Anticancer efficacy of a difluorodiarylidenyl piperidone (HO-3867) in human ovarian cancer cells and tumor xenografts

Molecular Cancer Therapeutics

Volumn 9, Issue 5, 2010, Pages 1169-1179

  Selvendiran, Karuppaiyah ^a   Tong, Liyue ^a   Bratasz, Anna ^a   Lakshmi Kuppusamy, M ^a   Ahmed, Shabnam ^a   Ravi, Yazhini ^a   Trigg, Nancy J ^a   Rivera, Brian K ^a   Kálai, Tamás ^c   Hideg, Kálmán ^c   Kuppusamy, Periannan ^a,b  

^a OHIO STATE UNIVERSITY   (United States)

^b OHIO STATE UNIVERSITY   (United States)

^c UNIVERSITY OF PÉCS   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

1 [(1 OXYL 2,2,5,5 TETRAMETHYL 2,5 DIHYDRO 1H PYRROL 3 YL)METHYL] 3,5 BIS(4 FLUOROBENZYLIDENE)PIPERIDIN 4 ONE; 3,5 BIS(4 FLUOROBENZYLIDENE)PIPERIDIN 4 ONE; ACTIN; ANTINEOPLASTIC AGENT; CURCUMIN; CYCLIN D1; CYCLIN DEPENDENT KINASE 2; CYCLINE; FAS ANTIGEN; H 4073; HO 3867; JANUS KINASE 1; PIPERIDONE DERIVATIVE; PROTEIN BCL 2; PROTEIN BCL XL; PROTEIN P21; PROTEIN P27; STAT3 PROTEIN; SURVIVIN; UNCLASSIFIED DRUG; VASCULOTROPIN;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; CELL CYCLE ARREST; CONCENTRATION RESPONSE; CONTROLLED STUDY; ENZYME ACTIVATION; ENZYME PHOSPHORYLATION; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; OVARY CANCER; PRIORITY JOURNAL; PROTEIN EXPRESSION; SIGNAL TRANSDUCTION; TUMOR XENOGRAFT;

ANIMALS; ANTINEOPLASTIC AGENTS; CARCINOMA; CELL LINE, TUMOR; DOSE-RESPONSE RELATIONSHIP, DRUG; FEMALE; HUMANS; MICE; MICE, INBRED BALB C; MICE, NUDE; MODELS, BIOLOGICAL; OVARIAN NEOPLASMS; PIPERIDONES; TREATMENT OUTCOME; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 77952218816     PISSN: 15357163     EISSN: None     Source Type: Journal    
DOI: 10.1158/1535-7163.MCT-09-1207     Document Type: Article

References (46)

