Effects of pyridine analogs of curcumin on growth, apoptosis and NF-κB activity in prostate cancer PC-3 cells

Anticancer Research

Volumn 33, Issue 4, 2013, Pages 1343-1350

  Wei, Xingchuan ^a   Zhou, Daiying ^b   Wang, Huaqian ^b   Ding, Ning ^c   Cui, Xiao Xing ^c   Wang, Hong ^c   Verano, Michael ^c   Zhang, Kun ^b,d   Conney, Allan H ^b,c   Zheng, Xi ^b,c   Du, Zhi Yun ^b  

^a GUANGZHOU UNIVERSITY   (China)

^b GUANGDONG UNIVERSITY OF TECHNOLOGY   (China)

^c RUTGERS UNIVERSITY   (United States)

^d Wuyi University   (China)

Author keywords

Apoptosis; Curcumin analogues; PC 3 cells; Proliferation; Prostate cancer

Indexed keywords

CURCUMIN; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; MITOGEN ACTIVATED PROTEIN KINASE 1; PYRIDINE DERIVATIVE;

APOPTOSIS; ARTICLE; CANCER CELL; CANCER GROWTH; CANCER INHIBITION; CONCENTRATION RESPONSE; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME PHOSPHORYLATION; HUMAN; HUMAN CELL; IMMUNOHISTOCHEMISTRY; PRIORITY JOURNAL; PROSTATE CANCER; STRUCTURE ACTIVITY RELATION; WESTERN BLOTTING;

APOPTOSIS; BLOTTING, WESTERN; CELL PROLIFERATION; CURCUMIN; ENZYME INHIBITORS; HUMANS; LUCIFERASES; MALE; MITOGEN-ACTIVATED PROTEIN KINASE 1; MITOGEN-ACTIVATED PROTEIN KINASE 3; NF-KAPPA B; PHOSPHORYLATION; PROSTATIC NEOPLASMS; PYRIDINES; SIGNAL TRANSDUCTION; TRANSCRIPTION, GENETIC; TUMOR CELLS, CULTURED;

EID: 84876766968     PISSN: 02507005     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (46)

