Issue 44, 2018

Selective parallel G-quadruplex recognition by a NIR-to-NIR two-photon squaraine

Abstract

Fluorescence imaging probes for specific G-quadruplex (G4) conformations are of considerable interest in biomedical research. Herein, we present the synthesis and the binding properties of a new water-soluble near-infrared (NIR) amphiphilic squaraine dye (CAS-C1) which is capable of selective detection of parallel over non-parallel and non G4 topologies. The striking changes in its linear optical response upon binding to parallel G4s give rise to high fluorescence quantum yields (Φf ≈ 0.7) and one-photon molecular brightness in the far-red-NIR region. The outstanding recognition process of CAS-C1 for parallel G4s via end-stacking provides binding constants in the nanomolar regime (Kb = 107 to 108 M−1) awarding it as one of the most potent parallel G4 binders currently available. Moreover, the CAS-C1-parallel G4 system exhibits large two-photon absorption (TPA) cross-sections and molecular brightness in the second NIR biological transparency window (λ ≈ 1275 nm), making it an ideal candidate for NIR-to-NIR ultrasensitive two-photon procedures.

Graphical abstract: Selective parallel G-quadruplex recognition by a NIR-to-NIR two-photon squaraine

Supplementary files

Article information

Article type
Edge Article
Submitted
29 Jun 2018
Accepted
26 Aug 2018
First published
14 Sep 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 8375-8381

Selective parallel G-quadruplex recognition by a NIR-to-NIR two-photon squaraine

V. Grande, C. Shen, M. Deiana, M. Dudek, J. Olesiak-Banska, K. Matczyszyn and F. Würthner, Chem. Sci., 2018, 9, 8375 DOI: 10.1039/C8SC02882F

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements