CN114935589A - Electrochemical immunosensor based on mimic enzyme and preparation method and application thereof - Google Patents
Electrochemical immunosensor based on mimic enzyme and preparation method and application thereof Download PDFInfo
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- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/531—Production of immunochemical test materials
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/536—Immunoassay; Biospecific binding assay; Materials therefor with immune complex formed in liquid phase
Abstract
The invention discloses an electrochemical immunosensor for detecting Deoxynivalenol (DON), a preparation method and an application thereof 2 the-MIL 101 derivative (BNM) is used as an electrode modification material, DON antibody is fixed on the surface of the electrode modification material by a covalent binding method, the modification material is dispersed in chitosan and fixed on an electrode, thionine is used as a probe molecule, the peroxidase property of BNM can be spatially inhibited due to the formation of an immune complex on the surface of the electrode, so that the peak current of an electroactive substance is reduced, and the deoxynivalene can be realized by utilizing the change of the currentQuantitative determination of alcohol (DON). The immunosensor has high sensitivity, strong anti-interference performance and short detection time; the preparation method is simple in steps and low in cost.
Description
Technical Field
The invention relates to an electrochemical immunosensor, a preparation method and application thereof, in particular to preparation of the electrochemical immunosensor based on nano BNM mimic enzyme and application of the electrochemical immunosensor in Deoxynivalenol (DON) detection.
Background
Deoxynivalenol (DON), also known as vomitoxin, is one of the most representative mycotoxins in the trichothecene family. Its main products include fusarium graminearum and fusarium graminearum. Researches show that the residual Deoxynivalenol (DON) in the feed can cause animal diarrhea, vomit and livestock and poultry tissue injury, and the residual Deoxynivalenol (DON) in the food can cause chronic toxicity of organs such as liver, heart, kidney and the like of human beings, thereby seriously harming human health. While Deoxynivalenol (DON) is very stable in the conventional processing process of food and feed.
Therefore, the development of a method for detecting the residual Deoxynivalenol (DON) in food and feed is very important.
Disclosure of Invention
The purpose of the invention is as follows: the electrochemical immunosensor is rapid, sensitive, specific and reliable in Deoxynivalenol (DON) detection, simple and convenient to operate and low in cost.
The current type label-free immunoassay method is based on the specific combination of antigen and antibody, and the immune complex formed on the surface of the electrode hinders the electron transmission between the electrochemical active probe and the electrode, so that the peak current of the electroactive substance is reduced, and the quantitative detection of the Deoxynivalenol (DON) can be realized by utilizing the change of the current. However, the existing traditional electrochemical probe is applied to label-free electrochemical sensing, the detection sensitivity of the sensor is not high, and the advantage of high-sensitivity detection of the amperometric label-free immunoassay method cannot be fully exerted on Deoxynivalenol (DON) detection.
With the rapid development of nanotechnology, researches find that the defect is made up by the combined use of some artificially synthesized inorganic nanomaterials and an immunosensor.
The invention relates to MOF material NH formed by combining ferric ion solution and organic ligand (2-amino terephthalic acid) 2 -MIL-101 octahedral structure, in which defects are induced in the framework by a long-chain fatty acid modulator with C12 or higher, in NH 2 The surface of MIL-101 generates a multi-crystallite spherical structure to generate more reaction catalytic sites, and the nano BNM obtained by pyrolysis has the following advantages: (1) the kit has high-efficiency catalytic activity for simulating horseradish peroxidase, and realizes effective detection of Deoxynivalenol (DON) antigen by taking thionine and hydrogen peroxide as enzyme reaction substrates. (2) Because of the amino group on the surface of the BNM, the Deoxynivalenol (DON) antibody can be directly connected to the nano BNM material in a covalent bonding mode through a cross-linking agent, so that the antibody is favorably loaded on an electrode, and the detection of the Deoxynivalenol (DON) antigen is also favorably realized.
