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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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