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Volumn 51, Issue 24, 2008, Pages 7968-7979

Dual inhibitors of matrix metalloproteinases and carbonic anhydrases: Iminodiacetyl-based hydroxamate-benzenesulfonamide conjugates

Author keywords

[No Author keywords available]

Indexed keywords

ACETAZOLAMIDE; BENZENESULFONAMIDE DERIVATIVE; BICARBONATE; CARBON DIOXIDE; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE INHIBITOR; CGS 27023A; DIGLYCINE; HYDROXAMATE BENZENESULFONAMIDE CONJUGATE; HYDROXAMIC ACID; MATRIX METALLOPROTEINASE; MATRIX METALLOPROTEINASE INHIBITOR; N (4 SULFAMOYLPHENYLETHYL) 4 SULFAMOYLBENZAMIDE; UNCLASSIFIED DRUG;

EID: 58149086406     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm800964f     Document Type: Article
Times cited : (53)

References (53)
  • 1
    • 0035188727 scopus 로고    scopus 로고
    • How matrix metalloproteinases regulate cell behavior
    • Sternlicht, M. D.; Werb, Z. How matrix metalloproteinases regulate cell behavior. Annu. Rev. Cell Dev. Biol. 2001, 17, 463-516.
    • (2001) Annu. Rev. Cell Dev. Biol , vol.17 , pp. 463-516
    • Sternlicht, M.D.1    Werb, Z.2
  • 2
    • 0036512208 scopus 로고    scopus 로고
    • New functions for the matrix metalloproteinases in cancer progression
    • Egeblad, M.; Werb, Z. New functions for the matrix metalloproteinases in cancer progression. Nat. Rev. Cancer 2002, 2, 161-174.
    • (2002) Nat. Rev. Cancer , vol.2 , pp. 161-174
    • Egeblad, M.1    Werb, Z.2
  • 3
    • 3543134126 scopus 로고    scopus 로고
    • Matrix metalloproteinases as modulators of inflammation and innate immunity
    • Parks, W. C.; Wilson, C. L.; López-Boado, Y. S. Matrix metalloproteinases as modulators of inflammation and innate immunity. Nat. Rev. Immunol. 2004, 4, 617-629.
    • (2004) Nat. Rev. Immunol , vol.4 , pp. 617-629
    • Parks, W.C.1    Wilson, C.L.2    López-Boado, Y.S.3
  • 4
    • 34248156625 scopus 로고    scopus 로고
    • Matrix metalloproteases: Underutilized targets for drug delivery
    • Vartak, D. G.; Gemeinhart, R. A. Matrix metalloproteases: underutilized targets for drug delivery. J. Drug Target. 2007, 15, 1-20.
    • (2007) J. Drug Target , vol.15 , pp. 1-20
    • Vartak, D.G.1    Gemeinhart, R.A.2
  • 5
    • 37349082926 scopus 로고    scopus 로고
    • Matrix metalloproteinases and their inhibitors in vascular remodeling and vascular disease. A
    • Raffetto, J. D.; Khalil, R. Matrix metalloproteinases and their inhibitors in vascular remodeling and vascular disease. A. Biochem. Pharmacol. 2008, 75, 346-359.
    • (2008) Biochem. Pharmacol , vol.75 , pp. 346-359
    • Raffetto, J.D.1    Khalil, R.2
  • 6
    • 0036716282 scopus 로고    scopus 로고
    • Strategies for MMP inhibition in cancer: Innovations for the post-trial era
    • Overall, C. M.; López-Otín, C. Strategies for MMP inhibition in cancer: innovations for the post-trial era. Nat. Rev. Cancer 2002, 2, 657-672.
    • (2002) Nat. Rev. Cancer , vol.2 , pp. 657-672
    • Overall, C.M.1    López-Otín, C.2
  • 7
    • 36148994693 scopus 로고    scopus 로고
    • The other side of MMPs: Protective roles in tumor progression
    • Martin, M. D.; Matrisian, L. M. The other side of MMPs: protective roles in tumor progression. Cancer Metastasis Rev. 2007, 26, 717-724.
