CN108003869B - Fluorescent probe for detecting hypochlorite with high sensitivity and synthesis method and application thereof - Google Patents
Fluorescent probe for detecting hypochlorite with high sensitivity and synthesis method and application thereof Download PDFInfo
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Abstract
The invention discloses a fluorescent probe for detecting hypochlorite with high sensitivity, a synthetic method and application thereof, and belongs to the technical field of chemical analysis and detection. The probe is obtained by dehydrating and condensing an aldehyde benzoxazole fluorophore and hydroxylamine and has the following structural general formula:
the fluorophore of the probe is benzothiazole skeleton structure, the response group to hypochlorite is hydroxylamine unit, the ultraviolet absorption peak of the single probe in solution is ~ 350nm, no obvious fluorescent emission is produced, the ultraviolet absorption peak is red shifted to ~ 410nm, the fluorescent emission at ~ 540nm is obviously enhanced, the ultraviolet lamp emits yellow fluorescent light, the probe molecule has high selectivity and sensitivity to hypochlorite and the detection range is 0.5-18 mu mol.L‑1The detection limit is 0.08 mu mol.L‑1. The probe can be used for imaging detection of hypochlorite in living cells.
Description
Technical Field
The invention belongs to the technical field of chemical analysis and detection, and particularly relates to a molecular probe for detecting hypochlorite by a fluorescence method, a preparation method of the molecular probe and application of the molecular probe in detecting hypochlorite.
Background
Hypochlorite (ClO)-) Or hypochlorous acid (HClO) is a commonly used disinfectant and oxidizer. And is a very important active oxygen in the organism, playing an important role in a plurality of physiological processes and diseases. For example, ClO produced by myeloperoxidase-catalyzed production of hydrogen peroxide and chloride ions during inflammation in humans-Has strong sterilization function. ClO on the other hand-Abnormal metabolism of the energy in the human body can lead to oxidation of oxidized amino acids, proteins, cholesterol and nucleic acids, thereby disrupting the function of these important biomolecules. Therefore, it is very necessary to develop a highly sensitive and selective method for detecting hypochlorite to accurately monitor the health status of human body.
The traditional methods for detecting hypochlorite include titration method, electrochemical method and the like. However, these methods are generally cumbersome to operate and difficult to perform in situ detection of biologically active samples. The molecular probe fluorescence method for detecting hypochlorite has the advantages of simple sample treatment, high measurement speed, capability of realizing in-situ real-time detection and the like, and is developed and utilized in recent years. However, the probe molecules developed at present for detecting hypochlorite have some defects, such as low sensitivity, complex synthesis, high preparation cost, complex reaction mechanism and the like (documents Jin X.L.Sens. initiators B.2016,232, 300; FanJ.L.analytes.2015, 140, 4594; Liao, Y-X.RSC adv.,2015,5, 18275; LiX.H.Sens. initiators B.2017.247.609). Therefore, there is a need to develop hypochlorite probes having superior performance to overcome the above problems.
Disclosure of Invention
Under the circumstances, the present invention aims to provide a novel fluorescent probe for detecting hypochlorite with high sensitivity, which is easy to prepare and has stable performance, a synthesis method of the probe, and a method for detecting hypochlorite with high selectivity and high sensitivity.
In order to realize the purpose of the invention, on one hand, the hydroxylamine group with a certain structure is designed to be selectively oxidized by hypochlorite by utilizing the fact that the hypochlorite has stronger special oxidability and can oxidize special electron-rich organic groups; on the other hand, the aldehyde-group benzoxazole has excellent spectral characteristics, fluorescence can be effectively quenched after the aldehyde group and hydroxylamine are subjected to condensation reaction, and strong fluorescence emission can be recovered after hydroxylamine is oxidized by hypochlorite. Based on the fluorescent molecular probe, a fluorescent molecular probe for detecting hypochlorite by taking hydroxylamine as a response group and taking aldehyde-based benzoxazole as a luminophore is designed.
The fluorescent molecular probe for detecting hypochlorite is characterized by having the following structural general formula:
wherein R is1S, O or NH; r2Is SH, OH or NH2(ii) a n is an integer from 1 to 18;
preferably: r1Is S or O; r2Is SH or OH; n is an integer of 1 to 6,
more preferably: r1Is S; r2Is OH. n is an integer of 1 to 4.
