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3, 5-dibenzimidazolyl-8-thiophenyl fluoroboron fluorescent derivatives as well as preparation method and application thereof

A thienyl fluoroboron and benzimidazole-based technology, which is applied in the field of fluoroborin derivatives, can solve the problems of complex structure, inconvenient synthesis, and high price of endoplasmic reticulum targeting reagents, and achieves easy mass acquisition and low cost , cheap effect

Inactive Publication Date: 2018-06-22
SICHUAN UNIV
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  • Summary
  • 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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  • 3, 5-dibenzimidazolyl-8-thiophenyl fluoroboron fluorescent derivatives as well as preparation method and application thereof
  • 3, 5-dibenzimidazolyl-8-thiophenyl fluoroboron fluorescent derivatives as well as preparation method and application thereof
  • 3, 5-dibenzimidazolyl-8-thiophenyl fluoroboron fluorescent derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Synthesis of 3,5-Dibenzimidazolyl-8-thienylfluoroborofluorene

[0051] Add 8-thienylfluoroborate (13.7mg, 0.05mmol), benzimidazole (23.6mg, 0.20mmol), AgOAc (33.4mg, 4.0equiv), dimethyl sulfoxide (1.0mL) into the reaction tube, and Stir evenly under nitrogen, heat to 80°C, and react 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 5.1 mg of yl-8-thienylfluoroborin, yield 20%.

[0054] The H spectrum and C ...

Embodiment 2

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

[0058] The compound 3,5-dibenzimidazolyl-8-thienylfluoroboron 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 UV-visible absorption spectrum and fluorescence emission spectrum of the compound 3,5-dibenzimidazolyl-8-thienylfluoroborate, wherein the black solid line represents the UV-vis 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 compound 3,5-dibenzimidazolyl-8-thienylfluoroborate is located at 559nm; the maximum absorption peak of the fluorescence emission spectrum is located at 590nm, and the Stoke...

Embodiment 3

[0061] The compound 3,5-dibenzimidazolyl-8-thienylfluoroborate 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-thienylflubororin 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-dibenzimidazolyl-8-thienylfluoroborate (excitation wavelength: 553nm, emission wavelength ...

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Abstract

The invention provides 3,5-dibenzimidazolyl-8-thiophenyl fluoroboron fluorescent derivatives, belonging to the technical field of fluoroboron fluorescent derivatives. The 3,5-dibenzimidazolyl-8-thiophenyl fluoroboron fluorescent derivatives have a structure shown in a formula (I), and the formula (I) is described in the description. The invention also provides a preparation method of the fluoroboron fluorescent derivatives. A synthetic route used in the method is a C-H / N-H direct oxidative coupling reaction; compared with the traditional fluoroboron fluorescent ammoniation preparation technology, the method provided by the invention reduces the organic synthesis steps, avoids the cumbersome process of pre-activation of a substrate, improves the reaction compatibility and increases the total yield of the synthetic reaction. After the fluoroboron fluorescent derivatives provided by the invention are applied to the endoplasmic reticulum specific fluorescence development and fluorescent labeling of cells, the cost of the derivatives is far lower than that of the commercially available cell endoplasmic reticulum labeling reagents, and the problems that in the prior art, an endoplasmic reticulum target agent is complicated in structure, inconvenient to synthesize and expensive in price can be solved.

Description

technical field [0001] The invention belongs to the technical field of fluoborofluores derivatives, and specifically relates to a 3,5-dibenzimidazolyl-8-thienyl fluoborofluores 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, Traffi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06C09B57/00G01N21/64
CPCC07F5/022C09K11/06C09K2211/1029C09K2211/1044C09K2211/1055C09K2211/1092G01N21/6486
Inventor 吴迪章华星兰静波杨宇东杨修光梁文博
Owner SICHUAN UNIV
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