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.
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Paper type: Journal Article,
Impact factor: 2.923, 5-year impact factor: 2.869
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-84937521131&partnerID=40&md5=c7d21eb3e9b0a34eefa1986073fd0681
Keywords: Anti-Infective, Bacteria, Beta-Carbonic Anhydrase, Fungi, Pathogenic Microorganism, Protozoa, Schiff Base, Selective Inhibitor, Sulfonamide, 3 Fluorosulfanilamide, 4 (2 Aminoethyl) Benzenesulfonamide, Aldehyde, Bacterial Enzyme, Carbonate Dehydratase, Carbonate Dehydratase Inhibitor, Fungal Enzyme, Protozoal Protein, Unclassified Drug, Antibacterial Activity, Antifungal Activity, Antiprotozoal Activity, Article, Brucella Suis, Cryptococcus Neoformans, Drug Efficacy, Drug Potency, Drug Selectivity, Drug Structure, Drug Synthesis, Drug Targeting, Enzyme Inhibition, Hydrophilicity, Hydrophobicity, Leishmania Chagasi, Nonhuman, Bacteria (microorganisms), Brucella Melitensis Biovar Suis, Filobasidiella Neoformans, Leishmania Donovani Chagasi,
Affiliations:
*** IBB - CNR ***
Università Degli Studi di Firenze, Polo Scientifico, Laboratorio di Chimica Bioinorganica, Via della Lastruccia 3, Sesto Fiorentino (Florence), Italy
Department of Chemistry, College of Science, King Saud University, Riyadh, Saudi Arabia
Istituto di Biostrutture e Bioimmagini-CNR, Via Mezzocannone 16, Napoli, Italy
References:
Cardoso, T., Ribeiro, O., Aragao, I.C., Costa-Pereira, A., Sarmento, A.E., (2012) BMC Infect. Dis., 12, p. 37
Cox, G.M., Mukherjee, J., Cole, G.T., Casadeval, A., Perfect, J.R., (2000) Infect. Immun., 68, p. 443
Cox, G.M., McDade, H.C., Chen, S.C.A., Gottfredsson, M., Wright, L.C., Sorrell, T.C., Leidich, S.D., Perfect, J.R., (2001) Mol. Microbiol., 39, p. 166
Supuran, C.T., (2008) Nat. Rev. Drug Discov., 7, p. 168
Joseph, P., Turtaut, F., Ouahrani-Bettache, S., Montero, J.L., Nishimori, I., Minakuchi, T., Vullo, D., Cloning, (2010) J. Med. Chem., 53, p. 2277
Joseph, P., Ouahrani-Bettache, S., Montero, J.L., Nishimori, I., Minakuchi, T., Vullo, D., Scozzafava, A., Supuran, C.T., (2011) Bioorg. Med. Chem., 19, p. 1172
Smith, K.S., Ferry, J.G., (2000) FEMS Microbiol. Rev., 24, p. 335
Del Prete, S., Vullo, D., Fisher, G.M., Andrews, K.T., Poulsen, S.A., Capasso, C., Supuran, C.T., (2014) Bioorg. Med. Chem. Lett., 24, p. 4389
Liu, F., Martin-Mingot, A., Lecornue, F., Jouannetaud, M.P., Maresca, A., Thibaudeau, S., Supuran, C.T., (2012) J. Enzyme Inhib. Med. Chem., 27, p. 886
Briganti, F., Pierattelli, R., Scozzafava, A., Supuran, C.T., (1996) Eur. J. Med. Chem., 31, p. 1001
Alterio, V., Di Fiore, A., D'Ambrosio, K., Supuran, C.T., De Simone, G., (2012) Chem. Rev., 112, p. 4421
Supuran, C.T., (2010) Bioorg. Med. Chem. Lett., 20, p. 3467
Masini, E., Carta, F., Scozzafava, A., Supuran, C.T., (2013) Expert Opin. Ther. Pat., 23, p. 705
Carta, F., Supuran, C.T., (2013) Expert Opin. Ther. Pat., 23, p. 681
Aggarwal, M., Kondeti, B., McKenna, R., (2013) Expert Opin. Ther. Pat., 23, p. 717
Aggarwal, M., Boone, C.D., Kondeti, B., McKenna, R., (2013) J. Enzyme Inhib. Med. Chem., 28, p. 267
Neri, D., Supuran, C.T., (2011) Nat. Rev. Drug Discov., 10, p. 767
Capasso, C., De Luca, V., Carginale, V., Cannio, R., Rossi, M., (2012) J. Enzyme Inhib. Med. Chem., 27, p. 892
Supuran, C.T., Clare, B.W., (1999) Eur. J. Med. Chem., 34, p. 41
Nasr, G., Petit, E., Supuran, C.T., Winum, J.Y., Barboiu, M., (2009) Bioorg. Med. Chem. Lett., 19, p. 6014