1. Lao CD, Ruffin MT, Normolle D, Heath DD, Murray SI, Bailey JM, Boggs ME, Crowell J, Rock CL and Brenner DE: Dose escalation of a curcuminoid formulation. BMC Complement Altern Med 6: 10-14, 2006.
2. Goel A, Kunnumakkara AB and Aggarwal BB: Curcumin as " Curecumin": from kitchen to clinic. Biochem Pharmacol 75: 787-809, 2008.
3. Aggarwal BB and Sung B: Pharmacological basis for the role of curcumin in chronic diseases: an age-old spice with modern targets. Trends Pharmacol Sci 30: 85-94, 2009.
4. Sa G and Das T: Anti cancer effects of curcumin: cycle of life and death. Cell Div 3: 14-28, 2008.
5. Moragoda L, Jaszewski R and Majumdar AP: Curcumin induced modulation of cell cycle and apoptosis in gastric and colon cancer cells. Anticancer Res 21: 873-878, 2001. (Pubitemid 32494183)
6. Squires MS, Hudson EA, Howells L, Sale S, Houghton CE, Jones JL, Fox LH, Dickens M, Prigent SA and Manson MM: Relevance of mitogen-activated protein kinase (MAPK) and phosphotidylinositol-3-kinase/protein kinase B (PI3K/PKB) pathways to induction of apoptosis by curcumin in breast cells. Biochem Pharmacol 65: 361-376, 2003. (Pubitemid 36084553)
7. Hanif R, Qiao L, Shiff SJ and Rigas B: Curcumin, a natural plant phenolic food additive, inhibits cell proliferation and induces cell cycle changes in colon adenocarcinoma cell lines by a prostaglandin-independent pathway. J Lab Clin Med 130: 576-584, 1997. (Pubitemid 28029226)
8. Mukhopadhyay A, Bueso-Ramos C, Chatterjee D, Pantazis P and Aggarwal BB: Curcumin down-regulates cell survival mechanisms in human prostate cancer cell lines. Oncogene 20: 7597-7609, 2001. (Pubitemid 33111860)
9. Azuine MA and Bhide SV: Chemopreventive effect of turmeric against stomach and skin tumors induced by chemical carcinogens in Swiss mice. Nutr Cancer 17: 77-83, 1992.
10. Huang MT, Lou YR, Ma W, Newmark HL, Reuhl KR and Conney AH: Inhibitory effects of dietary curcumin on forestomach, duodenal, and colon carcinogenesis in mice. Cancer Res 54: 5841-5847, 1994. (Pubitemid 24375217)
11. Rao C V, Rivenson A, Simi B and Reddy BS: Chemoprevention of colon carcinogenesis by dietary curcumin, a naturally occurring plant phenolic compound. Cancer Res 55: 259-266, 1995.
12. Inano H and Onoda M: Prevention of radiation-induced mammary tumors. Int J Radiat Oncol Biol Phys 52: 212-223, 2002. (Pubitemid 34041574)
13. Pereira MA, Grubbs CJ, Barnes LH, Li H, Olson GR, Eto I, Juliana M, Whitaker LM, Kelloff GJ, Steele VE and Lubet RA: Effects of the phytochemicals, curcumin and quercetin, upon azoxymethane-induced colon cancer and 7,12-dimethylbenz[a] anthracene-induced mammary cancer in rats. Carcinogenesis 17: 1305-1311, 1996.
14. Huang MT, Smart RC, Wong CQ and Conney AH: Inhibitory effect of curcumin, chlorogenic acid, caffeic acid, and ferulic acid on tumor promotion in mouse skin by 12-O-tetradecanoylphorbol-13-acetate. Cancer Res 48: 5941-5946, 1988. (Pubitemid 18266780)
15. Lin YG, Kunnumakkara AB, Nair A, Merritt WM, Han LY, Armaiz-Pena GN, Kamat AA, Spannuth WA, Gershenson DM, Lutgendorf SK, Aggarwal BB and Sood AK: Curcumin inhibits tumor growth and angiogenesis in ovarian carcinoma by targeting the nuclear factor-kappaB pathway. Clin Cancer Res 13: 3423-3430, 2007. (Pubitemid 46944931)
16. Kunnumakkara AB, Guha S, Krishnan S, Diagaradjane P, Gelovani J and Aggarwal BB: Curcumin potentiates antitumor activity of gemcitabine in an orthotopic model of pancreatic cancer through suppression of proliferation, angiogenesis, and inhibition of nuclear factor-kappaB-regulated gene products. Cancer Res 67: 3853-3861, 2007. (Pubitemid 46762173)
17. Sun ZJ, Chen G, Zhang W, Hu X, Liu Y, Zhou Q, Zhu LX and Zhao YF: Curcumin dually inhibits both mammalian target of rapamycin and nuclear factor-κB pathways through a crossed phosphatidylinositol 3-kinase/Akt/IκB kinase complex signaling axis in adenoid cystic carcinoma. Mol Pharmacol 79: 106-118, 2011.
18. erratum in: Mol Pharmacol 79: 628-630, 2011.
19. Jutooru I, Chadalapaka G, Lei P and Safe S: Inhibition of NF kappa B and pancreatic cancer cell and tumor growth by curcumin is dependent on specificity protein down-regulation. J Biol Chem 285: 25332-25344, 2010.
20. Anand P, Sundaram C, Jhurani S, Kunnumakkara AB and Aggarwal BB: Curcumin and cancer: an old-age disease with an age-old solution. Cancer Lett 267: 133-164, 2008.
21. Dhillon N, Aggarwal BB, Newman RA, Wolff RA, Kunnumakkara AB, Abbruzzese JL, Ng CS, Badmaev V and Kurzrock R: Phase II trial of curcumin in patients with advanced pancreatic cancer. Clin Cancer Res 14: 4491-4499, 2008.
22. Cheng AL, Hsu CH, Lin JK, Hsu MM, Ho YF, Shen TS, Ko JY, Lin JT, Lin BR, Ming-Shiang W, Yu HS, Jee SH, Chen GS, Chen TM, Chen CA, Lai MK, Pu YS, Pan MH, Wang YJ, Tsai CC and Hsieh CY: Phase I clinical trial of curcumin, a chemopreventive agent, in patients with high-risk or pre-malignant lesions. Anticancer Res 21: 2895-2900, 2001.
23. Liang G, Shao L, Wang Y, Zhao C, Chu Y, Xiao J, Zhao Y, Li X and Yang S: Exploration and synthesis of curcumin analogues with improved structural stability both in vitro and in vivo as cytotoxic agents. Bioorg Med Chem 17: 2623-2631, 2009.
