Chemopreventive effects of resveratrol and resveratrol derivatives

Annals of the New York Academy of Sciences

Volumn 1215, Issue 1, 2011, Pages 89-95

  Szekeres, Thomas ^a   Saiko, Philipp ^a   Fritzer Szekeres, Monika ^a   Djavan, Bob ^b   Jäger, Walter ^c  

^a MEDICAL UNIVERSITY OF VIENNA   (Austria)

^b NEW YORK UNIVERSITY   (United States)

^c UNIVERSITY OF VIENNA   (Austria)

Author keywords

Antitumor effects; Free radicals; Melanoma; Polyhydroxyphenols; Resveratrol; Resveratrol metabolism; Ribonucleotide reductase

Indexed keywords

ACETYLSALICYLIC ACID; CELECOXIB; CYCLOOXYGENASE 2; CYTARABINE; DACARBAZINE; DRUG ANALOG; HEXAHYDROXYSTILBENE; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; KI 67 ANTIGEN; PICEATANNOL; PROSTAGLANDIN SYNTHASE; PROTEIN BCL 2; RESVERATROL; RIBONUCLEOTIDE REDUCTASE; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; CANCER CELL; CANCER CHEMOTHERAPY; CANCER PREVENTION; CELL DEATH; CELL LINE; CHEMOPROPHYLAXIS; DNA SYNTHESIS INHIBITION; DRUG BIOAVAILABILITY; DRUG EFFECT; DRUG METABOLISM; DRUG POTENTIATION; ENZYME ACTIVITY; ENZYME INHIBITION; GROWTH INHIBITION; HUMAN; IC 50; IN VITRO STUDY; IN VIVO STUDY; INFLAMMATION; INHIBITION KINETICS; LYMPH NODE METASTASIS; MELANOMA; NEOPLASM; NONHUMAN; PHASE 3 CLINICAL TRIAL (TOPIC); TREATMENT DURATION; TUMOR GROWTH; XENOTRANSPLANTATION;

EID: 78851469962     PISSN: 00778923     EISSN: 17496632     Source Type: Book Series    
DOI: 10.1111/j.1749-6632.2010.05864.x     Document Type: Article

References (30)

