5JEH
 
 | | Human carbonic anhydrase II (L198A) complexed with benzo[d]thiazole-2-sulfonamide | | Descriptor: | 1,3-benzothiazole-2-sulfonamide, Carbonic anhydrase 2, ZINC ION | | Authors: | Fox, J.M, Kang, K, Sastry, M, Sherman, W, Sankaran, B, Zwart, P.H, Whitesides, G.M. | | Deposit date: | 2016-04-18 | | Release date: | 2017-01-11 | | Last modified: | 2023-09-27 | | Method: | X-RAY DIFFRACTION (1.13 Å) | | Cite: | Water-Restructuring Mutations Can Reverse the Thermodynamic Signature of Ligand Binding to Human Carbonic Anhydrase.
Angew. Chem. Int. Ed. Engl., 56, 2017
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5JGS
 | | Human carbonic anhydrase II (F131Y/L198A) complexed with benzo[d]thiazole-2-sulfonamide | | Descriptor: | 1,3-benzothiazole-2-sulfonamide, Carbonic anhydrase 2, ZINC ION | | Authors: | Fox, J.M, Kang, K, Sastry, M, Sherman, W, Sankaran, B, Zwart, P.H, Whitesides, G.M. | | Deposit date: | 2016-04-20 | | Release date: | 2017-01-11 | | Last modified: | 2023-09-27 | | Method: | X-RAY DIFFRACTION (1.11 Å) | | Cite: | Water-Restructuring Mutations Can Reverse the Thermodynamic Signature of Ligand Binding to Human Carbonic Anhydrase.
Angew. Chem. Int. Ed. Engl., 56, 2017
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3E3F
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6EEA
 | | Bioreductive 4-hydroxy-3-nitro-5-ureido-benzenesulfonamides selectively target the tumor-associated carbonic anhydrase isoforms IX and XII and show hypoxia-enhanced cytotoxicity against human cancer cell lines. | | Descriptor: | 4-hydroxy-3-nitro-5-({[4-(trifluoromethyl)phenyl]carbamoyl}amino)benzene-1-sulfonamide, Carbonic anhydrase 2, ZINC ION | | Authors: | Singh, S, McKenna, R, Supuran, C.T, Nocentini, A, Lomelino, C, Lucarini, E, Bartolucci, G, Mannelli, L.D.C, Ghelardini, C, Gratteri, P. | | Deposit date: | 2018-08-13 | | Release date: | 2018-11-28 | | Last modified: | 2023-10-11 | | Method: | X-RAY DIFFRACTION (1.63 Å) | | Cite: | 4-Hydroxy-3-nitro-5-ureido-benzenesulfonamides Selectively Target the Tumor-Associated Carbonic Anhydrase Isoforms IX and XII Showing Hypoxia-Enhanced Antiproliferative Profiles.
J. Med. Chem., 61, 2018
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6EDA
 | | Bioreductive 4-hydroxy-3-nitro-5-ureido-benzenesulfonamides selectively target the tumor-associated carbonic anhydrase isoforms IX and XII and show hypoxia-enhanced cytotoxicity against human cancer cell lines. | | Descriptor: | 4-hydroxy-3-nitro-5-({[4-(trifluoromethyl)phenyl]carbamoyl}amino)benzene-1-sulfonamide, Carbonic anhydrase 2, ZINC ION | | Authors: | Singh, S, McKenna, R, Supuran, C.T, Nocentini, A, Lomelino, C, Lucarini, E, Bartolucci, G, Mannelli, L.D.C, Ghelardini, C, Gratteri, P. | | Deposit date: | 2018-08-09 | | Release date: | 2018-11-28 | | Last modified: | 2023-10-11 | | Method: | X-RAY DIFFRACTION (1.879 Å) | | Cite: | 4-Hydroxy-3-nitro-5-ureido-benzenesulfonamides Selectively Target the Tumor-Associated Carbonic Anhydrase Isoforms IX and XII Showing Hypoxia-Enhanced Antiproliferative Profiles.
