Novel resveratrol analogs induce apoptosis and cause cell cycle arrest in HT29 human colon cancer cells: Inhibition of ribonucleotide reductase activity

Oncology Reports

Volumn 19, Issue 6, 2008, Pages 1621-1626

  Saiko, Philipp ^a   Pemberger, Michael ^a   Horvath, Zsuzsanna ^a   Savinc, Ivo ^a   Grusch, Michael ^b   Handler, Norbert ^c   Erker, Thomas ^c   Jaeger, Walter ^c   Fritzer Szekeres, Monika ^a   Szekeres, Thomas ^a  

^a MEDICAL UNIVERSITY OF VIENNA   (Austria)

^b MEDICAL UNIVERSITY OF VIENNA   (Austria)

^c UNIVERSITY OF VIENNA   (Austria)

Author keywords

3; 3,3 ; 3,4 ; 3 ; 4; 4 5 tetramethoxy trans stilbene; 4 ; 5; 5 trimethoxy transtilbene; 5 hexadroxy trans stilbene; Apoptosis; Cell cycle arrest; Colon cancer; Resveratrol; Ribonucleotide reductase

Indexed keywords

3,3',4,4',5,5' HEXAHYDROXY STILBENE; 3,3',4,5' TETRAMETHOXY STILBENE; 3,4',5 TRIMETHOXY STILBENE; DEOXYRIBONUCLEOSIDE TRIPHOSPHATE; PHENOL DERIVATIVE; RESVERATROL; RIBONUCLEOTIDE REDUCTASE; UNCLASSIFIED DRUG; 3,3',4,4',5,5' HEXAHYDROXYSTILBENE; 3,3',4,4',5,5'-HEXAHYDROXYSTILBENE; 3,3',4,5' TETRAMETHOXYSTILBENE; 3,3',4,5'-TETRAMETHOXYSTILBENE; 3,5,4' TRI O METHYLRESVERATROL; 3,5,4'-TRI-O-METHYLRESVERATROL; ANISOLE DERIVATIVE; ANTINEOPLASTIC AGENT; DEOXYRIBONUCLEOTIDE; DRUG DERIVATIVE; PYROGALLOL; STILBENE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CELL CYCLE ARREST; CELL CYCLE G0 PHASE; CELL CYCLE G1 PHASE; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CELL STRAIN HT29; CELLULAR DISTRIBUTION; COLON CANCER; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; FLUORESCENCE ACTIVATED CELL SORTING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; PRIORITY JOURNAL; CELL CYCLE; CHEMICAL STRUCTURE; DRUG ANTAGONISM; DRUG EFFECT; DRUG SCREENING; METABOLISM; SYNTHESIS;

ANISOLES; ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL CYCLE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEOXYRIBONUCLEOTIDES; HT29 CELLS; HUMANS; MOLECULAR STRUCTURE; PYROGALLOL; RIBONUCLEOTIDE REDUCTASES; STILBENES; TUMOR STEM CELL ASSAY;

EID: 48849103277     PISSN: 1021335X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (29)

