Hypoxia-targeting carbonic anhydrase IX inhibitors by a new series of nitroimidazole-sulfonamides/sulfamides/sulfamates (548 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2013 Nov 14; 56(21): 8512-8520.
Export to BibTeX Export to EndNote
Paper type: Journal Article, Research Support, Non-U. S. Gov'T,
Impact factor: 5.48, 5-year impact factor: 5.504
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-84887954229&partnerID=40&md5=7d5350af89014222004a1a3b5a8f354f
Keywords: (2 Nitro Imidazol 1 Yl) Acetic Acid, 2 (2 Nitro Imidazol 1 Yl) N (3 Sulfamoylphenyl)acetamide, 2 (2 Nitro Imidazol 1 Yl) N (4 Sulfamoylbenzyl)acetamide, 2 (2 Nitro Imidazol 1 Yl) N (4 Sulfamoylphenyl)acetamide, 2 (2 Nitro Imidazol 1 Yl) N [2 (4 Sulfamoylphenyl)ethyl]acetamide, 2 (2 Nitro Imidazol 1 Yl)ethylamine, Antineoplastic Agent, Carbonate Dehydratase Inhibitor, Carbonate Dehydratase Xii, Doxorubicin, N (3 Sulfamoylphenyl) N [(2 Aminoethyl) 2 Methyl 5 Nitroimidazolyl] Thiourea, N (4 Sulfamoylbenzyl) N [(2 Aminoethyl) 2 Methyl 5 Nitroimidazolyl] Thiourea, N (4 Sulfamoylphenyl) N [(2 Aminoethyl) 2 Methyl 5 Nitroimidazolyl] Thiourea, N (4 Sulfamoylphenylethyl) N [(2 Aminoethyl) 2 Methyl 5 Nitroimidazolyl] Thiourea, N [2 (2 Methyl 5 Nitro Imidazol 1 Yl)ethyl]sulfamide, N [2 (2 Methyl Imidazol 1 Yl)propyl]sulfamide, N [2 (2 Nitro Imidazol 1 Yl)ethyl]sulfamide, N Methanesulfonyl 1 (2 Aminoethyl) 2 Methyl 5 Nitroimidazole, N Methanesulfonyl 2 (2 Nitro Imidazol 1 Yl)ethylamine, N[2 (2 Methyl 5 Nitro Imidazol 1 Yl)ethyl]sulfamate, Nitroimidazole Derivative, Sulfamide Derivative, Sulfonamide, Tert Butyl (2 Nitro Imidazol 1 Yl) Acetate, Unclassified Drug, Acidosis, Animal Cell, Animal Experiment, Animal Model, Article, Chemosensitization, Controlled Study, Enzyme Active Site, Enzyme Activity, Hela Cell, Human, Human Cell, Hypoxia, In Vitro Study, In Vivo Study, Mouse, Nonhuman, Protein Expression, X Ray Crystallography, Anoxia, Antigens, Carbonic Anhydrases, Dose-Response Relationship, Enzyme Inhibitors, Ht29 Cells, Molecular, Molecular Structure, Structure-Activity Relationship, Sulfonic Acids, Amides Chemistry, Neoplasm Metabolism, Carbonic Anhydrases Metabolism, Enzyme Inhibitors Chemical Synthesis Chemistry Pharmacology, Nitroimidazoles Chemistry, Sulfonamides Chemistry, Sulfonic Acids Chemistry, 2 (2 Nitro Imidazol 1 Yl) N (3 Sulfamoylphenyl) Acetamide, 2 (2 Nitro Imidazol 1 Yl) N (4 Sulfamoylbenzyl) Acetamide, 2 (2 Nitro Imidazol 1 Yl) N (4 Sulfamoylphenyl) Acetamide, 2 (2 Nitro Imidazol 1 Yl) N [2 (4 Sulfamoylphenyl) Ethyl] Acetamide, 2 (2 Nitro Imidazol 1 Yl) Ethylamine, N [2 (2 Methyl 5 Nitro Imidazol 1 Yl) Ethyl] Sulfamide, N [2 (2 Methyl Imidazol 1 Yl) Propyl] Sulfamide, N [2 (2 Nitro Imidazol 1 Yl) Ethyl] Sulfamide, N Methanesulfonyl 2 (2 Nitro Imidazol 1 Yl) Ethylamine, N [2 (2 Methyl 5 Nitro Imidazol 1 Yl) Ethyl] Sulfamate,
Affiliations:
