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Searching for Electrochemical Reduction Mechanism of Azidophenyl DNA Labels
Daňhel, Aleš ; Trošanová, Zuzana ; Balintová, Jana ; Hocek, Michal ; Fojta, Miroslav
This contribution brings new information to sporadic scientific results concerned to electrochemical reduction of aromatic azides. Selected compounds used as perspective DNA labels or their structural constituents such as, 4-azidophenyltrifluoroboronic acid, 4-azidophenyl modified deoxycytidine and next probable analogous compounds and/or products of their reduction, were voltammetrically studied and compared to each other in order to reveal a mechanism of their electrochemical reduction at mercury electrodes in aqueous media. Preliminary results obtained by cyclic voltammetry at mercury and carbon based electrodes and by mass spectrometry of the products isolated from batch electrolysis on mercury pool by preparative chromatography are discussed.
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Voltammetric Behavior of 4-Aminophthalimide Label using Hanging Mercury Drop Electrode
Ferenčíková, Z. ; Daňhel, Aleš ; Riedl, Jan ; Hocek, Michal ; Fojta, Miroslav
4-aminophthalimide (API), covalently attached to nucleotide (dCTP or dATP) has recently beendesigned as a fluorescent label for the detection of DNA-protein interaction. However API is electrochemically reducible and therefore it is possible to use alternatively the API-modified nuclotides as DNA redox labels. The electrochemical behavior of labeled nucleotides and labeled DNA was studied using cyclic voltammetry and transfer stripping cyclic voltammetry at hanging mercury drop electrode. Observed CVs showed irreversible reduction signals of 4-aminophthalimide label without production of consequently oxidizable/reducible species.
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Electrochemical analysis of DNA using switchable redox moieties
Fojta, Miroslav ; Daňhel, Aleš ; Horáková Brázdilová, Petra ; Plucnara, Medard ; Pivoňková, Hana ; Havran, Luděk ; Vidláková, Pavlína ; Raindlová, Veronika ; Balintová, Jana ; Macíčková-Cahová, Hana ; Hocek, Michal
Labelling of DNA with electrochemically active moieties proved to be a convenient way to the development of electrochemical techniques for the sequence-specific DNA sensing. Through combinations of various labels differing in redox potentials, independent redox coding of different DNA sequences or individual nucleobases can be attained. Applications possibilities of electrochemistry in analysis of modified DNAs are further extended by facile monitoring of chemical conversion of reactive groups on DNA during post-labelling with ultimate redox labels. In addition, controlled in situ electrochemical conversions of specific intrinsic and extrinsic DNA components can be utilized to switch their electrochemical signals and improve signal resolution.
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