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Volumn 47, Issue 5, 2004, Pages 1214-1222

Synthesis and Biological Evaluation of New Selective Cytotoxic Cyclolignans Derived from Podophyllotoxin

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOLIGNAN DERIVATIVE; LIGNAN DERIVATIVE; PODOPHYLLOTOXIN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 10744221342     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030978h     Document Type: Article
Times cited : (56)

References (37)
  • 1
    • 0033083666 scopus 로고    scopus 로고
    • Lignans, Neolignans and Related Compounds
    • Ward, R. S. Lignans, Neolignans and Related Compounds. Nat. Prod. Rep. 1999, 16, 75-96.
    • (1999) Nat. Prod. Rep. , vol.16 , pp. 75-96
    • Ward, R.S.1
  • 4
    • 0015601539 scopus 로고
    • Activity of a New Glycosidic Lignan Derivative (VP-16-213) Related to Podophyllotoxin in Experimental Tumors
    • (a) Stähelin, H. Activity of a New Glycosidic Lignan Derivative (VP-16-213) Related to Podophyllotoxin in Experimental Tumors. Eur. J. Cancer 1973, 9, 215-221.
    • (1973) Eur. J. Cancer , vol.9 , pp. 215-221
    • Stähelin, H.1
  • 5
    • 0032168167 scopus 로고    scopus 로고
    • Etoposide: Four Decades of Development of a Topoisomerase II Inhibitor
    • (b) 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
  • 6
    • 0014827776 scopus 로고
    • 4′-Demethylepipodophyllotoxin Thenylidene Glucoside (VM-26), a Podophyllum Compound with a New Mechanism of Action
    • Stähelin, H. 4′-Demethylepipodophyllotoxin Thenylidene Glucoside (VM-26), a Podophyllum Compound with a New Mechanism of Action. Eur. J. Cancer 1970, 6, 303-311.
    • (1970) Eur. J. Cancer , vol.6 , pp. 303-311
    • Stähelin, H.1
  • 7
    • 0030477322 scopus 로고    scopus 로고
    • Etoposide Phosphate: What, Why, Where, and How?
    • (a) Schacter, L. Etoposide Phosphate: What, Why, Where, and How?. Semin-Oncol. 1996, 23, 1-7.
    • (1996) Semin-Oncol. , vol.23 , pp. 1-7
    • Schacter, L.1
  • 8
    • 0029856304 scopus 로고    scopus 로고
    • Etoposide Phosphate, the Water Soluble Prodrug of Etoposide
    • (b) Witterland, A. H.; Koks, C. H.; Beijinen, J. H. Etoposide Phosphate, the Water Soluble Prodrug of Etoposide. Pharm. World Sci. 1996, 18, 163-170.
    • (1996) Pharm. World Sci. , vol.18 , pp. 163-170
    • Witterland, A.H.1    Koks, C.H.2    Beijinen, J.H.3
  • 9
    • 0000734820 scopus 로고    scopus 로고
    • Antitumor Agents. 164. Podophenazine, 2′′,3′′ -Dichloropodophenazine, Benzopodophenazine and their 4β-p-Nitroaniline Derivatives as Novel DNA Topoisomerase II Inhibitors
    • Cho, S. J.; Kashiwada, Y.; Bastow, K. F.; Cheng, Y. C.; Lee, K. H. Antitumor Agents. 164. Podophenazine, 2′′,3′′ -Dichloropodophenazine, Benzopodophenazine and their 4β-p-Nitroaniline Derivatives as Novel DNA Topoisomerase II Inhibitors. J. Med. Chem. 1996, 39, 1396-1402.
    • (1996) J. Med. Chem. , vol.39 , pp. 1396-1402
    • Cho, S.J.1    Kashiwada, Y.2    Bastow, K.F.3    Cheng, Y.C.4    Lee, K.H.5
  • 10
    • 0037076856 scopus 로고    scopus 로고
    • Microtubule Damaging Agents Induce Apoptosis in HL-60 Cells and G2/M Cell Cycle Arrest in HT-29
    • Tseng, C. J.; Wang, Y. J.; Liang, Y. C.; Jeng, J. H.; Lee, W. S.; Lin, J. K.; Chen, C. H.; Liu, I. C.; Ho, Y. S. Microtubule Damaging Agents Induce Apoptosis in HL-60 Cells and G2/M Cell Cycle Arrest in HT-29. Toxicology 2002, 175, 123-142.
