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Volumn 39, Issue 7, 1996, Pages 1383-1395

Antitumor agents. 163. Three-dimensional quantitative structure-activity relationship study of 4′-O-demethylepipodophyllotoxin analogs using the modified CoMFA/q2-GRS approach

Author keywords

[No Author keywords available]

Indexed keywords

4' NOREPIPODOPHYLLOTOXIN; ANTINEOPLASTIC AGENT; DAUNORUBICIN; ETOPOSIDE DERIVATIVE; GYRASE INHIBITOR; NOGALAMYCIN; PLANT EXTRACT; PODOPHYLLOTOXIN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0001056916     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9503052     Document Type: Article
Times cited : (92)

References (33)
  • 1
    • 0029622429 scopus 로고
    • Antitumor Agents 162. Cell-Based Assays for Identifying Novel DNA Topoisomerase Inhibitors: Studies on Constituents of Fatsia japonica
    • Kitanaka, S.; Yasuda, I.; Kashiwada, Y.; Hu, C. Q.; Bastow, K. F.; Bori, I. D.; Lee, K. H. Antitumor Agents 162. Cell-Based Assays for Identifying Novel DNA Topoisomerase Inhibitors: Studies on Constituents of Fatsia japonica. J. Nat. Prod. 1995, 58, 1647-1654.
    • (1995) J. Nat. Prod. , vol.58 , pp. 1647-1654
    • Kitanaka, S.1    Yasuda, I.2    Kashiwada, Y.3    Hu, C.Q.4    Bastow, K.F.5    Bori, I.D.6    Lee, K.H.7
  • 3
    • 77049217359 scopus 로고
    • The Biological Effects and the Chemical Composition of Podophyllin, a Review
    • Kelly, M. G.; Hartwell, J. L. The Biological Effects and the Chemical Composition of Podophyllin, a Review. J. Natl. Cancer Inst. 1954, 14, 967-1010
    • (1954) J. Natl. Cancer Inst. , vol.14 , pp. 967-1010
    • Kelly, M.G.1    Hartwell, J.L.2
  • 4
    • 0001308948 scopus 로고
    • Podophyllotoxins
    • Cassady, J. M., Douros, J. D., Eds.; Academic Press, New York
    • Jardin, I Podophyllotoxins. In Anticancer Agents Based on Natural Product Models; Cassady, J. M., Douros, J. D., Eds.; Academic Press, New York, 1980; pp 319-351.
    • (1980) Anticancer Agents Based on Natural Product Models , pp. 319-351
    • Jardin, I.1
  • 5
    • 0027330403 scopus 로고
    • Podophyllotoxin, Steganacin, and Combretastatin: Natural Products That Bind at the Colchicine Site of Tubulin
    • Sackett, D. L. Podophyllotoxin, Steganacin, and Combretastatin: Natural Products That Bind at the Colchicine Site of Tubulin. Pharm Ther. 1993, 59, 163-228.
    • (1993) Pharm Ther. , vol.59 , pp. 163-228
    • Sackett, D.L.1
  • 7
    • 0021905642 scopus 로고
    • Successful Treatment of Resistant Germinal Neoplasms with VP-16 and Cisplatin: Results of a Southeastern Cancer Study Group Trial
    • Hainsworth, J. D.; Williams, S. D.; Einhorn, L. H , Birch, R; Greco, F. A. Successful Treatment of Resistant Germinal Neoplasms with VP-16 and Cisplatin: Results of a Southeastern Cancer Study Group Trial. J. Clin. Oncol. 1985, 3, 666-671.
    • (1985) J. Clin. Oncol. , vol.3 , pp. 666-671
    • Hainsworth, J.D.1    Williams, S.D.2    Einhorn, L.H.3    Birch, R.4    Greco, F.A.5
  • 8
    • 0024405310 scopus 로고
    • Preformulation Study of Etoposide: Identification of Physicochemical Characteristics Responsible for the Low and Erratic Oral Bioavailability of Etoposide
    • Shah, J. C.; Chen, J. R.; Chow, D. Preformulation Study of Etoposide: Identification of Physicochemical Characteristics Responsible for the Low and Erratic Oral Bioavailability of Etoposide. Pharm. Res. 1989, 6, 408-412.
