Cytotoxicity, apoptosis induction, and mitotic arrest by a novel podophyllotoxin glucoside, 4DPG, in tumor cells

Acta Pharmacologica Sinica

Volumn 26, Issue 8, 2005, Pages 1000-1008

  Qi, Yi Lin ^a   Liao, Fan ^a   Zhao, Chang Qi ^a   Lin, Yong Da ^a   Zuo, Ming Xue ^a,b  

^a BEIJING NORMAL UNIVERSITY   (China)

^b Key Laboratory for Molecular Biology and Gene Engineering Drugs of Beijing   (China)

Author keywords

4 demethyl picropodophyllotoxin 7 O D glucopyranoside; Apoptosis; Flow cytometry; Microtubulin; Podophyllotoxin

Indexed keywords

3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; 4 NORPICROPODOPHYLLOTOXIN 4' O BETA DEXTRO GLUCOPYRANOSIDE; CASPASE 3; ETOPOSIDE; PODOPHYLLOTOXIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CELL CYCLE; CELL PROLIFERATION; CYTOSKELETON; CYTOTOXICITY; DOSE RESPONSE; DRUG POTENCY; DRUG STRUCTURE; ENZYME ACTIVATION; HELA CELL; HUMAN; HUMAN CELL; IC 50; IMMUNOCYTOCHEMISTRY; MICROTUBULE ASSEMBLY; MITOSIS INHIBITION;

APOPTOSIS; CASPASE 3; CASPASES; CELL DIVISION; CELL LINE, TUMOR; CELL NUCLEUS; CELL PROLIFERATION; DNA FRAGMENTATION; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME ACTIVATION; GLUCOSIDES; HELA CELLS; HUMANS; K562 CELLS; MICROSCOPY, ELECTRON, TRANSMISSION; MICROTUBULES; MOLECULAR STRUCTURE; PODOPHYLLOTOXIN; POLYMERS; TIME FACTORS;

EID: 23844489439     PISSN: 16714083     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1745-7254.2005.00148.x     Document Type: Article

References (38)

