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pH fluorescent probes: chlorinated fluoresceins.

Feng-Yan Ge1, Li-Gong Chen

  • 1College of Chemistry and Chemical Engineering, Donghua University, Shanghai, People's Republic of China. fyge@dhu.edu.cn

Journal of Fluorescence
|December 25, 2007
PubMed
Summary

New chlorinated fluoresceins offer enhanced fluorescence and pH sensitivity. These compounds show promise as advanced fluorescent probes for measuring pH in acidic cellular environments.

Area of Science:

  • Organic Chemistry
  • Photophysics
  • Biomedical Probes

Background:

  • Fluorescein is a widely used fluorescent dye, but its properties can be limiting for certain applications.
  • Developing new fluorescent probes with improved photophysical properties and pH sensitivity is crucial for biological research.

Purpose of the Study:

  • To synthesize and characterize novel regiospecific chlorinated fluoresceins.
  • To investigate the photophysical and pH-dependent properties of these new compounds.
  • To evaluate their potential as fluorescent probes for cellular pH measurements.

Main Methods:

  • Regiospecific synthesis involving chlorinated resorcinols and phthalic anhydride.
  • Chromatographic separation of regioisomers.
  • Spectroscopic analysis of photophysical properties (absorption, emission, quantum yield).

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  • Detailed study of pH-dependent behavior and pKa determination.

    • Main Results:

    • Successful synthesis and separation of chlorinated fluorescein regioisomers.
    • Obtained compounds exhibit long-wavelength absorption/emission and high fluorescence quantum yields.
    • Demonstrated strong pH sensitivity within the 3.5-7.0 range.
    • Exhibited lower pKa values compared to standard fluorescein.
    • Maximum fluorescent intensity observed in the physiological pH range (6.8-7.4).

    Conclusions:

    • Chlorinated fluoresceins possess superior photophysical properties and pH sensitivity.
    • Their lower pKa values and high quantum yields make them ideal for pH sensing.
    • These novel probes are well-suited for accurate pH measurements in acidic cellular environments.