CN112903650A - Method for detecting quinoxaline compounds based on porous organic framework fluorescent film - Google Patents
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Abstract
The invention discloses a method for detecting quinoxaline compounds based on a porous organic framework fluorescent film, which takes the porous organic framework fluorescent film as a fluorescent substance and adopts a quenching fluorescence determination method to detect the quinoxaline compounds in a sample to be detected. The method adopts a quenching fluorescence determination method to detect the quinoxaline compound, can express the chemical information of the quinoxaline compound in the form of a fluorescence signal through a porous organic framework fluorescent film, and has the characteristics of good stability, shape and size adjustment, high mass transfer speed, good recoverability and portability, quenching effect on the quinoxaline compound and the like, so that the detection method has the advantages of high sensitivity, good selectivity, high response speed, reusability, small sample amount and simple operation.
Description
Technical Field
The invention belongs to the technical field of chemical detection and analysis, and particularly relates to a method for detecting quinoxaline compounds based on a porous organic framework fluorescent film.
Background
The quinoxaline compound is an artificially synthesized veterinary drug with a 1, 4-dinitronaphthalene structure, has the advantages of promoting the growth of animals, resisting infection activity, increasing protein quality and the like, and can be widely applied to animal husbandry and aquaculture as a feed additive. Carbadox and olaquindox are the most typical representatives of quinoxaline compounds, and are widely applied because of the promotion effect on animal growth and the prevention effect on bacterial enteritis and swine dysentery. However, toxicology studies have shown that they have severe toxicity and side effects. Therefore, it is very important to develop a simple, sensitive, rapid and effective assay to monitor carbalkoxy, olaquindox.
The analytical method for the detection of carbadox and olaquindox mainly comprises a high performance liquid chromatography and a liquid chromatography-tandem mass spectrometry combined method. However, these methods have the disadvantages of requiring complex technical equipment, expensive and time-consuming chromatography equipment, etc.
Disclosure of Invention
The present invention is directed to solving at least one of the problems of the prior art described above. Therefore, the invention provides a method for detecting quinoxaline compounds (namely a method for detecting quinoxaline compounds) based on a porous organic framework fluorescent film, which can be used for quickly, sensitively and simply detecting quinoxaline compounds.
The invention is realized by the following technical scheme:
a method for detecting quinoxaline compounds uses a porous organic framework fluorescent film as a fluorescent substance, and detects the quinoxaline compounds in a sample to be detected by a quenching fluorescence determination method.
Compared with the prior art, the invention has at least the following beneficial effects:
the quinoxaline compound is detected by adopting a quenching fluorescence determination method, chemical information of the quinoxaline compound can be expressed in a form of a fluorescence signal through a porous organic framework fluorescent film, and the method has the characteristics of good stability, shape and size adjustment, high mass transfer speed, good recoverability and portability, quenching effect on the quinoxaline compound and the like.
In some embodiments of the invention, the quinoxaline compound comprises at least one of carbalox, olaquindox, ciazalox, mequindox, and quinamine alcohol. Carbaloxy, olaquindox, ciazaloxy, mequindox and quinamine alcohol all have antibacterial and growth-promoting effects and all belong to quinoxaline-1, 4-nitrogen oxide derivatives.
In some embodiments of the invention, the quinoxaline-based compound comprises at least one of carbadox, olaquindox.
In some embodiments of the invention, the porous organic framework fluorescent film comprises a fluorescent porous organic framework compound comprising at least one of a tetraphenylmethane porous organic framework, 1,3, 5-triphenylbenzene, 2,4, 6-triphenyltriazine. Wherein the tetraphenylmethane porous organic framework has a structural formula shown in formula 1 below.
In some embodiments of the invention, the fluorescent porous organic framework compound is a tetraphenylmethane porous organic framework.
The porous organic framework materials such as the tetraphenyl methane porous organic framework and the like are novel porous grid materials formed by stable covalent bonds, and have the advantages of large specific surface area, high porosity, good hydrothermal stability, rich conjugated systems, various structures and the like. Moreover, the tetraphenyl methane porous organic framework has good fluorescence performance and reusability, has fluorescence quenching effect on quinoxaline compounds, and can be used for selectively detecting carbalkoxy and olaquindox.
In some embodiments of the present invention, the tetraphenylmethane porous organic framework is prepared by reacting tetrabromoteetraphenyl methane with 1,3, 5-tris (4-phenylboronic acid pinacol ester) benzene, as follows:
in some embodiments of the present invention, the reaction temperature of tetrabromotetraphenyl methane and 1,3, 5-tris (4-phenylboronic acid pinacol ester) benzene is 100 to 200 ℃.
