CN115078485B - Quick detection method for cyromazine residue based on molecular imprinting sensor - Google Patents
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Abstract
The invention discloses a method for rapidly detecting cyromazine residue based on a molecular imprinting sensor, which uses HAuCl 4 Modified screen printed carbon electrode, alphaMethacrylic acid is used as a functional monomer, cyromazine is used as a template molecule, trimethylolpropane trimethacrylate is used as a cross-linking agent, HCl is used as an eluent, and a molecular imprinting sensor for detecting cyromazine residues in agricultural products is prepared, and test results show that: the concentration of the cyromazine and the response current peak value of the sensor show good linear relation, the detection limit is 0.5 mu mol/L, meanwhile, the sensor has good repeatability and anti-interference performance, the cyromazine standard recovery rate is detected on cowpea samples, the standard recovery rate of the samples is 90% -105%, the Relative Standard Deviation (RSD) is less than 5%, the practicability and feasibility of the detection method established by the invention are proved, and the invention can lay a foundation for the research of the detection method for detecting the cyromazine residue in agricultural products.
Description
Technical Field
The invention relates to the technical field of pesticide residue detection, in particular to a method for rapidly detecting cyromazine residue based on a molecular imprinting sensor.
Background
Cyromazine is an insect growth regulator pesticide with strong systemic, stomach toxicity and contact killing capability, and is widely used for controlling diptera insect diseases and insect pests of cowpea, cucumber, eggplant and other crops at present. Cyromazine itself has very low toxicity to human beings, but after a large amount of degradation product trichlorocyanamide is ingested by human body, irreversible damage to kidney can be caused, and human health is seriously endangered.
At present, a relatively large number of mature technologies for detecting cyromazine residues are adopted, including methods such as indirect competitive enzyme-linked immunosorbent assay (ELISA), high Performance Liquid Chromatography (HPLC), gas chromatography-tandem mass spectrometry (GC-MS), ultra high performance liquid chromatography (UPLC), liquid chromatography-tandem mass spectrometry (LC-MS/MS) and the like. The method has the characteristics of high sensitivity, high accuracy and the like, but needs large-scale instrument and equipment support, and meanwhile, the operation procedure is tedious and long, and a skilled operation technology is needed, so that the detection cost of the sample is high, and the pesticide residue cannot be detected rapidly. Therefore, the invention provides a method for rapidly detecting cyromazine residue based on a molecular imprinting sensor.
Disclosure of Invention
In order to overcome the defects in the prior art, the embodiment of the invention provides a method for rapidly detecting cyromazine residue based on a molecular imprinting sensor, which aims to solve the problems in the prior art.
The embodiment of the application discloses: a method for rapidly detecting cyromazine residue based on a molecular imprinting sensor comprises the following steps:
drop 80. Mu.L of 0.2% HAuCl onto electrode 4 The deposition solution is deposited for 180 seconds under constant potential of-0.25V, after the deposition solution is finished, the electrode is taken down, the extra chloroauric acid solution is washed by ultrapure water, and the solution is dried for standby;
dripping 80 mu L cyromazine alpha-methacrylic acid polymeric solution on the electrode in the step (1) to completely cover the electrode, performing constant potential deposition for 300s under the condition of-1.0V, and flushing and drying by using ultrapure water after the polymeric deposition is finished;
dropwise adding 10 mu L of 6 mu mol/L trimethylolpropane trimethacrylate solution on the surface of the electrode in the step (2), and drying for 12 hours;
dripping 80 mu L of 1% HCL solution on the electrode prepared in the step (3), scanning for 30 circles by using a cyclic voltammetry under the potential interval of-0.4-0.8V, eluting template molecules, taking out the electrode after the completion, washing, drying and standing by to obtain the molecular imprinting sensor;
characterizing and testing performance of the prepared molecular imprinting sensor;
cleaning and drying a prepared sample, chopping and stirring uniformly, weighing 30g of homogenate, adding the homogenate into a 50mL centrifuge tube, swirling for 3min, centrifuging for 5min at 8000r/min, taking supernatant, filtering for standby, and adding a corresponding amount of cyromazine raw material into the supernatant to prepare a sample solution containing 1, 2 and 3 mu mol/L cyromazine;
soaking the molecular imprinting sensor in sample solutions to be tested of cyromazine with different concentrations, standing for 20min, drying, and dripping 60 μl containing 5.0mmol/L K 3 Fe(CN 6 ) The peak current values were recorded by scanning with a differential pulse voltammetry and three recordings were made for each concentration of each sample, and recovery and Relative Standard Deviation (RSD) were calculated.
