메뉴 건너뛰기




Volumn 51, Issue 11, 2008, Pages 3230-3237

Carbonic anhydrase inhibitors: Bioreductive nitro-containing sulfonamides with selectivity for targeting the tumor associated isoforms IX and XII

Author keywords

[No Author keywords available]

Indexed keywords

2 CHLORO 5 NITRO BENZENESULFONAMIDE; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE INHIBITOR; NITRO DERIVATIVE; SULFONAMIDE;

EID: 44949169465     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm800121c     Document Type: Article
Times cited : (48)

References (40)
  • 1
    • 38849143765 scopus 로고    scopus 로고
    • Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators
    • Supuran, C. T. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat. Rev. Drug Discovery 2008, 7, 168-181.
    • (2008) Nat. Rev. Drug Discovery , vol.7 , pp. 168-181
    • Supuran, C.T.1
  • 2
    • 34248659399 scopus 로고    scopus 로고
    • Carbonic anhydrases as targets for medicinal chemistry
    • Supuran, C. T.; Scozzafava, A. Carbonic anhydrases as targets for medicinal chemistry. Bioorg. Med. Chem. 2007, 15, 4336-4350.
    • (2007) Bioorg. Med. Chem , vol.15 , pp. 4336-4350
    • Supuran, C.T.1    Scozzafava, A.2
  • 3
    • 33750082400 scopus 로고    scopus 로고
    • Targeting tumor-associated carbonic anhydrase IX in cancer therapy
    • Thiry, A.; Dogné, J. M.; Masereel, B.; Supuran, C. T. Targeting tumor-associated carbonic anhydrase IX in cancer therapy. Trends Pharmacol. Sci. 2006, 27, 566-573.
    • (2006) Trends Pharmacol. Sci , vol.27 , pp. 566-573
    • Thiry, A.1    Dogné, J.M.2    Masereel, B.3    Supuran, C.T.4
  • 4
    • 34249670767 scopus 로고    scopus 로고
    • Carbonic Anhydrase Inhibitors and the Management of Cancer
    • Pastorekova, S.; Kopacek, J.; Pastorek, J. Carbonic Anhydrase Inhibitors and the Management of Cancer. Curr. Top. Med. Chem. 2007, 7, 865-878.
    • (2007) Curr. Top. Med. Chem , vol.7 , pp. 865-878
    • Pastorekova, S.1    Kopacek, J.2    Pastorek, J.3
  • 5
    • 33745644458 scopus 로고    scopus 로고
    • Carbonic Anhydrase Inhibitors: X-ray and Molecular Modeling Study for the Interaction of a Fluorescent Antitumor Sulfonamide with Isozyme II and IX
    • Alterio, V.; Vitale, R. M.; Monti, S. M.; Pedone, C.; Scozzafava, A.; Cecchi, A.; De Simone, G.; Supuran, C. T. Carbonic Anhydrase Inhibitors: X-ray and Molecular Modeling Study for the Interaction of a Fluorescent Antitumor Sulfonamide with Isozyme II and IX. J. Am. Chem. Soc. 2006, 128, 8329-8335.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 8329-8335
    • Alterio, V.1    Vitale, R.M.2    Monti, S.M.3    Pedone, C.4    Scozzafava, A.5    Cecchi, A.6    De Simone, G.7    Supuran, C.T.8
  • 6
    • 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
  • 7
    • 33748541296 scopus 로고    scopus 로고
    • Carbonic Anhydrase Inhibitors: Hypoxia-Activatable Sulfonamides Incorporating Disulfide Bonds that Target the Tumor-Associated Isoform IX
    • De Simone, G.; Vitale, R. M.; Di Fiore, A.; Pedone, C.; Scozzafava, A.; Montera, J. L.; Winum, J. Y.; Supuran, C. T. Carbonic Anhydrase Inhibitors: Hypoxia-Activatable Sulfonamides Incorporating Disulfide Bonds that Target the Tumor-Associated Isoform IX. J. Med. Chem. 2006, 49, 5544-5551.