*** IBB - CNR ***
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS-UM1-UM2 Baîtiment de Recherche Max Mousseron, Ecole Nationale Supérieure de Chimie de Montpellier, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex, France
Department of Radiation Oncology (MAASTRO Lab), GROW - School for Oncology and Developmental Biology, Maastricht University Medical Centre, Universiteitssingel 50/23, 6200 MD, Maastricht, Netherlands
Istituto di Biostrutture e Bioimmagini - CNR, via Mezzocannone 16, 80134 Naples, Italy
Neurofarba Department, Section of Pharmaceutical Sciences, Università Degli Studi di Firenze, Via Ugo Schiff 6, 50019 Sesto Fiorentino (Florence), Italy
References:
Wilson, W.R., Hay, M.P., Targeting hypoxia in cancer therapy (2011) Nature Rev. Cancer, 11, pp. 393-41
Bennewith, K.L., Dedhar, S., Targeting hypoxic tumour cells to overcome metastasis (2011) BMC Cancer, 11, p. 504
Supuran, C.T., Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators (2008) Nature Rev. Drug Discovery, 7, pp. 168-181
McDonald, P.C., Winum, J.-Y., Supuran, C.T., Dedhar, S., Recent developments in targeting carbonic anhydrase IX for cancer therapeutics (2012) Oncotarget, 3, pp. 84-97
Neri, D., Supuran, C.T., Interfering with pH regulation in tumours as a therapeutic strategy (2011) Nature Rev. Drug Discovery, 10, pp. 767-777
Pacchiano, F., Carta, F., McDonald, P.C., Lou, Y., Vullo, D., Scozzafava, A., Dedhar, S., Supuran, C.T., Ureido-substituted benzenesulfonamides potently inhibit carbonic anhydrase IX and show antimetastatic activity in a model of breast cancer metastasis (2011) J. Med. Chem., 54, pp. 1896-1902
Touisni, N., Maresca, A., McDonald, P.C., Lou, Y., Scozzafava, A., Dedhar, S., Winum, J.-Y., Supuran, C.T., Glycosyl coumarin carbonic anhydrase IX and XII inhibitors strongly attenuate the growth of primary breast tumors (2011) J. Med. Chem., 54, pp. 8271-8277
Lou, Y., McDonald, P.C., Oloumi, A., Chia, S., Ostlund, C., Ahmadi, A., Kyle, A., Dedhar, S., Targeting tumor hypoxia: Suppression of breast tumor growth and metastasis by novel carbonic anhydrase IX inhibitors (2011) Cancer Res., 71, pp. 3364-3376
Dubois, L., Peeters, S., Lieuwes, N.G., Geusens, N., Thiry, A., Wigfield, S., Carta, F., Lambin, P., Specific inhibition of carbonic anhydrase IX activity enhances the in vivo therapeutic effect of tumor irradiation (2011) Radiother. Oncol., 99, pp. 424-431
Gieling, R.G., Babur, M., Mamnani, L., Burrows, N., Telfer, B.A., Carta, F., Winum, J.-Y., Williams, K.J., Antimetastatic effect of sulfamate carbonic anhydrase IX inhibitors in breast carcinoma xenografts (2012) J. Med. Chem., 55, pp. 5591-5600
Liu, K., Zhu, H.L., Nitroimidazoles as anti-tumor agents (2011) Anti-Cancer Agents Med. Chem., 11, pp. 687-691
Overgaard, J., Overgaard, M., Nielsen, O.S., Pedersen, A.K., Timothy, A.R., A comparative investigation of nimorazole and misonidazole as hypoxic radiosensitizers in a C3H mammary carcinoma in vivo (1982) Br. J. Cancer, 46, pp. 904-911