Further, the characterization and performance test of the molecular imprinting sensor in the step (5) includes:
characterization of sensors CV and EIS, self-made sensors were immersed in a solution containing 5.0mmol/L K 3 Fe(CN 6 ) In 0.1mol/L KCl solution, scanning for 2 circles by Cyclic Voltammetry (CV) in a potential range of-0.4-0.6V to obtain a cyclic voltammogram of the sensor; using AC impedance method at 10 -1 ～10 -5 Scanning between HZ to obtain Electrochemical Impedance Spectrum (EIS) of the sensor;
the sensor scanning electron microscope characterization is carried out, a self-made sensor is scanned under a scanning electron microscope, a scanning electron microscope image of the sensor is obtained, and the surface of the sensor is observed and analyzed;
sensor performance DPV test at 5.0mmol/L K 3 Fe(CN 6 ) In a 0.1mol/L KCl solution, the prepared sensor was scanned by Differential Pulse Voltammetry (DPV) using a self-made portable sensor, and the peak current of the sensor at this time was recorded as I 0 The method comprises the steps of carrying out a first treatment on the surface of the The sensor was immersed in PBS solutions (ph=7.4) containing cyromazine at different concentrations, soaked and adsorbed for 20min, then taken out and dried, and scanned by Differential Pulse Voltammetry (DPV), and the peak current of the sensor at this time was designated as I. And the inhibition rate I% of cyromazine on the sensor is calculated according to the following formula.
Wherein I is 0 : sensor Differential Pulse Voltammetry (DPV) peak current without pesticide soaking; i: sensor Differential Pulse Voltammetry (DPV) peak current for soaking pesticides of different concentrations; i%: inhibition rates of different concentrations of cyromazine on the sensor;
repeatability test the same sensor was immersed in PBS solution containing 2. Mu. Mol/L cyromazine for 20min, 60. Mu.L containing 5.0mmol/L K 3 Fe(CN 6 ) Scanning with differential pulse voltammetry and repeating seven times, recording peak current values and calculating Relative Standard Deviation (RSD);
the anti-interference test is carried out, and two pesticides of atrazine and metolachlor with similar structures with cyromazine are selectedAs an anti-interference pesticide. The atrazine and the metolachlor are respectively added into 1 mu mol/L cyromazine solution to prepare mixed solution containing 5 mu mol/L, 10 mu mol/L, 20 mu mol/L and 30 mu mol/L cyromazine, and the mixed solution is used as interference solution. Soaking the sensor in the above solution sequentially according to gradient for 20min, taking out, drying, and dripping 60 μl containing 5.0mmol/L K 3 Fe(CN 6 ) The peak current value was recorded by scanning with a 0.1mol/L KCl solution and differential pulse voltammetry (CV).
The beneficial effects of the invention are as follows: the portable molecular imprinting sensor of the cyromazine is prepared under specific conditions by combining an electrochemical means with a molecular imprinting technology, adopting an electrochemical deposition method, using a chloroauric acid solution to modify an electrode, using cyromazine as a template molecule, alpha-methacrylic acid as a functional monomer, trimethylol propane trimethacrylate as a cross-linking agent and HCl as an eluent, and applying the method to rapid analysis and detection of the cyromazine in agricultural products such as cowpeas.
The foregoing and other objects, features and advantages of the invention will be apparent from the following more particular description of preferred embodiments, as illustrated in the accompanying drawings.
Drawings
In order to more clearly illustrate the embodiments of the invention or the technical solutions in the prior art, the drawings that are required in the embodiments or the description of the prior art will be briefly described, it being obvious that the drawings in the following description are only some embodiments of the invention, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
FIG. 1 is a sample of 5.0mmol/L K 3 Fe(CN 6 ) The structural characterization of the sensor in a 0.1mol/L KCl solution.
Fig. 2 is a sensor scanning electron microscope image.
FIG. 3 is a standard curve and inhibition curve for solutions of cyromazine at different concentrations.