In some embodiments of the invention, the reaction temperature of tetrabromotetraphenyl methane and 1,3, 5-tris (4-phenylboronic acid pinacol ester) benzene is 120-160 ℃.
In some embodiments of the invention, the reaction time of tetrabromotetraphenyl methane and 1,3, 5-tris (4-phenylboronic acid pinacol ester) benzene is 24-90 h.
In some embodiments of the present invention, the reaction time of tetrabromotetraphenyl methane and 1,3, 5-tris (4-phenylboronic acid pinacol ester) benzene is 60 to 80 hours.
In some embodiments of the invention, the reaction of tetrabromotetraphenyl methane and 1,3, 5-tris (4-phenylboronic acid pinacol ester) benzene is a Suzuki coupling reaction, which may be carried out with a base and a catalyst. The invention does not limit the alkali and the catalyst, and the alkali and the catalyst which are generally used for promoting the Suzuki coupling reaction can be applied to the synthesis of the tetraphenylmethane porous organic framework. As an example, the base may be selected from commonly used basic compounds such as sodium carbonate, sodium bicarbonate, sodium hydroxide, potassium hydroxide, etc., and the catalyst may be a palladium-containing compound such as tetrakis (triphenylphosphine) palladium (Pd (PPh)3)4)。
In some embodiments of the present invention, the molar ratio of tetrabromotetraphenyl methane to 1,3, 5-tris (4-phenylboronic acid pinacol ester) benzene is 1 (1-2).
In some embodiments of the invention, the molar ratio of the tetrabromotetraphenyl methane to the alkali to the catalyst is 1 (10-20) to (0.01-0.1).
In some embodiments of the invention, the tetraphenyl methane porous organic framework is prepared by mixing tetrabromo tetraphenyl methane, 1,3, 5-tris (4-phenylboronic acid pinacol ester) benzene, alkali, catalyst and solvent under a protective atmosphere, heating to 100-200 ℃ and reacting for 24-90 h; and after the reaction is finished, cooling, filtering, washing and drying to obtain the tetraphenylmethane porous organic framework.
In some embodiments of the invention, the washing is performed using hydrochloric acid, water, tetrahydrofuran, acetone, and dichloromethane in this order.
In some embodiments of the present invention, the porous organic-skeleton fluorescent film further comprises a film-forming material.
In some embodiments of the present invention, the film-forming material includes, but is not limited to, natural film-forming materials such as starch, cellulose, gelatin, and synthetic film-forming materials such as cellulose derivatives, polyvinyl alcohol, and polyvinylidene fluoride.
In some embodiments of the invention, the mass ratio of the fluorescent porous organic framework compound to the film-forming material is 1 (2-5).
In some embodiments of the present invention, the porous organic framework fluorescent film is prepared by dissolving a fluorescent porous organic framework compound and a film-forming material in a solvent to obtain a mixed solution; and forming a film by using the mixed solution to obtain the porous organic framework fluorescent film.
In some embodiments of the present invention, the method for detecting quinoxaline compounds comprises comparing fluorescence intensity changes of the porous organic framework fluorescent film before and after adding a sample to be detected, and obtaining a detection result of the quinoxaline compounds according to the fluorescence intensity changes.
In some embodiments of the present invention, the method for detecting quinoxaline compounds specifically comprises the following steps:
(1) obtaining the relation between the fluorescence intensity of the porous organic framework fluorescent film and the concentration of the quinoxaline compound;
(2) and (2) processing the porous organic framework fluorescent film by using a sample to be detected to obtain the fluorescence intensity to be detected, and then obtaining the detection result of the quinoxaline compound according to the relation in the step (1).
In some embodiments of the present invention, the step of obtaining the relationship between the fluorescence intensity of the porous organic framework fluorescent film and the concentration of the quinoxaline compound is specifically to add the porous organic framework fluorescent film into a series of quinoxaline compound standard solutions with different concentrations, and detect the fluorescence intensity of the porous organic framework fluorescent film after the porous organic framework fluorescent film is taken out, so as to obtain the relationship between the fluorescence intensity of the porous organic framework fluorescent film and the concentration of the quinoxaline compound.
In some embodiments of the invention, the sample to be tested is a solution. When an object to be detected is a solid, for example, when a feed is detected, the object to be detected needs to be pretreated to prepare a sample solution to be detected. The pre-treatment may include an extraction step.
