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Cell lipid droplet fluorescence imaging probe with efficient red/near-infrared emission based on bithienobenzene derivative and application of cell lipid droplet fluorescence imaging probe

A benzene derivative and double thieno technology, applied in the field of cell lipid droplet fluorescence imaging probes, can solve the problems of crosstalk, lipid droplet staining specificity and photostability, excitation laser and fluorescence detection, etc., and achieve high photostability , the effect of super dyeing selectivity, high dyeing selectivity

Active Publication Date: 2022-07-22
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, BODIPY 493 / 503 showed a slight Stokes shift, which could lead to crosstalk between the excitation laser and fluorescence detection
Nile red has a significant Stokes shift, but its specificity and photostability of lipid droplet staining are not very good

Method used

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  • Cell lipid droplet fluorescence imaging probe with efficient red/near-infrared emission based on bithienobenzene derivative and application of cell lipid droplet fluorescence imaging probe
  • Cell lipid droplet fluorescence imaging probe with efficient red/near-infrared emission based on bithienobenzene derivative and application of cell lipid droplet fluorescence imaging probe
  • Cell lipid droplet fluorescence imaging probe with efficient red/near-infrared emission based on bithienobenzene derivative and application of cell lipid droplet fluorescence imaging probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] 1. Synthesis of compound 2

[0023] Benzodithiophene 1 (4.49 g, 20.0 mmol), zinc dust (2.73 g, 42 mmol) and sodium hydroxide (12.0 g, 30.0 mmol) were refluxed in water (100 mL) for 2 h. Then, 1-bromo-2-methoxyethane (8.34 g, 60.0 mmol) and a catalytic amount of tetrabutylammonium bromide were added to the reaction system. After refluxing for 12 h, the reaction mixture was poured into water, and CH 2 Cl 2 multiple extractions. Combined organic layers in anhydrous MgSO 4 It was dried on top and filtered through a suction filter bottle. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography to obtain 3.00 g (8.86 mmol, 44%) of compound 2 as a white solid.

[0024] 1 H NMR (400MHz, CDCl 3 ): δ7.55(d,J=5.5Hz,2H),7.37(d,J=5.5Hz,2H),4.41(t,4H),3.77(t,4H),3.49(s,6H).

[0025] 2. Synthesis of compound 3

[0026] Cooled with an ice-water bath, bromine (1.42 g, 8.86 mmol) and CH 2 Cl 2 (10 mL) of the mixture was sl...

Embodiment 2

[0034] Example 2: Determination of Absorption-Emission Spectrum of Cell Lipid Droplet Fluorescence Imaging Probe LDs-Red Prepared in Example 1

[0035] The cellular lipid droplet fluorescence imaging probe LDs-Red synthesized in Example 1 was prepared into a solution with a concentration of 10 μM with 10 mL of toluene solvent. Scan the absorption spectrum with an ultraviolet-visible spectrophotometer in the wavelength range of 300-700 nm to obtain the absorption spectrum, and collect the fluorescence emission spectrum with a fiber-optic fluorescence spectrometer under the excitation of 470 nm, and use the Origin software to process the data to obtain the following figure 1 The absorption-emission spectrum of the cell lipid droplet fluorescence imaging probe LDs-Red in toluene solution (the left dashed line is the absorption spectrum, the right solid line is the emission spectrum), illustrating the cell lipid droplet fluorescence imaging probe The absorption-emission peak posit...

Embodiment 3

[0036] Example 3: Culture of HeLa cells

[0037] All percentages in this example are volume fractions.

[0038] HeLa cells were grown at 37°C, CO 2 The cells were cultured in a 5% concentration incubator, and the culture medium was high-glucose DMEM containing 10% fetal bovine serum and 1% double antibody (penicillin-streptomycin mixture). Among them, fetal bovine serum, double antibody and high glucose DMEM were directly purchased from biological reagent companies.

[0039] When the cells grow to the logarithmic phase, we pass the cells: remove the original 5mL culture medium in the cell culture flask, wash the surface of the cells with 2mL DMEM medium without fetal bovine serum, and remove the culture medium. The cells were then digested with 0.5 mL of trypsin for 2 minutes. After most of the cells were detached, 2 mL of high-glucose DMEM medium containing 10% fetal bovine serum and 1% double antibody was added, pipetting evenly, and an appropriate amount of the cell dispe...

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Abstract

The invention relates to a bithienobenzene derivative-based cell lipid droplet fluorescence imaging probe with efficient red / near-infrared emission and application thereof, and belongs to the technical field of biological fluorescence imaging, and the structural formula of the fluorescence probe is shown in the specification. The invention also discloses application of the fluorescent probe in specific labeling of lipid droplets in HeLa cells and visualization of the form and distribution of the lipid droplets in the HeLa cells. Experiments prove that the fluorescent probe LDs-Red disclosed by the invention is a lipid droplet fluorescent probe with the advantages of efficient red / near-infrared emission, ultrahigh lipid droplet dyeing selectivity, light stability and the like, and has a huge application prospect.

Description

technical field [0001] The invention belongs to the technical field of biological fluorescence imaging, and in particular relates to a cell lipid droplet fluorescence imaging probe with high-efficiency red / near-infrared emission based on bis-thienoacene derivatives and its use in specifically labeling lipid droplets in cells and visualizing cells in cells Applications in lipid droplet morphology and distribution. Background technique [0002] Lipid droplets are ubiquitous organelles in almost all eukaryotic cells, and they consist of a neutral lipid core and a surrounding phospholipid monolayer. LDLs are produced by division from the endoplasmic reticulum into the cytoplasm, where they mature and expand by merging with other LDLs or synthesizing more neutral lipids. For a long time, lipid droplets were grossly underestimated, and their role was simply thought to store excess lipids in cells. However, recent studies have shown that lipid droplets play critical roles in a va...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04C09K11/06G01N21/64
CPCC07D495/04C09K11/06G01N21/6428C09K2211/1007C09K2211/1092
Inventor 卢革宇王晨光彭桂杉闫旭刘方猛孙鹏刘晓敏
Owner JILIN UNIV
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