Plant-derived flavones as inhibitors of aurora B kinase and their quantitative structure-activity relationships

Chem Biol Drug Des. 2015 May;85(5):574-85. doi: 10.1111/cbdd.12445. Epub 2014 Oct 28.

Abstract

Although several plant-derived flavones inhibit aurora B kinase (aurB), quantitative relationships between the structural properties of plant-derived flavones and their inhibitory effects on aurB remain unclear. In this report, these quantitative structure-activity relationships were obtained. For quercetagetin, found in the Eriocaulon species, showing the best IC50 value among the flavone derivatives tested in this report, further biological tests were performed using cell-based assays, including Western blot analysis, flow cytometry, and immunofluorescence microscopy. In vitro cellular experiments demonstrated that quercetagetin inhibits aurB. The molecular-binding mode between quercetagetin and aurB was elucidated using in silico docking. Quercetagetin binds to aurB, aurA, and aurC and prevents the active phosphorylation of all three aurora kinases. In addition, quercetagetin triggers mitotic arrest and caspase-mediated apoptosis. These observations suggest that quercetagetin is an aurora kinase inhibitor. Induction of mitosis-associated tumor cell death by quercetagetin is a promising strategy for developing novel chemotherapeutic anticancer agents.

Keywords: aurora B kinase; flavone; flow cytometry; immunofluorescence microscopy; in silico docking; quantitative structure-activity relationship; quercetagetin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Apoptosis / drug effects
  • Aurora Kinase A / antagonists & inhibitors
  • Aurora Kinase A / metabolism
  • Aurora Kinase B / antagonists & inhibitors*
  • Aurora Kinase B / metabolism
  • Aurora Kinase C / antagonists & inhibitors
  • Aurora Kinase C / metabolism
  • Binding Sites
  • Chromones / chemistry
  • Chromones / isolation & purification
  • Chromones / toxicity
  • Eriocaulaceae / chemistry
  • Eriocaulaceae / metabolism
  • Flavones / chemistry*
  • Flavones / isolation & purification
  • Flavones / toxicity
  • G2 Phase Cell Cycle Checkpoints / drug effects
  • HCT116 Cells
  • Humans
  • M Phase Cell Cycle Checkpoints / drug effects
  • Microscopy, Fluorescence
  • Molecular Docking Simulation
  • Phosphorylation / drug effects
  • Protein Kinase Inhibitors / chemistry*
  • Protein Kinase Inhibitors / isolation & purification
  • Protein Kinase Inhibitors / toxicity
  • Protein Structure, Tertiary
  • Quantitative Structure-Activity Relationship*

Substances

  • Chromones
  • Flavones
  • Protein Kinase Inhibitors
  • Aurora Kinase A
  • Aurora Kinase B
  • Aurora Kinase C
  • flavone
  • quercetagetin