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Dansyl derivative fluorescent probe as well as synthesis method and application thereof

A technology of dansyl derivatives and fluorescent probes, applied in the field of dansyl derivative fluorescent probes and their synthesis, can solve the problems of complex operation, low selectivity, low sensitivity and the like, and achieves good selectivity and simple synthesis , prepare a simple effect

Active Publication Date: 2020-12-04
TAIYUAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The present invention solves existing H 2 The detection method of S has technical problems such as complex operation, low selectivity or low sensitivity. A dansyl derivative fluorescent probe and its synthesis method and application are provided. The synthesis method is simple in operation, low in equipment requirements, suitable for scale up production

Method used

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  • Dansyl derivative fluorescent probe as well as synthesis method and application thereof
  • Dansyl derivative fluorescent probe as well as synthesis method and application thereof
  • Dansyl derivative fluorescent probe as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Synthesize the dansyl derivative fluorescent probe with the following structural formula:

[0042]

[0043] Its synthetic steps are as follows:

[0044] Under nitrogen protection at a flow rate of 0.6mL / s and at room temperature, a chloroform solution containing 0.50 g (1.85 mmol) of dansyl chloride was added dropwise to a solution containing 253 μL (2.78 mmol) of 4-bromo-1-butanol and 385 μL of (2.78mmol) triethylamine in chloroform solution, after the dropwise addition was completed, the reaction was stirred at room temperature for 4 hours. Washed with saturated brine for 6 times, then dried with anhydrous sodium sulfate for 4 h, distilled off chloroform, and purified the product by column chromatography using a mixed solvent of dichloromethane and petroleum ether with a volume ratio of 1.5:1 as eluent, Obtain dansyl derivative fluorescent probe, its yield is 86%, and its reaction equation is as follows:

[0045]

[0046] The NMR data of the above-mentioned da...

Embodiment 2

[0048] Synthesize the dansyl derivative fluorescent probe with the following structural formula:

[0049]

[0050] Its synthetic steps are as follows:

[0051] In the synthesis steps of Example 1, the 4-bromo-1-butanol used was replaced by 6-bromo-1-hexanol with an equimolar mass, and other steps were the same as the corresponding Example 1.

Embodiment 3

[0053] Synthesize the dansyl derivative fluorescent probe with the following structural formula:

[0054]

[0055] Its synthetic steps are as follows:

[0056] In the synthesis step of Example 1, the 4-bromo-1-butanol used was replaced with 8-bromo-1-octanol of equimolar mass, and other steps were the same as the corresponding Example 1.

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Abstract

The invention belongs to the technical field of organic synthesis and biological mercaptan detection, and particularly relates to a dansyl derivative fluorescent probe as well as a synthesis method and application thereof. The synthesis method of the fluorescent probe comprises the steps: dropwise adding a trichloromethane solution of dansyl chloride into a trichloromethane solution containing bromo-substituted alcohol and triethylamine in an inert atmosphere at room temperature, stirring and reacting at room temperature after the dropwise addition is finished, washing and drying a reaction solution after the reaction is finished, evaporating to remove a solvent, separating and purifying a reactant through column chromatography, and thus obtaining the dansyl derivative fluorescent probe. The fluorescence probe and methyl green-pyronin Y are used as a double-fluorescence probe, and a supermolecular proportional fluorescence sensing platform is constructed by utilizing the solubilizationeffect of a surfactant CTAB and is used for selectively detecting H2S.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and biological thiol detection, and in particular relates to a dansyl derivative fluorescent probe and its synthesis method and application. Background technique [0002] Hydrogen sulfide (H 2 S), the simplest biothiol, is another endogenous gaseous signal molecule after carbon monoxide (CO) and nitric oxide (NO). It is widely distributed in various organs such as the liver, spleen and even the brain, participates in a series of physiological processes such as vasodilation, apoptosis and nerve regulation, and plays an irreplaceable role in maintaining normal physiological activities. Studies have shown that abnormal levels of it can trigger Alzheimer's disease, Down syndrome and diabetes, among others. Therefore, it is of great significance to develop a simple, reliable, highly selective, and highly sensitive method for the detection of hydrogen sulfide in biological samples. [0003]...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/76C07C303/28C09K11/06G01N21/64
CPCC07C309/76C09K11/06G01N21/6428C09K2211/1011G01N2021/6432G01N2021/6439
Inventor 范俊梅武恩瑞韩红斐董金龙王松李美琴洪昕悦
Owner TAIYUAN NORMAL UNIV
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