SIMONOVA, A., I. MAGRINA, V. SYKOROVA, R. POHL, M. ORTIZ, L. HAVRAN, Miroslav FOJTA, C.K. O SULLIVAN and M. HOCEK. Tuning of Oxidation Potential of Ferrocene for Ratiometric Redox Labeling and Coding of Nucleotides and DNA. Chemistry - A European Journal. WEINHEIM: Wiley, 2020, vol. 26, No 6, p. 1286-1291. ISSN 0947-6539. Available from: https://dx.doi.org/10.1002/chem.201904700.
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Basic information
Original name Tuning of Oxidation Potential of Ferrocene for Ratiometric Redox Labeling and Coding of Nucleotides and DNA
Authors SIMONOVA, A., I. MAGRINA, V. SYKOROVA, R. POHL, M. ORTIZ, L. HAVRAN, Miroslav FOJTA (203 Czech Republic, guarantor, belonging to the institution), C.K. O SULLIVAN and M. HOCEK.
Edition Chemistry - A European Journal, WEINHEIM, Wiley, 2020, 0947-6539.
Other information
Original language English
Type of outcome Article in a journal
Field of Study 10403 Physical chemistry
Country of publisher Germany
Confidentiality degree is not subject to a state or trade secret
WWW URL
Impact factor Impact factor: 5.236
RIV identification code RIV/00216224:14740/20:00118367
Organization unit Central European Institute of Technology
Doi http://dx.doi.org/10.1002/chem.201904700
UT WoS 000506258100001
Keywords in English DNA; electrochemistry; ferrocenes; nucleobases; redox labelling
Tags rivok
Tags International impact, Reviewed
Changed by Changed by: Mgr. Pavla Foltynová, Ph.D., učo 106624. Changed: 10/3/2021 16:19.
Abstract
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.
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