메뉴 건너뛰기




Volumn 48, Issue 15, 2005, Pages 4834-4841

Carbonic anhydrase inhibitors. Design of fluorescent sulfonamides as probes of tumor-associated carbonic anhydrase IX that inhibit isozyme IX-mediated acidification of hypoxic tumors

Author keywords

[No Author keywords available]

Indexed keywords

(4 SULFAMOYLPHENYL)THIOUREIDOFLUORESCEIN; 4 AMINOETHYLBENZENESULFONAMIDE; ACETAZOLAMIDE; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IX; CARBONIC ANHYDRASE IX INHIBITOR; DICLOFENAMIDE; ETHOXZOLAMIDE; INDISULAM; ISOENZYME; METHAZOLAMIDE; SULFONAMIDE; UNCLASSIFIED DRUG;

EID: 22744446294     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0501073     Document Type: Article
Times cited : (208)

References (42)
  • 4
    • 4544388351 scopus 로고    scopus 로고
    • Cancer-related carbonic anhydrase isozymes
    • Supuran, C. T., Scozzafava, A., Conway, J., Eds.; CRC Press: Boca Raton, FL
    • (a) Pastorekova, S.; Pastorek, J. Cancer-related carbonic anhydrase isozymes. In Carbonic Anhydrase - Its Inhibitors and Activators; Supuran, C. T., Scozzafava, A., Conway, J., Eds.; CRC Press: Boca Raton, FL, 2004; pp 253-280.
    • (2004) Carbonic Anhydrase - Its Inhibitors and Activators , pp. 253-280
    • Pastorekova, S.1    Pastorek, J.2
  • 5
    • 16544390541 scopus 로고    scopus 로고
    • Carbonic anhydrases: Current state of the art, therapeutic applications and future prospects
    • (b) Pastorekova, S.; Parkkila, S.; Pastorek, J.; Supuran, C. T. Carbonic anhydrases: current state of the art, therapeutic applications and future prospects. J. Enzyme Inhib. Med. Chem. 2004, 19, 199-229.
    • (2004) J. Enzyme Inhib. Med. Chem. , vol.19 , pp. 199-229
    • Pastorekova, S.1    Parkkila, S.2    Pastorek, J.3    Supuran, C.T.4
  • 8
    • 0027367258 scopus 로고
    • A carbonic anhydrase inhibitor as a potential modulator of cancer therapies
    • (b) 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
  • 9
    • 0033818044 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors - Part 94. 1,3,4-Thiadiazole-2-sulfonamide derivatives as antitumor agents?
    • (a) Supuran, C. T.; Scozzafava, A. Carbonic anhydrase inhibitors - Part 94. 1,3,4-Thiadiazole-2-sulfonamide derivatives as antitumor agents? Eur. J. Med. Chem. 2000, 35, 867-874.
    • (2000) Eur. J. Med. Chem. , vol.35 , pp. 867-874
    • Supuran, C.T.1    Scozzafava, A.2
  • 10
    • 0033746355 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Aromatic sulfonamides and disulfonamides act as efficient tumor growth inhibitors
    • (b) Supuran, C. T.; Scozzafava, A. Carbonic anhydrase inhibitors: Aromatic sulfonamides and disulfonamides act as efficient tumor growth inhibitors. J. Enzyme Inhib. 2000, 15, 597-610.
    • (2000) J. Enzyme Inhib. , vol.15 , pp. 597-610
    • Supuran, C.T.1    Scozzafava, A.2
  • 11
    • 0034658561 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Synthesis of N-morpholyl- thiocarbonylsulfenylamino aromatic/heterocyclic sulfonamides and their interaction with isozymes I, II and IV
    • (a) Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors: synthesis of N-morpholyl-thiocarbonylsulfenylamino aromatic/heterocyclic sulfonamides and their interaction with isozymes I, II and IV. Bioorg. Med. Chem. Lett. 2000, 10, 1117-1120.
    • (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 1117-1120
    • Scozzafava, A.1    Supuran, C.T.2
  • 14
  • 17
    • 0042847064 scopus 로고    scopus 로고
    • Diagnostics, prognostics and therapeutic implications of carbonic anhydrases in cancer