D'Ambrosio, K., Vitale, R.M., Dogné, J.M., Masereel, B., Innocenti, A., Scozzafava, A., De Simone, G., Supuran, C.T., Carbonic anhydrase inhibitors: Bioreductive nitro-containing sulfonamides with selectivity for targeting the tumor associated isoforms IX and XII (2008) J. Med. Chem., 51, pp. 3230-3237
Rami, M., Cecchi, A., Montero, J.-L., Innocenti, A., Vullo, D., Scozzafava, A., Winum, J.-Y., Supuran, C.T., Carbonic anhydrase inhibitors: Design of membrane-impermeant copper(II) complexes of DTPA-, DOTA-, and TETA-tailed sulfonamides targeting the tumor-associated transmembrane isoform IX (2008) ChemMedChem, 3, pp. 1780-1788
Rami, M., Montero, J.-L., Dubois, L., Lambin, P., Scozzafava, A., Winum, J.-Y., Supuran, C.T., Carbonic anhydrase inhibitors: Gd(III) complexes of DOTA- and TETA-sulfonamide conjugates targeting the tumor associated carbonic anhydrase isozymes IX and XII (2010) New J. Chem., 34, pp. 2139-2144
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
Winum, J.-Y., Carta, F., Ward, C., Mullen, P., Harrison, D., Langdon, S.P., Cecchi, A., Supuran, C.T., Ureido-substituted sulfamates show potent carbonic anhydrase IX inhibitory and antiproliferative activities against breast cancer cell lines (2012) Bioorg. Med. Chem. Lett., 22, pp. 4681-4685
Hoigebazar, L., Jeong, J.M., Choi, S.Y., Choi, J.Y., Shetty, D., Lee, Y.S., Lee, D.S., Chung, Y.K., Synthesis and characterization of nitroimidazole derivatives for 68Ga-labeling and testing in tumor xenografted mice (2010) J. Med. Chem., 53, pp. 6378-6385
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
Dubois, L., Douma, K., Supuran, C.T., Chiu, R.K., Van Zandvoort, M.A., Pastoreková, S., Scozzafava, A., Lambin, P., Imaging the hypoxia surrogate marker CA IX requires expression and catalytic activity for binding fluorescent sulfonamide inhibitors (2007) Radiother. Oncol., 83, pp. 367-373
Eriksson, A.E., Jones, T.A., Liljas, A., Refined structure of human carbonic anhydrase II at 2.0 Å resolution (1988) Proteins, 4, pp. 274-282
Winum, J.-Y., Temperini, C., El Cheikh, K., Innocenti, A., Vullo, D., Ciattini, S., Montero, J.L., Supuran, C.T., Carbonic anhydrase inhibitors: Clash with Ala65 as a means for designing inhibitors with low affinity for the ubiquitous isozyme II, exemplified by the crystal structure of the topiramate sulfamide analogue (2006) J. Med. Chem., 49, pp. 7024-7031
Di Fiore, A., Monti, S.M., Innocenti, A., Winum, J.Y., De Simone, G., Supuran, C.T., Carbonic anhydrase inhibitors: Crystallographic and solution binding studies for the interaction of a boron-containing aromatic sulfamide with mammalian isoforms I-XV (2010) Bioorg. Med. Chem. Lett., 20, pp. 3601-3605
De Simone, G., Alterio, V., Supuran, C.T., Exploiting the hydrophobic and hydrophilic binding sites for designing carbonic anhydrase inhibitors (2013) Expert Opin. Drug Discovery, 8, pp. 793-810