The technical scheme is as follows:
in a first aspect, a method for preparing an electrochemical immunosensor for detecting Deoxynivalenol (DON) is provided, which comprises the following steps:
a. preparation of nano BNM mimic enzyme
Mixing a ferric ion-containing solution prepared by a long-chain fatty acid modulator with 2-amino terephthalic acid, growing crystals at a set temperature, centrifuging, collecting, drying and calcining to obtain a BNM material;
b. preparation of BNM-DON antibody-chitosan solution
Binding the deoxynivalenol DON antibody to the surface of BNM by using a cross-linking agent to obtain a BNM-DON antibody compound; then, the BNM-DON antibody compound is dispersed in the chitosan solution to prepare a BNM-DON antibody-chitosan solution;
c. preparation of working electrode of Deoxynivalenol (DON) electrochemical immunosensor
Dropwise adding a BNM-DON antibody-chitosan solution on the pretreated glassy carbon electrode to obtain a BNM-DON antibody-chitosan composite electrode;
and (3) blocking the non-specific binding sites on the BNM-DON antibody-chitosan composite electrode by using a serum albumin solution, and then washing to obtain the electrochemical immunosensor.
In some embodiments, in step a, the molar ratio of ferric ions to the long-chain fatty acid modulator to the 2-amino terephthalic acid is 69 (30-50) to 30-40; preferably 69:40: 35.
In some embodiments, in step a, the source of ferric ions is one or more of ferric chloride, ferric sulfate, ferric acetate or ferric chloride hydrate, ferric sulfate hydrate and ferric acetate hydrate;
preferably, the source of ferric ions is dissolved in dimethylformamide to form a ferric ion containing solution.
In some embodiments, in step a, the long chain fatty acid modulator is selected from one or more of palmitic acid, stearic acid, lauric acid, arachidic acid;
in some embodiments, the alkyl chain length carbon atoms are gradually increased, inducing NH 2 The more microcrystalline spherical structures are present on the surface of MIL101 due to defects, thus palmitic acid is preferred as a modulator.
In some embodiments, the crystal growth temperature in step a is 160-240 ℃, preferably 200 ℃.
The calcination process is carried out in a nitrogen atmosphere, and the calcination temperature is 250-350 ℃, preferably 300 ℃.
In some embodiments, the crosslinking agent is selected from one or more of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide, 1-cyclohexyl-2-morpholinoethylcarbodiimide, and glutaraldehyde, and preferably the crosslinking agent is glutaraldehyde.
In some embodiments, the covalent binding of the deoxynivalenol DON antibody to a BNM surface using a cross-linking agent comprises:
the BNM is dispersed in PBS buffer solution, then mixed with a cross-linking agent, and after the mixture is incubated, the mixture is centrifuged to obtain BNM-g;
and mixing and reacting BNM-g with DON antibody solution, and covalently combining the DON antibody and BNM-g to obtain a BNM-DON antibody compound.
Further, the concentration of the DON antibody solution is 0.5-2 mug/mL.
In a second aspect, an electrochemical immunosensor is provided, which is prepared according to the preparation method.
In a third aspect, the application of the electrochemical immunosensor in Deoxynivalenol (DON) detection is provided.
In some embodiments, the application comprises the following steps:
s1, detecting electrochemical behavior of the electrochemical immunosensor: dripping a certain amount of DON antigen with different concentrations onto the electrochemical immunosensor to serve as a working electrode, forming a three-electrode measuring system with a reference electrode and an auxiliary electrode, and performing electrochemical measurement in a PBS (phosphate buffer solution) solution containing thionine and hydrogen peroxide by adopting a differential pulse voltammetry method to obtain a fitting linear regression equation and a detection limit of the electrochemical immunosensor to the DON;
s2, measurement of actual sample: and dripping the processed sample to be detected on the electrochemical immunosensor to serve as a working electrode, forming a three-electrode system with the reference electrode and the auxiliary electrode, carrying out electrochemical measurement, and calculating the concentration of the DON in the sample to be detected by utilizing a fitting linear regression equation of the electrochemical immunosensor to the DON.