In some embodiments of the present invention, the method for detecting quinoxaline compounds specifically comprises the following steps:
(1) preparing a feed to be detected into a sample solution to be detected for later use, and preparing standard solutions of quinoxaline compounds with different concentrations for later use;
(2) placing the porous organic framework fluorescent film on a solid support of a fluorescence spectrophotometer for scanning, and recording fluorescence spectrum intensity F0(ii) a Placing the porous organic framework fluorescent film into standard solutions with different concentrations for full mixing, then taking out the porous organic framework fluorescent film, detecting and recording the fluorescence intensity F generated by the porous organic framework fluorescent film, and obtaining the concentration of the quinoxaline compound and the fluorescence quenching degree F of the porous organic framework fluorescent film through data processing0Linear equation of/F-1;
(3) placing the porous organic framework fluorescent film on a solid support of a fluorescence spectrophotometer for scanning, and recording fluorescence spectrum intensity F0 ’(ii) a Placing the porous organic framework fluorescent film into a sample solution to be detected for full mixing, then taking out the porous organic framework fluorescent film for detection, and recording the fluorescence intensity F generated by the porous organic framework fluorescent film’(ii) a Then the degree of fluorescence quenching F detected by the fluorescence detector0 ’/F-1’And (3) substituting the linear equation obtained in the step (2) to obtain the concentration of the quinoxaline compound in the sample solution to be detected.
Compared with the prior art, the invention has the following beneficial effects:
the invention adopts the porous organic framework fluorescent film, detects the quinoxaline compound in the sample to be detected by quenching fluorescence determination method, can meet the requirements of quick, sensitive and simple detection of the quinoxaline compound, and has practical application value for the detection of the quinoxaline compound.
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The invention is further described with reference to the following figures and examples, in which:
FIG. 1 is a flow chart of the preparation of a porous organic framework fluorescent film;
FIG. 2 is a scanning electron microscope image of the top surface (A) and cross-section (B) of a porous organic framework fluorescent film;
FIG. 3 shows the fluorescence quenching results of the porous organic-skeleton fluorescent film for different growth-promoting compounds;
FIG. 4 is a diagram of the reuse of the porous organic-skeleton fluorescent film for detecting carbadox (A) and olaquindox (B);
FIG. 5 is a fluorescence quenching graph of a porous organic skeleton fluorescent film caused by different concentrations of carbalkoxy (A) and olaquindox (B) standard solutions and a linear equation of fluorescence quenching degree and concentration.
Detailed Description
The concept and technical effects of the present invention will be clearly and completely described below in conjunction with the embodiments to fully understand the objects, features and effects of the present invention. It is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments, and those skilled in the art can obtain other embodiments without inventive effort based on the embodiments of the present invention, and all embodiments are within the protection scope of the present invention.
The preparation method of the porous organic framework fluorescent film (hereinafter referred to as a matrix film) according to the process shown in FIG. 1 specifically comprises the following steps:
tetrabromoteetra-phenyl methane (500mg,0.79mmol), 1,3, 5-tris (4-phenylboronic acid pinacol ester) benzene (603mg,0.88mmol), and K under a nitrogen atmosphere2CO3(1.33g,9.6mmol) and Pd (PPh) as a catalyst3)4(34.8mg,0.03 mmol) was charged into a three-necked flask, followed by addition of 60mL of N, N-dimethylformamide and 4mL of ultrapure water, and the mixed solution was heated to 150 ℃ for reaction for 72 hours. After the reaction was completed and the flask was cooled to room temperature, the mixture was filtered to obtain an off-white precipitate. Washing with hydrochloric acid, ultrapure water, tetrahydrofuran, acetone and dichloromethane respectively, and washing with waterAnd (3) drying the washed precipitate for 12h in vacuum at 120 ℃ to obtain the tetraphenyl methane porous organic framework (TPM-POF).
300mg of polyvinylidene fluoride (PVDF) white powder was weighed into a 10mL stoppered glass vial, and a solvent (N, N-dimethylformamide solution) was added to the vial, followed by stirring at room temperature for 24 hours to obtain a transparent viscous solution. Then 75mg of tetraphenylmethane porous organic framework was weighed into the above clear viscous solution, and the mixture was stirred at room temperature for 24 hours and mixed well. The mixed solution was cast onto a clean glass plate and a flat membrane was prepared using a doctor blade. Then the flat membrane is put into ultrapure water to be soaked so that the membrane is quickly separated from the glass plate to obtain a matrix membrane (TPM-POF membrane).