Otwinowski, Z., Minor, W., Processing of X-ray diffraction data collected in oscillation mode (1997) Methods Enzymol., 276, pp. 307-326
Brünger, A.T., Adams, P.D., Clore, G.M., Delano, W.L., Gros, P., Grosse-Kunstleve, R.W., Jiang, J.S., Warren, G.L., (1998) Acta Crystallogr., Sect. D: Biol. Crystallogr., 54, pp. 905-921
Jones, T.A., Zou, J.Y., Cowan, S.W., Kjeldgaard, M., (1991) Acta Crystallogr. Sect. A: Found. Crystallogr., 47, pp. 110-119
Allen, F.H., The Cambridge Structural Database: A quarter of a million crystal structures and rising (2002) Acta Crystallogr., Sect. B: Struct. Sci., 58, pp. 380-388
Wilson, W. R., Hay, M. P., Targeting hypoxia in cancer therapy (2011) Nature Rev. Cancer, 11, pp. 393-41
Bennewith, K. L., Dedhar, S., Targeting hypoxic tumour cells to overcome metastasis (2011) BMC Cancer, 11, p. 504
Supuran, C. T., Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators (2008) Nature Rev. Drug Discovery, 7, pp. 168-181
McDonald, P. C., Winum, J. -Y., Supuran, C. T., Dedhar, S., Recent developments in targeting carbonic anhydrase IX for cancer therapeutics (2012) Oncotarget, 3, pp. 84-97
Gieling, R. G., Babur, M., Mamnani, L., Burrows, N., Telfer, B. A., Carta, F., Winum, J. -Y., Williams, K. J., Antimetastatic effect of sulfamate carbonic anhydrase IX inhibitors in breast carcinoma xenografts (2012) J. Med. Chem., 55, pp. 5591-5600
Liu, K., Zhu, H. L., Nitroimidazoles as anti-tumor agents (2011) Anti-Cancer Agents Med. Chem., 11, pp. 687-691
Winum, J. -Y., Carta, F., Ward, C., Mullen, P., Harrison, D., Langdon, S. P., Cecchi, A., Supuran, C. T., Ureido-substituted sulfamates show potent carbonic anhydrase IX inhibitory and antiproliferative activities against breast cancer cell lines (2012) Bioorg. Med. Chem. Lett., 22, pp. 4681-4685
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, 4, pp. 274-282
Winum, J. -Y., Temperini, C., El Cheikh, K., Innocenti, A., Vullo, D., Ciattini, S., Montero, J. L., Supuran, C. T., Carbonic anhydrase inhibitors: Clash with Ala65 as a means for designing inhibitors with low affinity for the ubiquitous isozyme II, exemplified by the crystal structure of the topiramate sulfamide analogue (2006) J. Med. Chem., 49, pp. 7024-7031
Br nger, A. T., Adams, P. D., Clore, G. M., Delano, W. L., Gros, P., Grosse-Kunstleve, R. W., Jiang, J. S., Warren, G. L., (1998) Acta Crystallogr., Sect. D: Biol. Crystallogr., 54, pp. 905-921
Jones, T. A., Zou, J. Y., Cowan, S. W., Kjeldgaard, M., (1991) Acta Crystallogr. Sect. A: Found. Crystallogr., 47, pp. 110-119
Allen, F. H., The Cambridge Structural Database: A quarter of a million crystal structures and rising (2002) Acta Crystallogr., Sect. B: Struct. Sci., 58, pp. 380-388
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2013 Nov 14; 56(21): 8512-8520.
