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Electrochemical transduction of DNA hybridization at modified electrodes by using an electroactive pyridoacridone intercalator

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Abstract

A synthetic redox probe structurally related to natural pyridoacridones was designed and electrochemically characterised. These heterocycles behave as DNA intercalators due to their extended planar structure that promotes stacking in between nucleic acid base pairs. Electrochemical characterization by cyclic voltammetry revealed a quasi-reversible electrochemical behaviour occurring at a mild negative potential in aqueous solution. The study of the mechanism showed that the iminoquinone redox moiety acts similarly to quinone involving a two-electron reduction coupled with proton transfer. The easily accessible potential region with respect to aqueous electro-inactive window makes the pyridoacridone ring suitable for the indirect electrochemical detection of chemically unlabelled DNA. Its usefulness as electrochemical hybridization indicator was assessed on immobilised DNA and compared to doxorubicin. The voltamperometric response of the intercalator acts as an indicator of the presence of double-stranded DNA at the electrode surface and allows the selective transduction of immobilised oligonucleotide hybridization at both macro- and microscale electrodes.

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Authors and Affiliations

  1. Univ. Bordeaux, ISM, UMR 5255, 33400, Talence, France

    Laurent Bouffier

  2. CNRS, ISM, UMR 5255, 33400, Talence, France

    Laurent Bouffier

  3. CREAB/SI3M/DRFMC, UMR 5819, CEA Grenoble, 17 Avenue des Martyrs, 38054, Grenoble cedex 9, France

    Bingquan Stuart Wang, André Roget, Thierry Livache & Pascal Mailley

  4. Genzyme Corporation, 49 New York Avenue, Framingham, MA, 01701, USA

    Bingquan Stuart Wang

  5. Department of Pharmacomolecular Chemistry, UMR 5063 & FR 2607 CNRS/Joseph Fourier University, BP 53, 38041, Grenoble cedex 9, France

    Martine Demeunynck

  6. Laboratory of Electricity Storage, LSE/DTS, CEA, 50 Avenue du Lac Leman, 73377, Le Bourget du Lac cedex, France

    Pascal Mailley

Authors
  1. Laurent Bouffier
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  2. Bingquan Stuart Wang
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  3. André Roget
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  4. Thierry Livache
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  5. Martine Demeunynck
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  6. Pascal Mailley
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Correspondence to Laurent Bouffier.

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Published in the special issue Analytical Science in France with guest editors Christian Rolando and Philippe Garrigues.

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Bouffier, L., Wang, B.S., Roget, A. et al. Electrochemical transduction of DNA hybridization at modified electrodes by using an electroactive pyridoacridone intercalator. Anal Bioanal Chem 406, 1163–1172 (2014). https://doi.org/10.1007/s00216-013-7314-2

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  • DOI: https://doi.org/10.1007/s00216-013-7314-2

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