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Fluorescent probe for detecting polarity in targeted endoplasmic reticulums and application thereof

A fluorescent probe and polarity technology, applied in the field of analytical chemistry, to achieve good fluorescence emission spectrum characteristics, cheap raw materials, and broad application prospects

Active Publication Date: 2019-08-23
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although various fluorescent probes for cell polarity detection have been reported, there is still a need for probes for targeted detection of cell polarity

Method used

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  • Fluorescent probe for detecting polarity in targeted endoplasmic reticulums and application thereof
  • Fluorescent probe for detecting polarity in targeted endoplasmic reticulums and application thereof
  • Fluorescent probe for detecting polarity in targeted endoplasmic reticulums and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1 Synthesis of Fluorescent Probes

[0028] (1) Dissolve Boc-ethylenediamine (950mg, 4.98mmol) in 15ml of dichloromethane, add triethylamine (2525mg, 24.95mmol) and stir at room temperature, and add p-toluenesulfonyl chloride (800mg, 5mmol) Dissolve in 8ml of dichloromethane and add dropwise to the reaction system, and continue to stir for 2 hours. Afterwards, the reaction solution was removed under reduced pressure to obtain a white solid. Finally, the white solid was dissolved in 30 ml of dichloromethane, about 8 ml of trifluoroacetic acid was added, and stirring was continued for 2 hours at room temperature. After the reaction was completed, the solvent in the reaction system was distilled off under reduced pressure, and the obtained crude product was purified by column chromatography to obtain a white solid, namely compound 1 (997mg, 93.2%), eluent: dichloromethane: Methanol: triethylamine=30:2:1,

[0029] ;

[0030] (2) Dissolve 4-methylthio-1,8-naphth...

Embodiment 2

[0034] Example 2 Fluorescence spectra of fluorescent probes in different polar solvents

[0035] Prepare 6 parts of 2μL 10mM probe master solution in advance, and then use toluene, 1,4-dioxane, tetrahydrofuran, dichloromethane, N,N-dimethylformamide, dimethyl sulfoxide to dilute to 4mL respectively to make the solution The system concentration was 5 μM, and then the fluorescence scanning (λ ex =405 nm); calculate the emission shift of the maximum fluorescence value in each system; evaluate the fluorescence spectrum of the fluorescent probe in different polar solvent conditions and obtain the final spectrum through processing, such as figure 2 ; and obtain the emission maxima and solvent polarity parameters of the probe in different solvents (E T (30)), such as image 3 shown. from figure 2 A red shift in the fluorescence spectrum can be observed with increasing solvent polarity. The maximum emission wavelength measured in toluene was 454 nm, while that in DMSO was 495 n...

Embodiment 3

[0036] Example 3 Selectivity of fluorescent probes to different ions

[0037] Prepare 18 parts of 4 mL of 5 μM probe buffer solution (containing 1% 1,4-dioxane, PBS buffer solution), and then add 100 μL of 40 mM PBS solutions of different substances to the system. Fluorescence detection is then performed (λ ex =405 nm); Calculate the fluorescence intensity in each system; Evaluate the interference of the different substances on the fluorescent probe solution, the results are as follows Figure 4 Shown, where 1-18 are PBS solution, KI, CaCl 2 , FeSO 4 , Cys, CoCl 2 , MgCl 2 , Fe 2 (SO 4 ) 3 , NaF, CuSO 4, GSH, Hcy, TBHP, DBTP, H 2 o 2 , ZnCl 2 , Na 2 SO 3 , H 2 S. Depend on Figure 4 It can be seen that in solutions with the same polarity, the fluorescence emission of different substances is basically the same, and the probe is not interfered by ions under the same polarity.

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Abstract

The invention provides a fluorescent probe for detecting the polarity in targeted endoplasmic reticulums, and the fluorescent probe has a structural formula shown in the description. The fluorescent probe for detecting the polarity in endoplasmic reticulums of cells can be obtained by chemical synthesis, the synthesis process is simple and easy to implement, the raw materials are cheap and easy toobtain, the preparation cost is low, and the popularization is easy; and the fluorescent probe has the advantages of high sensitivity and good fluorescence emission spectrum characteristic (415-700 nm), and can realize the purpose of quickly and accurately detecting the polarity in endoplasmic reticulums of normal cells and cancer cells by drawing a standard curve to measure the polarity in the endoplasmic reticulums of the cells. The fluorescent probe of the invention has high specificity, is not interfered by other components in the process of detecting the polarity of different solvent, can be used for real-time determination of the polarity in the endoplasmic reticulums of living cells, and has wide application prospects.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, and in particular relates to a fluorescent probe for detecting polarity and an application thereof. Background technique [0002] As a key parameter affecting chemical reactions, polarity not only plays an important role in the field of chemistry, but also affects and regulates certain physiological and pathological processes in biological microenvironments. Cell polarity is a specific feedback of a complex set of mechanisms that can serve as one of the important markers of its state changes and asymmetric distribution of cytoplasmic macromolecules. Most biochemical reactions in cells are related to the polarity of their surroundings. Besides that, in biological systems, especially at the cellular level, polarity plays a key role in controlling the behavior of functional proteins in cells. Abnormal polarity can lead to the occurrence of certain diseases, such as diabetes, polycysti...

Claims

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Application Information

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IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06C09K2211/1007C09K2211/1029G01N21/6428G01N21/643
Inventor 林伟英宋文辉董宝利卢雅茹
Owner UNIV OF JINAN
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