CN111138431A - Reactive fluorescent probe for detecting thiophenol and synthetic method and application thereof - Google Patents

Reactive fluorescent probe for detecting thiophenol and synthetic method and application thereof Download PDF

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CN111138431A
CN111138431A CN202010032681.5A CN202010032681A CN111138431A CN 111138431 A CN111138431 A CN 111138431A CN 202010032681 A CN202010032681 A CN 202010032681A CN 111138431 A CN111138431 A CN 111138431A
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thiophenol
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郝远强
张银堂
董辉
韩华博
韦秀华
朱旭
瞿鹏
徐茂田
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Shangqiu Normal University
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    • C07—ORGANIC CHEMISTRY
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    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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Abstract

The invention discloses a near-infrared fluorescent probe for detecting thiophenol, a synthetic method and application thereof, and belongs to the technical field of chemical analysis and detection. The probe is obtained by the reaction of 8- (2, 4-dinitrophenoxy) julolidine-9-formaldehyde and 4-pyridine acetonitrile, and has the following structure:
Figure DEST_PATH_IMAGE002
the probe has a response group of 2, 4-dinitrophenoxy to the thiophenol, and the probe and the thiophenol can further generate intramolecular cyclization reaction to generate coumarin fluorescent molecules with strong fluorescence emission, so that the fluorescent detection of the thiophenol is realized. The probe molecule has high selectivity and sensitivity to thiophenol, and the detection range is 0-12 mu mol.L‑1The detection limit is33 nmol·L‑1. The probe can be used for detecting thiophenol in water, soil and cells.

