A surface-modified compound and its preparation method

Abstract

The present invention discloses a surface modification compound and a preparation method thereof. The chemical structure of the surface modification compound is shown in formula (I): #imgabs0#, wherein R1 is selected from, or; R2 is selected from H2 or CH3. The preparation process of the present invention has fewer synthesis steps, high synthesis yield, and simple purification. Through this preparation process, the property of quartz, PMMA, PDMS and other materials that cannot be grafted with proteins can be changed, which expands the range of selectable surface modification compounds and broadens the range of materials that can be used in the SimpleWestern method.

Description

Technical Field

[0001] The present invention relates to the technical field of surface modification compound preparation, in particular to a surface modification compound and a preparation method thereof. Background Art

[0002] Western Blot method is a kind of labor-intensive laboratory analysis method, and it is widely used in the life science to determine whether there is target protein and to determine the relative amount of target protein in complex samples.Owing to needing to use protein amount larger, complicated operation, reagent consumption is large, consuming time length etc. deficiency makes its application limited, especially has obvious deficiency for the research of trace level expression protein.So, Western Blot technology has developed multiple different implementation methods, and wherein Simple Western is a kind of simple and practical method, and it is generally used for studying the expression level of trace protein, and its advantage is simple, fast, with low cost and scalability.In addition, owing to not needing to use complicated chemiluminescence or fluorescence detection method, Simple Western is applicable to studying the expression level of trace protein, particularly for those protein samples that are difficult to prepare a large amount of standard products.

[0003] Surface grafting modification can improve the properties of different materials by modifying and grafting different coupling agents onto their surfaces, thereby expanding their functionality to varying degrees. Applying this modification approach to different materials allows for the application of Simple Western spectroscopy on materials with varying properties, significantly expanding its scope and having significant implications for the implementation of Simple Western spectroscopy on diverse materials.

[0004] Benzophenone, a commonly used photosensitizer, generates highly reactive free radical intermediates when excited by light of a specific wavelength (generally ultraviolet light around 365 nm). These intermediates can rapidly form covalent bonds with surrounding components, such as amino acids in proteins. The reaction equation is shown below. By combining this property, surface-modified compounds can be prepared, making it possible to fix proteins on surfaces that otherwise would not be suitable.

[0005] Summary of the Invention

[0006] To overcome the shortcomings and deficiencies of existing technologies, the present invention provides a surface-modified compound and its preparation method. This invention modifies the surface of a variety of commonly used materials, such as quartz, PMMA, and PDMS, allowing the surfaces to react with the novel surface-modified compound, forming stable chemical bonds. This allows the material to be capable of protein grafting, a capability not previously possible. The synthesis process for this novel surface-modified compound offers advantages such as simple synthesis, high yield, effective grafting, and low cost. This provides more options and grafting strategies for subsequent material modification, expands the synthesis of surface-modified materials, and offers a wider range of surface-modified compounds to choose from.

[0007] The purpose of the present invention is achieved through the following technical solutions:

[0008] In a first aspect, the present invention provides a surface-modified compound, characterized in that the chemical structure is as shown in formula (I):

[0009]

[0010] Wherein, R1 is selected from

[0011]

[0012] R2 is selected from H2 or CH3.

[0013] Furthermore, the surface-modified compound is represented by formula (II), formula (III) or formula (IV):

[0014]

[0015] In a second aspect, the present invention provides a modified quartz plate, which is formed by grafting a pretreated quartz plate with a surface modification compound, and the chemical structure of the surface modification compound is as shown in formula (II) described in the first aspect.

[0016] In a third aspect, the present invention provides a method for preparing the modified quartz plate according to the second aspect, wherein the preparation steps are as follows:

[0017] 1) Pre-treating the quartz plate;

[0018] 2) Grafting 3-aminopropyltrimethoxysilane onto a quartz plate: Prepare a mixed solution of 3-aminopropyltrimethoxysilane and methanol, add the solution to a square Petri dish, soak the quartz plate in the mixed solution, place the square Petri dish in an oven for reaction, rinse with methanol, and finally dry with nitrogen for later use.

[0019] 3) Connecting 3-(bromomethyl)benzophenone to 3-aminopropyltrimethoxysilane: Dissolve 3-(bromomethyl)benzophenone and potassium carbonate powder in DMF, and form a mixed solution after sonication in the dark. Then, immerse the quartz plate treated in step 2) in the mixed solution, react at room temperature, and after connection, rinse with DMF, then rinse with PBST, and finally blow dry with nitrogen to obtain a modified quartz plate.

