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@article{1751079,
author = {Simonova, A. and Magrina, I. and Sykorova, V. and Pohl, R. and Ortiz, M. and Havran, L. and Fojta, Miroslav and O Sullivan, C.K. and Hocek, M.},
article_location = {WEINHEIM},
article_number = {6},
doi = {http://dx.doi.org/10.1002/chem.201904700},
keywords = {DNA; electrochemistry; ferrocenes; nucleobases; redox labelling},
language = {eng},
issn = {0947-6539},
journal = {Chemistry - A European Journal},
title = {Tuning of Oxidation Potential of Ferrocene for Ratiometric Redox Labeling and Coding of Nucleotides and DNA},
url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.201904700},
volume = {26},
year = {2020}
}
TY - JOUR
ID - 1751079
AU - Simonova, A. - Magrina, I. - Sykorova, V. - Pohl, R. - Ortiz, M. - Havran, L. - Fojta, Miroslav - O Sullivan, C.K. - Hocek, M.
PY - 2020
TI - Tuning of Oxidation Potential of Ferrocene for Ratiometric Redox Labeling and Coding of Nucleotides and DNA
JF - Chemistry - A European Journal
VL - 26
IS - 6
SP - 1286-1291
EP - 1286-1291
PB - Wiley
SN - 09476539
KW - DNA
KW - electrochemistry
KW - ferrocenes
KW - nucleobases
KW - redox labelling
UR - https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.201904700
N2 - Three sets of 7-deazaadenine and cytosine nucleosides and nucleoside triphosphates bearing either unsubstituted ferrocene, octamethylferrocene and ferrocenecarboxamide linked through an alkyne tether to position 7 or 5, respectively, were designed and synthesized. The modified dNFcXTPs were good substrates for KOD XL DNA polymerase in primer extension and were used for enzymatic synthesis of redox-labelled DNA probes. Square-wave voltammetry showed that the octamethylferrocene oxidation potential was shifted to lower values, whilst the ferrocenecarboxamide was shifted to higher potentials, as compared to ferrocene. Tailed PEX products containing different ratios of Fc-labelled A (dAFc) and FcPa-labelled C (dCFcPa) were synthesized and hybridized with capture oligonucleotides immobilized on gold electrodes to study the electrochemistry of the redoxlabelled DNA. Clearly distinguishable, fully orthogonal and ratiometric peaks were observed for the dAFc and dCFcPa bases in DNA, demonstrating their potential for use in redox coding of nucleobases and for the direct electrochemical measurement of the relative ratio of nucleobases in an unknown sequence of DNA.
ER -
SIMONOVA, A., I. MAGRINA, V. SYKOROVA, R. POHL, M. ORTIZ, L. HAVRAN, Miroslav FOJTA, C.K. O SULLIVAN a M. HOCEK. Tuning of Oxidation Potential of Ferrocene for Ratiometric Redox Labeling and Coding of Nucleotides and DNA. \textit{Chemistry - A European Journal}. WEINHEIM: Wiley, 2020, roč.~26, č.~6, s.~1286-1291. ISSN~0947-6539. Dostupné z: https://dx.doi.org/10.1002/chem.201904700.
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