Induction of apoptosis by 5,7-dihydroxy-8-nitrochrysin in breast cancer cells: The role of reactive oxygen species and Akt

International Journal of Oncology

Volumn 37, Issue 5, 2010, Pages 1345-1352

  Zhao, Xiao Chun ^a   Tian, Li ^b   Cao, Jian Guo ^b   Liu, Fei ^b  

^a UNIVERSITY OF SOUTH CHINA   (China)

^b HUNAN NORMAL UNIVERSITY   (China)

Author keywords

5,7 dihydroxy 8 nitrochrysin; Akt; Apoptosis; Breast cancer; Reactive oxygen species

Indexed keywords

5,7 DIHYDROXY 8 NITROCHRYSIN; CHRYSIN; EPIDERMAL GROWTH FACTOR RECEPTOR 2; ESTROGEN RECEPTOR; PROTEIN KINASE B; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CELL IMMORTALIZATION; CELL VIABILITY; CONTROLLED STUDY; DRUG MECHANISM; HUMAN; HUMAN CELL; PRIORITY JOURNAL; PROTEIN DEPHOSPHORYLATION;

EID: 77957866558     PISSN: 10196439     EISSN: 17912423     Source Type: Journal    
DOI: 10.3892/ijo_00000787     Document Type: Article

References (45)