    • (2006) J. Med. Chem , vol.49 , pp. 5544-5551
    • De Simone, G.1    Vitale, R.M.2    Di Fiore, A.3    Pedone, C.4    Scozzafava, A.5    Montera, J.L.6    Winum, J.Y.7    Supuran, C.T.8
  • 8
    • 0037963656 scopus 로고    scopus 로고
    • Nitroheterocyclic drugs with broad spectrum activity
    • Raether, W.; Hane, H. Nitroheterocyclic drugs with broad spectrum activity. Parasitol. Res. 2003, 90, S19-S39.
    • (2003) Parasitol. Res , vol.90
    • Raether, W.1    Hane, H.2
  • 9
    • 30744461618 scopus 로고    scopus 로고
    • Potentiation of the cytotoxicity of the anticancer agent tirapazamine by benzotriazine N-oxides: The role of redox equilibra
    • Anderson, R. F.; Shinde, S. S.; Hay, M. P.; Denny, W. A. Potentiation of the cytotoxicity of the anticancer agent tirapazamine by benzotriazine N-oxides: The role of redox equilibra. J. Am. Chem. Soc. 2006, 128, 245-249.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 245-249
    • Anderson, R.F.1    Shinde, S.S.2    Hay, M.P.3    Denny, W.A.4
  • 10
    • 33846850493 scopus 로고    scopus 로고
    • Dynamics of tumor hypoxia measured with bioreductive hypoxic cell markers
    • Ljungkvist, A. S.; Bussink, J.; Kaanders, J. H.; van der Kogel, A. J. Dynamics of tumor hypoxia measured with bioreductive hypoxic cell markers. Radiat. Res. 2007, 167, 127-145.
    • (2007) Radiat. Res , vol.167 , pp. 127-145
    • Ljungkvist, A.S.1    Bussink, J.2    Kaanders, J.H.3    van der Kogel, A.J.4
  • 11
    • 34249051656 scopus 로고    scopus 로고
    • In Vivo Molecular Imaging Biomarkers: Clinical Pharmacology's new "PET
    • Nutt, R.; Vento, L. J.; Ridinger, M. H. T. In Vivo Molecular Imaging Biomarkers: Clinical Pharmacology's new "PET". Clin. Pharmacol. Ther. 2007, 81, 792-795.
    • (2007) Clin. Pharmacol. Ther , vol.81 , pp. 792-795
    • Nutt, R.1    Vento, L.J.2    Ridinger, M.H.T.3
  • 12
    • 0029781891 scopus 로고    scopus 로고
    • Acute alcohol produces hypoxia directly in rat liver tissue in vivo: Role of Kupffer cells
    • Arteel, G. E.; Raleigh, J. A.; Bradford, B. U.; Thurman, R. G. Acute alcohol produces hypoxia directly in rat liver tissue in vivo: role of Kupffer cells. Am. J. Physiol. 1996, 271, G494-G500.
    • (1996) Am. J. Physiol , vol.271
    • Arteel, G.E.1    Raleigh, J.A.2    Bradford, B.U.3    Thurman, R.G.4
  • 14
    • 34548070853 scopus 로고    scopus 로고
    • Design, synthesis, and SAR study of a series of N-alkyl-N′-[2-(aryloxy)-5-nitrobenzenesulfonyl]ureas and -cyanoguanidine as selective antagonists of the TPalpha and TPbeta isoforms of the human thromboxane A2 receptor
    • Hanson, J.; Dogné, J. M.; Ghiotto, J.; Moray, A. L.; Kinsella, B. T.; Pirotte, B. Design, synthesis, and SAR study of a series of N-alkyl-N′-[2-(aryloxy)-5-nitrobenzenesulfonyl]ureas and -cyanoguanidine as selective antagonists of the TPalpha and TPbeta isoforms of the human thromboxane A2 receptor. J. Med. Chem. 2007, 50, 3928-3936.
