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Photophysics of novel coumarin-labeled depsipeptides in solution: sensing interactions with SDS micelle via TICT model
Faculty
Pharmacy
Year:
2013
Type of Publication:
Article
Pages:
159-170
Authors:
Abo-Dya, Nader E, Katritzky, Alan R, Biswas, Suvendu, Avan, Ilker, Basak, Akash K, Asiri, Abdullah
DOI:
10.1007/s00726-013-1483-3
Journal:
AMINO ACIDS SPRINGER WIEN
Volume:
45
Research Area:
Biochemistry \& Molecular Biology
ISSN
ISI:000320372500012
Keywords :
Coumarin, Peptidomimetics, Depsipeptides, SDS, Micelle, TICT
Abstract:
N-Acylbenzotriazoles enable the synthesis (69-92 \% yield) of blue to green fluorescent coumarin-labeled depsidipeptides 8a-f (quantum yields 0.004-0.97) and depsitripeptides 12a-d (quantum yields 0.02-0.96). Detailed photophysical studies of fluorescent coumarin-labeled depsipeptides 8a-f and 12a-d are reported for both polar protic and polar aprotic solvents. 7-Methoxy and 7-diethylaminocoumarin-3-ylcarbonyl depsipeptides 8c,f and 12d are highly solvent sensitive. These highly fluorescent compounds could be useful for peptide assays. Further photophysical studies of 7-diethylaminocoumarin-labeled depsipeptides 8c,12d within the micellar microenvironment of SDS reflect their ability to bind with the biological membrane, suggesting potential applications in the fields of bio- and medicinal chemistry.
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