Issue 3, 2021

Synthesis and application of a 19F-labeled fluorescent nucleoside as a dual-mode probe for i-motif DNAs

Abstract

Because of their stable orientations and their minimal interference with native DNA interactions and folding, emissive isomorphic nucleoside analogues are versatile tools for the accurate analysis of DNA structural heterogeneity. Here, we report on a bifunctional trifluoromethylphenylpyrrolocytidine derivative (FPdC) that displays an unprecedented quantum yield and highly sensitive 19F NMR signal. This is the first report of a cytosine-based dual-purpose probe for both fluorescence and 19F NMR spectroscopic DNA analysis. FPdC and FPdC-containing DNA were synthesized and characterized; our robust dual probe was successfully used to investigate the noncanonical DNA structure, i-motifs, through changes in fluorescence intensity and 19F chemical shift in response to i-motif formation. The utility of FPdC was exemplified through reversible fluorescence switching of an FPdC-containing i-motif oligonucleotide in the presence of Ag(I) and cysteine.

Graphical abstract: Synthesis and application of a 19F-labeled fluorescent nucleoside as a dual-mode probe for i-motif DNAs

Supplementary files

Article information

Article type
Paper
Submitted
30 jan 2021
Accepted
04 mar 2021
First published
10 mar 2021
This article is Open Access
Creative Commons BY-NC license

RSC Chem. Biol., 2021,2, 876-882

Synthesis and application of a 19F-labeled fluorescent nucleoside as a dual-mode probe for i-motif DNAs

W. A. Wee, J. H. Yum, S. Hirashima, H. Sugiyama and S. Park, RSC Chem. Biol., 2021, 2, 876 DOI: 10.1039/D1CB00020A

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