Porphyrin Derivatives Inhibit the Interaction between Receptor Activator of NF-κB and Its Ligand

ChemMedChem. 2017 Oct 20;12(20):1697-1702. doi: 10.1002/cmdc.201700462. Epub 2017 Oct 4.

Abstract

Receptor activator of NF-κB (RANK), a member of the TNF-receptor superfamily, plays an important role in bone resorption and stimulates immune and epithelial cell activation. Denosumab, a human monoclonal antibody that blocks the RANK ligand (RANKL), is approved for the treatment of osteoporosis and bone metastasis. However, a small molecule that inhibits the RANK-RANKL interaction would be beneficial to decrease cost and to facilitate treatments with orally available therapeutic agents. Herein we report the discovery of the first nonpeptidic inhibitors of RANK-RANKL interactions. In screening a chemical library by competitive ELISA, the porphyrin verteporfin was identified as a hit. Derivatives were screened, and the chlorin-macrocycle-containing pheophorbide A and purpurin 18 were found to bind recombinant RANKL, to inhibit RANK-RANKL interactions in the ELISA, and to suppress the RANKL-dependent activation of model cells and the differentiation of RANK-expressing precursors into osteoclasts. This discovery of a family of small molecules that inhibit RANK activation presents an initial basis for further development of nonpeptidic therapeutic agents targeting the interaction between RANK and RANKL.

Keywords: ELISA; cell-based assays; osteoclasts; porphyrins; receptor activator of NF-κB.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Survival
  • Humans
  • Jurkat Cells
  • Mice
  • Molecular Structure
  • Osteogenesis / drug effects
  • Porphyrins / chemistry
  • Porphyrins / pharmacology*
  • Protein Binding
  • RANK Ligand / antagonists & inhibitors*
  • RANK Ligand / chemistry
  • RANK Ligand / metabolism
  • Receptor Activator of Nuclear Factor-kappa B / antagonists & inhibitors*
  • Receptor Activator of Nuclear Factor-kappa B / chemistry
  • Receptor Activator of Nuclear Factor-kappa B / metabolism
  • Structure-Activity Relationship

Substances

  • Porphyrins
  • RANK Ligand
  • Receptor Activator of Nuclear Factor-kappa B