CN114774106B - Aggregation-induced emission microsphere based on N-hydroxyethyl-1, 8-naphthalimide tetrastyrene derivative and application thereof - Google Patents
Aggregation-induced emission microsphere based on N-hydroxyethyl-1, 8-naphthalimide tetrastyrene derivative and application thereof Download PDFInfo
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Abstract
The invention discloses an aggregation-induced emission microsphere based on N-hydroxyethyl-1, 8-naphthalimide tetrastyrene derivatives and application thereof, and belongs to the field of analysis and detection. The aggregation-induced emission microsphere is prepared by using an N-hydroxyethyl-1, 8-naphthalimide tetrastyrene derivative as an AIE molecule through a swelling method, and is subsequently used for preparing an immunochromatographic test strip for quantitatively detecting the amino-terminal B brain natriuretic peptide, and the test strip structurally comprises the following components: PVC base plate, nitrocellulose membrane, conjugate pad, sample pad and absorbent pad. The anti-amino end B brain natriuretic peptide labeled antibody marked by aggregation-induced emission microsphere is sprayed on a bonding pad of an immunochromatographic test strip, a nitrocellulose membrane is provided with a detection area (T line) and a control area (C line), and a specific labeled antibody (coated antibody) and an anti-immunoglobulin G antibody (secondary antibody) are respectively sprayed. Compared with the traditional FITC fluorescent test strip, the sensitivity of the invention is improved by 14 times, and the invention has the advantages of simple and convenient operation, rapid quantification, convenient carrying, small sample dosage and the like.
Description
Technical Field
The invention belongs to the technical field of medical analysis and detection, and particularly relates to an aggregation-induced emission microsphere based on N-hydroxyethyl-1, 8-naphthalimide tetrastyrene derivatives, and a preparation method and application thereof.
Background
Brain natriuretic peptide (brain natriuretic peptide, BNP) is a hormone distributed in the heart, mainly acting in myocardial tissue. In addition, the measurement of BNP and the amino terminal brain natriuretic peptide precursor (NTERMINAL PRO-brain natriuretic peptide, NT-proBNP) can also be used as diagnostic biomarkers for acute and chronic heart failure. Since NT-proBNP is not easily degraded and has a long half-life, it can be used as a more ideal predictor. Therefore, the development of a rapid, simple and low-cost rapid detection method for quantitatively detecting NT-proBNP in real time has great significance for clinical diagnosis and later treatment determination schemes.
The immunochromatography technology is a detection method based on antigen-antibody specific reaction, has the advantages of high detection speed, good specificity, simple operation, low cost and the like, and can meet the requirements of on-site mass detection compared with other methods, so that the immunochromatography technology has rapid development in recent years and is widely applied to the fields of medical detection, food safety, environmental pollutant monitoring and the like. The traditional immunochromatography method has low sensitivity due to weak probe signal intensity, and cannot meet the requirements of high-sensitivity quantitative detection. The fluorescent probe has high signal intensity and stable luminescence, and is widely applied to the fields of in-vitro diagnosis, biological imaging and the like. The aggregation-induced emission microsphere is a novel fluorescent probe, and the bottleneck problem of concentration quenching of most traditional fluorescent dyes is solved due to the aggregation or solid-state fluorescence enhancement performance, so that the material becomes a popular research direction in recent years. In addition, AIE fluorescent nanoparticles are expected to be substitutes for fluorescent labeled probes due to the advantages of high luminescence, low toxicity, strong tissue penetrating power, light stability, biocompatibility and the like.
Disclosure of Invention
Aiming at the defects and the problems in the prior art, the invention aims to provide an aggregation-induced emission microsphere based on N-hydroxyethyl-1, 8-naphthalimide tetrastyrene derivatives, and a preparation method and application thereof.
The invention is realized by the following technical scheme:
In one aspect, the invention provides an aggregation-induced emission microsphere based on an N-hydroxyethyl-1, 8-naphthalimide tetrastyrene derivative, which is prepared by using N-2- (4- (tristyryl) -phenoxy) -ethyl) -4- (4- (tristyryl) -phenyl) -1, 8-naphthalimide as an AIE molecule and penetrating the AIE molecule into the polystyrene microsphere through a swelling method; the preparation method comprises the following steps:
(1) Dissolving N-2- (4- (tristyryl) -phenoxy) -ethyl) -4- (4- (tristyryl) -phenyl) -1, 8-naphthalimide as AIE molecules in tetrahydrofuran solution to obtain solution A;
(2) Dispersing polystyrene microspheres on the surface of carboxyl into a sodium dodecyl sulfonate aqueous solution to obtain solution B;
(3) Adding the solution A into acetone, uniformly mixing, adding the solution B while stirring, magnetically stirring at room temperature for 10-20h to evaporate acetone to a small amount, centrifuging to obtain a product, washing the product with ultrapure water, and suspending and dispersing the obtained fluorescent polystyrene nano-microspheres in the ultrapure water for standby.