24. Yadav B, Taurin S, Rosengren RJ, Schumacher M, Diederich M, Somers-Edgar TJ and Larsen L: Synthesis and cytotoxic potential of heterocyclic cyclohexanone analogues of curcumin. Bioorg Med Chem 18: 6701-6707, 2010.
25. Somers-Edgar TJ, Taurin S, Larsen L, Chandramouli A, Nelson MA and Rosengren RJ: Mechanisms for the activity of heterocyclic cyclohexanone curcumin derivatives in estrogen receptor negative human breast cancer cell lines. Invest New Drugs 29: 87-97, 2011.
26. Wei X, Du ZY, Zheng X, Cui XX, Conney AH and Zhang K: Synthesis and evaluation of curcumin-related compounds for anticancer activity. Eur J Med Chem 53: 235-245, 2012.
27. Zheng X, Cui XX, Avila GE, Huang MT, Liu Y, Patel J, Kong AN, Paulino R, Shih WJ, Lin Y, Rabson AB, Reddy BS and Conney AH: Atorvastatin and celecoxib inhibit prostate PC-3 tumors in immunodeficient mice. Clin Cancer Res 13: 5480-5487, 2007. (Pubitemid 47510376)
28. Zheng X, Cui XX, Huang MT, Liu Y, Shih WJ, Lin Y, Lu YP, Wagner GC and Conney AH: Inhibitory effect of voluntary running wheel exercise on the growth of human pancreatic Panc-1 and prostate PC-3 xenograft tumors in immunodeficient mice. Oncol Rep 19: 1583-1588, 2008.
29. Zheng X, Chang RL, Cui XX, Avila G, Huang MT, Liu Y, Kong AN, Rabson AB and Conney AH: Inhibition of NF-kappaB by(E)3-[(4-methylphenyl)-sulfonyl]-2- propenenitrile (BAY11-7082; BAY) is associated with enhanced 12-O-tetradecanoylphorbol-13-acetate-induced growth suppression and apoptosis in human prostate cancer PC-3 cells. Int J Oncol 32: 257-264, 2008. (Pubitemid 351176085)
30. Hsu JC. Multiple Comparisons: Theory and Methods. NewYork: Chapman and Hall, 1996.
31. Markaverich BM, Schauweker TH, Gregory RR, Varma M, Kittrell FS, Medina D and Varma RS: Nuclear type II sites and malignant cell proliferation: Inhibition by 2,6-bis-benzylidenecyclohexanones. Cancer Res 52: 2482-2488, 1992.
32. Adams BK, Ferstl EM, Davis MC, Herold M, Kurtkaya S, Camalier RF, Hollingshead MG, Kaur G, Sausville EA, Rickles FR, Snyder JP, Liotta DC and Shoji M: Synthesis and biological evaluation of novel curcumin analogs as anticancer and anti-angiogenesis agents. Bioorg Med Chem 12: 3871-3883, 2004. (Pubitemid 38798249)
33. Aggarwal BB, Surh YJ and Shishodia S: The Molecular Targets and Therapeutic Uses of Curcumin in Health and Disease. Adv Exp Med Bio Vol 595. Springer, New York, 2007.
34. Connors SK, Chornokur G and Kumar NB: New insights into the mechanisms of green tea catechins in the chemoprevention of prostate cancer. Nutr Cancer 64: 4-22, 2012.
35. DiDonato JA, Mercurio F and Karin M: NF-κB and the link between inflammation and cancer. Immunol Rev 246: 379-400, 2012.
36. Paule B, Terry S, Kheuang L, Soyeux P, Vacherot F and de la Taille A: The NF-kappa B/IL-6 pathway in metastatic androgen-independent prostate cancer: New therapeutic approaches? World J Urol 25: 477-489, 2007.
37. Lessard L, Mes-Masson AM, Lamarre L, Wall L, Lattouf JB and Saad F: NF-κB nuclear localization and its prognostic significance in prostate cancer. BJU Int 91: 417-420, 2003. (Pubitemid 36359653)
38. Ross JS, Kallakury BV, Sheehan CE: Fisher HA, Kaufman RP Jr, Kaur P, Gray K and Stringer B: Expression of nuclear factor-κB and IκB proteins in prostatic adenocarcinomas: correlation of nuclear factor-κB immunoreactivity with disease recurrence. Clin Cancer Res 10: 2466-2472, 2004. (Pubitemid 38445708)
39. Shukla S, MacLennan GT, Fu P, Patel J, Marengo SR, Resnick MI and Gupta S: Nuclear factor-kappa B/p65 (Rel A) is constitutively activated in human prostate adenocarcinoma and correlates with disease progression. Neoplasia 6: 390-400, 2004. (Pubitemid 38924854)
40. Fradet V, Lessard L, Begin LR, Karakiewicz P, Masson AM and Saad F: Nuclear factor-κB nuclear localization is predictive of biochemical recurrence in patients with positive margin prostate cancer. Clin Cancer Res 10: 8460-8464, 2004. (Pubitemid 40053410)
41. Gioeli D, Mandell JW, Petroni GR, Frierson HF and Weber MJ: Activation of mitogen-activated protein kinase associated with prostate cancer progression. Cancer Res 59: 279-284, 1999. (Pubitemid 29048852)
42. Uzgare AR and Isaacs JT: Prostate cancer: Potential targets of anti-proliferative and apoptotic signaling pathways. Int J Biochem Cell Biol 37: 707-714, 2005. (Pubitemid 40202992)
43. Raman M, Chen W and Cobb MH: Differential regulation and properties of MAPKs. Oncogene 26: 3100-3112, 2007. (Pubitemid 46763006)
44. Kook SH, Jang YS and Lee JC: Involvement of JNK-AP-1 and ERK-NF-κB signaling in tension-stimulated expression of type I collagen and MMP-1 in human periodontal ligament fibroblasts. J Appl Physiol 111: 1575-1583, 2011.
45. Shin HK, Kim J, Lee EJ and Kim SH: Inhibitory effect of curcumin on motility of human oral squamous carcinoma YD-10B cells via suppression of ERK and NF-κB activations. Phytother Res 24: 577-582, 2010.
46. Lim JH and Kwon TK: Curcumin inhibits phorbol myristate acetate (PMA)-induced MCP-1 expression by inhibiting ERK and NF-κB transcriptional activity. Food Chem Toxicol 48: 47-52, 2010.