J. Med. Chem., 61, 2018
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6EEO
 | | Bioreductive 4-hydroxy-3-nitro-5-ureido-benzenesulfonamides selectively target the tumor-associated carbonic anhydrase isoforms IX and XII and show hypoxia-enhanced cytotoxicity against human cancer cell lines. | | Descriptor: | 3-{[(4-fluoro-3-methylphenyl)carbamoyl]amino}-4-hydroxy-5-nitrobenzene-1-sulfonamide, Carbonic anhydrase 2, ZINC ION | | Authors: | Singh, S, McKenna, R, Supuran, C.T, Nocentini, A, Lomelino, C, Lucarini, E, Bartolucci, G, Mannelli, L.D.C, Ghelardini, C, Gratteri, P. | | Deposit date: | 2018-08-15 | | Release date: | 2018-11-28 | | Last modified: | 2023-10-11 | | Method: | X-RAY DIFFRACTION (1.719 Å) | | Cite: | 4-Hydroxy-3-nitro-5-ureido-benzenesulfonamides Selectively Target the Tumor-Associated Carbonic Anhydrase Isoforms IX and XII Showing Hypoxia-Enhanced Antiproliferative Profiles.
J. Med. Chem., 61, 2018
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3SBI
 | | Crystal structure of human carbonic anhydrase isozyme II with 4-[(2-pyrimidinylsulfanyl)acetyl]benzenesulfonamide | | Descriptor: | 4-[(pyrimidin-2-ylsulfanyl)acetyl]benzenesulfonamide, BICINE, Carbonic anhydrase 2, ... | | Authors: | Grazulis, S, Manakova, E, Tamulaitiene, G. | | Deposit date: | 2011-06-05 | | Release date: | 2012-04-11 | | Last modified: | 2023-09-13 | | Method: | X-RAY DIFFRACTION (1.4 Å) | | Cite: | Design of [(2-pyrimidinylthio)acetyl]benzenesulfonamides as inhibitors of human carbonic anhydrases.
Eur.J.Med.Chem., 51, 2012
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6EBE
 | | Bioreductive 4-hydroxy-3-nitro-5-ureido-benzenesulfonamides selectively target the tumor-associated carbonic anhydrase isoforms IX and XII and show hypoxia-enhanced cytotoxicity against human cancer cell lines. | | Descriptor: | 4-hydroxy-3-nitro-5-({[4-(trifluoromethyl)phenyl]carbamoyl}amino)benzene-1-sulfonamide, Carbonic anhydrase 2, ZINC ION | | Authors: | Singh, S, McKenna, R, Supuran, C.T, Nocentini, A, Lomelino, C, Lucarini, E, Bartolucci, G, Mannelli, L.D.C, Ghelardini, C, Gratteri, P. | | Deposit date: | 2018-08-06 | | Release date: | 2018-11-28 | | Last modified: | 2023-10-11 | | Method: | X-RAY DIFFRACTION (1.88 Å) | | Cite: | 4-Hydroxy-3-nitro-5-ureido-benzenesulfonamides Selectively Target the Tumor-Associated Carbonic Anhydrase Isoforms IX and XII Showing Hypoxia-Enhanced Antiproliferative Profiles.
J. Med. Chem., 61, 2018
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6G7A
 | | Crystal structure of human carbonic anhydrase isozyme XII 2-(benzylamino)-4-chloro-N-(2-hydroxyethyl)-5-sulfamoyl-benzamide | | Descriptor: | 1,2-ETHANEDIOL, 4-chloranyl-~{N}-(2-hydroxyethyl)-2-[(phenylmethyl)amino]-5-sulfamoyl-benzamide, Carbonic anhydrase 12, ... | | Authors: | Smirnov, A, Manakova, E, Grazulis, S. | | Deposit date: | 2018-04-05 | | Release date: | 2019-03-13 | | Last modified: | 2024-01-17 | | Method: | X-RAY DIFFRACTION (1.42 Å) | | Cite: | Design of two-tail compounds with rotationally fixed benzenesulfonamide ring as inhibitors of carbonic anhydrases.
