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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

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Indole-Boron-Difluoride Complexes with Anticancer and Fluorescence Properties.

Veerapattha Vanthiya¹, Theeranuch Jaroenchuensiri², Kriangsak Faikhruea³

¹Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Special Research Unit for Advanced Magnetic Resonance (AMR), Kasetsart University, Bangkok, 10900, Thailand.

Chemistry, an Asian Journal

|March 15, 2025

Summary

New indole-boron-difluoride complexes show tunable photophysical properties influenced by solvent polarity. One derivative demonstrated significant anticancer activity and fluorescence imaging potential for biomedical applications.

Keywords:

Borondifluoride Cancer Cell imaging Fluorescent probes Indole

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Area of Science:

Organic Chemistry
Materials Science
Photophysics

Background:

Indole derivatives are crucial in medicinal chemistry and materials science.
Boron-difluoride complexes offer unique photophysical properties.
Understanding structure-property relationships is key for developing new functional materials.

Purpose of the Study:

Synthesize novel indole-boron-difluoride complexes.
Investigate their photophysical properties and response to environmental factors.
Evaluate their potential for biomedical applications, including anticancer activity and fluorescence imaging.

Main Methods:

Sonogashira coupling and Larock heteroannulation for complex synthesis.
Spectroscopic analysis (UV-Vis absorption, fluorescence emission) to determine photophysical properties.
Correlation of properties with Hammett constants and Lippert-Mataga parameters.
Time-Dependent Density Functional Theory (TD-DFT) calculations.

Main Results:

Eight indole-boron-difluoride complexes were successfully synthesized.
Distinct photophysical properties were observed, sensitive to solvent polarity.
Aggregation-induced emission (AIE) was noted in mixed solvents.
Strong correlations between spectral properties, electronic effects (Hammett constants), and intramolecular charge transfer (ICT) were established.
A methyl ester-substituted complex showed potent anticancer activity against HeLa cells and fluorescence imaging capabilities.

Conclusions:

The synthesized indole-boron-difluoride complexes possess tunable photophysical characteristics.
Electronic and solvent effects significantly modulate their spectral behavior and ICT characteristics.
The methyl ester derivative holds promise for dual applications in cancer therapy and fluorescence-based cell imaging.