2,3′,4,4′,5′-Pentamethoxy-trans-stilbene, a resveratrol derivative, is a potent inducer of apoptosis in colon cancer cells via targeting microtubules

Biochemical Pharmacology

Volumn 78, Issue 9, 2009, Pages 1224-1232

  Li, Haitao ^a   Wu, William Ka Kei ^b   Zheng, Zongping ^a   Che, Chun Tao ^b   Yu, Le ^b   Li, Zhi Jie ^b   Wu, Ya Chun ^b   Cheng, Ka Wing ^a   Yu, Jun ^b   Cho, Chi Hin ^b   Wang, Mingfu ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

^b CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

Apoptosis; Colon cancer; Microtubule; Polymethoxystilbene; Resveratrol

Indexed keywords

2,3',4,4',5' PENTAMETHOXYSTILBENE; ANTINEOPLASTIC AGENT; CASPASE 3; CASPASE 7; CASPASE 8; CASPASE 9; DNA; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE; RESVERATROL; UNCLASSIFIED DRUG; 2,3',4,4',5'-PENTAMETHOXYSTILBENE; CASPASE; STILBENE DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL; CANCER CELL CULTURE; CANCER GROWTH; CANCER INHIBITION; CELL CYCLE ARREST; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CELL PROLIFERATION; CELL STRAIN CACO 2; CELL STRAIN HT29; CELL VIABILITY; COLON CANCER; CONTROLLED STUDY; DNA FRAGMENTATION; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; ENZYME ACTIVATION; ENZYME LINKED IMMUNOSORBENT ASSAY; FEMALE; FLOW CYTOMETRY; HUMAN; HUMAN CELL; IMMUNOFLUORESCENCE; IN VITRO STUDY; MICROTUBULE; MICROTUBULE ASSEMBLY; MITOSIS; MOUSE; NONHUMAN; PRIORITY JOURNAL; TUMOR XENOGRAFT; WESTERN BLOTTING; ANIMAL; CELL DIVISION; COLON TUMOR; DRUG EFFECT; ENZYMOLOGY; FLUORESCENT ANTIBODY TECHNIQUE; METABOLISM; NUDE MOUSE; PATHOLOGY; TUMOR CELL LINE;

ANIMALS; APOPTOSIS; BLOTTING, WESTERN; CASPASES; CELL DIVISION; CELL LINE, TUMOR; COLONIC NEOPLASMS; ENZYME ACTIVATION; ENZYME-LINKED IMMUNOSORBENT ASSAY; FLOW CYTOMETRY; FLUORESCENT ANTIBODY TECHNIQUE; G2 PHASE; HUMANS; MICE; MICE, NUDE; MICROTUBULES; POLY(ADP-RIBOSE) POLYMERASES; STILBENES;

EID: 70249113671     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2009.06.109     Document Type: Article

References (34)

