Photoactivable heterocyclic cages in a comparative release study of butyric acid as a model drug

Piloto, Ana M. and Hungerford, Graham and Sutter, Jens U. and Soares, Ana M.S. and Costa, Susana P.G. and Gonçalves, M. Sameiro T. (2015) Photoactivable heterocyclic cages in a comparative release study of butyric acid as a model drug. Journal of Photochemistry and Photobiology A: Chemistry, 299. pp. 44-53. ISSN 1010-6030

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    Abstract

    Aiming: at the improvement of the photorelease of butyric acid - a model carboxylic acid drug, a set of heteroaromatic compounds based on acridine, naphtho[2,1-b]pyran, 3H-benzopyran fused julolidine and thioxo-naphtho[2,1-b]pyran were evaluated as benzyl-type phototriggers, in comparison with the well-known o-nitrobenzyl group. The corresponding ester cages were irradiated in a photochemical reactor at 254, 300, 350 and 419 nm, in two solvent systems (methanol or acetonitrile in 80:20 mixtures with HEPES buffer). Photolysis studies showed that, for some of the cages, the release of the active molecule occurred with short irradiation times using 419 nm. Time-resolved fluorescence was used to elucidate their photophysical properties and determine the decay kinetics. Studies were also carried out to assess the suitability of using two-photon excitation to address these compounds, which is advantageous if their use in biological systems is to be considered.