding modes of inhibitors to carbonic anhydrases: how to design specific drugs targeting 15 different isoforms? (2012) Chem. Rev., 112, pp. 4421-4468
Carta, F., Scozzafava, A., Supuran, C.T., Sulfonamides: a patent review (2008 - 2012) (2012) Expert Opin. Ther. Pat., 22, pp. 747-758
D’Ambrosio, K., Smaine, F.Z., Carta, F., De Simone, G., Winum, J.Y., Supuran, C.T., Development of potent carbonic anhydrase inhibitors incorporating both sulfonamide and sulfamide groups (2012) J. Med. Chem., 55, pp. 6776-6783
Marini, A.M., Maresca, A., Aggarwal, M., Orlandini, E., Nencetti, S., Da Settimo, F., Salerno, S., Supuran, C.T., Tricyclic sulfonamides incorporating benzothiopyrano[4,3-c]pyrazole and pyridothiopyrano[4,3-c]pyrazole effectively inhibit alpha- and beta-carbonic anhydrase: X-ray crystallography and solution investigations on 15 isoforms (2012) J. Med. Chem., 55, pp. 9619-9629
Schulze Wischeler, J., Innocenti, A., Vullo, D., Agrawal, A., Cohen, S.M., Heine, A., Supuran, C.T., Klebe, G., Bidentate Zinc chelators for alpha-carbonic anhydrases that produce a trigonal bipyramidal coordination geometry (2010) ChemMedChem, 5, pp. 1609-1615
Winum, J.Y., Scozzafava, A., Montero, J.L., Supuran, C.T., Therapeutic potential of sulfamides as enzyme inhibitors (2006) Med. Res. Rev., 26, pp. 767-792
Pala, N., Micheletto, L., Sechi, M., Aggarwal, M., Carta, F., McKenna, R., Supuran, C.T., Carbonic anhydrase inhibition with benzenesulfonamides and tetrafluorobenzenesulfonamides obtained via click chemistry (2014) ACS Med. Chem. Lett., 5, pp. 927-930
Carta, F., Supuran, C.T., Scozzafava, A., Sulfonamides and their isosters as carbonic anhydrase inhibitors (2014) Future Med. Chem., 6, pp. 1149-1165
Gitto, R., Agnello, S., Ferro, S., De Luca, L., Vullo, D., Brynda, J., Mader, P., Chimirri, A., Identification of 3,4-Dihydroisoquinoline-2(1H)-sulfonamides as potent carbonic anhydrase inhibitors: synthesis, biological evaluation, and enzyme--ligand X-ray studies (2010) J. Med. Chem., 53, pp. 2401-2408
Mader, P., Brynda, J., Gitto, R., Agnello, S., Pachl, P., Supuran, C.T., Chimirri, A., Rezacova, P., Structural basis for the interaction between carbonic anhydrase and 1,2,3,4-tetrahydroisoquinolin-2-ylsulfonamides (2011) J. Med. Chem., 54, pp. 2522-2526
Fisher, S.Z., Govindasamy, L., Boyle, N., Agbandje-McKenna, M., Silverman, D.N., Blackburn, G.M., McKenna, R., X-ray crystallographic studies reveal that the incorporation of spacer groups in carbonic anhydrase inhibitors causes alternate binding modes (2006) Acta Crystallogr., Sect. F: Struct. Biol. Cryst. Commun., 62, pp. 618-622
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
Menchise, V., De Simone, G., Alterio, V., Di Fiore, A., Pedone, C., Scozzafava, A., Supuran, C.T., 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 (2005) J. Med. Chem., 48, pp. 5721-5727
Bozdag, M., Ferraroni, M., Nuti, E., Vullo, D., Rossello, A., Carta, F., Scozzafava, A., Supuran, C.T., Combining the tail and the ring approaches for obtaining potent and isoform-selective carbonic anhydrase inhibitors: solution and X-ray crystallographic studies (2014) Bioorg. Med. Chem., 22, pp. 334-340
Di Fiore, A., Monti, S.M., Hilvo, M., Parkkila, S., Romano, V., Scaloni, A., Pedone, C., De Simone, G., Crystal structure of human carbonic anhydrase XIII and its complex with the inhibitor acetazolamide (2009) Proteins: Struct., Funct., Genet., 74, pp. 164-175
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Probing Molecular Interactions between Human Carbonic Anhydrases (hCAs) and a Novel Class of Benzenesulfonamides
On the basis of X-ray crystallographic studies of the complex of hCA II
with 4-(3,4-dihydro-1H-isoquinoline-2-carbonyl)benzenesulfonamide (3)
(PDB code 4Z1J ), a novel series of
4-(1-aryl-3,4-dihydro-1H-isoquinolin-2-carbonyl)benzenesulfonamides
(23-33) was designed. Specifically, our idea was to improve the
selectivity toward druggable isoforms through the introduction of
additional hydrophobic/hydrophilic functionalities. Among the
synthesized and tested compounds, the
(R,S)-4-(6,7-dihydroxy-1-phenyl-3,4-tetrahydroisoquinoline-1H-2-carbonyl)benzenesulfonamide
(30) exhibited a remarkable inhibition for the brain-expressed hCA VII
(K i = 0.20 nM) and selectivity over wider distributed hCA I
and hCA II isoforms. By enantioselective HPLC, we solved the racemic
mixture and ascertained that the two enantiomers (30a and 30b) are
equiactive inhibitors for hCA VII. Crystallographic and docking studies
revealed the main interactions of these inhibitors into the carbonic
anhydrase (CA) catalytic site, thus highlighting the relevant role of
nonpolar contacts for this class of hCA inhibitors.
On the basis of X-ray crystallographic studies of the complex of hCA II
with 4-(3,4-dihydro-1H-isoquinoline-2-carbonyl)benzenesulfonamide (3)
(PDB code 4Z1J ), a novel series of
4-(1-aryl-3,4-dihydro-1H-isoquinolin-2-carbonyl)benzenesulfonamides
(23-33) was designed. Specifically, our idea was to improve the
selectivity toward druggable isoforms through the introduction of
additional hydrophobic/hydrophilic functionalities. Among the
synthesized and tested compounds, the
(R,S)-4-(6,7-dihydroxy-1-phenyl-3,4-tetrahydroisoquinoline-1H-2-carbonyl)benzenesulfonamide
(30) exhibited a remarkable inhibition for the brain-expressed hCA VII
(K i = 0.20 nM) and selectivity over wider distributed hCA I
and hCA II isoforms. By enantioselective HPLC, we solved the racemic
mixture and ascertained that the two enantiomers (30a and 30b) are
equiactive inhibitors for hCA VII. Crystallographic and docking studies
revealed the main interactions of these inhibitors into the carbonic
anhydrase (CA) catalytic site, thus highlighting the relevant role of
nonpolar contacts for this class of hCA inhibitors.
Probing Molecular Interactions between Human Carbonic Anhydrases (hCAs) and a Novel Class of Benzenesulfonamides
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