    • Potter, C. P. S.; Harris, A. L. Diagnostics, prognostics and therapeutic implications of carbonic anhydrases in cancer. Br. J. Cancer 2003, 89, 2-7.
    • (2003) Br. J. Cancer , vol.89 , pp. 2-7
    • Potter, C.P.S.1    Harris, A.L.2
  • 20
    • 0142166332 scopus 로고    scopus 로고
    • Targeting HIF-1 for cancer therapy
    • Semenza, G. L. Targeting HIF-1 for cancer therapy. Nat. Rev. Cancer 2003, 3, 721-732.
    • (2003) Nat. Rev. Cancer , vol.3 , pp. 721-732
    • Semenza, G.L.1
  • 21
    • 0033986761 scopus 로고    scopus 로고
    • Causes and consequences of tumor acidity and implications for treatment
    • (a) Stubbs, M.; McSheehy, P. M. J.; Griffiths, J. R.; Bashford, C. L. Causes and consequences of tumor 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.J.2    Griffiths, J.R.3    Bashford, C.L.4
  • 22
    • 0036554644 scopus 로고    scopus 로고
    • Acid production in glycolysis-impaired tumors provides new insights into tumor metabolism
    • (b) Helmlinger, G.; Sckell, A.; Dellian, M.; Forbes, N. S.; Jain, R. K. Acid production in glycolysis-impaired tumors provides new insights into tumor metabolism. Clin. Cancer Res. 2002, 8, 1284-1291.
    • (2002) Clin. Cancer Res. , vol.8 , pp. 1284-1291
    • Helmlinger, G.1    Sckell, A.2    Dellian, M.3    Forbes, N.S.4    Jain, R.K.5
  • 23
    • 0035881307 scopus 로고    scopus 로고
    • Hypoxia and acidosis independently up-regulate vascular endothelial growth factor transcription in brain tumors in vivo
    • (a) 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
  • 24
    • 0026667311 scopus 로고
    • Induction of 103-kDa gelatinase/type IV collagenase by acidic culture conditions in mouse metastatic melanoma cell lines
    • (b) 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
  • 27
    • 0034649604 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Water soluble 4-sulfamoylphenyl-thioureas as topical intraocular pressure lowering agents with long lasting effects
    • (a) Casini, A.; Scozzafava, A.; Mincione, F.; Menabuoni, L.; Hies, M. A.; Supuran, C. T. Carbonic anhydrase inhibitors. Water soluble 4-sulfamoylphenyl-thioureas as topical intraocular pressure lowering agents with long lasting effects. J. Med. Chem. 2000, 43, 4884-4892.
    • (2000) J. Med. Chem. , vol.43 , pp. 4884-4892
    • Casini, A.1    Scozzafava, A.2    Mincione, F.3    Menabuoni, L.4    Hies, M.A.5    Supuran, C.T.6
  • 28
    • 4744371616 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: The first on-resin screening of a 4-sulfamoylphenylthiourea library
    • (b) Innocenti, A.; Casini, A.; Alcaro, A. C.; Papini, A. M.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors: The first on-resin screening of a 4-sulfamoylphenylthiourea library. J. Med. Chem. 2004, 47, 5224-5229.
    • (2004) J. Med. Chem. , vol.47 , pp. 5224-5229
    • Innocenti, A.1    Casini, A.2    Alcaro, A.C.3    Papini, A.M.4    Scozzafava, A.5    Supuran, C.T.6
  • 29
    • 0032007213 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Part 49. Synthesis of substituted ureido-and thioureido derivatives of aromatic/heterocyclic sulfonamides with increased affinities for isozyme I
    • Supuran, C. T.; Scozzafava, A.; Jurca, B. C.; Hies, M. A. Carbonic anhydrase inhibitors. Part 49. Synthesis of substituted ureido-and thioureido derivatives of aromatic/heterocyclic sulfonamides with increased affinities for isozyme I. Eur. J. Med. Chem. 1998, 33, 83-93.
    • (1998) Eur. J. Med. Chem. , vol.33 , pp. 83-93
    • Supuran, C.T.1    Scozzafava, A.2    Jurca, B.C.3    Hies, M.A.4
  • 30
    • 0015239422 scopus 로고
