Long residence times revealed by Aurora A kinase-targeting fluorescent probes derived from inhibitors MLN8237 and VX-689

Chembiochem. 2014 Feb 10;15(3):443-50. doi: 10.1002/cbic.201300613. Epub 2014 Jan 8.

Abstract

We report the development of three fluorescent probes for protein kinase Aurora A that are derived from the well-known inhibitors MLN8237 and VX-689 (MK-5108). Two of these probes target the ATP site of Aurora A, and one targets simultaneously the ATP and substrate sites of the kinase. The probes were tested in an assay with fluorescence polarisation/anisotropy readout, and we demonstrated slow association kinetics and long residence time of the probes (kon 10(5)-10(7) M(-1) s(-1), koff 10(-3)-10(-4) s(-1); residence time 500-3000 s). The presence of the Aurora A activator TPX2 caused a significant reduction in the on-rate and increase in the off-rate of fluorescent probes targeting ATP site. These observations were supported by Aurora A inhibition assays with MLN8237 and VX-689. Overall, our results emphasise the importance of rational design of experiments with these compounds and correct interpretation of the obtained data.

Keywords: Aurora A; fluorescent probes; inhibitors; kinetics; protein kinases; residence time.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aurora Kinase A / antagonists & inhibitors*
  • Aurora Kinase A / metabolism
  • Azepines / chemistry*
  • Azepines / metabolism
  • Cyclohexanecarboxylic Acids / chemistry*
  • Cyclohexanecarboxylic Acids / metabolism
  • Fluorescence Polarization
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Fluorescent Dyes / metabolism
  • Half-Life
  • Kinetics
  • Microtubule-Associated Proteins / chemistry
  • Microtubule-Associated Proteins / metabolism
  • Protein Binding
  • Protein Kinase Inhibitors / chemical synthesis
  • Protein Kinase Inhibitors / chemistry*
  • Protein Kinase Inhibitors / metabolism
  • Pyrimidines / chemistry*
  • Pyrimidines / metabolism
  • Thermodynamics
  • Thiazoles / chemistry*
  • Thiazoles / metabolism

Substances

  • 4-(3-chloro-2-fluorophenoxy)-1-((6-(1,3-thiazol-2-ylamino)pyridin to 2-yl)methyl) cyclohexanecarboxylic acid
  • Azepines
  • Cyclohexanecarboxylic Acids
  • Fluorescent Dyes
  • MLN 8237
  • Microtubule-Associated Proteins
  • Protein Kinase Inhibitors
  • Pyrimidines
  • Thiazoles
  • Aurora Kinase A