Anthraquinone as a Redox Label for DNA: Synthesis, Enzymatic Incorporation, and Electrochemistry of Anthraquinone‐Modified Nucleosides, Nucleotides, and DNA

Balintová, Jana; Pohl, Radek; Horáková, Petra; Vidláková, Pavlína; Havran, Luděk; Fojta, Miroslav; Hocek, Michal

doi:10.1002/chem.201101883

Cited by 64 publications

(40 citation statements)

References 46 publications

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“…Various labels can be independently detected due to sufficiently different redox potentials from those of natural DNA bases as well as from each other. In addition, in some cases the resolution can be improved via electrochemical [18,19] or chemical [17] transformation of the label(s) incorporated in DNA.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical behavior of 7-deazaguanine- and 7-deazaadenine-modified DNA at the hanging mercury drop electrode

et al. 2015

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DNA modification with synthetic analogs of natural nucleotides and/or their conjugates with external redox active groups is applied in the development of electrochemical DNA sensors or assay for DNA hybridization, SNP typing, DNA damage and so forth. 7-Deazapurines (Pu*) are analogs of natural purine bases in which N7 atom is replaced by CH group. The Pu* bases retain Watson-Crick base pairing of their parent purines (and the ability to form duplex DNA) but are incapable of Hoogsteen pairing (and thus cannot be involved in triplex or quadruples DNA structures). Previously, we studied electrochemical oxidation of Pu* residues in DNA fragments (prepared by PCR in the presence of Pu* deoxynucleoside triphosphates) at a carbon electrode and reported on significantly lower potentials of oxidation of both 7-deazaguanine (G*) and 7-deazaadenine (A*), compared to natural guanine (G) and adenine (A), respectively. In this work, we studied faradaic and tensammetric responses of G*-or A*-modified DNA on the hanging mercury drop electrode (HMDE). While A* was reduced at the HMDE, giving rise to a similar irreversible cathodic peak as the natural A, G* did not yield any peak analogous to the peak G due to guanine, in agreement with a loss of corresponding redox site in G*. Responses of DNA modified with A* were relatively similar to those of unmodified DNA (albeit we observed certain differences in tensammetric peak currents). Effects of G substitution by G* were more pronounced, being reflected in diminution of peak due to guanine, decrease of the peak CA (due to cytosine and adenine reduction) and in significantly changed shape of tensammetric DNA signals, indicating altered adsorption/desorption processes. While substitution of A by A* resulted in certain destabilization of the DNA duplex at the negatively charged HMDE surface (in qualitative agreement with significantly decreased melting temperature of the same DNA duplexes in solution), G*-modified duplex DNA displayed apparently lower susceptibility to surface denaturation. Graphical abstract -1.5 -1.2 -0.9 -0.6 -0.3 0.0 -0.9 -0.6 -0.3 0.0

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Section: Introductionmentioning

confidence: 99%

Electrochemical behavior of 7-deazaguanine- and 7-deazaadenine-modified DNA at the hanging mercury drop electrode

et al. 2015

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“…Both the inherent electrochemistry of nucleic acids and the electrochemistry of additional DNA labels have been extensively used in diverse bioanalytical applications 4. We have previously developed several new redox labels, including ferrocene,5 aminophenyl and nitrophenyl,6 [Os(bpy) 3 ] (bpy=2,2′‐bipyridyl),7 tetrathiafulvalene,8 anthraquinone,9 alkylsulfanylphenyl,10 hydrazones,11 and so on, and by combining four different labels for the four nucleobases, established the first generation of multipotential redox coding7 of DNA and applied it in minisequencing. However, in this first generation of redox labeling, only one or two labels (one reducible and one oxidizable)6 were incorporated and detected in one DNA molecule.…”

Section: Introductionmentioning

confidence: 99%

Benzofurazane as a New Redox Label for Electrochemical Detection of DNA: Towards Multipotential Redox Coding of DNA Bases

Balintová

Plucnara

Vidláková

et al. 2013

Chemistry A European J

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Benzofurazane has been attached to nucleosides and dNTPs, either directly or through an acetylene linker, as a new redox label for electrochemical analysis of nucleotide sequences. Primer extension incorporation of the benzofurazane-modified dNTPs by polymerases has been developed for the construction of labeled oligonucleotide probes. In combination with nitrophenyl and aminophenyl labels, we have successfully developed a three-potential coding of DNA bases and have explored the relevant electrochemical potentials. The combination of benzofurazane and nitrophenyl reducible labels has proved to be excellent for ratiometric analysis of nucleotide sequences and is suitable for bioanalytical applications.

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“…2 We and others have previously reported labelling of DNA by diverse redox labels, including ferrocene, 3,4 aminoand nitrophenyl, 5 Os(bpy) 3 -, 6 anthraquinone, 3,7,8 benzofurazane, 9 azidophenyl, 10 methylene-blue, 11,12 polyoxometalates 13 or methoxyphenol 14 through polymerase incorporation of redox-labelled 2′-deoxyribonucleoside triphosphate (dNTP). Combination of several orthogonal redox labels could be used for multipotential redox-coding of DNA nucleobases for development of electrochemical minisequencing techniques.…”

Section: Introductionmentioning

confidence: 99%

“…The orthogonality requires labelling of each nucleobase by a different redox-active group (having a different redox potential), and each label should be "readable" in the presence of all the other labels and give a ratiometric signal intensity. Our first generations of redox coding 5,7 suffered from weak and overlapping signals, limited stability and difficult incorporation of some labels into DNA. More recently, we reported the first orthogonal and ratiometric set of two reducible labels (nitrophenyl and benzofurazane) useful for electrochemical minisequencing of short DNA stretches.…”

Section: Introductionmentioning

confidence: 99%

Phenothiazine-linked nucleosides and nucleotides for redox labelling of DNA

et al. 2017

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Nucleosides and 2'-deoxyribonucleoside triphosphates (dNTPs) bearing phenothiazine (PT) attached to a nucleobase (cytosine or 7-deazaadenine) either directly or through an acetylene linker were prepared through Suzuki or Sonogashira cross-coupling and triphosphorylation, and were studied as building blocks for polymerase construction of modified DNA. The directly PT-substituted dNTPs were better substrates for polymerases than the alkyne-linked dNTPs but all of them were used in enzymatic synthesis of DNA using primer extension, nicking enzyme amplification, PCR or 3'-tail labelling by terminal deoxynucleotidyl transferase. The phenothiazine served as an oxidizable redox label (giving two analytically useful signals of oxidation on electrode) for nucleosides and DNA and was also used in orthogonal combination with previously developed benzofurazane or nitrophenyl labels for redox coding of DNA bases. Therefore, the title PT-linked dNTPs are useful additions to the portfolio of nucleotides for enzymatic synthesis of redox-labelled DNA for electrochemical analysis.

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Anthraquinone as a Redox Label for DNA: Synthesis, Enzymatic Incorporation, and Electrochemistry of Anthraquinone‐Modified Nucleosides, Nucleotides, and DNA

Cited by 64 publications

References 46 publications

Electrochemical behavior of 7-deazaguanine- and 7-deazaadenine-modified DNA at the hanging mercury drop electrode

Electrochemical behavior of 7-deazaguanine- and 7-deazaadenine-modified DNA at the hanging mercury drop electrode

Benzofurazane as a New Redox Label for Electrochemical Detection of DNA: Towards Multipotential Redox Coding of DNA Bases

Phenothiazine-linked nucleosides and nucleotides for redox labelling of DNA

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