메뉴 건너뛰기




Volumn 15, Issue 5, 2010, Pages 528-540

Molecular modeling and structure-activity relationship of podophyllotoxin and its congeners

Author keywords

Cytotoxicity; Drug screening; Model validation; Podophyllotoxin; Quantitative structure activity relationship

Indexed keywords

ISOXAZOLIGNAN DERIVATIVE; PODOPHYLLOTOXIN DERIVATIVE; PYRAZOLIGNAN DERIVATIVE; TUBULIN; UNCLASSIFIED DRUG;

EID: 77953648640     PISSN: 10870571     EISSN: 1552454X     Source Type: Journal    
DOI: 10.1177/1087057110368994     Document Type: Article
Times cited : (7)

References (29)
  • 1
    • 0001308948 scopus 로고
    • Anticancer agents based on natural product models
    • Cassady JM, Douras JD (eds): New York: Academic Press
    • Jardine I.: Anticancer agents based on natural product models. In Cassady JM, Douras JD (eds): Medicinal Chemistry Monographs. New York: Academic Press, 1980: 319-351.
    • (1980) Medicinal Chemistry Monographs , pp. 319-351
    • Jardine, I.1
  • 2
    • 0013870211 scopus 로고
    • The metaphase-arresting plant alkaloids and cancer chemo therapy
    • Savel H.: The metaphase-arresting plant alkaloids and cancer chemo therapy. Prog Exp Tumor Res 1966 ; 8: 189-224.
    • (1966) Prog Exp Tumor Res , vol.8 , pp. 189-224
    • Savel, H.1
  • 3
    • 0027330403 scopus 로고
    • Podophyllotoxin, steganacin and combretastatin: Natural products that bind at the colchine site of tubulin
    • Sackett DL: Podophyllotoxin, steganacin and combretastatin: natural products that bind at the colchine site of tubulin. Pharm Ther 1993 ; 59: 163-228.
    • (1993) Pharm Ther , vol.59 , pp. 163-228
    • Sackett, D.L.1
  • 4
    • 0031810637 scopus 로고    scopus 로고
    • Podophyllotoxins: Current status and recent developments
    • Damayanthi Y., Lown JW: Podophyllotoxins: current status and recent developments. Curr Med Chem 1998 ; 5: 205-252.
    • (1998) Curr Med Chem , vol.5 , pp. 205-252
    • Damayanthi, Y.1    Lown, J.W.2
  • 5
    • 4744341416 scopus 로고    scopus 로고
    • Design, synthesis and biological evaluation of novel 4β-[(4- benzamido)amino]-4′2-O-demethyl-epipodophyllotoxin derivatives
    • Xiao Z., Bastow KF, Vance JR, Sidwell R., Wang HK, Chen MS,, et al. Design, synthesis and biological evaluation of novel 4β-[(4-benzamido) amino]-4′2-O-demethyl-epipodophyllotoxin derivatives. J Med Chem 2004 ; 47: 5140-5148.
    • (2004) J Med Chem , vol.47 , pp. 5140-5148
    • Xiao, Z.1    Bastow, K.F.2    Vance, J.R.3    Sidwell, R.4    Wang, H.K.5    Chen, M.S.6
  • 6
    • 0034778314 scopus 로고    scopus 로고
    • Thrombolytic therapy
    • Marder VJ: Thrombolytic therapy. Blood Rev 2001 ; 15: 143-157.
    • (2001) Blood Rev , vol.15 , pp. 143-157
    • Marder, V.J.1
  • 7
    • 0033151341 scopus 로고    scopus 로고
    • Frontier orbital energies, hydrophobicity and steric factors as physical QSAR descriptors of molecular mutagenicity: A review with a case study: MX compounds
    • Tuppurainen K.: Frontier orbital energies, hydrophobicity and steric factors as physical QSAR descriptors of molecular mutagenicity: a review with a case study: MX compounds. Chemosphere 1999 ; 38: 3015-3030.
    • (1999) Chemosphere , vol.38 , pp. 3015-3030
    • Tuppurainen, K.1
  • 8
    • 0035263818 scopus 로고    scopus 로고
    • Chem-bioinformatics and QSAR: A review of QSAR lacking positive hydrophobic terms
    • Hansch C., Kurup A., Garg R., Gao H.: Chem-bioinformatics and QSAR: a review of QSAR lacking positive hydrophobic terms. Chem Rev 2001 ; 101: 619-672.
    • (2001) Chem Rev , vol.101 , pp. 619-672
    • Hansch, C.1    Kurup, A.2    Garg, R.3    Gao, H.4
  • 9
    • 0000353230 scopus 로고    scopus 로고
    • The characterization of chemical structures using molecular properties: A survey
    • Livingstone DL: The characterization of chemical structures using molecular properties: a survey. J Chem Inf Comput Sci 2000 ; 40: 195-209.
    • (2000) J Chem Inf Comput Sci , vol.40 , pp. 195-209
