Selective<i>c-MYC</i>G4 DNA recognition based on a fluorescent light-up probe with disaggregation-induced emission characteristics

Wang, Ming-Qi; Li, Hong-Yao; Cao, Hao-Wen; Lang, Xue-Xian; Chen, Yansong

doi:10.1039/d2tb01316a

Cited by 8 publications

(4 citation statements)

References 40 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%

“…Among small-molecule fluorescent probes, cyanine dyes almost dominate the research field of photography and other relevant biosensing and disease theranostics, due to their favorable optical properties (e.g., high molar extinction coefficient and adjustable absorption and fluorescence spectra) as well as high biocompatibility. − However, conventional cyanine dyes exist as “always-on” fluorescent probes, which inevitably accumulate and are retained in non-target regions producing background signals, lowering the biological selectivity for bioimaging. In contrast, activatable probes can change fluorescence intensity or emission wavelength in response to specific physiological parameters, exhibiting higher signal-to-noise ratio and specificity, resulting in a lower detection limit compared to “always-on” fluorophores. − Therefore, designing activatable probes based on cyanine skeletons to selectively illuminate G-quadruplex structures is essential for improving detection sensitivity, especially for in vivo imaging with high complexity.…”

Section: Introductionmentioning

confidence: 99%

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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%

Section: Introductionmentioning

confidence: 99%

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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Discovery of Palbociclib as a potent c-Myc G4 stabilizer for lung cancer treatment using molecular docking, molecular dynamics simulation, and in vitro activity evaluation

Gao,

Liang,

Yin

et al. 2024

Mol Divers

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Selectivec-MYCG4 DNA recognition based on a fluorescent light-up probe with disaggregation-induced emission characteristics

Abstract: c-MYC promoter is well-known as an important oncogene, whose overexpression leads to ∼80% of all solid tumors. The four-stranded G4 present in the c-MYC promoter has been shown to play...

Cited by 8 publications

References 40 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

Discovery of Palbociclib as a potent c-Myc G4 stabilizer for lung cancer treatment using molecular docking, molecular dynamics simulation, and in vitro activity evaluation

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