1. Yip CH: Breast cancer in Asia. Methods Mol Biol 471: 51-64, 2009.
2. Sanderson JT, Hordijk J, Denison MS, Springsteel MF, Nantz MH and van den Berg M: Induction and inhibition of aromatase (CYP19) activity by natural and synthetic flavonoid compounds in H295R human adrenocortical carcinoma cells. Toxicol Sci 82: 70-79, 2004.
3. Shin EK, Kwon HS, Kim YH, Shin HK and Kim JK: Chrysin, a natural flavone, improves murine inflammatory bowel diseases. Biochem Biophys Res Commun 381: 502-507, 2009.
4. Lotito SB and Frei B: Dietary flavonoids attenuate tumor necrosis factor alpha-induced adhesion molecule expression in human aortic endothelial cells. Structure-function relationships and activity after first pass metabolism. J Biol Chem 281: 37102-37110, 2006.
5. Park SS, Bae I and Lee YJ: Flavonoids-induced accumulation of hypoxia-inducible factor (HIF)-1alpha/2alpha is mediated through chelation of iron. J Cell Biochem 103: 1989-1998, 2008.
6. Zhang T, Chen X, Qu L, Wu J, Cui R and Zhao Y: Chrysin and its phosphate ester inhibit cell proliferation and induce apoptosis in HeLa cells. Bioorg Med Chem 12: 6097-6105, 2004. (Pubitemid 39440450)
7. Lee SJ, Yoon JH and Song KS: Chrysin inhibited stem cell factor (SCF)/c-Kit complex-induced cell proliferation in human myeloid leukemia cells. Biochem Pharmacol 74: 215-225, 2007.
8. Woo KJ, Jeong YJ, Park JW and Kwon TK: Chrysin-induced apoptosis is mediated through caspase activation and Akt inactivation in U937 leukemia cells. Biochem Biophys Res Commun 325: 1215-1222, 2004.
9. Wang W, VanAlstyne PC, Irons KA, Chen S, Stewart JW and Birt DF: Individual and interactive effects of apigenin analogs on G2/M cell-cycle arrest in human colon carcinoma cell lines. Nutr Cancer 48: 106-114, 2004. (Pubitemid 38823552)
10. Zhang Q, Zhao XH and Wang ZJ: Flavones and flavonols exert cytotoxic effects on a human oesophageal adenocarcinoma cell line (OE33) by causing G2/M arrest and inducing apoptosis. Food Chem Toxicol 46: 2042-2053, 2008.
11. Kachadourian R, Leitner HM and Day BJ: Selected flavonoids potentiate the toxicity of cisplatin in human lung adenocarcinoma cells: a role for glutathione depletion. Int J Oncol 31: 161-168, 2007.
12. Saarinen N, Joshi SC, Ahotupa M, Li X, Ammala J, Makela S and Santti R: No evidence for the in vivo activity of aromatase-inhibiting flavonoids. J Steroid Biochem Mol Biol 78: 231-239, 2001. (Pubitemid 32953617)
13. Walle T, Otake Y, Brubaker JA, Walle UK and Halushka PV: Disposition and metabolism of the flavonoid chrysin in normal volunteers. Br J Clin Pharmacol 51: 143-146, 2001. (Pubitemid 32216062)
14. Park H, Dao TT and Kim HP: Synthesis and inhibition of PGE2 production of 6,8-disubstituted chrysin derivatives. Eur J Med Chem 40: 943-948, 2005. (Pubitemid 41376310)
15. Comte G, Daskiewicz JB, Bayet C, et al: C-Isoprenylation of flavonoids enhances binding affinity toward P-glycoprotein and modulation of cancer cell chemoresistance. J Med Chem 44: 763-768, 2001.
16. Zheng X, Meng WD, Xu YY, Cao JG and Qing FL: Synthesis and anticancer effect of chrysin derivatives. Bioorg Med Chem Lett 13: 881-884, 2003.
17. Ai XH, Zheng X, Tang XQ, et al: Induction of apoptosis of human gastric carcinoma SGC-7901 cell line by 5, 7-dihydroxy- 8-nitrochrysin in vitro. World J Gastroenterol 13: 3824-3828, 2007.
18. Tan XW, Xia H, Xu JH and Cao JG: Induction of apoptosis in human liver carcinoma HepG2 cell line by 5-allyl-7-gen-difluoromethylenechrysin. World J Gastroenterol 15: 2234-2239, 2009.
19. Menard S, Tagliabue E, Campiglio M and Pupa SM: Role of HER2 gene overexpression in breast carcinoma. J Cell Physiol 182: 150-162, 2000.
20. Fedi P, Pierce JH, di Fiore PP and Kraus MH: Efficient coupling with phosphatidylinositol 3-kinase, but not phospholipase C gamma or GTPase-activating protein, distinguishes ErbB-3 signaling from that of other ErbB/EGFR family members. Mol Cell Biol 14: 492-500, 1994.
21. Hellyer NJ, Kim MS and Koland JG: Heregulin-dependent activation of phosphoinositide 3-kinase and Akt via the ErbB2/ ErbB3 co-receptor. J Biol Chem 276: 42153-42161, 2001.
22. Downward J: Lipid-regulated kinases: some common themes at last. Science 279: 673-674, 1998.
23. Datta SR, Dudek H, Tao X, Masters S, Fu H, Gotoh Y and Greenberg ME: Akt phosphorylation of BAD couples survival signals to the cell-intrinsic death machinery. Cell 91: 231-241, 1997.