Eur J Med Chem, 156, 2018
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3S9T
 | | Crystal structure of human carbonic anhydrase isozyme II with 2-chloro-5-{[(4,6-dimethyl-2-pyrimidinyl)sulfanyl]acetyl}benzenesulfonamide | | Descriptor: | 2-chloro-5-{[(4,6-dimethylpyrimidin-2-yl)sulfanyl]acetyl}benzenesulfonamide, BICINE, Carbonic anhydrase 2, ... | | Authors: | Grazulis, S, Manakova, E, Tamulaitiene, G. | | Deposit date: | 2011-06-02 | | Release date: | 2012-04-18 | | Last modified: | 2023-09-13 | | Method: | X-RAY DIFFRACTION (1.3 Å) | | Cite: | Design of [(2-pyrimidinylthio)acetyl]benzenesulfonamides as inhibitors of human carbonic anhydrases.
Eur.J.Med.Chem., 51, 2012
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3SAP
 | | Crystal structure of human carbonic anhydrase isozyme II with 4-{[(5-butyl-2-pyrimidinyl)sulfanyl]acetyl}benzenesulfonamide | | Descriptor: | 2-(N-MORPHOLINO)-ETHANESULFONIC ACID, 4-{[(5-butylpyrimidin-2-yl)sulfanyl]acetyl}benzenesulfonamide, BICINE, ... | | Authors: | Grazulis, S, Manakova, E, Tamulaitiene, G. | | Deposit date: | 2011-06-03 | | Release date: | 2012-04-11 | | Last modified: | 2023-09-13 | | Method: | X-RAY DIFFRACTION (1.75 Å) | | Cite: | Design of [(2-pyrimidinylthio)acetyl]benzenesulfonamides as inhibitors of human carbonic anhydrases.
Eur.J.Med.Chem., 51, 2012
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3SAX
 | | Crystal structure of human carbonic anhydrase isozyme II with 2-chloro-5-{[(5-ethyl-2-pyrimidinyl)sulfanyl]acetyl}benzenesulfonamide | | Descriptor: | 2-chloro-5-{[(5-ethylpyrimidin-2-yl)sulfanyl]acetyl}benzenesulfonamide, BICINE, Carbonic anhydrase 2, ... | | Authors: | Grazulis, S, Manakova, E, Tamulaitiene, G. | | Deposit date: | 2011-06-03 | | Release date: | 2012-04-11 | | Last modified: | 2023-09-13 | | Method: | X-RAY DIFFRACTION (1.1 Å) | | Cite: | Design of [(2-pyrimidinylthio)acetyl]benzenesulfonamides as inhibitors of human carbonic anhydrases.
Eur.J.Med.Chem., 51, 2012
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6G5L
 | | Crystal structure of human carbonic anhydrase isozyme XII with 4-chloro-2-(cyclohexylamino)-N-(2-hydroxyethyl)-5-sulfamoyl-benzamide | | Descriptor: | 1,2-ETHANEDIOL, 4-chloranyl-2-(cyclohexylamino)-~{N}-(2-hydroxyethyl)-5-sulfamoyl-benzamide, Carbonic anhydrase 12, ... | | Authors: | Smirnov, A, Manakova, E, Grazulis, S. | | Deposit date: | 2018-03-29 | | Release date: | 2019-03-13 | | Last modified: | 2024-01-17 | | Method: | X-RAY DIFFRACTION (1.21 Å) | | Cite: | Design of two-tail compounds with rotationally fixed benzenesulfonamide ring as inhibitors of carbonic anhydrases.
Eur J Med Chem, 156, 2018
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3CA2
 | | CRYSTALLOGRAPHIC STUDIES OF INHIBITOR BINDING SITES IN HUMAN CARBONIC ANHYDRASE II. A PENTACOORDINATED BINDING OF THE SCN-ION TO THE ZINC AT HIGH P*H | | Descriptor: | 3-MERCURI-4-AMINOBENZENESULFONAMIDE, CARBONIC ANHYDRASE II, MERCURY (II) ION, ... | | Authors: | Eriksson, A.E, Jones, T.A, Liljas, A. | | Deposit date: | 1989-10-02 | | Release date: | 1990-01-15 | | Last modified: | 2024-02-21 | | Method: | X-RAY DIFFRACTION (2 Å) | | Cite: | Crystallographic studies of inhibitor binding sites in human carbonic anhydrase II: a pentacoordinated binding of the SCN- ion to the zinc at high pH.
