title: Photophysics of novel coumarin-labeled depsipeptides in solution: sensing interactions with SDS micelle via TICT model.
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.
authors.affiliation: Department of Chemistry, Center for Heterocyclic Compounds, University of Florida, Gainesville, FL 32611-7200, USA.
authors.forename: Suvendu
authors.initials: S
authors.lastname: Biswas
authors.forename: Ilker
authors.initials: I
authors.lastname: Avan
authors.forename: Akash K
authors.initials: AK
authors.lastname: Basak
authors.forename: Nader E
authors.initials: NE
authors.lastname: Abo-Dya
authors.forename: Abdullah
authors.initials: A
authors.lastname: Asiri
authors.forename: Alan R
authors.initials: AR
authors.lastname: Katritzky
mesh_terms: D003374:Coumarins / Q000737:chemistry*; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000138:chemical synthesis*; D008823:Micelles; D012967:Sodium Dodecyl Sulfate / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D013194:Staining and Labeling
chemical_list: D003374:Coumarins; D047630:Depsipeptides; D005456:Fluorescent Dyes; D008823:Micelles; D012967:Sodium Dodecyl Sulfate; C030123:coumarin