Irkutsk Scientific Center of Surgery and Traumatology, 664003 Irkutsk, Russia.
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Science, 664033 Irkutsk, Russia.
Molecules. 2022 Aug 7;27(15):5018. doi: 10.3390/molecules27155018.
A bright far-red emitting unsymmetrical -CF-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 ≈ 610-620 nm and emission at λ ≈ 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.
一种具有苯基和吡唑基取代基的亮远红色发射不对称-CF-BODIPY 荧光染料，通过三氟吡咯乙醇与吡唑基吡咯缩合合成，随后对形成的二吡咯甲烷进行氧化和络合。该 BODIPY 染料在 λ ≈ 610-620nm 处具有光吸收，在 λ ≈ 640-650nm 处具有发射。该 BODIPY 作为溶酶体特异性荧光染料在艾氏腹水癌细胞上进行了研究，允许对细胞结构进行活体染色，并随后实时监测细胞中发生的变化。还表明，细胞的摄取率、细胞内进入溶酶体的运输率以及细胞对染料的饱和率取决于其在培养基中的浓度。选择 5μM 的浓度作为最适合活细胞溶酶体荧光染色的 BODIPY 浓度，而 100μM 的浓度被发现对艾氏腹水癌细胞有毒。
