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Unlocked Nucleic Acids with a Pyrene-Modified Uracil: Synthesis, Hybridization Studies, Fluorescent Properties and i-Motif Stability
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SYSNO ASEP 0427579 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Unlocked Nucleic Acids with a Pyrene-Modified Uracil: Synthesis, Hybridization Studies, Fluorescent Properties and i-Motif Stability Author(s) Perlíková, Pavla (UOCHB-X) RID, ORCID
Karlsen, K. K. (DK)
Pedersen, E. B. (DK)
Wengel, J. (DK)Number of authors 4 Source Title Chembiochem. - : Wiley - ISSN 1439-4227
Roč. 15, č. 1 (2014), s. 146-156Number of pages 11 s. Language eng - English Country DE - Germany Keywords fluorescence ; i-motifs ; nucleic acid hybridization ; oligonucleotides ; unlocked nucleic acids Subject RIV CE - Biochemistry Institutional support UOCHB-X - RVO:61388963 UT WOS 000328682000018 EID SCOPUS 84890674031 DOI 10.1002/cbic.201300567 Annotation The synthesis of two new phosphoramidite building blocks for the incorporation of 5-(pyren-1-yl)uracilyl unlocked nucleic acid (UNA) monomers into oligonucleotides has been developed. Monomers containing a pyrene-modified nucleobase component were found to destabilize an i-motif structure at pH 5.2, both under molecular crowding and noncrowding conditions. The presence of the pyrene-modified UNA monomers in DNA strands led to decreases in the thermal stabilities of DNA*/DNA and DNA*/RNA duplexes, but these duplexes' thermal stabilities were better than those of duplexes containing unmodified UNA monomers. Pyrene-modified UNA monomers incorporated in bulges were able to stabilize DNA*/DNA duplexes due to intercalation of the pyrene moiety into the duplexes. Steady-state fluorescence emission studies of oligonucleotides containing pyrene-modified UNA monomers revealed decreases in fluorescence intensities upon hybridization to DNA or RNA. Efficient quenching of fluorescence of pyrene-modified UNA monomers was observed after formation of i-motif structures at pH 5.2. The stabilizing/destabilizing effect of pyrene-modified nucleic acids might be useful for designing antisense oligonucleotides and hybridization probes. 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 2015
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