A multiple acetal chalcone-BODIPY-based fluorescence: synthesis, physical property, and biological studies

Area of Science:

• Organic Chemistry
• Materials Science
• Biotechnology

Background:

• Fluorescent probes are crucial for functional dye design, but aldehyde group instability is a challenge.
• Existing fluorescent probes often lack stability in specific functional groups, limiting their applications.
• Developing probes with enhanced stability and controlled reactivity is essential for advanced imaging and diagnostics.

Purpose of the Study:

• To design and synthesize novel BODIPY-based fluorescent probes incorporating chalcone and acetal functionalities.
• To enhance the stability of fluorescent probes by introducing ethoxy groups for controlled aldehyde conversion.
• To evaluate the physical and biological properties of the novel chalcone-BODIPY fluorophores for potential drug delivery applications.

Main Methods:

• Synthesis of two novel BODIPY fluorophores using a mild strategy based on a specific ligand and chalcone derivative.
• Characterization of the fluorophores' emission wavelengths (around 530 nm) and fluorescence intensity.
• Biological evaluation using MTT assays for cytotoxicity and flow cytometry for apoptosis analysis, alongside in vitro and in vivo imaging.

Main Results:

• Successful synthesis of two chalcone-BODIPY fluorophores with emission around 530 nm and high fluorescence intensity.
• MTT assays revealed IC50 values for BODIPY 5 and BODIPY 6 in the range of 63–86 μM across tested cell lines.
• Flow cytometry indicated comparable apoptosis rates to reference agents, and BODIPY 6 demonstrated excellent biocompatibility and cell imaging potential in live cell and in vivo studies.

Conclusions:

• A mild synthesis strategy for novel BODIPY fluorophores with enhanced stability via acetal groups was established.
• The synthesized chalcone-BODIPY dyes exhibit promising photophysical properties and significant biological compatibility.
• These novel fluorescent probes show potential for development into drug functional fluorescent dyes and advanced bioimaging applications.