[0020] Furthermore, in step 1), the pretreatment refers to sequentially flushing the quartz plate with a 0.1 mol / L HCl solution for 30 min, then flushing with deionized water for 10 min, and then flushing the quartz plate with a 0.1 mol / L NaOH solution for 2 h, then flushing with methanol for 10 min, and finally drying with nitrogen.

[0021] Furthermore, in step 2), the reaction time is 12-16 hours.

[0022] The synthetic route of the modified quartz plate is:

[0023]

[0024] The present invention also provides another method for preparing the modified quartz plate as described in the second aspect, and the preparation steps are as follows:

[0025] 1) Synthesis of pheny l(3-(((3-(trimethoxysilyl)propy l)amino)methy l)phenyl)-methanone (surface-modified compound (II)): 3-aminopropyltrimethoxysilane (APS), 3-(bromomethyl)benzophenone, and potassium carbonate were dissolved in DMF, protected from light, and reacted at room temperature to precipitate a white solid. The solid was filtered, dried with water, rinsed with methanol, and dried to obtain surface-modified compound (II).

[0026] 2) Pre-treating the quartz plate;

[0027] 3) Connecting the surface modification compound (II) to the treated quartz plate: Prepare a mixed solution of the surface modification compound (II) and DMF, add the solution to a square culture dish, then immerse the quartz plate in the mixed solution until it is completely covered by the mixed solution, then place the square culture dish in an oven for reaction, rinse after connection is completed, and finally blow dry with nitrogen to obtain a modified quartz plate.

[0028] Furthermore, in step 2), the pretreatment refers to sequentially washing the quartz plate with a 0.1 mol / L HCl solution in a circulation manner for 30 min, then washing with deionized water for 10 min, washing the quartz plate with a 0.1 mol / L NaOH solution in a circulation manner for 2 h, then washing with methanol for 10 min, and finally drying with nitrogen.

[0029] Another synthetic route of the modified quartz plate is:

[0030]

[0031] In a fourth aspect, the present invention provides a modified PDMS plate, which is formed by grafting a surface modification compound onto a hydrosilanized PDMS plate, wherein the chemical structure of the surface modification compound is as shown in formula (III) described in the first aspect.

[0032] In a fifth aspect, the present invention provides a method for preparing the modified PDMS plate according to the fourth aspect, wherein the preparation steps are as follows:

[0033] 1) Synthesis of pent-4-en-1-yl 2-(3-benzoyl phenyl)propanoate (surface-modified compound (III)): Ketoprofen and 4-penten-1-ol were dissolved in DMF, DMAP was added and stirred, and then EDC 1 was added. The mixture was reacted and extracted at room temperature. The mixture was spin-dried and purified to obtain surface-modified compound (III).

[0034] 2) Place the PDMS-Si-H membrane in a dry isopropanol solution containing the surface-modifying compound (III). Use a quartz pipette to draw up a Karstedts Pt catalyst, activate it, add it to the reaction system, mix thoroughly, and allow to react. After the reaction is complete, wash several times and vacuum dry to obtain the modified PDMS sheet.

[0035] Furthermore, in step 2), the PDMS-Si-H membrane is a PDMS plate whose surface is hydrogenated after being treated with dilute hydrochloric acid.

[0036] The synthetic route of the modified PDMS plate is:

[0037]

[0038] In a sixth aspect, the present invention provides a modified PMMA plate, wherein the modified PMMA plate is formed by grafting a surface-modifying compound onto a PMMA plate after plasma cleaning treatment, wherein the chemical structure of the surface-modifying compound is as shown in formula (IV) described in the first aspect.

[0039] In a seventh aspect, the present invention provides a method for preparing the modified PMMA plate according to the sixth aspect, wherein the preparation steps are as follows:

[0040] 1) Synthesis of 2-(3-benzoylphenyl)-N-(3-(triethoxysilyl)propyl)propanamide (surface-modified compound (IV)): Ketoprofen and 3-aminopropyltrimethoxysilane were dissolved in DMF, DMAP was added and stirred, and then EDC 1 was added. The mixture was reacted at room temperature, extracted, dried by rotation, and purified to obtain surface-modified compound (IV) as a transparent oil.