Description

Reactive fluorescent probe for detecting thiophenol and synthetic method and application thereof
Technical Field
The invention belongs to the technical field of chemical analysis and detection, and particularly relates to a reactive fluorescent probe for detecting thiophenol, a synthesis method thereof and application thereof in the aspect of detecting thiophenol.
Background
Thiophenol (C)6H5SH, PhSH) is an aryl sulfide with high reactivity and has wide applications in the synthesis industry, such as synthesis of sulfonamides, pesticides and macromolecules. On the other hand, thiophenol is highly toxic and respiratory and dermal uptake can lead to a variety of conditions such as dyspnea, muscle weakness, central nervous system injury and even death. The U.S. occupational safety and health administration defines a working environment for thiophenol of 0.1ppm maximum. With the emission and toxic action of a large amount of industrial use of thiophenol, the development of a method for detecting thiophenol with high sensitivity and high selectivity is very necessary for environmental detection and protection.
The fluorescence method based on the molecular probe has the advantages of simple sample treatment, low cost, simple and quick operation and the like, and is developed and utilized in recent years. However, the existing fluorescent probe molecules for detecting thiophenol have the problems of complex synthesis, insufficient selectivity and sensitivity, poor water solubility and the like (Zhang W.J.dyes and Pigments 2016,133,248; Pagidi S.Langmuir 2018,34, 8170; Genga Y.Sensors & actors: B.chemical 2018,273,1670.), and therefore, development of thiophenol detection probes with excellent performance is urgently needed to overcome the problems.
Disclosure of Invention
Under the circumstances, the invention aims to provide a novel fluorescent molecular probe which is easy to prepare, stable in performance, excellent in analysis performance and good in water solubility, a synthetic method of the probe and a detection method for carrying out high selectivity and high sensitivity on thiophenol on the basis of the synthetic method.
In order to realize the purpose of the invention, the invention utilizes the characteristic of stronger nucleophilic reaction of thiophenol, which can react with electron-deficient molecules or groups, and 2, 4-dinitrophenyl ether can react with thiophenol specifically, and the 2, 4-dinitrophenyl ether is adopted as a response group of the thiophenol. On the other hand, the coumarin fluorescent molecule has the advantages of good stability, high luminous intensity, good water solubility and the like, and the reactive site and the spectral property can be regulated and controlled.
The structural formula of the fluorescent molecular probe for detecting thiophenol is as follows:
Figure BDA0002364900200000021
the synthetic reaction process is as follows:
Figure BDA0002364900200000022
the synthesis method comprises the following steps:
adding a catalyst, a compound 2 and pyridine acetonitrile into an organic solvent, and reacting under the heating condition of 50-120 ℃; after the reaction is finished, the solvent is dried by decompression and spinning, and the obtained crude product is separated by a chromatographic column to obtain a target product probe molecule 1;
the organic solvent is selected from one of acetonitrile, ethanol, dimethylformamide and N-methylpyrrolidone;
the catalyst is selected from one of piperidine, acetic acid, sodium acetate and triethylamine.
The reaction time is 1-24 h.
The reaction temperature is 50-120 ℃.
The reaction conditions are still more preferably as follows:
the organic solvent is selected from ethanol.
The catalyst is selected from piperidine.
The reaction time was 6 h.
The reaction temperature was 80 ℃.
The molecular probe is used for qualitative and quantitative determination of thiophenol, and is used for detection of thiophenol in water, soil or biological systems.
When the colorimetric method or the fluorescence method is adopted for detection, the molecular probe is dissolved in a phosphoric acid buffer solution to test the thiophenol. When thiophenol is added, the thiophenol can attack phenoxy group through nucleophilic attack, and further through removing reaction, the phenolic hydroxyl group of the probe is dissociated out, and further generates intramolecular addition cyclization reaction with cyanide, thereby obtaining the coumarin fluorescent molecule with strong fluorescence emission.
When the detection is carried out by adopting a fluorescence method, the detection concentration of the fluorescent molecular probe to the thiophenol is 0-12 mu mol.L-1The detection limit is 33 nmol.L-1。
The fluorescent probe molecule of the invention has the following characteristics and advantages:
the fluorescent probe molecule has good stability and optical property, and no fluorescence emission exists in a single probe solution before reaction; with the addition of thiophenol, the probe molecule has strong fluorescence emission property at-545 nm.
The probe molecule of the invention has easily obtained raw materials, higher synthesis yield which is more than 90 percent, stable optical performance (probe mother liquor can be stably stored for more than three months indoors, and the spectral property of the probe mother liquor is kept unchanged), high selectivity and high sensitivity, strong recognition capability on the thiophenol, higher response speed and response range of 0-12 mu mol.L-1Low detection limit (33 nmol. L)-1) Therefore, the probe can be used for qualitative or quantitative detection of thiophenol in water, soil and biological systems.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of a molecular probe synthesized according to the present invention;
FIG. 2 shows 10. mu. mol. L of the present invention-1The fluorescence emission spectrograms of the molecular probes after adding different concentrations of thiophenol are respectively 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 and 13 mu mol.L from a to N-1The solution system was a phosphoric acid mixed buffer solution of water (10mM, pH 7.4), the abscissa is the wavelength and the ordinate is the fluorescence intensity.
FIG. 3 is a graph showing the standard curve of the concentration of thiophenol, i.e., 10. mu. mol. L-1The molecular probe of the invention has a linear relationship between the fluorescence emission intensity and the thiophenol concentration at 545nm before and after reaction; the abscissa represents the concentration of thiophenol and the ordinate represents the fluorescence intensity.
FIG. 4 shows the selectivity of the molecular probe of the present invention for thiophenol; namely, 10. mu.M of the molecular probe of the present invention was added to 100. mu. mol. L-1Change of fluorescence emission intensity at 545nm after different substances (sodium nitrate, copper chloride, cysteine, glutathione, homocysteine, sodium carbonate, sodium sulfide, sodium acetate, sodium fluoride, thiophenol and phenol); the abscissa is the interfering substance tested and the ordinate is the fluorescence intensity.
FIG. 5 is an image of the molecular probe of the present invention for detecting thiophenol in human gastric cancer cells (MGC-803). (A, B) are the molecular fluorescent probes of the invention (10. mu. mol. L)-1) Bright field pictures and fluorescent pictures of the cultured MGC-803 cells; (C, D) are the molecular fluorescent probes of the invention (10. mu. mol. L)-1) And thiophenol (20. mu. mol. L)-1) Bright field and fluorescent pictures of cultured MGC-803 cells.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
Example 1: synthesis of fluorescent molecular probes
Compound 2(0.2g, 0.522mmol) and 4-pyridineacetonitrile (0.05g, 0.522mmol) were dissolved in absolute ethanol (10mL), piperidine (0.1mL) was added to the reaction mixture, and the reaction mixture was refluxed at 80 ℃ for 6 hours. After completion of the reaction, the filtrate was removed by suction filtration, and the cake was retained and purified by column chromatography using dichloromethane/ethyl acetate (1:1, volume ratio) as an eluent, followed by rotary drying under reduced pressure to obtain 0.221g (yield: 88%) of a yellow solid. The product has the following structural formula:
Figure BDA0002364900200000041
1H NMR(400Hz,CDCl3) δ 8.81(d, J ═ 2.7Hz,1H),8.56(d, J ═ 4.8Hz,2H),8.29(dd, J ═ 9.3,2.7Hz,1H),8.14(s,1H),7.78(s,1H),7.40(d, J ═ 6.2Hz,2H),6.84(d, J ═ 9.3Hz,1H),3.36(t, J ═ 5.4Hz,2H), 3.33-3.27 (m,2H),2.85(d, J ═ 6.3Hz,2H),2.74(s,1H),2.22(s,1H),2.03(dt, J ═ 11.9,6.0Hz,2H),1.92(dd, J ═ 11.7,6.0Hz, 1H), fig. 2H). MS [ ESI ]]:m/z,calcd for[M+H]+484.16；found 484.04。
Example 2: fluorescent detection of probe p-thiophenol
The molecular probe prepared above was dissolved in a mixed buffer solution of phosphoric acid (10mM, pH 7.4) to prepare 10. mu. mol. L-1The probe solution of (1). To a 3mL cuvette, 2mL of 10. mu. mol. L prepared-1The probe solution of the present invention was mixed with thiophenol of different concentrations, and the fluorescence spectrum was measured, and the results are shown in FIG. 2. Plotting the fluorescence emission intensity of the solution at 545nm on the concentration of thiophenol, wherein the concentration of the thiophenol is 0-12 mu mol.L-1Within this range, a good linear relationship is shown (FIG. 3), enabling quantitative detection of thiophenol within this concentration range. And the probe is not influenced by other common substances, such as sodium nitrate, copper chloride, cysteine, glutathione, homocysteine, sodium carbonate, sodium sulfide, sodium acetate, sodium fluoride and phenol. The probe still has good selectivity and sensitivity to the phenol containing the thiophenol under the condition of the existence of the interfering ions (figure 4).
Example 3: test of thiophenol in cells with the Probe of the present invention
Cultured human gastric cancer cells (MGC-803) are placed in 10 mu M PBS solution of the probe of the invention at 37 ℃ and cultured for 1h to obtain a cell image without fluorescence. MGC-803 cells were cultured at 37 deg.C for 1h with the probe culture solution of the present invention, then added with thiophenol, cultured for 1h with a thiophenol-containing solution, and washed with PBS buffer to obtain fluorescence imaging of the cells, as shown in FIG. 5. Therefore, the probe of the invention has good cell membrane permeability and can be used for cell imaging analysis in the biomedical field.

