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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

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, ORCID}
Source Title	Journal of the American Chemical Society. - : American Chemical Society - ISSN 0002-7863 Roč. 143, č. 18 (2021), s. 7124-7134
Number 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	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 ; Viktorie Chládková, Tel.: 232 002 434
Year of Publishing	2022
Electronic address	https://doi.org/10.1021/jacs.1c02222

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