title: Interaction of fluorescently labeled triethyleneglycol and peptide derivatives with β-cyclodextrin.
abstract: A triethyleneglycol (TEG) chain, a linear peptide, and a cyclic peptide labeled with 7-methoxycoumarin-3-carboxylic acid (MC) and 7-diethylaminocoumarin-3-carboxylic acid (DAC) were used to thoroughly study Förster resonance energy transfer (FRET) in inclusion complexes. (1) H NMR evidence was given for the formation of a 1:1 inclusion complex between β-cyclodextrin (β-CD) and the fluorophore moieties of model compounds. The binding constant was 20 times higher for DAC than for MC derivatives. Molecular modeling provided additional information. The UV/Vis absorption and fluorescence properties were studied and the energy transfer process was quantified. Fluorescence quenching was particularly strong for the peptide derivatives. The presence of β-CDs reduced the FRET efficiency slightly. Dye-labeled peptide derivatives can thus be used to form inclusion complexes with β-CDs and retain most of their FRET properties. This paves the way for their subsequent use in analytical devices that are designed to measure the activity of matrix metalloproteinases.
authors.affiliation: SynVec, ADERA, 146 rue Léo Saignat, 33000 Bordeaux Cedex, (France); FRE3396 CNRS, Université Victor Segalen Bordeaux 2, 146 rue Léo Saignat, 33076 Bordeaux Cedex, (France).
authors.forename: Mohamed-Anis
authors.initials: MA
authors.lastname: Alouini
authors.forename: El-Farouck
authors.initials: el-F
authors.lastname: Moustoifa
authors.forename: Sandra
authors.initials: S
authors.lastname: Rubio-Albenque
authors.forename: Thomas
authors.initials: T
authors.lastname: Berthelot
authors.forename: Suzanne
authors.initials: S
authors.lastname: Fery-Forgues
authors.forename: Gérard
authors.initials: G
authors.lastname: Déléris
mesh_terms: D003374:Coumarins / Q000737:chemistry; D019855:Ethylene Glycol / Q000737:chemistry*; D031541:Fluorescence Resonance Energy Transfer; D005456:Fluorescent Dyes / Q000737:chemistry*; D008958:Models, Molecular; D010455:Peptides / Q000737:chemistry*; D047392:beta-Cyclodextrins / Q000737:chemistry*
chemical_list: D003374:Coumarins; D005456:Fluorescent Dyes; D010455:Peptides; D047392:beta-Cyclodextrins; C030123:coumarin; D019855:Ethylene Glycol; C031215:betadex
keywords: FRET; dyes/pigments; fluorescence; inclusion compounds; peptides