2,902
Views
12
CrossRef citations to date
0
Altmetric
Research Paper

Computational screening of chalcones acting against topoisomerase IIα and their cytotoxicity towards cancer cell lines

, , , , , , , , , , & show all
Pages 134-143 | Received 02 Jun 2018, Accepted 29 Jul 2018, Published online: 04 Nov 2018

References

  • World Health Organization (WHO). WHO cancer 2017. Available from: http://www.who.int/mediacentre/factsheets/fs297/en/; 2017.
  • Gibbs JB. Mechanism-based target identification and drug discovery in cancer research. Science 2000;287:1969–73.
  • Nitiss JL. Targeting DNA topoisomerase II in cancer chemotherapy. Nat Rev Cancer 2009;9:338.
  • Hande KR. Topoisomerase II inhibitors. Update Cancer Ther 2008;3:13–26.
  • Heck M, Earnshaw WC. Topoisomerase II: a specific marker for cell proliferation. J Cell Biol 1986;103:2569–81.
  • Wendorff TJ, Schmidt BH, Heslop P, et al. The structure of DNA-bound human topoisomerase II alpha: conformational mechanisms for coordinating inter-subunit interactions with DNA cleavage. J Mol Biol 2012;424:109–24.
  • Robinson MJ, Martin B, Gootz T, et al. Effects of quinolone derivatives on eukaryotic topoisomerase II. A novel mechanism for enhancement of enzyme-mediated DNA cleavage. J Biol Chem 1991;266:14585–92.
  • Classen S, Olland S, Berger JM. Structure of the topoisomerase II ATPase region and its mechanism of inhibition by the chemotherapeutic agent ICRF-187. Proc Natl Acad Sci USA 2003;100:10629–34.
  • Wu T, Wang Y, Yuan Y. Antiviral activity of topoisomerase II catalytic inhibitors against Epstein-Barr virus. Antiviral Res 2014;107:95–101.
  • Cai Y-J, Lu J-J, Zhu H, et al. Salvicine triggers DNA double-strand breaks and apoptosis by GSH-depletion-driven H2O2 generation and topoisomerase II inhibition. Free Radic Biol Med 2008;45:627–35.
  • Pastor N, Domínguez I, Orta ML, et al. The DNA topoisomerase II catalytic inhibitor merbarone is genotoxic and induces endoreduplication. Mutat Res 2012;738–739:45–51.
  • Baviskar AT, Amrutkar SM, Trivedi N, et al. Switch in site of inhibition: a strategy for structure-based discovery of human topoisomerase IIα catalytic inhibitors. ACS Med Chem Lett 2015;6:481–5.
  • Fortune JM, Osheroff N. Merbarone inhibits the catalytic activity of human topoisomerase IIalpha by blocking DNA cleavage. J Biol Chem 1998;273:17643–50.
  • Meng L-h, Zhang J-s, Ding J. Salvicine, a novel DNA topoisomerase II inhibitor, exerting its effects by trapping enzyme-DNA cleavage complexes. Biochem Pharmacol 2001;62:733–41.
  • Kesharwani RK, Misra K. Prediction of binding site for curcuminoids at human topoisomerase IIα protein; an in silico approach. Curr Sci 2011;101:1060–5.
  • Meng L-h, Ding J. Salvicine, a novel topoisomerase II inhibitor, exerts its potent anticancer activity by ROS generation. Acta Pharmacol Sin 2007;28:1460–5.
  • Hu C-X, Zuo Z-L, Xiong B, et al. Salvicine functions as novel topoisomerase II poison by binding to ATP pocket. Mol Pharmacol 2006;70:1593–601.
  • Abu N, Ho WY, Yeap SK, et al. The flavokawains: uprising medicinal chalcones. Cancer Cell Int 2013;13:102.
  • Haraguchi H, Ishikawa H, Mizutani K, et al. Antioxidative and superoxide scavenging activities of retrochalcones in Glycyrrhiza inflata. Bioorganic Med Chem 1998;6:339–47.
  • Akihisa T, Tokuda H, Ukiya M, et al. Chalcones, coumarins, and flavanones from the exudate of Angelica keiskei and their chemopreventive effects. Cancer Lett 2003;201:133–7.
  • Chopra PG. Chalcones: a brief review. Int J Res Eng Appl Sci 2016;6:173–85.
  • Won S-J, Liu C-T, Tsao L-T, et al. Synthetic chalcones as potential anti-inflammatory and cancer chemopreventive agents. Eur J Med Chem 2005;40:103–12.