Export to BibTeX Export to EndNote
Paper type: Journal Article, Research Support, Non-U. S. Gov'T,
Impact factor: 5.48, 5-year impact factor: 5.504
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-84887954229&partnerID=40&md5=7d5350af89014222004a1a3b5a8f354f
Keywords: (2 Nitro Imidazol 1 Yl) Acetic Acid, 2 (2 Nitro Imidazol 1 Yl) N (3 Sulfamoylphenyl)acetamide, 2 (2 Nitro Imidazol 1 Yl) N (4 Sulfamoylbenzyl)acetamide, 2 (2 Nitro Imidazol 1 Yl) N (4 Sulfamoylphenyl)acetamide, 2 (2 Nitro Imidazol 1 Yl) N [2 (4 Sulfamoylphenyl)ethyl]acetamide, 2 (2 Nitro Imidazol 1 Yl)ethylamine, Antineoplastic Agent, Carbonate Dehydratase Inhibitor, Carbonate Dehydratase Xii, Doxorubicin, N (3 Sulfamoylphenyl) N [(2 Aminoethyl) 2 Methyl 5 Nitroimidazolyl] Thiourea, N (4 Sulfamoylbenzyl) N [(2 Aminoethyl) 2 Methyl 5 Nitroimidazolyl] Thiourea, N (4 Sulfamoylphenyl) N [(2 Aminoethyl) 2 Methyl 5 Nitroimidazolyl] Thiourea, N (4 Sulfamoylphenylethyl) N [(2 Aminoethyl) 2 Methyl 5 Nitroimidazolyl] Thiourea, N [2 (2 Methyl 5 Nitro Imidazol 1 Yl)ethyl]sulfamide, N [2 (2 Methyl Imidazol 1 Yl)propyl]sulfamide, N [2 (2 Nitro Imidazol 1 Yl)ethyl]sulfamide, N Methanesulfonyl 1 (2 Aminoethyl) 2 Methyl 5 Nitroimidazole, N Methanesulfonyl 2 (2 Nitro Imidazol 1 Yl)ethylamine, N[2 (2 Methyl 5 Nitro Imidazol 1 Yl)ethyl]sulfamate, Nitroimidazole Derivative, Sulfamide Derivative, Sulfonamide, Tert Butyl (2 Nitro Imidazol 1 Yl) Acetate, Unclassified Drug, Acidosis, Animal Cell, Animal Experiment, Animal Model, Article, Chemosensitization, Controlled Study, Enzyme Active Site, Enzyme Activity, Hela Cell, Human, Human Cell, Hypoxia, In Vitro Study, In Vivo Study, Mouse, Nonhuman, Protein Expression, X Ray Crystallography, Anoxia, Antigens, Carbonic Anhydrases, Dose-Response Relationship, Enzyme Inhibitors, Ht29 Cells, Molecular, Molecular Structure, Structure-Activity Relationship, Sulfonic Acids, Amides Chemistry, Neoplasm Metabolism, Carbonic Anhydrases Metabolism, Enzyme Inhibitors Chemical Synthesis Chemistry Pharmacology, Nitroimidazoles Chemistry, Sulfonamides Chemistry, Sulfonic Acids Chemistry, 2 (2 Nitro Imidazol 1 Yl) N (3 Sulfamoylphenyl) Acetamide, 2 (2 Nitro Imidazol 1 Yl) N (4 Sulfamoylbenzyl) Acetamide, 2 (2 Nitro Imidazol 1 Yl) N (4 Sulfamoylphenyl) Acetamide, 2 (2 Nitro Imidazol 1 Yl) N [2 (4 Sulfamoylphenyl) Ethyl] Acetamide, 2 (2 Nitro Imidazol 1 Yl) Ethylamine, N [2 (2 Methyl 5 Nitro Imidazol 1 Yl) Ethyl] Sulfamide, N [2 (2 Methyl Imidazol 1 Yl) Propyl] Sulfamide, N [2 (2 Nitro Imidazol 1 Yl) Ethyl] Sulfamide, N Methanesulfonyl 2 (2 Nitro Imidazol 1 Yl) Ethylamine, N [2 (2 Methyl 5 Nitro Imidazol 1 Yl) Ethyl] Sulfamate,
Affiliations:
*** IBB - CNR ***
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS-UM1-UM2 Baîtiment de Recherche Max Mousseron, Ecole Nationale Supérieure de Chimie de Montpellier, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex, France
Department of Radiation Oncology (MAASTRO Lab), GROW - School for Oncology and Developmental Biology, Maastricht University Medical Centre, Universiteitssingel 50/23, 6200 MD, Maastricht, Netherlands
Istituto di Biostrutture e Bioimmagini - CNR, via Mezzocannone 16, 80134 Naples, Italy
Neurofarba Department, Section of Pharmaceutical Sciences, Università Degli Studi di Firenze, Via Ugo Schiff 6, 50019 Sesto Fiorentino (Florence), Italy
References:
