메뉴 건너뛰기




Volumn 49, Issue 9, 2006, Pages 2743-2749

Indanesulfonamides as carbonic anhydrase inhibitors. Toward structure-based design of selective inhibitors of the tumor-associated isozyme CA IX

Author keywords

[No Author keywords available]

Indexed keywords

1 PENTAFLUOROPHENYLAMIDO 5 SULFONAMIDOINDANE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IX INHIBITOR; INDANESULFONAMIDE DERIVATIVE; ISOENZYME; UNCLASSIFIED DRUG;

EID: 33646446585     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0600287     Document Type: Article
Times cited : (62)

References (48)
  • 1
    • 2442579987 scopus 로고    scopus 로고
    • Carbonic anhydrases: Catalytic and inhibition mechanisms, distribution and physiological roles
    • CRC Press: London
    • Supuran, C. T. Carbonic Anhydrases: Catalytic and Inhibition Mechanisms, Distribution and Physiological Roles. Carbonic Anhyrdase. Its Inhibitors and Activators; CRC Press: London, 2004; pp 1-23.
    • (2004) Carbonic Anhyrdase. Its Inhibitors and Activators , pp. 1-23
    • Supuran, C.T.1
  • 2
    • 12344264762 scopus 로고    scopus 로고
    • Carbonic anhydrases in normal gastrointestinal tract and gastrointestinal tumours
    • Kivela, A. J.; Kivela, J.; Saarnio, J.; Parkkila, S. Carbonic anhydrases in normal gastrointestinal tract and gastrointestinal tumours. World J. Gastroenterol. 2005, 11, 155-163.
    • (2005) World J. Gastroenterol. , vol.11 , pp. 155-163
    • Kivela, A.J.1    Kivela, J.2    Saarnio, J.3    Parkkila, S.4
  • 4
    • 0034018870 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors and their therapeutic potential
    • Supuran, C. T.; Scozzafava, A. Carbonic anhydrase inhibitors and their therapeutic potential. Exp. Opin. Ther. Pat. 2000, 10, 575-600.
    • (2000) Exp. Opin. Ther. Pat. , vol.10 , pp. 575-600
    • Supuran, C.T.1    Scozzafava, A.2
  • 7
    • 0000582839 scopus 로고    scopus 로고
    • Respiratory and renal roles of carbonic anhydrase in gas exchange and acid-base regulation
    • Birkhäuser Verlag: Basel, Boston, Berlin
    • Swenson, E. R. Respiratory and renal roles of carbonic anhydrase in gas exchange and acid-base regulation. The Carbonic Anhydrases New Horizons; Birkhäuser Verlag: Basel, Boston, Berlin, 2000.
    • (2000) The Carbonic Anhydrases New Horizons
    • Swenson, E.R.1
  • 8
    • 0034577820 scopus 로고    scopus 로고
    • The roles of carbonic anhydrase in metabolism, cell growth and cancer in animals
    • Birkäuser Verlag: Basel, Boston, Berlin.
    • Chegwidden, W. R.; Dodgson, S. J.; Spencer, I. M. The roles of carbonic anhydrase in metabolism, cell growth and cancer in animals. The carbonic anhydrases New Horizons; Birkäuser Verlag: Basel, Boston, Berlin. 2000; pp 343-363.
    • (2000) The Carbonic Anhydrases New Horizons , pp. 343-363
    • Chegwidden, W.R.1    Dodgson, S.J.2    Spencer, I.M.3
  • 12
    • 0035503362 scopus 로고    scopus 로고
    • Expression of hypoxia-inducible carbonic anhydrase-9 relates to angiogenic pathways and independently to poor outcome in non small cell lung cancer
    • Giatromanolaki, A.; Koukourakis, M. I.; Sivridis, E.; Pastorek, J.; Wykoff, C. C.; Gatter, K. C.; Harris, A. L. Expression of hypoxia-inducible carbonic anhydrase-9 relates to angiogenic pathways and independently to poor outcome in non small cell lung cancer. Cancer Res. 2001, 61, 7992-7998.
    • (2001) Cancer Res. , vol.61 , pp. 7992-7998
    • Giatromanolaki, A.1    Koukourakis, M.I.2    Sivridis, E.3    Pastorek, J.4    Wykoff, C.C.5    Gatter, K.C.6    Harris, A.L.7
  • 14
    • 0034024783 scopus 로고    scopus 로고
    • Human tumour-associated cell adhesion protein MN/CA IX: Identification of M75 epitope and of the region mediating cell adhesion
    • Zavada, J.; Zavadova, Z.; Pastorek, J.; Biesova, Z.; Jezek, J.; Velek, J. Human tumour-associated cell adhesion protein MN/CA IX: identification of M75 epitope and of the region mediating cell adhesion. Br. J. Cancer 2000, 82, 1808-1813.
