Fentanyl derivatives bearing aliphatic alkaneguanidinium moieties: a new series of hybrid molecules with significant binding affinity for mu-opioid receptors and I2-imidazoline binding sites

Bioorg Med Chem Lett. 2004 Jan 19;14(2):491-3. doi: 10.1016/j.bmcl.2003.10.048.

Abstract

A new series of fentanyl derivatives [i.e., N-[1-(2-phenethyl)-4-piperidyl]-N-(guanidinoalkyl)propanamide] bearing aliphatic alkaneguanidinium moieties were prepared. Their affinities for the micro opioid receptors and for the I(2)-imidazoline binding sites (I(2)-IBS) were determined on human post-mortem prefrontal cortex membranes. All of these hybrid compounds had significant and/or very high affinity for both receptors in the nanomolar range, meaning an improvement compared to the prototype N-[1-(2-phenethyl)-4-piperidyl]-N-(guanidinopropyl)propanamide previously reported.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkanes / chemistry
  • Alkanes / metabolism*
  • Animals
  • Binding Sites / physiology
  • Fentanyl / chemistry
  • Fentanyl / metabolism*
  • Guanidines / metabolism*
  • Imidazoline Receptors
  • Mice
  • Piperazines / metabolism*
  • Protein Binding / physiology
  • Receptors, Drug / metabolism*
  • Receptors, Opioid, mu / metabolism*

Substances

  • 3-(4-guanidinophenyl)-N-(2-phenylethyl)-3-((4-(3,3-diphenylpropylaminocarbonyl)piperazin-1-yl)carbonyl)propanamide
  • Alkanes
  • Guanidines
  • Imidazoline Receptors
  • Piperazines
  • Receptors, Drug
  • Receptors, Opioid, mu
  • Fentanyl