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Volumn 43, Issue 2, 2003, Pages 699-706

A structure-activity study of Taxol, taxotere, and derivatives using the electronic indices methodology (EIM)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRONIC INDICES METHODOLOGY (EIM); HIERARCHICAL CLUSTERING ANALYSIS (HCA);

EID: 0037365310     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci025640v     Document Type: Conference Paper
Times cited : (18)

References (54)
  • 3
    • 0004211829 scopus 로고
    • Oxford University Press: New York
    • Cancer Biology; Ruddon, R. W., Ed.; Oxford University Press: New York, 1987.
    • (1987) Cancer Biology
    • Ruddon, R.W.1
  • 4
    • 0026457950 scopus 로고
    • Multistep carcinogenesis: A 1992 perspective
    • Sugimura, T. Multistep carcinogenesis: A 1992 perspective. Science 1992, 258, 603-607.
    • (1992) Science , vol.258 , pp. 603-607
    • Sugimura, T.1
  • 5
    • 0345530219 scopus 로고    scopus 로고
    • EIU Marketing in Europe. Trade Reviews, 337, December 1990
    • EIU Marketing in Europe. Trade Reviews, 337, December 1990.
  • 6
    • 0001843250 scopus 로고
    • Taxane anticancer agents
    • American Chemical Society: Washington, DC
    • Taxane Anticancer Agents. Georg, G. I., Chen, T. T., Ojima, I., Vyas, D. M., Eds.: ACS Symposium Series 583; American Chemical Society: Washington, DC, 1995.
    • (1995) ACS Symposium Series , vol.583
    • Georg, G.I.1    Chen, T.T.2    Ojima, I.3    Vyas, D.M.4
  • 7
    • 0015211527 scopus 로고
    • Plant antitumor agents .6. Isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus-Brevifolia
    • Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. Plant antitumor agents .6. Isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus-Brevifolia. J. Am. Chem. Soc. 1971, 93, 2325-2327.
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 2325-2327
    • Wani, M.C.1    Taylor, H.L.2    Wall, M.E.3    Coggon, P.4    McPhail, A.T.5
  • 8
    • 0000052734 scopus 로고
    • Taxol and taxotere - Discovery, chemistry, and structure-activity-relationships
    • Guénard, D.; Guéritte-Voegelein, F.; Potier, P. Taxol and Taxotere - Discovery, chemistry, and structure-activity-relationships. Acc. Chem. Res. 1993, 20, 160-167.
    • (1993) Acc. Chem. Res. , vol.20 , pp. 160-167
    • Guénard, D.1    Guéritte-Voegelein, F.2    Potier, P.3
  • 9
    • 0000993536 scopus 로고
    • Taxane Anticancer Agents; Georg, G. I., Chen, T. T., Ojima, I., Vyas, D. M., Eds.: American Chemical Society: Washington, DC, Chapter 17
    • Commerčon, A.; Bouzart, J. D.; Didier, E.; Lavelle, F. In Taxane Anticancer Agents; Georg, G. I., Chen, T. T., Ojima, I., Vyas, D. M., Eds.: ACS Symposium Series 583; American Chemical Society: Washington, DC, 1995; Chapter 17, pp 233-246.
    • (1995) ACS Symposium Series , vol.583 , pp. 233-246
    • Commerčon, A.1    Bouzart, J.D.2    Didier, E.3    Lavelle, F.4
  • 11
    • 0034678986 scopus 로고    scopus 로고
    • Epothilones and related structures -a new class of mocrotubules inhibitors with potent in vivo antitumor activity
    • Altmann, K.-H.; Wartmann, M.; O'Reilly, T. Epothilones and related structures -a new class of mocrotubules inhibitors with potent in vivo antitumor activity. Biochim. Biophys. Acta 2000, 1470, M79-M91.
    • (2000) Biochim. Biophys. Acta , vol.1470
    • Altmann, K.-H.1    Wartmann, M.2    O'Reilly, T.3
  • 14
    • 0030022754 scopus 로고    scopus 로고
    • The "hydrophobic collapse" conformations of paclitaxel (Taxol) has been observed in a nonaqueous environment: Crystal structure of 10-deacetyl-7-epitaxol
    • Gao, Q.; Parker, W. L. The "hydrophobic collapse" conformations of paclitaxel (Taxol) has been observed in a nonaqueous environment: crystal structure of 10-deacetyl-7-epitaxol. Tetrahedron 1996, 52, 2291-2300.
