Resveratrol analogue 3,4,4',5-tetramethoxystilbene inhibits growth, arrests cell cycle and induces apoptosis in ovarian SKOV-3 and A-2780 cancer cells

Toxicology and Applied Pharmacology

Volumn 263, Issue 1, 2012, Pages 53-60

  Piotrowska, Hanna ^a   Myszkowski, Krzysztof ^a   Ziółkowska, Alicja ^a   Kulcenty, Katarzyna ^a   Wierzchowski, Marcin ^a   Kaczmarek, Mariusz ^a   Murias, Marek ^a   Kwiatkowska Borowczyk, Eliza ^a,b   Jodynis Liebert, Jadwiga ^a  

^a POZNAN UNIVERSITY OF MEDICAL SCIENCES   (Poland)

^b GREATER POLAND CANCER CENTRE   (Poland)

Author keywords

3,4,4'5 tetramethoxystilbene; Apoptosis; Cell cycle; CYP1B1; Gene expression

Indexed keywords

3,3',4,4',5,5 HEXAMETHOXYSTILBENE; 3,4,4',5 TETRAMETHOXYSTILBENE; ANTINEOPLASTIC AGENT; CASPASE 3; CASPASE 7; CYTOCHROME P450 1A1; CYTOCHROME P450 1B1; DMU 212; MESSENGER RNA; RESVERATROL DERIVATIVE; STILBENE DERIVATIVE; UNCLASSIFIED DRUG;

APAF 1 GENE; APOPTOSIS; ARTICLE; BAX GENE; BCL 2110 GENE; BCL2 GENE; BIRC 2 GENE; CANCER CELL CULTURE; CELL CYCLE ARREST; CELL CYCLE G0 PHASE; CELL CYCLE G1 PHASE; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CONTROLLED STUDY; CYTOTOXICITY; DRUG MECHANISM; ENZYME ACTIVATION; FAS GENE; FASL GENE; GENE; GENE EXPRESSION; HUMAN; HUMAN CELL; NUCLEOTIDE SEQUENCE; P53 GENE; PROTEIN EXPRESSION; TNF GENE; TNFRSF10A GENE; TNFRSF16 GENE; TNFRSF21 GENE; TRAF 1 GENE; UPREGULATION;

ANTINEOPLASTIC AGENTS; APOPTOSIS; APOPTOTIC PROTEASE-ACTIVATING FACTOR 1; BCL-2-ASSOCIATED X PROTEIN; CELL CYCLE; CELL LINE, TUMOR; FEMALE; GENE EXPRESSION REGULATION, NEOPLASTIC; GENES, BCL-2; GENES, NEOPLASM; GENES, P53; HUMANS; OVARIAN NEOPLASMS; STILBENES;

EID: 84864145437     PISSN: 0041008X     EISSN: 10960333     Source Type: Journal    
DOI: 10.1016/j.taap.2012.05.023     Document Type: Article

References (42)

