Fluorescent probe for detecting hydrogen persulfide, synthetic method of fluorescent probe and application of fluorescent probe

A hydrogen persulfide, fluorescent molecular probe technology, applied in chemical instruments and methods, fluorescence/phosphorescence, organic chemistry, etc., can solve problems such as insufficient, unfavorable biological sample detection, excitation light interference sensitivity, etc., and achieve stable optical performance, High-sensitivity, fast-response effects

Active Publication Date: 2019-05-10
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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  • Fluorescent probe for detecting hydrogen persulfide, synthetic method of fluorescent probe and application of fluorescent probe
  • Fluorescent probe for detecting hydrogen persulfide, synthetic method of fluorescent probe and application of fluorescent probe
  • Fluorescent probe for detecting hydrogen persulfide, synthetic method of fluorescent probe and application of fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Synthesis of Fluorescent Molecular Probes

[0032] Compound 2 (80.8mg, 0.2mmol), 2-fluoro-5-nitrobenzoic acid (56mg, 0.3mmol), dicyclohexylcarbodiimide (54mg, 0.26mmol), 4-dimethylaminopyridine ( 4mg, 0.034mmol) was added to the solvent dichloromethane (15mL) and reacted at room temperature for 12h. 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 the product as a solid (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] Embodiment 2: Fluorescent detection of probes to hydrogen persulfide

[0036] The molecular probes prepared above were 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 2 mL of prepared 5 μmol L to a 3 mL cuvette -1 Probe solution of the present invention, then add hydrogen persulfide of different concentrations and mix evenly, test its fluorescence spectrum, the result is as follows figure 2 shown. The fluorescence emission intensity of the solution at 530nm is plotted against the concentration of hydrogen persulfide, and the concentration of hydrogen persulfide is 0–8 μmol L -1 In the range, there is a good linear relationship between the two ( image 3 ), the quantitative detection of hydrogen persulfide in this concentration range can be realized. And this probe is not affected by some other common substances, such as S 2- , S 2 o 3 2- , SO 3 2- , SO ...

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Abstract

The invention discloses a fluorescent probe for detecting hydrogen persulfide, a synthetic method of the fluorescent probe and an application of the fluorescent probe, and belongs to the technical field of chemical analysis and detection. A benzothiazole phenothiazine fluorogen with green fluorescence emission reacts with 2-fluoride-5-nitrobenzoic acid to obtain the probe which has a general structural formula as shown in the specification. The fluorogen of the probe is benzothiazole phenothiazine, and a hydrogen persulfide response group is 2-fluoride-5-nitrobenzoate. Probe molecules have high selectivity and sensitivity to the hydrogen persulfide, detection range is 0-8 micromoles*L<-1>, and detection limit is 26 nanomoles*L<-1>. The probe can be used for detecting the 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 fluorescent probe for detecting hydrogen persulfide, a synthesis 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 involved 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 suppression and so on. Therefore, it is necessary to develop a method for detecting hydrogen persulfide with high sensitivity and high selectivity 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 sample...

Claims

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Application Information

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Patent Type & Authority Applications(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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