    • (1996) Tetrahedron , vol.52 , pp. 2291-2300
    • Gao, Q.1    Parker, W.L.2
  • 16
    • 0029968838 scopus 로고    scopus 로고
    • NMR and molecular modeling study of the conformations of taxol 2′-acetate in chloroform and aqueous dimethyl sulfoxide solutions
    • Williams, H.; Moyna, G.; Scott, A. I. NMR and molecular modeling study of the conformations of taxol 2′-acetate in chloroform and aqueous dimethyl sulfoxide solutions. J. Med. Chem. 1996, 39, 1555-1559.
    • (1996) J. Med. Chem. , vol.39 , pp. 1555-1559
    • Williams, H.1    Moyna, G.2    Scott, A.I.3
  • 17
    • 0026554985 scopus 로고
    • Characterization of taxol in methylene chloride by NMR spectroscopy
    • Falzone, C. J.; Benesi, A. J.; Lecomte, J. T. Characterization of taxol in methylene chloride by NMR spectroscopy. Tetrahedron Lett. 1992, 33, 1169-1172.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 1169-1172
    • Falzone, C.J.1    Benesi, A.J.2    Lecomte, J.T.3
  • 18
    • 0027305373 scopus 로고
    • NMR and molecular modeling study of the conformations of taxol and of its side chain methylester in aqueous and nonaqueous solution
    • William, H. J.; Scott, A. I.; Dieden, R. A. NMR and molecular modeling study of the conformations of taxol and of its side chain methylester in aqueous and nonaqueous solution. Tetrahedron 1993, 49, 6545-6560.
    • (1993) Tetrahedron , vol.49 , pp. 6545-6560
    • William, H.J.1    Scott, A.I.2    Dieden, R.A.3
  • 19
    • 0031463596 scopus 로고    scopus 로고
    • Comparative molecular field analysis of a series of paclitaxel analogues
    • Zhu, Q.; Guo, Z.; Huang, N.; Wang, M.; Chu, F. Comparative molecular field analysis of a series of paclitaxel analogues. J. Med. Chem. 1997, 40, 4319-4328.
    • (1997) J. Med. Chem. , vol.40 , pp. 4319-4328
    • Zhu, Q.1    Guo, Z.2    Huang, N.3    Wang, M.4    Chu, F.5
  • 22
    • 10144251769 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationships of the second-generation antitumor taxoids: Exceptional activity against drug-resistant cancer cells
    • Ojima, I.; Slater, J. C.; Michaud, E.; Kuduk, S. D.; Bounaud, P.-Y.; Vrignaud, P.; Bissery, M.-C.; Veith, J. M.; Pera, P.; Bernacki, R. J. Synthesis and structure-activity relationships of the second-generation antitumor taxoids: exceptional activity against drug-resistant cancer cells. J. Med. Chem. 1996, 39, 3889-3896.
    • (1996) J. Med. Chem. , vol.39 , pp. 3889-3896
    • Ojima, I.1    Slater, J.C.2    Michaud, E.3    Kuduk, S.D.4    Bounaud, P.-Y.5    Vrignaud, P.6    Bissery, M.-C.7    Veith, J.M.8    Pera, P.9    Bernacki, R.J.10
  • 24
    • 0036336628 scopus 로고    scopus 로고
    • Synthesis, biological activity and receptor-based 3-D QSAR study of 3′-N-substituted-3′-N-debenzoylpaclitaxel analogues
    • Roh, E. J.; Kim, D.; Choi, J. Y.; Lee, B.-S.; Lee, C. O.; Song, C. E. Synthesis, biological activity and receptor-based 3-D QSAR study of 3′-N-substituted-3′-N-debenzoylpaclitaxel analogues. Bioorg. Med. Chem. 2002, 10, 3135-3143.