1. An Y.L., Nie F., Wang Z.Y., Zhang D.S. Preparation and characterization of realgar nanoparticles and their inhibitory effect on rat glioma cells. Int. J. Nanomedicine 2011, 6:3187-3194.
2. Androutsopoulos V.P., Ruparelia K.C., Papakyriakou A., Filippakis H., Tsatsakis A.M., Spandidos D.A. Anticancer effects of the metabolic products of the resveratrol analogue, DMU-212: structural requirements for potency. Eur. J. Med. Chem. 2011, 46:2586-2595.
3. Atten M.J., Godoy-Romero E., Attar B.M., Milson T., Zopel M., Holian O. Resveratrol regulates cellular PKC alpha and delta to inhibit growth and induce apoptosis in gastric cancer cells. Invest. New Drugs 2005, 23:111-119.
4. Bruno R.D., Njar V.C. Targeting cytochrome P450 enzymes: a new approach in anti-cancer drug development. Bioorg. Med. Chem. 2007, 15:5047-5060.
5. Chomczynski P., Sacchi N. Single-step method of RNA isolation by acid guanidiniumthiocyanate-phenol-chloroform extraction. Anal. Biochem. 1987, 162:156-159.
6. Chun Y.J., Lee S.K., Kim M.Y. Modulation of human cytochrome P450 1B1 expression by 2,4,3',5'-tetramethoxystilbene. Drug Metab. Dispos. 2005, 33:1771-1776.
7. Clement M.V., Hirpara J.L., Chawdhury S.H., Pervaiz S. Chemopreventive agent resveratrol, a natural product derived from grapes, triggers CD95 signaling-dependent apoptosis in human tumor cells. Blood 1998, 92:996-1002.
8. Debatin K.M. Apoptosis pathways in cancer and cancer therapy. Cancer Immunol. Immunother. 2004, 53:153-159.
9. Delmas D., Lancon A., Colin D., Jannin B., Latruffe N. Resveratrol as a chemopreventive agent: a promising molecule for fighting cancer. Curr. Drug Targets 2006, 7:423-442.
10. Eichhorst S.T., Muller M., Li-Weber M., Schulze-Bergkamen H., Angel P., Krammer P.H. A novel AP-1 element in the CD95 ligand promoter is required for induction of apoptosis in hepatocellular carcinoma cells upon treatment with anticancer drugs. Mol. Cell. Biol. 2000, 20:7826-7837.
11. Fulda S., Strauss G., Meyer E., Debatin K.M. Functional CD95 ligand and CD95 death-inducing signaling complex in activation-induced cell death and doxorubicin-induced apoptosis in leukemic T cells. Blood 2000, 95:301-308.
12. Fulda S., Meyer E., Friesen C., Susin S.A., Kroemer G., Debatin K.M. Cell type specific involvement of death receptor and mitochondrial pathways in drug-induced apoptosis. Oncogene 2001, 20:1063-1075.
13. Gaur U., Aggarwal B.B. Regulation of proliferation, survival and apoptosis by members of the TNF superfamily. Biochem. Pharmacol. 2003, 66:1403-1408.
14. Gibson P., Gill J.H., Khan P.A., Seargent J.M., Martin S.W., Batman P.A., Griffith J., Bradley C., Double J.A., Bibby M.C., Loadman P.M. Cytochrome P450 1B1 (CYP1B1) is overexpressed in human colon adenocarcinomas relative to normal colon: implications for drug development. Mol. Cancer Ther. 2003, 2:527-534.
15. Gosslau A., Chen M., Ho C.T., Chen K.Y. A methoxy derivative of resveratrol analogue selectively induced activation of the mitochondrial apoptotic pathway in transformed fibroblasts. Br. J. Cancer 2005, 92:513-521.
16. Guengerich P., Chun Y.J., Kim D., Gillam E.M., Shimada T. Cytochrome P450 1B1: a target for inhibition in anticarcinogenesis strategies. Mutat. Res. 2003, 523-524:173-182.
17. Hakem R., Hakem A., Duncan G.S., Henderson J.T., Woo M., Soengas M.S., Elia A., de la Pompa J.L., Kagi D., Khoo W., Potter J., Yoshida R., Kaufman S.A., Lowe S.W., Penninger J.M., Mak T.W. Differential requirement for caspase 9 in apoptotic pathways in vivo. Cell 1998, 94:339-352.
18. Herr I., Debatin K.M. Cellular stress response and apoptosis in cancer therapy. Blood 2001, 98:2603-2614.
19. Kaufmann S.H., Earnshaw W.C. Induction of apoptosis by cancer chemotherapy. Exp. Cell Res. 2000, 256:42-49.
20. Lee S.K., Nam K.A., Hoe Y.H., Min H.Y., Kim E.Y., Ko H., Song S., Lee T., Kim S. Synthesis and evaluation of cytotoxicity of stilbene analogues. Arch. Pharm. Res. 2003, 26:253-257.
21. Li H., Wu W.K., Zheng Z., Che C.T., Yu L., Li Z.J., Wu Y.C., Cheng K.W., Yu J., Cho C.H., Wang M. 2,3',4,4',5'-Pentamethoxy-trans-stilbene, a resveratrol derivative, is a potent inducer of apoptosis in colon cancer cells via targeting microtubules. Biochem. Pharmacol. 2009, 78:1224-1232.