    • (1989) Pharm. Res. , vol.6 , pp. 408-412
    • Shah, J.C.1    Chen, J.R.2    Chow, D.3
  • 9
    • 0000786406 scopus 로고
    • Recent Progress in the Development of Novel Antitumor Etoposide Analogs
    • Zhang, Y.; Lee, K. H. Recent Progress in the Development of Novel Antitumor Etoposide Analogs. Chin. Pharm. J. 1994, 46, 319-369.
    • (1994) Chin. Pharm. J. , vol.46 , pp. 319-369
    • Zhang, Y.1    Lee, K.H.2
  • 10
    • 0024412180 scopus 로고
    • Antitumor Agents, 107. New Cytotoxic 4-Alkylamino Analogues of 4′-Demethylepipodophyllotoxin as Inhibitors of Human DNA Topoisomerase II
    • Lee, K. H.; Imakura, Y.; Haruna, M.; Beers, S. A.; Thurston, L. S.; Dai, H. J.; Chen, C. H. Antitumor Agents, 107. New Cytotoxic 4-Alkylamino Analogues of 4′-Demethylepipodophyllotoxin as Inhibitors of Human DNA Topoisomerase II J. Nat. Prod. 1989, 52, 606-613.
    • (1989) J. Nat. Prod. , vol.52 , pp. 606-613
    • Lee, K.H.1    Imakura, Y.2    Haruna, M.3    Beers, S.A.4    Thurston, L.S.5    Dai, H.J.6    Chen, C.H.7
  • 11
    • 0024988752 scopus 로고
    • Antitumor Agents. 113. New 4β-Arylamino Derivatives of 4́-O-Demethylepipodophyllotoxin and Related Compounds as Potent Inhibitors of Human DNA Topoisomerase II
    • Wang, Z. Q.; Kuo, Y. H.; Schnur, D.; Bowen, J. P.; Liu, S. Y.; Han, F. S.; Chang, J. Y.; Cheng, Y. C.; Lee, K. H. Antitumor Agents. 113. New 4β-Arylamino Derivatives of 4́-O-Demethylepipodophyllotoxin and Related Compounds as Potent Inhibitors of Human DNA Topoisomerase II. J. Med. Chem 1990, 33, 2660-2666.
    • (1990) J. Med. Chem , vol.33 , pp. 2660-2666
    • Wang, Z.Q.1    Kuo, Y.H.2    Schnur, D.3    Bowen, J.P.4    Liu, S.Y.5    Han, F.S.6    Chang, J.Y.7    Cheng, Y.C.8    Lee, K.H.9
  • 12
    • 0028167580 scopus 로고
    • Antitumor Agents. 148. Synthesis and Biological Evaluation of Novel 4β-Amino Derivatives of Etoposide with Better Pharmacological Profiles
    • Zhang, Y. L.; Guo, X.; Cheng, Y. C.; Lee, K. H. Antitumor Agents. 148. Synthesis and Biological Evaluation of Novel 4β-Amino Derivatives of Etoposide with Better Pharmacological Profiles. J. Med. Chem. 1994, 37, 446-452.
    • (1994) J. Med. Chem. , vol.37 , pp. 446-452
    • Zhang, Y.L.1    Guo, X.2    Cheng, Y.C.3    Lee, K.H.4
  • 13
    • 0025350760 scopus 로고
    • Antitumor Agents 111. New 4-Hydroxylated and 4-Halogenated Anilino Derivatives of 4′-Demethylepipodophyllotoxin as Potent Inhibitors of Human DNA Topoisomerase II
    • Lee, K. H., Beers, S. A.; Mori, M.; Wang, Z. Q.; Kuo, Y H.; Li, L.; Liu, S. Y.; Chang, J. Y.; Han, F. S.; Cheng, Y. C. Antitumor Agents 111. New 4-Hydroxylated and 4-Halogenated Anilino Derivatives of 4′-Demethylepipodophyllotoxin as Potent Inhibitors of Human DNA Topoisomerase II. J Med. Chem 1990, 33, 1364-1368.
