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Aggregation-induced lipid droplet targeted staining reagent based on purine skeleton, preparation method and application thereof

An aggregation-inducing and dyeing reagent technology, applied in the field of biochemistry, can solve the problems of small Stokes shift and poor photostability, and achieve the effects of low biological toxicity, high selectivity and multiple selectivity

Active Publication Date: 2020-07-10
SICHUAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In order to solve the problems of small Stokes shift and poor photostability of existing lipid droplet dyes, the purpose of the present invention is to provide an aggregation-inducible lipid droplet targeting staining reagent based on a purine skeleton and its preparation method and application

Method used

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  • Aggregation-induced lipid droplet targeted staining reagent based on purine skeleton, preparation method and application thereof
  • Aggregation-induced lipid droplet targeted staining reagent based on purine skeleton, preparation method and application thereof
  • Aggregation-induced lipid droplet targeted staining reagent based on purine skeleton, preparation method and application thereof

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preparation example Construction

[0074] The preparation method of the aggregation-inducible lipid droplet targeted staining reagent based on the purine skeleton of the present invention comprises the following steps:

[0075] (1) 2,6-dichloropurine and R 1 Halide R 1 -X is dissolved in an organic solvent, and after adding a weak base, heat and stir at 50-120°C for 4-12 hours to obtain the first intermediate; wherein, X is Cl, Br or I; the organic solvent is at least one of DMSO and DM The weak base is at least one of sodium carbonate, potassium carbonate, potassium phosphate and sodium phosphate;

[0076] (2) Mix and stir the second intermediate, weak base and organic solvent for 1-2 hours, then add R 2 replaced Heat and stir at 50-100°C for 4-12 hours to obtain the second intermediate; the organic solvent is at least one of dioxane and tetrahydrofuran, and the weak base is n-butyllithium, potassium tert-butoxide, sodium tert-butoxide, At least one of potassium hydride, sodium hydride, potassium carbonat...

Embodiment 1

[0079] The preparation method of the purine skeleton-based aggregation-inducible cell membrane targeting staining reagent of this embodiment comprises the following steps:

[0080] (1) Synthetic intermediate 1: 2,6-dichloro-9-n-propyl-9-hydro-purine (compound 1):

[0081]

[0082] 2,6-Dichloropurine (1.0 mmol), 1-bromopropane (1.5 mol) and potassium carbonate (3.0 mmol) were mixed and stirred in DMSO (5 mL) for 6 hours, then 100 mL of water was added. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (30 mL×3). The organic extracts were washed with brine and treated with Na 2 SO 4 dry. After the solvent was removed and distilled under reduced pressure, it was purified by 200-300 mesh silica gel column chromatography. Elution with petroleum ether / ethyl acetate (3:2) gave compound 1 as a white solid with a yield of 57%. The eluent is ethyl acetate / petroleum ether=2:3 (V / V). Finally, a white solid was obtained with a yield of 61%, an...

Embodiment 2

[0095] 6-(2,3-Diphenyl-1H-indol-1-yl)-9-propyl-2-(4-(trifluoromethyl)phenyl)-9H-purine (compound 4)

[0096] This embodiment is basically the same as embodiment 1, the difference is that the compound Middle R 3 The substituent, its synthetic route is as follows:

[0097]

[0098] Under nitrogen protection, compound 2 (509mg, 1.1mmol), 4-trifluoromethylphenylboronic acid (1.5eq), tetrakistriphenylphosphopalladium (0.05eq) and 2.0mL sodium carbonate aqueous solution (2M) were added to 10.0mL In dioxane, reflux for 8 hours, and after the completion of the reaction as monitored by thin-layer chromatography, the reaction mixture was poured into 100 mL of water and extracted with dichloromethane. The organic layer was washed with brine, water, and Na 2 SO 4 dry. After the solvent was removed and distilled under reduced pressure, it was purified by 200-300 mesh silica gel column chromatography. Eluted with dichloromethane, compound 4 was obtained as a white solid with a yie...

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Abstract

The invention discloses an aggregation-induced lipid droplet targeted staining reagent based on a purine skeleton, a preparation method and application thereof, and belongs to the technical field of biochemistry. The aggregation-induced lipid droplet targeted staining reagent based on a purine skeleton has ultra-large and adjustable Stokes shift, adjustable emission wavelength, low biotoxicity, good light stability and aggregation-induced emission characteristics; high-sensitivity, high-selectivity and in-situ imaging of lipid droplets are achieved by combining the aggregation-induced lipid droplet targeted staining reagent with a fluorescence sensing technology, meanwhile, the reagent is concise in synthetic route and mild in reaction conditions and has economical and easily available rawmaterials, therefore a new thought and a new method are provided for design of a lipid droplet targeted staining fluorescent probe.

Description

technical field [0001] The invention relates to the technical field of biochemistry, in particular to an aggregation-inducible lipid droplet targeting staining reagent based on a purine skeleton and a preparation method and application thereof. Background technique [0002] Lipid droplets, which are rich in neutral lipids such as triglycerides and sterol esters, are the main place for storing energy in cells. In addition, the internal sterols, fatty acids and phosphates also provide the basis for the formation of intracellular biofilms. Therefore, the diverse functions of lipid droplets make it play an important role in membrane biology and energy metabolism, and also make lipid droplets an important organelle to maintain the balance of cell development. However, precisely because of its ability to store lipids, pathological studies in recent years have found that the accumulation of lipid droplets is closely related to diseases such as obesity, diabetes, and atherosclerosi...

Claims

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Application Information

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IPC IPC(8): C07D473/00C09K11/06G01N21/64
CPCC07D473/00C09K11/06C09K2211/1011C09K2211/1029C09K2211/1074G01N21/64G01N21/6402G01N21/6428G01N21/6458G01N2021/6417G01N2021/6439
Inventor 李坤石磊于抗抗刘艳红余孝其
Owner SICHUAN UNIV
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