CN112938956B - Magnetic graphene oxide capable of adsorbing beta amyloid protein and preparation method thereof - Google Patents
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Abstract
The invention discloses magnetic graphene oxide capable of adsorbing beta amyloid and a preparation method thereof, wherein the magnetic graphene oxide comprises magnetic graphene oxide, a polyethyleneimine matrix, a silane coupling agent and folic acid, the polyethyleneimine matrix is synthesized by the silane coupling agent, the graphene oxide is compounded on the polyethyleneimine matrix, and the folic acid is loaded on the graphene oxide; the graphene oxide has a high specific surface area and rich surface functional groups, so that the graphene oxide has certain adsorption capacity, the graphene oxide magnetic material is subjected to graft modification by using polyethyleneimine, and a novel adsorption material obtained by compounding safe folic acid has a good adsorption effect on beta amyloid protein.
Description
Technical Field
The invention relates to the technical field of magnetic graphene oxide, in particular to magnetic graphene oxide capable of adsorbing beta amyloid and a preparation method thereof.
Background
The beta-amyloid protein has a molecular weight of about 4kDa, is hydrolyzed from beta amyloid precursor protein, is secreted by cells, and has a strong neurotoxic effect after the accumulation of cell matrix precipitates. Amyloid beta is produced by amyloid precursor protein in a variety of cells, circulates in blood, cerebrospinal fluid and cerebral interstitial fluid, is mostly bound to chaperone molecules, and exists in a few free states. Wherein the amyloid beta is associated with Alzheimer's disease and cerebral amyloid angiopathy. The process by which amyloid beta causes disorders is: overproduction of the neurotoxic substance amyloid beta (a β) in the brain leads to a β brain aggregation → neuronal degenerative death → brain atrophy → dementia. A β deposition is one of the important pathological features of Alzheimer's Disease (AD), and is a common pathway for the induction of AD for a variety of reasons, and is also a key factor in the formation and progression of AD. Therapeutic strategies aimed at abeta clearance are one of the currently mainstream directions of research.
The graphene oxide has a high specific surface area and abundant surface functional groups, so that the graphene oxide has a certain adsorption capacity, but the existing graphene oxide has a general adsorption effect on beta amyloid protein, and meanwhile, the graphene oxide does not have magnetism, so that the graphene oxide cannot be subjected to magnetic recovery, and the practicability is poor.
Disclosure of Invention
The invention aims to provide magnetic graphene oxide capable of adsorbing beta amyloid and a preparation method thereof, and the magnetic graphene oxide has the advantages of good beta amyloid adsorption effect and relatively simple preparation, so that the problems in the background art are solved.
In order to achieve the purpose, the invention provides the following technical scheme:
the magnetic graphene oxide capable of adsorbing the beta amyloid protein comprises magnetic graphene oxide, a polyethyleneimine matrix, a silane coupling agent and folic acid, wherein the polyethyleneimine matrix is synthesized through the silane coupling agent, the graphene oxide is compounded on the polyethyleneimine matrix, and the folic acid is loaded on the graphene oxide.
Another technical problem to be solved by the present invention is to provide a method for preparing magnetic graphene oxide capable of adsorbing amyloid beta, comprising the following steps:
s1: preparing magnetic graphene oxide; weighing 15-30mg of graphene oxide, dissolving the graphene oxide in 15-30ml of diethylene glycol solution, uniformly stirring, putting the mixed solution into ultrasonic equipment for ultrasonic mixing, controlling the ultrasonic mixing time to be 26-30min, then sequentially adding 250mg of sodium acetate and 200mg of ferric chloride hexahydrate under the action of magnetic stirring to form uniform yellow suspension, putting the suspension into a reaction kettle, adjusting the temperature level in the reaction kettle to 200 ℃, enabling the suspension to react in the reaction kettle for 8-10h at 200 ℃, then putting the suspension into a centrifuge, centrifuging the suspension for 5min at the revolution of 3000r/min, then pouring out the supernatant above the precipitate to obtain the precipitate, centrifuging and washing the precipitate for 10-20 times by sequentially using 400ml of anhydrous ethanol and 350ml of distilled water, obtaining high-quality magnetic graphene oxide precipitate, and then carrying out vacuum drying on the high-quality magnetic graphene oxide precipitate to obtain magnetic graphene oxide;
s2: preparing a polyethyleneimine matrix:
a, preparing a polyethyleneimine emulsion: mixing 8-10 mL of 20% polyethyleneimine water solution, 10-12 mL of liquid paraffin and 2mL of polyvinyl alcohol pore-forming agent in percentage by mass, adding a surfactant into the mixed solution to form a mixed solution, wherein the final concentration of the surfactant is 0.04-0.06 g/mL, putting the mixed solution into ultrasonic equipment for ultrasonic mixing, and controlling the ultrasonic mixing time to be 2-3min to form polyethyleneimine emulsion;
b pre-crosslinking polymerization reaction: taking 15-20 mL of the polyethyleneimine emulsion, slowly dropwise adding 15-20 mL of a cross-linking agent under the action of magnetic stirring, and pre-crosslinking for 2-3 hours;
