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BODIPY Fluorophores for Membrane Potential Imaging.

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    Area of Science:

    • Organic Chemistry
    • Biophysical Chemistry
    • Materials Science

    Background:

    • BODIPY dyes are valuable fluorophores due to their tunable properties and biological compatibility.
    • Enhancing the water-solubility of BODIPY dyes is crucial for biological applications but presents synthetic challenges.
    • Existing methods for water-solubilization can interfere with the electronic properties needed for functional indicators.

    Purpose of the Study:

    • To develop a general strategy for creating water-soluble BODIPY dyes.
    • To synthesize novel BODIPY-based voltage-sensitive fluorophores (VF) for cellular imaging.
    • To evaluate the performance of these new dyes in biological systems.

    Main Methods:

    • Synthesized five new BODIPYs with sulfonated aromatic groups at the meso position.
    • Functionalized these water-soluble BODIPYs to create thirteen novel BODIPY-based voltage-sensitive fluorophores (VF).
    • Tested the voltage sensitivity and brightness of the new VF dyes in mammalian cells and neurons.

    Main Results:

    • Demonstrated that a sulfonated aromatic group at the meso position is an effective strategy for water-soluble BODIPYs.
    • Developed 13 new BODIPY-based voltage-sensitive fluorophores.
    • Achieved high voltage sensitivity (48% ΔF/F per 100 mV) in mammalian cells with the most sensitive dye.
    • Showcased the ability of these dyes to report on action potential dynamics in neurons and cardiomyocytes.

    Conclusions:

    • The strategy of incorporating a sulfonated aromatic group provides a versatile route to water-soluble BODIPY fluorophores.
    • The developed BODIPY VFs offer a promising tool for studying cellular electrophysiology with improved brightness and sensitivity.
    • This work expands the toolkit for designing functional fluorescent indicators with tunable electronic properties.