    • (2002) Bioorg. Med. Chem. , vol.10 , pp. 3135-3143
    • Roh, E.J.1    Kim, D.2    Choi, J.Y.3    Lee, B.-S.4    Lee, C.O.5    Song, C.E.6
  • 25
    • 0036281198 scopus 로고    scopus 로고
    • A semiempirical study on the electronic structure of 10-deacetylbaccatin-III
    • Braga, S. F.; Galvão, D. S. A semiempirical study on the electronic structure of 10-deacetylbaccatin-III. J. Molecular Graphics Modeling 2002, 21, 57-70.
    • (2002) J. Molecular Graphics Modeling , vol.21 , pp. 57-70
    • Braga, S.F.1    Galvão, D.S.2
  • 26
    • 0842341771 scopus 로고
    • The development and use of quantum -mechanical molecular -models. 76. AMI - A new general -purpose quantum -mechanical molecular -model
    • Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. The development and use of quantum -mechanical molecular -models. 76. AMI - A new general -purpose quantum -mechanical molecular -model. J. Am. Chem. Soc. 1985, 707, 3902.
    • (1985) J. Am. Chem. Soc. , vol.707 , pp. 3902
    • Dewar, M.J.S.1    Zoebisch, E.G.2    Healy, E.F.3    Stewart, J.J.P.4
  • 27
    • 84988129057 scopus 로고
    • Optimization of parameters for semiempirical methods. 1. Method
    • Stewart, J. J. P.; Optimization of parameters for semiempirical methods. 1. Method. J. Comput. Chem. 1989, 10, 209-220.
    • (1989) J. Comput. Chem. , vol.10 , pp. 209-220
    • Stewart, J.J.P.1
  • 28
    • 84988073214 scopus 로고
    • Optimization of parameters for semiempirical methods. 2. Applications
    • Stewart, J. J. P.; Optimization of parameters for semiempirical methods. 2. Applications. J. Comput. Chem. 1989, 10, 221-264.
    • (1989) J. Comput. Chem. , vol.10 , pp. 221-264
    • Stewart, J.J.P.1
  • 29
    • 0004318774 scopus 로고    scopus 로고
    • Quantum Chemistry Program Exchange No. 455
    • MOPAC Program, version 6.0, Quantum Chemistry Program Exchange No. 455. http://qcpe.chem.indiana.edu
    • MOPAC Program, Version 6.0
  • 30
    • 0001582956 scopus 로고    scopus 로고
    • A density functional study of a new family of anticancer drugs: Paclitaxel, taxotere, ephotilone and discoder-molide
    • Ballone, P.; Marchi, M. A density functional study of a new family of anticancer drugs: paclitaxel, taxotere, ephotilone and discoder-molide. J. Phys. Chem. A 1999, 103, 3097-3102.
    • (1999) J. Phys. Chem. A , vol.103 , pp. 3097-3102
    • Ballone, P.1    Marchi, M.2
  • 31
    • 0035942226 scopus 로고    scopus 로고
    • The binding conformation of taxol in β-tubulin: A model based on electron crystallographic density
    • Snyder, J. P.; Nettles, J. H.; Cornell, B.; Downing, K. H.; Nogales, E. The binding conformation of taxol in β-tubulin: a model based on electron crystallographic density. Proc. Natl Acad. Sci. U.S.A. 2001, 98, 5312-5316.
    • (2001) Proc. Natl Acad. Sci. U.S.A. , vol.98 , pp. 5312-5316
    • Snyder, J.P.1    Nettles, J.H.2    Cornell, B.3    Downing, K.H.4    Nogales, E.5
  • 33
    • 0037141974 scopus 로고    scopus 로고
    • Computer modeling of C-2 cluster addition to fullerene C-60
    • Budyka, M. F., Zyubina, T. S.; Ryabenko, A. G. Computer modeling of C-2 cluster addition to fullerene C-60. Intl. J. Quantum Chem. 2002, 88, 652-662.
    • (2002) Intl. J. Quantum Chem. , vol.88 , pp. 652-662
    • Budyka, M.F.1    Zyubina, T.S.2    Ryabenko, A.G.3
  • 34
    • 0028793365 scopus 로고
    • PM3 conformations of C-13 Taxol side chain methyl ester
    • Lozynski M.; Rusinska-Ruszak, D. PM3 conformations of C-13 Taxol side chain methyl ester. Tetrahedron Lett. 1995, 36, 8849-8852.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 8849-8852
    • Lozynski, M.1    Rusinska-Ruszak, D.2
  • 35
    • 0000249365 scopus 로고    scopus 로고
    • PM3 geometry optimization and CNDO/S-CI computation on UV/VIS spectra of large organic structures: Program description and application to poly(tracetylene) hexamer and taxotere
    • Baumann, H.; Martin, R. E.; Diederich, F. PM3 geometry optimization and CNDO/S-CI computation on UV/VIS spectra of large organic structures: program description and application to poly(tracetylene) hexamer and taxotere. J. Comput. Chem. 1999, 20, 396-411.