More preferably:
the synthesis method comprises the following steps:
dissolving the aldehyde benzoxazole and hydroxylamine in an organic solvent, adding organic base, performing reflux reaction, and separating and purifying to obtain the probe molecule.
Wherein R is1，R2n is the same as above.
The organic solvent is one or more of dichloromethane, ethanol, tetrahydrofuran, dimethylformamide and N-methylpyrrolidone.
The organic base is one or more of triethylamine, piperidine and pyridine.
In the method, the reaction temperature is the reflux temperature of the solvent.
The reaction time in the method is 0.5-24 h.
Preferably, the preparation method comprises the following steps:
dissolving aldehyde benzoxazole in ethanol, adding hydroxylamine and triethylamine, carrying out reflux reaction for 2-8h, carrying out reduced pressure distillation to remove the solvent, and then separating and purifying to obtain the probe molecular compound.
The synthesis method of the compound 1 comprises the following steps:
dissolving aldehyde benzothiazole in ethanol, adding hydroxylamine and triethylamine, carrying out reflux reaction for 2 hours, carrying out reduced pressure distillation to remove the solvent, and then separating and purifying to obtain the probe molecular compound 1. The reaction process is as follows:
the molecular probe is used for qualitatively and quantitatively measuring hypochlorite and is used for detecting hypochlorite in a water body or a biological system.
Detecting hypochlorite by adopting a fluorescence method, dissolving the molecular probe in a mixed buffer system of water and dimethyl sulfoxide, adding hypochlorite solutions with different concentrations, testing the fluorescence intensity of the hypochlorite solutions at 540nm, drawing a standard graph of the fluorescence intensity of the hypochlorite solutions at 540nm to the concentration of the hypochlorite, and quantitatively detecting the content of the hypochlorite solution to be detected according to the standard graph.
When the fluorescence method is adopted for detection, the detection concentration of the fluorescent molecular probe to hypochlorite is 0.5-1 mu mol.L-1The detection limit is 0.08 mu mol.L-1。
Another application mode of the molecular probe for detecting hypochlorite is to cultivate a cell biological sample with the molecular probe and detect hypochlorite in the cell biological sample by using a fluorescence imaging method.
The molecular probe for detecting hypochlorite by the fluorescence method is preferably synthesized by aldehyde benzothiazole and hydroxylamine through a condensation reaction, wherein the aldehyde benzothiazole is a fluorescent group; hydroxylamine is a responsive group to hypochlorite.
The synthesis and detection methods of the probe are described in more detail in the examples of the present specification. The fluorescent molecular probe is dissolved in a mixed buffer solution of water and dimethyl sulfoxide (DMSO), and after hypochlorite is added, the hypochlorite can oxidize a hydroxylamine group, so that the torsional quenching effect of-C-N-bonds is inhibited, the fluorescent emission of the probe solution is obviously enhanced, and the hypochlorite can be tested at room temperature.
The molecular probe for detecting hypochlorite by the fluorescence method is characterized by comprising the following specific steps:
the fluorescent probe molecule has good stability and optical property, the maximum absorption wavelength before reaction is 350nm, and no obvious fluorescence emission exists; with the addition of hypochlorite, a small absorption peak appears at the position of 410nm of an ultraviolet spectrogram of a probe molecule, and strong fluorescence emission appears at the position of 540nm, so that yellow fluorescence is observed.
The invention has the advantages that: the probe molecule has easily obtained raw materials and higher synthesis yield which is more than 65 percent. Stable optical performance (the probe solution can be stably stored in a room for more than three months, the spectral property of the probe solution is kept unchanged), high sensitivity, strong hypochlorite recognition capability, good selectivity, high response speed and response range of 0.5-18 mu mol.L-1And the detection limit is low (0.08 mu M, a method based on 3 times of blank sample standard deviation given by International Union of pure and applied chemistry), so the probe can be used for detecting hypochlorite in water bodies and biological systems.
Drawings
FIG. 1 shows the NMR spectrum of the molecular probe synthesized according to the present invention.
