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Volumn 48, Issue 2, 2005, Pages 593-603

Synthesis and biological study of a new series of 4′- demethylepipodophyllotoxin derivatives

Author keywords

[No Author keywords available]

Indexed keywords

11 OXO 13 DEOXO 4' NOREPIPODOPHYLLOTOXIN 4 [N [2 (N',N' DIMETHYLAMINOETHYL)]]CARBAMATE; 4' NOREPIPODOPHYLLOTOXIN 4 [N [2 (N',N' DIMETHYLAMINOETHYL)]]CARBAMATE; 4' NOREPIPODOPHYLLOTOXIN DERIVATIVE; DNA TOPOISOMERASE (ATP HYDROLYSING); EPIPODOPHYLLOTOXIN DERIVATIVE; ETOPOSIDE; UNCLASSIFIED DRUG;

EID: 19944430141     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0495733     Document Type: Article
Times cited : (43)

References (35)
  • 1
    • 0028144889 scopus 로고
    • Etoposide: Current status and future perspectives in the management of malignant neoplasms
    • Belani, C. P.; Doyle, L. A.; Aisner, J. Etoposide: Current status and future perspectives in the management of malignant neoplasms. Cancer Chemother. Pharmacol 1994, 34 Suppl. S118-126.
    • (1994) Cancer Chemother. Pharmacol. , vol.34 , Issue.SUPPL.
    • Belani, C.P.1    Doyle, L.A.2    Aisner, J.3
  • 2
    • 0032168167 scopus 로고    scopus 로고
    • Etoposide: Four decades of development of a topoisomerase II inhibitor
    • Hande, K. R. Etoposide: Four decades of development of a topoisomerase II inhibitor. Eur. J. Cancer 1998, 34, 1514-1521.
    • (1998) Eur. J. Cancer , vol.34 , pp. 1514-1521
    • Hande, K.R.1
  • 4
    • 0037470042 scopus 로고    scopus 로고
    • A two-drug model for etoposide action against human topoisomerase IIα
    • Bromberg, K. D.; Burgin, A. B.; Osheroff, N. A two-drug model for etoposide action against human topoisomerase IIα. J. Biol. Chem. 2003, 278, 7406-7412.
    • (2003) J. Biol. Chem. , vol.278 , pp. 7406-7412
    • Bromberg, K.D.1    Burgin, A.B.2    Osheroff, N.3
  • 5
    • 0033628701 scopus 로고    scopus 로고
    • Topoisomerase II as a target for anticancer drugs: When enzymes stop being nice
    • Fortune, J. M.; Osheroff, N. Topoisomerase II as a target for anticancer drugs: When enzymes stop being nice. Prog. Nucleic Acid Res. Mol. Biol. 2000, 64, 221-253.
    • (2000) Prog. Nucleic Acid Res. Mol. Biol. , vol.64 , pp. 221-253
    • Fortune, J.M.1    Osheroff, N.2
  • 7
    • 0034923502 scopus 로고    scopus 로고
    • DNA topoisomerases: Structure, function, and mechanism
    • Champoux, J. J. DNA topoisomerases: Structure, function, and mechanism. Annu. Rev. Biochem. 2001, 70, 369-413.
    • (2001) Annu. Rev. Biochem. , vol.70 , pp. 369-413
    • Champoux, J.J.1
  • 8
    • 0032189945 scopus 로고    scopus 로고
    • DNA sequence selectivity of topoisomerases and topoisomerase poisons
    • Capranico, G.; Binaschi, M. DNA sequence selectivity of topoisomerases and topoisomerase poisons. Biochim. Biophys. Acta 1998, 1400, 185-194.
    • (1998) Biochim. Biophys. Acta , vol.1400 , pp. 185-194
    • Capranico, G.1    Binaschi, M.2
  • 9
    • 0032190561 scopus 로고    scopus 로고
    • Mechanism of action of eukaryotic topoisomerase II and drugs targeted to the enzyme
    • Burden, D. A.; Osheroff, N. Mechanism of action of eukaryotic topoisomerase II and drugs targeted to the enzyme. Biochim. Biophys. Acta 1998, 1400, 139-154.
    • (1998) Biochim. Biophys. Acta , vol.1400 , pp. 139-154
    • Burden, D.A.1    Osheroff, N.2
  • 10
    • 0028144885 scopus 로고
    • Pharmacodynamics and long-term toxicity of etoposide
    • Kobayashi, K.; Ratain, M. J. Pharmacodynamics and long-term toxicity of etoposide. Cancer Chemother. Pharmacol. 1994, 34 Suppl. S64-8.
    • (1994) Cancer Chemother. Pharmacol. , vol.34 , Issue.SUPPL.
    • Kobayashi, K.1    Ratain, M.J.2
  • 11
    • 0027208041 scopus 로고
    • Synthesis and biological activity of 4-beta-alkyl derivatives containing hydroxy, amino, and amido groups of (4′-O-demethyl-4-desoxypodophyllotoxin as antitumor agents
