Acridinyl methyl esters as photoactive precursors in the release of neurotransm...

• Author(s): Piloto, Ana M. ; Hungerford, Graham ; Costa, Susana P. G. ; Gonçalves, M. Sameiro T.
• Date: 2013
• Persistent ID: http://hdl.handle.net/1822/21961
• Origin: RepositóriUM - Universidade do Minho
• Subject(s): Acridinyl methyl esters; Photocleavable protecting groups; Neurotransmitters; Amino acids; Caged compounds
• Document Type: Article
• Language: English

Description

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.