    • (2007) J. Med. Chem , vol.50 , pp. 3928-3936
    • Hanson, J.1    Dogné, J.M.2    Ghiotto, J.3    Moray, A.L.4    Kinsella, B.T.5    Pirotte, B.6
  • 15
    • 0015239422 scopus 로고    scopus 로고
    • Khalifah, R. G. The carbon dioxide hydration activity of carbonic anhydrase I. Stop-flow kinetic studies on the native human isoenzymes B and C. J. Biol. Chem. 1971, 246, 2561-2573.
    • Khalifah, R. G. The carbon dioxide hydration activity of carbonic anhydrase I. Stop-flow kinetic studies on the native human isoenzymes B and C. J. Biol. Chem. 1971, 246, 2561-2573.
  • 16
    • 0344193512 scopus 로고    scopus 로고
    • Casini, A.; Antel, J.; Abbate, F.; Scozzafava, A.; David, S.; Waldeck, H.; Schäfer, S.; Supuran, C. T. Carbonic anhydrase inhibitors: SAR and X-ray crystallographic study for the interaction of sugar sulfamates/sulfamides with isozymes I, II, and IV. Bioorg. Med. Chem. Lett. 2003, 13, 841-845.
    • Casini, A.; Antel, J.; Abbate, F.; Scozzafava, A.; David, S.; Waldeck, H.; Schäfer, S.; Supuran, C. T. Carbonic anhydrase inhibitors: SAR and X-ray crystallographic study for the interaction of sugar sulfamates/sulfamides with isozymes I, II, and IV. Bioorg. Med. Chem. Lett. 2003, 13, 841-845.
  • 17
    • 33845353402 scopus 로고    scopus 로고
    • 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
    • Winum, J. Y.; Temperini, C.; El Cheikh, K.; Innocenti, A.; Vullo, D.; Ciattini, S.; Montera, J. L.; Scozzafava, A.; 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. J. Med. Chem. 2006, 49, 7024-7031.
    • (2006) J. Med. Chem , vol.49 , pp. 7024-7031
    • Winum, J.Y.1    Temperini, C.2    El Cheikh, K.3    Innocenti, A.4    Vullo, D.5    Ciattini, S.6    Montera, J.L.7    Scozzafava, A.8    Supuran, C.T.9
  • 18
    • 33947690287 scopus 로고    scopus 로고
    • Phosph(on)ate as a zinc-binding group in metalloenzyme inhibitors: X-ray crystal structure of the antiviral drug foscarnet complexed to human carbonic anhydrase I
    • Temperini, C.; Innocenti, A.; Guerri, A.; Scozzafava, A.; Rusconi, S.; Supuran, C. T. Phosph(on)ate as a zinc-binding group in metalloenzyme inhibitors: X-ray crystal structure of the antiviral drug foscarnet complexed to human carbonic anhydrase I. Bioorg. Med. Chem. Lett. 2007, 17, 2210-2215.
    • (2007) Bioorg. Med. Chem. Lett , vol.17 , pp. 2210-2215
    • Temperini, C.1    Innocenti, A.2    Guerri, A.3    Scozzafava, A.4    Rusconi, S.5    Supuran, C.T.6
  • 19
    • 34347380126 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Inhibition of human, bacterial, and archaeal isozymes with benzene-1,3-disulfonamides: solution and crystallographic studies
    • AIterio, V.; De Simone, G.; Monti, S. M.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors: inhibition of human, bacterial, and archaeal isozymes with benzene-1,3-disulfonamides: solution and crystallographic studies. Bioorg. Med. Chem. Lett. 2007, 17, 4201-4207.
