Unlocked Nucleic Acids with a Pyrene-Modified Uracil: Synthesis, Hybridization Studies, Fluorescent Properties and i-Motif Stability

0427579 - ÚOCHB 2015 RIV DE eng J - Článek v odborném periodiku
Perlíková, Pavla - Karlsen, K. K. - Pedersen, E. B. - Wengel, J.
Unlocked Nucleic Acids with a Pyrene-Modified Uracil: Synthesis, Hybridization Studies, Fluorescent Properties and i-Motif Stability.
Chembiochem. Roč. 15, č. 1 (2014), s. 146-156. ISSN 1439-4227. E-ISSN 1439-7633
Grant ostatní: European Research Council(XE) FP7-268776
Institucionální podpora: RVO:61388963
Klíčová slova: fluorescence * i-motifs * nucleic acid hybridization * oligonucleotides * unlocked nucleic acids
Kód oboru RIV: CE - Biochemie
Impakt faktor: 3.088, rok: 2014

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.
Trvalý link: http://hdl.handle.net/11104/0233146