    • (2002) Toxicology , vol.175 , pp. 123-142
    • Tseng, C.J.1    Wang, Y.J.2    Liang, Y.C.3    Jeng, J.H.4    Lee, W.S.5    Lin, J.K.6    Chen, C.H.7    Liu, I.C.8    Ho, Y.S.9
  • 11
    • 0036292462 scopus 로고    scopus 로고
    • Flow Cytometric Estimation on Cytotoxic Activity of Leaf Extracts from Seashore Plants in Subtropical Japan: Isolation, Quantification and Cytotoxic Action of (-)-Deoxypodophyllotoxin
    • Masuda, T.; Oyama, Y.; Yonemori, S.; Takeda, Y.; Yamazaki Y.; Mizuguchi, S.; Nakata, M.; Tanaka, T.; Chikahisa, L.; Inaba, Y.; Okada, Y. Flow Cytometric Estimation on Cytotoxic Activity of Leaf Extracts from Seashore Plants in Subtropical Japan: Isolation, Quantification and Cytotoxic Action of (-)-Deoxypodophyllotoxin. Phytother. Res. 2002, 16, 353-358.
    • (2002) Phytother. Res. , vol.16 , pp. 353-358
    • Masuda, T.1    Oyama, Y.2    Yonemori, S.3    Takeda, Y.4    Yamazaki, Y.5    Mizuguchi, S.6    Nakata, M.7    Tanaka, T.8    Chikahisa, L.9    Inaba, Y.10    Okada, Y.11
  • 12
    • 0032784679 scopus 로고    scopus 로고
    • A Novel Podophyllotoxin-Derived Compound GL331 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 GL331 is more Potent than its Congener VP-16 in Killing Refractory Cancer Cells. Pharm. Res. 1999, 16, 997-1002.
    • (1999) 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
  • 13
    • 0034018817 scopus 로고    scopus 로고
    • In vitro Evaluation of GL331's Cancer Cell Killing and Apoptosis-inducing Activity in Combination with other Chemotherapeutic Agents
    • Huang, T. S.; Shu, C. H.; Lee, C. C.; Chen, L. T.; Whang-Peng, J. In vitro Evaluation of GL331's Cancer Cell Killing and Apoptosis-inducing Activity in Combination with other Chemotherapeutic Agents. Apoptosis 2000, 5, 79-85.
    • (2000) Apoptosis , vol.5 , pp. 79-85
    • Huang, T.S.1    Shu, C.H.2    Lee, C.C.3    Chen, L.T.4    Whang-Peng, J.5
  • 14
    • 0031810637 scopus 로고    scopus 로고
    • Podophyllotoxins: Current Status and Recent Developments
    • (a) 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
  • 20
    • 0026322408 scopus 로고
    • Interference of Epipodophyllotoxins Natural Lignanolides with Topoisomerase A Proposed Molecular Mechanism
    • Eich, E.; Schulz, J.; Kaloga, M.; Merz, H.; Schroder, H. C.; Muller, E. G. Interference of Epipodophyllotoxins and Natural Lignanolides with Topoisomerase II: A Proposed Molecular Mechanism. Planta Med. 1991, 57, (Supp. 2), A7.
    • (1991) Planta Med. , vol.57 , Issue.SUPPL. 2
    • Eich, E.1    Schulz, J.2    Kaloga, M.3    Merz, H.4    Schroder, H.C.5    Muller II, E.G.6
  • 23
    • 0037212083 scopus 로고    scopus 로고
    • Homocamptothecins: Potent Topoisomerase I Inhibitors and Promising Anticancer Drugs
    • (a) Bailly, C. Homocamptothecins: Potent Topoisomerase I Inhibitors and Promising Anticancer Drugs. Crit. Rev. Oncol. Hematol. 2003, 45, 91-108.
    • (2003) Crit. Rev. Oncol. Hematol. , vol.45 , pp. 91-108
    • Bailly, C.1
  • 25
    • 0030933558 scopus 로고    scopus 로고
    • The Large-Scale Isolation of Deoxypodophyllotoxin from Rhizomes of Anthriscus sylvestris Followed by its Bioconversion into 5-Methoxypodophyllotoxin β-D-Glucoside by Cell Cultures of Linum flavum
    • Van Uden, W.; Bos, J. A.; Boeke, G. M.; Woerdenbag, H. J.; Pras, N. The Large-Scale Isolation of Deoxypodophyllotoxin from Rhizomes of Anthriscus sylvestris Followed by its Bioconversion into 5-Methoxypodophyllotoxin β-D-Glucoside by Cell Cultures of Linum flavum. J. Nat. Prod. 1997, 60, 401-403.
