Analyte-Induced Restriction of Intramolecular Rotation: Turn-On aza-BODIPY Sensor for Biothiol Detection in Aqueous...

Area of Science:

• Organic Chemistry
• Analytical Chemistry
• Biochemistry

Background:

• Biothiols are crucial biological molecules involved in various cellular processes.
• Accurate detection of biothiols is essential for understanding disease mechanisms and developing diagnostics.
• Existing fluorescent probes often rely on analyte-triggered cleavage, which can have limitations.

Purpose of the Study:

• To synthesize and evaluate novel aza-BODIPY fluorophores for biothiol sensing.
• To introduce and validate an unconventional "turn-on" fluorescence sensing mechanism.
• To establish a new platform for developing sensitive and selective fluorescent probes.

Main Methods:

• Synthesis of two alternate aza-BODIPY fluorophores with a formyl-functional group.
• Evaluation of the synthesized fluorophores for biothiol sensing capabilities.
• Investigation of the fluorescence response mechanism upon analyte interaction.

Main Results:

• The synthesized aza-BODIPY fluorophores demonstrated high binding constants (up to 9800 M⁻¹).
• Low limits of detection were achieved, as low as 1 μM for biothiols.
• An unconventional "turn-on" sensing mechanism, based on analyte-induced restriction of intramolecular rotation, was successfully demonstrated.

Conclusions:

• The developed aza-BODIPY fluorophores are effective tools for biothiol sensing.
• The novel "turn-on" mechanism offers an alternative to traditional cleavage-based sensing strategies.
• This work presents a promising foundation for next-generation fluorescent probes in biosensing applications.