Further, the AIE molecular structural formula in the step (1) is as follows:
the concentration of the solution A in the step (1) is 25mg/mL
The particle size of the polystyrene microsphere in the step (2) is 250-350nm;
In the step (3), the volume ratio of the liquid B to the acetone is 1:3;
the mass ratio of the polystyrene microsphere in the solution B to the AIE molecule in the solution A is 1:0.5-1.5.
The invention also provides application of the aggregation-induced emission microsphere based on the N-hydroxyethyl-1, 8-naphthalimide tetrastyrene derivative, and the aggregation-induced emission microsphere is used for preparing an immunochromatographic test strip for quantitatively detecting the amino terminal B brain natriuretic peptide.
Further, the immunochromatography test strip comprises a PVC bottom plate, a nitrocellulose membrane, a combination pad, a sample pad and a water absorption pad, wherein the combination pad is sprayed with a probe prepared from aggregation-induced emission microspheres based on N-2- (4- (tristyryl) -phenoxy) -ethyl) -4- (4- (tristyryl) -phenyl) -1, 8-naphthalimide; the nitrocellulose membrane is provided with a detection area and a control area, fluorescent strips are respectively arranged in the detection area and the control area, detection lines are arranged on the fluorescent strips of the detection area, the detection lines use coated antibodies, control lines are arranged on the fluorescent strips of the control area, and secondary antibodies are used on the control lines.
Specifically, the preparation method of the probe based on the aggregation-induced emission microsphere of N-2- (4- (tristyryl) -phenoxy) -ethyl) -4- (4- (tristyryl) -phenyl) -1, 8-naphthalimide comprises the following steps: adding aggregation-induced emission microsphere based on N-2- (4- (tristyryl) -phenoxy) -ethyl) -4- (4- (tristyryl) -phenyl) -1, 8-naphthalimide into PB buffer solution, adding labeled antibody, electrostatic adsorbing for 15min, adding EDC (p-ethyl-N, N-dimethylpropyl carbodiimide) to activate microsphere surface carboxyl, adding protein blocking agent to block carboxyl not combined with antibody on microsphere surface, incubating, centrifuging, discarding supernatant, and re-dissolving precipitate with complex solution to obtain probe
Further, the pH of the PB buffer solution in the probe preparation method is 5.5-8.0; the final concentration of the antibody after adding the antibody to be marked is 1-100 mug/mL, the final concentration of the antibody after adding the p-ethyl-N, N-dimethylpropyl carbodiimide is 0.01-1 mg/mL, the final concentration of the blocking agent after adding the blocking agent is 1.5-3%, and the blocking agent is selected from any one of casein, bovine serum albumin, ovalbumin and skimmed milk.
Further, the rotational speed of centrifugation in the probe preparation method is 12000-14000rpm, and the time is 10-30 min; the centrifuged precipitate is re-dissolved by AIE re-solution to 1/10 of the initial volume to prepare the probe, and the probe is preserved at 4 ℃ for standby.
Further, the nitrocellulose membrane of the immunochromatographic test strip is provided with a detection area and a control area, fluorescent strips are respectively arranged in the detection area and the control area, a detection line is arranged on the fluorescent strips of the detection area, a coated antibody is used as the detection line, a control line is arranged on the fluorescent strips of the control area, and a secondary antibody is used on the control line; the preparation method of the nitrocellulose membrane comprises the following steps:
1) The PB solution with the pH of between 0.01 and 0.5M and between 6.0 and 8.0 is used for respectively diluting the coated antibody, and the concentration of the secondary antibody is between 0.01 and 10.0mg/mL;
2) Spraying the coating antibody with the adjusted concentration on the upper part of the nitrocellulose membrane to serve as a detection line, and spraying the secondary antibody on the lower part of the nitrocellulose membrane to serve as a control line; the detection line and the control line are separated by a certain distance, and the film spraying amounts of the detection line and the control line are consistent and are 0.25-0.74 mu L/cm;
3) And (3) drying the nitrocellulose membrane sprayed with the detection line and the control line at 37 ℃ overnight, and then preserving the nitrocellulose membrane in a room temperature drying environment for standby.
