Synthesis and evaluation of (+)-decursin derivatives as inhibitors of the Wnt/β-catenin pathway

Bioorg Med Chem Lett. 2016 Aug 1;26(15):3529-32. doi: 10.1016/j.bmcl.2016.06.029. Epub 2016 Jun 11.

Abstract

We synthesized (+)-decursin derivatives substituted with cinnamoyl- and phenyl propionyl groups originating from (+)-CGK062 and screened them using a cell-based assay to detect relative luciferase reporter activity. Of this series, compound 8b, in which a 3-acetoxy cinnamoyl group was introduced, most potently inhibited (97.0%) the Wnt/β-catenin pathway. Specifically, compound 8b dose-dependently inhibited Wnt3a-induced expression of the β-catenin response transcription (CRT) and increased β-catenin degradation in HEK293 reporter cells. Furthermore, compound 8b suppressed expression of the downstream β-catenin target genes cyclin D1 and c-myc and suppressed PC3 cell growth in a concentration-dependent manner.

Keywords: Cinnamoyl decursin; Phenylpropionyl decursin; Prostate cancer; Protein degradation; Wnt/β-catenin pathway.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzopyrans / chemical synthesis
  • Benzopyrans / chemistry
  • Benzopyrans / pharmacology*
  • Butyrates / chemical synthesis
  • Butyrates / chemistry
  • Butyrates / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • HEK293 Cells
  • Humans
  • Molecular Structure
  • Stereoisomerism
  • Structure-Activity Relationship
  • Wnt Proteins / antagonists & inhibitors*
  • Wnt Proteins / metabolism
  • beta Catenin / antagonists & inhibitors*
  • beta Catenin / metabolism

Substances

  • Benzopyrans
  • Butyrates
  • Wnt Proteins
  • beta Catenin
  • decursin