A scanning electron micrograph of the top surface and cross-section of the matrix membrane is shown in fig. 2. As can be seen from fig. 2, the matrix membrane has a porous network structure.
The substrate film obtained above was cut with scissors into films having dimensions (length. times. width) of 1.0 cm. times.0.5 cm for use.
Selective testing
The quenching effect of 11 growth promoting compounds on the above-mentioned matrix membrane was examined, these compounds including: quinoxaline compounds: carbaloxy, olaquindox, other growth promoting compounds: tylosin, nandrolone phenylpropionate, clenbuterol, salinomycin, testosterone propionate, methyltestosterone, cyproheptadine, spiramycin and clonidine.
Specifically, a certain mass of the different growth promoting compounds is taken and prepared into sample solutions with the concentration of 5.0 [ mu ] mol/L for later use. And respectively placing the cut matrix membranes into the prepared sample solution for 30s, then taking out the matrix membranes, placing the matrix membranes on a sample support of a fluorescence spectrophotometer for scanning, and detecting and recording fluorescence spectra of the matrix membranes before and after the matrix membranes are added into the growth promoting drug solution by a detector. The parameters of the fluorescence spectrophotometer were set at λ ex-339 nm, λ em-393 nm, and excitation and emission slit width 2 nm.
As can be seen in FIG. 3 (F in FIG. 3)0Fluorescence intensity before adding detection solution to the matrix membrane, F is added to the matrix membraneDetecting the fluorescence intensity of the solution), and detecting the maximum fluorescence quenching when two quinoxaline compounds of carbalkoxy and olaquindox are added; while for the other 9 growth-promoting drugs, the matrix membrane produced only slight fluorescence intensity changes. The test result reflects that the matrix membrane has fluorescence quenching selectivity to the carbalkoxy and the olaquindox; functional units of the carbadox and the olaquindox are quinoxaline structures, and the substrate film has certain quenching selectivity to other quinoxaline compounds.
Repeatability test
And testing the cycle performance of the matrix membrane. Specifically, the matrix membrane was placed in a solution of carbalkoxy and olaquindox at a concentration of 5.0. mu. mol/L for 30 seconds, and then the matrix membrane was taken out, placed on a solid support of a fluorescence spectrometer, and the fluorescence emission spectrum of the matrix membrane was recorded. The fluorescent film was then taken out and washed three times with anhydrous methanol, dried, and the above detection process was repeated. After 7 cycles, the fluorescence intensity of the matrix membrane in the carbalkoxy and olaquindox solution changes F0The result of the equation,/F-1, is shown in FIG. 4. As can be seen from FIG. 4, the fluorescence properties of the matrix membrane are relatively stable after 7 cycles, and the RSD of the fluorescence response values of the matrix membrane to carbadox and olaquindox are both less than 8%.
Detection examples
A method for detecting quinoxaline compounds comprises the steps of adding a matrix membrane into a sample to be detected to be in full contact, then taking out the matrix membrane, and obtaining the concentration of the quinoxaline compounds to be detected in the sample to be detected by analyzing the change of fluorescence signal intensity before and after the matrix membrane is added into the sample to be detected.
The method comprises the following specific steps:
(1) preparing standard solutions of carbadox and olaquindox with concentrations of 0.3, 0.5, 0.6, 0.8, 1.0, 3.0, 5.0, 10.0, 15.0 and 20.0 mu mol/L respectively for later use. Scanning the matrix membrane on a solid support of a fluorescence spectrophotometer, and recording fluorescence spectrum intensity F0(ii) a Putting the matrix membrane into standard solutions with different concentrations for fully mixing, then taking out the matrix membrane, detecting and recording fluorescence intensity F generated by the matrix membrane, and obtaining the concentration of the carbadox and the olaquindox and the concentration of the porous membrane through data processingFluorescence quenching degree F of organic framework fluorescent film0Linear equation of/F-1. Fluorescence spectrum of substrate membrane after contacting different concentrations of carbadox and olaquindox standard solutions, and concentration of carbadox and olaquindox and F0The linear equation for/F-1 is shown in FIG. 5. Wherein the kappa oxygen concentrations c and F0The linear equation of/F-1 is F0/F-1＝-0.01+0.07c，R20.9904; olaquindox concentrations c and F0The linear equation of/F-1 is F0/F-1＝0.04+0.05c，R2＝0.9943。
(2) Taking a feed (pig feed, chicken feed or fish feed) to be detected as an example, the olaquindox content in the feed is detected. Weighing 5.0g of feed sample into a 50mL polypropylene centrifuge tube, adding 50mL of methanol/ultrapure water (v/v ═ 5:95) mixed solution, whirling for 5min, performing ultrasonic treatment for 5min, centrifuging the mixed solution for 5min at the rotation speed of 8000r/min, and collecting supernatant. The residue was extracted once more with 15mL of a mixed solution of methanol and ultrapure water, and the supernatants were combined. And then filtering the supernatant through an SPE small column, and eluting with methanol to obtain a sample solution to be detected for later use.
