New repertoire of 'donor-two-acceptor' NIR fluorogenic dyes

Area of Science:

• Organic Chemistry
• Biomedical Imaging
• Materials Science

Background:

• Fluorescent dyes are essential for diagnostic and optical imaging.
• There is a continuous need for novel fluorogenic dyes with enhanced properties.
• Existing dyes often have limitations in wavelength and functionality.

Purpose of the Study:

• To develop a new strategy for designing long-wavelength fluorescent dyes with a turn-ON capability.
• To synthesize and characterize novel fluorogenic dyes based on a donor-two-acceptor π-electron system.
• To evaluate the potential of these dyes for biological imaging applications.

Main Methods:

• Design of a donor-two-acceptor π-electron system for internal charge transfer.
• Synthesis of novel fluorogenic dyes utilizing naphthol and hydroxycoumarin as latent donors.
• Characterization of fluorescent properties, including emission wavelengths and quantum yields.
• In vitro and in vivo testing for biological imaging, specifically targeting mitochondria.

Main Results:

• A series of novel long-wavelength fluorescent dyes were successfully synthesized.
• One synthesized dye exhibited excellent near-infrared (NIR) fluorescent characteristics.
• This NIR dye was validated as a specific mitochondrial imaging reagent in live cells.
• The donor-two-acceptor strategy proved effective for creating new fluorochromes with extended π-conjugation.

Conclusions:

• The developed strategy enables the rational design of novel long-wavelength and turn-ON fluorogenic dyes.
• The synthesized NIR fluorescent dye shows significant potential for advanced biological and cellular imaging.
• This approach opens new avenues for the discovery of innovative near-infrared fluorescence probes.