  • Nowakowska Z. A review of anti-infective and anti-inflammatory chalcones. Eur J Med Chem 2007;42:125–37.
  • Mahapatra DK, Bharti SK, Asati V. Anti-cancer chalcones: structural and molecular target perspectives. Eur J Med Chem 2015;98:69–114.
  • Potter G, Butler P, Wanogho E. Substituted chalcones as therapeutic compounds. U.S. Patent 6,787,672 B2; 2001.
  • Chauhan SS, Singh AK, Meena S, et al. Synthesis of novel β-carboline based chalcones with high cytotoxic activity against breast cancer cells. Bioorg Med Chem Lett 2014;24:2820–4.
  • Nakhjavani M, Zarghi A, H Shirazi F. Cytotoxicity of selected novel chalcone derivatives on human breast, lung and hepatic carcinoma cell lines. Iran J Pharm Res 2014;13:953–8.
  • Ducki S, Mackenzie G, Greedy B, et al. Combretastatin-like chalcones as inhibitors of microtubule polymerisation. Part 2: Structure-based discovery of alpha-aryl chalcones. Bioorg Med Chem Lett 2009;17:7711–22.
  • Warmka JK, Solberg EL, Zeliadt NA, et al. Inhibition of mitogen activated protein kinases increases the sensitivity of A549 lung cancer cells to the cytotoxicity induced by a kava chalcone analog. Biochem Biophys Res Commun 2012;424:488–92.
  • Park S, Gwak J, Han SJ, Oh S. Cardamonin suppresses the proliferation of colon cancer cells by promoting β-catenin degradation. Biol Pharm Bull 2013;36:1040–4.
  • Wei H, Zhang X, Wu G, et al. Chalcone derivatives from the fern Cyclosorus parasiticus and their anti-proliferative activity. Food Chem Toxicol 2013;60:147–52.
  • Echeverria C, Santibañez JF, Donoso-Tauda O, et al. Structural antitumoral activity relationships of synthetic chalcones. Int J Mol Sci 2009;10:221–31.
  • Vogel S, Ohmayer S, Brunner G, Heilmann J. Natural and non-natural prenylated chalcones: synthesis, cytotoxicity and anti-oxidative activity. Bioorg Med Chem 2008;16:4286–93.
  • Jandial DD, Blair CA, Zhang S, et al. Molecular targeted approaches to cancer therapy and prevention using chalcones. Curr Cancer Drug Targets 2014;14:181–200.
  • Gaur R, Mishra L. Synthesis and characterization of Ru(II)-DMSO-Cl-chalcone complexes: DNA binding, nuclease, and topoisomerase II inhibitory activity. Inorg Chem 2012;51:3059–70.
  • Kim S-H, Lee E, Baek KH, et al. Chalcones, inhibitors for topoisomerase I and cathepsin B and L, as potential anti-cancer agents. Bioorg Med Chem Lett 2013;23:3320–4.
  • Jeon K-H, Yu H-B, Kwak SY, et al. Synthesis and topoisomerases inhibitory activity of heteroaromatic chalcones. Bioorganic Med Chem 2016;24:5921–8.
  • Banday AH, Kulkarni VV, Hruby VJ. Design, synthesis, and biological and docking studies of novel epipodophyllotoxin–chalcone hybrids as potential anticancer agents. Med Chem Comm 2015;6:94–104.
  • Chinthala Y, Thakur S, Tirunagari S, et al. Synthesis, docking and ADMET studies of novel chalcone triazoles for anti-cancer and anti-diabetic activity. Eur J Med Chem 2015;93:564–73.
  • Ma Y-C, Wang Z-X, Jin S-J, et al. Dual inhibition of topoisomerase II and tyrosine kinases by the novel bis-fluoroquinolone chalcone-like derivative HMNE3 in human pancreatic cancer cells. PLoS One 2016;11:e0162821.
  • Santos MB, Pinhanelli VC, Garcia MAR, et al. Antiproliferative and pro-apoptotic activities of 2′- and 4′-aminochalcones against tumor canine cells. Eur J Med Chem 2017;138:884–9.
  • Mahalapbutr P, Chusuth P, Kungwan N, et al. Molecular recognition of naphthoquinone-containing compounds against human DNA topoisomerase IIα ATPase domain: a molecular modeling study. J Mol Liq 2017;247:374–85.
  • Dennington RD, Keith TA, Millam JM. GaussView 5.0. 8. Gaussian Inc. 2008.
  • Irwin JJ, Sterling T, Mysinger MM, et al. ZINC: a free tool to discover chemistry for biology. J Chem Inf Model 2012;52:1757–68.
