Chromenylchalcones showing cytotoxicity on human colon cancer cell lines and in silico docking with aurora kinases

Bioorg Med Chem. 2013 Jul 15;21(14):4250-8. doi: 10.1016/j.bmc.2013.04.086. Epub 2013 May 15.

Abstract

Due to toxicity problems, various plant-derived compounds have been screened to find the chemotherapeutic agents. As anticancer therapeutic agents, chalcones have advantages such as poor interaction with DNA and low risk of mutagenesity. Chromenones show anticancer activities too. Therefore, hybrids of chalcone and chromenone may be potent chemotherapeutic agents. We prepared 16 synthetic chromenylchalcones and applied a clonogenic long-term survival assay method for them on HCT116 human colorectal cancer cell lines. One of chromenylchalcones tested here, chromenylchalcone 11, showed IC50 of 93.1nM which can be competed with the IC50 values of well-known flavonoids such as catechin gallate and epicatechin gallate. Further biological experiments including cell cycle analysis, apoptosis assay, Western blot analysis, and immunofluorescent microscopy were carried out for this compound. In addition, in vitro kinases binding assay performed to explain its molecular mechanism demonstrated the compound inhibited aurora kinases. The binding modes between chromenylchalcone 11 and aurora kinases were elucidated using in silico docking experiments. These findings could be used for designing cancer therapeutic or preventive plant-derived chromenylchalcone agents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Aurora Kinases / chemistry*
  • Aurora Kinases / metabolism
  • Benzopyrans / chemical synthesis*
  • Benzopyrans / metabolism
  • Benzopyrans / pharmacology
  • Binding Sites
  • Blotting, Western
  • Catechin / chemistry
  • Catechin / pharmacology
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Chalcones / chemical synthesis*
  • Chalcones / chemistry
  • Chalcones / metabolism
  • Chalcones / pharmacology
  • Colonic Neoplasms / drug therapy*
  • Humans
  • Inhibitory Concentration 50
  • Protein Binding

Substances

  • 1-(6-methoxy-2H-chromen-3-yl)-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-one
  • Antineoplastic Agents
  • Benzopyrans
  • Chalcones
  • Catechin
  • Aurora Kinases