Farnesyl-L-cysteine analogs can inhibit or initiate superoxide release by human neutrophils

J Biol Chem. 1994 Jun 17;269(24):16837-44.

Abstract

A series of farnesylcysteine analogs was studied with respect to their abilities to interfere with fMet-Leu-Phe (fMLP)-stimulated superoxide (O2-.) release by human neutrophils. Simple acyl derivatives of farnesyl-L-cysteine, such as the N-acetyl (L-AFC) and N-isobutyryl derivatives (L-iBFC), which are substrates for the isoprenylated protein methyltransferase, can block O2-. release. The N-butyryl analog (L-BFC), which is an isomer of L-iBFC and also a substrate for the methyltransferase, does not inhibit O2-. release but actually stimulates it in the absence of fMLP. Other analogs, including the N-pivaloyl derivative, which has been found to be neither a substrate nor an inhibitor of methyltransferase, also stimulate very large quantities of O2-. production. The stimulatory effects of these derivatives are saturable and exquisitively sensitive to small structural changes in the analogs. The signal transduction pathway(s) utilized by pivaloyl derivatives for triggering O2-. generation is very similar to that employed by fMLP. These data make it clear that farnesyl-L-cysteine analogs do not produce their pharmacological effects in neutrophils via methyltransferase blockade. This could be further demonstrated by showing that sinefungin and S-adenosylhomocysteine, both powerful and general methyltransferase inhibitors which bind at the S-adenosylmethionine site, had no effect in preventing the increased oxygen consumption associated with O2-. production in permeabilized neutrophils. These studies reveal that farnesyl-L-cysteine analogs interact with a hitherto undefined target in neutrophils that may be exploited for inhibiting or stimulating the inflammatory or antimicrobial responses of these cells.

Publication types

  • Comparative Study
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Chromatography, High Pressure Liquid
  • Cysteine / analogs & derivatives*
  • Cysteine / chemical synthesis
  • Cysteine / pharmacology*
  • Humans
  • In Vitro Techniques
  • Indicators and Reagents
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • N-Formylmethionine Leucyl-Phenylalanine / pharmacology
  • Neutrophils / drug effects
  • Neutrophils / metabolism*
  • Phosphoproteins / blood
  • Structure-Activity Relationship
  • Superoxide Dismutase / pharmacology
  • Superoxides / blood*
  • Tetradecanoylphorbol Acetate / pharmacology

Substances

  • Indicators and Reagents
  • Phosphoproteins
  • Superoxides
  • N-Formylmethionine Leucyl-Phenylalanine
  • S-farnesylcysteine
  • Superoxide Dismutase
  • Cysteine
  • Tetradecanoylphorbol Acetate