An Aggregating Amphiphilic Squaraine: A Light-up Probe That Discriminates Parallel G-Quadruplexes

Angewandte Chemie
Vincenzo GrandeFrank Würthner

Abstract

G-quadruplexes (G4s) are peculiar DNA or RNA tertiary structures that are involved in the regulation of many biological events within mammalian cells, bacteria, and viruses. Although their role as versatile therapeutic targets has been emphasized for 35 years, G4 selectivity over ubiquitous double-stranded DNA/RNA, as well as G4 differentiation by small molecules, still remains challenging. Here, a new amphiphilic dicyanovinyl-substituted squaraine, SQgl, is reported to act as an NIR fluorescent light-up probe discriminating an extensive panel of parallel G4s while it is non-fluorescent in the aggregated state. The squaraine can form an unconventional sandwich π-complex binding two quadruplexes, which leads to a strongly fluorescent (ΦF =0.61) supramolecular architecture. SQgl is highly selective against non-quadruplex and non-parallel G4 sequences without altering their topology, as desired for applications in selective in vivo high-resolution imaging and theranostics.

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Citations

Feb 24, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tong CheShuo-Bin Chen
Mar 6, 2018·Chemistry : a European Journal·Bing LiuXiufeng Zhang
Aug 22, 2017·Organic & Biomolecular Chemistry·Claire BeauvineauFlorence Mahuteau-Betzer
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Dec 15, 2018·Chemistry : a European Journal·Maximilian H SchreckChristoph Lambert
Feb 11, 2021·Chemistry : a European Journal·Pichandi AshokkumarAndrey S Klymchenko
Apr 20, 2021·Chemistry : a European Journal·Arthur TurkinChristoph Lambert
Nov 18, 2017·The Journal of Physical Chemistry Letters·Marco DeianaKatarzyna Matczyszyn
Aug 1, 2019·Bioconjugate Chemistry·Kristina IlinaMaged Henary

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