Nonpeptide small molecule agonist and antagonist original leads for neuropeptide FF1 and FF2 receptors

J Med Chem. 2014 Nov 13;57(21):8903-27. doi: 10.1021/jm500989n. Epub 2014 Oct 21.

Abstract

Neuropeptide FF1 and FF2 receptors (NPFF1-R and NPFF2-R), and their endogenous ligand NPFF, are one of only several systems responsible for mediating opioid-induced hyperalgesia, tolerance, and dependence. Currently, no small molecules displaying good affinity or selectivity for either subtype have been reported, to decipher the role of NPFF2-R as it relates to opioid-mediated analgesia, for further exploration of NPFF1-R, or for medication development for either subtype. We report the first nonpeptide small molecule scaffold for NPFF1,2-R, the guanidino-piperidines, and SAR studies resulting in the discovery of a NPFF1 agonist (7b, K(i) = 487 ± 117 nM), a NPFF1 antagonist (46, K(i) = 81 ± 17 nM), and a NPFF2 partial antagonist (53a, K(i) = 30 ± 5 nM), which serve as leads for the development of pharmacological probes and potential therapeutic agents. Testing of 46 alone was without effect in the mouse 48 °C warm-water tail-withdrawal test, but pretreatment with 46 prevented NPFF-induced hyperalgesia.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • CHO Cells
  • Cricetulus
  • Guanidines / chemical synthesis*
  • Guanidines / metabolism
  • HEK293 Cells
  • Humans
  • Ligands
  • Male
  • Mice
  • Mice, Inbred C57BL
  • Naphthalenes / chemical synthesis*
  • Naphthalenes / metabolism
  • Piperidines / chemical synthesis*
  • Piperidines / metabolism
  • Rats
  • Receptors, Neuropeptide / agonists*
  • Receptors, Neuropeptide / antagonists & inhibitors*
  • Receptors, Opioid / metabolism
  • Structure-Activity Relationship

Substances

  • 1-benzyl-N-(2-guanidinoethyl)-4-(phenylamino)piperidine-4-carboxamide
  • 2-amino-N-((1-benzyl-4-(phenylamino)piperidin-4-yl)methyl)-5-guanidinopentanamide
  • Guanidines
  • Ligands
  • N-((1-benzyl-4-(naphthalen-1-ylmethyl)piperidin-4-yl)methyl)-2-guanidinoacetamide
  • Naphthalenes
  • Piperidines
  • Receptors, Neuropeptide
  • Receptors, Opioid
  • neuropeptide FF receptor