Further, the assembly of the immunochromatographic test strip comprises the following steps:
1) A nitrocellulose membrane coated with antigens and secondary antibodies is stuck and sprayed on the middle area of the PVC bottom plate, a combining pad sprayed with a probe is stuck and sprayed on the lower end of the nitrocellulose membrane in a lap joint manner, a sample pad is stuck on the combining pad, and finally a water absorption pad is stuck on the upper end of the nitrocellulose membrane in a lap joint manner, so that the test paper strip plate can be assembled;
2) Cutting the assembled test strip plate into small test strips with the width of 390mm by a strip cutting instrument, and filling the test strip strips into a plastic card shell, namely the immunochromatography test strip for quantitatively detecting the amino terminal B brain natriuretic peptide based on the N-2- (4- (tristyryl) -phenoxy) -ethyl) -4- (4- (tristyryl) -phenyl) -1, 8-naphthalimide fluorescent microsphere used by the invention.
Further, the immunochromatographic test strip quantitatively detects the amino-terminal B brain natriuretic peptide as follows: the processed detection sample is added to an immunochromatography test strip prepared by taking aggregation-induced emission microspheres as a beacon carrier, the addition volume is 50-200 mu L, the reaction time is 5-30 min, the concentration of the detection sample is calculated by an embedded standard curve after the fluorescence data of the test strip are read, so that quantitative detection is realized, or whether fluorescence exists in a detection line and a control line is observed after the test strip is irradiated by flashlights with different wavelengths, so that qualitative judgment on the detection sample is realized.
Compared with the prior art, the method has the advantages that the AIE nanomaterial with high luminous intensity is used as a fluorescent marker to prepare the signal probe, and a high-sensitivity aggregation-induced emission fluorescent immunoassay method is established.
Drawings
FIG. 1 is a schematic diagram of an immunochromatographic test strip according to the present invention;
FIG. 2 is a schematic diagram of the sandwich fluorescence immunochromatography test strip detection of the present invention;
FIG. 3 is an SEM image of a polystyrene fluorescent microsphere synthesized according to the present invention;
FIG. 4 shows NT-proBNP standard curve.
Illustration of: 1-PVC bottom plate, 2-sample pad, 3-binding pad, 4-nitrocellulose membrane, 5-detection zone, 6-control zone, 7-absorbent pad, 8-labeled probe, 9-coated antibody, 10-secondary antibody.
Detailed Description
The invention will be further described with reference to the accompanying drawings.
Hereinafter, embodiments of the present invention will be described in detail. In order to avoid unnecessary detail, well-known structures or functions will not be described in detail in the following embodiments.
Unless defined otherwise, technical and scientific terms used in the following examples have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
The test reagent consumables used in the following examples are all conventional biochemical reagents unless otherwise specified; the experimental methods are conventional methods unless otherwise specified.
Example 1 preparation of aggregation-induced emission microspheres
Dissolving N-2- (4- (tristyryl) -phenoxy) -ethyl) -4- (4- (tristyryl) -phenyl) -1, 8-naphthalimide serving as AIE molecules in tetrahydrofuran solution to obtain solution A, dispersing polystyrene microspheres on the surface of carboxyl into sodium dodecyl sulfonate aqueous solution to obtain solution B, adding the solution A into acetone to mix uniformly, adding the solution B while stirring, magnetically stirring for 10-20h at room temperature to evaporate acetone to a small amount, centrifuging to obtain a product, washing the product with ultrapure water, and suspending and dispersing the obtained fluorescent polystyrene nano-microspheres (namely aggregation-induced light-emitting microspheres based on N-2- (4- (tristyryl) -phenoxy) -ethyl) -4- (4- (tristyryl) -phenyl) -1, 8-naphthalimide) in ultrapure water for later use, wherein the SEM of the microspheres is shown in figure 3.
Example 2 preparation and application of immunochromatographic test strip
1. Preparation of nitrocellulose membranes
NT-proBNP coated antibody was coated on nitrocellulose membrane: diluting the NT-proBNP coated antibody with PB 6.5 to a concentration of 1.8mg/mL, and spraying the obtained solution on a film to serve as a detection line; the concentration of the diluted secondary antibody is 1mg/mL, the obtained solution is sprayed on a film to be used as a control line, the spraying amount of the two lines is 0.74 mu L/cm, the distance between the detection line and the top edge of the film is 10mm, the distance between the detection line and the top edge of the film is 5mm, the drying is carried out for 12 hours at 37 ℃, and the obtained solution is placed in a drying cabinet to be stored for standby.
