In silico discovery of quinoxaline derivatives as novel LRP5/6-sclerostin interaction inhibitors

Bioorg Med Chem Lett. 2018 Apr 1;28(6):1116-1121. doi: 10.1016/j.bmcl.2018.01.050. Epub 2018 Feb 2.

Abstract

The Wnt/β-catenin signaling pathway is a key regulator of bone homeostasis. Sclerostin act as an extracellular inhibitor of canonical Wnt signaling through high-affinity binding to the Wnt co-receptor LRP5/6. Disruption of the interaction between LRP5/6 and sclerostin has been recognized as a therapeutic target for osteoporosis. We identified a quinoxaline moiety as a new small-molecule inhibitor of the LRP5/6-sclerostin interaction through pharmacophore-based virtual screening, docking simulations, and in vitro assays. Structure-activity relationship studies and binding mode hypotheses were used to optimize the scaffold and yield the compound BMD4503-2, which recovered the downregulated activity of the Wnt/β-catenin signaling pathway by competitive binding to the LRP5/6-sclerostin complex. Overall, this study showed that the optimized structure-based drug design was a promising approach for the development of small-molecule inhibitors of the LRP5/6-sclerostin interaction. A novel scaffold offered considerable insights into the structural basis for binding to LRP5/6 and disruption of the sclerostin-mediated inhibition of Wnt signaling.

Keywords: LRP5/6-sclerostin interaction; Osteoporosis; Structure-activity relationships; Virtual screening; Wnt/β-catenin signalling pathway.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adaptor Proteins, Signal Transducing
  • Bone Morphogenetic Proteins / antagonists & inhibitors*
  • Bone Morphogenetic Proteins / chemistry
  • Dose-Response Relationship, Drug
  • Drug Discovery*
  • Genetic Markers
  • Humans
  • Low Density Lipoprotein Receptor-Related Protein-5 / antagonists & inhibitors*
  • Low Density Lipoprotein Receptor-Related Protein-5 / chemistry
  • Molecular Docking Simulation*
  • Molecular Structure
  • Quinoxalines / chemical synthesis
  • Quinoxalines / chemistry
  • Quinoxalines / pharmacology*
  • Structure-Activity Relationship
  • Wnt Signaling Pathway / drug effects

Substances

  • Adaptor Proteins, Signal Transducing
  • Bone Morphogenetic Proteins
  • Genetic Markers
  • LRP5 protein, human
  • Low Density Lipoprotein Receptor-Related Protein-5
  • Quinoxalines
  • SOST protein, human