Supuran, C.T., Mincione, F., Scozzafava, A., Briganti, F., Mincione, G., Ilies, M.A., (1998) Eur. J. Med. Chem., 33, p. 247
Nasr, G., Cristian, A., Barboiu, M., Vullo, D., Winum, J.Y., Supuran, C.T., (2014) Bioorg. Med. Chem., 22, p. 2867
Pichake, J., Kharkar, P.S., Ceruso, M., Supuran, C.T., Toraskar, M.P., (2014) ACS Med. Chem. Lett., 5, p. 793
Scozzafava, A., Menabuoni, L., Mincione, F., Mincione, G., Supuran, C.T., (2001) Bioorg. Med. Chem. Lett., 11, p. 575
Supuran, C.T., Nicolae, A., Popescu, A., (1996) Eur. J. Med. Chem., 31, p. 431
Supuran, C.T., Popescu, A., Ilisiu, M., Costandache, A., Banciu, M.D., (1996) Eur. J. Med. Chem., 31, p. 439
Puccetti, L., Fasolis, G., Vullo, D., Chohan, Z.H., Scozzafava, A., Supuran, C.T., (2005) Bioorg. Med. Chem. Lett., 15, p. 3096
Luca, C., Barboiu, M., Supuran, C.T., (1991) Rev. Roum. Chim., 36, p. 1169
Supuran, C.T., Scozzafava, A., Popescu, A., Bobes-Tureac, R., Banciu, A., Creanga, A., Bobes-Tureac, G., Banciu, M.D., (1997) Eur. J. Med. Chem., 32, p. 445
Popescu, A., Simion, A., Scozzafava, A., Briganti, F., Supuran, C.T., (1999) J. Enzyme Inhib., 14, p. 407
Scozzafava, A., Banciu, M.D., Popescu, A., Supuran, C.T., (2000) J. Enzyme Inhib., 15, p. 533
Chohan, Z.H., Shad, H.A., Supuran, C.T., (2012) J. Enzyme Inhib. Med. Chem., 27, p. 58
Chohan, Z.H., Mahmood-Ul-Hassan, Khan, K.M., Supuran, C.T., (2005) J. Enzyme Inhib. Med. Chem., 20, p. 183
Mastrolorenzo, A., Rusconi, S., Scozzafava, A., Barbaro, G., Supuran, C.T., (2007) Curr. Med. Chem., 14, p. 2734
Schlicker, C., Hall, R.A., Vullo, D., Middelhaufe, S., Gertz, M., Supuran, C.T., Mühlschlegel, F.A., Steegborn, C.J., (2009) Mol. Biol., 385, p. 1207
Bahn, Y.S., Cox, G.M., Perfect, J.R., Heitman, J., (2013) Curr. Biol., 2005, p. 15
Syrjänen, L., Vermelho, A.B., Rodrigues Ide, A., Corte-Real, S., Salonen, T., Pan, P., Vullo, D., Supuran, C.T.J., (2013) Med Chem., 56, p. 7372
Zolfaghari Emameh, R., Barker, H., Tolvanen, M.E., Ortutay, C., Parkkila, S., (2014) Parasit. Vectors., 7, p. 38
Granger, D.L., Perfect, J.R., Durack, D.T., (1985) J. Clin. Invest., 76, p. 508
Klengel, T., Liang, W.J., Chaloupka, J., Ruoff, C., Schroppel, K., Naglik, J.R., (2005) Curr. Biol., 15, p. 2021
Lin, X., Heitman, J., (2006) Annu. Rev. Microbiol., 60, p. 69
Mogensen, E.G., Janbon, G., Chaloupka, J., Steegborn, C., Fu, M.S., Moyrand, F., (2006) Eukaryot. Cell, 5, p. 103
Nishimori, I., Onishi, S., Takeuchi, H., Supuran, C.T., (2008) Curr. Pharm. Des., 14, p. 622
Minakuchi, T., Nishimori, I., Vullo, D., Scozzafava, A., Supuran, C.T., (2009) J. Med. Chem., 52, p. 2226
Carta, F., Maresca, A., Suarez Covarrubias, A., Mowbray, S.L., Jones, T.A., Supuran, C.T., (2009) Bioorg. Med. Chem. Lett., 19, p. 6649
McCall, L.I., Zhang, W.W., Matlashewski, G., (2013) PLoS Pathol., 9, p. e1003053
Modakh, J.K., Liu, Y.C., Machuca, M.A., Supuran, C.T., Roujeinikova, A., (2015) PLoS One, 10, p. e0127149
Supuran, C.T., Casini, A., Scozzafava, A., (2004) Carbonic Anhydrase: Its Inhibitors and Activators, pp. 67-147. , C.T. Supuran, A. Scozzafava, J. Conway, CRC Press Boca Raton, FL
Abbate, F., Casini, A., Scozzafava, A., Supuran, C.T., (2003) J. Enzyme Inhib. Med. Chem., 18, p. 303
Alafeefy, A.M., Abdel-Aziz, H.A., Vullo, D., Al-Tamimi, A.M., Al-Jaber, N.A., Capasso, C., Supuran, C.T., (2014) Bioorg. Med. Chem., 22, p. 141
Singh, S., Supuran, C.T., (2014) J. Enzyme Inhib. Med. Chem., 29, p. 449
Biswas, S., Aggarwal, M., Güzel Ö., Scozzafava, A., McKenna, R., Supuran, C.T., (2011) Bioorg. Med. Chem., 19, p. 3732