FIG. 2 shows 10. mu. mol. L of the present invention-1The molecular probe has ultraviolet absorption spectrum of 0, 0.5, 1, 2, 4, 6, 8, 10, 12, 14, 16, 18, 20 μmol.L from a to m after hypochlorite with different concentrations is added-1The solution system is a mixed buffer solution (H) of water and dimethyl sulfoxide2O/DMSO-9/1, v/v,10mM HEPES, pH 7.4), wavelength on the abscissa and absorbance on the ordinate.
FIG. 3 shows 10. mu. mol. L of the present invention-1The fluorescence emission spectrograms of the molecular probes after different concentrations of hypochlorite are added are from a to m, and the hypochlorite is concentratedThe degrees are respectively 0, 0.5, 1, 2, 4, 6, 8, 10, 12, 14, 16, 18 and 20 mu mol.L-1The abscissa is the wavelength and the ordinate is the fluorescence intensity.
FIG. 4 is a standard curve of hypochlorite concentration, i.e., 10. mu. mol. multidot.L-1The molecular probe of the invention has a linear relationship between the fluorescence emission intensity at 540nm and the hypochlorite concentration before and after reaction; the horizontal axis represents the concentration of hypochlorite, and the vertical axis represents the fluorescence emission intensity value.
FIG. 5 is a graph showing hypochlorite selectivity for the molecular probe of the present invention; namely, 10. mu.M of the molecular probe of the present invention was added with 20. mu. mol. L-1An oxidation active material (C)tBuOOH、Fe3+、H2O2、NO、1O2、·OH、·O2 –TBHP), fluorescence emission intensity value at 540 nm; the abscissa is the substance tested and the coordinate is the fluorescence emission intensity value.
FIG. 6 is an image of the molecular probe of the present invention for detecting hypochlorite in Hela cells. (A, B) are the fluorescent probes of the invention (10. mu. mol. L)-1) Bright field pictures and fluorescence pictures of cultured HeLa; (C, D) are the fluorescent probes of the invention (10. mu. mol. L)-1) And hypochlorite (20. mu. mol. L)-1) Bright field pictures and fluorescence pictures of cultured Hela cells. A scale: 50 μm.
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 Probe of the present invention
Carboxybenzothiazole (0.135g,0.5mmol) and hydroxylamine (0.033g,1.0mmol) were dissolved in ethanol (10mL), and triethylamine (0.101g,1.0mmol) was added thereto, followed by heating and refluxing for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and column chromatography was performed (eluent was a mixed solution of dichloromethane/methanol-2/3) to obtain 0.183g of a white solid (yield: 65%). The product has the following structural formula:
1H NMR(400MHz,DMSO):δ11.63(s,1H),8.45(s,1H),8.18(d,J＝7.6Hz,1H),8.09(d,J＝7.7Hz,1H),7.99(s,1H),7.56(d,J＝7.8Hz,2H),7.49(d,J＝7.6Hz,1H),2.36(s,3H).(see Figure S1).MS[ESI]:m/z,calcd for[M+H]+258.06；found 285.01.。
example 2: fluorescence detection of hypochlorite by probe
Dissolving the molecular probe prepared above in a mixed buffer solution (H) of water and dimethyl sulfoxide2O/DMSO-9/1, v/v,10mM HEPES, pH 7.4)), formulated to 10 μmol · L-1The probe solution of (1). To a 3mL cuvette, 2mL of 10. mu. mol. L prepared-1The probe solution of the invention is then added with hypochlorite with different concentrations respectively and then mixed evenly, and the ultraviolet and fluorescence spectra are tested, and the results are shown in figures 2 and 3. Plotting fluorescence emission intensity of the solution at 540nm against hypochlorite concentration of 0.5-18 μmol · L-1Within the range, a good linear relationship was exhibited between the two (FIG. 4). And the probe is not influenced by other common active oxidation substances, such as:tBuOOH、Fe3+、H2O2、NO、1O2、·OH、·O2 –TBHP. The probe still has good selectivity and sensitivity to hypochlorite under the condition of the existence of the interfering ions (figure 5).
