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Lipid-linked nucleoside triphosphates for enzymatic synthesis of hydrophobic oligonucleotides with enhanced membrane anchoring efficiency
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SYSNO ASEP 0571288 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Lipid-linked nucleoside triphosphates for enzymatic synthesis of hydrophobic oligonucleotides with enhanced membrane anchoring efficiency Author(s) Kodr, David (UOCHB-X) ORCID
Kužmová, Erika (UOCHB-X) ORCID
Pohl, Radek (UOCHB-X) RID, ORCID
Kraus, Tomáš (UOCHB-X) RID, ORCID
Hocek, Michal (UOCHB-X) RID, ORCIDSource Title Chemical Science . - : Royal Society of Chemistry - ISSN 2041-6520
Roč. 14, č. 15 (2023), s. 4059-4069Number of pages 11 s. Language eng - English Country GB - United Kingdom Keywords conjugated oligonucleotides ; DNA ; nucleotides OECD category Organic chemistry R&D Projects GX20-00885X GA ČR - Czech Science Foundation (CSF) Method of publishing Open access Institutional support UOCHB-X - RVO:61388963 UT WOS 000961816400001 EID SCOPUS 85152106327 DOI 10.1039/d2sc06718h Annotation We designed and synthesized a series of 2'-deoxyribonucleoside triphosphates (dNTPs) bearing various lipid moieties. Fatty acid- and cholesterol-modified dNTPs proved to be substrates for KOD XL DNA polymerase in primer extension reactions. They were also mutually compatible for simultaneous multiple incorporations into the DNA strand. The methodology of enzymatic synthesis opened a pathway to diverse structurally unique lipid-ON probes containing one or more lipid units. We studied interactions of such probes with the plasma membranes of live cells. Employing a rational design, we found a series of lipid-ONs with enhanced membrane anchoring efficiency. The in-membrane stability of multiply modified ONs was superior to that of commonly studied ON analogues, in which a single cholesterol molecule is typically tethered to the thread end. Notably, some of the probes were detected at the cell surface even after 24 h upon removal of the probe solution. Such an effect was general to several studied cell lines. 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 2024 Electronic address https://doi.org/10.1039/D2SC06718H
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