Efficient synthesis of new phenanthridine Wnt/β-catenin signaling pathway agonists

Eur J Med Chem. 2018 Sep 5:157:1491-1499. doi: 10.1016/j.ejmech.2018.08.064. Epub 2018 Aug 28.

Abstract

Previously, HLY78, a lycorine derivative, was identified as the first Wnt/β-catenin signaling agonist through binding to the DAX domain of Axin, a scaffold of Wnt/β-catenin complex. In this study, to obtain more potent Wnt/β-catenin agonist, the structure optimization of HLY78 was carried out by design and synthesis of six phenanthridine derivatives, which afforded five active ones. In particular, 8,9-bis((1,3-dimethyl-1H-pyrazol)methoxy)-5-ethyl-4-methyl-5,6-dihydrophenanthridine showed the most potent activity (0.15/μM) that was increased nearly 30 times as that of the lead HLY78. These compounds may be valuable in future pharmacological or biological studies.

Keywords: Phenanthridine derivatives; Structural optimization; Wnt/β-catenin signaling agonist.

MeSH terms

  • Animals
  • Cells, Cultured
  • Dose-Response Relationship, Drug
  • HEK293 Cells
  • Humans
  • Mice
  • Models, Molecular
  • Molecular Structure
  • Phenanthridines / chemical synthesis*
  • Phenanthridines / chemistry
  • Phenanthridines / pharmacology*
  • Structure-Activity Relationship
  • Wnt Proteins / agonists*
  • Wnt Proteins / metabolism
  • Wnt Signaling Pathway / drug effects*
  • beta Catenin / agonists*
  • beta Catenin / metabolism

Substances

  • CTNNB1 protein, human
  • Phenanthridines
  • Wnt Proteins
  • beta Catenin