Structural Basis for PPARs Activation by The Dual PPARα/γ Agonist Sanguinarine: A Unique Mode of Ligand Recognition

Molecules. 2021 Oct 3;26(19):6012. doi: 10.3390/molecules26196012.

Abstract

Peroxisome proliferator-activated receptors (PPARs) play crucial roles in glucose and lipid metabolism and inflammation. Sanguinarine is a natural product that is isolated from Sanguinaria Canadensis, a potential therapeutic agent for intervention in chronic diseases. In this study, biochemical and cell-based promoter-reporter gene assays revealed that sanguinarine activated both PPARα and PPARγ, and enhanced their transcriptional activity; thus, sanguinarine was identified as a dual agonist of PPARα/γ. Similar to fenofibrate, sanguinarine upregulates the expression of PPARα-target genes in hepatocytes. Sanguinarine also modulates the expression of key PPARγ-target genes and promotes adipocyte differentiation, but with a lower adipogenic activity compared with rosiglitazone. We report the crystal structure of sanguinarine bound to PPARα, which reveals a unique ligand-binding mode of sanguinarine, dissimilar to the classic Y-shaped binding pocket, which may represent a new pharmacophore that can be optimized for selectively targeting PPARα. Further structural and functional studies uncover the molecular basis for the selectivity of sanguinarine toward PPARα/γ among all three PPARs. In summary, our study identifies a PPARα/γ dual agonist with a unique ligand-binding mode, and provides a promising and viable novel template for the design of dual-targeting PPARs ligands.

Keywords: crystal structure; dual agonist; nuclear receptors; peroxisome proliferator-activated receptors; pharmacophore.

MeSH terms

  • Adipogenesis / drug effects
  • Adipogenesis / genetics
  • Animals
  • Benzophenanthridines / chemistry*
  • Benzophenanthridines / pharmacology
  • Crystallography, X-Ray
  • Gene Expression Regulation
  • Genes, Reporter
  • HEK293 Cells
  • Hepatocytes / drug effects
  • Hepatocytes / metabolism
  • Humans
  • Isoquinolines / chemistry*
  • Isoquinolines / pharmacology
  • Ligands
  • Male
  • Mice
  • Mice, Inbred C57BL
  • Models, Molecular
  • PPAR alpha / agonists*
  • PPAR alpha / genetics
  • PPAR alpha / metabolism
  • PPAR gamma / agonists*
  • PPAR gamma / genetics
  • PPAR gamma / metabolism
  • Structure-Activity Relationship

Substances

  • Benzophenanthridines
  • Isoquinolines
  • Ligands
  • PPAR alpha
  • PPAR gamma
  • sanguinarine