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

Ana M. Piloto, Graham Hungerford, Jens U. Sutter, Ana M.S. Soares, Susana P.G. Costa, M. Sameiro T. Gonçalves

Research output: Contribution to journalArticle

11 Citations (Scopus)
54 Downloads (Pure)

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.

Original languageEnglish
Pages (from-to)44-53
Number of pages10
JournalJournal of Photochemistry and Photobiology A: Chemistry
Volume299
Early online date24 Oct 2014
DOIs
Publication statusPublished - 15 Feb 2015

Keywords

  • acridine
  • butyric acid
  • coumarin
  • o-nitrobenzyl group
  • phototriggers
  • prodrugs

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