1. Exploring the impact of meso-position fluorination on BODIPYs : Synthesis, electrochemical Insights, and potential therapeutic applications in breast cancer
- Author
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Carmo, C., Almeida, J. M. S., Araújo, J., Brett, C. M. A., Botelho, M. F., Cordova, Armando, Laranjo, M., Sobral, A. J. F. N., Carmo, C., Almeida, J. M. S., Araújo, J., Brett, C. M. A., Botelho, M. F., Cordova, Armando, Laranjo, M., and Sobral, A. J. F. N.
- Abstract
Three boron dipyrromethane molecules (BODIPYs) were synthesized in this study with different quantities of fluorine in the meso position. The samples were characterized by NMR spectroscopy, absorption, mass spectrometry, and cyclic voltammetry, which was utilized to electrochemically measure the energy gaps between the HOMO (highest-energy occupied molecular orbital) and LUMO (lowest-energy unoccupied molecular orbital). The MTT and SRB assays were used to assess the viability of these dyes in breast cancer cells (MCF-7 and HCC-1806) and African green monkey kidney cells (Vero). The newly synthesized BODIPY tris(perfluorophenoxy)phenyl (1) compound has exhibited remarkable stability and lacks photocytotoxicity in this investigation, thus rendering it a promising candidate for application in bioimaging. At defined concentrations, the BODIPYs bearing perfluorophenyl (2) and hydroxyphenyl (3) moieties have been identified as prospective candidates for photosensitization in photodynamic therapy for breast cancer. Their notable phototoxic properties upon irradiation and the absence of significant metabolic activity reduction in normal VERO cells after 24 h of exposure suggest their potential efficacy in this therapeutic approach.
- Published
- 2024
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