    • (2007) Cancer Metastasis Rev , vol.26 , pp. 717-724
    • Martin, M.D.1    Matrisian, L.M.2
  • 8
    • 0037192458 scopus 로고    scopus 로고
    • Matrix metalloproteinase inhibitors and cancer: Trials and tribulations
    • Coussens, L. M.; Fingleton, B.; Matrisian, L. M. Matrix metalloproteinase inhibitors and cancer: trials and tribulations. Science 2002, 295, 2387-2392.
    • (2002) Science , vol.295 , pp. 2387-2392
    • Coussens, L.M.1    Fingleton, B.2    Matrisian, L.M.3
  • 9
    • 33644545381 scopus 로고    scopus 로고
    • Tumour microenvironment - Opinion: Validating matrix metalloproteinases as drug targets and anti-targets for cancer therapy
    • Overall, C. M.; Kleifeld, O. Tumour microenvironment - Opinion: validating matrix metalloproteinases as drug targets and anti-targets for cancer therapy. Nat. Rev. Cancer 2006, 6, 227-239.
    • (2006) Nat. Rev. Cancer , vol.6 , pp. 227-239
    • Overall, C.M.1    Kleifeld, O.2
  • 10
    • 33645738383 scopus 로고    scopus 로고
    • Towards third generation matrix metalloproteinase inhibitors for cancer therapy
    • Overall, C. M.; Kleifeld, O. Towards third generation matrix metalloproteinase inhibitors for cancer therapy. Br. J. Cancer 2006, 94, 941-946.
    • (2006) Br. J. Cancer , vol.94 , pp. 941-946
    • Overall, C.M.1    Kleifeld, O.2
  • 12
    • 36849073658 scopus 로고    scopus 로고
    • MMPs as therapeutic targets - Still a viable option
    • Fingleton, B. MMPs as therapeutic targets - Still a viable option. Semin. Cell Dev. Biol. 2008, 19, 61-68.
    • (2008) Semin. Cell Dev. Biol , vol.19 , pp. 61-68
    • Fingleton, B.1
  • 13
    • 2442579987 scopus 로고    scopus 로고
    • Carbonic anhydrases: Catalytic and inhibition mechanisms, distribution and physiological roles
    • Supuran, C. T, Scozzafava, A, Conway, J, Eds. CRC Press: Boca Raton, London, and New York
    • Supuran, C. T. Carbonic anhydrases: catalytic and inhibition mechanisms, distribution and physiological roles. In Carbonic Anhydrase. Its Inhibitors and Activators; Supuran, C. T.; Scozzafava, A.; Conway, J., Eds. CRC Press: Boca Raton, London, and New York, 2004; pp 1-23.
    • (2004) Carbonic Anhydrase. Its Inhibitors and Activators , pp. 1-23
    • Supuran, C.T.1
  • 14
    • 0014135426 scopus 로고
    • Carbonic anhydrase: Chemistry, physiology, and inhibition
    • Maren, T. H. Carbonic anhydrase: chemistry, physiology, and inhibition. Physiol. Rev. 1967, 47, 595-781.
    • (1967) Physiol. Rev , vol.47 , pp. 595-781
    • Maren, T.H.1
  • 16
    • 33845896020 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors and activators and their use in therapy
    • Scozzafava, A.; Mastrolorenzo, A.; Supuran, C. T. Carbonic anhydrase inhibitors and activators and their use in therapy. Expert Opin. Ther. Pat. 2006, 16, 1627-1664.