[0041] 2) Cleaning the PMMA plate with a plasma cleaner, immediately immersing it in a methanol alkaline solution of the surface modification compound (IV) obtained in step 1) after cleaning, allowing the grafting reaction to proceed overnight in the dark, and finally washing it with methanol to obtain the modified PMMA plate.

[0042] Furthermore, in step 2), the cleaning conditions of the plasma cleaning machine are as follows: time 120s, power 210W, and oxygen gas.

[0043] The synthetic route of the modified PMMA plate is:

[0044]

[0045] The parent nucleus of the present invention is benzophenone, a commonly used photosensitizer. When excited by light of a specific wavelength (typically ultraviolet light near 365 nm), the photosensitizer produces highly reactive intermediates that can rapidly form covalent bonds with amino acids in surrounding proteins, thereby achieving the purpose of protein grafting. Due to the development of Western Blot technology, it is necessary to complete the grafting and fixation of proteins on the surfaces of different materials. However, many materials (such as quartz, PMMA, and PDMS) are inherently unable to attach proteins. Therefore, the present invention has developed four different grafting methods, utilizing three different benzophenone derivatives to bind to different plate surfaces treated in different ways, achieving surface protein grafting on a variety of materials.

[0046] Compared with the existing technical solutions, the present invention has the following advantages:

[0047] 1. The three surface modification compounds of the present invention can be used as different materials for surface modification of grafted proteins according to the surface properties of the materials, which expands the range of selectable surface modification compounds and broadens the range of materials that can be used in the simple western method.

[0048] 2. The three surface-modified compounds of the present invention have the characteristics of low raw material cost, few synthesis steps, high synthesis yield, simple purification, and good solubility.

[0049] 3. The surface grafting concept of the present invention includes but is not limited to surface grafting of quartz, PMMA, PDMS, capillaries and chips. The solution can be selected according to the characteristics of the material itself, which is highly flexible. BRIEF DESCRIPTION OF THE DRAWINGS

[0050] Figure 1 Graphs showing signal test results for Example 1 and Comparative Example 1;

[0051] Figure 2 The signal test results of Example 2 and Comparative Example 2 are shown;

[0052] Figure 3 Graphs showing signal test results for Example 3 and Comparative Example 3;

[0053] Figure 4 Graph showing the signal test results for Example 4 and Comparative Example 4. DETAILED DESCRIPTION

[0054] The technical solutions in the embodiments are described clearly and completely below. Obviously, the embodiments described below are only some of the embodiments of the present invention, not all of them. All other embodiments derived by persons of ordinary skill in the art based on the embodiments of the present invention without creative effort are also within the scope of protection of the present invention.

[0055] It will be understood that when used in this specification and the appended claims, the terms “comprises” and “comprising” indicate the presence of described features, integers, steps, operations, elements and / or components, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components and / or groups thereof.

[0056] It should also be understood that the terms used in this description of the embodiments of the present invention are only for the purpose of describing specific embodiments and are not intended to limit the embodiments of the present invention. As used in the description of the embodiments of the present invention and the appended claims, the singular forms "a", "an", and "the" are intended to include the plural forms unless the context clearly indicates otherwise.

[0057] The raw materials involved in the present invention can be directly purchased from the market. For process parameters not specifically noted, conventional techniques can be used.

[0058] Example 1: Testing of modified quartz plates.

[0059] 1) Pretreatment of the quartz plate: rinse the quartz plate with 0.1 mol / L HCl solution for 30 min, then rinse with deionized water for 10 min, rinse the quartz plate with 0.1 mol / L NaOH solution for 2 h, then rinse with methanol for 10 min, and finally blow dry with nitrogen.

[0060] 2) Grafting 3-aminopropyltrimethoxysilane (APS) onto quartz plate: Prepare a mixed solution of 3-aminopropyltrimethoxysilane and methanol (volume ratio: V APS :V MeOH =1:1) 50mL, then poured into a square Petri dish, then immersed the quartz plate in the square Petri dish until it was completely covered by the mixed solution, and then placed the square Petri dish in a 37° oven to react for 12-16 hours to complete the APS connection, and then rinsed with methanol for 10 minutes, and finally dried with nitrogen for use.

