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

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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.

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

Fingerprint

Butyric acid
Butyric Acid
butyric acid
Photolysis
Biological systems
Acetonitrile
Carboxylic acids
Esters
drugs
Methanol
Photons
Fluorescence
Irradiation
HEPES
Acridines
Benzopyrans
Molecules
Kinetics
Carboxylic Acids
carboxylic acids

Keywords

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

Cite this

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

In: Journal of Photochemistry and Photobiology A: Chemistry, Vol. 299, 15.02.2015, p. 44-53.

Research output: Contribution to journalArticle

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