Biswas, S., McKenna, R., Supuran, C.T., (2013) Bioorg. Med. Chem. Lett., 23, p. 5646
Sarikaya, B., Ceruso, M., Carta, F., Supuran, C.T., (2014) Bioorg. Med. Chem., 22, p. 5883
Khalifah, R.G., (1971) J. Biol. Chem., 246, p. 2561
Duda, D.M., Tu, C., Fisher, S.Z., An, H., Yoshioka, C., Govindasamy, L., Laipis, P.J., McKenna, R., (2005) Biochemistry, 44, p. 10046
Maresca, A., Carta, F., Vullo, D., Supuran, C.T., (2013) J. Enzyme Inhib. Med. Chem., 28, p. 407
Ekinci, D., Kurbanoglu, N.I., Salamci, E., Senturk, M., Supuran, C.T., (2012) J. Enzyme Inhib. Med. Chem., 27, p. 845
Ekinci, D., Karagoz, L., Ekinci, D., Senturk, M., Supuran, C.T., (2013) J. Enzyme Inhib. Med. Chem., 28, p. 283
Alp, C., Maresca, A., Alp, N.A., Gültekin, M.S., Ekinci, D., Scozzafava, A., Supuran, C.T., (2013) J. Enzyme Inhib. Med. Chem., 28, p. 294
Vullo, D., Innocenti, A., Nishimori, I., Pastorek, J., Scozzafava, A., Pastorekova, S., Supuran, C.T., (2005) Bioorg. Med. Chem. Lett., 15, p. 963
Vullo, D., Voipio, J., Innocenti, A., Rivera, C., Ranki, H., Scozzafava, A., Kaila, K., Supuran, C.T., (2005) Bioorg. Med. Chem. Lett., 15, p. 971
Bioorg Med Chem (ISSN: 0968-0896, 1464-3391, 0968-0896linking), 2015; 23(15): 4181-4187.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 2.923, 5-year impact factor: 2.869
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-84937521131&partnerID=40&md5=c7d21eb3e9b0a34eefa1986073fd0681
Keywords: Anti-Infective, Bacteria, Beta-Carbonic Anhydrase, Fungi, Pathogenic Microorganism, Protozoa, Schiff Base, Selective Inhibitor, Sulfonamide, 3 Fluorosulfanilamide, 4 (2 Aminoethyl) Benzenesulfonamide, Aldehyde, Bacterial Enzyme, Carbonate Dehydratase, Carbonate Dehydratase Inhibitor, Fungal Enzyme, Protozoal Protein, Unclassified Drug, Antibacterial Activity, Antifungal Activity, Antiprotozoal Activity, Article, Brucella Suis, Cryptococcus Neoformans, Drug Efficacy, Drug Potency, Drug Selectivity, Drug Structure, Drug Synthesis, Drug Targeting, Enzyme Inhibition, Hydrophilicity, Hydrophobicity, Leishmania Chagasi, Nonhuman, Bacteria (microorganisms), Brucella Melitensis Biovar Suis, Filobasidiella Neoformans, Leishmania Donovani Chagasi,
Affiliations:
*** IBB - CNR ***
Università Degli Studi di Firenze, Polo Scientifico, Laboratorio di Chimica Bioinorganica, Via della Lastruccia 3, Sesto Fiorentino (Florence), Italy
Department of Chemistry, College of Science, King Saud University, Riyadh, Saudi Arabia
Istituto di Biostrutture e Bioimmagini-CNR, Via Mezzocannone 16, Napoli, Italy
References:
Cardoso, T., Ribeiro, O., Aragao, I.C., Costa-Pereira, A., Sarmento, A.E., (2012) BMC Infect. Dis., 12, p. 37
Cox, G.M., Mukherjee, J., Cole, G.T., Casadeval, A., Perfect, J.R., (2000) Infect. Immun., 68, p. 443
Cox, G.M., McDade, H.C., Chen, S.C.A., Gottfredsson, M., Wright, L.C., Sorrell, T.C., Leidich, S.D., Perfect, J.R., (2001) Mol. Microbiol., 39, p. 166
Supuran, C.T., (2008) Nat. Rev. Drug Discov., 7, p. 168
Joseph, P., Turtaut, F., Ouahrani-Bettache, S., Montero, J.L., Nishimori, I., Minakuchi, T., Vullo, D., Cloning, (2010) J. Med. Chem., 53, p. 2277
Joseph, P., Ouahrani-Bettache, S., Montero, J.L., Nishimori, I., Minakuchi, T., Vullo, D., Scozzafava, A., Supuran, C.T., (2011) Bioorg. Med. Chem., 19, p. 1172
Smith, K.S., Ferry, J.G., (2000) FEMS Microbiol. Rev., 24, p. 335
Del Prete, S., Vullo, D., Fisher, G.M., Andrews, K.T., Poulsen, S.A., Capasso, C., Supuran, C.T., (2014) Bioorg. Med. Chem. Lett., 24, p. 4389