    • (1999) J. Comput. Chem. , vol.20 , pp. 396-411
    • Baumann, H.1    Martin, R.E.2    Diederich, F.3
  • 36
    • 0036722926 scopus 로고    scopus 로고
    • Applicability of MNDO techniques AM1 and PM3 to ring-structured polymers
    • Dávila, L. Y. A.; Caldas, M. J. Applicability of MNDO techniques AM1 and PM3 to ring-structured polymers. J. Comput. Chem. 2002, 23, 1135-1142.
    • (2002) J. Comput. Chem. , vol.23 , pp. 1135-1142
    • Dávila, L.Y.A.1    Caldas, M.J.2
  • 37
    • 0001853098 scopus 로고    scopus 로고
    • Chem2Pac: A computational chemistry integrator for Windows
    • Cyrillo, M.; Galvão, D. S. Chem2Pac: A computational chemistry integrator for Windows. EPA Newsletter 1999, 67, 31-34 and 34-38. http://www.ifi.unicamp.br/gsonm/chem2pac.
    • (1999) EPA Newsletter , vol.67 , pp. 31-34
    • Cyrillo, M.1    Galvão, D.S.2
  • 38
    • 0345530210 scopus 로고    scopus 로고
    • Pc Spartan Pro 1.0.3. 2000 Wavefunction, Inc. http://www. wavefun.com.
    • (2000) Pc Spartan Pro 1.0.3
  • 40
    • 0000157265 scopus 로고    scopus 로고
    • Theoretical approach to identify carcinogenic activity of polycyclic aromatic hydrocarbons
    • Barone, P. M. V. B.; Camilo, A.; Galvão, D. S. Theoretical approach to identify carcinogenic activity of polycyclic aromatic hydrocarbons. Phys. Rev. Lett. 1996, 77, 1186-1189.
    • (1996) Phys. Rev. Lett. , vol.77 , pp. 1186-1189
    • Barone, P.M.V.B.1    Camilo, A.2    Galvão, D.S.3
  • 41
    • 0034717880 scopus 로고    scopus 로고
    • Electronic indices from semiempirical calculations to identify carcinogenic activity of polycyclic aromatic hydrocarbons
    • Barone, P. M. V. B.; Braga, R. S.; Camilo A.; Galvão, D. S. Electronic indices from semiempirical calculations to identify carcinogenic activity of polycyclic aromatic hydrocarbons. J. Mol. Struct. (THEOCHEM) 2000, 505, 55-66.
    • (2000) J. Mol. Struct. (THEOCHEM) , vol.505 , pp. 55-66
    • Barone, P.M.V.B.1    Braga, R.S.2    Camilo, A.3    Galvão, D.S.4
  • 42
    • 0033219692 scopus 로고    scopus 로고
    • Structure-activity relationship studies of carcinogenic activity of polycyclic aromatic hydrocarbons using calculated molecular descriptors with principal component analysis and neural network methods
    • Vendrame, R.; Braga, R. S.; Takahata, Y.; Galvão, D. S. Structure-activity relationship studies of carcinogenic activity of polycyclic aromatic hydrocarbons using calculated molecular descriptors with principal component analysis and neural network methods. J. Chem. Inf. Comput. Sci. 1999, 39, 1094-1104.
    • (1999) J. Chem. Inf. Comput. Sci. , vol.39 , pp. 1094-1104
    • Vendrame, R.1    Braga, R.S.2    Takahata, Y.3    Galvão, D.S.4
  • 43
    • 0035918042 scopus 로고    scopus 로고
    • Structure-carcinogenic activity relationship studies of polycyclic aromatic hydrocarbons (PAHs) with pattern-recognition methods
    • Vendrame, R.; Braga, R. S.; Takahata, Y.; Galvão, D. S. Structure-carcinogenic activity relationship studies of polycyclic aromatic hydrocarbons (PAHs) with pattern-recognition methods. J. Mol. Struct. (THEOCHEM) 2001, 539, 253-265.
