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Article

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

by
Irina S. Trukhan
1,
Denis N. Tomilin
2,
Nataliya N. Dremina
1,
Lyubov N. Sobenina
2,
Michael G. Shurygin
1,
Konstantin B. Petrushenko
2,
Igor K. Petrushenko
3,
Boris A. Trofimov
2,* and
Irina A. Shurygina
1,*
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
*
Authors to whom correspondence should be addressed.
Molecules 2022, 27(15), 5018; https://doi.org/10.3390/molecules27155018
Submission received: 6 July 2022 / Revised: 26 July 2022 / Accepted: 4 August 2022 / Published: 7 August 2022
(This article belongs to the Special Issue Design, Synthesis and Biological Activity of Nitrogen-Containing Heterocyclic Compounds)
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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 λab ≈ 610–620 nm and emission at λem ≈ 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; fluorescent sensor; Ehrlich ascites carcinoma; lysosome; BioStation CT BODIPY; fluorescent sensor; Ehrlich ascites carcinoma; lysosome; BioStation CT

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MDPI and ACS Style

Trukhan, I.S.; Tomilin, D.N.; Dremina, N.N.; Sobenina, L.N.; Shurygin, M.G.; Petrushenko, K.B.; Petrushenko, I.K.; Trofimov, B.A.; Shurygina, I.A. Application of meso-CF3-Fluorophore BODIPY with Phenyl and Pyrazolyl Substituents for Lifetime Visualization of Lysosomes. Molecules 2022, 27, 5018. https://doi.org/10.3390/molecules27155018

AMA Style

Trukhan IS, Tomilin DN, Dremina NN, Sobenina LN, Shurygin MG, Petrushenko KB, Petrushenko IK, Trofimov BA, Shurygina IA. Application of meso-CF3-Fluorophore BODIPY with Phenyl and Pyrazolyl Substituents for Lifetime Visualization of Lysosomes. Molecules. 2022; 27(15):5018. https://doi.org/10.3390/molecules27155018

Chicago/Turabian Style

Trukhan, Irina S., Denis N. Tomilin, Nataliya N. Dremina, Lyubov N. Sobenina, Michael G. Shurygin, Konstantin B. Petrushenko, Igor K. Petrushenko, Boris A. Trofimov, and Irina A. Shurygina. 2022. "Application of meso-CF3-Fluorophore BODIPY with Phenyl and Pyrazolyl Substituents for Lifetime Visualization of Lysosomes" Molecules 27, no. 15: 5018. https://doi.org/10.3390/molecules27155018

APA Style

Trukhan, I. S., Tomilin, D. N., Dremina, N. N., Sobenina, L. N., Shurygin, M. G., Petrushenko, K. B., Petrushenko, I. K., Trofimov, B. A., & Shurygina, I. A. (2022). Application of meso-CF3-Fluorophore BODIPY with Phenyl and Pyrazolyl Substituents for Lifetime Visualization of Lysosomes. Molecules, 27(15), 5018. https://doi.org/10.3390/molecules27155018

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