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A kind of 3,5-dimorpholinyl-8-p-methylphenyl fluorine boron derivatives and its preparation method and application

A technology of methylphenyl fluoroboron and methylphenyl fluoroboron, which is applied in the field of fluoroboron derivatives, can solve the problems of complex structure, high price and inconvenient synthesis of endoplasmic reticulum targeting reagents, and is easy to achieve A large number of acquisitions, low prices, and low cost effects

Active Publication Date: 2020-07-24
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-dimorpholinyl-8-p-methylphenyl fluorine boron derivatives and its preparation method and application
  • A kind of 3,5-dimorpholinyl-8-p-methylphenyl fluorine boron derivatives and its preparation method and application
  • A kind of 3,5-dimorpholinyl-8-p-methylphenyl fluorine boron derivatives and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

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

[0051] Add 8-p-methylphenylfluoroborate (28.2 mg, 0.10 mmol), morpholine (34.8 μL, 0.40 mmol), AgOAc (66.8 mg, 4.0 equiv), dimethyl sulfoxide (1.0 mL) into 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-dimorpholino was obtained as a black solid -8.1 mg of 8-p-methylphenylfluoroboron, yield 18%.

[0054] ...

Embodiment 2

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

[0058] The compound 3,5-dimorpholino-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-dimorpholino-8-p-methylphenylfluoroborofluorene, 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 that the maximum absorption peak of the absorption spectrum of the compound 3,5-dimorpholino-8-p-methylphenylfluoroboron is located at 570nm; the maximum absorption peak of the fluores...

Embodiment 3

[0061] The compound 3,5-dimorpholino-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-dimorpholinyl-8-p-methylphenylfluoroborin 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 image of the compound 3,5-dimorpholinyl-8-p-methylphenylfluoroboron (excitation wavelength: 553nm, emission ...

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Abstract

The invention provides 3,5-dimorpholino-8-p-methyl phenyl fluoroboron fluorophore derivatives, and belongs to the technical field of fluoroboron fluorophore derivatives. The fluoroboron fluorophore derivatives have a structure which is as shown in the formula I: the formula I is shown in the description. The invention also provides a preparation method of the fluoroboron fluorophore derivatives. Asynthetic route used in the preparation method is that C-H / N-H is directly oxidized and subjected to a coupled reaction; compared with a conventional fluoroboron fluorophore ammoniation preparation technology, organic synthesizing steps are shortened; a cumbersome process of pre-activating a substrate is avoided; the compatibility of a reaction is improved; the total yield of a synthesizing reaction is increased. When the fluoroboron fluorophore derivatives provided by the invention are applied to endoplasmic reticulum specific fluorescence development and fluorescence labelling, the cost isfar lower than that of a commercially available cell endoplasmic labelling reagent; the problems that an endoplasmic target reagent in the prior art is complicated in structure and high in cost, and has inconvenience in synthesis can be solved.

Description

technical field [0001] The invention belongs to the technical field of fluoborofluores derivatives, and specifically relates to a 3,5-dimorpholino-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, Tr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06A61K49/00
CPCA61K49/0021C07F5/022C09K11/06C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1055
Inventor 吴迪章华星兰静波高戈杨宇东杨修光梁文博
Owner SICHUAN UNIV
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