    • (2006) Expert Opin. Ther. Pat , vol.16 , pp. 1627-1664
    • Scozzafava, A.1    Mastrolorenzo, A.2    Supuran, C.T.3
  • 17
    • 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
  • 18
    • 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
  • 19
    • 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.; Simone, G. D.; 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    Simone, G.D.7    Supuran, C.T.8
  • 21
    • 0035833062 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: 4-sulfamoyl-benzenecarboxamides and 4-chloro-3-sulfamoyl-benzenecarboxamides with strong topical antiglaucoma properties
    • Mincione, F.; Starnotti, M.; Menabuoni, L.; Scozzafava, A.; Casini, A.; Supuran, C. T. Carbonic anhydrase inhibitors: 4-sulfamoyl-benzenecarboxamides and 4-chloro-3-sulfamoyl-benzenecarboxamides with strong topical antiglaucoma properties. Bioorg. Med. Chem. Lett. 2001, 11, 1787-1791.
    • (2001) Bioorg. Med. Chem. Lett , vol.11 , pp. 1787-1791
    • Mincione, F.1    Starnotti, M.2    Menabuoni, L.3    Scozzafava, A.4    Casini, A.5    Supuran, C.T.6
  • 22
    • 0034609778 scopus 로고    scopus 로고
    • Scozzafava, A.; Supuran, C. T. Carbonic anhydrase and matrix metalloproteinase inhibitors: sulfonylated amino acid hydroxamates with MMP inhibitory properties act as efficient inhibitors of CA isozymes I, II, and IV, and N-hydroxysulfonamides inhibit both these zinc enzymes. J. Med. Chem. 2000, 43, 3677-3687.
    • Scozzafava, A.; Supuran, C. T. Carbonic anhydrase and matrix metalloproteinase inhibitors: sulfonylated amino acid hydroxamates with MMP inhibitory properties act as efficient inhibitors of CA isozymes I, II, and IV, and N-hydroxysulfonamides inhibit both these zinc enzymes. J. Med. Chem. 2000, 43, 3677-3687.
  • 23
    • 33847003058 scopus 로고    scopus 로고
    • Carbonic anhydrase and matrix metalloproteinase inhibitors. Inhibition of human tumor-associated isozymes IX and cytosolic isozyme I and II with sulfonylated hydroxamates
    • Nuti, E.; Orlandini, E.; Nencetti, S.; Rossello, A.; Innocenti, A.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase and matrix metalloproteinase inhibitors. Inhibition of human tumor-associated isozymes IX and cytosolic isozyme I and II with sulfonylated hydroxamates. Bioorg. Med. Chem. 2007, 15, 2298-2311.
    • (2007) Bioorg. Med. Chem , vol.15 , pp. 2298-2311
    • Nuti, E.1    Orlandini, E.2    Nencetti, S.3    Rossello, A.4    Innocenti, A.5    Scozzafava, A.6    Supuran, C.T.7
  • 25
    • 33745778881 scopus 로고    scopus 로고
    • N-hydroxyurea - a versatile zinc binding function in the design of metalloenzyme inhibitors
    • Temperini, C.; Innocenti, A.; Scozzafava, A.; Supuran, C. T. N-hydroxyurea - a versatile zinc binding function in the design of metalloenzyme inhibitors. Bioorg. Med. Chem. Lett. 2006, 16, 4316-4320.
    • (2006) Bioorg. Med. Chem. Lett , vol.16 , pp. 4316-4320
    • Temperini, C.1    Innocenti, A.2    Scozzafava, A.3    Supuran, C.T.4
  • 26
    • 0037320183 scopus 로고    scopus 로고
    • A comparative QSAR study on carbonic anhydrase and matrix metalloproteinase inhibition by sulfonylated amino acid hydroxamates
    • Gupta, S. P.; Maheswaran, V.; Pande, V.; Kumar, D. A comparative QSAR study on carbonic anhydrase and matrix metalloproteinase inhibition by sulfonylated amino acid hydroxamates. J. Enzyme Inhib. Med. Chem. 2003, 18, 7-13.