Proteins, 4, 1988
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3S76
 | | The origin of the hydrophobic effect in the molecular recognition of arylsulfonamides by carbonic anhydrase | | Descriptor: | 1H-imidazole-2-sulfonamide, Carbonic anhydrase 2, DIMETHYL SULFOXIDE, ... | | Authors: | Snyder, P.W, Heroux, A, Whitesides, G.W. | | Deposit date: | 2011-05-26 | | Release date: | 2011-10-19 | | Last modified: | 2024-02-28 | | Method: | X-RAY DIFFRACTION (1.6 Å) | | Cite: | Mechanism of the hydrophobic effect in the biomolecular recognition of arylsulfonamides by carbonic anhydrase.
Proc.Natl.Acad.Sci.USA, 108, 2011
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3S73
 | | The origin of the hydrophobic effect in the molecular recognition of arylsulfonamides by carbonic anhydrase | | Descriptor: | 1,3-benzothiazole-2-sulfonamide, Carbonic anhydrase 2, ZINC ION | | Authors: | Snyder, P.W, Heroux, A, Whitesides, G.W. | | Deposit date: | 2011-05-26 | | Release date: | 2011-12-21 | | Last modified: | 2024-02-28 | | Method: | X-RAY DIFFRACTION (1.75 Å) | | Cite: | Mechanism of the hydrophobic effect in the biomolecular recognition of arylsulfonamides by carbonic anhydrase.
Proc.Natl.Acad.Sci.USA, 108, 2011
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3S71
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5DOG
 | | Crystal structure of human carbonic anhydrase isozyme II with 2-(Benzylamino)-3,5,6-trifluoro-4-[(2-phenylethyl)thio]benzene- sulfonamide | | Descriptor: | 2-(N-MORPHOLINO)-ETHANESULFONIC ACID, 2-(benzylamino)-3,5,6-trifluoro-4-[(2-phenylethyl)sulfanyl]benzenesulfonamide, BICINE, ... | | Authors: | Smirnov, A, Manakova, E, Grazulis, S. | | Deposit date: | 2015-09-11 | | Release date: | 2016-09-28 | | Last modified: | 2024-01-10 | | Method: | X-RAY DIFFRACTION (1.7 Å) | | Cite: | Intrinsic Thermodynamics and Structures of 2,4- and 3,4-Substituted Fluorinated Benzenesulfonamides Binding to Carbonic Anhydrases.
ChemMedChem, 12, 2017
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5DOH
 | | Crystal structure of human carbonic anhydrase isozyme II with 2-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]-3,5,6-trifluoro-4-[(2-hydroxyethyl)thio]benzenesulfonamide | | Descriptor: | 2-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-3,5,6-trifluoro-4-[(2-hydroxyethyl)sulfanyl]benzenesulfonamide, BICINE, Carbonic anhydrase 2, ... | | Authors: | Smirnov, A, Manakova, E, Grazulis, S. | | Deposit date: | 2015-09-11 | | Release date: | 2016-09-28 | | Last modified: | 2024-01-10 | | Method: | X-RAY DIFFRACTION (1.05 Å) | | Cite: | Intrinsic Thermodynamics and Structures of 2,4- and 3,4-Substituted Fluorinated Benzenesulfonamides Binding to Carbonic Anhydrases.
