Simplified heterocyclic analogues of fluoxetine inhibit inducible nitric oxide production in lipopolysaccharide-induced BV2 cells

Biol Pharm Bull. 2011;34(4):538-44. doi: 10.1248/bpb.34.538.

Abstract

A series of fluoxetine, where the N-methylamino group was replaced and then simplified, were synthesized and their inhibitory effect was tested for nitric oxide (NO) production and inducible NO synthase (iNOS) expression in lipopolysaccharide (LPS)-induced BV2 cells. Although the synthesized compounds generally revealed weaker activity or greater cytotoxicity than fluoxetine, compound 10a, in which the N-methylamino group in fluoxetine was replaced by morpholine, and the trifluoromethylphenyl ring was substituted with simple oxo group, suppressed NO production dose-dependently at 10, 20 and 40 µM concentrations with less cytotoxicity than fluoxetine, and inhibited iNOS mRNA and protein expression at the same concentrations in LPS-induced BV2 cells. The results suggested that the trifluoromethylphenyl ring moiety in fluoxetine is not necessary for the suppression of NO production and that 10a has the potential as a potent inhibitor of NO production.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemical synthesis
  • Anti-Inflammatory Agents / pharmacology*
  • Cell Line
  • Dose-Response Relationship, Drug
  • Fluoxetine / analogs & derivatives
  • Fluoxetine / pharmacology*
  • Heterocyclic Compounds / chemical synthesis
  • Heterocyclic Compounds / pharmacology*
  • Lipopolysaccharides
  • Mice
  • Nitric Oxide / biosynthesis*
  • Nitric Oxide Synthase Type II / genetics
  • Nitric Oxide Synthase Type II / metabolism*
  • RNA, Messenger / metabolism

Substances

  • Anti-Inflammatory Agents
  • Heterocyclic Compounds
  • Lipopolysaccharides
  • RNA, Messenger
  • Fluoxetine
  • Nitric Oxide
  • Nitric Oxide Synthase Type II