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Photoluminescence offers a wide range of applications due to its inherent sensitivity and selectivity. This technique allows for both direct and indirect analyses of the analyte. Direct quantitative analysis is possible when the analyte exhibits a favorable quantum yield for fluorescence or phosphorescence. However, an indirect analysis may be feasible if the analyte is not fluorescent or phosphorescent, or if the quantum yield is unfavorable. Indirect methods include reacting the analyte with...
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Phosphonofluoresceins: Synthesis, Spectroscopy, and Applications.

Joshua L Turnbull, Brittany R Benlian, Ryan P Golden

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    Researchers developed novel 3-phosphonofluoresceins, enhancing water solubility and cellular brightness for improved intracellular imaging. These new fluorophores also enable advanced membrane potential sensing applications.

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    Area of Science:

    • Organic Chemistry
    • Biochemistry
    • Materials Science

    Background:

    • Xanthene fluorophores, such as fluorescein, are widely used in chemistry and life sciences.
    • 3-carboxyfluorescein and 3-sulfonofluorescein have been mainstays for 150 years.
    • 3-phosphonofluorescein has not been previously reported.

    Purpose of the Study:

    • To synthesize and characterize 3-phosphonofluoresceins.
    • To explore their spectroscopic properties and potential applications.
    • To develop new voltage-sensitive dyes for cellular imaging.

    Main Methods:

    • Synthesis of 3-phosphonofluoresceins and their esters.
    • Spectroscopic characterization (absorption, emission).
    • Cellular uptake, retention, and brightness measurements.
    • Development of phosphono-voltage sensitive fluorophores (phosVF2.1.Cl).

    Main Results:

    • 3-Phosphonofluoresceins exhibit enhanced water solubility and pH stability compared to 3-carboxyfluorescein.
    • Esterification allows cellular entry, yielding significantly improved cellular brightness (>70-fold).
    • The free acid form is suitable for membrane potential sensing, with phosVF2.1.Cl showing high voltage sensitivity (26% ΔF/F per 100 mV).

    Conclusions:

    • The first synthesis of 3-phosphonofluoresceins is reported.
    • This new class of xanthene dyes offers improved properties for intracellular imaging.
    • 3-Phosphonofluoresceins are valuable tools for membrane potential sensing and cellular research.