CN110702647A - Construction and application of novel fluorescent imprinting sensor based on magnetic Metal Organic Framework (MOF) - Google Patents
Construction and application of novel fluorescent imprinting sensor based on magnetic Metal Organic Framework (MOF) Download PDFInfo
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Abstract
The invention reports the preparation of a novel fluorescent imprinted polymer sensor based on a magnetic Metal Organic Framework (MOF) and successfully uses the sensor for detecting Hepatitis A Virus (HAV). In the present invention, we introduced luminescent MOF (MIL-101-NH)2) Instead of quantum dots and organic dyes as output signals. The light-emitting MOF material can be used not only as an output signal, but also as a carrier. Meanwhile, the metal organic framework has a larger specific surface area, so that more imprinting sites can be provided, and the response sensitivity of the sensor is improved; ferroferric oxide particles and MIL-101-NH2The combination of materials ensures that the process for preparing the imprinted polymer is simpler and fasterSpeed; the fluorescence analysis method has the advantages of high sensitivity, strong selectivity, convenient operation and the like. Therefore, by combining the advantages, compared with other analysis methods or sensors, the molecular imprinting fluorescence chemical sensor constructed by the invention has good selectivity on template molecules and high detection sensitivity. The result shows that the method is simple, convenient and rapid, can be used for qualitatively and quantitatively detecting HAV, and has important practical application potential and significance in the aspects of biosensing and virus detection and prevention.
Description
Technical Field
The invention belongs to the technical field of analytical chemistry detection, and particularly relates to construction and application of a novel fluorescent imprinted sensor based on a magnetic metal organic framework.
Background
In the preparation of the traditional fluorescent virus molecular imprinting material, researchers often introduce fluorescent materials, such as quantum dots [ Zhou j., Yang y., Zhang c., Chemical reviews,2015,115,11669-11717 ], organic fluorescent dyes and the like, into the imprinting layer as output signals, or directly utilize the fluorescence of the virus itself as the output signals, and these works have achieved certain results. However, in our subsequent studies, it was found that imprinted polymers with quantum dots would exhibit fluorescence instability; imprinted polymers containing organic fluorescent dyes have the potential for photobleaching, and most organic dyes are slightly toxic and are not suitable for further application in vivo studies. The detection by using the fluorescence of the virus avoids the problems, but the obtained detection range and detection limit are not ideal due to the weak fluorescence intensity.
A Metal Organic Framework (MOF) is an organic-inorganic hybrid material with intramolecular pores formed by self-assembly of organic ligands and metal ions or clusters through coordination bonds. These materials have properties of high pore volume, highly ordered pore structure, high active site density and high specific surface area [ Reed d.a., Keitz b.k., Oktawiec j., Nature,2017,550,96.]. More and more people use functional MOFs materials to sense inorganic ions and small organic molecules. Of these materials, the class of MOFs that fluoresce due to their own chromophores (e.g., MIL-101-NH)2UIO-66, etc.) have attracted attention. The inherent photophysical properties and porosity of these light-emitting MOFs can satisfy the packaging capability of objects, and are expected to be applied to fluorescence sensing.
Thus, in this study, we used luminescent MOFs (MIL-101-NH)2) Instead of the fluorescent signal source described above as the output signal. It is worth mentioning that MIL-101-NH2The fluorescent material not only can be used as a fluorescent output signal, but also can be used as a print carrier, and utilizes the advantages of large specific surface area, excellent stability and the like of MOFs materials. In the present invention HAV Magnetic Molecularly Imprinted Polymers (MMIPs) are synthesized by a simple one-step process. The specific procedures are as follows: firstly, magnetic MIL-101-NH is synthesized2Then fixing template virus HAV on the surface, adding TEOS to crosslink and polymerize to obtainAn imprinted polymer. The method has the advantages of quick and simple preparation process and low cost, and obtains expected effects in application.
Disclosure of Invention
The invention aims to provide a novel method for detecting hepatitis A virus by using a magnetic metal organic framework-based molecularly imprinted fluorescent sensor, and the sensor is applied to specific recognition and detection of virus molecules.
The purpose of the invention is realized by the following technical scheme.