    • (2003) J. Enzyme Inhib. Med. Chem , vol.18 , pp. 7-13
    • Gupta, S.P.1    Maheswaran, V.2    Pande, V.3    Kumar, D.4
  • 27
    • 33749265325 scopus 로고    scopus 로고
    • Design, synthesis and molecular modeling studies of iminodiacetyl monohydroxamic acid derivatives as MMP inhibitors
    • Santos, M. A.; Marques, S. M.; Tuccinardi, T.; Carelli, P.; Panelli, L.; Rossello, A. Design, synthesis and molecular modeling studies of iminodiacetyl monohydroxamic acid derivatives as MMP inhibitors. Bioorg. Med. Chem. 2006, 14, 7539-7550.
    • (2006) Bioorg. Med. Chem , vol.14 , pp. 7539-7550
    • Santos, M.A.1    Marques, S.M.2    Tuccinardi, T.3    Carelli, P.4    Panelli, L.5    Rossello, A.6
  • 28
    • 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
  • 29
  • 30
    • 0033957834 scopus 로고    scopus 로고
    • The SWISS-PROT protein sequence database and its supplement TrEMBL in 2000
    • Bairoch, A.; Apweiler, R. The SWISS-PROT protein sequence database and its supplement TrEMBL in 2000. Nucleic Acids Res. 2000, 28, 45-48.
    • (2000) Nucleic Acids Res , vol.28 , pp. 45-48
    • Bairoch, A.1    Apweiler, R.2
  • 31
    • 0037293521 scopus 로고    scopus 로고
    • Yoshiizumi, K.; Yamamoto, M.; Miyasaka, T.; Ito, Y.; Kumihara, H.; Sawa, M.; Kiyoi, T.; Yamamoto, T.; Nakajima, F.; Hirayama, R.; Kondo, H.; Ishibushi, E.; Ohmoto, H.; Inoue, Y.; Yoshino, K. Synthesis and structure-activity relationships of 5,6,7,8-tetrahydropyrido(3,4-b)pyrazine-based hydroxamic acids as HB-EGF shedding inhibitors. Bioorg. Med. Chem. 2003, 11, 433-450.
    • Yoshiizumi, K.; Yamamoto, M.; Miyasaka, T.; Ito, Y.; Kumihara, H.; Sawa, M.; Kiyoi, T.; Yamamoto, T.; Nakajima, F.; Hirayama, R.; Kondo, H.; Ishibushi, E.; Ohmoto, H.; Inoue, Y.; Yoshino, K. Synthesis and structure-activity relationships of 5,6,7,8-tetrahydropyrido(3,4-b)pyrazine-based hydroxamic acids as HB-EGF shedding inhibitors. Bioorg. Med. Chem. 2003, 11, 433-450.
  • 32
    • 33646175469 scopus 로고    scopus 로고
    • Amber force field implementation, molecular modelling study, synthesis and MMP-1/MMP-2 inhibition profile of (R)- and (S)-N-hydroxy-2-(N-isopropoxybiphenyl-4-ylsulfonamido)-3-methylbutanamides
    • Tuccinardi, T.; Martinelli, A.; Nuti, E.; Carelli, P.; Balsano, F.; Uccello-Barretta, G.; Murphy, G.; Rossello, A. Amber force field implementation, molecular modelling study, synthesis and MMP-1/MMP-2 inhibition profile of (R)- and (S)-N-hydroxy-2-(N-isopropoxybiphenyl-4-ylsulfonamido)-3-methylbutanamides. Bioorg. Med. Chem. 2006, 14, 4260-4276.
    • (2006) Bioorg. Med. Chem , vol.14 , pp. 4260-4276
    • Tuccinardi, T.1    Martinelli, A.2    Nuti, E.3    Carelli, P.4    Balsano, F.5    Uccello-Barretta, G.6    Murphy, G.7    Rossello, A.8
  • 33
    • 0032970753 scopus 로고    scopus 로고
    • Gas chromatographic-mass spectrometric analysis of hydroxylamine for monitoring the metabolic hydrolysis of metalloprotease inhibitors in rat and human liver microsomes
    • Peng, S. X.; Strojnowski, M. J.; Joanna K, Hu, B. J. S.; Eichhold, T. H.; Wehmeyer, K. R.; Pikul, S.; Almstead, N. G. Gas chromatographic-mass spectrometric analysis of hydroxylamine for monitoring the metabolic hydrolysis of metalloprotease inhibitors in rat and human liver microsomes. J. Chromatogr. B 1999, 724, 181-187.
