A new synthetic 2'-hydroxy-2,4,6-trimethoxy-5',6'-naphthochalcone induces G2/M cell cycle arrest and apoptosis by disrupting the microtubular network of human colon cancer cells

Cancer Letters

Volumn 354, Issue 2, 2014, Pages 348-354

  Lee, Jong Min ^a   Lee, Mi So ^a   Koh, Dongsoo ^b   Lee, Young Han ^a   Lim, Yoongho ^a   Shin, Soon Young ^a  

^a Konkuk University   (South Korea)

^b Dongduk Women's University   (South Korea)

Author keywords

2' Hydroxy 2,4,6 trimethoxy 5',6' naphthochalcone; Apoptosis; Caspase 2; G2 M arrest; Tubulin polymerization

Indexed keywords

2' HYDROXY 2,3 DIMETHOXY 5',6' NAPHTHOCHALCONE; 2' HYDROXY 2,4 DIMETHOXY 3',4' NAPHTHOCHALCONE; 2' HYDROXY 2,4 DIMETHOXY 5',6' NAPHTHOCHALCONE; 2' HYDROXY 2,4,6 TRIMETHOXY 3',4' NAPHTHOCHALCONE; 2' HYDROXY 2,4,6 TRIMETHOXY 5',6' NAPHTHOCHALCONE; 5,6 NAPHTHOFLAVONE; CASPASE 2; CASPASE 3; CASPASE 7; CASPASE 9; CHALCONE DERIVATIVE; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE; PROTEIN BID; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; CHALCONE;

APOPTOSIS; ARTICLE; CANCER CELL; CANCER INHIBITION; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CELL CYCLE PROGRESSION; CELL DISRUPTION; CELL VIABILITY; CLONOGENESIS; COLON CANCER; CONTROLLED STUDY; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVATION; G2 PHASE CELL CYCLE CHECKPOINT; HUMAN; HUMAN CELL; MICROTUBULE ASSEMBLY; MOLECULAR MECHANICS; PROTEIN CLEAVAGE; SW620 CELL; ANALOGS AND DERIVATIVES; COLONIC NEOPLASMS; DRUG EFFECTS; HCT116 CELL LINE; M PHASE CELL CYCLE CHECKPOINT; MICROTUBULE; PATHOLOGY; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL LINE, TUMOR; CHALCONE; CHALCONES; COLONIC NEOPLASMS; G2 PHASE CELL CYCLE CHECKPOINTS; HCT116 CELLS; HUMANS; M PHASE CELL CYCLE CHECKPOINTS; MICROTUBULES;

EID: 84907989914     PISSN: 03043835     EISSN: 18727980     Source Type: Journal    
DOI: 10.1016/j.canlet.2014.08.041     Document Type: Article

References (41)

