Coumarin (2H-benzopyran-2-one) derivatives with amino, phenyl, 4-methoxyphenyl and styryl groups at the 7-position, were synthesized and used in the derivatization of glycine and β-alanine. The new ester cages of glycine and β-alanine, selected as models of carboxylic acid bioactive molecules, revealed to be interesting photo-responsive units. A remarkable behaviour towards irradiation at higher wavelength (350 and 419 nm) occurred in conjugates obtained from 4-(chloromethyl)-7-styryl-2H-benzopyran-2one. Time-resolved fluorescence studies complemented the photolysis results and proposed mechanism revealing the presence of different fluorescing species by the determination of decay associated spectra. This study shows new promising alternative moieties for the development of photoactivable fluorescent acid prodrugs.
Abstract:The synthesis of a new 7-bromo-4-(chloromethyl)-coumarin to be used as cage for the release of bioactive molecules is presented. Ester cages of two neurotransmitter amino acids, glycine and β-alanine, were also synthetized. These neurotransmitters were chosen as models due to their biological relevance. The glycine and β-alanine ester conjugates, in methanol/HEPES buffer (80:20), were irradiated at 254, 300, 350 and 419 nm in a Rayonet RPR-100 photochemical reactor and the photolysis process was followed by HPLC with UV detection. These results were compared with those previously obtained by our research group when 4-chloromethyl-coumarin was used in the photorelease of glycine and β-alanine.
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