    • (1990) J Med. Chem , vol.33 , pp. 1364-1368
    • Lee, K.H.1    Beers, S.A.2    Mori, M.3    Wang, Z.Q.4    Kuo, Y.H.5    Li, L.6    Liu, S.Y.7    Chang, J.Y.8    Han, F.S.9    Cheng, Y.C.10
  • 14
    • 0026343096 scopus 로고
    • Antitumor Agents. 120. New 4-Substituted Benzylamine and Benzyl Ether Derivatives of 4′-O-Demethylepipodophyllollotoxin as Potent Inhibitors of Human DNA Topoisomerase II
    • Zhou, X. M.; Wang, Z. Q.; Chang, J. Y.; Chen, H. X.; Cheng, Y C.; Lee, K. H. Antitumor Agents. 120. New 4-Substituted Benzylamine and Benzyl Ether Derivatives of 4′-O-Demethylepipodophyllollotoxin as Potent Inhibitors of Human DNA Topoisomerase II J. Med. Chem. 1991, 34, 3346-3350
    • (1991) J. Med. Chem. , vol.34 , pp. 3346-3350
    • Zhou, X.M.1    Wang, Z.Q.2    Chang, J.Y.3    Chen, H.X.4    Cheng, Y.C.5    Lee, K.H.6
  • 15
    • 0027452746 scopus 로고
    • Antitumor Agents. 125. New 4β-Benzoylamino Derivatives of 4′-O-Demethyl-4-desoxypodophyllotoxin and 4β-Benzoyl Derivatives of 4′-O-Demethylpodophyllotoxin as Potent Inhibitors of Human DNA Topoisomerase II
    • Zhou, X. M.; Wang, Z. Q., Chen, H. X.; Cheng, Y. C., Lee, K. H. Antitumor Agents. 125. New 4β-Benzoylamino Derivatives of 4′-O-Demethyl-4-desoxypodophyllotoxin and 4β-Benzoyl Derivatives of 4′-O-Demethylpodophyllotoxin as Potent Inhibitors of Human DNA Topoisomerase II. Pharm. Res. 1993, 10, 214-219
    • (1993) Pharm. Res. , vol.10 , pp. 214-219
    • Zhou, X.M.1    Wang, Z.Q.2    Chen, H.X.3    Cheng, Y.C.4    Lee, K.H.5
  • 16
    • 0026178922 scopus 로고
    • Catalytic Function of DNA Topoisomerase II
    • Osheroff, N.; Zechiedrich, E. L.; Gale, K. C. Catalytic Function of DNA Topoisomerase II. BioEssays 1991, 13, 269-275
    • (1991) BioEssays , vol.13 , pp. 269-275
    • Osheroff, N.1    Zechiedrich, E.L.2    Gale, K.C.3
  • 18
    • 0024339336 scopus 로고
    • Podophyllotoxin Analogs: Effects on DNA Topoisomerase II, Tubulin Polymerization, Human Tumor KB Cells, and Their VP-16-Resistant Variants
    • Liu, S. Y.; Hwang, B. D.; Haruna, M.; Imakura, Y.; Lee, K H.; Cheng, Y. C. Podophyllotoxin Analogs: Effects on DNA Topoisomerase II, Tubulin Polymerization, Human Tumor KB Cells, and Their VP-16-Resistant Variants. Mol. Pharmacol. 1989, 36, 78-82.
    • (1989) Mol. Pharmacol. , vol.36 , pp. 78-82
    • Liu, S.Y.1    Hwang, B.D.2    Haruna, M.3    Imakura, Y.4    Lee, K.H.5    Cheng, Y.C.6
  • 19
    • 0028200192 scopus 로고
    • Antitumor Agents. 152 in Vitro Inhibitory Activity of Etoposide Derivative NPF AGainst Human Tumor Cell LInes and a Study of Its Conformation by X-ray Crystallography, Molecular Modeling, and NMR Spectroscopy
    • Zhang, Y. L.; Tropsha, A.; McPhail, A. T.; Lee, K. H. Antitumor Agents. 152 In Vitro Inhibitory Activity of Etoposide Derivative NPF AGainst Human Tumor Cell LInes and a Study of Its Conformation by X-ray Crystallography, Molecular Modeling, and NMR Spectroscopy J. Med Chem. 1994, 37, 1460-1464.