    • (1997) J. Nat. Prod. , vol.60 , pp. 401-403
    • Van Uden, W.1    Bos, J.A.2    Boeke, G.M.3    Woerdenbag, H.J.4    Pras, N.5
  • 26
    • 0034583327 scopus 로고    scopus 로고
    • Nomenclature of Lignans and Neolignans
    • Moss, G. P. Nomenclature of Lignans and Neolignans. Pure Appl. Chem. 2000, 72, 1493-1523.
    • (2000) Pure Appl. Chem. , vol.72 , pp. 1493-1523
    • Moss, G.P.1
  • 29
    • 0028907152 scopus 로고
    • Research on Antibacterial and Antifungal Agents. XI. Synthesis and Antimicrobial Activity of N-heteroaryl Benzylamines and their Schiff Bases
    • Fioravanti, R.; Biava, M.; Porretta, G. C.; Landolfi, C.; Simonetti, N.; Villa, A.; Conte, E.; Porta-Puglia, A. Research on Antibacterial And Antifungal Agents. XI. Synthesis and Antimicrobial Activity of N-heteroaryl Benzylamines and their Schiff Bases. Eur. J. Med. Chem. 1995, 30, 123-132.
    • (1995) Eur. J. Med. Chem. , vol.30 , pp. 123-132
    • Fioravanti, R.1    Biava, M.2    Porretta, G.C.3    Landolfi, C.4    Simonetti, N.5    Villa, A.6    Conte, E.7    Porta-Puglia, A.8
  • 30
    • 0033516602 scopus 로고    scopus 로고
    • Solvent-free Synthesis of N-sulfonylimines Using Microwave Irradiation
    • Vass, A.; Dudás, J.; Varma, R. S. Solvent-free Synthesis of N-sulfonylimines Using Microwave Irradiation. Tetrahedron Lett. 1999, 40, 4951-4954.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 4951-4954
    • Vass, A.1    Dudás, J.2    Varma, R.S.3
  • 31
    • 0024231152 scopus 로고
    • A Simple Screening Method for the Quantitative Measurement of Cytotoxicity to Resting Primary Lymphocyte Cultures
    • (a) Faircloth, G. T.; Stewart, D.; Clement, J. J. A Simple Screening Method for the Quantitative Measurement of Cytotoxicity to Resting Primary Lymphocyte Cultures. J. Tiss. Cult. Methods 1988, 11, 201-205.
    • (1988) J. Tiss. Cult. Methods , vol.11 , pp. 201-205
    • Faircloth, G.T.1    Stewart, D.2    Clement, J.J.3
  • 33
    • 0028906786 scopus 로고
    • Some Practical Considerations and Applications of the National Cancer Institute In Vitro Anticancer Drug Discovery Screen
    • Boyd, M. R.; Paull, K. D.; Some Practical Considerations and Applications of the National Cancer Institute In Vitro Anticancer Drug Discovery Screen. Drug Dev. Res. 1995, 34, 91-109.
    • (1995) Drug Dev. Res. , vol.34 , pp. 91-109
    • Boyd, M.R.1    Paull, K.D.2
  • 34
    • 0029944528 scopus 로고    scopus 로고
    • Characterisation of Antimitotic Products from Marine Organisms that Disorganise the Microtubule Network: Ecteinascidin 743, Isohomohalichondrin-B and LL-15
    • García-Rocha, M.; García-Grávalos, M. D.; Avila, J. Characterisation of Antimitotic Products from Marine Organisms that Disorganise the Microtubule Network: Ecteinascidin 743, Isohomohalichondrin-B and LL-15. Br. J. Cancer 1996, 73, 875-883.
    • (1996) Br. J. Cancer , vol.73 , pp. 875-883
    • García-Rocha, M.1    García-Grávalos, M.D.2    Avila, J.3
  • 35
    • 0034657265 scopus 로고    scopus 로고
    • Induction of Apoptosis in Leukemic Cells by the Reversible Microtubule-Disrupting Agent 2-Methoxy-5-(2′, 3′, 4′-trimethoxyphenyl)-2, 4, 6- cycloheptatrien-1 -one: Protection by Bcl-2 and Bcl-X(L) and Cell Cycle Arrest
    • Gajate, C.; Barasoain, I.; Andreu, J. M.; Mollinedo, F. Induction of Apoptosis in Leukemic Cells by the Reversible Microtubule-Disrupting Agent 2-Methoxy-5-(2′, 3′, 4′-trimethoxyphenyl)-2, 4, 6- cycloheptatrien-1 -one: Protection by Bcl-2 and Bcl-X(L) and Cell Cycle Arrest. Cancer Res. 2000, 60, 2651-2659.
    • (2000) Cancer Res. , vol.60 , pp. 2651-2659
    • Gajate, C.1    Barasoain, I.2    Andreu, J.M.3    Mollinedo, F.4


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