    • (2000) Br. J. Cancer , vol.82 , pp. 1808-1813
    • Zavada, J.1    Zavadova, Z.2    Pastorek, J.3    Biesova, Z.4    Jezek, J.5    Velek, J.6
  • 15
    • 0033986761 scopus 로고    scopus 로고
    • Causes and consequences of tumour acidity and implications for treatment
    • Stubbs, M.; McSheehy, P. M.; Griffiths, J. R.; Bashford, C. L. Causes and consequences of tumour acidity and implications for treatment. Mol. Med. Today 2000, 6, 15-19.
    • (2000) Mol. Med. Today , vol.6 , pp. 15-19
    • Stubbs, M.1    McSheehy, P.M.2    Griffiths, J.R.3    Bashford, C.L.4
  • 16
    • 0034662635 scopus 로고    scopus 로고
    • Acidic pH-induced elevation in interleukin 8 expression by human ovarian carcinoma cells
    • Xu, L.; Fidler, I. J. Acidic pH-induced elevation in interleukin 8 expression by human ovarian carcinoma cells. Cancer Res. 2000, 60, 4610-4616.
    • (2000) Cancer Res. , vol.60 , pp. 4610-4616
    • Xu, L.1    Fidler, I.J.2
  • 17
    • 0035881307 scopus 로고    scopus 로고
    • Hypoxia and acidosis independently up-regulate vascular endothelial growth factor transcription in brain tumors in vivo
    • Fukumura, D.; Xu, L.; Chen, Y.; Gohongi, T.; Seed, B.; Jain, R. K. Hypoxia and acidosis independently up-regulate vascular endothelial growth factor transcription in brain tumors in vivo. Cancer Res. 2001, 61, 6020-6024.
    • (2001) Cancer Res. , vol.61 , pp. 6020-6024
    • Fukumura, D.1    Xu, L.2    Chen, Y.3    Gohongi, T.4    Seed, B.5    Jain, R.K.6
  • 18
    • 0026667311 scopus 로고
    • Induction of 103-kDa gelatinase/type IV collagenase by acidic culture conditions in mouse metastatic melanoma cell lines
    • Kato, Y.; Nakayama, Y.; Umeda, M.; Miyazaki, K. Induction of 103-kDa gelatinase/type IV collagenase by acidic culture conditions in mouse metastatic melanoma cell lines. J. Biol. Chem. 1992, 267, 11424-11430.
    • (1992) J. Biol. Chem. , vol.267 , pp. 11424-11430
    • Kato, Y.1    Nakayama, Y.2    Umeda, M.3    Miyazaki, K.4
  • 19
    • 0029753768 scopus 로고    scopus 로고
    • Genetic instability induced by the tumor microenvironment
    • Reynolds, T. Y.; Rockwell, S.; Glazer, P. M. Genetic instability induced by the tumor microenvironment. Cancer Res. 1996, 56, 5754-5757.
    • (1996) Cancer Res. , vol.56 , pp. 5754-5757
    • Reynolds, T.Y.1    Rockwell, S.2    Glazer, P.M.3
  • 21
    • 0032514685 scopus 로고    scopus 로고
    • Down-regulation of transmembrane carbonic anhydrases in renal cell carcinoma cell lines by wild-type von Hippel-Lindau transgenes
    • Ivanov, S. V.; Kuzmin, I.; Wei, M. H.; Pack, S.; Geil, L.; Johnson, B. E.; Stanbridge, E. J.; Lerman, M. I. Down-regulation of transmembrane carbonic anhydrases in renal cell carcinoma cell lines by wild-type von Hippel-Lindau transgenes. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 12596-12601.
    • (1998) Proc. Natl. Acad. Sci. U.S.A. , vol.95 , pp. 12596-12601
    • Ivanov, S.V.1    Kuzmin, I.2    Wei, M.H.3    Pack, S.4    Geil, L.5    Johnson, B.E.6    Stanbridge, E.J.7    Lerman, M.I.8
  • 24
    • 0027367258 scopus 로고
    • A carbonic anhydrase inhibitor as a potential modulator of cancer therapies
    • Teicher, B. A.; Liu, S. D.; Liu, J. T.; Holden, S. A.; Herman, T. S. A carbonic anhydrase inhibitor as a potential modulator of cancer therapies. Anticancer Res. 1993, 13, 1549-1556.
    • (1993) Anticancer Res. , vol.13 , pp. 1549-1556
    • Teicher, B.A.1    Liu, S.D.2    Liu, J.T.3    Holden, S.A.4    Herman, T.S.5
  • 25
    • 0030942009 scopus 로고    scopus 로고
    • Influence of low pH on cytotoxicity of paclitaxel, mitoxantrone and topotecan
    • Vukovic, V.; Tannock, I. F. Influence of low pH on cytotoxicity of paclitaxel, mitoxantrone and topotecan. Br. J. Cancer 1997, 75, 1167-1172.
    • (1997) Br. J. Cancer , vol.75 , pp. 1167-1172
    • Vukovic, V.1    Tannock, I.F.2