    • The carbon dioxide hydration activity of carbonic anhydrase
    • Khalifah, R. G. The carbon dioxide hydration activity of carbonic anhydrase. J. Biol. Chem. 1971, 246, 2561-2573.
    • (1971) J. Biol. Chem. , vol.246 , pp. 2561-2573
    • Khalifah, R.G.1
  • 31
    • 0027160108 scopus 로고
    • Determination of acetazolamide in dosage forms by high performance liquid chromatography
    • Gomaa, Z. S. Determination of acetazolamide in dosage forms by high performance liquid chromatography. Biomed. Chromatogr. 1993, 7, 134-135.
    • (1993) Biomed. Chromatogr. , vol.7 , pp. 134-135
    • Gomaa, Z.S.1
  • 32
    • 0017973594 scopus 로고
    • pH-induced difference spectrophotometric assay of acetazolamide, hydrochlorothiazide and furosemide
    • Abdine, H.; Elsayed, M. A.; Elsayed, Y. M. pH-induced difference spectrophotometric assay of acetazolamide, hydrochlorothiazide and furosemide. J. Assoc. Off. Anal. Chem. 1978, 61, 695-701.
    • (1978) J. Assoc. Off. Anal. Chem. , vol.61 , pp. 695-701
    • Abdine, H.1    Elsayed, M.A.2    Elsayed, Y.M.3
  • 33
    • 0002993953 scopus 로고
    • Design of carbonic anhydrase inhibitors and the relationship between the pharmacodymanics and pharmacokinetics of acetazolamide
    • Botrè, F., Gros, G., Storey, B. T., Eds.; VCH: Weinheim, Germany
    • Wistrand, P. J.; Lindqvist, A. Design of carbonic anhydrase inhibitors and the relationship between the pharmacodymanics and pharmacokinetics of acetazolamide. In Carbonic Anhydrase - From Biochemistry and Genetics to Physiology and Clinical Medicine; Botrè, F., Gros, G., Storey, B. T., Eds.; VCH: Weinheim, Germany, 1991; pp 352-378.
    • (1991) Carbonic Anhydrase - From Biochemistry and Genetics to Physiology and Clinical Medicine , pp. 352-378
    • Wistrand, P.J.1    Lindqvist, A.2
  • 34
    • 0037463790 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Inhibition of the tumor-associated isozyme IX with aromatic and heterocyclic sulfonamides
    • Vullo, D.; Franchi, M.; Gallori, E.; Pastorek, J.; Scozzafava, A.; Pastorekova, S.; Supuran, C. T. Carbonic anhydrase inhibitors. Inhibition of the tumor-associated isozyme IX with aromatic and heterocyclic sulfonamides. Bioorg. Med. Chem. Lett. 2003, 13, 1005-1009.
    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 1005-1009
    • Vullo, D.1    Franchi, M.2    Gallori, E.3    Pastorek, J.4    Scozzafava, A.5    Pastorekova, S.6    Supuran, C.T.7
  • 35
    • 0034719437 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Synthesis of membrane-impermeant low molecular weight sulfinamides possessing in vivo selectivity for the membrane-bound versus cytosolic isozymes
    • Scozzafava, A.; Briganti, F.; Hies, M.; Supuran, C. T. Carbonic anhydrase inhibitors: synthesis of membrane-impermeant low molecular weight sulfinamides 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    Hies, M.3    Supuran, C.T.4
  • 36
    • 0842281270 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: The first selective, membrane-impermeant inhibitors targeting the tumor-associated isozyme IX
    • Pastorekova, S.; Casini, A.; Scozzafava, A.; Vullo, D.; Pastorek, J.; Supuran, C. T. Carbonic anhydrase inhibitors: The first selective, membrane-impermeant inhibitors targeting the tumor-associated isozyme IX. Bioorg. Med. Chem. Lett. 2004, 14, 869-873.
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 869-873
    • Pastorekova, S.1    Casini, A.2    Scozzafava, A.3    Vullo, D.4    Pastorek, J.5    Supuran, C.T.6
  • 37
