Journal
CHEMBIOCHEM
Volume 17, Issue 16, Pages 1558-1562Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cbic.201600182
Keywords
double-stranded RNA; fluorogenic nucleobase; peptide nucleic acids; triple helices
Funding
- US National Science Foundation [CHE-1406433, CHE-0922815]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1406433] Funding Source: National Science Foundation
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Development of new fluorescent peptide nucleic acids (PNAs) is important for fundamental research and practical applications. The goal of this study was the design of fluorogenic nucleobases for incorporation in triplex-forming PNAs. The underlying design principle was the use of a protonation event that accompanied binding of a 2-aminopyridine (M) nucleobase to a G-C base pair as an on switch for a fluorescence signal. Two fluorogenic nucleobases, 3-(1-phenylethynyl)-M and phenylpyrrolo-M, were designed, synthesized and studied. The new M derivatives provided modest enhancement of fluorescence upon protonation but showed reduced RNA binding affinity and quenching of fluorescence signal upon triple-helix formation with cognate double-stranded RNA. Our study illustrates the principal challenges of design and provides guidelines for future improvement of fluorogenic PNA nucleobases. The 3-(1-phenylethynyl)-M may be used as a fluorescent nucleobase to study PNA-RNA triple-helix formation.
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