1. Mukherjee AK, Basu S, Sarkar N, Ghosh AC. Advances in cancer therapy with plant based natural products. Curr Med Chem 2001; 8: 1467-86.
2. Tsai TH. Analytical approaches for traditional Chinese medicines exhibiting antineoplastic activity. J Chromatogr B Biomed Sci Appl 2001; 764: 27-48.
3. Lee KH. Novel antitumor agents from higher plants. Med Res Rev 1999; 19: 569-96.
4. Imbert F. Discovery of podophyllotoxins. Biochimie 1998; 80: 207-22.
5. Cortese F, Bhattacharyya B, Wolf J. Podophyllotoxin as a probe for the colchicine binding site of tubulin. J Biol Chem 1977; 252: 1134-40.
6. Sackett DL. Podophyllotoxin, steganacin and combretastatin: natural products that bind at the colchicine site of tubulin. Pharmacol Ther 1993; 59: 163-228.
7. ter Haar E, Rosenkranz HS, Hamel E, Day BW. Computational and molecular modeling evaluation of the structural basis for tubulin polymerization inhibition by colchicine site agents. Bioorg Med Chem 1996; 4: 1659-71.
8. Desbene S, Giorgi-Renault S. Drugs that inhibit tubulin polymerization: the particular case of podophyllotoxin and analogues. Curr Med Chem Anti-Canc Agents 2002; 2: 71-90.
9. Gordaliza M, Castro MA, del Corral JM, Feliciano AS. Antitumor properties of podophyllotoxin and related compounds. Curr Pharm Des 2000; 6: 1811-39.
10. Gordaliza M, Garcia PA, del Corral JM, Castro MA, Gomez-Zurita MA. Podophyllotoxin: distribution, sources, applications and new cytotoxic derivatives. Toxicon 2004; 44: 441-59.
11. Kelleher JK. Correlation of tubulin-binding and antitumor activities of podophyllotoxin analogs. Cancer Treat Rep 1978; 62: 1443-7.
12. Hainsworth JD, Greco FA. Etoposide: twenty years later. Ann Oncol 1995; 6: 325-41.
13. Schacter L. Etoposide phosphate: what, why, where, and how? Semin Oncol 1996; 23 (Suppl 13): 1-7.
14. Evans WK, Eisenhauer E, Hughes P, Maroun JA, Ayoub J, Shepherd FA, et al. VP-16 and carboplatin in previously untreated patients with extensive small cell lung cancer: a study of the National Cancer Institute of Canada Clinical Trials Group. Br J Cancer 1988; 58: 464-8.
15. Splinter T, Kok T, Kho S, Lameris H, ten Kate F, Dalesio O, et al. A multicenter phase II trial of cisplatin and oral etoposide (VP-16) in inoperable non-small-cell lung cancer. Semin Oncol 1986; 13 (Suppl 3): 97-103.
16. Aisner J, Lee EJ. Etoposide. Current and future status. Cancer 1991; 67 (Suppl 1): 215-9.
17. Hande KR. Etoposide pharmacology. Semin Oncol 1992; 19 (Suppl 13): 3-9.
18. Minocha A, Long BH. Inhibition of the DNA catenation activity of type II topoisomerase by VP16-213 and VM26. Biochem Biophys Res Commun 1984; 122: 165-70.
19. Tewey KM, Chen GL, Nelson EM, Liu LF. Intercalative antitumor drugs interfere with the breakage-reunion reaction of mammalian DNA topoisomerase II. J Biol Chem 1984; 259: 9182-7.
20. Long BH and Stringfellow DA. Inhibitors of topoisomerase II: structure-activity relationships and mechanism of action of podophyllin congeners. Adv Enzyme Regul 1988; 27: 223-56.
21. Long BH. Mechanisms of action of teniposide (VM-26) and comparison with etoposide (VP-16). Semin Oncol 1992; 19 (Suppl 6): 3-19.
22. Long BH, Musial ST, Brattain MG. Comparison of cytotoxicity and DNA breakage activity of congeners of podophyllotoxin including VP16-213 and VM26: a quantitative structure-activity relationship. Biochemistry 1984; 23: 1188-94.
23. Paulson JC, McClure WO. Microtubules and axoplasmic transport. Inhibition of transport by podophyllotoxin: an interaction with microtubule protein. J Cell Biol 1975; 67: 461-7.
24. Loike JD, Brewer CF, Sternlicht H, Gensler WJ, Horwitz SB. Structure-activity study of the inhibition of microtubule assembly in vitro by podophyllotoxin and its congeners. Cancer Res 1978; 38: 2688-93.
25. Bedows E, Hatfield GM. An investigation of the antiviral activity of Podophyllum peltatum. J Nat Prod 1982; 45: 725-9.
26. Davis RE, Schlumpf BE, Klinger PD. Comparative neurotoxicity of tubulin-binding drugs: inhibition of goldfish optic nerve regeneration. Toxicol Appl Pharmacol 1985; 80: 308-15.
27. Roulland E, Magiatis P, Arimondo P, Bertounesque E, Monneret C. Hemi-synthesis and biological activity of new analogues of podophyllotoxin. Bioorg Med Chem 2002; 10: 3463-71.
28. Girnita A, Girnita L, del Prete F, Bartolazzi A, Larsson O, Axelson M. Cyclolignans as inhibitors of the insulin-like growth factor-1 receptor and malignant cell growth. Cancer Res 2004; 64: 236-42.
29. Vasilcanu D, Girnita A, Girnita L, Vasilcanu R, Axelson M, Larsson O. The cyclolignan PPP induces activation loop-specific inhibition of tyrosine phosphorylation of the insulin-like growth factor-1 receptor. Link to the phosphatidyl inositol-3 kinase/Akt apoptotic pathway. Oncogene 2004; 23: 7854-62.
30. Zhao C, Huang J, Hagatsu A, Ogihara Y. Two new podophyllotoxin glucosides from Sinopodophyllum emodi (Wall) Ying. Chem Pharm Bull 2001; 49: 773-5.
31. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983; 65: 55-63.
32. Gundersen GG, Cook TA. Microtubules and signal transduction. Curr Opin Cell Biol 1999; 11: 81-94.
33. Miller KD, Sledge GW Jr. Taxanes in the treatment of breast cancer: a prodigy comes of age. Cancer Invest 1999; 17: 121-36.
34. Mollinedo F, Gajate C. Microtubules, microtubule-interfering agents and apoptosis. Apoptosis 2003; 8: 413-50.
35. Jordan MA, Wendell K, Gardiner S, Derry WB, Copp H, Wilson L. Mitotic block induced in HeLa cells by low concentrations of paclitaxel (Taxol) results in abnormal mitotic exit and apoptotic cell death. Cancer Res 1996; 56: 816-25.
36. Tseng CJ, Wang YJ, Liang YC, Jeng JH, Lee WS, Lin JK, et al. Microtubule damaging agents induce apoptosis in HL60 cells and G2/M cell cycle arrest in HT29 cells. Toxicology 2002; 175: 123-42.
37. Wang LG, Liu XM, Kreis W, Budman DR. The effect of antimicrotubule agents on signal transduction pathways of apoptosis: a review. Cancer Chemother Pharmacol 1999; 44: 355-61.
38. Bhalla KN. Microtubule-targeted anticancer agents and apoptosis. Oncogene 2003; 22: 9075-86.