1. Harborne J.B., Williams C.A. Advances in flavonoid research since 1992. Phytochemistry 2000, 55:481-504.
2. Pietta P.G. Flavonoids as antioxidants. J. Nat. Prod 2000, 63:1035-1042.
3. Yao L.H., Jiang Y.M., Shi J., Tomas-Barberan F.A., Datta N., Singanusong R., et al. Flavonoids in food and their health benefits. Plant Foods Hum. Nutr 2004, 59:113-122.
4. Bravo L. Polyphenols: chemistry, dietary sources, metabolism, and nutritional significance. Nutr. Rev 1998, 56:317-333.
5. Orlikova B., Tasdemir D., Golais F., Dicato M., Diederich M. Dietary chalcones with chemopreventive and chemotherapeutic potential. Genes Nutr 2011, 6:125-147.
6. Dimmock J.R., Elias D.W., Beazely M.A., Kandepu N.M. Bioactivities of chalcones. Curr. Med. Chem 1999, 6:1125-1149.
7. Zhang E.H., Wang R.F., Guo S.Z., Liu B. An update on antitumor activity of naturally occurring chalcones. Evid. Based Complement. Alternat. Med 2013, 2013:815621.
8. Yadav V.R., Prasad S., Sung B., Aggarwal B.B. The role of chalcones in suppression of NF-kappaB-mediated inflammation and cancer. Int. Immunopharmacol 2011, 11:295-309.
9. Ducki S., Forrest R., Hadfield J.A., Kendall A., Lawrence N.J., McGown A.T., et al. Potent antimitotic and cell growth inhibitory properties of substituted chalcones. Bioorg. Med. Chem. Lett 1998, 8:1051-1056.
10. Loa J., Chow P., Zhang K. Studies of structure-activity relationship on plant polyphenol-induced suppression of human liver cancer cells. Cancer Chemother. Pharmacol 2009, 63:1007-1016.
11. Shin S.Y., Kim J.H., Yoon H., Choi Y.K., Koh D., Lim Y., et al. Novel antimitotic activity of 2-hydroxy-4-methoxy-2',3'-benzochalcone (HymnPro) through the inhibition of tubulin polymerization. J. Agric. Food Chem 2013, 61:12588-12597.
12. Hwang D., Hyun J., Jo G., Koh D., Lim Y. Synthesis and complete assignment of NMR data of 20 chalcones. Magn. Reson. Chem 2011, 49:41-45.
13. Franken N.A., Rodermond H.M., Stap J., Haveman J., van Bree C. Clonogenic assay of cells in vitro. Nat. Protoc 2006, 1:2315-2319.
14. Hwang D., Shin S.Y., Lee Y., Hyun J., Yong Y., Park J.C., et al. A compound isolated from Schisandra chinensis induces apoptosis. Bioorg. Med. Chem. Lett 2011, 21:6054-6057.
15. Shin S.Y., Kim J.H., Lee J.H., Lim Y., Lee Y.H. 2'-Hydroxyflavanone induces apoptosis through Egr-1 involving expression of Bax, p21, and NAG-1 in colon cancer cells. Mol. Nutr. Food Res 2012, 56:761-774.
16. Yue Q.X., Liu X., Guo D.A. Microtubule-binding natural products for cancer therapy. Planta Med 2010, 76:1037-1043.
17. Jordan M.A., Wilson L. Microtubules as a target for anticancer drugs. Nat. Rev. Cancer 2004, 4:253-265.
18. Altmann K.H., Gertsch J. Anticancer drugs from nature - natural products as a unique source of new microtubule-stabilizing agents. Nat. Prod. Rep 2007, 24:327-357.
19. McManus K.J., Hendzel M.J. The relationship between histone H3 phosphorylation and acetylation throughout the mammalian cell cycle. Biochem. Cell Biol 2006, 84:640-657.
20. Wu R., Ding W., Liu T., Zhu H., Hu Y., Yang B., et al. XN05, a novel synthesized microtubule inhibitor, exhibits potent activity against human carcinoma cells in vitro. Cancer Lett 2009, 285:13-22.
21. Mollinedo F., Gajate C. Microtubules, microtubule-interfering agents and apoptosis. Apoptosis 2003, 8:413-450.
22. Andree H.A., Reutelingsperger C.P., Hauptmann R., Hemker H.C., Hermens W.T., Willems G.M. Binding of vascular anticoagulant alpha (VAC alpha) to planar phospholipid bilayers. J. Biol. Chem 1990, 265:4923-4928.
