Synthesis and biological activities of position one and three transposed analogs of the opioid peptide YKFA

Bioorg Med Chem Lett. 1999 Dec 20;9(24):3441-6. doi: 10.1016/s0960-894x(99)00625-3.

Abstract

Tyr-c[D-Lys-Phe-Ala], YKFA, is a potent opioid peptide analog with subnanomolar IC50s toward mu and delta receptors. Transposing Phe and Tyr, a modification found to promote mu antagonist activity in opioid/somatostatin hybrids, gave surprisingly high mu agonist activities for several related analogs, considering the lack of a 1-position hydroxyl function.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Amino Acid Sequence
  • Chromatography, High Pressure Liquid
  • Chromatography, Thin Layer
  • Mass Spectrometry
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / chemistry
  • Oligopeptides / pharmacology
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / pharmacology
  • Receptors, Opioid, mu / antagonists & inhibitors*

Substances

  • Oligopeptides
  • Peptides, Cyclic
  • Receptors, Opioid, mu
  • tyrosyl-cyclo(lysyl-phenylalanyl-alanyl)