Wilson, W.R., Hay, M.P., Targeting hypoxia in cancer therapy (2011) Nature Rev. Cancer, 11, pp. 393-41
Bennewith, K.L., Dedhar, S., Targeting hypoxic tumour cells to overcome metastasis (2011) BMC Cancer, 11, p. 504
Supuran, C.T., Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators (2008) Nature Rev. Drug Discovery, 7, pp. 168-181
McDonald, P.C., Winum, J.-Y., Supuran, C.T., Dedhar, S., Recent developments in targeting carbonic anhydrase IX for cancer therapeutics (2012) Oncotarget, 3, pp. 84-97
Neri, D., Supuran, C.T., Interfering with pH regulation in tumours as a therapeutic strategy (2011) Nature Rev. Drug Discovery, 10, pp. 767-777
Pacchiano, F., Carta, F., McDonald, P.C., Lou, Y., Vullo, D., Scozzafava, A., Dedhar, S., Supuran, C.T., Ureido-substituted benzenesulfonamides potently inhibit carbonic anhydrase IX and show antimetastatic activity in a model of breast cancer metastasis (2011) J. Med. Chem., 54, pp. 1896-1902
Touisni, N., Maresca, A., McDonald, P.C., Lou, Y., Scozzafava, A., Dedhar, S., Winum, J.-Y., Supuran, C.T., Glycosyl coumarin carbonic anhydrase IX and XII inhibitors strongly attenuate the growth of primary breast tumors (2011) J. Med. Chem., 54, pp. 8271-8277
Lou, Y., McDonald, P.C., Oloumi, A., Chia, S., Ostlund, C., Ahmadi, A., Kyle, A., Dedhar, S., Targeting tumor hypoxia: Suppression of breast tumor growth and metastasis by novel carbonic anhydrase IX inhibitors (2011) Cancer Res., 71, pp. 3364-3376
Dubois, L., Peeters, S., Lieuwes, N.G., Geusens, N., Thiry, A., Wigfield, S., Carta, F., Lambin, P., Specific inhibition of carbonic anhydrase IX activity enhances the in vivo therapeutic effect of tumor irradiation (2011) Radiother. Oncol., 99, pp. 424-431
Gieling, R.G., Babur, M., Mamnani, L., Burrows, N., Telfer, B.A., Carta, F., Winum, J.-Y., Williams, K.J., Antimetastatic effect of sulfamate carbonic anhydrase IX inhibitors in breast carcinoma xenografts (2012) J. Med. Chem., 55, pp. 5591-5600
Liu, K., Zhu, H.L., Nitroimidazoles as anti-tumor agents (2011) Anti-Cancer Agents Med. Chem., 11, pp. 687-691
Overgaard, J., Overgaard, M., Nielsen, O.S., Pedersen, A.K., Timothy, A.R., A comparative investigation of nimorazole and misonidazole as hypoxic radiosensitizers in a C3H mammary carcinoma in vivo (1982) Br. J. Cancer, 46, pp. 904-911
D'Ambrosio, K., Vitale, R.M., Dogné, J.M., Masereel, B., Innocenti, A., Scozzafava, A., De Simone, G., Supuran, C.T., Carbonic anhydrase inhibitors: Bioreductive nitro-containing sulfonamides with selectivity for targeting the tumor associated isoforms IX and XII (2008) J. Med. Chem., 51, pp. 3230-3237
Rami, M., Cecchi, A., Montero, J.-L., Innocenti, A., Vullo, D., Scozzafava, A., Winum, J.-Y., Supuran, C.T., Carbonic anhydrase inhibitors: Design of membrane-impermeant copper(II) complexes of DTPA-, DOTA-, and TETA-tailed sulfonamides targeting the tumor-associated transmembrane isoform IX (2008) ChemMedChem, 3, pp. 1780-1788
Rami, M., Montero, J.-L., Dubois, L., Lambin, P., Scozzafava, A., Winum, J.-Y., Supuran, C.T., Carbonic anhydrase inhibitors: Gd(III) complexes of DOTA- and TETA-sulfonamide conjugates targeting the tumor associated carbonic anhydrase isozymes IX and XII (2010) New J. Chem., 34, pp. 2139-2144
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