[0061] 3) Connecting 3-(bromomethyl)benzophenone to 3-aminopropyltrimethoxysilane: Dissolve 55 mg of 3-(bromomethyl)benzophenone and 5 mg of potassium carbonate powder in 50 mL of DMF, sonicate in the dark for 2 hours, and then immerse the quartz plate treated in step 2) in the mixed solution. React at room temperature for 12-16 hours. After the connection is completed, rinse with DMF for 3 minutes, then rinse with PBST for 3 minutes, and finally blow dry with nitrogen for use.

[0062] 4) Protein Immobilization: Use a pipette to pipette 3 μL of protein sample (HRP protein - concentration 10 ng / μL) onto five different locations on the surface of the quartz plate treated in step 3). Then, irradiate at a wavelength of 350 nm for at least 30 min. After irradiation, rinse the quartz plate with PBST. Finally, cover the surface of the quartz plate with ultrasensitive ECL luminescent liquid and use the 6000pro II luminescence camera (Guangzhou Boluteng Biotechnology Co., Ltd.) to record the protein immobilization effect.

[0063] Comparative Example 1: Similarly, a pipette was used to draw 3 uL of protein sample (HRP protein - concentration 10 ng / μL) onto five different locations on the surface of the quartz plate treated in step 3). The difference from the above was that Comparative Example 1 was not irradiated at a wavelength of 350 nm, but was only placed in a dark environment (the placement time was consistent with the irradiation time in step 4). Then, PBST was used to rinse the surface of the quartz plate. Finally, the ultrasensitive ECL luminescent liquid was spread over the surface of the quartz plate, and 6000pro II was used to take photos and record the luminescence.

[0064] The results of the photo recording are shown in Table 1 and Figure 1 As shown in the experimental result graph, it can be seen that there is a significant difference in the signal detection results of the two modified quartz plates, which were irradiated after adding the protein sample and those which were not irradiated, and then the ECL luminescent liquid was added after cleaning. The average maximum signal of the five points of Example 1 treated with irradiation was about 20,000 cts, while the average maximum signal of the five points of Control Example 1 not treated with irradiation was about 3,500 cts. Therefore, the signal of Example 1 treated with irradiation is significantly greater than that of Control Example 1.

[0065] Table 1 Signal values ​​of Example 1 and Comparative Example 1

[0066]

[0067] Example 2: Testing of modified quartz plates

[0068] 1)pheny l(3-(((3-(tr imethoxys ilyl)propy l)amino)methy l)pheny l)

[0069] Synthesis of methanone (surface-modified compound (II)): 3-aminopropyltrimethoxysilane (APS) (0.72 g, 4 mmol), 3-(bromomethyl)benzophenone (1.1 g, 4 mmol), and potassium carbonate (0.72 g, 5.2 mmol) were dissolved in 6 ml of DMF, protected from light, and reacted at room temperature for 3 hours to precipitate a white solid. The solid was filtered, dried with water, rinsed with methanol, and dried to obtain the surface-modified compound (II).

[0070] 2) Pretreatment of the quartz plate: rinse the quartz plate with 0.1 mol / L HCl solution for 30 min, then rinse with deionized water for 10 min, rinse the quartz plate with 0.1 mol / L NaOH solution for 2 h, then rinse with methanol for 10 min, and finally blow dry with nitrogen.

[0071] 3) Connecting the surface-modified compound (II) to the treated quartz plate: Prepare a mixed solution of the surface-modified compound (II) and DMF (dissolve 10 mg of the surface-modified compound (II) in 30 mL of DMF), then add the solution to a square Petri dish. Immerse the quartz plate in the square Petri dish until it is completely covered by the mixed solution. Then, place the square Petri dish in a 37° oven to react for 12-16 hours to complete the connection. Then, rinse with methanol for 10 minutes and finally blow dry with nitrogen for use.

[0072] 4) Protein Immobilization: Use a pipette to pipette 3 μL of protein sample (HRP protein - concentration 10 ng / μL) onto five different locations on the surface of the quartz plate treated in step 3). Then, irradiate at a wavelength of 350 nm for at least 30 min. After irradiation, rinse the quartz plate with PBST. Finally, cover the surface of the quartz plate with ultrasensitive ECL luminescent liquid and use the 6000pro II luminescence camera (Guangzhou Boluteng Biotechnology Co., Ltd.) to record the protein immobilization effect.

