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A kind of 3,5-dibenzimidazolyl-8-p-methylphenylfluoroborofluorine derivatives and its preparation method and application

A technology of methyl phenyl fluoride boron fluoride and methyl phenyl fluoride boron fluoride is applied in the field of fluorine boron fluoride derivatives, which can solve the problems of high price, inconvenient synthesis, complex structure of endoplasmic reticulum targeting reagents, etc. Inexpensive, increase overall yield, shorten the effect of organic synthesis steps

Active Publication Date: 2020-09-25
SICHUAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is to provide a small molecule of fluorine-boron derivatives that can be used for endoplasmic reticulum labeling. Using the fluorine-boron derivatives of the present invention for fluorescent labeling of endoplasmic reticulum can effectively solve the internal problems in the prior art. Plasma reticulum targeting reagents are complex in structure, inconvenient to synthesize, and expensive

Method used

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  • A kind of 3,5-dibenzimidazolyl-8-p-methylphenylfluoroborofluorine derivatives and its preparation method and application
  • A kind of 3,5-dibenzimidazolyl-8-p-methylphenylfluoroborofluorine derivatives and its preparation method and application
  • A kind of 3,5-dibenzimidazolyl-8-p-methylphenylfluoroborofluorine derivatives and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0050] Synthesis of 3,5-Dibenzimidazolyl-8-p-methylphenylfluoroborofluorene

[0051] 8-p-methylphenylfluoroborin (14.1mg, 0.05mmol), benzimidazole (23.6mg, 0.20mmol), AgOAc (33.4mg, 4.0equiv), dimethyl sulfoxide (1.0mL) were added to the reaction tube, stirred evenly under nitrogen, heated to 80°C, and reacted for 12 hours; the specific reaction formula is as follows:

[0052]

[0053] After the reaction is complete, cool the reaction tube to room temperature, remove the solvent and add 10 mL of dichloromethane to dissolve the reaction system, then filter through diatomaceous earth and wash with 10-20 mL of dichloromethane, combine the filtrates, remove the solvent under reduced pressure, The residue was separated and purified by silica gel column chromatography (dichloromethane / petroleum ether / ethyl acetate=10:10:1, v / v / v), and after vacuum drying, the target product 3,5-dibenzimidazole was obtained as a black solid 21.3mg of 8-p-methylphenylfluoroborofluorene, yield 83%....

Embodiment 2

[0057] The ultraviolet-visible-near-infrared absorption spectrum and fluorescence emission spectrum of the compound 3,5-dibenzimidazolyl-8-p-methylphenylfluoroboron prepared in Example 1

[0058] The compound 3,5-dibenzimidazolyl-8-p-methylphenylfluoroboron was dissolved in dichloromethane to form 1×10 - 5 mol / L, take 2.5mL and put it into a cuvette, and measure the UV-visible-near-infrared absorption and fluorescence emission spectra.

[0059] Figure 4 It is the ultraviolet-visible light absorption spectrum and fluorescence emission spectrum of the compound 3,5-dibenzimidazolyl-8-p-methylphenylfluoroborate, wherein the black solid line represents the ultraviolet-visible light absorption spectrum, and the black dotted line represents the fluorescence emission spectrum. From Figure 4 It can be seen from the figure that the maximum absorption peak of the absorption spectrum of the compound 3,5-dibenzimidazolyl-8-p-methylphenylfluoroboron is located at 546nm; the maximum abs...

Embodiment 3

[0061] The compound 3,5-dibenzimidazolyl-8-p-methylphenylfluoroborate prepared in Example 1 and the commercially available endoplasmic reticulum stain ER-Tracker TM Fluorescence confocal confocal imaging of Green in HepG2 cells

[0062] First, add 5% CO to the DMEM(H) medium containing 10% fetal bovine serum 2 , HepG2 cells were cultured at 37°C for 24 hours. The medium was removed, and 2.5 μM of the compound 3,5-dibenzimidazolyl-8-p-methylphenylfluoroborate in phosphate buffer was added, followed by 1 μM of the commercially available endoplasmic reticulum stain ER-Tracker TM Green was co-incubated at 37°C for 30 minutes. After the culture is over, take out the culture glass-bottom dish, wash it with phosphate buffer saline for 2 to 3 times, and image the culture glass-bottom dish through a fluorescent confocal microscope.

[0063] Figure 5 It is the fluorescence imaging diagram of the compound 3,5-dibenzimidazolyl-8-p-methylphenylfluoroborate (excitation wavelength: 55...

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Abstract

The invention provides a 3, 5-dibenzimidazolyl-8-p-methylphenyl boron dipyrromethene derivative and belongs to the technical field of boron dipyrromethene derivatives. The boron dipyrromethene derivative has the structure shown in the formula I. The invention also provides a preparation method of the boron dipyrromethene derivative. The synthetic route used in the preparation method is a C-H / N-H direct oxidative coupling reaction. Compared with the traditional boron dipyrromethene ammoniation preparation method, the method reduces the organic synthesis steps, is free of the complicated processof pre-activation of the substrate, improves the compatibility of the reaction and increases the overall yield of the synthesis reaction. The application of the boron dipyrromethene derivative in cellular endoplasmic reticulum specific fluorescence development and fluorescent labeling reduces the cost than the commercially available cellular endoplasmic reticulum labeling reagent, and can solve the problem that the existing endoplasmic reticulum targeting reagent has a complicated structure, is inconvenient in synthesis and has an expensive price.

Description

technical field [0001] The invention belongs to the technical field of fluoborofluores derivatives, and specifically relates to a 3,5-dibenzimidazolyl-8-p-methylphenylfluoroborofluores derivatives and a preparation method and application thereof. Background technique [0002] The endoplasmic reticulum is a very important multifunctional organelle in eukaryotic cells. The synthesis, folding and modification of intracellular proteins, the synthesis of lipids and sterols take place in the endoplasmic reticulum. While completing these basic physiological functions, the endoplasmic reticulum has become a hub platform for coordinating signal transduction by virtue of its huge membrane structure, maintaining the stability of the intracellular environment. When genetic or environmental damage causes endoplasmic reticulum stress, excessive endoplasmic reticulum stress or prolonged endoplasmic reticulum stress can cause apoptosis, which can lead to a series of diseases [see: J.E.Vance...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06C09K2211/1044G01N21/6486
Inventor 吴迪章华星游劲松兰静波杨宇东杨修光梁文博
Owner SICHUAN UNIV
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