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Small molecules inhibit the interaction of Nrf2 and the Keap1 Kelch domain through a non-covalent mechanism

Authors :
Matvey E. Lukashev
Victor Hong
Hernan Cuervo
Ping Jin
Douglas Marcotte
Alexey Lugovskoy
Valérie Vivat
C Hession
Deping Wang
Joachim Kraemer
Jean-Christophe Hus
Chris Bergeron
Dominique Roecklin
Weike Zeng
Malgorzata M. Vecchi
Dirk Winkler
Istvan J. Enyedy
Cédric Atmanene
Laura Silvian
Andres McKenzie
Jianhua Chao
Source :
Bioorganic & Medicinal Chemistry. 21:4011-4019
Publication Year :
2013
Publisher :
Elsevier BV, 2013.

Abstract

Keap1 binds to the Nrf2 transcription factor to promote its degradation, resulting in the loss of gene products that protect against oxidative stress. While cell-active small molecules have been identified that modify cysteines in Keap1 and effect the Nrf2 dependent pathway, few act through a non-covalent mechanism. We have identified and characterized several small molecule compounds that specifically bind to the Keap1 Kelch-DC domain as measured by NMR, native mass spectrometry and X-ray crystallography. One compound upregulates Nrf2 response genes measured by a luciferase cell reporter assay. The non-covalent inhibition strategy presents a reasonable course of action to avoid toxic side-effects due to non-specific cysteine modification.

Details

ISSN :
09680896
Volume :
21
Database :
OpenAIRE
Journal :
Bioorganic & Medicinal Chemistry
Accession number :
edsair.doi.dedup.....a072bbcacd3d6aff3b75021f90ae50a6
Full Text :
https://doi.org/10.1016/j.bmc.2013.04.019