Acridinyl methyl esters as photoactive precursors in the release of neurotransmitter amino acids

Abstract

An investigation of the use of an azaheterocycle, acridine, as an alternative photochemically removable protecting group for the carboxylic function of neurotransmitter amino acids was carried out. 9-Bromomethylacridine was used in the reaction with glycine, alanine, glutamic acid, β-alanine and γ-aminobutyric acid, to obtain model ester derivatives, which were irradiated at different wavelengths in a photochemical reactor. The process was followed by HPLC/UV, resulting in the release of the active molecule in short irradiation times. The results obtained using 419 nm irradiation show promise (35-98 min) for practical purposes. The compounds were further characterised via time-resolved fluorescence to elucidate their photophysical properties and determine the decay kinetics.