Design, Synthesis, and Evaluation of Triazole Derivatives That Induce Nrf2 Dependent Gene Products and Inhibit the Keap1-Nrf2 Protein-Protein Interaction

J Med Chem. 2015 Sep 24;58(18):7186-94. doi: 10.1021/acs.jmedchem.5b00602.

Abstract

The transcription factor Nrf2 regulates the expression of a large network of cytoprotective and metabolic enzymes and proteins. Compounds that directly and reversibly inhibit the interaction between Nrf2 and its main negative regulator Keap1 are potential pharmacological agents for a range of disease types including neurodegenerative conditions and cancer. We describe the development of a series of 1,4-diphenyl-1,2,3-triazole compounds that inhibit the Nrf2-Keap1 protein-protein interaction (PPI) in vitro and in live cells and up-regulate the expression of Nrf2-dependent gene products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Click Chemistry
  • Computer Simulation
  • Databases, Chemical
  • Dose-Response Relationship, Drug
  • Fluorescence Polarization
  • HEK293 Cells
  • Heme Oxygenase-1 / biosynthesis*
  • Heme Oxygenase-1 / genetics
  • Humans
  • Intracellular Signaling Peptides and Proteins / chemistry
  • Intracellular Signaling Peptides and Proteins / metabolism*
  • Isothiocyanates / chemistry
  • Isothiocyanates / pharmacology
  • Kelch-Like ECH-Associated Protein 1
  • Molecular Docking Simulation
  • NAD(P)H Dehydrogenase (Quinone) / biosynthesis*
  • NAD(P)H Dehydrogenase (Quinone) / genetics
  • NF-E2-Related Factor 2 / chemistry
  • NF-E2-Related Factor 2 / metabolism*
  • Protein Binding
  • Structure-Activity Relationship
  • Sulfoxides
  • Triazoles / chemical synthesis
  • Triazoles / chemistry*
  • Triazoles / pharmacology

Substances

  • Intracellular Signaling Peptides and Proteins
  • Isothiocyanates
  • KEAP1 protein, human
  • Kelch-Like ECH-Associated Protein 1
  • NF-E2-Related Factor 2
  • NFE2L2 protein, human
  • Sulfoxides
  • Triazoles
  • HMOX1 protein, human
  • Heme Oxygenase-1
  • NAD(P)H Dehydrogenase (Quinone)
  • NQO1 protein, human
  • sulforaphane