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 language | English |
|---|---|
| Pages (from-to) | 44-53 |
| Number of pages | 10 |
| Journal | Journal of Photochemistry and Photobiology A: Chemistry |
| Volume | 299 |
| Early online date | 24 Oct 2014 |
| DOIs | |
| Publication status | Published - 15 Feb 2015 |
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Keywords
- acridine
- butyric acid
- coumarin
- o-nitrobenzyl group
- phototriggers
- prodrugs
Cite this
}
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 journal › Article
TY - JOUR
T1 - Photoactivable heterocyclic cages in a comparative release study of butyric acid as a model drug
AU - Piloto, Ana M.
AU - Hungerford, Graham
AU - Sutter, Jens U.
AU - Soares, Ana M.S.
AU - Costa, Susana P.G.
AU - Gonçalves, M. Sameiro T.
PY - 2015/2/15
Y1 - 2015/2/15
N2 - 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.
AB - 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.
KW - acridine
KW - butyric acid
KW - coumarin
KW - o-nitrobenzyl group
KW - phototriggers
KW - prodrugs
UR - http://www.scopus.com/inward/record.url?scp=84910601493&partnerID=8YFLogxK
U2 - 10.1016/j.jphotochem.2014.10.016
DO - 10.1016/j.jphotochem.2014.10.016
M3 - Article
VL - 299
SP - 44
EP - 53
JO - Journal of Photochemistry and Photobiology A: Chemistry
JF - Journal of Photochemistry and Photobiology A: Chemistry
SN - 1010-6030
ER -