1. Jemal A, Siegel R, Ward E, et al. Cancer statistics, 2008. CA Cancer J Clin 2008;58:71-96.
2. Ozols RF, Bookman MA, Connolly DC, et al. Focus on epithelial ovarian cancer. Cancer Cell 2004;5:19-24.
3. Bristow RE, Chi DS. Platinum-based neoadjuvant chemotherapy and interval surgical cytoreduction for advanced ovarian cancer: a meta-analysis. Gynecol Oncol 2006;103:1070-1076
4. Harries M, Gore M. Part II: chemotherapy for epithelial ovarian cancer-treatment of recurrent disease. Lancet Oncol 2002;3:537-545 (Pubitemid 34993641)
5. Harries M, Gore M. Part I: chemotherapy for epithelial ovarian cancer-treatment at first diagnosis. Lancet Oncol 2002;3:529-536 (Pubitemid 34993640)
6. Borst P, Rottenberg S, Jonkers J. How do real tumors become resistant to cisplatin? Cell Cycle 2008;7:1353-1359
7. Raj MH, Abd Elmageed ZY, Zhou J, et al. Synergistic action of dietary phyto-antioxidants on survival and proliferation of ovarian cancer cells. Gynecol Oncol 2008;110:432-438
8. Yu H, Jove R. The STATs of cancer-new molecular targets come of age. Nat Rev Cancer 2004;4:97-105.
9. Lu Y, Zhou J, Xu C, et al. JAK/STAT and PI3K/AKT pathways form a mutual transactivation loop and afford resistance to oxidative stress-induced apoptosis in cardiomyocytes. Cell Physiol Biochem 2008; 21:305-314
10. Selvendiran K, Bratasz A, Tong L, Ignarro LJ, Kuppusamy P. NCX- 4016, a nitro-derivative of aspirin, inhibits EGFR and STAT3 signaling and modulates Bcl-2 proteins in cisplatin-resistant human ovarian cancer cells and xenografts. Cell Cycle 2008;7:81-88
11. Yang F, Van Meter TE, Buettner R, et al. Sorafenib inhibits signal transducer and activator of transcription 3 signaling associated with growth arrest and apoptosis of medulloblastomas. Mol Cancer Ther 2008;7:3519-3526
12. Clevenger CV. Roles and regulation of stat family transcription factors in human breast cancer. Am J Pathol 2004;165:1449-1460
13. Durrant D, Richards JE, Walker WT, Baker KA, Simoni D, Lee RM. Mechanism of cell death induced by cis-3, 4′, 5-trimethoxy-3′- aminostilbene in ovarian cancer. Gynecol Oncol 2008;110:110-117
14. Trachootham D, Zhou Y, Zhang H, et al. Selective killing of oncogenically transformed cells through a ROS-mediated mechanism by β-phenylethyl isothiocyanate. Cancer Cell 2006;10:241-252
15. Selvendiran K, Koga H, Ueno T, et al. Luteolin promotes degradation in signal transducer and activator of transcription 3 in human hepatoma cells: an implication for the antitumor potential of flavonoids. Cancer Res 2006;66:4826-4834
16. Bharti AC, Shishodia S, Reuben JM, et al. Nuclear factor-κB and STAT3 are constitutively active in CD138+ cells derived from multiple myeloma patients, and suppression of these transcription factors leads to apoptosis. Blood 2004;103:3175-3184
17. Kim HY, Park EJ, Joe EH, Jou I. Curcumin suppresses Janus kinase- STAT inflammatory signaling through activation of Src homology 2 domain-containing tyrosine phosphatase 2 in brain microglia. J Immunol 2003;171:6072-6079
18. 2/M arrest and apoptosis in cisplatin-resistant human ovarian cancer cells by modulating Akt and p38 MAPK. Cancer Biol Ther 2007;6: 178-184
19. Lin YG, Kunnumakkara AB, Nair A, et al. Curcumin inhibits tumor growth and angiogenesis in ovarian carcinoma by targeting the nuclear factor-κB pathway. Clin Cancer Res 2007;13:3423-3430
20. Adams BK, Ferstl EM, Davis MC, et al. Synthesis and biological evaluation of novel curcumin analogs as anti-cancer and anti-angiogenesis agents. Bioorg Med Chem 2004;12:3871-3883
21. Adams BK, Cai J, Armstrong J, et al. EF24, a novel synthetic curcumin analog, induces apoptosis in cancer cells via a redox-dependent mechanism. Anticancer Drugs 2005;16:263-275
22. Subramaniam D, May R, Sureban SM, et al. Diphenyl difluoroketone: a curcumin derivative with potent in vivo anticancer activity. Cancer Res 2008;68:1962-1969
23. 2/M arrest and apoptosis in cisplatin-resistant human ovarian cancer cells by increasing PTEN expression. J Biol Chem 2007;282:28609-28618
24. Tazi MF, Selvendiran K, Kuppusamy ML, et al. Evaluation of a novel class of fluorinated curcumin analogs for safe and targeted anticancer therapy (STAT). Free Radic Biol Med 2008;45:S56-7.
