17-OxoDHA Is a PPARα/γ Dual Covalent Modifier and Agonist

ACS Chem Biol. 2016 Sep 16;11(9):2447-55. doi: 10.1021/acschembio.6b00338. Epub 2016 Jul 1.

Abstract

17-Hydroxy docosahexaenoic acid (17-HDHA) is an oxidized form of docosahexaenoic acid (DHA) and known as a specialized proresolving mediator. We found that a further oxidized product, 17-oxodocosahexaenoic acid (17-oxoDHA), activates peroxisome proliferator-activated receptors γ (PPARγ) and PPARα in transcriptional assays and thus can be classified as an α/γ dual agonist. ESI mass spectroscopy and X-ray crystallographic analysis showed that 17-oxoDHA binds to PPARγ and PPARα covalently, making 17-oxoDHA the first of a novel class of PPAR agonists, the PPARα/γ dual covalent agonist. Furthermore, the covalent binding sites were identified as Cys285 for PPARγ and Cys275 for PPARα.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Docosahexaenoic Acids / pharmacology*
  • PPAR alpha / agonists
  • PPAR alpha / drug effects*
  • PPAR gamma / agonists
  • PPAR gamma / drug effects*
  • Point Mutation
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • PPAR alpha
  • PPAR gamma
  • Docosahexaenoic Acids
  • 17-hydroxy-4,7,10,13,15,19-docosahexaenoic acid