Synthesis and biological activities of aryl-ether-, biaryl-, and fluorene-aspartic acid and diaminopropionic acid analogs as potent inhibitors of the high-affinity glutamate transporter EAAT-2

Bioorg Med Chem Lett. 2005 Nov 15;15(22):4985-8. doi: 10.1016/j.bmcl.2005.08.003.

Abstract

Excitatory amino acid transporters (EAATs) play a pivotal role in maintaining glutamate homeostasis in the mammalian central nervous system, with the EAAT-2 subtype thought to be responsible for the bulk of the glutamate uptake in forebrain regions. A complete elucidation of the functional role of EAAT-2 has been hampered by the lack of potent and selective pharmacological tools. In this study, we describe the synthesis and biological activities of novel aryl-ether, biaryl-, and fluorene-aspartic acid and diaminopropionic acid analogs as potent inhibitors of EAAT-2. Compound (16) represents one of the most potent (IC50=85+/-5 nM) and selective inhibitors of EAAT-2 identified to date.

MeSH terms

  • Aspartic Acid / chemistry*
  • Biological Transport / drug effects
  • Ether / chemistry*
  • Excitatory Amino Acid Transporter 2 / antagonists & inhibitors*
  • Excitatory Amino Acid Transporter 2 / metabolism
  • Fluorenes / chemistry*
  • Inhibitory Concentration 50
  • Molecular Structure
  • Propionates / chemical synthesis
  • Propionates / chemistry*
  • Structure-Activity Relationship
  • beta-Alanine / analogs & derivatives*
  • beta-Alanine / chemical synthesis
  • beta-Alanine / chemistry*

Substances

  • Excitatory Amino Acid Transporter 2
  • Fluorenes
  • Propionates
  • Ether
  • beta-Alanine
  • Aspartic Acid
  • fluorene
  • propionic acid