A monocarbonyl analogue of curcumin, 1,5-bis(3-hydroxyphenyl)-1,4-pentadiene-3-one (Ca 37), exhibits potent growth suppressive activity and enhances the inhibitory effect of curcumin on human prostate cancer cells

Siegel R, Naishadham D, Jemal A (2012) Cancer statistics, 2012. CA Cancer J Clin 62(1):10–29 Teiten MH, Gaascht F, Eifes S, Dicato M, Diederich M (2010) Chemopreventive potential of curcumin in prostate cancer. Genes Nutr 5(1):61–74 Fesik SW (2005) Promoting apoptosis as a strategy for cancer drug discovery. Nat Rev Cancer 5(11):876–885 Ryter SW, Kim HP, Hoetzel A, Park JW, Nakahira K, Wang X, Choi AM (2007) Mechanisms of cell death in oxidative stress. Antioxid Redox Signal 9(1):49–89 Shankar S, Srivastava RK (2007) Involvement of Bcl-2 family members, phosphatidylinositol 3′-kinase/AKT and mitochondrial p53 in curcumin (diferulolylmethane)-induced apoptosis in prostate cancer. Int J Oncol 30(4):905–918 Hilchie AL, Furlong SJ, Sutton K, Richardson A, Robichaud MR, Giacomantonio CA, Ridgway ND, Hoskin DW (2010) Curcumin-induced apoptosis in PC3 prostate carcinoma cells is caspase-independent and involves cellular ceramide accumulation and damage to mitochondria. Nutr Cancer 62(3):379–389 Anand P, Kunnumakkara AB, Newman RA, Aggarwal BB (2007) Bioavailability of curcumin: problems and promises. Mol Pharm 4(6):807–818 Agrawal DK, Mishra PK (2010) Curcumin and its analogues: potential anticancer agents. Med Res Rev 30(5):818–860 Lee JW, Hong HM, Kwon DD, Pae HO, Jeong HJ (2010) Dimethoxycurcumin, a structural analogue of curcumin, induces apoptosis in human renal carcinoma caki cells through the production of reactive oxygen species, the release of cytochrome C, and the activation of caspase-3. Korean J Urol 51(12):870–878 Wu CL, Liao YF, Hung YC, Lu KH, Hung HC, Liu GY (2011) Ornithine decarboxylase prevents dibenzoylmethane-induced apoptosis through repressing reactive oxygen species generation. J Biochem Mol Toxicol 25(5):312–319 Fajardo AM, MacKenzie DA, Ji M, Deck LM, Vander Jagt DL, Thompson TA, Bisoffi M (2012) The curcumin analog ca27 down-regulates androgen receptor through an oxidative stress mediated mechanism in human prostate cancer cells. Prostate 72(6):612–625 Weber WM, Hunsaker LA, Abcouwer SF, Deck LM, Vander Jagt DL (2005) Anti-oxidant activities of curcumin and related enones. Bioorg Med Chem 13(11):3811–3820 Adams BK, Ferstl EM, Davis MC, Herold M, Kurtkaya S, Camalier RF, Hollingshead MG, Kaur G, Sausville EA, Rickles FR, Snyder JP, Liotta DC, Shoji M (2004) Synthesis and biological evaluation of novel curcumin analogs as anti-cancer and anti-angiogenesis agents. Bioorg Med Chem 12(14):3871–3883 Saotome K, Morita H, Umeda M (1989) Cytotoxicity test with simplified crystal violet staining method using microtitre plates and its application to injection drugs. Toxicol In Vitro 3(4):317–321 Halliwell B, Whiteman M (2004) Measuring reactive species and oxidative damage in vivo and in cell culture: how should you do it and what do the results mean? Br J Pharmacol 142(2):231–255 Luo C, Wang X, Long J, Liu J (2006) An NADH-tetrazolium-coupled sensitive assay for malate dehydrogenase in mitochondria and crude tissue homogenates. J Biochem Biophys Methods 68(2):101–111 Janssen AJ, Trijbels FJ, Sengers RC, Smeitink JA, van den Heuvel LP, Wintjes LT, Stoltenborg-Hogenkamp BJ, Rodenburg RJ (2007) Spectrophotometric assay for complex I of the respiratory chain in tissue samples and cultured fibroblasts. Clin Chem 53(4):729–734 Hatefi Y, Stiggall DL (1978) Preparation and properties of succinate: ubiquinone oxidoreductase (complex II). Methods Enzymol 53:21–27 Luo C, Long J, Liu J (2008) An improved spectrophotometric method for a more specific and accurate assay of mitochondrial complex