The construction and application of the novel molecularly imprinted fluorescent sensor based on the amino functionalized metal organic framework are characterized by comprising the following process steps:
(1) preparation of the magnetic metal organic framework fluorescent molecularly imprinted polymer based on amino functionalization: firstly, ferroferric oxide is carboxylated, and then MIL-101-NH is prepared on the surface of the ferroferric oxide2(ii) a HAV imprinted polymer, which was molecularly imprinted polymer immobilized on MOFs Material (MIL-101-NH), was prepared by using the above particles as a carrier, HAV as a template and TEOS as a cross-linker2) On the surface of (a);
(2) ferroferric oxide particles and MIL-101-NH2The combined action of the materials: the target viruses are better fixed and imprinted by utilizing the properties of the MOFs material such as high pore volume, high specific surface area and the like, and the process of preparing the imprinted polymer is simpler and quicker under the action of a magnet;
(3) the construction and application of the virus fluorescent molecular imprinting sensor are as follows: adsorbing template molecules and imprinted polymers for a period of time under optimized experimental conditions, taking a mixture of the template molecules and the imprinted polymers in a cuvette, exciting under the conditions that the wavelength is 290nm and the slit is 5.0nm-5.0nm, measuring the fluorescence intensity of the mixture by using an RF-5301PC fluorescence spectrophotometer, and constructing the metal organic framework fluorescence molecular imprinting sensor based on amino functionalization, wherein the emission wavelength is 420 nm.
Compared with the prior art, the invention has the following beneficial effects:
(1) introducing luminous MOFs (MIL-101-NH)2) As output signal instead of quantum dots and organic dyesIt has stable fluorescence signal, no photobleaching property, no toxicity and other features. The luminous MOFs material can be used as an output signal, can also be used as a carrier, and has the advantages of the MOFs material.
(2) The magnetic nano-particle is taken as a substrate, and a layer of metal organic framework material is grafted on the surface of the magnetic nano-particle to be taken as a carrier material for virus molecular imprinting. The magnetic property of the imprinted polymer is utilized for elution and purification, so that the preparation process of the imprinted polymer is simpler and faster; the surface of the metal organic framework material is easy to modify, the specific surface area is large, and more binding sites can be provided; and the thermal stability is good, thus being beneficial to long-term storage and use.
(3) The experimental result shows that the virus molecular imprinting fluorescence sensor has high selectivity and sensitivity to target molecules and satisfactory imprinting effect;
(4) the sensor has the potential possibility of being applied to other molecule detection, and the detection process has low professional requirements on operators, so that the sensor has important practical application value.
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FIG. 1 is a flow chart of the preparation of the virus molecular imprinting fluorescence sensor
[ FIG. 2 ]]Fe3O4(a)、Fe3O4@SiO2(b)、Fe3O4@ MOFs (c) and Fe3O4@ MOFs @ MIPs (d) infrared spectrogram of particles.
[ FIG. 3 ]]Fe3O4@SiO2-COOH (a) and Fe3O4@ MOFs (b) X-ray diffraction pattern of the particles.
[ FIG. 4 ]]Fe3O4@SiO2(a)，Fe3O4@ MOFs @ MIPs (b) SEM image of particles.
FIG. 5 response graph of viral molecularly imprinted fluorescent sensors to different concentrations of HAV:
FIG. 6 is a diagram of the detection of different viruses by a virus molecularly imprinted fluorescent sensor.
FIG. 7 viral molecularly imprinted fluorescent sensors were used for labeling recovery of HAV.
Detailed description of the preferred embodiments
Embodiments of the present invention will now be described in further detail with reference to the accompanying drawings and examples. The following examples are intended to illustrate the invention without limiting its scope of application and its extension.
Example 1: preparation method of novel virus fluorescent molecular imprinting sensor
(1)Fe3O4@MIL-101-NH2The synthesis of (2): first, carboxyl-functionalized ferroferric oxide particles, 1gFe, were prepared3O4100mL of isopropanol and 4mL of ultrapure water are subjected to ultrasonic treatment for 20min and then are uniformly dispersed. With mechanical stirring, 20mL of ammonia was added, 6mL of TEOS was added dropwise, and the reaction was carried out in an oil bath at 45 ℃ for 6 h. Finally washing with distilled water and ethanol, and vacuum drying at 60 deg.C to obtain Fe3O4@SiO2The product is ready for use. 0.5g Succinic Anhydride (SA) and 1mL 3-Aminopropyltriethoxysilane (APTES) were dissolved in 30mL acetic acid, sonicated for 5min, and stirred at 30 ℃ for 3 h. Then 40mg of Fe was added3O4@SiO2Particles, 20mL of acetic acid and 3mL of ultrapure water, and the mixture was dispersed with ultrasound and then reacted extensively in an oil bath at 30 ℃ for 12 h. After washing with water, it was dried under vacuum.
(2)Fe3O4Preparation of @ MOF: taking 0.8g Cr (NO)3)3·9H2O，0.36g H2BDC-NH20.16g NaOH, dissolved in 15mL of ultrapure water and stirred at room temperature for 1.5 h. After mixing, 30mg Fe was added3O4@SiO2-COOH, stirred for 30min and transferred to a 50mL reaction vessel. The reaction is carried out at 150 ℃ for 12h to obtain Fe3O4@ MOF, used after drying.
