Voltammetric Study of dsDNA Modified by Multi-redox Label Based on N-methyl-4-hydrazino-7-nitrobenzofurazan

Ales Danhel, Veronika Raindlova, Ludek Havran, Jiri Barek, Michal Hocek, Miroslav Fojta

    Research output: Contribution to journalArticle

    7 Citations (Scopus)

    Abstract

    Voltammetric behaviour of novel synthetic multi-redox DNA label N-methyl-4-hydrazino-7-nitrobenzofurazan (NBF), a deoxycytidine monophosphate conjugate with NBF via formylthiophene linker (dCNBFMP), and NBF labeled model short double stranded DNA (dsDNA-NBF) were systematically studied at mercury meniscus modified silver solid amalgam electrode (m-AgSAE) for the first time in this work. Successful enzymatic incorporation of the NBF labeled deoxycytidine triphosphate into the DNA was confirmed and the dsDNA-NBF offered new more positive cathodic signals at -520 mV and -1160 mV, compared to the nucleic acid itself. Used modification resulted in increase of selectivity and sensitivity of the DNA voltammetric determination. Next to the pioneering voltammetric behaviour of all studied compounds at m-AgSAE, electroanalytical methods based on cyclic voltammetry, adsorptive stripping cyclic voltammetry and open circuit transfer stripping cyclic voltammetry were developed for sensitive detection of these (bio)molecules. Furthermore, utilization of variable negative vertex potential and scan rate was also observed and their appropriate selection considerably influenced registered peaks on cyclic voltammograms. These redox processes increased signal response diversity and offered utilization of signal switch on/off technique, as well. Tentative electrochemical reduction mechanisms of the NBF, dCNBFMP and dsDNA-NBF were proposed and discussed, together with possibilities and limitations of the NBF + m-AgSAE system.

    Original languageEnglish
    Pages (from-to)348-357
    Number of pages10
    JournalElectrochimica Acta
    Volume129
    DOIs
    Publication statusPublished - 20 May 2014

    Fingerprint

    Cyclic voltammetry
    Labels
    Deoxycytidine Monophosphate
    Mercury amalgams
    Mercury (metal)
    Nucleic acids
    Mercury
    Silver
    Nucleic Acids
    Switches
    Electrodes
    Molecules
    Networks (circuits)
    N-methyl-4-hydrazino-7-nitrobenzofurazan
    Oxidation-Reduction
    2'-deoxycytidine 5'-triphosphate

    Keywords

    • DNA
    • N-methyl-4-hydrazino-7-nitrobenzofurazan
    • Redox labeling
    • Silver solid amalgam electrode
    • Voltammetry

    ASJC Scopus subject areas

    • Chemical Engineering(all)
    • Electrochemistry

    Cite this

    Voltammetric Study of dsDNA Modified by Multi-redox Label Based on N-methyl-4-hydrazino-7-nitrobenzofurazan. / Danhel, Ales; Raindlova, Veronika; Havran, Ludek; Barek, Jiri; Hocek, Michal; Fojta, Miroslav.

    In: Electrochimica Acta, Vol. 129, 20.05.2014, p. 348-357.

    Research output: Contribution to journalArticle

    Danhel, Ales ; Raindlova, Veronika ; Havran, Ludek ; Barek, Jiri ; Hocek, Michal ; Fojta, Miroslav. / Voltammetric Study of dsDNA Modified by Multi-redox Label Based on N-methyl-4-hydrazino-7-nitrobenzofurazan. In: Electrochimica Acta. 2014 ; Vol. 129. pp. 348-357.
    @article{60005dc2bcd240a08fd91990bb3a7bff,
    title = "Voltammetric Study of dsDNA Modified by Multi-redox Label Based on N-methyl-4-hydrazino-7-nitrobenzofurazan",
    abstract = "Voltammetric behaviour of novel synthetic multi-redox DNA label N-methyl-4-hydrazino-7-nitrobenzofurazan (NBF), a deoxycytidine monophosphate conjugate with NBF via formylthiophene linker (dCNBFMP), and NBF labeled model short double stranded DNA (dsDNA-NBF) were systematically studied at mercury meniscus modified silver solid amalgam electrode (m-AgSAE) for the first time in this work. Successful enzymatic incorporation of the NBF labeled deoxycytidine triphosphate into the DNA was confirmed and the dsDNA-NBF offered new more positive cathodic signals at -520 mV and -1160 mV, compared to the nucleic acid itself. Used modification resulted in increase of selectivity and sensitivity of the DNA voltammetric determination. Next to the pioneering voltammetric behaviour of all studied compounds at m-AgSAE, electroanalytical methods based on cyclic voltammetry, adsorptive stripping cyclic voltammetry and open circuit transfer stripping cyclic voltammetry were developed for sensitive detection of these (bio)molecules. Furthermore, utilization of variable negative vertex potential and scan rate was also observed and their appropriate selection considerably influenced registered peaks on cyclic voltammograms. These redox processes increased signal response diversity and offered utilization of signal switch on/off technique, as well. Tentative electrochemical reduction mechanisms of the NBF, dCNBFMP and dsDNA-NBF were proposed and discussed, together with possibilities and limitations of the NBF + m-AgSAE system.",
    keywords = "DNA, N-methyl-4-hydrazino-7-nitrobenzofurazan, Redox labeling, Silver solid amalgam electrode, Voltammetry",
    author = "Ales Danhel and Veronika Raindlova and Ludek Havran and Jiri Barek and Michal Hocek and Miroslav Fojta",
    year = "2014",
    month = "5",
    day = "20",
    doi = "10.1016/j.electacta.2014.02.137",
    language = "English",
    volume = "129",
    pages = "348--357",
    journal = "Electrochimica Acta",
    issn = "0013-4686",
    publisher = "Elsevier Limited",