    • (1999) J. Chromatogr. B , vol.724 , pp. 181-187
    • Peng, S.X.1    Strojnowski, M.J.2    Joanna, K.3    Hu, B.J.S.4    Eichhold, T.H.5    Wehmeyer, K.R.6    Pikul, S.7    Almstead, N.G.8
  • 34
    • 0037142342 scopus 로고    scopus 로고
    • Structural differences of matrix metalloproteinases with potential implications for inhibitor selectivity examined by the GRID/CPCA approach
    • Terp, G. E.; Cruciani, G.; Christensen, I. T.; Jørgensen, F. S. Structural differences of matrix metalloproteinases with potential implications for inhibitor selectivity examined by the GRID/CPCA approach. J. Med. Chem. 2002, 45, 2675-2684.
    • (2002) J. Med. Chem , vol.45 , pp. 2675-2684
    • Terp, G.E.1    Cruciani, G.2    Christensen, I.T.3    Jørgensen, F.S.4
  • 35
    • 12444254805 scopus 로고    scopus 로고
    • Levin, J. I.; Chen, J. M.; Cheung, K.; Cole, D.; Crago, C.; Santos, E. D.; Du, X.; Khafizova, G.; MacEwan, G.; Niu, C.; Salaski, E. J.; Zask, A.; Cummons, T.; Sung, A.; J. Xu, Y. Z.; Xu, W.; Ayral-Kaloustian, S.; Jin, G.; Cowling, R.; Barone, D.; Mohler, K. M.; Black, R. A.; Skotnicki, J. S. Acetylenic TACE inhibitors. Part 1. SAR of the acyclic sulfonamide hydroxamates. Bioorg. Med. Chem. Lett. 2003, 13, 2799-2803.
    • Levin, J. I.; Chen, J. M.; Cheung, K.; Cole, D.; Crago, C.; Santos, E. D.; Du, X.; Khafizova, G.; MacEwan, G.; Niu, C.; Salaski, E. J.; Zask, A.; Cummons, T.; Sung, A.; J. Xu, Y. Z.; Xu, W.; Ayral-Kaloustian, S.; Jin, G.; Cowling, R.; Barone, D.; Mohler, K. M.; Black, R. A.; Skotnicki, J. S. Acetylenic TACE inhibitors. Part 1. SAR of the acyclic sulfonamide hydroxamates. Bioorg. Med. Chem. Lett. 2003, 13, 2799-2803.
  • 37
    • 33847161733 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Inhibition of cytosolic/ tumor-associated isoforms I, II and IX with iminodiacetic carboxylates/ hydroxamates also incorporating benzenesulfonamide moieties
    • Santos, M. A.; Marques, S.; Vullo, D.; Innocenti, A.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors. Inhibition of cytosolic/ tumor-associated isoforms I, II and IX with iminodiacetic carboxylates/ hydroxamates also incorporating benzenesulfonamide moieties. Bioorg. Med. Chem. Lett. 2007, 17, 1538-1543.
    • (2007) Bioorg. Med. Chem. Lett , vol.17 , pp. 1538-1543
    • Santos, M.A.1    Marques, S.2    Vullo, D.3    Innocenti, A.4    Scozzafava, A.5    Supuran, C.T.6
  • 38
    • 0031552362 scopus 로고    scopus 로고
    • Development and validation of a genetic algorithm for flexible docking
    • Jones, G.; Willett, P.; Glen, R. C.; Leach, A. R.; Taylor, R. Development and validation of a genetic algorithm for flexible docking. J. Mol. Biol. 1997, 267, 727-748.