(3) Preparation of magnetic molecularly imprinted polymer/non-imprinted polymer (MMIPs/MNIPs) particles: 2mL of HAV solution, 0.06g of Fe3O4@ MOF, ultrasonically dispersed in 15% tetrahydrofuran, after 30min, 50. mu.L TEOS was added and the reaction was held at 30 ℃ for 12 h. The product was separated from the reaction solution by a magnet, and then the unreacted monomer, the non-imprinted template, the oligomer and the like in the reaction solution were washed away with ultrapure water.Using methanol: the template was eluted with acetic acid (9: 1, v: v), and the remaining eluate was washed off with ultrapure water and dried under vacuum. Non-imprinted particles (NIPs) were synthesized in the absence of template virus under the same conditions and processed in the same elution step.
(4) Construction of the molecularly imprinted fluorescent sensors (MMIPs sensors): MMIPs particles were dispersed in PBS dilution to a final concentration of 19. mu.g/mL. HAV was added and mixed, and the solution volume was adjusted to 1000. mu.L with PBS buffer and shaken for a period of time at a constant temperature. Then a certain amount of reaction liquid is taken to be placed in a cuvette, and fluorescence of the cuvette is measured by adopting an RF-5301PC fluorescence spectrophotometer to construct the molecular imprinting fluorescence sensor for detecting the virus. The detection conditions are as follows: excitation wavelength: 290nm, emission wavelength: 420nm, excitation slit: 5.0nm, emission slit: 5.0 nm.
Example 2: and the performance, the appearance and the structure of the MMIPs fluorescence sensor and the intermediate product are characterized.
All the prepared materials are characterized in structure and appearance by a Fourier transform infrared spectrometer, an X-ray diffractometer and a scanning electron microscope. FIG. 2 is Fe3O4(a)，Fe3O4@SiO2(b)，Fe3O4@ MOFs (c) and Fe3O4@ MOFs @ MIPs (d) infrared spectrogram of particles. About 570cm-1The absorption peak at (A) is due to Fe3O4Characteristic peak of Fe-O. 1096cm-1The absorption peak at (A) is the tensile vibration peak of Si-O-Si, 793cm-1The absorption peak at (A) is the oscillation peak of Si-O. This is Fe3O4@SiO2The synthesis of (a) provides evidence. The resulting lines all contain these characteristic peaks. After synthesis of MOF, the infrared spectrum was changed again. 1384cm-1,1500cm-1And 1628cm-1The three absorption peaks in (B) are represented in Fe3O4To form MIL-101-NH2。
FIG. 3 is Fe3O4@SiO2(a) MMIPs (b) SEM pictures of the particles. As can be seen in FIG. 3a, the coating is SiO2Fe (b) of3O4Is relatively smooth and has a uniform spherical shape of about 300 nm. FIG. 3b shows a toolImages of MMIPs particles with rough surfaces and aggregated particles with a particle size of about 500 nm.
Further analysis of Fe by X-ray diffraction (FIG. 4)3O4@SiO2-COOH and Fe3O4@ MOFs. FIG. 4 is Fe3O4@SiO2-COOH and Fe3O4The XRD spectrum of @ MOF. As shown in fig. 4a, several characteristic peaks of iron oxide (30.1 °, 43.1 °, 53.4 °, 57 °, 62.6 °) in the range of 20 ° to 80 ° (2 θ) were observed in both samples, and these weaker characteristic peaks may be caused by the silicon layer coating. FIG. 4b is Fe3O4XRD spectra of @ MOF, Fe compared to FIG. 4a3O4Almost disappeared, demonstrating that the MOFs layer was successfully prepared.
Example 3: application of fluorescent molecular imprinting sensor
The experimental conditions of this example were: the amount of MMIPs was 22.44mg/mL, the pH was 7.5, the adsorption time was 15min, and the temperature was 37 ℃. The specific implementation scheme is as follows: the pH of the whole system was adjusted to 7.5 by taking HAV and MMIP at specific concentrations in a PB buffer of 19. mu.g/mL, and the fluorescence intensity was measured after adsorbing at 37 ℃ for 15min with shaking.
(1) Detection and analysis of different concentrations of HAV by MMIPs fluorescence sensor
Under the optimal experimental environment, the linear relation between the fluorescence intensity and the concentration of the template virus is researched. As shown in FIG. 5, the fluorescence intensity has a good linear relationship with the concentration of the template virus when the concentration of the template virus is in the range of 20pM to 2500 pM. The linear regression equation is that y is 251.53x +175.92, R20.997, y is fluorescence intensity, and x is template virus concentration (nM). As the concentration of template virus increases, the fluorescence intensity also increases due to the specific adsorption of the imprinted particles to the template virus. The detection limit was then calculated based on a 3-fold signal-to-noise ratio (S/N-3), with a detection limit of 3 pM.