    }

    TY - JOUR

    T1 - Voltammetric Study of dsDNA Modified by Multi-redox Label Based on N-methyl-4-hydrazino-7-nitrobenzofurazan

    AU - Danhel, Ales

    AU - Raindlova, Veronika

    AU - Havran, Ludek

    AU - Barek, Jiri

    AU - Hocek, Michal

    AU - Fojta, Miroslav

    PY - 2014/5/20

    Y1 - 2014/5/20

    N2 - Voltammetric behaviour of novel synthetic multi-redox DNA label N-methyl-4-hydrazino-7-nitrobenzofurazan (NBF), a deoxycytidine monophosphate conjugate with NBF via formylthiophene linker (dCNBFMP), and NBF labeled model short double stranded DNA (dsDNA-NBF) were systematically studied at mercury meniscus modified silver solid amalgam electrode (m-AgSAE) for the first time in this work. Successful enzymatic incorporation of the NBF labeled deoxycytidine triphosphate into the DNA was confirmed and the dsDNA-NBF offered new more positive cathodic signals at -520 mV and -1160 mV, compared to the nucleic acid itself. Used modification resulted in increase of selectivity and sensitivity of the DNA voltammetric determination. Next to the pioneering voltammetric behaviour of all studied compounds at m-AgSAE, electroanalytical methods based on cyclic voltammetry, adsorptive stripping cyclic voltammetry and open circuit transfer stripping cyclic voltammetry were developed for sensitive detection of these (bio)molecules. Furthermore, utilization of variable negative vertex potential and scan rate was also observed and their appropriate selection considerably influenced registered peaks on cyclic voltammograms. These redox processes increased signal response diversity and offered utilization of signal switch on/off technique, as well. Tentative electrochemical reduction mechanisms of the NBF, dCNBFMP and dsDNA-NBF were proposed and discussed, together with possibilities and limitations of the NBF + m-AgSAE system.

    AB - Voltammetric behaviour of novel synthetic multi-redox DNA label N-methyl-4-hydrazino-7-nitrobenzofurazan (NBF), a deoxycytidine monophosphate conjugate with NBF via formylthiophene linker (dCNBFMP), and NBF labeled model short double stranded DNA (dsDNA-NBF) were systematically studied at mercury meniscus modified silver solid amalgam electrode (m-AgSAE) for the first time in this work. Successful enzymatic incorporation of the NBF labeled deoxycytidine triphosphate into the DNA was confirmed and the dsDNA-NBF offered new more positive cathodic signals at -520 mV and -1160 mV, compared to the nucleic acid itself. Used modification resulted in increase of selectivity and sensitivity of the DNA voltammetric determination. Next to the pioneering voltammetric behaviour of all studied compounds at m-AgSAE, electroanalytical methods based on cyclic voltammetry, adsorptive stripping cyclic voltammetry and open circuit transfer stripping cyclic voltammetry were developed for sensitive detection of these (bio)molecules. Furthermore, utilization of variable negative vertex potential and scan rate was also observed and their appropriate selection considerably influenced registered peaks on cyclic voltammograms. These redox processes increased signal response diversity and offered utilization of signal switch on/off technique, as well. Tentative electrochemical reduction mechanisms of the NBF, dCNBFMP and dsDNA-NBF were proposed and discussed, together with possibilities and limitations of the NBF + m-AgSAE system.

    KW - DNA

    KW - N-methyl-4-hydrazino-7-nitrobenzofurazan

    KW - Redox labeling

    KW - Silver solid amalgam electrode

    KW - Voltammetry

    UR - http://www.scopus.com/inward/record.url?scp=84896912789&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=84896912789&partnerID=8YFLogxK

    U2 - 10.1016/j.electacta.2014.02.137

    DO - 10.1016/j.electacta.2014.02.137

    M3 - Article

    VL - 129

    SP - 348

    EP - 357

    JO - Electrochimica Acta

    JF - Electrochimica Acta

    SN - 0013-4686

    ER -