Construction of a Lipid Droplets Targeted Fluorescent Probe for Visualization of Liver Tumor Cells

doi:10.6023/cjoc202309008

Abstract

Lipid droplets (LDs) are involved in the metabolic processes of many living cells, and their anomalies are highly associated with a variety of diseases, such as fatty liver, diabetes and cancers. But it is still a great challenge to elucidate the intrinsic relationship between various diseases and LDs. In particular, there has been only a few studies on the visualization of abnormal LDs in liver tumor cells. Therefore, in this paper, a lipid droplets targeted fluorescent probe was easily prepared through a two-step procedure by using triphenylamine as the electron donor and polycyanide heterocyclic compound as the electron acceptor. The fluorescent probe TCN-Tph possesses good ability to target LDs in living cells through their co- localization imaging experiments. In comparison with other carcinoma cells, the liver tumor cells have good response and uptake of TCN-Tph. The slices images of liver tissues in different states further show that the probe TCN-Tph can also distinguish liver tissues and normal liver tissues effectively, which provide an experimental basis for the early diagnosis of liver tumor cells in clinic.

Key words: lipid droplets, fluorescent probe, liver tumor cell, visualization

Cite this article

Dongqing Xu, Haishan Tong, Jie Shen, Wanwei Qiu, Lisheng Qian. Construction of a Lipid Droplets Targeted Fluorescent Probe for Visualization of Liver Tumor Cells[J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1240-1246.

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Fig. & Tab. 8

Scheme 1. Synthesis route of fluorescent probe TCN-Tph

Figure 1. (a) Normalization intensity of UV-Vis absorption and fluorescence spectra for TCN-Tph in PBS solution with the concentration of TCN-Tph at 5.0 μmol/L, and (b) fluorescence spectra of TCN-Tph in different mediums with the concentration of TCN-Tph at 5.0 μmol/L λex=440 nm and λem=560~850 nm. OA: oleic acid, CH: cholesterol, CE: cholesteryl ester, MAG: monoglycerol, DAG: diacylglycerol, TAG: Triacylglycerol, Hcys: homocysteine, GSH: glutathione, Cys: cystein.

Figure 2. Fluorescence spectra of probe TCN-Tph at 5.0 μmol/ L in different solvents λex=440 nm and λem= 650~760 nm.

Figure 3. Effect of fluorescent probe TCN-Tph on livability of living cells (a) HeLa, MAD-MB-231 and MCF-7; (b) Hep G2

Figure 4. Co-localization fluorescence images of 5.0 μmol/L TCN-Tph in liver tumor cell with LDs TCN-Tph: λex=405 nm and λem=700~800 nm. HCS Lipid TOXTM: λex=637 nm and λem=640~670 nm.

Figure 5. Co-localization fluorescence images of TCN-Tph at 5.0 μmol/L in different cells with LDs

Figure 6. Fluorescence intensities of TCN-Tph in different cells corresponding to the fluorescence images TCN-Tph: λex=405 nm and λem=700~800 nm

Figure 7. Fluorescence images of TCN-Tph at 3.0 μmol/L in normal liver, fat liver and liver tumor tissue TCN-Tph: λex=405 nm and λem=700~800 nm; HCS Lipid TOXTM: λex=637 nm and λem=640~670 nm; Hoechst 33342: λex=405 nm and λem=445~475 nm.

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