Synthesis and biological evaluation of 1-amino-2-phosphonomethylcyclopropanecarboxylic acids, new group III metabotropic glutamate receptor agonists

J Med Chem. 2007 Jul 26;50(15):3585-95. doi: 10.1021/jm070262c. Epub 2007 Jun 28.

Abstract

Stereoisomers of 1-amino-2-phosphonomethylcyclopropanecarboxylic acid (APCPr), conformationally restricted analogues of L-AP4 (2-amino-4-phosphonobutyric acid), have been prepared and evaluated at recombinant group III metabotropic glutamate receptors. They activate these receptors over a broad range of potencies. The most potent isomer (1S,2R)-APCPr displays a similar pharmacological profile as that of L-AP4 (EC50 0.72, 1.95, >500, 0.34 microM at mGlu4, 6, 7, 8 receptors, respectively, and no effect at group I/II mGluRs). It was characterized on native receptors located in the basal ganglia (BG) where it induced a robust and reversible inhibition of synaptic transmission. It was tested in vivo in haloperidol-induced catalepsy, a model of Parkinsonian akinesia, by direct infusion in the globus pallidus of the BG. At a dose of 0.5 nmol/microL, catalepsy was significantly antagonized. This study reveals that (1S,2R)-APCPr is a potent group III mGluR agonist and confirms that these receptors may be considered as a therapeutic target in the Parkinson's disease.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Amino Acids / pharmacology
  • Animals
  • Antiparkinson Agents / chemical synthesis*
  • Antiparkinson Agents / chemistry
  • Antiparkinson Agents / pharmacology
  • Basal Ganglia / drug effects
  • Basal Ganglia / physiology
  • Catalepsy / chemically induced
  • Catalepsy / drug therapy
  • Cell Line
  • Haloperidol
  • Humans
  • In Vitro Techniques
  • Injections
  • Male
  • Models, Molecular
  • Molecular Conformation
  • Organophosphonates / chemical synthesis*
  • Organophosphonates / chemistry
  • Organophosphonates / pharmacology
  • Patch-Clamp Techniques
  • Rats
  • Rats, Sprague-Dawley
  • Rats, Wistar
  • Receptors, Metabotropic Glutamate / agonists*
  • Receptors, N-Methyl-D-Aspartate / drug effects
  • Stereoisomerism
  • Structure-Activity Relationship
  • Synaptic Transmission / drug effects

Substances

  • 1-amino-2-phosphonomethylcyclopropanecarboxylic acid
  • Amino Acids
  • Antiparkinson Agents
  • Organophosphonates
  • Receptors, Metabotropic Glutamate
  • Receptors, N-Methyl-D-Aspartate
  • Haloperidol