β-Elemene piperazine derivatives induce apoptosis in human leukemia cells through downregulation of c-FLIP and Generation of ROS

PLoS ONE

Volumn 6, Issue 1, 2011, Pages

  Yu, Zhiying ^a,c   Wang, Rui ^b   Xu, Liying ^a   Xie, Siwei ^a   Dong, Jinhua ^a   Jing, Yongkui ^b  

^a SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

^b MOUNT SINAI SCHOOL OF MEDICINE   (United States)

^c Food Science Institute   (China)

Author keywords

[No Author keywords available]

Indexed keywords

13 (3 METHYL 1 PIPERAZINYL) BETA ELEMENE; 13 (3,5 DIMETHYL 1 PIPERAZINYL) BETA ELEMENE; 13 (4 ETHYL 1 PIPERAZINYL) BETA ELEMENE; 13 (4 ISOPROPYL 1 PIPERAZINYL) BETA ELEMENE; 13 PIPERAZINYL BETA ELEMENE; BENZYLOXYCARBONYLLEUCYLLEUCYLLEUCINAL; BETA ELEMENE; CASPASE 3; CASPASE 8; CASPASE 9; DEATH RECEPTOR; FLICE INHIBITORY PROTEIN; HYDROGEN PEROXIDE; PIPERAZINE DERIVATIVE; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG; BETA-ELEMENE; CFLAR PROTEIN, HUMAN; PIPERAZINE; SESQUITERPENE;

APOPTOSIS; ARTICLE; CELL STRAIN HL 60; CELL STRAIN K 562; CONTROLLED STUDY; DNA FRAGMENTATION; DOWN REGULATION; DRUG CYTOTOXICITY; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; GROWTH INHIBITION; HUMAN; HUMAN CELL; LEUKEMIA CELL; MITOCHONDRIAL MEMBRANE POTENTIAL; PROTEIN CLEAVAGE; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; METABOLISM; MITOCHONDRION; TUMOR CELL LINE;

CURCUMA WENYUJIN;

APOPTOSIS; CASP8 AND FADD-LIKE APOPTOSIS REGULATING PROTEIN; CELL LINE, TUMOR; DOWN-REGULATION; HUMANS; HYDROGEN PEROXIDE; MITOCHONDRIA; PIPERAZINES; REACTIVE OXYGEN SPECIES; RECEPTORS, DEATH DOMAIN; SESQUITERPENES;

EID: 79551563604     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0015843     Document Type: Article

References (36)