    • (2001) J. Mol. Struct. (THEOCHEM) , vol.539 , pp. 253-265
    • Vendrame, R.1    Braga, R.S.2    Takahata, Y.3    Galvão, D.S.4
  • 44
    • 0036827085 scopus 로고    scopus 로고
    • Identifying relevant molecular descriptors related to carcinogenic activity of polycyclic aromatic hydrocarbons (PAHs) using pattern recognition methods
    • Coluci, V. R.; Vendrame, R.; Braga, R. S.; Galvão, D. S. Identifying Relevant Molecular Descriptors Related to Carcinogenic Activity of Polycyclic Aromatic Hydrocarbons (PAHs) Using Pattern Recognition Methods J. Chem. Inf. Comput. Sci. 2002, 42, 1479-1489.
    • (2002) J. Chem. Inf. Comput. Sci. , vol.42 , pp. 1479-1489
    • Coluci, V.R.1    Vendrame, R.2    Braga, R.S.3    Galvão, D.S.4
  • 45
    • 0033580520 scopus 로고    scopus 로고
    • Structure-activity study of indole-quinones bioreductive alkylating agents
    • Santo, L. L. E.; Galvão, D. S. Structure-activity study of indole-quinones bioreductive alkylating agents. J. Mol. Struct. (THEOCHEM) 1999, 464, 273-279.
    • (1999) J. Mol. Struct. (THEOCHEM) , vol.464 , pp. 273-279
    • Santo, L.L.E.1    Galvão, D.S.2
  • 46
    • 0037049336 scopus 로고    scopus 로고
    • Structure-activity relationship (SAR) studies of the tripos benchmark steroids
    • Vendrame, R.; Coluci, V. R.; Braga, R. S.; Galvão, D. S. Structure-activity relationship (SAR) studies of the tripos benchmark steroids. J. Mol. Struct. (THEOCHEM) 2002, 619, 195-205.
    • (2002) J. Mol. Struct. (THEOCHEM) , vol.619 , pp. 195-205
    • Vendrame, R.1    Coluci, V.R.2    Braga, R.S.3    Galvão, D.S.4
  • 47
    • 0034323972 scopus 로고    scopus 로고
    • Structure-activity relationship studies of substituted 17 alpha-acetoxyprogesterone hormones
    • Braga, R. S.; Vendrame, R.; Galvão, D. S. Structure-activity relationship studies of substituted 17 alpha-acetoxyprogesterone hormones. J. Chem. Inf. Comput. Sci. 2000, 40, 1377-1385.
    • (2000) J. Chem. Inf. Comput. Sci. , vol.40 , pp. 1377-1385
    • Braga, R.S.1    Vendrame, R.2    Galvão, D.S.3
  • 48
    • 0033580522 scopus 로고    scopus 로고
    • Structure-activity relationship study of some inhibitors of HIV-1 integrase
    • Cyrillo, M.; Galvão, D. S. Structure-activity relationship study of some inhibitors of HIV-1 integrase. J. Mol. Struct. (THEOCHEM) 1999, 464, 267-272.
    • (1999) J. Mol. Struct. (THEOCHEM) , vol.464 , pp. 267-272
    • Cyrillo, M.1    Galvão, D.S.2
  • 49
    • 0030586467 scopus 로고    scopus 로고
    • Multivariate techniques in the analysis of meat quality
    • Naes, T.; Baardseth, P.; Helgesen, H.; Isakson, T. Multivariate techniques in the analysis of meat quality. Meat Sci. 1996, 43, s135-s149.
    • (1996) Meat Sci. , vol.43
    • Naes, T.1    Baardseth, P.2    Helgesen, H.3    Isakson, T.4
  • 53
    • 0345098721 scopus 로고    scopus 로고
    • Einsight 3.0. Infometrix, Inc. 2200 Sixth Ave, Suite 833, Seattle WA 98121, 1991
    • Einsight 3.0. Infometrix, Inc. 2200 Sixth Ave, Suite 833, Seattle WA 98121, 1991.


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