Jump to main content
Jump to site search

Issue 35, 2019
Previous Article Next Article

Fine structural tuning of styryl-based dyes for fluorescence and CD-based sensing of various ds-DNA/RNA sequences

Author affiliations

Abstract

A set of styryl- and bis-styryl dyes, varying in length, aromatic surface, net positive charge and steric positioning or bulkiness of substituents, was tested for interactions with various ds-DNA or ds-RNA. Most of the compounds showed strong affinity toward ds-DNA/RNA, directly correlated to the synergistic contribution of the aromatic-conjugated surface and net positive charge. The volume or positioning of terminal aromatic substituents directly controlled the binding mode of the core structure, shifting between DNA/RNA groove binding or DNA/RNA intercalation. Consequently, upon binding to DNA/RNA the fluorimetric and induced CD (ICD) response varied for different compounds, for instance one derivative showed specific fluorescence increase with AT-DNA, while another derivative showed specific ICD response with AU-RNA. Preliminary screening on human tumour cell lines revealed an efficient cellular uptake for all dyes. Only mono-styryl-quinoline derivatives showed a strong antiproliferative activity combined with efficient fluorescent localisation, thus showing promising theragnostic potential, while other compounds were negligibly cytotoxic but still efficient fluorescent markers of cytoplasmic organelles.

Graphical abstract: Fine structural tuning of styryl-based dyes for fluorescence and CD-based sensing of various ds-DNA/RNA sequences

Back to tab navigation

Supplementary files

Article information


Submitted
21 May 2019
Accepted
15 Aug 2019
First published
19 Aug 2019

Org. Biomol. Chem., 2019,17, 8243-8258
Article type
Paper

Fine structural tuning of styryl-based dyes for fluorescence and CD-based sensing of various ds-DNA/RNA sequences

V. Botti, A. Cesaretti, Ž. Ban, I. Crnolatac, G. Consiglio, F. Elisei and I. Piantanida, Org. Biomol. Chem., 2019, 17, 8243
DOI: 10.1039/C9OB01186B

Social activity

Search articles by author

Spotlight

Advertisements