25. Selvendiran K, Ahmed S, Dayton A, et al. Safe and targeted anti-cancer efficacy of a novel class of antioxidantconjugated difluoro- diarylidenylpiperidones: differential cytotoxicity in healthy and cancer cells. Free Radic Biol Med 2010;48:1228-1235
26. Injac R, Strukelj B. Recent advances in protection against doxorubicin-induced toxicity. Technol Cancer Res Treat 2008;7:497-516.
27. Santos NA, Bezerra CS, Martins NM, Curti C, Bianchi ML, Santos AC. Hydroxyl radical scavenger ameliorates cisplatin-induced nephrotoxicity by preventing oxidative stress, redox state unbalance, impairment of energetic metabolism and apoptosis in rat kidney mitochondria. Cancer Chemother Pharmacol 2008;61:145-155
28. Maliakel DM, Kagiya TV, Nair CK. Prevention of cisplatin-induced nephrotoxicity by glucosides of ascorbic acid and α-tocopherol. Exp Toxicol Pathol 2008;60:521-527
29. Conklin KA. Dietary antioxidants during cancer chemotherapy: impact on chemotherapeutic effectiveness and development of side effects. Nutr Cancer 2000;37:1-18.
30. Samuni Y, Gamson J, Samuni A, et al. Factors influencing nitroxide reduction and cytotoxicity in vitro. Antioxid Redox Signal 2004;6: 587-595
31. Mitchell JB, Krishna MC, Kuppusamy P, Cook JA, Russo A. Protection against oxidative stress by nitroxides. Exp Biol Med (Maywood) 2001;226:620-621
32. Kuppusamy P, Li H, Ilangovan G, et al. Noninvasive imaging of tumor redox status and its modification by tissue glutathione levels. Cancer Res 2002;62:307-312
33. Kuppusamy P, Wang P, Shankar RA, et al. In vivo topical EPR spectroscopy and imaging of nitroxide free radicals and polynitroxylalbumin. Magn Reson Med 1998;40:806-811
34. Hankovzky HO, Hideg K, Lex L. Nitroxyls VII. synthesis and reactions of highly reactive 1-oxyl-2,2,5,5-tetramethyl-2,5-dihydropyrrole-3- ylmethyl sulfonates. Synthesis 1980:914-916
35. Kalai T, Tong L, Balog M, Selvendiran K, Kuppusamy P, Hideg K. Synthesis of N-substituted 3,5-bis(arylidene)-4-piperidones with high antitumor and antioxidant activity. Bioorg Med Chem 2010, in preparation.
36. Bromberg JF, Wrzeszczynska MH, Devgan G, et al. Stat3 as an oncogene. Cell 1999;98:295-303.
37. Burke WM, Jin X, Lin HJ, et al. Inhibition of constitutively active Stat3 suppresses growth of human ovarian and breast cancer cells. Oncogene 2001;20:7925-7934
38. Duriez PJ, Shah GM. Cleavage of poly(ADP-ribose) polymerase: a sensitive parameter to study cell death. Biochem Cell Biol 1997;75: 337-349
39. Deeb D, Jiang H, Gao X, et al. Curcumin [1,7-bis(4-hydroxy-3- methoxyphenyl)-1-6-heptadine-3,5-dione; C21H20O6] sensitizes human prostate cancer cells to tumor necrosis factor-related apoptosis-inducing ligand/Apo2L-induced apoptosis by suppressing nuclear factor-κB via inhibition of the prosurvival Akt signaling pathway. J Pharmacol Exp Ther 2007;321:616-625
40. Gadducci A, Cosio S, Muraca S, Genazzani AR. Molecular mechanisms of apoptosis and chemosensitivity to platinum and paclitaxel in ovarian cancer: biological data and clinical implications. Eur J Gynaecol Oncol 2002;23:390-396
41. Jung EM, Park JW, Choi KS, et al. Curcumin sensitizes tumor necrosis factor-related apoptosis-inducing ligand (TRAIL)-mediated apoptosis through CHOP-independent DR5 upregulation. Carcinogenesis 2006; 27:2008-2017
42. Ivanov VN, Bhoumik A, Krasilnikov M, et al. Cooperation between STAT3 and c-jun suppresses Fas transcription.Mol Cell 2001;7:517-528
43. Kim KW, Mutter RW, Cao C, et al. Inhibition of signal transducer and activator of transcription 3 activity results in down-regulation of Survivin following irradiation. Mol Cancer Ther 2006;5:2659-2665
44. Nielsen M, Kaestel CG, Eriksen KW, et al. Inhibition of constitutively activated Stat3 correlates with altered Bcl-2/Bax expression and induction of apoptosis in mycosis fungoides tumor cells. Leukemia 1999;13:735-738
45. Metz S, Naeth G, Heinrich PC, Muller-Newen G. Novel inhibitors for murine and human leukemia inhibitory factor based on fused soluble receptors. J Biol Chem 2008;283:5985-5995
46. Ziegler DS, Kung AL. Therapeutic targeting of apoptosis pathways in cancer. Curr Opin Oncol 2008;20:97-103. (Pubitemid 350190988)