The resveratrol analogue 4,4′-dihydroxy-trans-stilbene inhibits cell proliferation with higher efficiency but different mechanism from resveratrol

International Journal of Biochemistry and Cell Biology

Volumn 41, Issue 12, 2009, Pages 2493-2502

  Savio, M ^a   Coppa, T ^a   Bianchi, L ^a   Vannini, V ^a   Maga, G ^b   Forti, L ^c   Cazzalini, O ^a   Lazze M C ^a   Perucca, P ^a   Prosperi, E ^b   Stivala, L A ^a  

^a UNIVERSITY OF PAVIA   (Italy)

^b CNR   (Italy)

^c UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

Author keywords

4,4 Dihydroxy trans stilbene; Cell proliferation; DNA polymerases; DNA synthesis; Resveratrol

Indexed keywords

4,4' DIHYDROXY TRANS STILBENE; CHECKPOINT KINASE 1; CYCLIN DEPENDENT KINASE INHIBITOR 1A; DNA DIRECTED DNA POLYMERASE DELTA; MINICHROMOSOME MAINTENANCE PROTEIN 2; PROTEIN P53; RESVERATROL; STILBENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CELL CYCLE ARREST; CELL CYCLE G1 PHASE; CELL CYCLE PROGRESSION; CELL CYCLE REGULATION; CELL CYCLE S PHASE; CELL PROLIFERATION; CELL SURVIVAL; CLONOGENESIS; CONCENTRATION RESPONSE; CONTROLLED STUDY; DNA REPLICATION; DNA SYNTHESIS; DRUG CYTOTOXICITY; DRUG EFFICACY; DRUG MECHANISM; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; FIBROBLAST CULTURE; GROWTH INHIBITION; HUMAN; HUMAN CELL; IN VITRO STUDY; NULL CELL; PROTEIN EXPRESSION; PROTEIN PHOSPHORYLATION; STRUCTURE ACTIVITY RELATION;

CELL CYCLE; CELL CYCLE PROTEINS; CELL LINE; CELL PROLIFERATION; CHROMATIN ASSEMBLY AND DISASSEMBLY; DNA POLYMERASE III; FIBROBLASTS; HUMANS; LUNG; OLIGONUCLEOTIDE ARRAY SEQUENCE ANALYSIS; PROTEIN CONFORMATION; STILBENES; VITIS; WINE;

VITACEAE;

EID: 70350346843     PISSN: 13572725     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.biocel.2009.08.005     Document Type: Article

References (50)