  • 27
    • 5144224910 scopus 로고    scopus 로고
    • Development of carbonic anhydrase inhibitors. Carbonic Anhyrdase
    • CRC Press: London
    • Supuran, C. T.; Casini, A.; Scozzafava, A. Development of carbonic anhydrase inhibitors. Carbonic Anhyrdase. Its Inhibitors and Activators; CRC Press: London, 2004; pp 67-147.
    • (2004) Its Inhibitors and Activators , pp. 67-147
    • Supuran, C.T.1    Casini, A.2    Scozzafava, A.3
  • 28
    • 0034676310 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Perfluoroalkyl/aryl-substituted derivatives of aromatic/heterocyclic sulfonamides as topical intraocular pressure-lowering agents with prolonged duration of action
    • Scozzafava, A.; Menabuoni, L.; Mincione, F.; Briganti, F.; Mincione, G.; Supuran, C. T. Carbonic anhydrase inhibitors: perfluoroalkyl/aryl-substituted derivatives of aromatic/heterocyclic sulfonamides as topical intraocular pressure-lowering agents with prolonged duration of action. J. Med. Chem. 2000, 43, 4542-4551.
    • (2000) J. Med. Chem. , vol.43 , pp. 4542-4551
    • Scozzafava, A.1    Menabuoni, L.2    Mincione, F.3    Briganti, F.4    Mincione, G.5    Supuran, C.T.6
  • 29
    • 0037122779 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Anticonvulsant sulfonamides incorporating valproyl and other lipophilic moieties
    • Masereel, B.; Rolin, S.; Abbate, F.; Scozzafava, A.; Supuran, C. T, Carbonic anhydrase inhibitors: Anticonvulsant sulfonamides incorporating valproyl and other lipophilic moieties. J. Med. Chem. 2002, 45, 312-320.
    • (2002) J. Med. Chem. , vol.45 , pp. 312-320
    • Masereel, B.1    Rolin, S.2    Abbate, F.3    Scozzafava, A.4    Supuran, C.T.5
  • 32
    • 1342304082 scopus 로고    scopus 로고
    • Expression, assay, and structure of the extracellular domain of murine carbonic anhydrase XIV: Implications for selective inhibition of membrane-associated isozymes
    • Whittington, D. A.; Grubb, J. H.; Waheed, A.; Shah, G. N.; Sly, W. S.; Christianson, D. W. Expression, assay, and structure of the extracellular domain of murine carbonic anhydrase XIV: implications for selective inhibition of membrane-associated isozymes. J. Biol. Chem. 2004, 279, 7223-7228.
    • (2004) J. Biol. Chem. , vol.279 , pp. 7223-7228
    • Whittington, D.A.1    Grubb, J.H.2    Waheed, A.3    Shah, G.N.4    Sly, W.S.5    Christianson, D.W.6
  • 33
    • 0031302732 scopus 로고    scopus 로고
    • Assessment of comparative modeling in CASP2
    • Martin, A. C.; MacArthur, M. W.; Thornton, J. M. Assessment of comparative modeling in CASP2. Proteins 1997, (Suppl I), 14-28.
    • (1997) Proteins , Issue.SUPPL. I , pp. 14-28
    • Martin, A.C.1    MacArthur, M.W.2    Thornton, J.M.3
  • 36
    • 0000243829 scopus 로고
    • Procheck: A program to check the stereochemical quality of protein structures
    • Laskowski, R. A. Procheck: a program to check the stereochemical quality of protein structures. J. Appl. Crystallogr. 1993, 26, 283-291.
    • (1993) J. Appl. Crystallogr. , vol.26 , pp. 283-291
    • Laskowski, R.A.1
  • 37
    • 0031887344 scopus 로고    scopus 로고
    • Structures of murine carbonic anhydrase IV and human carbonic anhydrase II complexed with brinzolamide: Molecular basis of isozyme-drug discrimination
    • Stams, T.; Chen, Y.; Boriack-Sjodin, P. A.; Hurt, J. D.; Liao, J.; May, J. A.; Dean, T.; Laipis, P.; Silverman, D. N.; Christianson, D. W. Structures of murine carbonic anhydrase IV and human carbonic anhydrase II complexed with brinzolamide: molecular basis of isozyme-drug discrimination. Protein Sci. 1998, 7, 556-563.
    • (1998) Protein Sci. , vol.7 , pp. 556-563
    • Stams, T.1    Chen, Y.2    Boriack-Sjodin, P.A.3    Hurt, J.D.4    Liao, J.5    May, J.A.6    Dean, T.7    Laipis, P.8    Silverman, D.N.9    Christianson, D.W.10
  • 38
    • 24744467784 scopus 로고    scopus 로고
    • 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