    • 0348147633 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: E7070, a sulfonamide anti-cancer agent, potently inhibits cytosolic isozymes I and II, and transmembrane, tumor-associated isozyme IX
    • (a) Abbate, F.; Casini, A.; Owa, T.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors: E7070, a sulfonamide anti-cancer agent, potently inhibits cytosolic isozymes I and II, and transmembrane, tumor-associated isozyme IX. Bioorg. Med. Chem. Lett. 2004, 14, 217-223.
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 217-223
    • Abbate, F.1    Casini, A.2    Owa, T.3    Scozzafava, A.4    Supuran, C.T.5
  • 38
    • 1642540579 scopus 로고    scopus 로고
    • Unexpected nanomolar inhibition of carbonic anhydrase by COX-2 selective celecoxib: New pharmacological opportunities due to related binding site recognition
    • (b) Weber, A.; Casini, A.; Heine, A.; Kuhn, D.; Supuran, C. T.; Scozzafava, A.; Klebe, G. Unexpected nanomolar inhibition of carbonic anhydrase by COX-2 selective celecoxib: New pharmacological opportunities due to related binding site recognition. J. Med. Chem. 2004, 47, 550-557.
    • (2004) J. Med. Chem. , vol.47 , pp. 550-557
    • Weber, A.1    Casini, A.2    Heine, A.3    Kuhn, D.4    Supuran, C.T.5    Scozzafava, A.6    Klebe, G.7
  • 39
    • 0043198517 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: X ray crystallographic structure of the adduct of human isozyme II with the perfluorobenzoyl analogue of methazolamide. Implications for the drug design of fluorinated inhibitors
    • (a) Abbate, F.; Casini, A.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors: X ray crystallographic structure of the adduct of human isozyme II with the perfluorobenzoyl analogue of methazolamide. Implications for the drug design of fluorinated inhibitors. J. Enzyme Inhib. Med. Chem. 2003, 18, 303-308.
    • (2003) J. Enzyme Inhib. Med. Chem. , vol.18 , pp. 303-308
    • Abbate, F.1    Casini, A.2    Scozzafava, A.3    Supuran, C.T.4
  • 40
    • 0038149006 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: X ray crystallographic structure of the adduct of human isozyme II with a bis-sulfonamide-two heads are better than one?
    • (b) Casini, A.; Abbate, F.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors: X ray crystallographic structure of the adduct of human isozyme II with a bis-sulfonamide-two heads are better than one? Bioorg. Med. Chem. Lett. 2003, 13, 2759-2763.
    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 2759-2763
    • Casini, A.1    Abbate, F.2    Scozzafava, A.3    Supuran, C.T.4
  • 41
    • 1842639484 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: X ray crystallographic structure of the adduct of human isozyme II with a topically acting antiglaucoma sulfonamide
    • (c) Abbate, F.; Casini, A.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors: X ray crystallographic structure of the adduct of human isozyme II with a topically acting antiglaucoma sulfonamide. Bioorg. Med. Chem. Lett. 2004, 14, 2357-2361.
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 2357-2361
    • Abbate, F.1    Casini, A.2    Scozzafava, A.3    Supuran, C.T.4
  • 42
    • 3442884580 scopus 로고    scopus 로고
    • Benzolamide is not a membrane-impermeant carbonic anhydrase inhibitor
    • Supuran, C. T.; Scozzafava, A. Benzolamide is not a membrane-impermeant carbonic anhydrase inhibitor. J. Enzyme Inhib. Med. Chem. 2004, 19, 269-273.
    • (2004) J. Enzyme Inhib. Med. Chem. , vol.19 , pp. 269-273
    • Supuran, C.T.1    Scozzafava, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.