Partially modified retro-inverso-enkephalinamides: topochemical long-acting analogs in vitro and in vivo

Science. 1979 Jun 15;204(4398):1210-2. doi: 10.1126/science.451565.

Abstract

The synthesis of four enkephalinamide analogs is described in which the peptide bond between residues 4 and 5 is reversed with or without simultaneous reversal of the carboxyl-terminal amide bond. These so-called partially modified retro-inverso-isomers are new, potent, topochemical analogs of the enkephalins. Tests, both in vitro and in vivo, have shown that these analogs are considerably longer acting than any previously studied enkephalins. Thus, partial reversal of the peptide bonds of the backbone can result in peptides with enhanced activity compared to a parent compound, provide that the structural complementarity of both the side chains and end groups are conserved.

MeSH terms

  • Animals
  • Behavior, Animal / drug effects
  • Brain / drug effects
  • Endorphins / pharmacology*
  • Enkephalins / chemical synthesis
  • Enkephalins / metabolism
  • Enkephalins / pharmacology*
  • Rats
  • Structure-Activity Relationship

Substances

  • Endorphins
  • Enkephalins