1. Li X, Wang G, Zhao J, Ding H, Cunningham C, et al. (2005) Antiproliferative effect of beta-elemene in chemoresistant ovarian carcinoma cells is mediated through arrest of the cell cycle at the G2-M phase. Cell Mol Life Sci 62: 894-904.
2. Wang G, Li X, Huang F, Zhao J, Ding H, et al. (2005) Antitumor effect of betaelemene in non-small-cell lung cancer cells is mediated via induction of cell cycle arrest and apoptotic cell death. Cell Mol Life Sci 62: 881-893.
3. Wang Y, Deng Y, Mao S, Jin S, Wang J, et al. (2005) Characterization and body distribution of beta-elemene solid lipid nanoparticles (SLN). Drug Dev Ind Pharm 31: 769-778.
4. Xu L, Tao S, Wang X, Yu Z, Wang M, et al. (2006) The synthesis and antiproliferative effects of beta-elemene derivatives with mTOR inhibition activity. Bioorg Med Chem 14: 5351-5356.
5. Jing Y, Dai J, Chalmers-Redman RM, Tatton WG, Waxman S (1999) Arsenic trioxide selectively induces acute promyelocytic leukemia cell apoptosis via a hydrogen peroxide-dependent pathway. Blood 94: 2102-2111.
6. Kasugai I, Yamada M (1992) High production of catalase in hydrogen peroxideresistant human leukemia HL-60 cell lines. Leuk Res 16: 173-179.
7. Lombard C, Nagarkatti M, Nagarkatti PS (2005) Targeting cannabinoid receptors to treat leukemia: role of cross-talk between extrinsic and intrinsic pathways in Delta9-tetrahydrocannabinol (THC)-induced apoptosis of Jurkat cells. Leuk Res 29: 915-922.
8. Dai J, Weinberg RS, Waxman S, Jing Y (1999) Malignant cells can be sensitized to undergo growth inhibition and apoptosis by arsenic trioxide through modulation of the glutathione redox system. Blood 93: 268-277.
9. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72: 248-254.
10. Peter ME (2004) The flip side of FLIP. Biochem J 382: e1-3.
11. Yu JW, Shi Y (2008) FLIP and the death effector domain family. Oncogene 27: 6216-6227.
12. Zhang S, Shen HM, Ong CN (2005) Down-regulation of c-FLIP contributes to the sensitization effect of 3,3′-diindolylmethane on TRAIL-induced apoptosis in cancer cells. Mol Cancer Ther 4: 1972-1981.
13. Liu X, Yue P, Schonthal AH, Khuri FR, Sun SY (2006) Cellular FLICEinhibitory protein down-regulation contributes to celecoxib-induced apoptosis in human lung cancer cells. Cancer Res 66: 11115-11119.
14. Li W, Zhang X, Olumi AF (2007) MG-132 sensitizes TRAIL-resistant prostate cancer cells by activating c-Fos/c-Jun heterodimers and repressing c-FLIP(L). Cancer Res 67: 2247-2255.
15. Kabore AF, Sun J, Hu X, McCrea K, Johnston JB, et al. (2006) The TRAIL apoptotic pathway mediates proteasome inhibitor induced apoptosis in primary chronic lymphocytic leukemia cells. Apoptosis 11: 1175-1193.
16. Yu Z, Wang R, Xu L, Dong J, Jing Y (2008) N-(beta-Elemene-13-yl)tryptophan methyl ester induces apoptosis in human leukemia cells and synergizes with arsenic trioxide through a hydrogen peroxide dependent pathway. Cancer Lett 269: 165-173.
17. Armstrong JS (2006) Mitochondria: a target for cancer therapy. Br J Pharmacol 147: 239-248.
18. Ozoren N, El-Deiry WS (2003) Cell surface Death Receptor signaling in normal and cancer cells. Semin Cancer Biol 13: 135-147.
19. Decaudin D, Marzo I, Brenner C, Kroemer G (1998) Mitochondria in chemotherapy-induced apoptosis: a prospective novel target of cancer therapy (review). Int J Oncol 12: 141-152.
20. Nakazato T, Ito K, Ikeda Y, Kizaki M (2005) Green tea component, catechin, induces apoptosis of human malignant B cells via production of reactive oxygen species. Clin Cancer Res 11: 6040-6049.
21. Yamada M, Hashinaka K, Inazawa J, Abe T (1991) Expression of catalase and myeloperoxidase genes in hydrogen peroxide-resistant HL-60 cells. DNA Cell Biol 10: 735-742.
22. Kruidering M, Evan GI (2000) Caspase-8 in apoptosis: the beginning of ''the end''? IUBMB Life 50: 85-90.
23. Guseva NV, Taghiyev AF, Rokhlin OW, Cohen MB (2004) Death receptorinduced cell death in prostate cancer. J Cell Biochem 91: 70-99.
24. Kouhara J, Yoshida T, Nakata S, Horinaka M, Wakada M, et al. (2007) Fenretinide up-regulates DR5/TRAIL-R2 expression via the induction of the transcription factor CHOP and combined treatment with fenretinide and TRAIL induces synergistic apoptosis in colon cancer cell lines. Int J Oncol 30: 679-687.
25. Yoshida T, Shiraishi T, Nakata S, Horinaka M, Wakada M, et al. (2005) Proteasome inhibitor MG132 induces death receptor 5 through CCAAT/ enhancer-binding protein homologous protein. Cancer Res 65: 5662-5667.
26. Abdelrahim M, Newman K, Vanderlaag K, Samudio I, Safe S (2006) 3,3′-diindolylmethane (DIM) and its derivatives induce apoptosis in pancreatic cancer cells through endoplasmic reticulum stress-dependent upregulation of DR5. Carcinogenesis 27: 717-728.
27. Xia L, Chen D, Han R, Fang Q, Waxman S, et al. (2005) Boswellic acid acetate induces apoptosis through caspase-mediated pathways in myeloid leukemia cells. Mol Cancer Ther 4: 381-388.
28. Lu M, Xia L, Hua H, Jing Y (2008) Acetyl-keto-beta-boswellic acid induces apoptosis through a death receptor 5-mediated pathway in prostate cancer cells. Cancer Res 68: 1180-1186.
29. Liu X, Yue P, Chen S, Hu L, Lonial S, et al. (2007) The proteasome inhibitor PS-341 (bortezomib) up-regulates DR5 expression leading to induction of apoptosis and enhancement of TRAIL-induced apoptosis despite up-regulation of c-FLIP and survivin expression in human NSCLC cells. Cancer Res 67: 4981-4988.
30. Day TW, Najafi F, Wu CH, Safa AR (2006) Cellular FLICE-like inhibitory protein (c-FLIP): a novel target for Taxol-induced apoptosis. Biochem Pharmacol 71: 1551-1561.
31. Sharp DA, Lawrence DA, Ashkenazi A (2005) Selective knockdown of the long variant of cellular FLICE inhibitory protein augments death receptor-mediated caspase-8 activation and apoptosis. J Biol Chem 280: 19401-19409.
32. Fukazawa T, Fujiwara T, Uno F, Teraishi F, Kadowaki Y, et al. (2001) Accelerated degradation of cellular FLIP protein through the ubiquitinproteasome pathway in p53-mediated apoptosis of human cancer cells. Oncogene 20: 5225-5231.
33. Poukkula M, Kaunisto A, Hietakangas V, Denessiouk K, Katajamaki T, et al. (2005) Rapid turnover of c-FLIPshort is determined by its unique C-terminal tail. J Biol Chem 280: 27345-27355.
34. Kim Y, Suh N, Sporn M, Reed JC (2002) An inducible pathway for degradation of FLIP protein sensitizes tumor cells to TRAIL-induced apoptosis. J Biol Chem 277: 22320-22329.
35. Kauh J, Fan S, Xia M, Yue P, Yang L, et al. c-FLIP degradation mediates sensitization of pancreatic cancer cells to TRAIL-induced apoptosis by the histone deacetylase inhibitor LBH589. PLoS One 5: e10376.
36. Lin Y, Liu X, Yue P, Benbrook DM, Berlin KD, et al. (2008) Involvement of c- FLIP and survivin down-regulation in flexible heteroarotinoid-induced apoptosis and enhancement of TRAIL-initiated apoptosis in lung cancer cells. Mol Cancer Ther 7: 3556-3565.