22. Li H., Wu W.K., Li Z.J., Chan K.M., Wong C.C., Ye C.G., Yu L., Sung J.J., Cho C.H., Wang M. 2,3',4,4',5'-Pentamethoxy-trans-stilbene, a resveratrol derivative, inhibits colitis-associated colorectal carcinogenesis in mice. Br. J. Pharmacol. 2010, 60:1352-1361.
23. Ma Z., Molavi O., Haddadi A., Lai R., Gossage R.A., 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. 2008, 63:27-35.
24. McFadyen M.C., Melvin W.T., Murray G.I. Cytochrome P450 enzymes: novel options for cancer therapeutics. Mol. Cancer Ther. 2004, 3:363-371.
25. Murias M., Handler N., Erker T., Pleban K., Ecker G., Saiko P., Szekeres T., Jager W. Resveratrol analogues as selective cyclooxygenase-2 inhibitors: synthesis and structure-activity relationship. Bioorg. Med. Chem. 2004, 12:5571-5578.
26. Murray G.I., Taylor M.C., McFadyen M.C., McKay J.A., Greenlee W.F., Burke M.D., Melvin W.T. Tumor-specific expression of cytochrome P450 CYP1B1. Cancer Res. 1997, 57:3026-3031.
27. Park H., Aiyar S.E., Fan P., Wang J., Yue W., Okouneva T., Cox C., Jordan M.A., Demers L., Cho H., Kim S., Song R.X., Santen R.J. Effects of tetramethoxystilbene on hormone-resistant breast cancer cells: biological and biochemical mechanisms of action. Cancer Res. 2007, 67:5717-5726.
28. Piotrowska H., Kucinska M., Murias M. Biological activity of piceatannol: leaving the shadow of resveratrol. Mutat. Res. 2012, 750:60-82.
29. Potter G.A., Patterson L.H., Wanogho E., Perry P.J., Butler P.C., Ijaz T., Ruparelia K.C., Lamb J.H., Farmer P.B., Stanley L.A., Burke M.D. The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYP1B1. Br. J. Cancer 2002, 86:774-778.
30. Ramachandran C., Rodriguez S., Ramachandran R., Raveendran Nair P.K., Fonseca H., Khatib Z., Escalon E., Melnick S.J. Expression profiles of apoptotic genes induced by curcumin in human breast cancer and mammary epithelial cell lines. Anticancer Res. 2005, 25:3293-3302.
31. Roberti M., Pizzirani D., Simoni D., Rondanin R., Baruchello R., Bonora C., Buscemi F., Grimaudo S., Tolomeo M. Synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents. J. Med. Chem. 2003, 46:3546-3554.
32. Saiko P., Szakmary A., Jaeger W., Szekeres T. Resveratrol and its analogs: defense against cancer, coronary disease and neurodegenerative maladies or just a fad?. Mutat. Res. 2008, 658:68-94.
33. Sale S., Verschoyle R.D., Boocock D., Jones D.J., Wilsher N., Ruparelia K.C., Potter G.A., Farmer P.B., Steward W.P., Gescher A.J. 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 2004, 90:736-744.
34. Sale S., Tunstall R.G., Ruparelia K.C., Potter G.A., Steward W.P., Gescher A.J. Comparison of the effects of the chemopreventive agent resveratrol and its synthetic analog trans 3,4,5,4'-tetramethoxystilbene (DMU-212) on adenoma development in the Apc(Min+) mouse and cyclooxygenase-2 in human-derived colon cancer cells. Int. J. Cancer 2005, 115:194-201.
35. Su J.L., Lin M.T., Hong C.C., Chang C.C., Shiah S.G., Wu C.W., Chen S.T., Chau Y.P., Kuo M.L. Resveratrol induces FasL-related apoptosis through Cdc42 activation of ASK1/JNK-dependent signaling pathway in human leukemia HL-60 cells. Carcinogenesis 2005, 26:1-10.
36. Vousden K.H., Lu X. Live or let die: the cell's response to p53. Nat. Rev. Cancer 2002, 2:594-604.
37. Wahl H., Tan L., Griffith K., Choi M., Liu J.R. Curcumin enhances Apo2L/TRAIL-induced apoptosis in chemoresistant ovarian cancer cells. Gynecol. Oncol. 2007, 105:104-112.
38. Walle T., Hsieh F., DeLegge M.H., Oatis J.E., Walle U.K. High absorption but very low bioavailability of oral resveratrol in humans. Drug Metab. Dispos. 2004, 32:1377-1382.
39. Wang M., Jin Y., 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. 1999, 47:3974-3977.
40. Wu Y., Mehew J.W., Heckman C.A., Arcinas M., Boxer L.M. Negative regulation of bcl-2 expression by p53 in hematopoietic cells. Oncogene 2001, 20:240-251.
41. Yellepeddi V.K., Kumar A., Maher D.M., Chauhan S.C., Vangara K.K., Palakurthi S. Biotinylated PAMAM dendrimers for intracellular delivery of cisplatin to ovarian cancer: role of SMVT. Anticancer Res. 2011, 31:897-906.
42. Yoshida H., Kong Y.Y., Yoshida R., Elia A.J., Hakem A., Hakem R., Penninger J.M., Mak T.W. Apaf1 is required for mitochondrial pathways of apoptosis and brain development. Cell 1998, 94:739-750.