    • Livingstone, D.L.1
  • 10
    • 0032015070 scopus 로고    scopus 로고
    • Mining the NCI anticancer drug discovery databases: Genetic function approximation for the QSAR study of anticancer ellipticine analogues
    • Shi LM, Fan Y., Myers TG, Paul JN: Mining the NCI anticancer drug discovery databases: genetic function approximation for the QSAR study of anticancer ellipticine analogues. J Chem Inf Comput Sci 1998 ; 38: 189-199.
    • (1998) J Chem Inf Comput Sci , vol.38 , pp. 189-199
    • Shi, L.M.1    Fan, Y.2    Myers, T.G.3    Paul, J.N.4
  • 11
    • 28544437675 scopus 로고    scopus 로고
    • Application of validated QSAR models of D1 dopaminergic antagonists for database mining
    • Oloff S., Mailman RB, Trospha A.: Application of validated QSAR models of D1 dopaminergic antagonists for database mining. J Med Chem 2005 ; 48: 7322-7332.
    • (2005) J Med Chem , vol.48 , pp. 7322-7332
    • Oloff, S.1    Mailman, R.B.2    Trospha, A.3
  • 12
    • 23244453314 scopus 로고    scopus 로고
    • A linear discrimination analysis based virtual screening of trichomonacidal lead-like compounds: Outcomes of in silico studies supported by experimental results
    • Meneses-Marcel Y., Marrero-Ponce Y., Machado-Tugores A., Monterro-Torres DM, Pereira JA, Escario JJ,, et al. A linear discrimination analysis based virtual screening of trichomonacidal lead-like compounds: outcomes of in silico studies supported by experimental results. Bioorg Med Chem Lett 2005 ; 15: 3838-3843.
    • (2005) Bioorg Med Chem Lett , vol.15 , pp. 3838-3843
    • Meneses-Marcel, Y.1    Marrero-Ponce, Y.2    MacHado-Tugores, A.3    Monterro-Torres, D.M.4    Pereira, J.A.5    Escario, J.J.6
  • 13
    • 32344446616 scopus 로고    scopus 로고
    • A QSAR model for in silico screening of MAO-A inhibitors: Prediction, synthesis, and biological assay of novel coumarins
    • Santana L., Uriarte H., Gonzalez-Diaz H., Zagotto R., Soto-Otero E., Mendez-Alvarez J.: A QSAR model for in silico screening of MAO-A inhibitors: prediction, synthesis, and biological assay of novel coumarins. J Med Chem 2006 ; 49: 1149-1156.
    • (2006) J Med Chem , vol.49 , pp. 1149-1156
    • Santana, L.1    Uriarte, H.2    Gonzalez-Diaz, H.3    Zagotto, R.4    Soto-Otero, E.5    Mendez-Alvarez, J.6
  • 14
    • 33750521975 scopus 로고    scopus 로고
    • Quantitative structure activity relationship studies of aryl heterocycle-based thrombin inhibitors
    • Deswal S., Roy N.: Quantitative structure activity relationship studies of aryl heterocycle-based thrombin inhibitors. Eur J Med Chem 2006 ; 41: 1339-1346.
    • (2006) Eur J Med Chem , vol.41 , pp. 1339-1346
    • Deswal, S.1    Roy, N.2
  • 16
    • 0034696048 scopus 로고    scopus 로고
    • 4-Aza-2, 3-dehydro-4-deoxypodophyllotoxin: Simple Aza-podophyllotoxin analogues possessing potent cytotoxicity
    • Hitotsuyanagi Y., Fukuyo M., Kyoko T., Kobayashi M., Ozeki A., Itokawa H.,, et al. 4-Aza-2, 3-dehydro-4-deoxypodophyllotoxin: simple Aza-podophyllotoxin analogues possessing potent cytotoxicity. Bioorg Med Chem Lett 2006 ; 10: 315-317.
    • (2006) Bioorg Med Chem Lett , vol.10 , pp. 315-317
    • Hitotsuyanagi, Y.1    Fukuyo, M.2    Kyoko, T.3    Kobayashi, M.4    Ozeki, A.5    Itokawa, H.6
  • 17
    • 0035686492 scopus 로고    scopus 로고
    • Oral vinorelbine pharmacokinetics and absolute bioavailability study in patients with solid tumors
    • Marty M., Fumoleau P., Adenis A., Rousseau Y., Merrouche Y., Robinet G.,, et al. Oral vinorelbine pharmacokinetics and absolute bioavailability study in patients with solid tumors. Ann Oncol 2001 ; 12: 1643-1649.
    • (2001) Ann Oncol , vol.12 , pp. 1643-1649
    • Marty, M.1    Fumoleau, P.2    Adenis, A.3    Rousseau, Y.4    Merrouche, Y.5    Robinet, G.6
  • 18
    • 0018083128 scopus 로고
    • Structureactivity study of the inhibition of microtubules assembly in vitro by podophyllotoxin and its congeners