Preferably, in the step S1, the concentration of the DON antigen is 10-10 7 pg/mL. The reference electrode adopts a calomel electrode, and the auxiliary electrode adopts a platinum wire electrode.
Has the advantages that: compared with the prior art, the invention has the following remarkable advantages: 1. the surface of the nano BNM mimic enzyme of the immunosensor is provided with amino, and the mimic enzyme does not need to introduce the amino when being connected with an antibody in a subsequent covalent binding mode; 2. the immunosensor uses artificially synthesized nano BNM mimic enzyme to overcome the defects that the traditional biological enzyme is easy to be changed, has poor stability and catalytic activity is easily influenced by environment (pH, temperature, air pressure) and the like; 3. compared with a sandwich immune electrochemical sensor, the immune sensor does not need a labeled antibody, and avoids the inactivation of the antibody.
Drawings
FIG. 1 is a scanning electron micrograph of BNM in example 1;
FIG. 2 is a UV analysis of the performance of the BNM in example 1 and the NM mimic enzyme in example 2;
fig. 3 is a graph of the linear relationship between the concentration of DON antigen in solution and its corresponding peak current for the three-electrode system of the example.
Detailed Description
The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and such ranges or values should be understood to encompass values close to those ranges or values. For ranges of values, between the endpoints of each of the ranges and the individual points, and between the individual points may be combined with each other to give one or more new ranges of values, and these ranges of values should be considered as specifically disclosed herein.
For the purposes of the present specification and appended claims, unless otherwise indicated, all numbers expressing quantities, percentages or proportions, and other numerical values used in the specification and appended claims, are to be understood as being modified in all instances by the term "about". Moreover, all ranges disclosed herein are inclusive of the endpoints and independently combinable.
In the description of the present invention, reference to the description of the terms "one embodiment," "some embodiments," "an illustrative embodiment," "an example," "a specific example," or "some examples," etc., means that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the present invention. In this specification, the schematic representations of the terms used above do not necessarily refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.
Example 1
1. Preparing a Deoxynivalenol (DON) electrochemical immunosensor based on a nano BNM mimic enzyme:
a. preparation of nano BNM mimic enzyme
0.69mmol of ferric chloride hexahydrate (FeCl) 3 ·6H 2 O) was dissolved in 30mL of Dimethylformamide (DMF), and 0.4mmol of the solution was addedThe above solution was heated to 130 ℃ for 1 hour. Further addition of 0.35mmol of 2-aminoterephthalic acid (NH) 2 -H 2 BDC) and rapidly heated to 200 ℃ for 2 hours, after cooling to room temperature, the product is collected by centrifugation, washed 3 times with acetone and deionized water and dried. And calcining the dried solid product at 300 ℃ for 2 hours in a nitrogen atmosphere, washing the calcined product for multiple times by using acetone and deionized water, and drying the washed product to obtain BNM powder. The scanning electron micrograph is shown in FIG. 1.
b. Preparation of BNM-DON antibody-Chitosan solution
The DON antibody was covalently bound to the BNM surface using glutaraldehyde as a cross-linker. Briefly, 10mg of BNM was dispersed in 5mL of PBS buffer (pH 7.4) to prepare a 2mg/mL BNM solution, which was then mixed with 1mL of glutaraldehyde solution (50% in water). The mixture was incubated at room temperature (RT, 25. + -. 2 ℃) for 30 minutes. The glutaraldehyde-treated BNM (BNM-g) described above was then separated from the solution by centrifugation. To prepare the BNM-DON antibody complex, 5mg BNM-g was mixed with 15mL of a 1. mu.g/mL DON antibody solution. The solution was reacted overnight (room temperature) and DON antibody was covalently bound to BNM-g. Finally centrifugation separates the BNM-DON antibody from the reaction mixture. Subsequently, the solution was washed with PBS buffer, dispersed in 1.0 wt% chitosan solution and sonicated for 10min to obtain BNM-DON antibody-chitosan solution.
c. Preparing a working electrode of the Deoxynivalenol (DON) electrochemical immunosensor.