    • 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. J. Med. Chem. 2005, 48, 5721-5727.
    • (2005) J. Med. Chem. , vol.48 , pp. 5721-5727
    • Menchise, V.1    De Simone, G.2    Alterio, V.3    Di Fiore, A.4    Pedone, C.5    Scozzafava, A.6    Supuran, C.T.7
  • 40
    • 1842628633 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Design of selective, membrane-impermeant inhibitors targeting the human tumor-associated isozyme IX
    • Casey, J. R.; Morgan, P. E.; Vullo, D.; Scozzafava, A.; Mastrolorenzo, A.; Supuran, C. T. Carbonic anhydrase inhibitors. Design of selective, membrane-impermeant inhibitors targeting the human tumor-associated isozyme IX. J. Med. Chem. 2004, 47, 2337-2347.
    • (2004) J. Med. Chem. , vol.47 , pp. 2337-2347
    • Casey, J.R.1    Morgan, P.E.2    Vullo, D.3    Scozzafava, A.4    Mastrolorenzo, A.5    Supuran, C.T.6
  • 41
    • 0034719437 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Synthesis of membrane-impermeant low molecular weight sulfonamides possessing in vivo selectivity for the membrane-bound versus cytosolic isozymes
    • Scozzafava, A.; Briganti, F.; ILies, M. A.; Supuran, C. T. Carbonic anhydrase inhibitors: synthesis of membrane-impermeant low molecular weight sulfonamides possessing in vivo selectivity for the membrane-bound versus cytosolic isozymes. J. Med. Chem. 2000, 43, 292-300.
    • (2000) J. Med. Chem. , vol.43 , pp. 292-300
    • Scozzafava, A.1    Briganti, F.2    Ilies, M.A.3    Supuran, C.T.4
  • 43
    • 1242318777 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme V with aromatic and heterocyclic sulfonamides
    • Vullo, D.; Franchi, M.; Gallon, E.; Antel, J.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme V with aromatic and heterocyclic sulfonamides. J. Med. Chem. 2004, 47, 1272-1279.
    • (2004) J. Med. Chem. , vol.47 , pp. 1272-1279
    • Vullo, D.1    Franchi, M.2    Gallon, E.3    Antel, J.4    Scozzafava, A.5    Supuran, C.T.6
  • 44
    • 0015239422 scopus 로고
    • The carbon dioxide hydration activity of carbonic anhydrase. 1. Stop-flow kinetic studies on the native human isoenzymes B and C
    • Khalifah, R. G. The carbon dioxide hydration activity of carbonic anhydrase. 1. Stop-flow kinetic studies on the native human isoenzymes B and C. J. Biol. Chem. 1971, 246, 2561-2573.
    • (1971) J. Biol. Chem. , vol.246 , pp. 2561-2573
    • Khalifah, R.G.1
  • 45
    • 0035859892 scopus 로고    scopus 로고
    • Crystal structure of the dimeric extracellular domain of human carbonic anhydrase XII, a bitopic membrane protein overexpressed in certain cancer tumor cells
    • Whittington, D. A.; Waheed, A.; Ulmasov, B.; Shah, G. N.; Grubb, J. H.; Sly, W. S.; Christianson, D. W. Crystal structure of the dimeric extracellular domain of human carbonic anhydrase XII, a bitopic membrane protein overexpressed in certain cancer tumor cells. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 9545-9550.
    • (2001) Proc. Natl. Acad. Sci. U.S.A. , vol.98 , pp. 9545-9550
    • Whittington, D.A.1    Waheed, A.2    Ulmasov, B.3    Shah, G.N.4    Grubb, J.H.5    Sly, W.S.6    Christianson, D.W.7
  • 46
    • 60349111326 scopus 로고    scopus 로고
    • Accelrys Inc.: San Diego
    • Accelrys, Discover3, Version 2.98 ed.; Accelrys Inc.: San Diego, 1998.
    • (1998) Discover3, Version 2.98 Ed.
  • 47
    • 0004201905 scopus 로고    scopus 로고
    • Accelrys Inc.: San Diego
    • Accelrys, InsightII; Accelrys Inc.: San Diego, 2000.
    • (2000) InsightII
  • 48
    • 0024218271 scopus 로고
    • Refined structure of human carbonic anhydrase II at 2.0 a resolution
    • Eriksson, A. E.; Jones, T. A.; Liljas, A. Refined structure of human carbonic anhydrase II at 2.0 A resolution. Proteins 1988, 4, 274-282.
    • (1988) Proteins , vol.4 , pp. 274-282
    • Eriksson, A.E.1    Jones, T.A.2    Liljas, A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.