    • Loike JD, Brewer CF, Sternlicht H., Gensler WJ, Horwitz SB: Structureactivity study of the inhibition of microtubules assembly in vitro by podophyllotoxin and its congeners. Cancer Res 1978 ; 38: 2688-2693.
    • (1978) Cancer Res , vol.38 , pp. 2688-2693
    • Loike, J.D.1    Brewer, C.F.2    Sternlicht, H.3    Gensler, W.J.4    Horwitz, S.B.5
  • 19
    • 49449090514 scopus 로고    scopus 로고
    • Schrodinger LLC: Retrieved April 24, 2007, from http://www.schrodinger. com
    • (2007) Schrodinger LLC
  • 20
    • 77953647608 scopus 로고    scopus 로고
    • Fukuoka, Japan: Fujitsu Kyushu System Engineering Ltd.
    • ADME Works ModelBuilder, version 4.5. Fukuoka, Japan: Fujitsu Kyushu System Engineering Ltd., 2007.
    • (2007) ADME Works ModelBuilder, Version 4.5
  • 22
    • 41949116226 scopus 로고    scopus 로고
    • On some aspects of variable selection for partial least squares regression models
    • Roy PP, Roy K.: On some aspects of variable selection for partial least squares regression models. QSAR Comb Sci 2008 ; 27: 302-313.
    • (2008) QSAR Comb Sci , vol.27 , pp. 302-313
    • Roy, P.P.1    Roy, K.2
  • 23
    • 66149123707 scopus 로고    scopus 로고
    • Exploring 2D and 3D QSARs of 2,4-diphenyl-1,3-oxazolines for ovicidal activity against Tetranychus urticae
    • Roy K., Paul S.: Exploring 2D and 3D QSARs of 2,4-diphenyl-1,3-oxazolines for ovicidal activity against Tetranychus urticae. QSAR Comb Sci 2008 ; 28: 406-425.
    • (2008) QSAR Comb Sci , vol.28 , pp. 406-425
    • Roy, K.1    Paul, S.2
  • 24
    • 2442428176 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: The first QSAR study on inhibition of tumor-associated isoenzyme IX with aromatic and heterocyclic sulfonamides
    • Jaiswal M., Khadikar PV, Scozzafava A., Supuran CT: Carbonic anhydrase inhibitors: the first QSAR study on inhibition of tumor-associated isoenzyme IX with aromatic and heterocyclic sulfonamides. Bioorg Med Chem Lett 2004 ; 14: 3283-3290.
    • (2004) Bioorg Med Chem Lett , vol.14 , pp. 3283-3290
    • Jaiswal, M.1    Khadikar, P.V.2    Scozzafava, A.3    Supuran, C.T.4
  • 25
    • 0031660150 scopus 로고    scopus 로고
    • Inhibition of oral bacteria by phenolic compounds. Part 1. QSAR analysis using molecular connectivity
    • Shapiro S., Guggenheim B.: Inhibition of oral bacteria by phenolic compounds: Part 1. QSAR analysis using molecular connectivity. Quant Struct Act Relat 1998 ; 17: 327-337. (Pubitemid 28401255)
    • (1998) Quantitative Structure-Activity Relationships , vol.17 , Issue.4 , pp. 327-337
    • Shapiro, S.1    Guggenheim, B.2
  • 26
    • 0018742295 scopus 로고
    • Conformational analysis of podophyllotoxin and its congeners: Structure-activity relationship in microtubule assembly
    • Brewer CF, Loik JD, Horwitz SB, Sternlicht H., Gensler WJ: Conformational analysis of podophyllotoxin and its congeners: structure-activity relationship in microtubule assembly. J Med Chem 1979 ; 22: 215-221.
    • (1979) J Med Chem , vol.22 , pp. 215-221
    • Brewer, C.F.1    Loik, J.D.2    Horwitz, S.B.3    Sternlicht, H.4    Gensler, W.J.5
  • 27
    • 45949120296 scopus 로고
    • Description of molecular shape applied in studies of structure/activity and structure/property relationships
    • Rohrbaugh RH, Jurs PC: Description of molecular shape applied in studies of structure/activity and structure/property relationships. Anal Chim Acta 1987 ; 199: 99-109.
    • (1987) Anal Chim Acta , vol.199 , pp. 99-109
    • Rohrbaugh, R.H.1    Jurs, P.C.2
  • 28
    • 0023324504 scopus 로고
    • Molecular shape and prediction of high-performance liquid chromatographic retention indexes of polycyclic aromatic hydrocarbons
    • Rohrbaugh RH, Jurs PC: Molecular shape and prediction of high-performance liquid chromatographic retention indexes of polycyclic aromatic hydrocarbons. Anal Chem 1987 ; 59: 1048-1054.
    • (1987) Anal Chem , vol.59 , pp. 1048-1054
    • Rohrbaugh, R.H.1    Jurs, P.C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.