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

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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 (https://doi.org/10.1016/j.jphotochem.2014.10.016)

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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.

ORCID iDs

Piloto, Ana M., Hungerford, Graham, Sutter, Jens U. ORCID logoORCID: https://orcid.org/0000-0002-3782-6338, Soares, Ana M.S., Costa, Susana P.G. and Gonçalves, M. Sameiro T.;
CORE (COnnecting REpositories)