1. Renaud, S. & M. de Lorgeril 1992. Wine, alcohol, platelets, and the French paradox for coronary heart disease. Lancet. 339: 1523-1526.
2. Pace-Asciak C.R., S. Hahn, E.P. Diamandis, et al 1995. 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: 207-219.
3. Frankel E.N., A.L. Waterhouse & J.E. Kinsella 1993. Inhibition of human LDL oxidation by resveratrol. Lancet. 341: 1103-1104.
4. Huang C., W.Y. Ma, A. Goranson, et al 1999. Resveratrol suppresses cell transformation and induces apoptosis through a p53-dependent pathway. Carcinogenesis 20: 237-242.
5. Potter G.A., L.H. Patterson, E. Wanogho, et al 2002. The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYP1B1. Br. J. Cancer. 86: 774-778.
6. Szekeres T., K. Gharehbaghi, M. Fritzer, et al 1994. Biochemical and antitumor activity of trimidox, a new inhibitor of ribonucleotide reductase. Cancer Chemother. Pharmacol. 34: 63-66.
7. Elford H.L., M. Freese, E. Passamani, et al 1970. Ribonucleotide reductase and cellproliferation. I. Variations of ribonucleotide reductase activity with tumor growth rate in a series of rat hepatomas. J. Biol. Chem. 245: 5228-5233.
8. Elford, HL, G.L. Wampler & B. van't Riet 1979. New ribonucleotide reductase inhibitors with antineoplastic activity. Cancer Res. 39: 844-851.
9. Fontecave, M., M. Lepoivre, E. Elleingand, et al 1998. Resveratrol, a remarkable inhibitor of ribonucleotide reductase. FEBS Lett. 421: 277-279.
10. Boocock, D.J., G.E. Faust, K.R. Patel, et al 2007. Phase I dose escalation pharmacokinetic study in healthy volunteers of resveratrol, a potential cancer chemopreventive agent. Cancer Epidemiol. Biomarkers Prev. 16: 1246-1252.
11. Burkon, A. & V. Somoza 2008. Quantification of free and protein-bound trans-resveratrol metabolites and identification of trans-resveratrol-C/O-conjugated diglucuronides-two novel resveratrol metabolites in human plasma. Mol. Nutr. Food Res. 52: 549-557.
12. Maier-Salamon, A., B. Hagenauer, M. Wirth, et al 2006. Increased transport of resveratrol across monolayers of the human intestinal Caco-2 cells is mediated by inhibition and saturation of metabolites. Pharm. Res. 23: 2107-21015.
13. Maier-Salamon, A., B. Hagenauer, G. Reznicek, et al 2008. Metabolism and disposition of resveratrol in the isolated perfused rat liver: role of Mrp2 in the biliary excretion of glucuronides. J. Pharm. Sci. 97: 1615-1628.
14. 14C]-trans-resveratrol, a cancer chemopreventive polyphenol, in mouse tissues after oral administration. Life Sci. 72: 2219-2233.
15. Hoshino, J., E.J. Park, T.P Kondratyuk, et al 2010. Selective synthesis and biological evaluation of sulfate-conjugated resveratrol metabolites. J. Med. Chem. 53: 5033-5043.
16. Calamini, B., K. Ratia, M.G. Malkowski, et al 2010. Pleiotropic mechanisms facilitated by resveratrol and its metabolites. Biochem. J. 429: 273-282.
17. Mikulski, D. & M. Molski 2010. Quantitative structure-antioxidant activity relationship of trans-resveratrol oligomers, trans-4, 4'-dihydroxystilbene dimer, trans-resveratrol-3-O-glucuronide, glucosides: trans-piceid, cis-piceid, trans-astringin and trans-resveratrol-4'-O-beta-D-glucopyranoside. Eur. J. Med. Chem. 45: 2366-2380.
18. Murias, M., N. Handler, T. Erker, et al 2004. Resveratrol analogues as selective cyclooxygenase-2 inhibitors: synthesis and structure-activity relationship. Bioorg. Med. Chem. 12: 5571-5578.
19. Murias, M., W. Jäger, N. Handler, et al 2005. Antioxidant, prooxidant and cytotoxic activity of hydroxylated resveratrol analogues: structure-activity relationship. Biochem. Pharmacol. 69: 903-912.
20. Miksits, M., K. Wlcek, M. Svoboda, et al 2009. Antitumor activity of resveratrol and its sulfated metabolites against human breast cancer cells. Planta Med. 75: 1227-1230.
21. Bader, Y., S. Madlener, S. Strasser, et al 2008. Stilbene analogues affect cell cycle progression and apoptosis independently of each other in an MCF-7 array of clones with distinct genetic and chemoresistant backgrounds. Oncol. Rep. 19: 801-810.
22. Saiko, P., M. Pemberger, Z. Horvath, et al 2008. Novel resveratrol analogs induce apoptosis and cause cell cycle arrest in HT29 human colon cancer cells: inhibition of ribonucleotide reductase activity. Oncol. Rep. 19: 1621-1626.
23. Fritzer-Szekeres, M., I. Savinc, Z. Horvath, et al 2008. Biochemical effects of piceatannol in human HL-60 promyelocytic leukemia cells-synergism with Ara-C. Int. J. Oncol. 33: 887-8892.
24. Horvath, Z., S. Marihart-Fazekas, P. Saiko, et al 2007. Novel resveratrol derivatives induce apoptosis and cause cell cycle arrest in prostate cancer cell lines. Anticancer Res. 27: 3459-3464.
25. Vo, T.P., S. Madlener, Z. Bago-Horvath, et al 2009. Pro- and anti-carcinogenic mechanisms of piceatannol are activated dose-dependently in MCF-7 breast cancer cells. Carcinogenesis 22: 845-852.
26. Murias, M., M.W. Luczak, A. Niepsuj, et al 2008. Cytotoxic activity of 3, 3', 4, 4', 5, 5'-hexahydroxystilbene against breast cancer cells is mediated by induction of p53 and downregulation of mitochondrial superoxide dismutase. Toxicol. In Vitro. 22: 1361-1370.
27. Horvath, Z., P. Saiko, C. Illmer, et al 2005. Synergistic action of resveratrol, an ingredient of wine, with Ara-C and tiazofurin in HL-60 human promyelocytic leukemia cells. Exp. Hematol. 33: 329-335.
28. Horvath, Z., M. Murias, P. Saiko, et al 2006. Cytotoxic and biochemical effects of 3, 3', 4, 4', 5, 5'-hexahydroxystilbene, a novel resveratrol analogue in HL-60 human promyelocytic leukemia cells. Exp. Hematol. 34: 1377-1384.
29. Wachek, V., Z. Horvath, S. Strommer, et al 2005. Resveratrol analogue M8 chemosensitizes malignant melanoma to dacarbacin in vivo. Clin. Cancer Res. Part 2(Suppl S 11): 8971S-8971S.
30. Paulitschke, V., N. Schicher, T. Szekeres, et al 2010. 3, 3', 4, 4', 5, 5'-hexahydroxystilbene impairs melanoma progression in a metastatic mouse model. J. Invest. Dermatol. 130: 1668-1679.