III activity. Clin Chim Acta 395(1–2):38–41 Errede B, Kamen MD, Hatefi Y (1978) Preparation and properties of complex IV (ferrocytochrome c: oxygen oxidoreductase EC 1.9.3.1). Methods Enzymol 53:40–47 Humphries KM, Szweda LI (1998) Selective inactivation of α-ketoglutarate dehydrogenase and pyruvate dehydrogenase: reaction of lipoic acid with 4-hydroxy-2-nonenal. Biochemistry 37(45):15835–15841 Khor TO, Keum YS, Lin W, Kim JH, Hu R, Shen G, Xu C, Gopalakrishnan A, Reddy B, Zheng X, Conney AH, Kong AN (2006) Combined inhibitory effects of curcumin and phenethyl isothiocyanate on the growth of human PC-3 prostate xenografts in immunodeficient mice. Cancer Res 66(2):613–621 Jemal A, Center MM, DeSantis C, Ward EM (2010) Global patterns of cancer incidence and mortality rates and trends. Cancer Epidemiol Biomarkers Prev 19(8):1893–1907 Kimura T (2012) East meets West: ethnic differences in prostate cancer epidemiology between East Asians and Caucasians. Chin J Cancer 31(9):421–429 Wolk A (2005) Diet, lifestyle and risk of prostate cancer. Acta Oncol 44(3):277–281 Liu Y, Fuchs J, Li C, Lin J (2010) IL-6, a risk factor for hepatocellular carcinoma: FLLL32 inhibits IL-6-induced STAT3 phosphorylation in human hepatocellular cancer cells. Cell Cycle 9(17):3423–3427 Liu A, Liu Y, Li PK, Li C, Lin J (2011) LLL12 inhibits endogenous and exogenous interleukin-6-induced STAT3 phosphorylation in human pancreatic cancer cells. Anticancer Res 31(6):2029–2035 Ball S, Li C, Li PK, Lin J (2011) The small molecule, LLL12, inhibits STAT3 phosphorylation and induces apoptosis in medulloblastoma and glioblastoma cells. PLoS ONE 6(4):e18820 Friedman L, Lin L, Ball S, Bekaii-Saab T, Fuchs J, Li PK, Li C, Lin J (2009) Curcumin analogues exhibit enhanced growth suppressive activity in human pancreatic cancer cells. Anticancer Drug 20(6):444–449 Lin L, Hutzen B, Ball S, Foust E, Sobo M, Deangelis S, Pandit B, Friedman L, Li C, Li PK, Fuchs J, Lin J (2009) New curcumin analogues exhibit enhanced growth-suppressive activity and inhibit AKT and signal transducer and activator of transcription 3 phosphorylation in breast and prostate cancer cells. Cancer Sci 100(9):1719–1727 Wang Y, Xiao J, Zhou H, Yang S, Wu X, Jiang C, Zhao Y, Liang D, Li X, Liang G (2011) A novel monocarbonyl analogue of curcumin, (1E,4E)-1,5-bis(2,3-dimethoxyphenyl)penta-1,4-dien-3-one, induced cancer cell H460 apoptosis via activation of endoplasmic reticulum stress signaling pathway. J Med Chem 54(11):3768–3778 Xiao J, Wang Y, Peng J, Guo L, Hu J, Cao M, Zhang X, Zhang H, Wang Z, Li X, Yang S, Yang H, Liang G (2012) A synthetic compound, 1,5-bis(2-methoxyphenyl)penta- 1,4-dien-3-one (B63), induces apoptosis and activates endoplasmic reticulum stress in non-small cell lung cancer cells. Int J Cancer 131(6):1455–1465 Liang G, Shao L, Wang Y, Zhao C, Chu Y, Xiao J, Zhao Y, Li X, Yang S (2009) Exploration and synthesis of curcumin analogues with improved structural stability both in vitro and in vivo as cytotoxic agents. Bioorg Med Chem 17(6):2623–2631 Trachootham D, Alexandre J, Huang P (2009) Targeting cancer cells by ROS-mediated mechanisms: a radical therapeutic approach? Nat Rev Drug Discov 8(7):579–591 Kumar B, Koul S, Khandrika L, Meacham RB, Koul HK (2008) Oxidative stress is inherent in prostate cancer cells and is required for aggressive phenotype. Cancer Res 68(6):1777–1785 Wagner BA, Evig CB, Reszka KJ, Buettner GR, Burns CP (2005) Doxorubicin increases intracellular hydrogen peroxide in PC3 prostate cancer cells. Arch Biochem Biophys 440(2):181–190 Miyajima A, Nakashima J, Yoshioka K, Tachibana M, Tazaki H, Murai M (1997) Role of reactive oxygen species in cis-dichlorodiammineplatinum-induced cytotoxicity on bladder cancer cells. Br J Cancer 76(2):206–210