    • (2007) Bioorg. Med. Chem. Lett , vol.17 , pp. 4201-4207
    • AIterio, V.1    De Simone, G.2    Monti, S.M.3    Scozzafava, A.4    Supuran, C.T.5
  • 20
    • 37549037851 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Interaction of 2-(hydrazinocarbonyl)-3-phenyl-1H-indole-5-sulfonamide with 12 mammalian isoforms: Kinetic and X-ray crystallographic studies
    • Güzel, Ö.; Temperini, C.; Innocenti, A.; Scozzafava, A.; Salman, A.; Supuran, C. T. Carbonic anhydrase inhibitors. Interaction of 2-(hydrazinocarbonyl)-3-phenyl-1H-indole-5-sulfonamide with 12 mammalian isoforms: kinetic and X-ray crystallographic studies. Bioorg. Med. Chem. Lett. 2008, 18, 152-158.
    • (2008) Bioorg. Med. Chem. Lett , vol.18 , pp. 152-158
    • Güzel, O.1    Temperini, C.2    Innocenti, A.3    Scozzafava, A.4    Salman, A.5    Supuran, C.T.6
  • 21
    • 27944498514 scopus 로고    scopus 로고
    • 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
    • Di Fiore, A.; Pedone, C.; D'Ambrosio, K.; Scozzafava, A.; De Simone, G.; Supuran, C. T. 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. Bioorg. Med. Chem. Lett. 2006, 16, 437-442.
    • (2006) Bioorg. Med. Chem. Lett , vol.16 , pp. 437-442
    • Di Fiore, A.1    Pedone, C.2    D'Ambrosio, K.3    Scozzafava, A.4    De Simone, G.5    Supuran, C.T.6
  • 22
    • 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
    • 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
  • 23
    • 16244377468 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides: A new target for the design of antitumor and antiglaucoma drugs
    • Vullo, D.; Innocenti, A.; Nishimori, I.; Pastorek, J.; Scozzafava, A.; Pastorekova, S.; Supuran, C. T. Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides: a new target for the design of antitumor and antiglaucoma drugs. Bioorg. Med. Chem. Lett. 2005, 15, 963-969.
    • (2005) Bioorg. Med. Chem. Lett , vol.15 , pp. 963-969
    • Vullo, D.1    Innocenti, A.2    Nishimori, I.3    Pastorek, J.4    Scozzafava, A.5    Pastorekova, S.6    Supuran, C.T.7
  • 24
    • 0024218271 scopus 로고
    • Refined structure of human carbonic anhydrase II at 2.0 Å resolution
    • Eriksson, A. E.; Jones, T. A.; Liljas, A. Refined structure of human carbonic anhydrase II at 2.0 Å resolution. Proteins: Struct., Funct. 1988, 4, 274-282.
    • (1988) Proteins: Struct., Funct , vol.4 , pp. 274-282
    • Eriksson, A.E.1    Jones, T.A.2    Liljas, A.3
  • 25
    • 0031059866 scopus 로고    scopus 로고
    • Processing of X-ray Diffraction Data Collected in Oscillation Mode
    • Otwinowski, Z.; Minor, W. Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 1997, 276, 307-326.
    • (1997) Methods Enzymol , vol.276 , pp. 307-326
    • Otwinowski, Z.1    Minor, W.2
  • 27
    • 84889120137 scopus 로고
    • Improved methods for building protein models in electron density maps and the location of errors in these models
    • Jones, T. A.; Zou, J. Y.; Cowan, S. W.; Kjeldgaard, M. Improved methods for building protein models in electron density maps and the location of errors in these models. Acta Crystallogr., Sect. A: Found. Crystallogr. 1991, 47, 110-119.
    • (1991) Acta Crystallogr., Sect. A: Found. Crystallogr , vol.47 , pp. 110-119
    • Jones, T.A.1    Zou, J.Y.2    Cowan, S.W.3    Kjeldgaard, M.4
  • 28
    • 0000243829 scopus 로고
    • PROCHECK: A program to check the stereochemical quality of protein structures
    • Laskowski, R. A.; MacArthur, M. W.; Moss, D. S.; Thornton, J. M. 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    MacArthur, M.W.2    Moss, D.S.3    Thornton, J.M.4
  • 30
    • 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
  • 31
    • 0027136282 scopus 로고
    • Comparative protein modelling by satisfaction of spatial restraints
    • Sali, A.; Blundell, T. L. Comparative protein modelling by satisfaction of spatial restraints. J. Mol. Biol. 1993, 234, 779-815.
