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

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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

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Publication details

The article was received on 29 Jun 2018, accepted on 26 Aug 2018 and first published on 14 Sep 2018


Article type: Edge Article
DOI: 10.1039/C8SC02882F
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY license
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    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, Advance Article , DOI: 10.1039/C8SC02882F

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