An Aggregating Amphiphilic Squaraine: A Light-up Probe That Discriminates Parallel G-Quadruplexes |
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Authors: | Dr. Vincenzo Grande Dr. Filippo Doria Prof. Dr. Mauro Freccero Prof. Dr. Frank Würthner |
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Affiliation: | 1. Universität Würzburg, Institut für Organische Chemie & Center for Nanosystems Chemistry & Bavarian Polymer Institute (BPI), Am Hubland, 97074 Würzburg, Germany;2. Università di Pavia, Dipartimento di Chimica, Viale Taramelli 10, 27100 Pavia, Italy |
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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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Keywords: | amphiphilic aggregation fluorescent probes G-quadruplexes molecular recognition squaraine |
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