Claims (4)

1. A fluorescent molecular probe for detecting thiophenol is characterized in that the structural formula is as follows:
Figure FDA0002364900190000011
2. a method for synthesizing a fluorescent molecular probe for the detection of thiophenol according to claim 1, wherein said method comprises the steps of:
Figure FDA0002364900190000012
adding a catalyst, a compound 2 and pyridine acetonitrile into an organic solvent, and reacting at 50-120 ℃; after the reaction is finished, the solvent is dried by decompression and spinning, and the obtained crude product is separated by a chromatographic column to obtain a target product probe molecule 1;
the organic solvent is selected from one of acetonitrile, ethanol, dimethylformamide and N-methylpyrrolidone;
the catalyst is selected from one of piperidine, acetic acid, sodium acetate and triethylamine.
3. The application of the fluorescent molecular probe for detecting thiophenol as claimed in claim 1, wherein when fluorescence detection is adopted, the molecular probe is dissolved in a phosphoric acid mixed buffer system, thiophenols with different concentrations are added, the fluorescence intensity of the thiophenols at 545nm is respectively tested, and then the fluorescence emission intensity of the solution at 545nm is used as a standard graph; and (5) quantitatively detecting the content of the thiophenol in the solution to be detected according to the standard graph.
4. Use of a fluorescent molecular probe for the detection of thiophenol according to claim 1, wherein the thiophenol in a cellular biological sample is qualitatively detected by fluorescence imaging by incubating the cellular biological sample with the molecular probe of the invention.
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CN112209923A (en) * 2020-10-14 2021-01-12 中南大学 Synthesis and application of near-infrared fluorescent probe for high-selectivity detection of Cys/Hcy and GSH

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* Cited by examiner, † Cited by third party
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CN111205220A (en) * 2020-02-26 2020-05-29 湖南中大检测技术集团有限公司 Fluorescent probe and preparation method and application thereof
CN112209923A (en) * 2020-10-14 2021-01-12 中南大学 Synthesis and application of near-infrared fluorescent probe for high-selectivity detection of Cys/Hcy and GSH

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