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

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.

XPS and quantum chemical analysis of 4Me-BODIPY derivatives

“…2 Due to the ease of structural modification based on BODIPY derivatives, it is possible to obtain luminophores that absorb and emit in almost the entire spectral range. 3 Such a set of practically significant physicochemical properties allows the use of dyes in this class in various fields, including molecular sensorics, 4,5 medical diagnostics, [6][7][8] biochemistry, [9][10][11][12] etc.…”