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

• Main Author: Piloto, Ana M.
• Publication Date: 2013
• Other Authors: Hungerford, Graham, Costa, Susana P. G., Gonçalves, M. Sameiro T.
• Format: Article
• Language: eng
• Source: Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
• Download full: http://hdl.handle.net/1822/21961
• topic: Acridinyl methyl esters; Photocleavable protecting groups; Neurotransmitters; Amino acids; Caged compounds; Science & Technology

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.