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Aminobenzocoumarinylmethyl esters as photoactive precursors for the release of butyric acid

Aminobenzocoumarinylmethyl esters as photoactive precursors for the release of butyric acid The evaluation of the photorelease of a carboxylic acid drug, using butyric acid as a representative model, was carried out by using 7-amino-4-chloromethyl-2-oxo-2 H -naphtho(1,2- b )pyran, an aminobenzocoumarin, and its mono- and di-methylated or ethylated derivatives. This study was intended to improve the release of butyric acid from benzocoumarins by the addition of an amino group to the heterocycle by applying the knowledge of second-generation coumarinylmethyl-based photoremovable protecting groups. Photolysis studies were performed on the resultant ester cages by irradiation in a photochemical reactor at 254, 300, 350 and 419 nm, using methanol/HEPES buffer 80 : 20 solutions as solvent. The data obtained showed that these new fluorescent aminobenzocoumarins are superior to all the previously tested benzocoumarins with the same or different ring fusions. The photophysics of the compounds was characterised by both steady state and time-resolved methods. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png New Journal of Chemistry Royal Society of Chemistry

Aminobenzocoumarinylmethyl esters as photoactive precursors for the release of butyric acid

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Publisher
Royal Society of Chemistry
Copyright
This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique
ISSN
1144-0546
eISSN
1369-9261
DOI
10.1039/c5nj00699f
Publisher site
See Article on Publisher Site

Abstract

The evaluation of the photorelease of a carboxylic acid drug, using butyric acid as a representative model, was carried out by using 7-amino-4-chloromethyl-2-oxo-2 H -naphtho(1,2- b )pyran, an aminobenzocoumarin, and its mono- and di-methylated or ethylated derivatives. This study was intended to improve the release of butyric acid from benzocoumarins by the addition of an amino group to the heterocycle by applying the knowledge of second-generation coumarinylmethyl-based photoremovable protecting groups. Photolysis studies were performed on the resultant ester cages by irradiation in a photochemical reactor at 254, 300, 350 and 419 nm, using methanol/HEPES buffer 80 : 20 solutions as solvent. The data obtained showed that these new fluorescent aminobenzocoumarins are superior to all the previously tested benzocoumarins with the same or different ring fusions. The photophysics of the compounds was characterised by both steady state and time-resolved methods.

Journal

New Journal of Chemistry – Royal Society of Chemistry

Published: Jul 1, 2015

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