    • Terada, T.; Fujimoto, K.; Nomura, M.; Yamashita, J.; Wierzba, K.; Yamazaki, R.; Shibata, J.; Sugimoto, Y.; Yamada, Y.; Kobunai, T.; et al. Synthesis and biological activity of 4-beta-alkyl derivatives containing hydroxy, amino, and amido groups of (4′-O-demethyl-4-desoxypodophyllotoxin as antitumor agents. J. Med. Chem. 1993, 36, 1689-1699.
    • (1993) J. Med. Chem. , vol.36 , pp. 1689-1699
    • Terada, T.1    Fujimoto, K.2    Nomura, M.3    Yamashita, J.4    Wierzba, K.5    Yamazaki, R.6    Shibata, J.7    Sugimoto, Y.8    Yamada, Y.9    Kobunai, T.10
  • 12
    • 0032784679 scopus 로고
    • A novel podophyllotoxin-derived compound GL-331 is more potent than its congener VP-16 in killing refractory cancer cells
    • Huang, T. S.; Lee, C. C.; Chao, Y.; Shu, C. H.; Chen, L. T.; Chen, L. L.; Chen, M. H.; Yuan, C. C.; Whang-Peng, J. A novel podophyllotoxin-derived compound GL-331 is more potent than its congener VP-16 in killing refractory cancer cells. Pharm Res. 1990, 16, 997-1002.
    • (1990) Pharm Res. , vol.16 , pp. 997-1002
    • Huang, T.S.1    Lee, C.C.2    Chao, Y.3    Shu, C.H.4    Chen, L.T.5    Chen, L.L.6    Chen, M.H.7    Yuan, C.C.8    Whang-Peng, J.9
  • 14
    • 0035936547 scopus 로고    scopus 로고
    • DNA topoisomerase II as the target for the anticancer drug TOP-53: Mechanistic basis for drug action
    • Byl, J. A.; Cline, S. D.; Utsugi, T.; Kobunai, T.; Yamada, Y.; Osheroff, N. DNA topoisomerase II as the target for the anticancer drug TOP-53: Mechanistic basis for drug action. Biochemistry 2001, 40, 712-718.
    • (2001) Biochemistry , vol.40 , pp. 712-718
    • Byl, J.A.1    Cline, S.D.2    Utsugi, T.3    Kobunai, T.4    Yamada, Y.5    Osheroff, N.6
  • 17
    • 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
  • 18
    • 0021081069 scopus 로고
    • Comparative cytotoxic and cytokinetic effects of the epipodophyllotoxins 4′-demethylepipodophyllotoxin-9-(4,6-O-2-ethylidene-β-D- glucopyranoside) and 4′-demethylepipodophyllotoxin-9-(4,6-O-2-thenylidene- β-D-glucopyranoside) and their metabolites on human leukemic lymphoblasts
    • Dow, L.; Sinkule, J. A.; Look, A. T.; Horvath, A.; Evans W. E. Comparative cytotoxic and cytokinetic effects of the epipodophyllotoxins 4′-demethylepipodophyllotoxin-9-(4,6-O-2-ethylidene-β-D- glucopyranoside) and 4′-demethylepipodophyllotoxin-9-(4,6-O-2-thenylidene- β-D-glucopyranoside) and their metabolites on human leukemic lymphoblasts. Cancer Res. 1983, 43, 5699-5706.
    • (1983) Cancer Res. , vol.43 , pp. 5699-5706
    • Dow, L.1    Sinkule, J.A.2    Look, A.T.3    Horvath, A.4    Evans, W.E.5
  • 20
    • 0027953563 scopus 로고
    • New γ-lactone ring-modified arylamino etoposide analogs as inhibitors of human DNA topoisomerase II
    • Zhou, X. M.; Lee, K. J.; Cheng, J.; Wu, S. S.; Chen, H. X.; Guo, X.; Cheng, Y. C.; Lee, K. H. New γ-lactone ring-modified arylamino etoposide analogs as inhibitors of human DNA topoisomerase II. J. Med. Chem. 1994, 37, 287-292.
    • (1994) J. Med. Chem. , vol.37 , pp. 287-292
    • Zhou, X.M.1    Lee, K.J.2    Cheng, J.3    Wu, S.S.4    Chen, H.X.5    Guo, X.6    Cheng, Y.C.7    Lee, K.H.8
  • 21
    • 12344319595 scopus 로고    scopus 로고
    • The Sybyl program (version 6.0) is available from Tripos Associates, 1699 South Hanley Road, St. Louis, MO 63144. CS ChemBats3D Pro software is available from CambridgeSoft Corp., Cambridge, MA)
    • The Sybyl program (version 6.0) is available from Tripos Associates, 1699 South Hanley Road, St. Louis, MO 63144. CS ChemBats3D Pro software is available from CambridgeSoft Corp., Cambridge, MA).
  • 22
    • 18544393471 scopus 로고    scopus 로고
    • Binding of etoposide to topoisomerase II in the absence of DNA: Decreased affinity as a mechanism of drug resistance
    • Kingma, P. S.; Burden, D. A.; Osheroff, N. Binding of etoposide to topoisomerase II in the absence of DNA: Decreased affinity as a mechanism of drug resistance. Biochemistry 1999, 38, 3457-3461.
    • (1999) Biochemistry , vol.38 , pp. 3457-3461
