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

• A set of heteroaromatic compounds were evaluated as benzyl-type phototriggers, in comparison with the well-known o-nitrobenzyl group.
• Butyric acid was selected as a model carboxylic acid drug in the photorelease studies.
• Irradiation of the ester cages was carried out in a photochemical reactor at 254, 300, 350 and 419 nm, in methanol or acetonitrile in 80:20 mixtures with HEPES buffer.
• Time-resolved fluorescence was used to elucidate their photophysical properties and determine the decay kinetics.
• The suitability to be addressed using two-photon excitation was also demonstrated with promising TPE cross-sections, which is advantageous if their use in biological systems is to be considered.

Aimng 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.