Liu, F., Martin-Mingot, A., Lecornue, F., Jouannetaud, M.P., Maresca, A., Thibaudeau, S., Supuran, C.T., (2012) J. Enzyme Inhib. Med. Chem., 27, p. 886
Briganti, F., Pierattelli, R., Scozzafava, A., Supuran, C.T., (1996) Eur. J. Med. Chem., 31, p. 1001
Alterio, V., Di Fiore, A., D'Ambrosio, K., Supuran, C.T., De Simone, G., (2012) Chem. Rev., 112, p. 4421
Supuran, C.T., (2010) Bioorg. Med. Chem. Lett., 20, p. 3467
Masini, E., Carta, F., Scozzafava, A., Supuran, C.T., (2013) Expert Opin. Ther. Pat., 23, p. 705
Carta, F., Supuran, C.T., (2013) Expert Opin. Ther. Pat., 23, p. 681
Aggarwal, M., Kondeti, B., McKenna, R., (2013) Expert Opin. Ther. Pat., 23, p. 717
Aggarwal, M., Boone, C.D., Kondeti, B., McKenna, R., (2013) J. Enzyme Inhib. Med. Chem., 28, p. 267
Neri, D., Supuran, C.T., (2011) Nat. Rev. Drug Discov., 10, p. 767
Capasso, C., De Luca, V., Carginale, V., Cannio, R., Rossi, M., (2012) J. Enzyme Inhib. Med. Chem., 27, p. 892
Supuran, C.T., Clare, B.W., (1999) Eur. J. Med. Chem., 34, p. 41
Nasr, G., Petit, E., Supuran, C.T., Winum, J.Y., Barboiu, M., (2009) Bioorg. Med. Chem. Lett., 19, p. 6014
Supuran, C.T., Mincione, F., Scozzafava, A., Briganti, F., Mincione, G., Ilies, M.A., (1998) Eur. J. Med. Chem., 33, p. 247
Nasr, G., Cristian, A., Barboiu, M., Vullo, D., Winum, J.Y., Supuran, C.T., (2014) Bioorg. Med. Chem., 22, p. 2867
Pichake, J., Kharkar, P.S., Ceruso, M., Supuran, C.T., Toraskar, M.P., (2014) ACS Med. Chem. Lett., 5, p. 793
Scozzafava, A., Menabuoni, L., Mincione, F., Mincione, G., Supuran, C.T., (2001) Bioorg. Med. Chem. Lett., 11, p. 575
Supuran, C.T., Nicolae, A., Popescu, A., (1996) Eur. J. Med. Chem., 31, p. 431
Supuran, C.T., Popescu, A., Ilisiu, M., Costandache, A., Banciu, M.D., (1996) Eur. J. Med. Chem., 31, p. 439
Puccetti, L., Fasolis, G., Vullo, D., Chohan, Z.H., Scozzafava, A., Supuran, C.T., (2005) Bioorg. Med. Chem. Lett., 15, p. 3096
Luca, C., Barboiu, M., Supuran, C.T., (1991) Rev. Roum. Chim., 36, p. 1169
Supuran, C.T., Scozzafava, A., Popescu, A., Bobes-Tureac, R., Banciu, A., Creanga, A., Bobes-Tureac, G., Banciu, M.D., (1997) Eur. J. Med. Chem., 32, p. 445
Popescu, A., Simion, A., Scozzafava, A., Briganti, F., Supuran, C.T., (1999) J. Enzyme Inhib., 14, p. 407
Scozzafava, A., Banciu, M.D., Popescu, A., Supuran, C.T., (2000) J. Enzyme Inhib., 15, p. 533
Chohan, Z.H., Shad, H.A., Supuran, C.T., (2012) J. Enzyme Inhib. Med. Chem., 27, p. 58
Chohan, Z.H., Mahmood-Ul-Hassan, Khan, K.M., Supuran, C.T., (2005) J. Enzyme Inhib. Med. Chem., 20, p. 183
Mastrolorenzo, A., Rusconi, S., Scozzafava, A., Barbaro, G., Supuran, C.T., (2007) Curr. Med. Chem., 14, p. 2734
Schlicker, C., Hall, R.A., Vullo, D., Middelhaufe, S., Gertz, M., Supuran, C.T., Mühlschlegel, F.A., Steegborn, C.J., (2009) Mol. Biol., 385, p. 1207
Bahn, Y.S., Cox, G.M., Perfect, J.R., Heitman, J., (2013) Curr. Biol., 2005, p. 15
Syrjänen, L., Vermelho, A.B., Rodrigues Ide, A., Corte-Real, S., Salonen, T., Pan, P., Vullo, D., Supuran, C.T.J., (2013) Med Chem., 56, p. 7372
Zolfaghari Emameh, R., Barker, H., Tolvanen, M.E., Ortutay, C., Parkkila, S., (2014) Parasit. Vectors., 7, p. 38
Granger, D.L., Perfect, J.R., Durack, D.T., (1985) J. Clin. Invest., 76, p. 508
Klengel, T., Liang, W.J., Chaloupka, J., Ruoff, C., Schroppel, K., Naglik, J.R., (2005) Curr. Biol., 15, p. 2021
Lin, X., Heitman, J., (2006) Annu. Rev. Microbiol., 60, p. 69
Mogensen, E.G., Janbon, G., Chaloupka, J., Steegborn, C., Fu, M.S., Moyrand, F., (2006) Eukaryot. Cell, 5, p. 103
Nishimori, I., Onishi, S., Takeuchi, H., Supuran, C.T., (2008) Curr. Pharm. Des., 14, p. 622
