Journal of Industrial and Engineering Chemistry, Vol.56, 258-269, December, 2017
Synthetic polyphenol compounds inhibit b-catenin/Tcf signaling: Structure-activity relationship
E-mail:
Activated b-catenin/T-cell factor signaling has been shown to be involved in human carcinogenesis. Here, the inhibitory effects of various synthetic naphthoflavones and napthochalcones on β-catenin/Tcf signaling in β-catenin overexpressing-cells were investigated and compared. The naphthoflavones with a β-angular pattern (5,6-benzoflavone series) resulted in a more potent inhibitory activity than those with an a-angular pattern (7,8-benzoflavone series), indicating that the direction of the naphthyl ring is an important determinant of inhibitory activity. This result is in accordance with the napthochalcone derivatives. Moreover, in silico docking results supported our in vitro biological results.
- Mareel M, Boterberg T, Noe V, Van Hoorde L, Vermeulen S, Bruyneel E, Bracke M, J. Cell. Physiol., 173, 271 (1997)
- Bullions LC, Levine AJ, Curr. Opin. Oncol., 10, 81 (1998)
- Aberle H, Bauer A, Stappert J, Kispert A, Kemler R, Embo J., 16, 3797 (1997)
- Rubinfeld B, Albert I, Porfiri E, Fiol C, Munemitsu S, Polakis P, Science, 272(5264), 1023 (1996)
- He TC, Sparks AB, Rago C, Hermeking H, Zawel L, da Costa LT, Morin PJ, Vogelstein B, Kinzler KW, Science, 281(5382), 1509 (1998)
- Tetsu O, McCormick F, Nature, 398, 422 (1999)
- Mann B, Gelos M, Siedow A, Hanski ML, Gratchev A, Ilyas M, Bodmer WF, Moyer MP, Riecken EO, Buhr HJ, Hanski C, Proc. Natl. Acad. Sci., 96, 1603 (1999)
- Morin PJ, Sparks AB, Korinek V, Barker N, Clevers H, Vogelstein B, Kinzler KW, Science, 275(5307), 1787 (1997)
- Fujie H, Moriya K, Shintani Y, Tsutsumi T, Takayama T, Makuuchi M, Kimura S, Koike K, Hepatol. Res., 20, 39 (2011)
- Woo DK, Kim HS, Lee HS, Kang YH, Yang HK, Kim WH, Int. J. Cancer, 95, 108 (2001)
- Nakatsuru S, Yanagisawa A, Ichii S, Tahara E, Kato Y, Nakamura Y, Horii A, Hum. Mol. Genet., 1, 559 (1992)
- Clements WM, Wang J, Sarnaik A, Kim OJ, MacDonald J, Fenoglio-Preiser C, Groden J, Lowy AM, Cancer Res., 62, 3503 (2002)
- Powell SM, Zilz N, Beazer-Barclay Y, Bryan TM, Hamilton SR, Thibodeau SN, Vogelstein B, Kinzler KW, Nature, 359, 235 (1992)
- Park CH, Chang JY, Hahm ER, Park S, Kim HK, Yang CH, Biochem. Biophys. Res. Commun., 328(1), 227 (2005)
- Park S, Chun S, Biochim. Biophys. Acta., 1810, 1340 (2011)
- Chen CC, Chow MP, Huang WC, Lin YC, Chang YJ, Mol. Pharmacol., 66, 683 (2004)
- Halake K, Birajdar M, Lee J, J. Ind. Eng. Chem., 35, 1 (2016)
- Joo KHLCG, Park C, Joo IW, Choe TB, Lee BC, J. Ind. Eng. Chem., 18, 263 (2012)
- Hwang YY, Shin DC, Nam YS, Cho BK, J. Ind. Eng. Chem., 18(4), 1412 (2012)
- Kim YH, Choi SJ, Park HJ, Lee JH, J. Ind. Eng. Chem., 20(4), 1834 (2014)
- Yao N, Song A, Wang X, Dixon S, Lam KS, J. Comb. Chem., 9, 668 (2007)
- Hwang D, Jo G, Hyun J, Lee SD, Koh D, Lim Y, Magn. Reson. Chem., 50, 62 (2012)
- Cardona ML, Fernandez MI, Garcia MB, Pedro JR, Tetrahedron, 42, 2725 (1986)
- Jo G, Hyun J, Hwang D, Lee YH, Koh D, Lim Y, Magn. Reson. Chem., 49, 374 (2011)
- Park S, Choi J, J. Cell Biochem., 110, 1376 (2010)
- Shin SY, Woo Y, Hyun J, Yong Y, Koh D, Lee YH, Lim Y, Bioorg. Med. Chem. Lett., 21, 6036 (2011)
- Shin SY, Jung H, Ahn S, Hwang D, Yoon H, Hyun J, Yong Y, Cho HJ, Koh D, Lee YH, Lim Y, Bioorg. Med. Chem. Lett., 22, 1809 (2014)
- Koh D, Acta. Cryst., E70, o1034 (2014)
- Laskowski RA, Swindells MB, J. Chem. Inf. Model., 51, 2778 (2011)
- Yong Y, Shin SY, Jung Y, Jung H, Ahn S, Chong Y, Lim Y, Appl. Biol. Chem., 58, 13 (2015)
- Hwang D, Hyun J, Jo G, Koh D, Lim Y, Magn. Reson. Chem., 49, 41 (2011)
- Radwan AA, Al-Mohanna F, Alanazi FK, Manogaran PS, Al-Dhfyan A, Bioorg. Med. Chem. Lett., 26, 1664 (2016)
- Poy F, Lepourcelet M, Shivdasani RA, Eck MJ, Nat. Struct. Biol., 8, 1053 (2001)
- Fasolini M, Wu X, Flocco M, Trosset JY, Oppermann U, Knapp S, J. Biol. Chem., 278, 21092 (2003)
- Graham TA, Ferkey DM, Mao F, Kimelman D, Xu W, Nat. Struct. Biol., 8, 1048 (2001)
- Park CH, Hahm ER, Lee JH, Jung KC, Yang CH, Biochem. Biophys. Res. Commun., 331(4), 1222 (2005)
- Park CH, Chang JY, Hahm ER, Park S, Kim HK, Yang CH, Febs Lett., 579, 2965 (2005)
- Lee JH, Park CH, Jung KC, Rhee HS, Yang CH, Biochem. Biophys. Res. Commun., 335(3), 771 (2005)
- Dihlmann S, Siermann A, von Knebel Doeberitz M, Oncogene, 20, 645 (2001)
- Jaiswal AS, Marlow BP, Gupta N, Narayan S, Oncogene, 21, 8414 (2002)
- Dashwood WM, Orner GA, Dashwood RH, Biochem. Biophys. Res. Commun., 296(3), 584 (2002)
- Park S, Nutrients, 7, 8987 (2015)
- Hahne G, Grossmann TN, Bioorg. Med. Chem., 21, 4020 (2013)
- Inagaki K, Dijt FJ, Lempers EL, Reedijk J, Inorg. Chem., 27, 382 (1988)
- Ronova IA, Dubrovina LV, Kovalevskii AY, Hamciuc C, Bruma M, Russ. Chem. B, 47, 1248 (1998)