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Water-soluble fluorescent probe based on C-glycoside, synthesis and applications thereof

A fluorescent probe and water-soluble technology, which is applied in the synthesis field of glycoside fluorescent probe compounds, can solve the problems of high purity requirements, cumbersome operation and low sensitivity of the detection substance, and achieves good water solubility, strong adhesion ability, Wide range of effects

Inactive Publication Date: 2016-05-25
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the detection of sulfhydryl groups is mainly through colorimetry, electrochemistry, mass spectrometry and other methods, but these methods are cumbersome to operate, require high purity of the detected substance, and have low sensitivity.

Method used

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  • Water-soluble fluorescent probe based on C-glycoside, synthesis and applications thereof
  • Water-soluble fluorescent probe based on C-glycoside, synthesis and applications thereof
  • Water-soluble fluorescent probe based on C-glycoside, synthesis and applications thereof

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Experimental program
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Effect test

Embodiment 1

[0029] Preparation of compound 2

[0030]

[0031] 0.226g (1mmol) of 3-acetyl-5-C-(2,3-dihydroxy-1,4-anhydro-D-erythrofuranosyl)-2-methylfuran 1 (wherein, 3- For the preparation of acetyl-5-C-(2,3-dihydroxy-1,4-anhydro-D-erythrofuranosyl)-2-methylfuran, please refer to the literature: Xiang Yanfei, Fang Zhijie, Li Longxia, CoCl2 6H2O, AlCl3 6H2O catalyzed the synthesis of C-pyrroloside in aqueous phase, Chemical Research and Application, 2013, 25(10):1426-1429.) was dissolved in 4mL ethanol, and 4-N was added to the reaction system by pipetting, 0.266g (1.5mmol) of N-diethylaminobenzaldehyde and 0.15mL of 10% NaOH aqueous solution were stirred at room temperature for 8h and tracked by TLC. 20 mL of NaCl solution was washed three times, the organic layer was dried over anhydrous sodium sulfate, filtered, and distilled under reduced pressure to obtain a crude product, which was separated and purified by silica gel column chromatography (petroleum ether:ethyl acetate=3:1) to ...

Embodiment 2

[0036] Effects of different solvents on the UV and fluorescence spectra of the fluorescent probe.

[0037] Different solvents will have a certain impact on the fluorescence intensity and maximum absorption wavelength of the fluorescent probe. figure 1 with figure 2 The property changes of the ultraviolet and fluorescence spectra of the fluorescent probe 2 of carbonoside sugar in different solvents are given. from figure 1 It can be seen that the maximum UV absorption wavelength of the compound has little change, figure 2 The change of the fluorescence maximum absorption wavelength is more obvious, and the Stokes shift of the fluorescent probe 2 is obtained by calculation. Compared with other fluorescent probes (most fluorescent substances have Stokes shifts between 50-70nm), this fluorescent compound has a significant Large Stokes shift (86nm, solvent is acetonitrile). The compound is in DMF, CH 3 The fluorescence absorption is stronger in polar aprotic solvents such as...

Embodiment 3

[0039] The relationship between the fluorescence intensity and the concentration of the fluorescent probe compound 2 of sugar carbosides.

[0040] image 3 The fluorescence intensity and concentration change curves of the fluorescent probe series compound 2 of carbonoside sugars are given. It can be obtained from the graph that compound 2 is in acetonitrile solvent. When the concentration reaches 4×10 -5 When the concentration is higher, the fluorescence intensity is the highest, and when the concentration continues to increase, the fluorescence gradually begins to weaken.

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Abstract

The present invention discloses a water-soluble fluorescent probe based on C-glycoside, synthesis and applications thereof. According to the present invention, the fluorescent probe is obtained through a two-step reaction, and has characteristics of cheap and easily-available reaction raw materials, less reaction steps, high yield and the like; and the water-soluble fluorescent probe based on C-glycoside has the following uses such as pH value analysis, mercapto anion detection and protein labeling, wherein the fluorescent probe does not produce fluorescence under an acidic condition and maintains fluorescence under an alkaline condition so as to perform pH value analysis by using the acid-alkali switching characteristic, the mercapto can be selectively detected by using the characteristic of the alpha,beta-unsaturated ketone (providing the electrophilic center property), and the characteristic that the fluorescent compound produces weak fluorescence or does not produce fluorescence in a protic solvent, but produces fluorescence after protein is added to the aqueous solution of the compound is utilized to label the protein and enhance the protein detection sensitivity.

Description

technical field [0001] The present invention relates to a novel water-soluble fluorescent probe based on sugar carbon glycosides and its preparation method and application, specifically, to the synthesis of a sugar carbon glycoside fluorescent probe compound with a diethylaminobenzaldehyde structure and its application. Background technique [0002] At present, most of the sugar-based fluorescent probes are obtained by combining sugar molecules with fluorescent compounds (such as rhodamine, coumarin) through glycosidic bonds, thereby modifying different fluorescent compounds. There is very little research. Carbon glycosides have attracted the attention of many scholars at home and abroad because of their good chemical and biological stability compared to natural O- and N-glycosides, that is, acid and alkali resistance and stability to glycosidases. [0003] In proteins, the sulfhydryl moiety is the most reactive functional group related to enzyme activity, so it is particu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D307/46G01N21/64C07K1/13
Inventor 方志杰张涛顾小敏卢庆光
Owner NANJING UNIV OF SCI & TECH