24. Cardone MH, Roy N, Stennicke HR, et al: Regulation of cell death protease caspase-9 by phosphorylation. Science 282: 1318-1321, 1998.
25. Brunet A, Bonni A, Zigmond MJ, et al: Akt promotes cell survival by phosphorylating and inhibiting a Forkhead transcription factor. Cell 96: 857-868, 1999.
26. Jing Y, Dai J, Chalmers-Redman RM, Tatton WG and Waxman S: Arsenic trioxide selectively induces acute promyelocytic leukemia cell apoptosis via a hydrogen peroxide-dependent pathway. Blood 94: 2102-2111, 1999.
27. Jabs T: Reactive oxygen intermediates as mediators of programmed cell death in plants and animals. Biochem Pharmacol 57: 231-245, 1999.
28. Kachadourian R and Day BJ: Flavonoid-induced glutathione depletion: potential implications for cancer treatment. Free Radic Biol Med 41: 65-76, 2006.
29. Way TD, Kao MC and Lin JK: Apigenin induces apoptosis through proteasomal degradation of HER2/neu in HER2/neuoverexpressing breast cancer cells via the phosphatidylinositol 3-kinase/Akt-dependent pathway. J Biol Chem 279: 4479-4489, 2004.
30. Kitazawa M, Wagner JR, Kirby ML, Anantharam V and Kanthasamy AG: Oxidative stress and mitochondrial-mediated apoptosis in dopaminergic cells exposed to methylcyclopentadienyl manganese tricarbonyl. J Pharmacol Exp Ther 302: 26-35, 2002. (Pubitemid 34680417)
31. Lee YJ, Lee DH, Cho CK, et al: HSP25 inhibits radiation-induced apoptosis through reduction of PKCdelta-mediated ROS production. Oncogene 24: 3715-3725, 2005.
32. Busija DW, Gaspar T, Domoki F, Katakam PV and Bari F: Mitochondrial-mediated suppression of ROS production upon exposure of neurons to lethal stress: mitochondrial targeted preconditioning. Adv Drug Deliv Rev 60: 1471-1477, 2008.
33. Repicky A, Jantova S and Cipak L: Apoptosis induced by 2-acetyl-3-(6-methoxybenzothiazo)-2-yl-amino-acrylonitrile in human leukemia cells involves ROS-mitochondrial mediated death signaling and activation of p38 MAPK. Cancer Lett 277: 55-63, 2009.
34. Bohmont C, Aaronson LM, Mann K and Pardini RS: Inhibition of mitochondrial NADH oxidase, succinoxidase, and ATPase by naturally occurring flavonoids. J Nat Prod 50: 427-433, 1987. (Pubitemid 17134093)
35. Hodnick WF, Bohmont CW, Capps C and Pardini RS: Inhibition of the mitochondrial NADH-oxidase (NADH-coenzyme Q oxido-reductase) enzyme system by flavonoids: a structure-activity study. Biochem Pharmacol 36: 2873-2874, 1987. (Pubitemid 17123074)
36. Siess MH, Le Bon AM, Canivenc-Lavier MC, Amiot MJ, Sabatier S, Aubert SY and Suschetet M: Flavonoids of honey and propolis: characterization and effects on hepatic drug-metabolizing enzymes and benzo[a]pyrene-DNA binding in rats. J Agric Food Chem 44: 2297-2301, 1996. (Pubitemid 126454453)
37. Torres M and Forman HJ: Redox signaling and the MAP kinase pathways. Biofactors 17: 287-296, 2003.
38. Boonstra J and Post JA: Molecular events associated with reactive oxygen species and cell cycle progression in mammalian cells. Gene 337: 1-13, 2004.
39. Richard D, Hollender P and Chenais B: Involvement of reactive oxygen species in aclarubicin-induced differentiation and invasiveness of HL-60 leukemia cells. Int J Oncol 21: 393-399, 2002.
40. Batista EL Jr, Warbington M, Badwey JA and Van Dyke TE: Differentiation of HL-60 cells to granulocytes involves regulation of select diacylglycerol kinases (DGKs). J Cell Biochem 94: 774-793, 2005.
41. Orrenius S, Gogvadze V and Zhivotovsky B: Mitochondrial oxidative stress: implications for cell death. Annu Rev Pharmacol Toxicol 47: 143-183, 2007.
42. Bharti AC, Donato N, Singh S and Aggarwal BB: Curcumin (diferuloylmethane) down-regulates the constitutive activation of nuclear factor-kappa B and IkappaBalpha kinase in human multiple myeloma cells, leading to suppression of proliferation and induction of apoptosis. Blood 101: 1053-1062, 2003.
43. Katso R, Okkenhaug K, Ahmadi K, White S, Timms J and Waterfield MD: Cellular function of phosphoinositide 3-kinases: implications for development, homeostasis, and cancer. Annu Rev Cell Dev Biol 17: 615-675, 2001.
44. Leung WK, Bai AH, Chan VY, et al: Effect of peroxisome proliferator activated receptor gamma ligands on growth and gene expression profiles of gastric cancer cells. Gut 53: 331-338, 2004.
45. Li M, Lee TW, Mok TS, Warner TD, Yim AP and Chen GG: Activation of peroxisome proliferator-activated receptor-gamma by troglitazone (TGZ) inhibits human lung cell growth. J Cell Biochem 96: 760-774, 2005.