Carboxyl-BODIPY based fluorescent biomarkers: Spectral characteristics, photostability and possibilities for practical application

• Published in: Journal of photochemistry and photobiology. A, Chemistry. Chemistry., 2023-10, Vol.444, p.114926, Article 114926
• Main Authors: Guseva, Galina B., Lukanov, Michail M., Ksenofontov, Alexander A., Antina, Elena V., Lisovskaya, Svetlana, Nikitina, Liliya E., Galembikova, Aigul R., Boichuk, Sergey V.
• Format: Article
• Language: English
• Subjects: Carboxyl-BODIPYs; Fluorescent biomarker; Photostability; Spectral properties
• ISSN: 1010-6030
• DOI: 10.1016/j.jphotochem.2023.114926

[Display omitted] •The spectral properties of α- and meso-carboxyl-BODIPYs are compared.•Carboxyl-BODIPYs are stable over a wide pH range and intensely fluoresce.•Meso-substitution of carboxyl-BODIPYs increases the photostability and lipophilicity of the dyes.•The carboxylic acid BODIPYs are not cytotoxic activity.•Carboxyl-BODIPYs are promising probes for bioimaging of pathogens causing mycotic. A comparative analysis of the structural and solvation factors on the spectral properties, pH stability, photostability, and lipophilicity of BODIPY luminophores containing carboxylic acid residues in α- and meso-position was carried out. The interaction of these BODIPYs with cells of microscopic fungi (Candida albicans and Fusarium solani) was studied. The compounds were found to be stable across a wide range of pH values and exhibited intense fluorescence (to φ ∼ 94%) at 508–587 nm. The introduction of a carboxylic acid residue into the meso-position of the BODIPY core causes a noticeable increase (almost ∼2 times) of the Stokes shift compared to the meso-unsubstituted analogues. On the other hand, α-carboxyl-BODIPYs showed a red shift in both the absorption and fluorescence bands. Effective fluorescence quenching (up to 40–80%) was observed in electron donor solvents for carboxyl-BODIPYs, especially for the carboxylic acid BODIPY with a thiophene substituent. The presence of a carboxyl group in the α-position of the BODIPY increased its affinity to hydrophilic media by approximately ∼1.2–2 times compared to meso-carboxyl-BODIPYs. Given the lack of cytotoxicity, carboxyl-BODIPYs may be recommended as effective biomarkers for examining the differences between a wide range of pathogens causing mycotic.