Scanning the matrix membrane on a solid support of a fluorescence spectrophotometer, and recording fluorescence spectrum intensity F0 ’(ii) a Putting the matrix membrane into a sample solution to be detected for full mixing, then taking out the matrix membrane for detection and recording the fluorescence intensity F generated by the matrix membrane’(ii) a Then the degree of fluorescence quenching F detected by the fluorescence detector0 ’/F-1’And (3) substituting the linear equation of the olaquindox obtained in the step (1) to obtain the concentration of the olaquindox in the sample solution to be detected. The results are shown in table 1 below (initial concentrations).
Meanwhile, the detection method is verified by combining a standard recovery method and is compared with an HPLC detection result. As shown in the following table 1, olaquindox (0.26, 0.79mg/L) with different concentrations is added into the feed for standard addition test, and the recovery rate is 97.4-107.7%. Each sample was tested in 3 replicates with RSD less than 5%. Meanwhile, the detection result of the quenching fluorescence detection method is almost the same as that of HPLC, which shows that the quenching fluorescence detection method has high detection accuracy. The test result shows that the matrix membrane has the potential of detecting the olaquindox in the actual sample.
TABLE 1 detection results of olaquindox in feed
-: it was not detected.
Claims (10)
1. A method for detecting quinoxaline compounds is characterized in that: and (3) taking the porous organic framework fluorescent film as a fluorescent substance, and detecting the quinoxaline compound in the sample to be detected by adopting a quenching fluorescence determination method.
2. The method for detecting quinoxaline compounds according to claim 1, wherein: the quinoxaline compound comprises at least one of carbalox, olaquindox, ciazalox, mequindox and quinamine alcohol.
3. The method for detecting quinoxaline compounds according to claim 1 or 2, wherein: the fluorescent film with the porous organic framework contains a fluorescent porous organic framework compound, and the fluorescent porous organic framework compound comprises at least one of a tetraphenyl methane porous organic framework, 1,3, 5-triphenyl benzene and 2,4, 6-triphenyl triazine; wherein the tetraphenylmethane porous organic framework has a structural formula as shown in formula 1 below:
4. the method for detecting quinoxaline compounds according to claim 3, wherein: the porous organic framework fluorescent film contains a tetraphenyl methane porous organic framework.
5. The method for detecting quinoxaline compounds according to claim 4, wherein: the tetraphenylmethane porous organic framework is prepared by reacting tetrabromoteetraphenyl methane with 1,3, 5-tris (4-phenylboronic acid pinacol ester) benzene.
6. The method for detecting quinoxaline compounds according to claim 5, wherein: the reaction temperature of the tetrabromotetraphenyl methane and the 1,3, 5-tri (4-phenylboronic acid pinacol ester) benzene is 100-200 ℃.
7. The method for detecting quinoxaline compounds according to claim 6, wherein: the reaction time of the tetrabromotetraphenyl methane and the 1,3, 5-tri (4-phenylboronic acid pinacol ester) benzene is 24-90 h.
8. The method for detecting quinoxaline compounds according to claim 3, wherein: the porous organic framework fluorescent film also contains a film forming material.
9. The method for detecting quinoxaline compounds according to claim 8, wherein: the film forming material comprises at least one of starch, cellulose, gelatin, bletilla gum, cellulose derivatives, polyvinyl alcohol and polyvinylidene fluoride.
10. The method for detecting quinoxaline compounds according to claim 1, wherein: the method for detecting the quinoxaline compound comprises the steps of comparing the fluorescence intensity change of the porous organic framework fluorescent film before and after the porous organic framework fluorescent film is added into a sample to be detected, and obtaining the detection result of the quinoxaline compound according to the fluorescence intensity change.
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| US5487953A (en) * | 1993-09-22 | 1996-01-30 | Pioneer Electronic Corporation | Organic electroluminescent device |
| CN108530423A (en) * | 2018-03-20 | 2018-09-14 | 华南理工大学 | A kind of water solubility aggregation-induced emission quinoxaline compounds and the preparation method and application thereof |
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