2. Preparation of bond pads
Adding 10 mu g of AIE fluorescent microsphere into 500 mu L of PB 6.5 buffer solution, then adding 2 mu g of labeled antibody, carrying out electrostatic adsorption for 15min, then adding 4ug of EDC to activate the carboxyl on the surface of the microsphere, incubating for 30min, repeating for 3 times, then adding 1.5% casein to seal the carboxyl on the surface of the microsphere which is not combined with the antibody, incubating for 1h, centrifuging for 15min at 12000r, discarding supernatant, re-dissolving the precipitate with 100 mu L of AIE re-solution, and preparing a probe for later use; spraying onto the bond according to the volume of 3 mu L/cm, and vacuum drying for 2h for later use.
3. Assembling a test strip:
sequentially pasting a PVC bottom plate, a nitrocellulose membrane, a binding pad, a sample pad and a water absorption pad according to a test strip structure schematic diagram, namely pasting and spraying the nitrocellulose membrane coated with antigens and secondary antibodies on the middle area of the PVC bottom plate, pasting and spraying the binding pad of a probe on the lower end of the PVC bottom plate, pasting the sample pad on the binding pad again, pasting and adhering the water absorption pad on the upper end of the binding pad, cutting 390 mm test strips by using a cutter after assembly, loading the test strips into a plastic clamping shell, packing into an aluminum foil bag after compaction, adding a drying agent, sealing and preserving, and keeping the room temperature environment for 12 months.
The structure of the prepared immunochromatography test strip is shown in figure 1, a PVC bottom plate 1, a nitrocellulose membrane 4, a bonding pad 3, a sample pad 2 and a water absorption pad 7 are sequentially overlapped on the PVC bottom plate 1 from left to right, and the sample pad 2, the bonding pad 3, the nitrocellulose membrane 4 and the water absorption pad 7 are sequentially overlapped on the PVC bottom plate 1; the conjugate pad 3 contains a labeled antibody 8 to procalcitonin that is labeled with N-2- (4- (tristyryl) -phenoxy) -ethyl) -4- (4- (tristyryl) -phenyl) -1, 8-naphthalimide; the fluorescent polystyrene nano-microsphere permeates AIE into the polystyrene microsphere by a swelling method; the nitrocellulose membrane 4 is provided with a detection area and a control area, fluorescent strips are respectively arranged in the detection area and the control area, detection lines 5 are arranged on the fluorescent strips of the detection area 5, and the detection lines 5 use coated antibodies 9; the fluorescent strip of the control area is provided with a control line 6, and the control line 6 is provided with a secondary antibody 10.
The immunochromatography test strip prepared by the method is used for quantitatively detecting the B brain natriuretic peptide at the tail end of the amino, the detection principle is shown in figure 2, and when a sample does not contain a macromolecular analyte, the probes on the binding pad 3 surge to a control area along with the sample to form a single bright signal strip; when the detection analyte is present in the sample, the probes on the conjugate pad 3 capture the target analyte, are captured by the antibody when rushing to the T line (detection line 5), and the remaining probes continue to rushing to the control zone to be captured by the C line (control line 6), thus forming a bright double-line signal strip; the concentration of the analyte in the sample can be quantitatively judged according to the intensity of the detection line signal strip.
4. Quantitative determination of NT-proBNP in serum
(1) Drawing a standard curve:
Labeling the negative matrix, wherein the concentration of NT-proBNP in the standard curve is as follows: 0. 0.24, 0.48, 0.97, 1.95, 3.91, 7.81, 15.62, 31.25ng/mL, R 2 is calculated as 0.9906, and the linear regression equation is: y=0.0675x+0.1161. The standard NT-proBNP standard curve is shown in FIG. 4.
(2) Quantitative determination of NT-proBNP in serum
And adding 70 mu L of diluted 1000-fold serum sample into the test strip sample adding hole, reacting for 15min, inserting the test strip into a detection window of a fluorescence reader, displaying fluorescence values of a detection line and a control line on a display, and calculating the content of NT-proBNP in the sample according to a standard curve recorded in the instrument to realize quantitative detection of a positive sample.
The foregoing description of the preferred embodiments of the present invention has been presented only in terms of those specific and detailed descriptions, and is not, therefore, to be construed as limiting the scope of the invention. It should be noted that modifications, improvements and substitutions can be made by those skilled in the art without departing from the spirit of the invention, which are all within the scope of the invention. Accordingly, the scope of protection of the present invention is to be determined by the appended claims.
Claims (5)
1. Aggregation-induced emission microsphere based on N-hydroxyethyl-1, 8-naphthalimide tetrastyrene derivative, characterized in that: the aggregation-induced emission microsphere is prepared by taking N-2- (4- (tristyryl) -phenoxy) -ethyl) -4- (4- (tristyryl) -phenyl) -1, 8-naphthalimide as AIE molecules and penetrating the AIE molecules into polystyrene microspheres through a swelling method; the AIE molecular structural formula is as follows:
。
2. Aggregation-induced emission microsphere based on an N-hydroxyethyl-1, 8-naphthalimide tetrastyrene derivative according to claim 1, characterized in that: the particle size of the polystyrene microsphere is 250-350 nm.
3. Use of aggregation-induced emission microspheres based on N-hydroxyethyl-1, 8-naphthalimide tetrastyrene derivatives according to claim 1 or 2, characterized in that: the aggregation-induced emission microsphere is used for preparing an immunochromatographic test strip for quantitatively detecting the amino-terminal B brain natriuretic peptide.
4. A use according to claim 3, characterized in that: the immunochromatography test strip comprises a PVC bottom plate, a nitrocellulose membrane, a combination pad, a sample pad and a water absorption pad, wherein the combination pad is sprayed with a probe prepared from aggregation-induced emission microspheres based on N-2- (4- (tristyryl) -phenoxy) -ethyl) -4- (4- (tristyryl) -phenyl) -1, 8-naphthalimide; the nitrocellulose membrane is provided with a detection area and a control area, fluorescent strips are respectively arranged in the detection area and the control area, detection lines are arranged on the fluorescent strips of the detection area, the detection lines use coated antibodies, control lines are arranged on the fluorescent strips of the control area, and secondary antibodies are used on the control lines.
5. The use according to claim 4, wherein the immunochromatographic test strip quantitatively detects the amino-terminal B brain natriuretic peptide as follows: the processed detection sample is added to an immunochromatography test strip prepared by taking aggregation-induced emission microspheres as a beacon carrier, the added volume is 50-200 mu L, the reaction time is 5-30 min, the concentration of the detection sample is calculated by an internal standard curve after the fluorescence data of the test strip are read, the quantitative detection is realized, or the qualitative judgment of the detection sample is realized by observing whether the detection line and the control line are fluorescent or not after the test strip is irradiated by flashlights with different wavelengths.
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| CN204287206U (en) * | 2014-10-28 | 2015-04-22 | 广州天宝颂原生物科技开发有限公司 | NT-proBNP precursor immunochromatographiassay assay quantitative detection test paper |
| CN107602469A (en) * | 2017-10-30 | 2018-01-19 | 江西科技师范大学 | It is a kind of that there is aggregation-induced emission enhancement, the naphthalimide compound of solvent discoloration and self- recoverage power mutagens color property and application |
| CN111983243A (en) * | 2020-08-10 | 2020-11-24 | 深圳市宇诺生物技术有限公司 | Amino-terminal brain natriuretic peptide precursor determination kit, preparation method and detection method |
| CN113683717A (en) * | 2021-10-13 | 2021-11-23 | 广东省大湾区华南理工大学聚集诱导发光高等研究院 | Micron-sized aggregation-induced emission polymer microsphere and preparation method and application thereof |
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| CN204287206U (en) * | 2014-10-28 | 2015-04-22 | 广州天宝颂原生物科技开发有限公司 | NT-proBNP precursor immunochromatographiassay assay quantitative detection test paper |
| CN107602469A (en) * | 2017-10-30 | 2018-01-19 | 江西科技师范大学 | It is a kind of that there is aggregation-induced emission enhancement, the naphthalimide compound of solvent discoloration and self- recoverage power mutagens color property and application |
| CN111983243A (en) * | 2020-08-10 | 2020-11-24 | 深圳市宇诺生物技术有限公司 | Amino-terminal brain natriuretic peptide precursor determination kit, preparation method and detection method |
| CN113683717A (en) * | 2021-10-13 | 2021-11-23 | 广东省大湾区华南理工大学聚集诱导发光高等研究院 | Micron-sized aggregation-induced emission polymer microsphere and preparation method and application thereof |
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