Interaction of Fluorescently Labeled Triethyleneglycol and Peptide Derivatives with β-Cyclodextrin

Authors

  • Dr. Mohamed-Anis Alouini ,

    1. SynVec, ADERA, 146 rue Léo Saignat, 33000 Bordeaux Cedex, (France)
    2. FRE3396 CNRS, Université Victor Segalen Bordeaux 2, 146 rue Léo Saignat, 33076 Bordeaux Cedex, (France)
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  • Dr. El-Farouck Moustoifa,

    1. FRE3396 CNRS, Université Victor Segalen Bordeaux 2, 146 rue Léo Saignat, 33076 Bordeaux Cedex, (France)
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  • Dr. Sandra Rubio-Albenque,

    1. FRE3396 CNRS, Université Victor Segalen Bordeaux 2, 146 rue Léo Saignat, 33076 Bordeaux Cedex, (France)
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  • Dr. Thomas Berthelot,

    Corresponding author
    1. Laboratory of Chemistry of Surfaces and Interfaces, CEA Saclay, IRAMIS/SPCSI, 91191, Gif-sur-Yvette Cedex, (France)
    • Thomas Berthelot, Laboratory of Chemistry of Surfaces and Interfaces, CEA Saclay, IRAMIS/SPCSI, 91191, Gif-sur-Yvette Cedex, (France)

      Suzanne Fery-Forgues , Université de Toulouse, ITAV-USR 3505, 31106 Toulouse (France)

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  • Dr. Suzanne Fery-Forgues ,

    Corresponding author
    1. Université de Toulouse, ITAV-USR 3505, 31106 Toulouse (France)
    2. CNRS, ITAV-USR3505, 31106 Toulouse (France)
    3. Université de Toulouse, IMRCP-UMR 5623, 31062 Toulouse (France)
    4. CNRS, IMRCP-UMR5623, 31062 Toulouse (France)
    • Thomas Berthelot, Laboratory of Chemistry of Surfaces and Interfaces, CEA Saclay, IRAMIS/SPCSI, 91191, Gif-sur-Yvette Cedex, (France)

      Suzanne Fery-Forgues , Université de Toulouse, ITAV-USR 3505, 31106 Toulouse (France)

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  • Prof. Gérard Déléris

    1. FRE3396 CNRS, Université Victor Segalen Bordeaux 2, 146 rue Léo Saignat, 33076 Bordeaux Cedex, (France)
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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. 1H 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.

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