  • Meeprasert A, Khuntawee W, Kamlungsua K, et al. Binding pattern of the long acting neuraminidase inhibitor laninamivir towards influenza A subtypes H5N1 and pandemic H1N1. J Mol Graph Model 2012;38:148–54.
  • Meeprasert A, Hannongbua S, Rungrotmongkol T. Key binding and susceptibility of NS3/4A serine protease inhibitors against hepatitis C virus. J Chem Inf Model 2014;54:1208–17.
  • Kaiyawet N, Rungrotmongkol T, Hannongbua S. Effect of halogen substitutions on dUMP to stability of thymidylate synthase/dUMP/mTHF ternary complex using molecular dynamics simulation. J Chem Inf Model 2013;53:1315–23.
  • Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian 09 Revision A. 1. Wallingford (CT): Gaussian Inc.; 2009.
  • Duke R, Giese T, Gohlke H, et al. Amber 14. University of California: San Francisco, CA; 2014.
  • Wang J, Wolf RM, Caldwell JW, et al. Development and testing of a general amber force field. J Comput Chem 2004;25:1157–74.
  • Duan Y, Wu C, Chowdhury S, et al. A point-charge force field for molecular mechanics simulations of proteins based on condensed-phase quantum mechanical calculations. J Comput Chem 2003;24:1999–2012.
  • Olsson MH, Søndergaard CR, Rostkowski M, Jensen JH. PROPKA3: consistent treatment of internal and surface residues in empirical pKa predictions. J Chem Theory Comput 2011;7:525–37.
  • Jorgensen WL, Chandrasekhar J, Madura JD, et al. Comparison of simple potential functions for simulating liquid water. J Biol Chem 1983;79:926–35.
  • Ryckaert J-P, Ciccotti G, Berendsen HJ. Numerical integration of the cartesian equations of motion of a system with constraints: molecular dynamics of n-alkanes. J Comput Phys 1977;23:327–41.
  • York DM, Darden TA, Pedersen LG. The effect of long-range electrostatic interactions in simulations of macromolecular crystals: A comparison of the Ewald and truncated list methods. J Chem Phys 1993;99:8345–8.
  • Cabrera M, Simoens M, Falchi G, et al. Synthetic chalcones, flavanones, and flavones as antitumoral agents: Biological evaluation and structure–activity relationships. Bioorganic Med Chem 2007;15:3356–67.
  • Sangpheak W, Kicuntod J, Schuster R, et al. Physical properties and biological activities of hesperetin and naringenin in complex with methylated beta-cyclodextrin. Beilstein J Org Chem 2015;11:2763–73.
  • Boonyalai N, Sittikul P, Pradidphol N, Kongkathip N. Biophysical and molecular docking studies of naphthoquinone derivatives on the ATPase domain of human topoisomerase II. Biomed Pharmacother 2013;67:122–8.
  • Siwek A, Stączek P, Wujec M, et al. Cytotoxic effect and molecular docking of 4-ethoxycarbonylmethyl-1-(piperidin-4-ylcarbonyl)-thiosemicarbazide—a novel topoisomerase II inhibitor. J Mol Model 2013;19:1319–24.
  • Zhang Y, Wang L, Chen Y, Qing C. Anti-angiogenic activity of salvicine. Pharm Biol 2013;51:1061–5.
  • Järvinen TAH, Tanner M, Rantanen V, et al. Amplification and deletion of topoisomerase IIα associate with ErbB-2 amplification and affect sensitivity to topoisomerase II inhibitor doxorubicin in breast cancer. Am J Pathol 2000;156:839–47.
  • Froelich-Ammon SJ, Osheroff N. Topoisomerase poisons: harnessing the dark side of enzyme mechanism. J Biol Chem 1995;270:21429–32.
  • Wang JC. DNA topoisomerases. Annu Rev Biochem 1985;54:665–97.
  • Järvinen T, Kononen J, Pelto-Huikko M, Isola J. Expression of topoisomerase IIalpha is associated with rapid cell proliferation, aneuploidy, and c-erbB2 overexpression in breast cancer. Am J Pathol 1996;148:2073.
  • Zhou Z, Zwelling LA, Kawakami Y, et al. Adenovirus-mediated human topoisomerase IIα gene transfer increases the sensitivity of etoposide-resistant human breast cancer cells. Cancer Res 1999;59:4618–24.
  • McLeod HL, Douglas F, Oates M, et al. Topoisomerase I and II activity in human breast, cervix, lung and colon cancer. Int J Cancer 1994;59:607–11.