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Engineering the BASHY Dye Platform toward Architectures with Responsive Fluorescence.

João Felicidade¹, Fabio M F Santos¹, Jesús F Arteaga²

¹Research Institute for Medicines (iMed.ULisboa) Faculty of Pharmacy, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003, Lisbon, Portugal.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|March 27, 2023

Summary

This summary is machine-generated.

New boronic-acid-derived salicylidenehydrazone (BASHY) dyes exhibit tunable fluorescence. These compounds show pH-dependent emission, enabling applications in fluorescence lifetime imaging (FLIM) of live cells.

Keywords:

charge transfer electron transfer fluorescence fluorescence lifetime imaging organoboron dyes

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Area of Science:

Organic Chemistry
Supramolecular Chemistry
Materials Science

Background:

Salicylidenehydrazone derivatives are known fluorescent dyes.
Tuning electronic properties of dye backbones can modulate photophysical behavior.
Photoinduced electron transfer (PeT) is a mechanism for fluorescence quenching.

Purpose of the Study:

To synthesize and characterize novel boronic-acid-derived salicylidenehydrazone (BASHY) complexes.
To investigate the effect of electronic modifications on the BASHY dye platform.
To explore pH-dependent fluorescence switching and potential applications in bioimaging.

Main Methods:

Three-component reaction for BASHY complex synthesis.
Spectroscopic analysis (UV-Vis absorption, fluorescence emission).
Fluorescence lifetime measurements.
Cell imaging studies using fluorescence lifetime imaging microscopy (FLIM).

Main Results:

Nine BASHY complexes were synthesized in high yields.
Electronic modifications enabled fluorescence quenching via PeT in organic solvents.
OFF-ON fluorescence switching was achieved by acid addition.
In aqueous physiological conditions, BASHY dyes emitted in the red-to-NIR region (650-680 nm).
Dyes demonstrated appreciable quantum yields and lifetimes in water.
Successful application in FLIM of live A549 cells.

Conclusions:

BASHY dyes offer tunable fluorescence properties based on electronic structure and pH.
The pH-responsive fluorescence switching is suitable for biological applications.
BASHY dyes are promising probes for live-cell imaging using FLIM.