Pretreating glassy carbon electrode by respectively adding 1.0 μm and 0.3 μm Al to the glassy carbon electrode 2 O 3 Polishing to a mirror surface on the chamois, washing off surface dirt after each polishing, and then transferring to ethanol and deionized water for 10min of ultrasound. Dropwise adding 5.0 mu L of BNM-DON antibody-chitosan solution onto the pretreated glassy carbon electrode, drying at 4 ℃ for 12h to obtain a BNM-DON antibody-chitosan composite electrode;
and (3) sealing the obtained electrode and a 1% bovine serum albumin solution at room temperature for 1 hour, blocking a non-specific binding site, and washing the electrode again by using a PBS (phosphate buffer solution) to obtain the electrochemical immunosensor for detecting DON.
2. The use method of the Deoxynivalenol (DON) electrochemical immunosensor based on the nano BNM mimic enzyme comprises the following steps:
s1, when in use, firstly 5 mul of the extract is mixed with 10-10 7 The DON solution in pg/mL is dripped on an electrochemical immunosensor for detecting DON, the electrochemical immunosensor is used as a working electrode, a platinum wire electrode is used as a counter electrode, a calomel electrode is used as a reference electrode to form a classic three-electrode structure, electrochemical measurement is carried out in 10mL PBS solution with pH value of 5.5 and containing 0.025mM thionine and 0.5mM hydrogen peroxide, Differential Pulse Voltammetry (DPV) is adopted, and parameters are set as follows: amplitude of 50 mV; the pulse width was 0.05 s; the pulse period was 0.5 s. The dot scatter distribution diagram can be obtained by using DON with different concentrations as abscissa and peak current value as ordinate, as shown in FIG. 3, and analysis after straight line fitting shows that the peak current value detected by the composite electrode is 10-10 7 The linear relation is good in the pg/mL interval, the linear regression equation is that y is 0.959x-11.136, and R 2 When the concentration was 0.998, the detection limit was 9.55 pg/mL.
S2, measurement of actual sample: non-contaminated wheat flour was obtained from the local market as a test sample. Distilled (DI) water was chosen as the extraction solvent for DON analysis for this study. Vomitoxin (1.5X 10) was added to 5.0g wheat flour at various concentrations 2 、1.5×10 4 、1.5×10 6 pg/mL) was stirred in 25 mL of deionized water at room temperature for 15 minutes, and then centrifuged at 5000 rpm for 10 minutes, and the supernatant was filtered. The sensor is used for detecting the samples, the detection is repeated for 5 times, the results are shown in table 1, the Relative Standard Deviation (RSD) of the immunosensor is between 2.6% and 3.4%, and the recovery rate is between 94.7% and 104.7%, and the immunosensor provided by the invention can be well applied to DON determination.
TABLE 1 actual sample testing
Example 2 (comparative example)
The difference between this example and example 1 is that in step 1, a: 0.69mmol of FeCl 3 ·6H 2 O and 0.35mmol of NH 2 -H 2 BDC was dissolved in 30mL of DMF and sonicated for 10min (without conditioning with palmitic acid). Subsequently, the solution was placed in an oven and rapidly heated to 200 ℃ for 2 hours. After cooling to room temperature, the product was collected by centrifugation, washed 3 times with acetone and deionized water and dried. Calcining the dried solid product for 2 hours at 300 ℃ in the nitrogen atmosphere, finally washing the solid product with acetone and deionized water for multiple times and drying the solid product to obtain calcined NH 2 -MIL-101(NM) powder; it was finally found that its peroxidase-like activity was lower than that of BNM. As shown in particular in fig. 2.
The above description is only of the preferred embodiments of the present invention, and it should be noted that: it will be apparent to those skilled in the art that various modifications and adaptations can be made without departing from the principles of the invention and these are intended to be within the scope of the invention.