1. Langcake P and Pryce RJ: The production of resveratrol by Vitis vinifera and other members of the Vitaceae as a response to infection or injury. Physiol Plant Pathol 9: 77-86, 1976.
2. Baur JA and Sinclair DA: Therapeutic potential of resveratrol: the in vivo evidence. Nat Rev Drug Discov 5: 493-506, 2006.
3. Dong Z: Molecular mechanism of the chemopreventive effect of resveratrol. Mutat Res 523-524: 145-150, 2003.
4. Hursting SD, Slaga TJ, Fischer SM, DiGiovanni J and Phang JM: Mechanism-based cancer prevention approaches: targets, examples, and the use of transgenic mice. J Natl Cancer Inst 91: 215-225, 1999.
5. Aggarwal BB and Shishodia S: Molecular targets of dietary agents for prevention and therapy of cancer. Biochem Pharmacol 71: 1397-1421, 2006.
6. Jang M, Cai L, Udeani GO, Slowing KV, Thomas CF, Beecher CW, Fong HH, Farnsworth NR, Kinghorn AD, Mehta RG, Moon RC and Pezzuto JM: Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 275: 218-220, 1997.
7. Stewart JR, Christman KL and O'Brian CA: Effects of resveratrol on the autophosphorylation of phorbol ester-responsive protein kinases: inhibition of protein kinase D but not protein kinase C isozyme autophosphorylation. Biochem Pharmacol 60: 1355-1359, 2000.
8. Stewart JR, Ward NE, Ioannides CG and O'Brian CA: Resveratrol. preferentially inhibits protein kinase C-catalyzed phosphorylation of a cofactor-independent, arginine-rich protein substrate by a novel mechanism. Biochemistry 38: 13244-13251, 1999.
9. Bhat KP, Lantvit D, Christov K, Mehta RG, Moon RC and Pezzuto, JM: Estrogenic and antiestrogenic properties of resveratrol in mammary tumor models. Cancer Res 61: 7456-7463, 2001.
10. Gehm BD, McAndrews JM, Chien PY and Jameson JL: Resveratrol, a polyphenolic compound found in grapes and wine, is an agonist for the estrogen receptor. Proc Natl Acad Sci USA 94: 14138-14143, 1997.
11. Mitchell SH, Zhu W and Young CY: Resveratrol inhibits the expression and function of the androgen receptor in LNCaP prostate cancer cells. Cancer Res 59: 5892-5895, 1999.
12. Stojanovic S, Sprinz H and Brede O: Efficiency and mechanism of the antioxidant action of trans-resveratrol and its analogues in the radical liposome oxidation. Arch Biochem Biophys 391: 79-89, 2001.
13. Elford HL, Freese M, Passamani E and Morris HP: Ribonucleotide reductase and cell proliferation. I. Variations of ribonucleotide reductase activity with tumor growth rate in a series of rat hepatomas. J Biol Chem 245: 5228-5233, 1970.
14. Fontecave M, Lepoivre M, Elleingand E, Gerez C and Guittet O: Resveratrol, a remarkable inhibitor of ribonucleotide reductase. FEBS Lett 421: 277-279, 1998.
15. Locatelli GA, Savio M, Forti L, Shevelev I, Ramadan K, Stivala LA, Vannini V, Hubscher U, Spadari S and Maga G: Inhibition of mammalian DNA polymerases by resveratrol: mechanism and structural determinants. Biochem J 389: 259-268, 2005.
16. Ragione FD, Cucciolla V, Borriello A, Pietra VD, Racioppi L, Soldati G, Manna C, Galletti P and Zappia V: Resveratrol arrests the cell division cycle at S/G2 phase transition. Biochem Biophys Res Commun 250: 53-58, 1998.
17. Damianaki A, Bakogeorgou E, Kampa M, Notas G, Hatzoglou A, Panagiotou S, Gemetzi C, Kouroumalis E, Martin PM and Castanas E: Potent inhibitory action of red wine polyphenols on human breast cancer cells. J Cell Biochem 79: 429-441, 2000.
18. Gautam SC, Xu YX, Dumaguin M, Janakiraman N and Chapman RA: Resveratrol selectively inhibits leukemia cells: a prospective agent for ex vivo bone marrow purging. Bone Marrow Transplant 25: 639-645, 2000.
19. Pozo-Guisado E, Alvarez-Barrientos A, Mulero-Navarro S, Santiago-Josefat B and Fernandez-Salguero PM: The antiproliferative activity of resveratrol results in apoptosis in MCF-7 but not in MDA-MB-231 human breast cancer cells: cell-specific alteration of the cell cycle. Biochem Pharmacol 64: 1375-1386, 2002.
20. Schneider Y, Vincent F, Duranton B, Badolo L, Gosse F, Bergmann C, Seiler N and Raul F: Anti-proliferative effect of resveratrol, a natural component of grapes and wine, on human colonic cancer cells. Cancer Lett 158: 85-91, 2000.
21. Zhou HB, Yan Y, Sun YN and Zhu JR: Resveratrol induces apoptosis in human esophageal carcinoma cells. World J Gastroenterol 9: 408-411, 2003.
22. Horvath Z, Saiko P, Illmer C, Madlener S, Hoechtl T, Bauer W, Erker T, Jaeger W, Fritzer-Szekeres M and Szekeres T: 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, 2005.
23. Horvath Z, Murias M, Saiko P, Erker T, Handler N, Madlener S, Jaeger W, Grusch M, Fritzer-Szekeres M, Krupitza G and Szekeres T: Cytotoxic and biochemical effects of 3,3′,4,4′,5,5′-hexahydroxystilbene, a novel resveratrol analog in HL-60 human promyelocytic leukemia cells. Exp Hematol 34: 1377-1384, 2006.
24. Murias M, Handler N, Erker T, Pleban K, Ecker G, Saiko P, Szekeres T and Jager W: Resveratrol analogues as selective cyclooxygenase-2 inhibitors: synthesis and structure-activity relationship. Bioorg Med Chem 12: 5571-5578, 2004.
25. Grusch M, Polgar D, Gfatter S, Leuhuber K, Huettenbrenner S, Leisser C, Fuhrmann G, Kassie F, Steinkellner H, Smid K, Peters GJ, Jayaram HN, Klepal W, Szekeres T, Knasmuller S and Krupitza G: Maintenance of ATP favours apoptosis over necrosis triggered by benzamide riboside. Cell Death Differ 9: 169-178, 2002.
26. Garrett C and Santi DV: A rapid and sensitive high pressure liquid chromatography assay for deoxyribonucleoside triphosphates in cell extracts. Anal Biochem 99: 268-273, 1979.
27. Robinson BW, Im MM, Ljungman M, Praz F and Shewach DS: Enhanced radio sensitization with gemcitabine in mismatch repair-deficient HCT116 cells. Cancer Res 63: 6935-6941, 2003.
28. Roberti M, Pizzirani D, Simoni D, Rondanin R, Baruchello R, Bonora C, Buscemi F, Grimaudo S and Tolomeo M: Synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents. J Med Chem 46: 3546-3554, 2003.
29. Tolomeo M, Grimaudo S, Di Cristina A, Roberti M, Pizzirani D, Meli M, Dusonchet L, Gebbia N, Abbadessa V, Crosta L, Barucchello R, Grisolia G, Invidiata F and Simoni D: Pterostilbene and 3′-hydroxypterostilbene are effective apoptosis-inducing agents in MDR and BCR-ABL-expressing leukemia cells. Int J Biochem Cell Biol 37: 1709-1726, 2005.