Effect of 3-phenylamino-L-alanine on tryptophan binding to rat hepatic nuclear envelopes

Toxicology. 1994 Jan 26;86(1-2):135-45. doi: 10.1016/0300-483x(94)90058-2.

Abstract

We have determined that the addition of 3-phenylamino-L-alanine (PAA), a recently reported contaminant in L-tryptophan implicated in the eosinophilia-myalgia syndrome, affects tryptophan binding by utilizing an in vitro measurement of 3H-tryptophan binding to hepatic nuclei or nuclear envelopes. PAA (10(-10) to 10(-4) M) diminishes the inhibitory effect of binding due to excess unlabeled L-tryptophan (10(-4) M). PAA alone has no inhibitory effect on binding. The effect of PAA on in vitro tryptophan binding is in contrast to that of another contaminant, 1,1'-ethylidenebis(tryptophan), which together with excess unlabeled L-tryptophan does not appreciably affect the binding. In vitro addition of PAA and L-tryptophan to nuclei of rat brain or of cultured murine macrophages does not affect [3H]tryptophan binding in comparison to L-tryptophan alone as is the case with hepatic nuclear envelopes. Adding PAA to an in vitro protein synthesis system and measuring [3H]tryptophan or [3H]alanine incorporation into acid-precipitable proteins reveals that it competes similarly, but somewhat less, than does equimolar concentrations of unlabeled L-tryptophan or L-alanine, respectively. This suggests that PAA or a breakdown compound becomes incorporated into proteins. Speculation as to how PAA may affect tissues in experimental animals is presented.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alanine / analogs & derivatives*
  • Alanine / pharmacology
  • Animals
  • Cell Nucleus / drug effects
  • Cell Nucleus / metabolism
  • Drug Contamination
  • Female
  • Kinetics
  • Liver / drug effects*
  • Liver / metabolism*
  • Liver / ultrastructure
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Mice
  • Microsomes, Liver / drug effects
  • Microsomes, Liver / metabolism
  • Nuclear Envelope / drug effects
  • Nuclear Envelope / metabolism
  • Rats
  • Rats, Sprague-Dawley
  • Tritium
  • Tryptophan / metabolism*

Substances

  • Tritium
  • 3-(phenylamino)alanine
  • Tryptophan
  • Alanine