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Thiophene-linked tetramethylbodipy-labeled nucleotide for viscosity-sensitive oligonucleotide probes of hybridization and protein-DNA interactions
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SYSNO ASEP 0522408 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Thiophene-linked tetramethylbodipy-labeled nucleotide for viscosity-sensitive oligonucleotide probes of hybridization and protein-DNA interactions Author(s) Güixens-Gallardo, Pedro (UOCHB-X) RID, ORCID
Humpolíčková, Jana (UOCHB-X) ORCID
Miclea, Sebastian Paul (UOCHB-X) ORCID
Pohl, Radek (UOCHB-X) RID, ORCID
Kraus, Tomáš (UOCHB-X) RID, ORCID
Jurkiewicz, Piotr (UFCH-W) RID, ORCID
Hof, Martin (UFCH-W) RID, ORCID
Hocek, Michal (UOCHB-X) RID, ORCIDSource Title Organic & Biomolecular Chemistry. - : Royal Society of Chemistry - ISSN 1477-0520
Roč. 18, č. 5 (2020), s. 912-919Number of pages 8 s. Language eng - English Country GB - United Kingdom Keywords polymerase synthesis ; molecular rotors ; fluorescent probes Subject RIV CC - Organic Chemistry OECD category Organic chemistry Subject RIV - cooperation J. Heyrovsky Institute of Physical Chemistry - Physical ; Theoretical Chemistry R&D Projects GA17-14791S GA ČR - Czech Science Foundation (CSF) EF16_019/0000729 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) GX19-26854X GA ČR - Czech Science Foundation (CSF) Method of publishing Limited access Institutional support UOCHB-X - RVO:61388963 ; UFCH-W - RVO:61388955 UT WOS 000512061200013 EID SCOPUS 85079020660 DOI 10.1039/c9ob02634g Annotation Cytosine 2′-deoxyribonucleoside dCTBdp and its triphosphate (dCTBdpTP) bearing tetramethylated thiophene-bodipy fluorophore attached at position 5 were designed and synthesized. The green fluorescent nucleoside dCTBdp showed a perfect dependence of fluorescence lifetime on the viscosity. The modified triphosphate dCTBdpTP was substrate to several DNA polymerases and was used for in vitro enzymatic synthesis of labeled oligonucleotides (ONs) or DNA by primer extension. The labeled single-stranded ONs showed a significant decrease in mean fluorescence lifetime when hybridized to the complementary strand of DNA or RNA and were also sensitive to mismatches. The labeled dsDNA sensed protein binding (p53), which resulted in the increase of its fluorescence lifetime. The triphosphate dCTBdpTP was transported to live cells where its interactions could be detected by FLIM but it did not show incorporation to genomic DNA in cellulo. 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 2021 Electronic address https://pubs.rsc.org/en/content/articlelanding/2020/OB/C9OB02634G#!divAbstract
Number of the records: 1