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Rational Design of a Redox-Labeled Chiral Target for an Enantioselective Aptamer-Based Electrochemical Binding Assay

Authors

  • Dr. Julie Moreau,

    1. ITODYS, UMR 7086 CNRS, Université Paris Diderot, Sorbonne Paris Cité, 15 rue Jean-Antoine de Baïf, 75205 Paris Cedex 13 (France)
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  • Lylian Challier,

    1. ITODYS, UMR 7086 CNRS, Université Paris Diderot, Sorbonne Paris Cité, 15 rue Jean-Antoine de Baïf, 75205 Paris Cedex 13 (France)
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  • Noémie Lalaoui,

    1. ITODYS, UMR 7086 CNRS, Université Paris Diderot, Sorbonne Paris Cité, 15 rue Jean-Antoine de Baïf, 75205 Paris Cedex 13 (France)
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  • Dr. François Mavré,

    1. Laboratoire d'Electrochimie Moléculaire, UMR 7591 CNRS, Université Paris Diderot, Sorbonne Paris Cité, 15 rue Jean-Antoine de Baïf, 75205 Paris Cedex 13 (France), Fax: (+33) 1-57-27-87-88
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  • Dr. Vincent Noël,

    1. ITODYS, UMR 7086 CNRS, Université Paris Diderot, Sorbonne Paris Cité, 15 rue Jean-Antoine de Baïf, 75205 Paris Cedex 13 (France)
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  • Dr. Benoît Limoges,

    1. Laboratoire d'Electrochimie Moléculaire, UMR 7591 CNRS, Université Paris Diderot, Sorbonne Paris Cité, 15 rue Jean-Antoine de Baïf, 75205 Paris Cedex 13 (France), Fax: (+33) 1-57-27-87-88
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  • Prof. Bernd Schöllhorn,

    Corresponding author
    1. Laboratoire d'Electrochimie Moléculaire, UMR 7591 CNRS, Université Paris Diderot, Sorbonne Paris Cité, 15 rue Jean-Antoine de Baïf, 75205 Paris Cedex 13 (France), Fax: (+33) 1-57-27-87-88
    • Laboratoire d'Electrochimie Moléculaire, UMR 7591 CNRS, Université Paris Diderot, Sorbonne Paris Cité, 15 rue Jean-Antoine de Baïf, 75205 Paris Cedex 13 (France), Fax: (+33) 1-57-27-87-88

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  • Dr. Claire Fave

    Corresponding author
    1. Laboratoire d'Electrochimie Moléculaire, UMR 7591 CNRS, Université Paris Diderot, Sorbonne Paris Cité, 15 rue Jean-Antoine de Baïf, 75205 Paris Cedex 13 (France), Fax: (+33) 1-57-27-87-88
    2. ITODYS, UMR 7086 CNRS, Université Paris Diderot, Sorbonne Paris Cité, 15 rue Jean-Antoine de Baïf, 75205 Paris Cedex 13 (France)
    • Laboratoire d'Electrochimie Moléculaire, UMR 7591 CNRS, Université Paris Diderot, Sorbonne Paris Cité, 15 rue Jean-Antoine de Baïf, 75205 Paris Cedex 13 (France), Fax: (+33) 1-57-27-87-88

    Search for more papers by this author

Abstract

A series of redox-labeled L-tyrosinamide (L-Tym) derivatives was prepared and the nature of the functional group and the chain length of the spacer were systematically varied in a step-by-step affinity optimization process of the tracer for the L-Tym aptamer. The choice of the labeling position on L-Tym proved to be crucial for the molecular recognition event, which could be monitored by cyclic voltammetry and is based on the different diffusion rates of free and bound targets in solution. From this screening approach an efficient electroactive tracer emerged. Comparable dissociation constants Kd were obtained for the unlabeled and labeled targets in direct or competitive binding assays. The enantiomeric tracer was prepared and its enantioselective recognition by the corresponding anti-D-Tym aptamer was demonstrated. The access to both enantiomeric tracer molecules opens the door for the development of one-pot determination of the enantiomeric excess when using different labels with well-separated redox potentials for each enantiomer.

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