    • Kingma, P.S.1    Burden, D.A.2    Osheroff, N.3
  • 23
    • 0035852792 scopus 로고    scopus 로고
    • Analysis of etoposide binding to subdomains of human DNA topoisomerase II alpha in the absence of DNA
    • Leroy, D.; Kajava, A. V.; Frei, C.; Gasser, S. M. Analysis of etoposide binding to subdomains of human DNA topoisomerase II alpha in the absence of DNA. Biochemistry 2001, 40, 1624-1634.
    • (2001) Biochemistry , vol.40 , pp. 1624-1634
    • Leroy, D.1    Kajava, A.V.2    Frei, C.3    Gasser, S.M.4
  • 24
    • 0031810637 scopus 로고    scopus 로고
    • Podophyllotoxins: Current status and recent developments
    • Damayanthi, Y.; Lown J. W. 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
  • 26
    • 0030008968 scopus 로고    scopus 로고
    • Inhibition of DNA topoisomerase II by azaelliptitoxins functionnalized in the variable substituent domain
    • Tepe, J. J.; Madalengoitia, J. DS.; Slunt, K. M.; Werbovetz, K. W.; Spoors, P. G.; Macdonald, T. L. Inhibition of DNA topoisomerase II by azaelliptitoxins functionnalized in the variable substituent domain. J. Med. Chem. 1996, 39, 2188-2196.
    • (1996) J. Med. Chem. , vol.39 , pp. 2188-2196
    • Tepe, J.J.1    Madalengoitia, J.D.S.2    Slunt, K.M.3    Werbovetz, K.W.4    Spoors, P.G.5    Macdonald, T.L.6
  • 27
    • 0037161603 scopus 로고    scopus 로고
    • Antitumor agents. 213. Modeling of epipodophyllotoxin derivatives using variable selection k nearest neighbor QSAR method
    • Xiao, Z.; Xiao, Y.-D.; Feng, J.; Golbraikh, A.; Tropsha, A.; Lee, K. H. Antitumor Agents. 213. Modeling of epipodophyllotoxin derivatives using variable selection k nearest neighbor QSAR Method. J Med. Chem. 2002, 45, 2294-2309.
    • (2002) J. Med. Chem. , vol.45 , pp. 2294-2309
    • Xiao, Z.1    Xiao, Y.-D.2    Feng, J.3    Golbraikh, A.4    Tropsha, A.5    Lee, K.H.6
  • 29
    • 12344273075 scopus 로고
    • Synthetic analgesics. Part VIII. Further attempts to prepare 3-Phenylpiperidine derivatives
    • Avison, A. W. D.; Morrison, A. L. Synthetic Analgesics. Part VIII. Further attempts to prepare 3-Phenylpiperidine derivatives. J. Chem. Soc. 1950, 1474-1477.
    • (1950) J. Chem. Soc. , pp. 1474-1477
    • Avison, A.W.D.1    Morrison, A.L.2
  • 30
    • 0025626401 scopus 로고
    • Flow cytometric evaluation of the cell cycle perturbations induced by S12363, a new vinca alkaloid derivative
    • Leonce, S.; Anstett, M.; Combe-Perez, V.; Pierre, A. Flow cytometric evaluation of the cell cycle perturbations induced by S12363, a new vinca alkaloid derivative. Anti Cancer Drugs 1990, 1, 179-183.
    • (1990) Anti Cancer Drugs , vol.1 , pp. 179-183
    • Leonce, S.1    Anstett, M.2    Combe-Perez, V.3    Pierre, A.4
  • 33
    • 0033971812 scopus 로고    scopus 로고
    • Histology and sensitivity to anticancer drugs of two human non-small cell lung carcinomas implanted in the pleural cavity of nude mice
    • Kraus-Berthier, L.; Jan, M.; Guilbaud, N.; Naze, M.; Pierré, A.; Atassi, G. Histology and sensitivity to anticancer drugs of two human non-small cell lung carcinomas implanted in the pleural cavity of nude mice. Clin. Cancer Res. 2000, 6, 297-304.
    • (2000) Clin. Cancer Res. , vol.6 , pp. 297-304
    • Kraus-Berthier, L.1    Jan, M.2    Guilbaud, N.3    Naze, M.4    Pierré, A.5    Atassi, G.6
  • 35
    • 0018841140 scopus 로고
    • Structure-Antitubulin activity relationships in steganacin congeners and analogues. Inhibition of tubulin polymerization in vitro by (±)- isodoxypodophyllotoxin
    • Zavala, F.; Guenard, D.; Robin, J.-P.; Brown, E. Structure-Antitubulin activity relationships in steganacin congeners and analogues. Inhibition of tubulin polymerization in vitro by (±)-isodoxypodophyllotoxin. J. Med. Chem. 1980, 23, 546-549.
    • (1980) J. Med. Chem. , vol.23 , pp. 546-549
    • Zavala, F.1    Guenard, D.2    Robin, J.-P.3    Brown, E.4


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