[0073] Comparative Example 2: Similarly, a pipette was used to draw 3 uL of protein sample (HRP protein - concentration 10 ng / μL) onto five different locations on the surface of the quartz plate treated in step 3). The difference from the above is that Comparative Example 2 was not irradiated at a wavelength of 350 nm, but was only placed in a dark environment (the placement time was consistent with the irradiation time in step 4)). Then, PBST was used to rinse the surface of the quartz plate. Finally, the ultrasensitive ECL luminescent liquid was spread over the surface of the quartz plate, and 6000pro II was used to take photos and record the luminescence.

[0074] The results of the photo recording are shown in Table 2 and Figure 2 As shown in the experimental result graph, it can be seen that there is a significant difference in the signal detection results of the two modified quartz plates after irradiation and without irradiation after the protein sample is added. The average maximum signal of the five points of Example 2 treated with irradiation is about 21000 cts, while the average maximum signal of the five points of Control Example 2 not treated with irradiation is about 2500 cts. Therefore, the signal of Example 2 treated with irradiation is significantly greater than that of Control Example 2.

[0075] Table 2 Signal values ​​of Example 2 and Comparative Example 2

[0076]

[0077] Example 3: Testing of modified PDMS

[0078] 1) Synthesis of pent-4-en-1-yl 2-(3-benzoyl phenyl)propanoate (surface-modified compound (III)): Ketoprofen (2.54 g, 10 mmol) and 4-penten-1-ol (1.44 ml, 12 mmol) were dissolved in 30 ml DMF, DMAP (0.12 g, 1 mmol) was added, and the mixture was stirred for 5 minutes. EDC 1 (4.79 g, 25 mmol) was then added, and the reaction was carried out at room temperature for 15 hours. The mixture was extracted with water and ethyl acetate, dried by rotation, and purified on a silica gel column to obtain surface-modified compound (III).

[0079] 2) PDMS-Si-H membrane is a PDMS sheet whose surface is hydrogenated after being treated with dilute hydrochloric acid, including but not limited to those purchased from Hangzhou Weisi Co., Ltd.

[0080] 3) Place the PDMS-Si-H membrane described in step 2) into a 25 mL dry isopropanol solution containing 2 g of surface-modifying compound (III). Use a quartz pipette to draw 0.5 mL of Karstedts Pt catalyst, activate it at 80°C, add it to the reaction system, mix thoroughly, and react at 35°C for 12-16 hours. After the reaction is complete, wash it several times with acetone and distilled water, dry it in a vacuum at 50°C for 4 hours, and remove it for later use. (The membrane will turn from transparent to milky white and opaque.)

[0081] (4) 3 μl of protein (HRP protein - concentration 10 ng / μL) was respectively aspirated and dropped on five different locations on the dried membrane, and then irradiated at 350 mm for 30 min. Finally, the membrane was washed with PBST and water for 15 min, and then ECL luminescent solution was added for signal detection.

[0082] Comparative Example 3: Similarly, a pipette was used to draw 3 uL of protein sample (HRP protein - concentration 10 ng / μL) onto five different locations on the membrane dried in step 3). The difference from the above was that Comparative Example 3 was not irradiated at a wavelength of 350 nm, but was only placed in a dark environment (the placement time was the same as the irradiation time in step 4). Finally, the membrane was washed with PBST and water for 15 minutes, and then ECL luminescent liquid was added for signal detection.

[0083] The results of the photo recording are shown in Table 3 and Figure 3 As shown in the experimental result diagram, it can be seen that there is an obvious difference in the results of signal detection between the two membranes that were irradiated after adding the protein sample and those that were not irradiated, and the ECL luminescent liquid was added after cleaning. The average maximum signal of the five points of Example 3 that was irradiated was about 24,000 cts, while the average maximum signal of the five points of Control Example 3 that was not irradiated was about 4,000 cts. Therefore, the signal of Example 3 that was irradiated was significantly greater than the signal of Control Example 3, which indicates that the modification and grafting of the plate was successful.

[0084] Table 3 Signal values ​​of Example 3 and Comparative Example 3

[0085]

[0086] Example 4: Testing of modified PMMA:

[0087] 1) Synthesis of 2-(3-benzoylphenyl)-N-(3-(triethoxysilyl)propyl)propanamide (surface-modified compound (IV)): Ketoprofen (2.54 g, 10 mmol) and 3-aminopropyltrimethoxysilane (2.8 ml, 12 mmol) were dissolved in 30 ml DMF, DMAP (0.12 g, 1 mmol) was added, and the mixture was stirred for 5 minutes. EDC 1 (4.79 g, 25 mmol) was then added and reacted at room temperature for 15 hours. The mixture was extracted with water and ethyl acetate, dried by spin drying, and purified on a silica gel column to obtain surface-modified compound (IV) as a transparent oily product.

