142
K. SANGPHEAK ET AL.
25. Potter G, Butler P, Wanogho E. Substituted chalcones as 43. Dennington RD, Keith TA, Millam JM. GaussView 5.0. 8.
Gaussian Inc. 2008.
therapeutic compounds. U.S. Patent 6,787,672 B2; 2001.
26. Chauhan SS, Singh AK, Meena S, et al. Synthesis of novel
b-carboline based chalcones with high cytotoxic activity
against breast cancer cells. Bioorg Med Chem Lett 2014;
24:2820–4.
27. Nakhjavani M, Zarghi A, H Shirazi F. Cytotoxicity of selected
novel chalcone derivatives on human breast, lung and hep-
atic carcinoma cell lines. Iran J Pharm Res 2014;13:953–8.
28. 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.
44. 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.
45. Meeprasert A, Khuntawee W, Kamlungsua K, et al. Binding
pattern of the long acting neuraminidase inhibitor laninami-
vir towards influenza A subtypes H5N1 and pandemic H1N1.
J Mol Graph Model 2012;38:148–54.
46. Meeprasert A, Hannongbua S, Rungrotmongkol T. Key bind-
ing and susceptibility of NS3/4A serine protease
inhibitors against hepatitis C virus. J Chem Inf Model
2014;54:1208–17.
47. 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.
48. Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian 09
Revision A. 1. Wallingford (CT): Gaussian Inc.; 2009.
49. Duke R, Giese T, Gohlke H, et al. Amber 14. University of
California: San Francisco, CA; 2014.
50. Wang J, Wolf RM, Caldwell JW, et al. Development and
testing of a general amber force field. J Comput Chem
2004;25:1157–74.
51. 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.
52. Olsson MH, Søndergaard CR, Rostkowski M, Jensen JH.
PROPKA3: consistent treatment of internal and surface resi-
dues in empirical pKa predictions. J Chem Theory Comput
2011;7:525–37.
53. Jorgensen WL, Chandrasekhar J, Madura JD, et al.
Comparison of simple potential functions for simulating
liquid water. J Biol Chem 1983;79:926–35.
54. Ryckaert J-P, Ciccotti G, Berendsen HJ. Numerical integration
of the cartesian equations of motion of a system with con-
straints: molecular dynamics of n-alkanes. J Comput Phys
1977;23:327–41.
55. 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 meth-
ods. J Chem Phys 1993;99:8345–8.
56. 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.
57. Sangpheak W, Kicuntod J, Schuster R, et al. Physical proper-
ties and biological activities of hesperetin and naringenin in
complex with methylated beta-cyclodextrin. Beilstein J Org
Chem 2015;11:2763–73.
58. Boonyalai N, Sittikul P, Pradidphol N, Kongkathip N.
Biophysical and molecular docking studies of naphthoqui-
none derivatives on the ATPase domain of human topo-
isomerase II. Biomed Pharmacother 2013;67:122–8.
59. Siwek A, Sta˛czek 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.
29. Warmka JK, Solberg EL, Zeliadt NA, et al. Inhibition of mito-
gen 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.
30. Park S, Gwak J, Han SJ, Oh S. Cardamonin suppresses the
proliferation of colon cancer cells by promoting b-catenin
degradation. Biol Pharm Bull 2013;36:1040–4.
31. 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.
~
32. Echeverria C, Santibanez JF, Donoso-Tauda O, et al.
Structural antitumoral activity relationships of synthetic chal-
cones. Int J Mol Sci 2009;10:221–31.
33. 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.
34. Jandial DD, Blair CA, Zhang S, et al. Molecular targeted
approaches to cancer therapy and prevention using chal-
cones. Curr Cancer Drug Targets 2014;14:181–200.
35. 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.
36. 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.
37. Jeon K-H, Yu H-B, Kwak SY, et al. Synthesis and topoisomer-
ases inhibitory activity of heteroaromatic chalcones.
Bioorganic Med Chem 2016;24:5921–8.
38. Banday AH, Kulkarni VV, Hruby VJ. Design, synthesis, and
biological and docking studies of novel epipodophyllotox-
in–chalcone hybrids as potential anticancer agents. Med
Chem Comm 2015;6:94–104.
39. 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.
40. Ma Y-C, Wang Z-X, Jin S-J, et al. Dual inhibition of topoisom-
erase II and tyrosine kinases by the novel bis-fluoroquino-
lone chalcone-like derivative HMNE3 in human pancreatic
cancer cells. PLoS One 2016;11:e0162821.
41. Santos MB, Pinhanelli VC, Garcia MAR, et al. Antiproliferative
and pro-apoptotic activities of 20- and 40-aminochalcones
against tumor canine cells. Eur J Med Chem 2017;138:884–9.
42. Mahalapbutr P, Chusuth P, Kungwan N, et al. Molecular rec-
ognition of naphthoquinone-containing compounds against
human DNA topoisomerase IIa ATPase domain: a molecular
modeling study. J Mol Liq 2017;247:374–85.
60. Zhang Y, Wang L, Chen Y, Qing C. Anti-angiogenic activity
of salvicine. Pharm Biol 2013;51:1061–5.
€
61. Jarvinen TAH, Tanner M, Rantanen V, et al. Amplification and
deletion of topoisomerase IIa associate with ErbB-2