The 5-lipoxygenase inhibitor, zileuton, suppresses prostaglandin biosynthesis by inhibition of arachidonic acid release in macrophages

Br J Pharmacol. 2010 Oct;161(3):555-70. doi: 10.1111/j.1476-5381.2010.00930.x.

Abstract

Background and purpose: Zileuton is the only 5-lipoxygenase (5-LOX) inhibitor marketed as a treatment for asthma, and is often utilized as a selective tool to evaluate the role of 5-LOX and leukotrienes. The aim of this study was to investigate the effect of zileuton on prostaglandin (PG) production in vitro and in vivo.

Experimental approach: Peritoneal macrophages activated with lipopolysaccharide (LPS)/interferon γ (LPS/IFNγ), J774 macrophages and human whole blood stimulated with LPS were used as in vitro models and rat carrageenan-induced pleurisy as an in vivo model.

Key results: Zileuton suppressed PG biosynthesis by interference with arachidonic acid (AA) release in macrophages. We found that zileuton significantly reduced PGE2 and 6-keto prostaglandin F1α (PGF1α) levels in activated mouse peritoneal macrophages and in J774 macrophages. This effect was not related to 5-LOX inhibition, because it was also observed in macrophages from 5-LOX knockout mice. Notably, zileuton inhibited PGE2 production in LPS-stimulated human whole blood and suppressed PGE2 and 6-keto PGF1α pleural levels in rat carrageenan-induced pleurisy. Interestingly, zileuton failed to inhibit the activity of microsomal PGE2 synthase1 and of cyclooxygenase (COX)-2 and did not affect COX-2 expression. However, zileuton significantly decreased AA release in macrophages accompanied by inhibition of phospholipase A2 translocation to cellular membranes.

Conclusions and implication: Zileuton inhibited PG production by interfering at the level of AA release. Its mechanism of action, as well as its use as a pharmacological tool, in experimental models of inflammation should be reassessed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Arachidonate 5-Lipoxygenase / genetics
  • Arachidonic Acid / metabolism*
  • Carrageenan
  • Cyclooxygenase 2 / metabolism
  • Dinoprostone / biosynthesis*
  • Dinoprostone / blood
  • Disease Models, Animal
  • Humans
  • Hydroxyurea / analogs & derivatives*
  • Hydroxyurea / pharmacology
  • Interferon-gamma / pharmacology
  • Intramolecular Oxidoreductases / metabolism
  • Lipopolysaccharides / pharmacology
  • Lipoxygenase Inhibitors / pharmacology*
  • Macrophages / drug effects*
  • Macrophages / metabolism
  • Mice
  • Mice, Inbred Strains
  • Pleurisy / chemically induced
  • Pleurisy / metabolism
  • Prostaglandin-E Synthases
  • Prostaglandins F / metabolism*
  • Rats
  • Rats, Wistar
  • Zymosan

Substances

  • Lipopolysaccharides
  • Lipoxygenase Inhibitors
  • Prostaglandins F
  • Arachidonic Acid
  • Interferon-gamma
  • Carrageenan
  • Zymosan
  • Arachidonate 5-Lipoxygenase
  • Cyclooxygenase 2
  • Intramolecular Oxidoreductases
  • Prostaglandin-E Synthases
  • Dinoprostone
  • zileuton
  • prostaglandin F1
  • Hydroxyurea