Effect of anchoring 4-anilidopiperidines to opioid peptides

Bioorg Med Chem Lett. 2013 Jun 1;23(11):3434-7. doi: 10.1016/j.bmcl.2013.03.065. Epub 2013 Apr 3.

Abstract

We report here the design, synthesis, and in vitro characterization of new opioid peptides featuring a 4-anilidopiperidine moiety. Despite the fact that the chemical structures of fentanyl surrogates have been found suboptimal per se for the opioid activity, the corresponding conjugates with opioid peptides displayed potent opioid activity. These studies shed an instructive light on the strategies and potential therapeutic values of anchoring the 4-anilidopiperidine scaffold to different classes of opioid peptides.

Publication types

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

MeSH terms

  • Animals
  • Cell Line
  • Fentanyl / chemistry
  • Humans
  • Kinetics
  • Mice
  • Opioid Peptides / chemical synthesis
  • Opioid Peptides / chemistry*
  • Opioid Peptides / metabolism
  • Piperidines / chemical synthesis
  • Piperidines / chemistry*
  • Piperidines / metabolism
  • Protein Binding
  • Receptors, Opioid, delta / chemistry
  • Receptors, Opioid, delta / genetics
  • Receptors, Opioid, delta / metabolism
  • Receptors, Opioid, mu / chemistry
  • Receptors, Opioid, mu / genetics
  • Receptors, Opioid, mu / metabolism
  • Structure-Activity Relationship

Substances

  • Opioid Peptides
  • Piperidines
  • Receptors, Opioid, delta
  • Receptors, Opioid, mu
  • Fentanyl