Fluorogenic Squaraine Dendrimers for Background‐Free Imaging of Integrin Receptors in Cancer Cells

Ashokkumar, Pichandi; Collot, Mayeul; Klymchenko, Andrey S.

doi:10.1002/chem.202100480

Cited by 3 publications

(1 citation statement)

References 78 publications

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“…Among the neutral red-emitting fluorophores, squaraine benefits form sharp spectra and huge extinction coefficients (up to 300,000 M –1 ·cm –1 ), hence conferring a high brightness. , These appealing properties led us to develop an efficient PM probe based on indolenine squaraine . Although indolenine-based squaraines have proven their efficiency in several bioimaging applications as far-red-emitting probes, ,,, pyrrolyl squaraine, known for several decades, has essentially been applied to organic photovoltaics and has not been explored as a potential probe for bioimaging. Moreover, to our knowledge, only one example of a squaraine-based molecular rotor was given in the literature where a clickable benzothiazolium squaraine dye exhibited a limited fluorescence enhancement of ∼2-fold from 2/8 to 9/1 glycerol/methanol mixture …”

Section: Introductionmentioning

confidence: 99%

Red-Emitting Pyrrolyl Squaraine Molecular Rotor Reports Variations of Plasma Membrane and Vesicular Viscosity in Fluorescence Lifetime Imaging

Pfister,

Lesieur,

Bourdoncle

et al. 2024

Anal. Chem.

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The viscosity that ensures the controlled diffusion of biomolecules in cells is a crucial biophysical parameter. Consequently, fluorescent probes capable of reporting viscosity variations are valuable tools in bioimaging. In this field, red-shifted probes are essential, as the widely used and gold standard probe remains green-emitting molecular rotors based on BODIPY. Here, we demonstrate that pyrrolyl squaraines, red-emissive fluorophores, exhibit high sensitivity over a wide viscosity range from 30 to 4890 mPa•s. Upon alkylation of the pyrrole moieties, the probes improve their sensitivity to viscosity through an enhanced twisted intramolecular charge transfer phenomenon. We utilized this scaffold to develop a plasma membrane probe, pSQ-PM, that efficiently stains the plasma membrane in a fluorogenic manner. Using fluorescence lifetime imaging, pSQ-PM enabled efficient sensing of viscosity variations in the plasma membrane under various conditions and in different cell lines (HeLa, U2OS, and NIH/ 3T3). Moreover, upon incubation, pSQ-PM stained the membrane of intracellular vesicles and suggested that the lysosomal membranes displayed enhanced fluidity.

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Section: Introductionmentioning

confidence: 99%

Red-Emitting Pyrrolyl Squaraine Molecular Rotor Reports Variations of Plasma Membrane and Vesicular Viscosity in Fluorescence Lifetime Imaging

Pfister,

Lesieur,

Bourdoncle

et al. 2024

Anal. Chem.

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Highly Efficient Aggregation‐Induced Chiral TADF Molecules Exhibiting Prolonged Lifetime in Living Cells under Hypoxic Stress

Ye,

Zheng,

Ali

et al. 2024

Advanced Optical Materials

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Thermally activated delayed fluorescence (TADF) materials have garnered significant attention as potential candidates for biological photoluminescence imaging. However, the achievement of tunable chiral TADF materials through aggregated and self‐assembled processes remains a formidable challenge. In this study, four donor–acceptor–donor type chiral TADF molecules, designed by directly linking electron‐donating moieties (phenoxazine, phenothiazine or 1‐phenyl‐1,2,3,4‐tetrahydroisoquinoline) with an electron‐acceptor unit (diphenyl sulfone), as promising candidates for luminescent imaging applications are presented. The experimental investigation reveals that these chiral TADF materials possess remarkably small ΔEST values, promoting efficient reverse intersystem crossing (RISC). Additionally, they exhibit aggregation‐induced emission and long‐delayed luminescent lifetimes affected by the aggregated and self‐assembled state. Moreover, deoxygenation significantly enhances the emission, enabling high‐contrast hypoxia probing, which shows great potential for high‐contrast photoluminescence imaging in living cells. This work not only offers a molecular design strategy for chiral TADF materials but also extends the diverse biological applications of high‐contrast hypoxia detection in the biological field.

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Advancements in molecular disassembly of optical probes: a paradigm shift in sensing, bioimaging, and therapeutics

Saczuk,

Dudek,

Matczyszyn

et al. 2024

Nanoscale Horiz.

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Fluorogenic Squaraine Dendrimers for Background‐Free Imaging of Integrin Receptors in Cancer Cells

Cited by 3 publications

References 78 publications

Red-Emitting Pyrrolyl Squaraine Molecular Rotor Reports Variations of Plasma Membrane and Vesicular Viscosity in Fluorescence Lifetime Imaging

Red-Emitting Pyrrolyl Squaraine Molecular Rotor Reports Variations of Plasma Membrane and Vesicular Viscosity in Fluorescence Lifetime Imaging

Highly Efficient Aggregation‐Induced Chiral TADF Molecules Exhibiting Prolonged Lifetime in Living Cells under Hypoxic Stress

Advancements in molecular disassembly of optical probes: a paradigm shift in sensing, bioimaging, and therapeutics

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