Fig. 4 is a sensor repeatability test result.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
A method for quickly detecting cyromazine residue based on molecular imprinting sensor includes preparing molecular imprinting sensor, dropping 80 mu L of 0.2% HAuCl onto electrode 4 And (3) depositing the deposition solution for 180 seconds under constant potential at-0.25V, taking down the electrode after the deposition is completed, cleaning and drying, then dripping 80 mu L of cyromazine alpha-methacrylic acid polymerization solution on the prepared electrode to completely cover the electrode, depositing for 300 seconds under constant potential at-1.0V to enable the surface of the electrode to polymerize cyromazine and alpha-methacrylic acid simultaneously, flushing and drying by ultrapure water, dripping 10 mu L of 6 mu mol/L of trimethylolpropane trimethacrylate solution on the surface of the electrode, and drying for 12 hours. Dropping 80 mu L of 1% HCL solution on the electrode, scanning for 30 times by cyclic voltammetry with the potential interval of-0.4-0.8V, eluting the template molecules, taking out the electrode after completion, cleaning and drying;
electrochemical characterization and performance testing of sensors, characterization of sensors CV and EIS, immersion of self-made sensors in 5.0mmol/L K 3 Fe(CN 6 ) In 0.1mol/L KCl solution, scanning for 2 circles by Cyclic Voltammetry (CV) in a potential range of-0.4-0.6V to obtain a cyclic voltammogram of the sensor; using AC impedance method at 10 -1 ～10 -5 The Electrochemical Impedance Spectra (EIS) of the sensor were obtained by scanning between HZ, and the results are shown in FIG. 1 ((A) Cyclic Voltammogram (CV) a: bare electrode CV (bare SPCE); b: electrodeposited HAuCl) 4 A solution rear electrode; c: a polymeric cyromazine molecular polymer rear electrode; d: eluting the rear electrode; e, eluting a rear electrode (CK) of the non-imprinting sensor. (B) Electrochemical Impedance Spectroscopy (EIS) a: a bare electrode; b: electrodeposition of HAuCl 4 A solution rear electrode; c: a polymeric cyromazine molecular polymer rear electrode; d: electrodes after elution), FIG. 1A is a cyclic voltammetry analysis of each electrode. The results show that: chlorineCompared with a bare electrode, the peak value of the electrode after the gold acid deposition is obviously increased, which shows that the chloroauric acid is successfully modified on the surface of the electrode, the conductivity of the electrode is increased, and the peak current is increased. When cyromazine polymer is deposited on the electrode surface, electron transport is hindered, resulting in a reduction of peak current. Because the preparation process of the non-imprinting sensor does not have the participation of template molecules, the polymer chains cannot be crosslinked and grown, intermolecular gaps are narrowed, and the conductivity of the electrode is weakened, so that the peak current is small. The current after elution of the molecular imprinting sensor is larger than that after elution of the non-imprinting sensor, which shows that the imprinting sites on the surface of the sensor have good recognition performance on cyromazine molecules, and the prepared electrodes are respectively subjected to alternating current impedance spectrum analysis in the figure 1B. The results show that: after chloroauric acid deposition, electron transport is promoted and the impedance spectrum radius is significantly reduced. After polymer deposition, elution, the impedance spectrum radius increased, indicating successful binding of cyromazine a-methacrylic polymer to the sensor;
the sensor scanning electron microscope characterization scans a self-made sensor under a scanning electron microscope to obtain a scanning electron microscope image of the sensor, and the surface of the sensor is observed and analyzed, and the result is shown in a graph (A: a bare electrode CV (bare SPCE); B: an electrodeposited HAuCl4 solution rear electrode; C: a polymerized cyromazine molecular polymer rear electrode; D: an eluted rear electrode), wherein the surface of the electrode modified by chloroauric acid is provided with a plurality of small granular substances (graph 2B), and the surface of the electrode becomes smooth, which indicates that gold particles are successfully assembled on the sensor; after polymer deposition crosslinking, the electrode surface was visibly roughened and there were some lumps (fig. 2C) indicating successful deposition of cyromazine and alpha-methacrylic acid on the sensor, after elution with 1% hcl, the electrode surface became flat and smooth and the surface lumps decreased (fig. 2D) indicating successful elution of cyromazine molecules;
sensor Performance DPV test at 5.0mmol/LK 3 Fe(CN 6 ) In a 0.1mol/L KCl solution, the prepared sensor was scanned by Differential Pulse Voltammetry (DPV) using a self-made portable sensor, and the peak current of the sensor at this time was recorded as I 0 The method comprises the steps of carrying out a first treatment on the surface of the The sensor was then immersed in PBS solutions (pH=7.4), the sample was immersed and adsorbed for 20 minutes, and then taken out and dried, and the sample was scanned by Differential Pulse Voltammetry (DPV), and the peak current of the sensor at this time was designated as I. And the inhibition rate I% of cyromazine on the sensor is calculated according to the following formula.