Minakuchi, T., Nishimori, I., Vullo, D., Scozzafava, A., Supuran, C.T., (2009) J. Med. Chem., 52, p. 2226
Carta, F., Maresca, A., Suarez Covarrubias, A., Mowbray, S.L., Jones, T.A., Supuran, C.T., (2009) Bioorg. Med. Chem. Lett., 19, p. 6649
McCall, L.I., Zhang, W.W., Matlashewski, G., (2013) PLoS Pathol., 9, p. e1003053
Modakh, J.K., Liu, Y.C., Machuca, M.A., Supuran, C.T., Roujeinikova, A., (2015) PLoS One, 10, p. e0127149
Supuran, C.T., Casini, A., Scozzafava, A., (2004) Carbonic Anhydrase: Its Inhibitors and Activators, pp. 67-147. , C.T. Supuran, A. Scozzafava, J. Conway, CRC Press Boca Raton, FL
Abbate, F., Casini, A., Scozzafava, A., Supuran, C.T., (2003) J. Enzyme Inhib. Med. Chem., 18, p. 303
Alafeefy, A.M., Abdel-Aziz, H.A., Vullo, D., Al-Tamimi, A.M., Al-Jaber, N.A., Capasso, C., Supuran, C.T., (2014) Bioorg. Med. Chem., 22, p. 141
Singh, S., Supuran, C.T., (2014) J. Enzyme Inhib. Med. Chem., 29, p. 449
Biswas, S., Aggarwal, M., Güzel Ö., Scozzafava, A., McKenna, R., Supuran, C.T., (2011) Bioorg. Med. Chem., 19, p. 3732
Biswas, S., McKenna, R., Supuran, C.T., (2013) Bioorg. Med. Chem. Lett., 23, p. 5646
Sarikaya, B., Ceruso, M., Carta, F., Supuran, C.T., (2014) Bioorg. Med. Chem., 22, p. 5883
Khalifah, R.G., (1971) J. Biol. Chem., 246, p. 2561
Duda, D.M., Tu, C., Fisher, S.Z., An, H., Yoshioka, C., Govindasamy, L., Laipis, P.J., McKenna, R., (2005) Biochemistry, 44, p. 10046
Maresca, A., Carta, F., Vullo, D., Supuran, C.T., (2013) J. Enzyme Inhib. Med. Chem., 28, p. 407
Ekinci, D., Kurbanoglu, N.I., Salamci, E., Senturk, M., Supuran, C.T., (2012) J. Enzyme Inhib. Med. Chem., 27, p. 845
Ekinci, D., Karagoz, L., Ekinci, D., Senturk, M., Supuran, C.T., (2013) J. Enzyme Inhib. Med. Chem., 28, p. 283
Alp, C., Maresca, A., Alp, N.A., Gültekin, M.S., Ekinci, D., Scozzafava, A., Supuran, C.T., (2013) J. Enzyme Inhib. Med. Chem., 28, p. 294
Vullo, D., Innocenti, A., Nishimori, I., Pastorek, J., Scozzafava, A., Pastorekova, S., Supuran, C.T., (2005) Bioorg. Med. Chem. Lett., 15, p. 963
Vullo, D., Voipio, J., Innocenti, A., Rivera, C., Ranki, H., Scozzafava, A., Kaila, K., Supuran, C.T., (2005) Bioorg. Med. Chem. Lett., 15, p. 971
Inhibition studies of bacterial, fungal and protozoan β-class carbonic anhydrases with Schiff bases incorporating sulfonamide moieties
A series of new Schiff bases derived from sulfanilamide, 3-fluorosulfanilamide or 4-(2-aminoethyl)-benzenesulfonamide containing either a hydrophobic or a hydrophilic tail, have been investigated as inhibitors of three β-carbonic anhydrases (CA, EC 4.2.1.1) from three different microorganisms. Their antifungal, antibacterial and antiprotozoan activities have been determined against the pathogenic fungus Cryptococcus neoformans, the bacterial pathogen Brucella suis and the protozoan parasite Leishmania donovani chagasi, responsible for Leishmaniasis. The results of these inhibition studies show that all three enzymes were efficiently inhibited by the Schiff base sulfonamides with KI values in the nanomolar or submicromolar range, depending on the nature of the tail, coming from the aryl/heteroaryl moiety present in the starting aldehyde employed in the synthesis. Furthermore, the compounds hereby investigated revealed high β-CAs selectivity over the ubiquitous, physiologically relevant and off-target human isoforms (CA I and II) and to be more potent as antifungal and antibacterial than as antiprotozoan potential drugs. © 2015 Elsevier Ltd. All rights reserved.
