Application of meso-CF3-Fluorophore BODIPY with Phenyl and Pyrazolyl Substituents for Lifetime Visualization of Lysosomes

Irina S Trukhan; Denis N Tomilin; Nataliya N Dremina; Lyubov N Sobenina; Michael G Shurygin; Konstantin B Petrushenko; Igor K Petrushenko; Boris A Trofimov; Irina A Shurygina

doi:10.3390/molecules27155018

Application of meso-CF₃-Fluorophore BODIPY with Phenyl and Pyrazolyl Substituents for Lifetime Visualization of Lysosomes

Molecules. 2022 Aug 7;27(15):5018. doi: 10.3390/molecules27155018.

Authors

Irina S Trukhan¹, Denis N Tomilin², Nataliya N Dremina¹, Lyubov N Sobenina², Michael G Shurygin¹, Konstantin B Petrushenko², Igor K Petrushenko³, Boris A Trofimov², Irina A Shurygina¹

Affiliations

¹ Irkutsk Scientific Center of Surgery and Traumatology, 664003 Irkutsk, Russia.
² A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Science, 664033 Irkutsk, Russia.
³ Irkutsk National Research Technical University, 664074 Irkutsk, Russia.

Abstract

A bright far-red emitting unsymmetrical meso-CF₃-BODIPY fluorescent dye with phenyl and pyrazolyl substituents was synthesized by condensation of trifluoropyrrolylethanol with pyrazolyl-pyrrole, with subsequent oxidation and complexation of the formed dipyrromethane. This BODIPY dye exhibits optical absorption at λ_ab ≈ 610-620 nm and emission at λ_em ≈ 640-650 nm. The BODIPY was studied on Ehrlich carcinoma cells as a lysosome-specific fluorescent dye that allows intravital staining of cell structures with subsequent real-time monitoring of changes occurring in the cells. It was also shown that the rate of uptake by cells, the rate of intracellular transport into lysosomes, and the rate of saturation of cells with the dye depend on its concentration in the culture medium. A concentration of 5 μM was chosen as the most suitable BODIPY concentration for fluorescent staining of living cell lysosomes, while a concentration of 100 μM was found to be toxic to Ehrlich carcinoma cells.

Keywords: BODIPY; BioStation CT; Ehrlich ascites carcinoma; fluorescent sensor; lysosome.

MeSH terms

Boron Compounds / chemistry
Carcinoma*
Fluorescent Dyes* / chemistry
Humans
Ionophores
Lysosomes / chemistry

Substances

4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
Boron Compounds
Fluorescent Dyes
Ionophores

Grants and funding

The synthesis of BODIPY and analysis of its spectroscopic and photophysical properties were carried out with the financial support of the Russian Foundation for Basic Research, grant 19-53-53008 GFEN_a).