The cells are cultured in a culture medium containing the probe of the present invention, and then in a solution containing hypochlorite. Red fluorescence was observed by cellular fluorescence imaging (fig. 6).
It can be seen that the invention can realize qualitative and quantitative detection of hypochlorite, has high sensitivity, and the detection limit reaches 0.08 mu mol.L-1And the anti-interference is strong, and the detection of intracellular hypochlorite can be realized.
Claims (9)
1. The fluorescent molecular probe for detecting hypochlorite is characterized by having the following structural general formula:
wherein R is1S, O or NH; r2Is SH, OH or NH2(ii) a n is an integer of 1 to 18.
2. The fluorescent molecular probe for detecting hypochlorite according to claim 1,
R1is S or O; r2Is SH or OH; n is an integer of 1 to 6.
3. The fluorescent molecular probe for detecting hypochlorite according to claim 2,
R1is S; r2Is OH; n is an integer of 1 to 4.
4. The fluorescent molecular probe for detecting hypochlorite is characterized in that the specific structure of the fluorescent molecular probe is as follows:
5. the method for synthesizing the fluorescent molecular probe for detecting hypochlorite according to claim 1, which is realized by the following method:
I
dissolving the aldehydic benzoxazole shown in the general formula I and hydroxylamine in an organic solvent, adding organic base, performing reflux reaction, and separating and purifying to obtain a probe molecule;
wherein: r1S, O or NH; r2Is SH, OH or NH2(ii) a n is an integer from 1 to 18;
the organic solvent is one or more of dichloromethane, ethanol, tetrahydrofuran, dimethylformamide and N-methylpyrrolidone; the organic base is one or more of triethylamine, piperidine and pyridine.
6. The method for synthesizing the fluorescent molecular probe for detecting hypochlorite according to claim 4, which is realized by the following method:
II
dissolving aldehyde benzothiazole shown in a formula II in ethanol, adding hydroxylamine and triethylamine, carrying out reflux reaction, carrying out reduced pressure distillation to remove a solvent, and separating and purifying to obtain the probe molecular compound.
7. Use of the fluorescent molecular probe for detecting hypochlorite according to any one of claims 1 to 4, wherein the molecular probe is used for qualitative or quantitative determination of hypochlorite in water and biological systems.
8. The use of the fluorescent molecular probe for detecting hypochlorite according to claim 7, wherein in the fluorescence detection, the molecular probe of the present invention is dissolved in a mixed buffer system of water and dimethyl sulfoxide, solutions containing hypochlorite at different concentrations are added to test the fluorescence intensity at 540nm, and then the fluorescence emission intensity of the solution at 540nm is plotted against the concentration of hypochlorite to quantitatively detect the content of hypochlorite in the solution to be detected according to the standard graph.
9. The use of the fluorescent molecular probe for detecting hypochlorite according to claim 7, wherein hypochlorite in a cellular biological sample is detected by incubating the cellular biological sample with the molecular probe of the present invention by a fluorescence imaging method.
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| CN110372632B (en) * | 2019-07-26 | 2021-04-06 | 广东轻工职业技术学院 | Fluorescent probe molecule for rapidly identifying hypochlorite ions and preparation method and application thereof |
| CN110627756B (en) * | 2019-10-10 | 2023-03-17 | 中国科学院新疆理化技术研究所 | Colorimetric-fluorescent probe for detecting hypochlorite and preparation method and application thereof |
| CN111087362B (en) * | 2019-12-18 | 2022-10-11 | 商丘师范学院 | Fluorescent probe for detecting formaldehyde with high selectivity, and synthetic method and application thereof |
| CN113218922B (en) * | 2021-03-12 | 2022-09-16 | 天津理工大学 | Coumarin skeleton-based rapid hypochlorite ratio detection type fluorescent probe and application thereof |
| CN113563257B (en) * | 2021-07-30 | 2022-03-29 | 忻州师范学院 | Hypochlorite fluorescent probe, preparation method and application thereof, and hypochlorite detection method |
| CN115161022A (en) * | 2022-07-12 | 2022-10-11 | 皖西学院 | Cationic fluorescent carbon dots sensitively responding to hypochlorous acid and preparation method thereof |
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