Photophysics of novel coumarin-labeled depsipeptides in solution: sensing interactions with SDS micelle via TICT model

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...

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Bibliographic Details
Published in:Amino acids 2013-07, Vol.45 (1), p.159-170
Main Authors: Biswas, Suvendu, Avan, Ilker, Basak, Akash K, Abo-Dya, Nader E, Asiri, Abdullah, Katritzky, Alan R
Format: Article
Language:English
Subjects:
Amino acids
Analytical Chemistry
Biochemical Engineering
Biochemistry
Biological
Biomedical and Life Sciences
Coumarins - chemistry
depsipeptides
Depsipeptides - chemical synthesis
Depsipeptides - chemistry
Detection
fluorescence
Fluorescent Dyes - chemical synthesis
Life Sciences
Mathematical models
Membranes
Micelles
Neurobiology
Original Article
Proteomics
Sodium Dodecyl Sulfate - chemistry
Solvents
Spectrometry, Fluorescence
Staining and Labeling
Synthesis
yields
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Summary: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.
ISSN:0939-4451
1438-2199
DOI:10.1007/s00726-013-1483-3