A General Strategy Toward Highly Fluorogenic Bioprobes Emitting across the Visible Spectrum

Area of Science:

• Organic chemistry
• Biochemistry
• Fluorescence imaging

Background:

• Developing highly fluorogenic probes is crucial for advanced biological sensing and imaging.
• Boron dipyrromethene (BODIPY) dyes are versatile fluorophores but require strategies for enhanced fluorescence.
• Existing methods for creating fluorogenic probes can be limited in scope and applicability.

Purpose of the Study:

• To develop a general and facile strategy for creating highly fluorogenic BODIPY-based probes.
• To establish a new fluorogenic mechanism applicable across the visible spectrum.
• To demonstrate the utility of these probes for detecting various biomolecules and enzymes.

Main Methods:

• Introduced a novel fluorogenic mechanism in BODIPY dyes by modulating the electron-withdrawing capabilities of meso-substituents.
• Synthesized a panel of BODIPY derivatives with emission maxima from green to far-red (509, 585, 660 nm).
• Incorporated specific triggering motifs to create bioprobes for hydrogen peroxide (H2O2), hydrogen sulfide (H2S), and proteases.

Main Results:

• Demonstrated a stimuli-triggered reduction in electron-withdrawing capabilities, leading to dramatic fluorescence enhancement.
• Successfully applied the strategy to various BODIPY structures emitting across the visible spectrum.
• Developed a mitochondria-targeting far-red probe for imaging endogenous H2O2 in living cells.

Conclusions:

• The presented strategy offers a general approach for engineering highly fluorogenic BODIPY bioprobes.
• This method enables the creation of diverse probes for sensing and imaging various analytes.
• The developed probes show significant potential for applications in cellular imaging and diagnostics.