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Fluorescent probe for identifying mercaptoamino-acid and preparation method of fluorescent probe

A fluorescent probe and identification technology, applied in the field of chemical analysis and detection, to achieve the effects of good selectivity, good cell membrane penetration, and strong anti-interference ability

Inactive Publication Date: 2019-05-28
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, it is still a challenge to develop fluorescent probes that can quickly detect thiol amino acids, and have long-wavelength emission and large Stokes shift.

Method used

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  • Fluorescent probe for identifying mercaptoamino-acid and preparation method of fluorescent probe
  • Fluorescent probe for identifying mercaptoamino-acid and preparation method of fluorescent probe
  • Fluorescent probe for identifying mercaptoamino-acid and preparation method of fluorescent probe

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1: the synthesis of compound 2

[0040] Compound 1 (3.32g, 10.0mmol) was dissolved in 50mL of ethylene glycol monomethyl ether, heated to 115°C until the reaction solution became clear, and then 3.0mL of hydrazine hydrate (80%) was added dropwise to the above mixed solution. After the addition was complete, the mixture was heated to reflux for 3 hours. After the reaction was completed, it was cooled to room temperature, and a large amount of orange precipitate was precipitated, which was filtered and washed to obtain compound 2. Yield: 2.32 g; Yield: 81.9%.

Embodiment 2

[0041] Embodiment 2: the synthesis of compound 3

[0042] Intermediate 2 (1.98g, 7mmol) was dissolved in 3-methyl-2-butanone (100mL), and then 3mL of concentrated sulfuric acid was slowly added dropwise, and the reaction mixture was refluxed and stirred for 4 hours under nitrogen protection. After the reaction was completed, , 3-methyl-2-butanone was removed by rotary evaporation under reduced pressure to obtain a crude product, which was separated and purified by silica gel column chromatography (petroleum ether / dichloromethane=1 / 10, v / v) to obtain product 3 as a pale yellow solid. Yield: 1.13 g; Yield: 48.5%.

Embodiment 3

[0043] Embodiment 3: the synthesis of compound 4

[0044] Compound 3 (1.0g, 3mmol) and p-Hydroxybenzaldehyde (0.37g, 3mmol) were dissolved in 20mL of dry toluene, stirred and mixed, and then glacial acetic acid (0.02mL) and piperidine (0.05mL) were added dropwise to the above mixture solution, after the dropwise addition, the mixed solution was refluxed and stirred for 6 hours under the protection of nitrogen, and the toluene was evaporated to dryness under reduced pressure to obtain a crude product, which was separated and purified by column chromatography (ethanol / dichloromethane=1 / 50, v / v ) to obtain product 4 as a red solid. Yield: 0.68 g; Yield: 51.7%.

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Abstract

The invention discloses a fluorescent probe for detecting mercaptoamino-acid based on naphthalimide indole and a preparation method of the fluorescent probe. The structure of the fluorescent probe isshown as follows (please see the specifications for the structure). The fluorescent probe is used for detecting cysteine, homocysteine and glutathione, and is good in selectivity, high in anti-interference capability and high in response speed; and meanwhile, the fluorescent probe has long-wavelength transmission and large stroke shift in the detecting process, detecting sensitivity can be improved, and small background interference can be achieved. The fluorescent probe can be used for detecting the mercaptoamino-acid in biological samples and cells.

Description

technical field [0001] The invention belongs to the technical field of chemical analysis and detection, and in particular relates to a fluorescent probe for detecting mercapto-containing amino acids and the application of the probe in detecting mercapto-amino acids. Background technique [0002] Cysteine ​​(Cys), homocysteine ​​(Hcy) and reduced glutathione (GSH) are the main biothiols and amino acids containing sulfhydryl groups, which are involved in the physiological and pathological processes of mammalian life systems play an important role. The abnormal concentration of cysteine ​​is related to many diseases. For example, when the concentration of cysteine ​​in the human body is too low, it can cause diseases such as slow growth and liver damage. Studies have shown that abnormal concentration of cysteine ​​is also related to skin damage, Drowsiness is related to diseases such as edema; increased concentration of homocysteine ​​is related to diseases such as cardiovascu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06G01N21/64
Inventor 刘兴江肜一帆王琛揣攀峰魏柳荷周爽高凯凯李庆昊
Owner ZHENGZHOU UNIV
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