C20-trifluoro-5-oxo-ETE: a metabolically stable 5-oxo-ETE derivative

Bioorg Med Chem Lett. 2011 Apr 1;21(7):1987-90. doi: 10.1016/j.bmcl.2011.02.021. Epub 2011 Feb 12.

Abstract

The total synthesis of C(20)-trifluoro-6(E),8(Z),11(Z),14(Z) 5-oxo-ETE is reported. This compound was designed as an ω-oxidation-resistant analog of 5-oxo-ETE that would be resistant to metabolism. The trifluoro derivative of 5-oxo-ETE stimulated calcium mobilization in neutrophils and desensitized these cells to subsequent exposure to 5-oxo-ETE.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Arachidonic Acids / chemistry
  • Arachidonic Acids / metabolism*
  • Arachidonic Acids / pharmacology
  • Oxidation-Reduction
  • Spectrometry, Fluorescence

Substances

  • Arachidonic Acids