[0088] 2) Use a plasma cleaner to clean the PMMA plate (conditions: time 120 s, power 210 W, gas is oxygen), and immediately soak it in 30 ml methanol alkaline solution of surface modification compound (IV) (30 mg surface modification compound (IV) is dissolved in 30 ml methanol and then 3 ml 1M NaOH aqueous solution is added). Grafting reaction is carried out at 35°C overnight in the dark, and finally rinsed with methanol for 15 minutes before use.

[0089] 3) After thoroughly drying the plate with a negative ion hair dryer, add 3 μL of protein sample (HRP protein concentration: 10 ng / μL) to five different locations on the surface. Irradiate the plate at 350 mm for at least 30 minutes. Finally, rinse the plate with PBST and 20% ammonium chloride solution and perform ECL luminescence detection (exposure time: 2 s, binning: 4 x 4).

[0090] Comparative Example 4: Similarly, 3 μL of protein sample (HRP protein - concentration 10 ng / μL) was pipetted using a pipette and added dropwise to five different locations on the surface of the PMMA plate treated in step 2). The difference from the above was that the control group was not irradiated at a wavelength of 350 nm, but was simply placed in a dark environment (the placement time was consistent with the irradiation time in step 3). Finally, the plate was washed with PBST and 20% ammonium chloride solution, and then luminescence detection was performed by ECL. Luminescence photography was recorded using 6000pro II.

[0091] The experimental data are shown in Table 4 and Figure 4 As shown in the figure, it can be seen from the experimental results that there is a significant difference in the signal detection results of the two PMMA plates, which were irradiated after adding the protein sample and those which were not irradiated, after being cleaned and then adding the ECL luminescent liquid. The average maximum signal of the five points of Example 4 treated with irradiation is about 18000 cts, while the average maximum signal of the five points of Control Example 4 not treated with irradiation is about 1500 cts. Therefore, the signal of Example 4 treated with irradiation is significantly greater than that of Control Example 4.

[0092] Table 4 Signal values ​​of Example 4 and Comparative Example 4

[0093]

[0094] The above embodiments are preferred implementation modes of the present invention, but the implementation modes of the present invention are not limited to the above embodiments. Any other changes, modifications, substitutions, combinations, and simplifications that do not deviate from the spirit and principles of the present invention should be considered as equivalent replacement methods and are included in the scope of protection of the present invention.

Claims

1. A surface-modified compound, characterized in that Its chemical structure is shown in formula (IV): 。 2. A modified PDMS plate, characterized in that, It is formed by grafting a surface modification compound onto a hydrosilane-treated PDMS sheet. The chemical structure of the surface modification compound is shown in formula (III): .

3. A method for preparing the modified PDMS plate according to claim 2, characterized in that: The preparation steps are as follows: 1) Synthesis of the surface-modified compound: Ketoprofen and 4-penten-1-ol were dissolved in DMF, DMAP was added and stirred, and then EDCl was added. The mixture was reacted and extracted at room temperature, dried, and purified to obtain the surface-modified compound. 2) Place the PDMS-Si-H membrane in a drying solution of isopropanol containing the surface modification compound; Use a quartz dropper to draw up the Karstedts Pt catalyst, add it into the reaction system after activation, mix well and react; After the reaction is completed, the modified PDMS plate is obtained by washing several times and vacuum drying.

4. A modified PMMA plate, characterized in that: The surface modification compound is grafted onto a PMMA plate after plasma cleaning, wherein the chemical structure of the surface modification compound is the formula (IV) as claimed in claim 1.

5. A method for preparing the modified PMMA plate according to claim 4, characterized in that: The preparation steps are as follows: 1) Synthesis of the surface-modified compound: Ketoprofen and 3-aminopropyltrimethoxysilane were dissolved in DMF, DMAP was added and stirred, and then EDCl was added. The mixture was reacted at room temperature, extracted, dried, and purified to obtain a surface-modified compound as a transparent oil. 2) Clean the PMMA plate using a plasma cleaner, and immediately soak it in a methanol alkaline solution of the surface modification compound obtained in step 1) after cleaning, and allow the grafting reaction to proceed overnight in the dark. Finally, rinse it with methanol to obtain the modified PMMA plate.

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