Winum, J.-Y., Carta, F., Ward, C., Mullen, P., Harrison, D., Langdon, S.P., Cecchi, A., Supuran, C.T., Ureido-substituted sulfamates show potent carbonic anhydrase IX inhibitory and antiproliferative activities against breast cancer cell lines (2012) Bioorg. Med. Chem. Lett., 22, pp. 4681-4685
Hoigebazar, L., Jeong, J.M., Choi, S.Y., Choi, J.Y., Shetty, D., Lee, Y.S., Lee, D.S., Chung, Y.K., Synthesis and characterization of nitroimidazole derivatives for 68Ga-labeling and testing in tumor xenografted mice (2010) J. Med. Chem., 53, pp. 6378-6385
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
Dubois, L., Douma, K., Supuran, C.T., Chiu, R.K., Van Zandvoort, M.A., Pastoreková, S., Scozzafava, A., Lambin, P., Imaging the hypoxia surrogate marker CA IX requires expression and catalytic activity for binding fluorescent sulfonamide inhibitors (2007) Radiother. Oncol., 83, pp. 367-373
Eriksson, A.E., Jones, T.A., Liljas, A., Refined structure of human carbonic anhydrase II at 2.0 Å resolution (1988) Proteins, 4, pp. 274-282
Winum, J.-Y., Temperini, C., El Cheikh, K., Innocenti, A., Vullo, D., Ciattini, S., Montero, J.L., Supuran, C.T., Carbonic anhydrase inhibitors: Clash with Ala65 as a means for designing inhibitors with low affinity for the ubiquitous isozyme II, exemplified by the crystal structure of the topiramate sulfamide analogue (2006) J. Med. Chem., 49, pp. 7024-7031
Di Fiore, A., Monti, S.M., Innocenti, A., Winum, J.Y., De Simone, G., Supuran, C.T., Carbonic anhydrase inhibitors: Crystallographic and solution binding studies for the interaction of a boron-containing aromatic sulfamide with mammalian isoforms I-XV (2010) Bioorg. Med. Chem. Lett., 20, pp. 3601-3605
De Simone, G., Alterio, V., Supuran, C.T., Exploiting the hydrophobic and hydrophilic binding sites for designing carbonic anhydrase inhibitors (2013) Expert Opin. Drug Discovery, 8, pp. 793-810
Otwinowski, Z., Minor, W., Processing of X-ray diffraction data collected in oscillation mode (1997) Methods Enzymol., 276, pp. 307-326
Brünger, A.T., Adams, P.D., Clore, G.M., Delano, W.L., Gros, P., Grosse-Kunstleve, R.W., Jiang, J.S., Warren, G.L., (1998) Acta Crystallogr., Sect. D: Biol. Crystallogr., 54, pp. 905-921
Jones, T.A., Zou, J.Y., Cowan, S.W., Kjeldgaard, M., (1991) Acta Crystallogr. Sect. A: Found. Crystallogr., 47, pp. 110-119
Allen, F.H., The Cambridge Structural Database: A quarter of a million crystal structures and rising (2002) Acta Crystallogr., Sect. B: Struct. Sci., 58, pp. 380-388
Wilson, W. R., Hay, M. P., Targeting hypoxia in cancer therapy (2011) Nature Rev. Cancer, 11, pp. 393-41
Bennewith, K. L., Dedhar, S., Targeting hypoxic tumour cells to overcome metastasis (2011) BMC Cancer, 11, p. 504
Supuran, C. T., Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators (2008) Nature Rev. Drug Discovery, 7, pp. 168-181
McDonald, P. C., Winum, J. -Y., Supuran, C. T., Dedhar, S., Recent developments in targeting carbonic anhydrase IX for cancer therapeutics (2012) Oncotarget, 3, pp. 84-97
Gieling, R. G., Babur, M., Mamnani, L., Burrows, N., Telfer, B. A., Carta, F., Winum, J. -Y., Williams, K. J., Antimetastatic effect of sulfamate carbonic anhydrase IX inhibitors in breast carcinoma xenografts (2012) J. Med. Chem., 55, pp. 5591-5600
Liu, K., Zhu, H. L., Nitroimidazoles as anti-tumor agents (2011) Anti-Cancer Agents Med. Chem., 11, pp. 687-691