    • (1997) J. Mol. Biol , vol.267 , pp. 727-748
    • Jones, G.1    Willett, P.2    Glen, R.C.3    Leach, A.R.4    Taylor, R.5
  • 40
    • 49149123555 scopus 로고    scopus 로고
    • Development of a receptor-based 3D-QSAR study for the analysis of MMP2, MMP3, and MMP9 inhibitors
    • Tuccinardi, T.; Nuti, E.; Ortore, G.; Rossello, A.; Avramova, S. I.; Martinelli, A. Development of a receptor-based 3D-QSAR study for the analysis of MMP2, MMP3, and MMP9 inhibitors. Bioorg. Med. Chem. 2008, 16, 7749-7758.
    • (2008) Bioorg. Med. Chem , vol.16 , pp. 7749-7758
    • Tuccinardi, T.1    Nuti, E.2    Ortore, G.3    Rossello, A.4    Avramova, S.I.5    Martinelli, A.6
  • 42
    • 0026505650 scopus 로고
    • A novel coumarin-labelled peptide for sensitive continuous assays of the matrix metalloproteinases
    • Knight, C. G.; Willenbrock, F.; Murphy, G. A novel coumarin-labelled peptide for sensitive continuous assays of the matrix metalloproteinases. FEBS Lett. 1992, 296, 263-266.
    • (1992) FEBS Lett , vol.296 , pp. 263-266
    • Knight, C.G.1    Willenbrock, F.2    Murphy, G.3
  • 43
  • 44
    • 2142828483 scopus 로고    scopus 로고
    • 2, a fluorogenic substrate with increased specificity constants for collagenases and tumor necrosis factor converting enzyme
    • 2, a fluorogenic substrate with increased specificity constants for collagenases and tumor necrosis factor converting enzyme. Anal. Biochem. 2004, 328, 166-173.
    • (2004) Anal. Biochem , vol.328 , pp. 166-173
    • Neumann, U.1    Kubota, H.2    Frei, K.3    Ganu, V.4    Leppert, D.5
  • 45
    • 58149091292 scopus 로고    scopus 로고
    • 4.7.1 by Molecular Device
    • SoftMax Pro 4.7.1 by Molecular Device.
    • Pro, S.1
  • 46
    • 58149088969 scopus 로고    scopus 로고
    • GraFit version 4 by Erithecus Software.
    • GraFit version 4 by Erithecus Software.
  • 47
    • 22744446294 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Design of fluorescent sulfonamides as probes of tumor-associated carbonic anhydrase IX that inhibit isozyme IX-mediated acidification of hypoxic tumors
    • (a) Cecchi, A.; Hulikova, A.; Pastorek, J.; Pastorekova, S.; Scozzafava, A.; Winum, J.-Y.; Montero, J.-L.; Supuran, C. T. Carbonic anhydrase inhibitors. Design of fluorescent sulfonamides as probes of tumor-associated carbonic anhydrase IX that inhibit isozyme IX-mediated acidification of hypoxic tumors. J. Med. Chem. 2005, 48, 4834-4841.
    • (2005) J. Med. Chem , vol.48 , pp. 4834-4841
    • Cecchi, A.1    Hulikova, A.2    Pastorek, J.3    Pastorekova, S.4    Scozzafava, A.5    Winum, J.-Y.6    Montero, J.-L.7    Supuran, C.T.8
  • 48
    • 1842628633 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Design of selective, membrane-impermeant inhibitors targeting the human tumor-associated isozyme IX
    • (b) 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
  • 49
    • 0842281270 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: The first selective, membrane-impermeant inhibitors targeting the tumor-associated isozyme IX
    • (a) 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
  • 50
    • 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?
    • (b) 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
  • 51
    • 58149088670 scopus 로고    scopus 로고
    • Maestro, version 7.5; Schrödinger Inc, Portland, OR, 2005
    • Maestro, version 7.5; Schrödinger Inc.: Portland, OR, 2005.
  • 52
    • 58149086438 scopus 로고    scopus 로고
    • Macromodel, version 8.5; Schrödinger Inc, Portland, OR, 1999
    • Macromodel, version 8.5; Schrödinger Inc.: Portland, OR, 1999.


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