23. Vermes I., Haanen C., Steffens-Nakken H., Reutelingsperger C. A novel assay for apoptosis. Flow cytometric detection of phosphatidylserine expression on early apoptotic cells using fluorescein labelled Annexin V. J. Immunol. Methods 1995, 184:39-51.
24. Gavrieli Y., Sherman Y., Ben-Sasson S.A. Identification of programmed cell death in situ via specific labeling of nuclear DNA fragmentation. J. Cell Biol 1992, 119:493-501.
25. Danial N.N., Korsmeyer S.J. Cell death: critical control points. Cell 2004, 116:205-219.
26. Ho L.H., Read S.H., Dorstyn L., Lambrusco L., Kumar S. Caspase-2 is required for cell death induced by cytoskeletal disruption. Oncogene 2008, 27:3393-3404.
27. Guo Y., Srinivasula S.M., Druilhe A., Fernandes-Alnemri T., Alnemri E.S. Caspase-2 induces apoptosis by releasing proapoptotic proteins from mitochondria. J. Biol. Chem 2002, 277:13430-13437.
28. Wang Y.F., Chen C.Y., Chung S.F., Chiou Y.H., Lo H.R. Involvement of oxidative stress and caspase activation in paclitaxel-induced apoptosis of primary effusion lymphoma cells. Cancer Chemother. Pharmacol 2004, 54:322-330.
29. Kim B.M., Rode A.B., Han E.J., Hong I.S., Hong S.H. 5-Phenylselenyl- and 5-methylselenyl-methyl-2'-deoxyuridine induce oxidative stress, DNA damage, and caspase-2-dependent apoptosis in cancer cells. Apoptosis 2012, 17:200-216.
30. Lassus P., Opitz-Araya X., Lazebnik Y. Requirement for caspase-2 in stress-induced apoptosis before mitochondrial permeabilization. Science 2002, 297:1352-1354.
31. Cuenin S., Tinel A., Janssens S., Tschopp J. p53-induced protein with a death domain (PIDD) isoforms differentially activate nuclear factor-kappaB and caspase-2 in response to genotoxic stress. Oncogene 2008, 27:387-396.
32. da Silva J., Herrmann S.M., Heuser V., Peres W., Possa Marroni N., Gonzalez-Gallego J., et al. Evaluation of the genotoxic effect of rutin and quercetin by comet assay and micronucleus test. Food Chem. Toxicol 2002, 40:941-947.
33. Shin S.Y., Hyun J., Yu J.R., Lim Y., Lee Y.H. 5-Methoxyflavanone induces cell cycle arrest at the G2/M phase, apoptosis and autophagy in HCT116 human colon cancer cells. Toxicol. Appl. Pharmacol 2011, 254:288-298.
34. Kinner A., Wu W., Staudt C., Iliakis G. Gamma-H2AX in recognition and signaling of DNA double-strand breaks in the context of chromatin. Nucleic Acids Res 2008, 36:5678-5694.
35. Smith J., Tho L.M., Xu N., Gillespie D.A. The ATM-Chk2 and ATR-Chk1 pathways in DNA damage signaling and cancer. Adv. Cancer Res 2010, 108:73-112.
36. Vousden K.H., Lane D.P. p53 in health and disease. Nat. Rev. Mol. Cell Biol 2007, 8:275-283.
37. Miyashita T., Krajewski S., Krajewska M., Wang H.G., Lin H.K., Liebermann D.A., et al. Tumor suppressor p53 is a regulator of bcl-2 and bax gene expression in vitro and in vivo. Oncogene 1994, 9:1799-1805.
38. Selvakumaran M., Lin H.K., Miyashita T., Wang H.G., Krajewski S., Reed J.C., et al. Immediate early up-regulation of bax expression by p53 but not TGF beta 1: a paradigm for distinct apoptotic pathways. Oncogene 1994, 9:1791-1798.
39. Chen C.R., Wang W., Rogoff H.A., Li X., Mang W., Li C.J. Dual induction of apoptosis and senescence in cancer cells by Chk2 activation: checkpoint activation as a strategy against cancer. Cancer Res 2005, 65:6017-6021.
40. Carlessi L., Buscemi G., Larson G., Hong Z., Wu J.Z., Delia D. Biochemical and cellular characterization of VRX0466617, a novel and selective inhibitor for the checkpoint kinase Chk2. Mol. Cancer Ther 2007, 6:935-944.
41. Manchado E., Guillamot M., Malumbres M. Killing cells by targeting mitosis. Cell Death Differ 2012, 19:369-377.