Lights and shadows of electrophile signaling: focus on the Nrf2-Keap1 pathway

Future Med Chem. 2019 Apr;11(7):707-721. doi: 10.4155/fmc-2018-0423. Epub 2019 Apr 3.

Abstract

Targeted covalent modification is assuming consolidated importance in drug discovery. In this context, the electrophilic tuning of redox-dependent cell signaling is attracting major interest, as it opens prospect for treating numerous pathologic conditions. Herein, we discuss the rationale and the issues of electrophile-based approaches, focusing on the transcriptional Nrf2-Keap1 pathway as a test case. We also highlight relevant medicinal chemistry strategies researchers have devised to meet the ambitious goal, dwelling on the investigational and therapeutic potential of modulating redox-signaling networks through regulatory cysteine switches.

Keywords: Nrf2–Keap1 pathway; cysteine trapping; electrophilic compounds; redox signaling; covalent adduct.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Animals
  • Antioxidants / chemistry*
  • Antioxidants / pharmacology
  • Cysteine / metabolism
  • Dimethyl Fumarate / chemistry
  • Dimethyl Fumarate / pharmacology
  • Drug Design
  • Humans
  • Kelch-Like ECH-Associated Protein 1 / metabolism*
  • Molecular Structure
  • NF-E2-Related Factor 2 / metabolism*
  • Oleanolic Acid / analogs & derivatives
  • Oleanolic Acid / chemistry
  • Oleanolic Acid / pharmacology
  • Oxidation-Reduction
  • Oxidative Stress
  • Signal Transduction
  • Structure-Activity Relationship

Substances

  • Antioxidants
  • Kelch-Like ECH-Associated Protein 1
  • NF-E2-Related Factor 2
  • Oleanolic Acid
  • bardoxolone methyl
  • Dimethyl Fumarate
  • Cysteine