Winum, J. -Y., Carta, F., Ward, C., Mullen, P., Harrison, D., Langdon, S. P., Cecchi, A., Supuran, C. T., Ureido-substituted sulfamates show potent carbonic anhydrase IX inhibitory and antiproliferative activities against breast cancer cell lines (2012) Bioorg. Med. Chem. Lett., 22, pp. 4681-4685
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, 4, pp. 274-282
Winum, J. -Y., Temperini, C., El Cheikh, K., Innocenti, A., Vullo, D., Ciattini, S., Montero, J. L., Supuran, C. T., Carbonic anhydrase inhibitors: Clash with Ala65 as a means for designing inhibitors with low affinity for the ubiquitous isozyme II, exemplified by the crystal structure of the topiramate sulfamide analogue (2006) J. Med. Chem., 49, pp. 7024-7031
Br nger, A. T., Adams, P. D., Clore, G. M., Delano, W. L., Gros, P., Grosse-Kunstleve, R. W., Jiang, J. S., Warren, G. L., (1998) Acta Crystallogr., Sect. D: Biol. Crystallogr., 54, pp. 905-921
Jones, T. A., Zou, J. Y., Cowan, S. W., Kjeldgaard, M., (1991) Acta Crystallogr. Sect. A: Found. Crystallogr., 47, pp. 110-119
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Hypoxia-targeting carbonic anhydrase IX inhibitors by a new series of nitroimidazole-sulfonamides/sulfamides/sulfamates
A series of nitroimidazoles incorporating sulfonamide/sulfamide/sulfamate moieties were designed and synthesized as radio/chemosensitizing agent targeting the tumor-associated carbonic anhydrase (CA) isoforms IX and XII. Most of the new compounds were nanomolar inhibitors of these isoforms. Crystallographic studies on the complex of hCA II with the lead sulfamide derivative of this series clarified the binding mode of this type of inhibitors in the enzyme active site cavity. Some of the best nitroimidazole CA IX inhibitors showed significant activity in vitro by reducing hypoxia-induced extracellular acidosis in HT-29 and HeLa cell lines. In vivo testing of the lead molecule in the sulfamide series, in cotreatment with doxorubicin, demonstrated a chemosensitization of CA IX containing tumors. Such CA inhibitors, specifically targeting the tumor-associated isoforms, are candidates for novel treatment strategies against hypoxic tumors overexpressing extracellular CA isozymes. © 2013 American Chemical Society.
A series of nitroimidazoles incorporating sulfonamide/sulfamide/sulfamate moieties were designed and synthesized as radio/chemosensitizing agent targeting the tumor-associated carbonic anhydrase (CA) isoforms IX and XII. Most of the new compounds were nanomolar inhibitors of these isoforms. Crystallographic studies on the complex of hCA II with the lead sulfamide derivative of this series clarified the binding mode of this type of inhibitors in the enzyme active site cavity. Some of the best nitroimidazole CA IX inhibitors showed significant activity in vitro by reducing hypoxia-induced extracellular acidosis in HT-29 and HeLa cell lines. In vivo testing of the lead molecule in the sulfamide series, in cotreatment with doxorubicin, demonstrated a chemosensitization of CA IX containing tumors. Such CA inhibitors, specifically targeting the tumor-associated isoforms, are candidates for novel treatment strategies against hypoxic tumors overexpressing extracellular CA isozymes. © 2013 American Chemical Society.
Hypoxia-targeting carbonic anhydrase IX inhibitors by a new series of nitroimidazole-sulfonamides/sulfamides/sulfamates
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