Synthesis and photoreactivity of caged blockers for glutamate transporters

Bioorg Med Chem Lett. 2003 Mar 10;13(5):965-70. doi: 10.1016/s0960-894x(02)01042-9.

Abstract

L-TBOA (L-threo-beta-benzyloxyaspartate) is, so far, the most potent non-transportable blocker for glutamate transporters. We synthesized alpha-CMCM-L-TBOA (1a) possessing [7-(carboxymethoxy)coumarin-4-yl]methyl ester as a caging group. alpha-CMCM-L-TBOA (1a) is biologically inactive until UV irradiation and the photolysis of 1a immediately released L-TBOA to show glutamate uptake inhibition. The photoreactivity of the coumarin-type caging group was superior to that of the o-nitrobenzyl-type caging group.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Transport System X-AG / antagonists & inhibitors*
  • Animals
  • Aspartic Acid / chemistry*
  • Aspartic Acid / pharmacology*
  • Biological Transport / drug effects
  • Cell Line
  • Coumarins / chemistry
  • Coumarins / pharmacology
  • Dogs
  • Drug Stability
  • Glutamic Acid / metabolism
  • Photolysis
  • Spectrophotometry, Ultraviolet

Substances

  • Amino Acid Transport System X-AG
  • Coumarins
  • benzyloxyaspartate
  • Aspartic Acid
  • Glutamic Acid