1. Alessi F., Quarta S., Savio M., Riva F., Rossi L., Stivala L.A., et al. The cyclin-dependent kinase inhibitors Olomoucine and Roscovitine arrest human fibroblasts in G1 phase by specific inhibition of CDK2 kinase activity. Exp Cell Res 245 (1998) 8-18
2. Arichi H., Kimura Y., Okuda H., Baba K., Kozawa M., and Arichi S. Effects of stilbene components of the roots of Polygonum cuspidatum on lipid metabolism. Chem Pharm Bull 30 (1982) 1766-1770
3. Balan K.V., Wang Y., Chen S.W., Chen J.C., Zheng L.F., Yang L., et al. Proteasome-independent down-regulation of estrogen receptor-alpha (ERalpha) in breast cancer cells treated with 4,4'-dihydroxy-trans-stilbene. Biochem Pharmacol 72 (2006) 573-581
4. Barger J.L., Kayo T., Vann J.M., Arias E.B., Wang J., Hacker T.A., et al. A low dose of dietary resveratrol partially mimics caloric restriction and retards aging parameters in mice. PLoS ONE 3 6 (2008) e2264
5. Bauer J.A., and Sinclair D.A. Therapeutic potential of resveratrol: the in vivo evidence. Nat Rev 5 (2006) 493-506
6. Baur J.A., Pearson K.J., Price N.L., Jamieson H.A., Lerin C., Kalra A., et al. Resveratrol improves health and survival of mice on a high-calorie diet. Nature 16 444(7117) (2006) 337-342
7. Billack B., Radkar V., and Adiabouah C. In vitro evaluation of the cytotoxic and antiproliferative properties of resveratrol and several of its analogs. Cell Mol Biol Lett 13 (2008) 553-569
8. Brown J.P., Weiw W., and Sedivy J.M. Bypass of senescence after disruption of p21cip/waf gene in normal diploid human fibroblasts. Science 277 (1997) 831-834
9. Cai Y.J., Fang J.G., Ma L.P., Yang L., and Liu Z.L. Inhibition of free radical-induced peroxidation of rat liver microsomes by resveratrol and its analogues. Biochim Biophys Acta 1637 (2003) 31-38
10. Cheng J.C., Fang J.G., Chen W.F., Zhou B., Yang L., and Liu Z.L. Structure-activity relationship studies of resveratrol and its analogues by the reaction kinetics of low density lipoprotein peroxidation. Bioorg Chem 34 (2006) 142-157
11. Ebara M., Fukuda H., Hatano R., Saisho H., Nagato Y., Suzuki K., et al. Relationship between copper, zinc and metallothionein in hepatocellular carcinoma and its surrounding liver parenchyma. J Hepatol 33 (2000) 415-422
12. Fan G.J., Liu X.D., Qian Y.P., Shang Y.J., Li X.Z., Dai F., Fang J.G., Jin X.L., and Zhou B. 4,4′-dihydroxy-trans-stilbene, a resveratrol analogue, exhibited enhanced antioxidant activity and cytotoxicity. Bioorg Med Chem 17 (2009) 2360-2365
13. Fang H., Tong W., Shi L.M., Blair R., Perkins R., Branham W., et al. Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens. Chem Res Toxicol 14 (2001) 280-294
14. Fang J.G., Lu M., Chen Z.H., Zhu H.H., Li Y., Yang L., et al. Antioxidant effects of resveratrol and its analogues against the free-radical-induced peroxidation of linoleic acid in micelles. Chemistry 8 (2002) 4191-4198
15. Fontecave M., Lepoivre M., Elleingand E., Gerez C., and Guittet O. Resveratrol, a remarkable inhibitor of ribonucleotide reductase. FEBS Lett 412 (1998) 277-279
16. Frankel E.N., Waterhouse A.L., and Kinsella J.E. Inhibition of human LDL oxidation by resveratrol. Lancet 341 (1993) 1103-1104
17. Goldberg D.M., Hahn S.E., and Parkes J.G. Beyond alcohol: beverage consumption and cardiovascular mortality. Clin Chem Acta 237 (1995) 155-187
18. Hadi S.M., Bhat S.H., Azmi A.S., Hanif S., Shamim U., and Ullah M.F. Oxidative breakage of cellular DNA by plant polyphenols: a putative mechanism for anticancer properties. Semin Cancer Biol 17 (2007) 370-376
19. Hain R., Bieseler B., Kindl H., Schroder G., and Stocker R. Expression of a stilbene synthase gene in Nicotiana tabacum results in synthesis of the phytoalexin resveratrol. Plant Mol Biol 15 (1990) 325-335
20. Howitz K.T., Bitterman K.J., Cohen H.Y., Lamming D.W., Lavu S., Wood J.G., et al. Small molecule activators of sirtuins extended Saccharomyces cerevisiae lifespan. Nature 425 (2003) 191-196
21. Hsieh T., Juan G., Darzynkiewicz Z., and Wu J.M. Resveratrol increases nitric oxide synthase, induces accumulation of p53 and p21waf1/cip1 and suppresses bovine pulmonary artery endothelial cell proliferation by perturbing progression through S and G2. Cancer Res 59 (1999) 2596-2601
22. Hsieh T., and Wu J.M. Differential effects on growth, cell cycle arrest, and induction of apoptosis by resveratrol in human prostate cancer cell lines. Exp Cell Res 249 (1999) 109-115
23. Hsieh T.C., Burfeind P., Laud K., Bacher J.M., Traganos F., Darzynkiewicz Z., et al. Cell cycle effects and control of gene expression by resveratrol in human breast carcinoma cell lines with different metastatic potentials. Int J Oncol 15 (1999) 245-252
24. Hudson T.S., Hartle D.K., Hursting S.D., Nunez N.P., Wang T.T.Y., and Young H.A. Inhibition of prostate cancer growth by muscadine grape skin extract and resveratrol through distinct mechanisms. Cancer Res 67 (2007) 8396-8405