Claims (10)
1. A preparation method of an electrochemical immunosensor is characterized by comprising the following steps:
a. preparation of nano BNM mimic enzyme
Mixing a ferric ion-containing solution prepared by a long-chain fatty acid modulator with 2-amino terephthalic acid, growing crystals at a set temperature, centrifuging, collecting, drying and calcining to obtain a BNM material;
b. preparation of BNM-DON antibody-chitosan solution
Binding the deoxynivalenol DON antibody to the surface of BNM by using a cross-linking agent to obtain a BNM-DON antibody compound; then, the BNM-DON antibody compound is dispersed in the chitosan solution to prepare a BNM-DON antibody-chitosan solution;
c. preparation of working electrode of deoxynivalenol electrochemical immunosensor
Dropwise adding a BNM-DON antibody-chitosan solution on the pretreated glassy carbon electrode to obtain a BNM-DON antibody-chitosan composite electrode;
and (3) blocking the non-specific binding sites on the BNM-DON antibody-chitosan composite electrode by using a serum albumin solution, and then washing to obtain the electrochemical immunosensor.
2. The production method according to claim 1,
in the step a, the molar ratio of ferric ions to the long-chain fatty acid modulator to the 2-amino terephthalic acid is 69 (30-50) to 30-40; preferably 69:40: 35;
and/or in the step a, the source of ferric ions adopts one or more of ferric chloride, ferric sulfate, ferric acetate or ferric chloride hydrate, ferric sulfate hydrate and ferric acetate hydrate;
and/or in the step a, the long-chain fatty acid modulator is selected from one or more of palmitic acid, stearic acid, lauric acid and arachidic acid; palmitic acid is preferred.
3. The preparation method according to claim 1, wherein in the step a, the crystal growth temperature is 160-240 ℃, preferably 200 ℃;
and/or the calcining process is carried out in a nitrogen atmosphere, the calcining temperature is 250-350 ℃, and the preferred calcining temperature is 300 ℃.
4. The preparation method according to claim 1, wherein in the step b, the crosslinking agent is selected from one or more of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide, 1-cyclohexyl-2-morpholinoethylcarbodiimide and glutaraldehyde, and is preferably glutaraldehyde.
5. The method for preparing according to claim 1, wherein in step b, the covalent binding of deoxynivalenol DON antibody to BNM surface using cross-linking agent comprises:
the BNM is dispersed in PBS buffer solution, then is mixed with a cross-linking agent, and is centrifuged after the mixture is incubated to obtain BNM-g;
and mixing and reacting BNM-g with DON antibody solution, and covalently combining the DON antibody and BNM-g to obtain a BNM-DON antibody compound.
6. The preparation method according to claim 5, wherein the concentration of the DON antibody solution is 0.5 to 2 μ g/mL.
7. An electrochemical immunosensor prepared by the method according to any one of claims 1 to 6.
8. The use of the electrochemical immunosensor of claim 7 for the detection of deoxynivalenol.
9. Use according to claim 8, characterized in that it comprises the following steps:
s1, detecting electrochemical behavior of the electrochemical immunosensor: dripping a certain amount of DON antigen with different concentrations onto the electrochemical immunosensor to serve as a working electrode, forming a three-electrode measuring system with a reference electrode and an auxiliary electrode, and performing electrochemical measurement in a PBS (phosphate buffer solution) solution containing thionine and hydrogen peroxide by adopting a differential pulse voltammetry method to obtain a fitting linear regression equation and a detection limit of the electrochemical immunosensor to the DON;
s2, measurement of actual sample: and dripping the processed sample to be detected on the electrochemical immunosensor to serve as a working electrode, forming a three-electrode system with the reference electrode and the auxiliary electrode, carrying out electrochemical measurement, and calculating the concentration of the DON in the sample to be detected by utilizing a fitting linear regression equation of the electrochemical immunosensor to the DON.
10. The use according to claim 9, wherein in step S1, the concentration of DON antigen is 10 to 10 7 pg/mL；
And/or the reference electrode adopts a calomel electrode, and the auxiliary electrode adopts a platinum wire electrode.
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