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Vicinal Diol-Tethered Nucleobases as Targets for DNA Redox Labeling with Osmate Complexes
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SYSNO ASEP 0520341 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Vicinal Diol-Tethered Nucleobases as Targets for DNA Redox Labeling with Osmate Complexes Author(s) Havranová-Vidláková, Pavlína (BFU-R) ORCID
Krömer, Matouš (UOCHB-X) RID, ORCID
Sýkorová, Veronika (UOCHB-X) ORCID, RID
Trefulka, Mojmír (BFU-R) RID, ORCID
Fojta, Miroslav (BFU-R) RID, ORCID
Havran, Luděk (BFU-R) RID, ORCID
Hocek, Michal (UOCHB-X) RID, ORCIDNumber of authors 7 Source Title Chembiochem. - : Wiley - ISSN 1439-4227
Roč. 21, 1/2 (2020), s. 171-180Number of pages 11 s. Publication form Print - P Language eng - English Country DE - Germany Keywords nucleoside triphosphates ; electrochemistry ; inhibition ; DNA Subject RIV CE - Biochemistry OECD category Biochemistry and molecular biology Subject RIV - cooperation Institute of Organic Chemistry and Biochemistry - Electrochemistry R&D Projects GA15-08434S GA ČR - Czech Science Foundation (CSF) EF16_019/0000729 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Method of publishing Limited access Institutional support BFU-R - RVO:68081707 ; UOCHB-X - RVO:61388963 UT WOS 000481172600001 EID SCOPUS 85070713153 DOI 10.1002/cbic.201900388 Annotation Six-valent osmium (osmate) complexes with nitrogenous ligands have previously been used for the modification and redox labeling of biomolecules involving vicinal diol moieties (typically, saccharides or RNA). In this work, aliphatic (3,4-dihydroxybutyl and 3,4-dihydroxybut-1-ynyl) or cyclic (6-oxo-6-(cis-3,4-dihydroxypyrrolidin-1-yl)hex-2-yn-1-yl, PDI) vicinal diols are attached to nucleobases to functionalize DNA for subsequent redox labeling with osmium(VI) complexes. The diol-linked 2 '-deoxyribonucleoside triphosphates were used for the polymerase synthesis of diol-linked DNA, which, upon treatment with K2OsO3 and bidentate nitrogen ligands, gave the desired Os-labeled DNA, which were characterized by means of the gel-shift assay and ESI-MS. Through ex situ square-wave voltammetry at a basal plane pyrolytic graphite electrode, the efficiency of modification/labeling of individual diols was evaluated. The results show that the cyclic cis-diol (PDI) was a better target for osmylation than that of the flexible aliphatic ones (alkyl- or alkynyl-linked). The osmate adduct-specific voltammetric signal obtained for Os-VI-treated DNA decorated with PDI showed good proportionality to the number of PDI per DNA molecule. The Os-VI reagents (unlike OsO4) do not attack nucleobases, thus offering specificity of modification on the introduced glycol targets. Workplace Institute of Biophysics Contact Jana Poláková, polakova@ibp.cz, Tel.: 541 517 244 Year of Publishing 2021 Electronic address https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/cbic.201900388
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