Thionation toward High-Contrast ACQ-DIE Probes by Reprogramming the Aqueous Segregation Behavior: Enlightenment from a Sulfur-Substituted G-Quadruplex Ligand

Yao, Haojun; Liu, Song; Xing, Zhiming; Miao, Yun; Song, Zhibin; Li, Guorui; Huang, Jing

doi:10.1021/acs.analchem.2c02388

Cited by 9 publications

(3 citation statements)

References 45 publications

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“…Notably, the LOD of SN-Cy5-S was 1.51 nM, which was lower than for the previously reported DIE probes (Table ). ,,, A Job’s plot experiment demonstrated that SN-Cy5-S and G4s combined in ratios of 1:1 or 2:1 (Figure S15), consistent with the results of the above-described nonlinear fitting.…”

Section: Resultssupporting

confidence: 84%

ON–OFF Fluorescent Cyanine Dye Based on a Benzothiophenyl Rotor Enables Selective Illumination of G-Quadruplexes in Mitochondria

et al. 2023

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Conventional cyanine dyes exist as "always-on" fluorescent probes leading to inevitable background signals which often limit their performance and scope of applications. To develop specific fluorescent probes with high sensitivity and robust OFF/ON switching for targeting G4s, we introduced aromatic heterocycles through conjugation with polymethine chains to construct a rotor-π system. Here, a universal strategy is presented to synthesize pentamethine cyanines with different aromatic heterocycle substituents on the meso-polymethine chain. In these probes, SN-Cy5-S is self-quenched in aqueous solution due to H-aggregation. The structure indicates that SN-Cy5-S with a flexible meso-benzothiophenyl rotor conjugated to the cyanine backbone matches adaptively with G-tetrad planes, enhancing π−π stacking and resulting in triggered fluorescence. This allows recognition of G-quadruplexes due to the synergy of disaggregation-induced emission (DIE) and inhibited twisted intramolecular charge-transfer effects. This combination leads to a robust lighting-up fluorescence response for c-myc G4 with superior fluorescence enhancement (98-fold), allowing for a low detection limit of 1.51 nM, which is much more sensitive than the previously reported DIE-based G4 probes (22−83.5 nM). In addition, the superior imaging properties and rapid internalization time (5 min) in mitochondria allow SN-Cy5-S to also have a high potential for mitochondrially targeting anti-cancer therapy.

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Section: Resultssupporting

confidence: 84%

ON–OFF Fluorescent Cyanine Dye Based on a Benzothiophenyl Rotor Enables Selective Illumination of G-Quadruplexes in Mitochondria

et al. 2023

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“…The development of luminescent materials coupled with the rapid evolution of optical microscopy techniques has allowed generation of valuable knowledge in the roles and functions that G4s play in cells. ,, However, in many conventional systems, fluorophores experience the phenomenon of aggregation-induced quenching (ACQ) that limits their full potential as diagnostic agents . Recently, we − and others − have introduced a selective G4 recognition strategy that relies on the disassembly of self-aggregated dyes, namely, disaggregation-induced emission (DIE). Dyes operating through DIE display remarkable topological/sequence selectivity − ,− for G4s and have broad applicability in cellular systems. ,, …”

mentioning

confidence: 99%

“…Recently, we − and others − have introduced a selective G4 recognition strategy that relies on the disassembly of self-aggregated dyes, namely, disaggregation-induced emission (DIE). Dyes operating through DIE display remarkable topological/sequence selectivity − ,− for G4s and have broad applicability in cellular systems. ,, …”

mentioning

confidence: 99%

Parallel G-Quadruplex DNA Structures from Nuclear and Mitochondrial Genomes Trigger Emission Enhancement in a Nonfluorescent Nano-aggregated Fluorine–Boron-Based Dye

Deiana

Chand

Chorell

et al. 2023

J. Phys. Chem. Lett.

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Molecular self-assembly is a powerful tool for the development of functional nanostructures with adaptive optical properties. However, in aqueous solution, the hydrophobic effects in the monomeric units often afford supramolecular architectures with typical side-by-side π-stacking arrangement with compromised emissive properties. Here, we report on the role of parallel DNA guanine quadruplexes (G4s) as supramolecular disaggregating−capture systems capable of coordinating a zwitterionic fluorine−boron-based dye and promoting activation of its fluorescence signal. The dye's high binding affinity for parallel G4s compared to nonparallel topologies leads to a selective disassembly of the dye's supramolecular state upon contact with parallel G4s. This results in a strong and selective disaggregation-induced emission that signals the presence of parallel G4s observable by the naked eye and inside cells. The molecular recognition strategy reported here will be useful for a multitude of affinity-based applications with potential in sensing and imaging systems.

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Fluorescence Enhancement of Adamantane‐Modified Dyes in Aqueous Solution via Supramolecular Interaction with Methyl‐β‐cyclodextrin and Their Application in Cell Imaging

Liu,

Zhang,

et al. 2023

Chemistry A European J

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The fluorescence of functional dyes was generally quenched in aqueous solution, which hindered their application in water‐bearing detections. In this work, a novel strategy based on host‐guest interaction was provided for the purpose of fluorescence enhancement in aqueous solution and cell imaging. Three adamantane‐modified fluorescent dyes (Coum‐Ad, NP‐Ad, NR‐Ad) with coumarin, 1,8‐naphthalimide and Nile Red as fluorophores were initially designed and prepared. The ((adamantan‐1‐yl)methyl)amino group, as the auxochrome of those dyes, complexed with methylated β‐cyclodextrin (M‐β‐CD) via supramolecular interaction, and then fluorescent supramolecular nanoparticles (FSNPs) were formed by self‐assembly in water. The inclusion equilibrium constant (K) could be as high as 3.94×104 M−1. With the addition of M‐β‐CD, fluorescence quantum yields of these dyes were separately improved to 69.8 %, 32.9 % and 41.3 %. Inspired by the above satisfactory results, six adamantane‐modified probes organelle‐NPAds with organelle‐targeting capability were further obtained. As the formation of hydrogen bonds between organelle‐NPAd2 and M‐β‐CD verified by theoretical calculation, K of organelle‐NPAd2 (5.13×104 M−1~4.53×105 M−1) with M‐β‐CD was higher than that of organelle‐NPAd1 (1.15×104 M−1~3.66×104 M−1) and their fluorescence quantum yields increased to 32.8 %~83.6 % in aqueous solution. In addition, fluorescence enhancement was realized in cell imaging with the addition of M‐β‐CD.

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Thionation toward High-Contrast ACQ-DIE Probes by Reprogramming the Aqueous Segregation Behavior: Enlightenment from a Sulfur-Substituted G-Quadruplex Ligand

Cited by 9 publications

References 45 publications

ON–OFF Fluorescent Cyanine Dye Based on a Benzothiophenyl Rotor Enables Selective Illumination of G-Quadruplexes in Mitochondria

ON–OFF Fluorescent Cyanine Dye Based on a Benzothiophenyl Rotor Enables Selective Illumination of G-Quadruplexes in Mitochondria

Parallel G-Quadruplex DNA Structures from Nuclear and Mitochondrial Genomes Trigger Emission Enhancement in a Nonfluorescent Nano-aggregated Fluorine–Boron-Based Dye

Fluorescence Enhancement of Adamantane‐Modified Dyes in Aqueous Solution via Supramolecular Interaction with Methyl‐β‐cyclodextrin and Their Application in Cell Imaging

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