1. Jemal A., Siegel R., Ward E., Hao Y., Xu J., Murray T., et al. Cancer statistics. CA Cancer J Clin 58 (2008) 71-96
2. Hanahan D., and Weinberg R.A. The hallmarks of cancer. Cell 100 (2000) 57-70
3. Jang M., Cai L., Udeani G.O., Slowing K.V., Thomas C.F., Beecher C.W., et al. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 275 (1997) 218-220
4. Wang M., Jin Y., and Ho C.T. Evaluation of resveratrol derivatives as potential antioxidants and identification of a reaction product of resveratrol and 2,2-diphenyl-1-picryhydrazyl radical. J Agric Food Chem 47 (1999) 3974-3977
5. Murias M., Handler N., Erker T., Pleban K., Ecker G., Saiko P., et al. Resveratrol analogues as selective cyclooxygenase-2 inhibitors: synthesis and structure-activity relationship. Bioorg Med Chem 12 (2004) 5571-5578
6. Murias M., Jager W., Handler N., Erker T., Horvath Z., Szekeres T., et al. Antioxidant, prooxidant and cytotoxic activity of hydroxylated resveratrol analogues: structure-activity relationship. Biochem Pharmacol 69 (2005) 903-912
7. Kim S., Ko H., Park J.E., Jung S., Lee S.K., and Chun Y.J. Design, synthesis, and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors. J Med Chem 45 (2002) 160-164
8. Robeti M., Pizziranti D., Simoni D., Rondanin R., Baruchello R., Bonora C., et al. Synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents. J Med Chem 46 (2003) 3546-3554
9. Sale S., Verschoyle R.D., Boocock D., Jones D.J.L., Wilsher N., Rupareliak C., et al. Pharmacokinetics in mice and growth-inhibitory properties of the putative cancer chemopreventive agent resveratrol and the synthetic analogue trans 3,4,5,4′-tetramethoxystilbene. Br J Cancer 90 (2004) 736-744
10. Min+ mouse and cyclooxygenase-2 in human-derived colon cancer cells. Int J Cancer 115 (2005) 194-201
11. Gosslau A., Chen M., Ho C.T., and Chen K.Y. A methoxy derivative of resveratrol analogue selectively induced activation of mitochondrial apoptotic pathway in transformed fibroblasts. Br J Cancer 92 (2005) 513-521
12. Lion C.J., Matthews C.S., Stevens M.F.G., and Westwell A.D. Synthesis, antitumor evaluation, and apoptosis-inducing activity of hydroxylated (E)-stilbenes. J Med Chem 48 (2005) 1292-1295
13. Simoni D., Romagnoli R., Baruchello R., Rondanin R., Rizzi M., Pavani M.G., et al. Novel combretastatin analogues endowed with antitumor activity. J Med Chem 49 (2006) 3143-3152
14. Park H., Aiyar S.E., Fan P., Wang J., Yue W., Okouneva T., et al. Effects of tetramethoxystilbene on hormone-resistant breast cancer cells: biological and biochemical mechanisms of action. Cancer Res 67 (2007) 5717-5726
15. Ma Z., Molavi O., Haddadi A., Lai R., Gossage R.A., and Lavasanifar A. Resveratrol analog trans 3,4,5,4′-tetramethoxystilbene (DMU-212) mediates anti-tumor effects via mechanism different from that of resveratrol. Cancer Chemother Pharmacol 63 (2008) 27-35
16. Shi Y. Mechanisms of caspase activation and inhibition during apoptosis. Mol Cell 9 (2002) 459-470
17. Degterev A., Boyce M., and Yan J. A decade of caspases. Oncogene 22 (2003) 8543-8567
18. Kroemer G., and Martin S.J. Caspase-independent cell death. Nat Med 11 (2005) 725-730
19. Kuwana T., and Newmeyer D.D. Bcl-2-family proteins and the role of mitochondria in apoptosis. Curr Opin Cell Biol 15 (2003) 691-699
20. Ruvolo P.P., Deng X., and May W.S. Phosphorylation of Bcl-2 and regulation of apoptosis. Leukemia 15 (2001) 515-522
21. Srivastava R.K., Srivastava A.R., Korsmeyer S.J., Nesterova M., Cho-Chung Y.S., and Longo D.L. Involvement of microtubules in the regulation of Bcl-2 phosphorylation and apoptosis through cyclic AMP-dependent protein kinase. Mol Cell Biol 18 (1998) 3509-3517
22. Furukawa Y., Iwase S., Kikuchi J., Terui Y., Nakamura M., Yamada H., et al. Phosphorylation of Bcl-2 protein by CDC2 kinase during G2/M phases and its role in cell cycle regulation. J Biol Chem 275 (2000) 21661-21667
23. Mollinedo F., and Gajate C. Microtubules, microtubule-interfering agents and apoptosis. Apoptosis 8 (2003) 413-450
24. Datta S.R., Ranger A.M., Lin M.Z., Sturgill J.F., Ma Y.C., Cowan C.W., et al. Survival factor-mediated BAD phosphorylation raises the mitochondrial threshold for apoptosis. Dev Cell 3 (2002) 631-643
25. Pumiglia K.M., and Decker S.J. Cell cycle arrest mediated by the MEK/mitogen-activated protein kinase pathway. Pro Natl Acad Sci USA 94 (1997) 448-452
26. Mcdaid H.M., and Horwitz S.B. Selective potentiation of paclitaxel(taxol)-induced cell death by mitogen-activated protein kinase inhibition in human cancer cell lines. Mol Pharmacol 60 (2001) 290-301
27. Fan M., Goodwin M., Vu T., Brantley F.C., Gaarde W.A., and Chambers T.C. Vinblastine-induced phosphorylation of Bcl-2 and Bcl-xL is mediated by JNK and occurs in parallel with inactivation of the Raf-1/MEK/ERK cascade. J Biol Chem 275 (2000) 29980-29985
28. Konishi Y., Lehtinen M., Donovan N., and Bonni A. Cdc2 phosphorylation of BAD links the cell cycle to the cell death machinery. Mol Cell 9 (2002) 1005-1016
29. Tseng C.J., Wang Y.J., Liang Y.C., Jeng J.H., Lee W.S., Lin J.K., et al. Microtubule damaging agents induced apoptosis in HL60 cells and G2/M cell cycle arrest in HT-29 cells. Toxicology 175 (2002) 123-142
30. Lei K., and Davis R.J. JNK phosphorylation of Bim-related members of the Bcl2 family induces Bax-dependent apoptosis. Pro Natl Acad Sci USA 100 (2003) 2432-2437
31. Goncalves A., Braguer D., Carles G., Andre N., Prevot C., and Briand C. Caspase-8 activation independent of CD95/CD95-L interaction during paclitaxel-induced apoptosis in human colon cancer (HT29-D4). Biochem Pharmacol 60 (2000) 1579-1584
32. Haefen C.V., Wieder T., Essmann F., Schulze O.K., Dorken B., and Daniel P.T. Paclitaxel-induced apoptosis in BJAB cells proceeds via a death receptor-independent, caspase-3/-8-driven mitochondrial amplification loop. Oncogene 22 (2003) 2236-2247
33. Cushman M., Nagarathnam D., Gopal D., He H.M., Lin C.M., and Hamel E. Synthesis and evaluation of analogues of (Z)-1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl) ethene as potential cytotoxic and antimitotic agents. J Med Chem 35 (1992) 2293-2306
34. Jordan M.A., and Wilson L. Microtubules as a target for anticancer drugs. Nat Rev Cancer 4 (2004) 253-265