    • (1994) J. Med Chem. , vol.37 , pp. 1460-1464
    • Zhang, Y.L.1    Tropsha, A.2    McPhail, A.T.3    Lee, K.H.4
  • 20
    • 0023751431 scopus 로고
    • Comparative Molecular Field Analysis CoMFA. 1. Effect of Shape on Binding of Steroids to Carrier Proteins
    • Cramer, R. D., III; Patterson, D. E.; Bunce, J. D. Comparative Molecular Field Analysis CoMFA). 1. Effect of Shape on Binding of Steroids to Carrier Proteins. J. Am Chem. Soc. 1988, 110, 5959-5967.
    • (1988) J. Am Chem. Soc. , vol.110 , pp. 5959-5967
    • Cramer III, R.D.1    Patterson, D.E.2    Bunce, J.D.3
  • 21
    • 0029655006 scopus 로고
    • 2 Guided Region Selection for Comparative Molecular Field Analysis (CoMFA). A Simple Method to Achieve Consistent Results
    • 2 Guided Region Selection for Comparative Molecular Field Analysis (CoMFA). A Simple Method to Achieve Consistent Results. J. Med Chem 1995, 38, 1060-1066.
    • (1995) J. Med Chem , vol.38 , pp. 1060-1066
    • Cho, S.J.1    Tropsha, A.2
  • 22
    • 0006059658 scopus 로고    scopus 로고
    • Tripos Associates, 1699 South Hanley Road, St. Louis, MO 63144
    • The Sybyl program (version 6.0) is available from Tripos Associates, 1699 South Hanley Road, St. Louis, MO 63144.
    • The Sybyl Program (Version 6.0)
  • 23
    • 84988115618 scopus 로고
    • Validation of the General Purpose Tripos 5.2 Force Field
    • Clark, M.; Cramer, R. D., III; Van Opdenbosh, N. Validation of the General Purpose Tripos 5.2 Force Field. J. Comput. Chem. 1989, 10, 982-1012.
    • (1989) J. Comput. Chem. , vol.10 , pp. 982-1012
    • Clark, M.1    Cramer III, R.D.2    Van Opdenbosh, N.3
  • 24
    • 0027183015 scopus 로고
    • 3D-QSAR of Angiotensin-Converting Enzyme and Thermolysin Inhibitors: A Comparison of CoMFA Models Based on Deduced and Experimentally Determined Active-site Geometries
    • DePriest, S A.; Mayer, D.; Naylor, C. B.; Marshall, G R 3D-QSAR of Angiotensin-Converting Enzyme and Thermolysin Inhibitors: A Comparison of CoMFA Models Based on Deduced and Experimentally Determined Active-site Geometries. J. Am Chem. Soc. 1993, 115, 5372-5384.
    • (1993) J. Am Chem. Soc. , vol.115 , pp. 5372-5384
    • DePriest, S.A.1    Mayer, D.2    Naylor, C.B.3    Marshall, G.R.4
  • 25
    • 0001476124 scopus 로고
    • On the Mechanism of Interaction of DNA Topoisomerase II with Chemotherapeutic Agents
    • Potmesil, M., Kohn, K. W., Eds.; Oxford University Press: New York
    • MacDonald, T. L.; Lehnert, E. K.; Loper, J. T., Chow, K. C., Ross, W. E. On the Mechanism of Interaction of DNA Topoisomerase II with Chemotherapeutic Agents. In DNA Topoisomerase in Cancer; Potmesil, M., Kohn, K. W., Eds.; Oxford University Press: New York, 1991; pp 119-214.
    • (1991) DNA Topoisomerase in Cancer , pp. 119-214
    • MacDonald, T.L.1    Lehnert, E.K.2    Loper, J.T.3    Chow, K.C.4    Ross, W.E.5
  • 26
    • 0023715265 scopus 로고
    • DNA Binding by Epipodophyllotoxms and N-Acyl Anthracyclines: Implications for Mechanism of Topoisomerase II Inhibition
    • Chow, K. C.; MacDonald, T. L.; Ross, W. E. DNA Binding by Epipodophyllotoxms and N-Acyl Anthracyclines: Implications for Mechanism of Topoisomerase II Inhibition. Mol. Pharmacol. 1988, 34, 467-473.
    • (1988) Mol. Pharmacol. , vol.34 , pp. 467-473
    • Chow, K.C.1    MacDonald, T.L.2    Ross, W.E.3
  • 27
    • 0026026263 scopus 로고
    • DNA Intercalating Anti-Tumor Agents
    • Baguley, B. C. DNA Intercalating Anti-Tumor Agents. Anti-Cancer Drug Des. 1991, 6, 1-35.