A series of new Schiff bases derived from sulfanilamide, 3-fluorosulfanilamide or 4-(2-aminoethyl)-benzenesulfonamide containing either a hydrophobic or a hydrophilic tail, have been investigated as inhibitors of three β-carbonic anhydrases (CA, EC 4.2.1.1) from three different microorganisms. Their antifungal, antibacterial and antiprotozoan activities have been determined against the pathogenic fungus Cryptococcus neoformans, the bacterial pathogen Brucella suis and the protozoan parasite Leishmania donovani chagasi, responsible for Leishmaniasis. The results of these inhibition studies show that all three enzymes were efficiently inhibited by the Schiff base sulfonamides with K
Inhibition studies of bacterial, fungal and protozoan β-class carbonic anhydrases with Schiff bases incorporating sulfonamide moieties
| ▼ Targeting Of Protein-Protein Interactions For Therapeutic Purposes |
Inhibition studies of bacterial, fungal and protozoan β-class carbonic anhydrases with Schiff bases incorporating sulfonamide moieties
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Nocentini A, Alterio V, Bua S, Micheli L, Esposito D, Buonanno M, Bartolucci G, Osman SM, Alothman ZA, Cirilli R, Pierini M, Monti SM, Di Cesare Mannelli L, Gratteri P, Ghelardini C, De Simone G, Supuran CT
* Phenyl(thio)phosphon(amid)ate Benzenesulfonamides as Potent and Selective Inhibitors of Human Carbonic Anhydrases II and VII Counteract Allodynia in a Mouse Model of Oxaliplatin-Induced Neuropathy (112 views)
J Med Chem (ISSN: 0022-2623linking, 0022-2623print), 2020 May 28; 63(10): 5185-5200.
Impact Factor: 6.205
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Bocian A, Szymańska M, Brykczyńska D, Kubicki M, Wałęsa-chorab M, Roviello GN, Fik-jaskółka MA, Gorczyński A, Patroniak V
* New artificial biomimetic enzyme analogues based on iron(II/III) Schiff Base complexes: an effect of (benz)imidazole organic moieties on phenoxazinone synthase and DNA recognition (225 views)
Molecules (ISSN: 1420-3049linking, 1420-3049electronic), 2019 Aug 31; 24(17): 3173-3173.
Impact Factor: 3.06
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Alterio V, Esposito D, Monti SM, Supuran CT, De Simone G
* Crystal structure of the human carbonic anhydrase II adduct with 1-(4-sulfamoylphenyl-ethyl)-2, 4, 6-triphenylpyridinium perchlorate, a membrane-impermeant, isoform selective inhibitor (533 views)
J Enzym Inhib Med Ch (ISSN: 1475-6374electronic, 1475-6366linking), 2018 Dec; 33(1): 151-157.
Impact Factor: 4.293
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Monti SM, Meccariello A, Ceruso M, Szafranski K, Slawinski J, Supuran CT
* Inhibition studies of Brucella suis beta-carbonic anhydrases with a series of 4-substituted pyridine-3-sulphonamides (369 views)
J Enzym Inhib Med Ch (ISSN: 1475-6374electronic, 1475-6366linking), 2018 Dec; 33(1): 255-259.
Impact Factor: 2.332
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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 (256 views)
Bioorg Med Chem (ISSN: 0968-0896, 1464-3391, 0968-0896linking), 2017; 25(2): 539-544.
Impact Factor: 2.881
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Calce E, Mignogna E, Bugatti V, Galdiero M, Vittoria V, De Luca S
* Pectin functionalized with natural fatty acids as antimicrobial agent (391 views)
Int J Biol Macromol (ISSN: 0141-8130, 0141-8130linking, 1879-0003electronic), 2014 Jul; 68: 28-32.
Impact Factor: 2.858
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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 (431 views)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 2014; 101(7): 769-778.
