A kind of fluorescent probe for detecting hydrogen persulfide and its synthesis method and application

A technology of hydrogen persulfide and fluorescent molecular probes, applied in chemical instruments and methods, fluorescence/phosphorescence, organic chemistry, etc., can solve the problems of excitation light interference sensitivity, insufficient, unfavorable detection of biological samples, etc., and achieve high sensitivity, optical Stable performance, high selectivity effect

Active Publication Date: 2022-07-29
SHANGQIU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In this way, the excitation light is easy to cause interference and the sensitivity is not enough, so it is not conducive to the detection of biological samples

Method used

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  • A kind of fluorescent probe for detecting hydrogen persulfide and its synthesis method and application
  • A kind of fluorescent probe for detecting hydrogen persulfide and its synthesis method and application
  • A kind of fluorescent probe for detecting hydrogen persulfide and its synthesis method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Example 1: Synthesis of Fluorescent Molecular Probes

[0032] Compound 2 (80.8 mg, 0.2 mmol), 2-fluoro-5-nitrobenzoic acid (56 mg, 0.3 mmol), dicyclohexylcarbodiimide (54 mg, 0.26 mmol), 4-dimethylaminopyridine ( 4 mg, 0.034 mmol) was added to the solvent dichloromethane (15 mL) and reacted at room temperature for 12 h. After the reaction was completed, the solvent was distilled off under reduced pressure and separated by column chromatography (eluent: petroleum ether:ethyl acetate=5:1, v / v) to obtain 68.6 mg of solid product (yield: 87%). The product structural formula is as follows:

[0033]

[0034] 1H NMR(400MHz, DMSO)δ9.02(s,1H),8.70(s,1H),8.06(d,J=7.0Hz,1H),7.95(s,1H),7.91-7.77(m,1H) ,7.74(d,J=7.3Hz,1H),7.35(ddd,J=38.5,19.1,7.3Hz,5H),7.19–6.92(m,2H),3.95(s,2H),1.71(s,2H) ),1.42(d,J=5.7Hz,2H),0.89(s,3H).MS[ESI]:m / z,calcd for[M+H] + 572.1114, Found: 572.1121.

Embodiment 2

[0035] Example 2: Fluorescence detection of hydrogen persulfide by probe

[0036] The molecular probe prepared above was dissolved in a mixed buffer solution of water and acetonitrile (H 2 O / CH 3 CN=1 / 1, v / v, 10mM HEPES, pH 7.4)), prepared as 5μmol·L -1probe solution. Add 2mL of prepared 5μmol·L to a 3mL cuvette -1 The probe solution of the present invention is then added with different concentrations of hydrogen persulfide and evenly mixed, and its fluorescence spectrum is tested, and the results are as follows figure 2 shown. The fluorescence emission intensity of the solution at 530nm was plotted against the concentration of hydrogen persulfide, and the concentration of hydrogen persulfide was 0–8 μmol·L -1 Within the range, there is a good linear relationship between the two ( image 3 ), can realize the quantitative detection of hydrogen persulfide in this concentration range. And this probe is not affected by some other common substances, such as S 2- , S 2 O ...

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Abstract

The invention discloses a fluorescent probe for detecting hydrogen persulfide, a synthesis method and application thereof, and belongs to the technical field of chemical analysis and detection. The probe of the invention is obtained by reacting a benzothiazole phenothiazine fluorophore with green fluorescence emission with 2-fluoro-5-nitrobenzoic acid, and has the following general structural formula: the fluorophore of the probe is benzothiazole phenothiazine oxazine, the responsive group to hydrogen persulfide is 2-fluoro-5-nitrobenzoate. The probe molecule has high selectivity and sensitivity to hydrogen persulfide, and the detection range is 0–8 μmol·L ‑1 , the detection limit is 26 nmol·L ‑1 . The probe can be used for the detection of hydrogen persulfide in water, soil and cells.

Description

technical field [0001] The invention belongs to the technical field of chemical analysis and detection, and in particular relates to a trun-on type fluorescent probe for detecting hydrogen persulfide, a combination method thereof, and an application in detecting hydrogen persulfide. Background technique [0002] Hydrogen persulfide (H 2 S 2 ) is an important biological sulfur-containing molecule that participates in the relevant physiological processes of cell protection. In addition, hydrogen persulfide also plays some other physiological regulatory functions, such as transcription activator, ion channel, tumor suppressor and so on. Therefore, it is necessary to develop a highly sensitive and selective detection method for hydrogen persulfide to elucidate the physiological and pathological processes of hydrogen persulfide. [0003] The fluorescence detection method based on fluorescent probe has the advantages of fast response, high sensitivity and selectivity, simple sa...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/04C09K11/06G01N21/64
Inventor 郝远强刘保霞张银堂朱旭韦秀华瞿鹏徐茂田
Owner SHANGQIU NORMAL UNIVERSITY
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