    • (1991) Anti-Cancer Drug Des. , vol.6 , pp. 1-35
    • Baguley, B.C.1
  • 28
    • 0024997858 scopus 로고
    • Binding of the Antitumor Drug, Nogalamycin and Its Derivatives to DNA: Structural comparison
    • Gao, Y. G.; Liaw, Y. C., Robinson, H.; Wang, A. H. Binding of the Antitumor Drug, Nogalamycin and Its Derivatives to DNA: Structural comparison. Biochemistry 1990, 29, 10307-10316.
    • (1990) Biochemistry , vol.29 , pp. 10307-10316
    • Gao, Y.G.1    Liaw, Y.C.2    Robinson, H.3    Wang, A.H.4
  • 29
    • 0027762073 scopus 로고
    • Three-Dimensional QSAR of Human Immunodeficiency Virus (I) Protease Inhibitors. 1. A CoMFA Study Employing Experimentally-Determined Alignment Rules
    • Waller, C. L.; Oprea, T. I.; Giolitti, A.; Marshall, G. R. Three-Dimensional QSAR of Human Immunodeficiency Virus (I) Protease Inhibitors. 1. A CoMFA Study Employing Experimentally-Determined Alignment Rules. J. Med. Chem. 1993, 36, 4152-4160.
    • (1993) J. Med. Chem. , vol.36 , pp. 4152-4160
    • Waller, C.L.1    Oprea, T.I.2    Giolitti, A.3    Marshall, G.R.4
  • 30
    • 0027266850 scopus 로고
    • Mechanistic Interpretation of the Genotoxicity of Nitrofurans (Antibacterial Agents) Using Quantitative Structure-Activity Relationships and Comparative Molecular Field Analysis
    • Debnath, A. K.; Hansch, C.; Kim, K. H.; Martin, Y. C. Mechanistic Interpretation of the Genotoxicity of Nitrofurans (Antibacterial Agents) Using Quantitative Structure-Activity Relationships and Comparative Molecular Field Analysis. J. Med. Chem. 1993, 36, 1007-1016.
    • (1993) J. Med. Chem. , vol.36 , pp. 1007-1016
    • Debnath, A.K.1    Hansch, C.2    Kim, K.H.3    Martin, Y.C.4
  • 31
    • 0027253921 scopus 로고
    • Structure, DNA Minor Groove Binding, and Base Pair Specificity of Alkyl- and Aryl-Linked Bis(amidinobenzimidazoles) and Bis(amidinoindoles)
    • Fairley, T. A.; Tidwell, R. R.; Donkor, I.; Naiman, N. A.; Ohemeng, K. A.; Lombardy, R. J.; Bentley, J. A.; Cory, M. Structure, DNA Minor Groove Binding, and Base Pair Specificity of Alkyl- and Aryl-Linked Bis(amidinobenzimidazoles) and Bis(amidinoindoles). J. Med. Chem. 1993, 36, 1746-1753.
    • (1993) J. Med. Chem. , vol.36 , pp. 1746-1753
    • Fairley, T.A.1    Tidwell, R.R.2    Donkor, I.3    Naiman, N.A.4    Ohemeng, K.A.5    Lombardy, R.J.6    Bentley, J.A.7    Cory, M.8
  • 32
    • 0019834497 scopus 로고
    • Structural Factors Involved in the Binding of Netropsin and Distamycin A to Nucleic Acids
    • Pullman, B.; Pullman, A. Structural Factors Involved in the Binding of Netropsin and Distamycin A to Nucleic Acids. Stud. Biophys. 1981, 86, 95-102.
    • (1981) Stud. Biophys. , vol.86 , pp. 95-102
    • Pullman, B.1    Pullman, A.2
  • 33
    • 0026178922 scopus 로고
    • Catalytic Function of DNA Topoisomerase II
    • Osheroff, N.; Zechiedrich, E. L.; Gale, K. C. Catalytic Function of DNA Topoisomerase II. BioEssays 1991, 13, 269-275.
    • (1991) BioEssays , vol.13 , pp. 269-275
    • Osheroff, N.1    Zechiedrich, E.L.2    Gale, K.C.3


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