Impact Factor: 2.385
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Avitabile C, Capparelli R, Rigano MM, Fulgione A, Barone A, Pedone C, Romanelli A
* Antimicrobial peptides from plants: Stabilization of the γ core of a tomato defensin by intramolecular disulfide bond (865 views)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2013 Apr; 19(4): 240-245.
Impact Factor: 1.862
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Scudiero O, Galdiero S, Nigro E, Del Vecchio L, Di Noto R, Cantisani M, Colavita I, Galdiero M, Cassiman JJ, Daniele A, Pedone C, Salvatore F
* Chimeric beta-defensin analogs, including the novel 3NI analog, display salt-resistant antimicrobial activity and lack toxicity in human epithelial cell lines (554 views)
Antimicrob Agents Ch (ISSN: 1098-6596, 0066-4804), 2013 Apr; 57(4): 1701-1708.
Impact Factor: 4.451
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Monti SM, De Simone G, Dathan NA, Ludwig M, Vullo D, Scozzafava A, Capasso C, Supuran CT
* Kinetic And Anion Inhibition Studies Of A Beta-Carbonic Anhydrase (fbica 1) From The C-4 Plant Flaveria Bidentis (442 views)
Bioorg Med Chem Lett (ISSN: 0960-894x), 2013 Mar 15; 23(6): 1626-1630.
Impact Factor: 2.331
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Berisio R
* Learning from pathogens: Exploiting host-pathogen liaison for therapeutic development (554 views)
Curr Protein Pept Sci (ISSN: 1389-2037, 1389-2037linking), 2012 Dec; 13(8): 697-698.
Impact Factor: 2.326
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Romanelli A, Moggio L, Montella RC, Campiglia P, Iannaccone M, Capuano F, Pedone C, Capparelli R
* Peptides from Royal Jelly: studies on the antimicrobial activity of jelleins, jelleins analogs and synergy with temporins (1516 views)
J Pept Sci (ISSN: 1099-1387, 1075-2617, 1075-2617print), 2011 Dec 2; 17(5): 348-352.
Impact Factor: 1.799
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Scudiero O, Galdiero S, Cantisani M, Di Noto R, Vitiello M, Galdiero M, Naclerio G, Cassiman JJ, Pedone C, Castaldo G, Salvatore F
* Novel synthetic, salt-resistant analogs of human beta-defensins 1 and 3 endowed with enhanced antimicrobial activity (643 views)
Antimicrob Agents Ch (ISSN: 1098-6596, 0066-4804), 2010 Jun; 54(6): 2312-2322.
Impact Factor: 4.672
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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 (480 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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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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* New N4-Donor Ligands as Supramolecular Guests for DNA and RNA: Synthesis, Structural Characterization, In Silico, Spectrophotometric and Antimicrobial Studies (23 views)
Molecules (ISSN: 1420-3049linking), 2023 Jan; 28: 400-421.
Impact Factor: 4.927
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Urbański LJ, Di Fiore A, Azizi L, Hytönen VP, Kuuslahti M, Buonanno M, Monti SM, Angeli A, Zolfaghari Emameh R, Supuran CT, De Simone G, Parkkila S
* Biochemical and structural characterisation of a protozoan beta-carbonic anhydrase from Trichomonas vaginalis (130 views)
J Enzym Inhib Med Ch (ISSN: 1475-6366linking, 1475-6374electronic), 2020 Dec; 35(1): 1292-1299.
Impact Factor: 4.673
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Nocentini A, Alterio V, Bua S, Micheli L, Esposito D, Buonanno M, Bartolucci G, Osman SM, Alothman ZA, Cirilli R, Pierini M, Monti SM, Di Cesare Mannelli L, Gratteri P, Ghelardini C, De Simone G, Supuran CT
* Phenyl(thio)phosphon(amid)ate Benzenesulfonamides as Potent and Selective Inhibitors of Human Carbonic Anhydrases II and VII Counteract Allodynia in a Mouse Model of Oxaliplatin-Induced Neuropathy (112 views)
J Med Chem (ISSN: 0022-2623linking, 0022-2623print), 2020 May 28; 63(10): 5185-5200.
Impact Factor: 6.205
View Export to BibTeX Export to EndNote
Bocian A, Szymańska M, Brykczyńska D, Kubicki M, Wałęsa-chorab M, Roviello GN, Fik-jaskółka MA, Gorczyński A, Patroniak V
* New artificial biomimetic enzyme analogues based on iron(II/III) Schiff Base complexes: an effect of (benz)imidazole organic moieties on phenoxazinone synthase and DNA recognition (225 views)
Molecules (ISSN: 1420-3049linking, 1420-3049electronic), 2019 Aug 31; 24(17): 3173-3173.