Note that: i 0 : sensor Differential Pulse Voltammetry (DPV) peak current without pesticide soaking; i: sensor Differential Pulse Voltammetry (DPV) peak current for soaking pesticides of different concentrations; i%: the result of the inhibition rate of different concentrations of cyromazine on the sensor is shown in figure 3 (A: DPV curve of the molecular imprinting sensor for different concentrations of cyromazine; B: inhibition rate curve of the molecular imprinting sensor for different concentrations of cyromazine: 0, 0.5, 1.0, 1.5, 2.0, 2.5, 3.0 are different concentrations of cyromazine, wherein the concentration units are mu mol/L), the response current of the sensor changes along with the change of the concentration gradient of cyromazine, and when the concentration of cyromazine increases, the corresponding response current correspondingly decreases. Therefore, in a certain concentration range, a better linear relation exists between the response current and the pesticide concentration;
repeatability test the same sensor was immersed in PBS solution containing 2. Mu. Mol/L cyromazine for 20min, 60. Mu.L containing 5.0mmol/L K 3 Fe(CN 6 ) Scanning by differential pulse voltammetry, repeating seven times, recording peak current value and calculating Relative Standard Deviation (RSD), and the result is shown in figure 4, wherein the RSD value of the previous six times of test is 4.56% and the peak current is not obviously attenuated, and the RSD value is 7.54% by the seventh time, thus indicating that the prepared sensor has better accuracy in the test result within six times of continuous test;
and (3) testing the anti-interference performance, wherein two pesticides, namely atrazine and metolachlor with similar structures to cyromazine, are selected as anti-interference pesticides. The atrazine and the metolachlor are respectively added into 1 mu mol/L cyromazine solution to prepare mixed solution containing 5 mu mol/L, 10 mu mol/L, 20 mu mol/L and 30 mu mol/L cyromazine, and the mixed solution is used as interference solution. Sequentially soaking the sensor on the surface according to gradientThe solution was taken out and dried for 20min, 60. Mu.L of the solution containing 5.0mmol/L K was dropped 3 Fe(CN 6 ) The 0.1mol/L KCl solution was scanned by differential pulse voltammetry (CV), peak current values were recorded, and the results are shown in Table 1 and Table 2;
table 1 anti-tamper test results
Table 2 anti-tamper test results
The results showed that the 1. Mu. Mol/L cyromazine solution was similar to the peak current obtained by adding 5. Mu. Mol/L, 10. Mu. Mol/L, 20. Mu. Mol/L atrazine and metolachlor solutions to the 1. Mu. Mol/L cyromazine solution. The difference between the inhibition rate and the stock solution is less than 5%. The above results show that the molecularly imprinted sensor has good interference resistance.
Pretreating a sample to be tested, namely cleaning and drying purchased cowpeas, chopping and homogenizing, weighing 30g of homogenate, adding the homogenate into a 50mL centrifuge tube, swirling for 3min, centrifuging for 5min at 8000r/min, taking supernatant and filtering for later use. Adding a corresponding amount of cyromazine raw medicine into the supernatant to prepare a sample solution containing 1, 2 and 3 mu mol/L cyromazine;
testing sample solution, soaking the prepared sensor in sample solution to be tested of cyromazine with different concentrations, standing for 20min, taking out, drying, and dripping 60 μl containing 5.0mmol/L K 3 Fe(CN 6 ) Scanning with differential pulse voltammetry and recording peak current value, repeating each concentration of each sample three times, calculating recovery rate and Relative Standard Deviation (RSD), and the result is shown in Table 3;
table 3 actual sample recovery results
The results show that the standard adding recovery rate ranges of the tomato cowpea are respectively 90.14% -101.67% and 90.64% -101.10%, and the relative standard deviation is less than 5%. The molecular imprinting sensor is suitable for analysis and detection of cyromazine in actual samples.
The principles and embodiments of the present invention have been described in detail with reference to specific examples, which are provided to facilitate understanding of the method and core ideas of the present invention; meanwhile, as those skilled in the art will have variations in the specific embodiments and application scope in accordance with the ideas of the present invention, the present description should not be construed as limiting the present invention in view of the above.