(2) Selective adsorption of HAV by MMIPs fluorescence sensors
In this example, HAV, JEV, HBV and RV at concentrations of 1.0nM were selected as targets to examine the HAV adsorption and detection ability of MMIPS fluorescence sensors. The experiment was performed as described above, repeated three times and averaged. The latter three competitors have similar properties to the template virus hepatitis A, but differ in particle size, etc. The results are shown in fig. 6. The imprinted particles respond most strongly to HAV under the same optimal experimental conditions. The response of JEV to imprinted particles is significantly lower than HAV, probably because the particle size of JEV is much larger than that of HAV and therefore the imprinted sites do not match. The fluorescence response of HBV is also lower than that of HAV because both belong to the same genus, but differ in surface composition and particle size. This demonstrates the specificity of the imprinted polymer for adsorption of the template virus.
(3) Spiking recovery of HAV by MMIPS fluorescence sensors
To evaluate the recognition ability of imprinted polymers in real samples, experimental references, serum was diluted and spiked recovery experiments were performed under optimal experimental conditions. Each sample was measured in triplicate and recovery was calculated using a linear regression equation. The results are shown in fig. 7. The recovery was between 90% and 106%, indicating that the method can be used to determine HAV dose in human diluted serum.
Claims (4)
1. The construction and application of a novel fluorescent imprinting sensor based on a magnetic Metal Organic Framework (MOF) are characterized in that: immobilization of molecularly imprinted polymers on luminescent MOF materials (MIL-101-NH)2) On the surface of (a). Firstly, ferroferric oxide is carboxylated, and then MIL-101-NH is prepared on the surface of the ferroferric oxide2(ii) a HAV imprinted polymers were prepared using the above particles as a carrier, Hepatitis A Virus (HAV) as a template and TEOS as a cross-linker. And the metal organic framework molecularly imprinted fluorescent sensor is constructed as a metal organic framework molecularly imprinted fluorescent sensor based on amino functionalization and used for detecting target viruses. The method specifically comprises the following points:
1) magnetic nano particles are used as carriers, and then MIL-101-NH is prepared on the surfaces of the magnetic nano particles2(ii) a Preparation of virus imprinted polymers by using the above particles as carriers and TEOS as a cross-linker. Elution is carried out under the action of a magnet, the elution time is shortened, and the elution process is simpler and faster.
2) And (3) constructing the virus molecular imprinting fluorescence sensor.
3) The virus molecular imprinting fluorescence sensor is applied.
2. The method of preparing imprinted polymer according to claim 1), which comprises the following steps:
1) firstly, synthesizing carboxyl functionalized magnetic nano particles, and preparing MIL-101-NH on the surface of the carboxyl functionalized magnetic nano particles2And the compound is used as a carrier material in imprinting;
2) adding a functional monomer, a cross-linking agent and a template virus HAV on the basis of 1), and eluting the template after polymerization is completed to obtain the HAV imprinted polymer.
3) The method for preparing the virus molecularly imprinted polymer according to claim 1, wherein the magnetic nanoparticles are used as carriers, and the magnetic nanoparticles are separated by magnetic elution to achieve the purpose of simplicity and rapidness. And growing a layer of MOF material on the surface of the magnet to increase the specific surface area of the MOF material.
3. The method of claim 1, point 2), wherein the method comprises the following steps: and (3) taking a proper amount of imprinted polymer into a buffer solution, adding a proper amount of virus, and oscillating and adsorbing under an optimized adsorption condition. Then, a certain amount of the mixture is put into a cuvette, and the fluorescence intensity is measured by an RF-5301PC fluorescence spectrophotometer to construct a novel virus molecular imprinting fluorescence sensor. The detection conditions are as follows: the excitation wavelength was 290nm, the emission wavelength was 420nm, and the slit widths for excitation and emission were 5.0nm and 5.0nm, respectively.
4. The use of a viral molecularly imprinted fluorescent sensor according to claim 1, point 3), characterized in that: analyzing HAV with different concentrations by using the virus molecular imprinting fluorescence sensor to evaluate the detection range and detection limit of the virus on the template; detecting different virus molecules with the same concentration by using the virus molecular imprinting fluorescence sensor to evaluate the selective recognition and detection capability of the prepared molecular imprinting sensor on template molecules; the intelligent virus molecular imprinting fluorescence sensor is applied to the labeling recovery of HAV in human serum, and is used for evaluating the actual analysis capability of the molecular imprinting sensor on template molecules.
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| CN113072711A (en) * | 2021-03-29 | 2021-07-06 | 佛山湘潭大学绿色智造研究院 | Magnetic and photon-based dual-response virus molecularly imprinted sensor and construction method thereof |
| CN114384064A (en) * | 2021-12-08 | 2022-04-22 | 江苏大学 | Method for high-sensitivity rapid detection of pesticide residues based on imprinted MOFs probe |
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