ChemMedChem, 12, 2017
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5E2M
 | | Crystal structure of human carbonic anhydrase isozyme I with 3-(cyclooctylamino)-2,5,6-trifluoro-4-[(2-hydroxyethyl)sulfonyl]benzenesulfonamide | | Descriptor: | 3-(cyclooctylamino)-2,5,6-trifluoro-4-[(2-hydroxyethyl)sulfonyl]benzenesulfonamide, ACETATE ION, Carbonic anhydrase 1, ... | | Authors: | Manakova, E, Smirnov, A, Grazulis, S. | | Deposit date: | 2015-10-01 | | Release date: | 2016-10-05 | | Last modified: | 2024-01-10 | | Method: | X-RAY DIFFRACTION (1.41 Å) | | Cite: | Intrinsic Thermodynamics and Structures of 2,4- and 3,4-Substituted Fluorinated Benzenesulfonamides Binding to Carbonic Anhydrases.
ChemMedChem, 12, 2017
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5EHE
 | | Crystal structure of human carbonic anhydrase isozyme II with 3-(benzylamino)-2,5,6-trifluoro-4-[(2-hydroxyethyl)sulfonyl]benzenesulfonamide | | Descriptor: | 2-(N-MORPHOLINO)-ETHANESULFONIC ACID, 3-(benzylamino)-2,5,6-trifluoro-4-[(2-hydroxyethyl)sulfonyl]benzenesulfonamide, Carbonic anhydrase 2, ... | | Authors: | Smirnov, A, Manakova, E, Grazulis, S. | | Deposit date: | 2015-10-28 | | Release date: | 2016-11-09 | | Last modified: | 2024-01-10 | | Method: | X-RAY DIFFRACTION (1.5 Å) | | Cite: | Intrinsic Thermodynamics and Structures of 2,4- and 3,4-Substituted Fluorinated Benzenesulfonamides Binding to Carbonic Anhydrases.
ChemMedChem, 12, 2017
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2EU3
 | | Human Carbonic anhydrase II in complex with novel inhibitors | | Descriptor: | 1-(5-AMINO-1,3,4-THIADIAZOL-2-YL)-1,1-DIFLUOROMETHANESULFONAMIDE, Carbonic anhydrase 2, ZINC ION | | Authors: | Fisher, S.Z, Govindasamy, L, Boyle, N, Agbandje-McKenna, M, Silverman, D.N, Blackburn, G.M, McKenna, R. | | Deposit date: | 2005-10-28 | | Release date: | 2006-07-11 | | Last modified: | 2023-08-23 | | Method: | X-RAY DIFFRACTION (1.6 Å) | | Cite: | X-ray crystallographic studies reveal that the incorporation of spacer groups in carbonic anhydrase inhibitors causes alternate binding modes.
Acta Crystallogr.,Sect.F, 62, 2006
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3SBH
 | | Crystal structure of human carbonic anhydrase isozyme II with 4-{[(4,6-dimethyl-2-pyrimidinyl)sulfanyl]acetyl}benzenesulfonamide | | Descriptor: | 2-(N-MORPHOLINO)-ETHANESULFONIC ACID, 4-{[(4,6-dimethylpyrimidin-2-yl)sulfanyl]acetyl}benzenesulfonamide, BICINE, ... | | Authors: | Grazulis, S, Manakova, E, Tamulaitiene, G. | | Deposit date: | 2011-06-05 | | Release date: | 2012-04-11 | | Last modified: | 2023-09-13 | | Method: | X-RAY DIFFRACTION (1.65 Å) | | Cite: | Design of [(2-pyrimidinylthio)acetyl]benzenesulfonamides as inhibitors of human carbonic anhydrases.
Eur.J.Med.Chem., 51, 2012
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1AZM
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3S72
 | | The origin of the hydrophobic effect in the molecular recognition of arylsulfonamides by carbonic anhydrase | | Descriptor: | 1H-benzimidazole-2-sulfonamide, Carbonic anhydrase 2, DIMETHYL SULFOXIDE, ... | | Authors: | Snyder, P.W, Heroux, A, Whitesides, G.W. | | Deposit date: | 2011-05-26 | | Release date: | 2011-10-19 | | Last modified: | 2024-02-28 | | Method: | X-RAY DIFFRACTION (1.6 Å) | | Cite: | Mechanism of the hydrophobic effect in the biomolecular recognition of arylsulfonamides by carbonic anhydrase.
Proc.Natl.Acad.Sci.USA, 108, 2011
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