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Carborane- or Metallacarborane-Linked Nucleotides for Redox Labeling. Orthogonal Multipotential Coding of all Four DNA Bases for Electrochemical Analysis and Sequencing
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SYSNO ASEP 0542459 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Carborane- or Metallacarborane-Linked Nucleotides for Redox Labeling. Orthogonal Multipotential Coding of all Four DNA Bases for Electrochemical Analysis and Sequencing Author(s) Kodr, David (UOCHB-X) ORCID
Yenice, C. P. (ES)
Simonova, Anna (UOCHB-X)
Saftić, D. P. (PL)
Pohl, Radek (UOCHB-X) RID, ORCID
Sýkorová, Veronika (UOCHB-X) ORCID, RID
Ortiz, M. (ES)
Havran, Luděk (BFU-R) RID, ORCID
Fojta, Miroslav (BFU-R) RID, ORCID
Lesnikowski, Z. J. (PL)
O'Sullivan, C. K. (ES)
Hocek, Michal (UOCHB-X) RID, ORCIDSource Title Journal of the American Chemical Society. - : American Chemical Society - ISSN 0002-7863
Roč. 143, č. 18 (2021), s. 7124-7134Number of pages 11 s. Language eng - English Country US - United States Keywords neutron-capture therapy ; nucleoside triphosphates ; sensors OECD category Organic chemistry R&D Projects GX20-00885X 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 UOCHB-X - RVO:61388963 ; BFU-R - RVO:68081707 UT WOS 000651748000044 EID SCOPUS 85106466637 DOI https://doi.org/10.1021/jacs.1c02222 Annotation We report a series of 2′-deoxyribonucleoside triphosphates bearing dicarba-nido-undecaborate ([C2B9H11]1–), [3,3′-iron-bis(1,2-dicarbollide)]− (FESAN, [Fe(C2B9H11)2]2–) or [3,3′-cobalt-bis(1,2-dicarbollide)]− (COSAN, [Co(C2B9H11)2]2–) groups prepared either through the Sonogashira cross-coupling or the CuAAC click reaction. The modified dNXTPs were substrates for KOD XL DNA polymerase in enzymatic synthesis of modified DNA through primer extension (PEX). The nido-carborane- and FESAN-modified nucleotides gave analytically useful oxidation signals in square-wave voltammetry and were used for redox labeling of DNA. The redox-modified DNA probes were prepared by PEX using tailed primers and were hybridized to electrode (gold or glassy carbon) containing capture oligonucleotides. The combination of nido-carborane- and FESAN-linked nucleotides with 7-ferrocenylethynyl-7-deaza-dATP and 7-deaza-dGTP allowed polymerase synthesis of DNA fully modified at all four nucleobases, and each of the redox labels gave four differentiable and ratiometric signals in voltammetry. Thus, the combination of these four redox labels constitutes the first fully orthogonal redox coding of all four canonical nucleobases, which can be used for determination of nucleobase composition of short DNA stretches in one simple PEX experiment with electrochemical readout. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2022 Electronic address https://doi.org/10.1021/jacs.1c02222
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