    • (1993) J. Mol. Biol , vol.234 , pp. 779-815
    • Sali, A.1    Blundell, T.L.2
  • 32
    • 0025830469 scopus 로고
    • A method to identify protein sequences that fold into a known three-dimensional structure
    • Bowie, J. U.; Luthy, R.; Eisenberg, D. A method to identify protein sequences that fold into a known three-dimensional structure. Science 1991, 253, 164-170.
    • (1991) Science , vol.253 , pp. 164-170
    • Bowie, J.U.1    Luthy, R.2    Eisenberg, D.3
  • 34
    • 0001398008 scopus 로고    scopus 로고
    • How Well Does a RESP (Restrained Electrostatic Potential) Model Do in Calculating the Conformational Energies of Organic and Biological Molecules?
    • Wang, J.; Cieplak, P.; Kollman, P. A. How Well Does a RESP (Restrained Electrostatic Potential) Model Do in Calculating the Conformational Energies of Organic and Biological Molecules? J. Comput. Chem. 2000, 21, 1049-1074.
    • (2000) J. Comput. Chem , vol.21 , pp. 1049-1074
    • Wang, J.1    Cieplak, P.2    Kollman, P.A.3
  • 35
    • 3042524904 scopus 로고    scopus 로고
    • Bayly, C. I.; Cieplak, P.; Cornell, W.; Kollman, P. A. A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges: the RESP model. J. Phys. Chem. 1993, 97, 10269-10280.
    • Bayly, C. I.; Cieplak, P.; Cornell, W.; Kollman, P. A. A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges: the RESP model. J. Phys. Chem. 1993, 97, 10269-10280.
  • 37
    • 0034829463 scopus 로고    scopus 로고
    • Molecular Dynamics Simulations of the Mononuclear Zinc-β-lactamase from Bacillus cereus
    • Suarez, D.; Merz, K. M. Molecular Dynamics Simulations of the Mononuclear Zinc-β-lactamase from Bacillus cereus. J. Am. Chem. Soc. 2001, 123, 3759-3770.
    • (2001) J. Am. Chem. Soc , vol.123 , pp. 3759-3770
    • Suarez, D.1    Merz, K.M.2
  • 38
    • 0001067597 scopus 로고
    • Force field design for metalloproteins
    • Hoops, S. C.; Anderson, K. W.; Merz, K. M. Force field design for metalloproteins. J. Am. Chem. Soc. 1991, 113, 8262-8270.
    • (1991) J. Am. Chem. Soc , vol.113 , pp. 8262-8270
    • Hoops, S.C.1    Anderson, K.W.2    Merz, K.M.3
  • 39
    • 33646940952 scopus 로고
    • Numerical integration of the cartesian equations of motion of a system with constraints: Molecular dynamics of n-alkanes
    • Ryckaert, J.-P.; Ciccotti, G.; Berendsen, H. J. C. Numerical integration of the cartesian equations of motion of a system with constraints: molecular dynamics of n-alkanes. J. Comput. Phys. 1977, 23, 327-341.
    • (1977) J. Comput. Phys , vol.23 , pp. 327-341
    • Ryckaert, J.-P.1    Ciccotti, G.2    Berendsen, H.J.C.3
  • 40
    • 0029881007 scopus 로고    scopus 로고
    • MOLMOL: A program for display and analysis of macromolecular structures
    • Koradi, R.; Billeter, M.; Wuthrich, K. MOLMOL: a program for display and analysis of macromolecular structures. J. Mol. Graphics 1996, 14, 51-55.
    • (1996) J. Mol. Graphics , vol.14 , pp. 51-55
    • Koradi, R.1    Billeter, M.2    Wuthrich, K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.