Impact Factor: 3.06
View Export to BibTeX Export to EndNote
Alterio V, Esposito D, Monti SM, Supuran CT, De Simone G
* Crystal structure of the human carbonic anhydrase II adduct with 1-(4-sulfamoylphenyl-ethyl)-2, 4, 6-triphenylpyridinium perchlorate, a membrane-impermeant, isoform selective inhibitor (533 views)
J Enzym Inhib Med Ch (ISSN: 1475-6374electronic, 1475-6366linking), 2018 Dec; 33(1): 151-157.
Impact Factor: 4.293
View Export to BibTeX Export to EndNote
Monti SM, Meccariello A, Ceruso M, Szafranski K, Slawinski J, Supuran CT
* Inhibition studies of Brucella suis beta-carbonic anhydrases with a series of 4-substituted pyridine-3-sulphonamides (369 views)
J Enzym Inhib Med Ch (ISSN: 1475-6374electronic, 1475-6366linking), 2018 Dec; 33(1): 255-259.
Impact Factor: 2.332
View Export to BibTeX Export to EndNote
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 (256 views)
Bioorg Med Chem (ISSN: 0968-0896, 1464-3391, 0968-0896linking), 2017; 25(2): 539-544.
Impact Factor: 2.881
View Export to BibTeX Export to EndNote
Calce E, Mignogna E, Bugatti V, Galdiero M, Vittoria V, De Luca S
* Pectin functionalized with natural fatty acids as antimicrobial agent (391 views)
Int J Biol Macromol (ISSN: 0141-8130, 0141-8130linking, 1879-0003electronic), 2014 Jul; 68: 28-32.
Impact Factor: 2.858
View Export to BibTeX Export to EndNote
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 (431 views)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 2014; 101(7): 769-778.
Impact Factor: 2.385
View Export to BibTeX Export to EndNote
Avitabile C, Capparelli R, Rigano MM, Fulgione A, Barone A, Pedone C, Romanelli A
* Antimicrobial peptides from plants: Stabilization of the γ core of a tomato defensin by intramolecular disulfide bond (865 views)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2013 Apr; 19(4): 240-245.
Impact Factor: 1.862
View Export to BibTeX Export to EndNote
Scudiero O, Galdiero S, Nigro E, Del Vecchio L, Di Noto R, Cantisani M, Colavita I, Galdiero M, Cassiman JJ, Daniele A, Pedone C, Salvatore F
* Chimeric beta-defensin analogs, including the novel 3NI analog, display salt-resistant antimicrobial activity and lack toxicity in human epithelial cell lines (554 views)
Antimicrob Agents Ch (ISSN: 1098-6596, 0066-4804), 2013 Apr; 57(4): 1701-1708.
Impact Factor: 4.451
View Export to BibTeX Export to EndNote
Monti SM, De Simone G, Dathan NA, Ludwig M, Vullo D, Scozzafava A, Capasso C, Supuran CT
* Kinetic And Anion Inhibition Studies Of A Beta-Carbonic Anhydrase (fbica 1) From The C-4 Plant Flaveria Bidentis (442 views)
Bioorg Med Chem Lett (ISSN: 0960-894x), 2013 Mar 15; 23(6): 1626-1630.
Impact Factor: 2.331
View Export to BibTeX Export to EndNote
Berisio R
* Learning from pathogens: Exploiting host-pathogen liaison for therapeutic development (554 views)
Curr Protein Pept Sci (ISSN: 1389-2037, 1389-2037linking), 2012 Dec; 13(8): 697-698.
Impact Factor: 2.326
View Export to BibTeX Export to EndNote
Romanelli A, Moggio L, Montella RC, Campiglia P, Iannaccone M, Capuano F, Pedone C, Capparelli R
* Peptides from Royal Jelly: studies on the antimicrobial activity of jelleins, jelleins analogs and synergy with temporins (1516 views)
J Pept Sci (ISSN: 1099-1387, 1075-2617, 1075-2617print), 2011 Dec 2; 17(5): 348-352.
Impact Factor: 1.799
View Export to BibTeX Export to EndNote
Scudiero O, Galdiero S, Cantisani M, Di Noto R, Vitiello M, Galdiero M, Naclerio G, Cassiman JJ, Pedone C, Castaldo G, Salvatore F
* Novel synthetic, salt-resistant analogs of human beta-defensins 1 and 3 endowed with enhanced antimicrobial activity (643 views)
Antimicrob Agents Ch (ISSN: 1098-6596, 0066-4804), 2010 Jun; 54(6): 2312-2322.
Impact Factor: 4.672
View Export to BibTeX Export to EndNote
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 (480 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2009 Oct 8; 52(19): 5990-5998.
Impact Factor: 4.802
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
17 Records (17 excluding Abstracts).
Total impact factor: 58.395 (58.395 excluding Abstracts).
Total 5 year impact factor: 53.273 (53.273 excluding Abstracts).
Total impact factor: 58.395 (58.395 excluding Abstracts).
Total 5 year impact factor: 53.273 (53.273 excluding Abstracts).
367 views. Last view on Monday 06 March 2023, 21:14:06
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