Claims (1)
1. The quick detection method of cyromazine residue based on the molecular imprinting sensor is characterized by comprising the following steps:
(1) Drop 80. Mu.L of 0.2% HAuCl onto electrode 4 The deposition solution is deposited for 180 seconds under constant potential of-0.25V, after the deposition solution is finished, the electrode is taken down, the extra chloroauric acid solution is washed by ultrapure water, and the solution is dried for standby;
(2) Dripping 80 mu L cyromazine alpha-methacrylic acid polymeric solution on the electrode in the step (1) to completely cover the electrode, performing constant potential deposition for 300s under the condition of-1.0V, and flushing and drying by using ultrapure water after the polymeric deposition is finished;
(3) Dropwise adding 10 mu L of 6 mu mol/L trimethylolpropane trimethacrylate solution on the surface of the electrode in the step (2), and drying for 12 hours;
(4) Dropping 80 mu L of 1 percent HCL solution on the electrode prepared in the step (3), scanning for 30 circles by using a cyclic voltammetry under the potential interval of-0.4-0.8V, eluting template molecules, taking out the electrode after the completion, washing and drying for standby to obtain the molecular imprinting sensor;
(5) The prepared molecular imprinting sensor is characterized and tested for performance, and the characterization and the performance test specifically comprise:
characterization of sensors CV and EIS, self-made sensors were immersed in a solution containing 5.0mmol/L K 3 Fe(CN 6 ) In 0.1mol/L KCl solution, scanning for 2 circles by Cyclic Voltammetry (CV) in a potential range of-0.4-0.6V to obtain a cyclic voltammogram of the sensor; using AC impedance method at 10 -1 ～10 -5 Scanning between HZ to obtain Electrochemical Impedance Spectrum (EIS) of the sensor;
the sensor scanning electron microscope characterization is carried out, a self-made sensor is scanned under a scanning electron microscope, a scanning electron microscope image of the sensor is obtained, and the surface of the sensor is observed and analyzed;
sensor Performance DPV test at 5.0mmol/LK 3 Fe(CN 6 ) In a 0.1mol/L KCl solution, the prepared sensor was scanned by Differential Pulse Voltammetry (DPV) using a self-made portable sensor, and the peak current of the sensor at this time was recorded as I 0 The method comprises the steps of carrying out a first treatment on the surface of the Immersing the sensor in PBS solution with different concentration of cyromazine with pH=7.4, soaking and adsorbing for 20min, taking out and drying, scanning by Differential Pulse Voltammetry (DPV), recording peak current of the sensor as I, calculating inhibition rate I of cyromazine to the sensor according to the following formula,
wherein I is 0 : sensor Differential Pulse Voltammetry (DPV) peak current without pesticide soaking; i: sensor Differential Pulse Voltammetry (DPV) peak current for soaking pesticides of different concentrations; i%: inhibition rates of different concentrations of cyromazine on the sensor;
repeatability test, immersing the same sensor in PBS solution containing 2. Mu. Mol/L cyromazine for 20min, taking out, drying, and dripping 60. Mu.L containing 5.0mmol/L K 3 Fe(CN 6 ) Scanning with differential pulse voltammetry and repeating seven times, recording peak current values and calculating Relative Standard Deviation (RSD);
the anti-interference test, namely selecting two pesticides of atrazine and metolachlor with similar structures as cyromazine as anti-interference pesticides, and killing flies to 1 mu mol/LRespectively adding atrazine and metolachlor into amine solution to obtain cyromazine mixed solution containing 5 mu mol/L, 10 mu mol/L, 20 mu mol/L and 30 mu mol/L, sequentially soaking sensor in the mixed solution according to gradient for 20min, taking out, drying, and dripping 60 mu L containing 5.0mmol/L K 3 Fe(CN 6 ) 0.1mol/L KCl solution and scanning by differential pulse voltammetry (CV), recording peak current value;
(6) Cleaning and drying a prepared sample, chopping and stirring uniformly, weighing 30g of homogenate, adding the homogenate into a 50mL centrifuge tube, swirling for 3min, centrifuging for 5min at 8000r/min, taking supernatant, filtering for standby, and adding a corresponding amount of cyromazine raw material into the supernatant to prepare a sample solution containing 1, 2 and 3 mu mol/L cyromazine;
(7) Soaking the molecular imprinting sensor in sample solutions to be tested of cyromazine with different concentrations, standing for 20min, taking out, drying, and dripping 60 μl containing 5.0mmol/L K 3 Fe(CN 6 ) The peak current values were recorded by scanning with a differential pulse voltammetry and three recordings were made for each concentration of each sample, and recovery and Relative Standard Deviation (RSD) were calculated.
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