Red-emitting fluorogenic BODIPY-tetrazine probes for biological imaging

Area of Science:

• Organic Chemistry
• Photochemistry
• Biophysical Chemistry

Background:

• Development of novel fluorescent probes is crucial for advanced bioimaging.
• BODIPY and tetrazine scaffolds are widely used in developing functional dyes.
• Intramolecular charge transfer (ICT) states, particularly twist ICT (TICT), influence photophysical properties.

Purpose of the Study:

• To synthesize and characterize novel BODIPY-tetrazine derivatives.
• To investigate the photophysical properties, including TICT state formation in polar solvents.
• To evaluate the potential of the lead compound for bioimaging applications.

Main Methods:

• Synthesis of BODIPY-tetrazine derivatives.
• Spectroscopic analysis (absorption, emission, lifetime) in various solvents.
• Cellular imaging studies using click chemistry in mammalian and cancer cells.

Main Results:

• A series of BODIPY-tetrazine derivatives were successfully synthesized.
• Derivative 6i demonstrated a stable TICT state in polar solvents and strong red-emission.
• Compound 6i effectively imaged lipids and sugars in live cells under no-wash conditions.

Conclusions:

• The developed BODIPY-tetrazine derivatives are promising fluorescent probes.
• Derivative 6i exhibits excellent photophysical properties and biocompatibility for live-cell imaging.
• This work expands the toolkit for advanced cellular imaging using novel fluorescent dyes.