25. Jang D.S., Kang B.S., Ryu S.Y., Chang I.M., Min K.R., and Kim Y. Inhibitory effects of resveratrol analogs on unopsonized zymosan-induced oxygen radical production. Biochem Pharmacol 57 (1999) 705-712
26. Jang M., Cai L., Udeani G.O., Slowing K.V., Thomas C.F., Beecher C.W.W., et al. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 275 (1997) 218-220
27. Kerry N.L., and Abbey M. Red wine and fractionated phenolic compounds prepared from red wine inhibit low density lipoprotein oxidation in vitro. Atherosclerosis 135 (1997) 93-102
28. Kimura Y., Okuda H., and Arichi S. Effects of stilbenes on arachidonate metabolism in leukocytes. Biochim Biophys Acta 834 (1985) 275-278
29. Klinge C.M., Wickramasinghe N.S., Ivanova M.M., and Dougherty S.M. Resveratrol stimulates nitric oxide production by increasing estrogen receptor alpha-Src-caveolin-1 interaction and phosphorylation in human umbilical vein endothelial cells. FASEB J 22 (2008) 2185-2197
30. Kotha A., Sekharam M., Cilenti L., Siddiquee K., Khaled A., Zervos A.S., et al. Resveratrol inhibits Src and Stat3 signaling and induces the apoptosis of malignant cells containing activated Stat3 protein. Mol Cancer Ther 5 (2006) 621-629
31. Krude T. Initiation of human DNA replication in vitro using nuclei from cells arrested at an initiation-competent state. J Biol Chem 275 (2000) 13699-13707
32. Langcake P., and Pryce R.J. A new class of phytoalexins from grapevines. Experientia 33 (1977) 151-152
33. Li J.M., and Brooks G. Cell cycle regulatory molecules (cyclins, cyclin-dependent kinases and cyclin-dependent kinase inhibitors) and the cardiovascular system. Eur Heart J 20 (1999) 406-420
34. Locatelli G.A., Savio M., Forti L., Shevelev I., Ramadan K., Stivala L.A., et al. Inhibition of mammalian DNA polymerases by resveratrol: mechanism and structural determinants. Biochem J 389 (2005) 259-268
35. MacCarrone M., Lorenzon T., Guerrieri P., and Finazzi Agrò A. Resveratrol prevents apoptosis in K562 cells by inhibiting lipoxygenase and cyclooxygenase activity. Eur J Biochem 265 (1999) 27-34
36. Meeran S.M., and Katiyar S.K. Cell cycle control as a basis for cancer chemoprevention through dietary agents. Front Biosci 13 (2008) 2191-2202
37. Mgbonyebi O.P., Russo J., and Russo I.H. Antiproliferative effect of synthetic resveratrol on human breast epithelial cells. Int J Oncol 12 (1998) 865-869
38. Milne J.C., Lambert P.D., Schenk S., Carney D.P., Smith J.J., Gagne D.J., et al. Small molecule activators of SIRT1 as therapeutics for the treatment of type 2 diabetes. Nature 450 (2007) 712-716
39. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol 65 (1983) 55-63
40. Pace-Asciak C.R., Hahn S., Diamandis E.P., Soleas G., and Goldberg D.M. The red wine phenolics trans-resveratrol and quercetin block human platelet aggregation and eicosanoid synthesis: implications for protection against coronary heart disease. Clin Chim Acta 235 (1995) 207-219
41. Pace-Asciak C.R., Rounova O., Hahn S., Diamandis E.P., and Goldberg D.M. Wines and grape juices as modulators of platelet aggregation in healthy human subjects. Clin Chim Acta 246 (1996) 163-182
42. Pervaiz S. Resveratrol: from grapevines to mammalian biology. FASEB J 17 (2003) 1975-1985
43. Rotondo S., Rajtar G., Manarini S., Celardo A., Rotilio D., de Gaetano G., et al. Effect of trans-resveratrol, a natural polyphenolic compound, on human polymorphonuclear leukocyte function. Brit J Pharmacol 123 (1998) 1691-1699
44. Scovassi A.I., and Prosperi E. Analysis of proliferating cell nuclear antigen (PCNA) associated with DNA excision repair sites in mammalian cells. Methods Mol Biol 314 (2006) 457-475
45. Soleas G.J., Diamandis E.P., and Goldberg D.M. Resveratrol: a molecule whose time has come? And gone?. Clin Biochem 30 (1997) 91-113
46. Stivala L.A., Savio M., Carafoli F., Perucca P., Bianchi L., Maga G., et al. Specific structural determinants are responsible for the antioxidant activity and the cell cycle effects of resveratrol. J Biol Chem 276 (2001) 22586-22594
47. Sun N.J., Woo S.H., Cassady J.M., and Snapka R.M. DNA polymerase and topoisomerase II inhibitors from Psoralea corylifolia. J Nat Prod 61 (1998) 362-366
48. Szewczuk L.M., Forti L., Stivala L.A., and Penning T.M. Resveratrol is a peroxidase-mediated inactivator of COX-1 but not COX-2: a mechanistic approach to the design of COX-1 selective agents. J Biol Chem 279 21 (2004) 22727-22737
49. Zeisel S.H., and Salganik R.I. Antioxidants and nutrition support. Curr Opin Clin Nutr Metab Care 2 (1999) 1-3
50. Zheng L.F., Wei Q.Y., Cai Y.J., Fang J.G., Zhou B., Yang L., and Liu Z.L. DNA damage induced by resveratrol and its synthetic analogues in the presence of Cu (II) ions: mechanism and structure-activity relationship. Free Radic Biol Med 41 (2006) 1807-1816