c, crosslinking polymerization reaction: under the condition of magnetic stirring, slowly dropwise adding 5-10 mL of sodium hydroxide solution into 20mL of pre-crosslinked mixture prepared by the pre-crosslinking polymerization reaction, controlling the concentration of the sodium hydroxide solution to be 1.0-2.0 mol/L, after the reaction is finished, performing centrifugal treatment on the mixture, and centrifuging to remove supernatant to obtain a polyethyleneimine matrix;
s3: preparing polyethyleneimine modified magnetic graphene oxide: weighing 20-40mg of magnetic graphene oxide, dissolving the magnetic graphene oxide in 20-40ml of phosphate buffer solution with the pH value of 7.4, then putting the mixed solution into ultrasonic equipment for ultrasonic mixing, and controlling the ultrasonic mixing time to be 5-10min to ensure that the mixed solution is uniformly dispersed; then sequentially adding 100-200mg of carbodiimide hydrochloride, 50-117mg of N-hydroxysuccinimide and 200-400mg of polyethyleneimine matrix into the mixed solution, uniformly stirring, filtering to obtain a filter cake, repeatedly washing the filter cake for 10 times by using 400-1000ml of ultrapure water to obtain a polyethyleneimine modified magnetic graphene oxide precipitate, and then carrying out vacuum drying on the polyethyleneimine modified magnetic graphene oxide precipitate at the temperature of 40-60 ℃ for 1-2 days to finally obtain the polyethyleneimine modified magnetic graphene oxide;
s4: preparing magnetic graphene oxide modified by polyethyleneimine loaded with folic acid: weighing 5-20mg of polyethyleneimine modified magnetic graphene oxide, dissolving in 5-20ml of ultrapure water, adding 1-4mg of silane coupling agent and 5-20mg of folic acid powder, placing the mixed solution into ultrasonic equipment for ultrasonic mixing, and controlling the ultrasonic mixing time to be 1-2 hours to obtain the polyethyleneimine modified magnetic graphene oxide loaded with folic acid.
Preferably, in S2, the addition mass of the cross-linking agent is the same as the addition mass of the polyethyleneimine emulsion.
Preferably, in S2, the polyethyleneimine matrix is obtained by washing with isopropanol, dehydrated ether and distilled water for 5 to 10 times.
Preferably, in S4, the silane coupling agent is 3-aminopropyltriethoxysilane.
Compared with the prior art, the invention has the beneficial effects that: the invention provides magnetic graphene oxide capable of adsorbing beta amyloid and a preparation method thereof, wherein the magnetic graphene oxide comprises magnetic graphene oxide, a polyethyleneimine matrix, a silane coupling agent and folic acid, the polyethyleneimine matrix is synthesized by the silane coupling agent, the graphene oxide is compounded on the polyethyleneimine matrix, and the folic acid is loaded on the graphene oxide; the graphene oxide has a high specific surface area and abundant surface functional groups, so that the graphene oxide has certain adsorption capacity, the graphene oxide magnetic material is subjected to graft modification by using polyethyleneimine, and meanwhile, a novel adsorption material obtained by compounding safe folic acid has a good adsorption effect on beta-amyloid protein, and can be magnetically recycled after being injected into cerebrospinal fluid to adsorb the beta-amyloid protein, so that the beta-amyloid protein can be removed.
Drawings
FIG. 1 is a block diagram of the overall process flow of the present invention;
FIG. 2 is a block diagram of a process for preparing a polyethyleneimine matrix according to the present invention;
FIG. 3 is a path of a mouse water maze experiment without the invention of the present invention;
FIG. 4 is a path of the mouse water maze experiment using the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The magnetic graphene oxide capable of adsorbing the amyloid beta comprises magnetic graphene oxide, a polyethyleneimine matrix, a silane coupling agent and folic acid, wherein the polyethyleneimine matrix is synthesized through the silane coupling agent, the graphene oxide is compounded on the polyethyleneimine matrix, and the folic acid is loaded on the graphene oxide.
Example one
Referring to fig. 1, a method for preparing magnetic graphene oxide capable of adsorbing amyloid beta includes the following steps:
the first step is as follows: preparing magnetic graphene oxide; weighing 25mg of graphene oxide, dissolving the graphene oxide in 25ml of diethylene glycol solution, uniformly stirring, putting the mixed solution into ultrasonic equipment for ultrasonic mixing, controlling the ultrasonic mixing time to be 30min, then sequentially adding 150mg of sodium acetate and 100mg of ferric chloride hexahydrate under the action of magnetic stirring to form uniform yellow suspension, putting the suspension into a reaction kettle, adjusting the temperature of the reaction kettle to be 200 ℃, enabling the suspension to react in the reaction kettle for 8h at 200 ℃, putting the suspension into a centrifugal machine, centrifuging the suspension for 5min at the speed of 3000r/min, pouring out supernatant above the precipitate to obtain precipitate, sequentially centrifuging and washing the precipitate for 15 times by 400ml of absolute ethyl alcohol and 250ml of distilled water to obtain high-quality magnetic graphene oxide precipitate, and then carrying out vacuum drying on the high-quality magnetic graphene oxide precipitate, obtaining magnetic graphene oxide;
the second step is that: preparing a polyethyleneimine emulsion: mixing 10mL of 20% polyethyleneimine water solution, 10mL of liquid paraffin and 2mL of polyvinyl alcohol pore-forming agent in percentage by mass, adding a surfactant into the mixed solution to form a mixed solution, wherein the final concentration of the surfactant is 0.04g/mL, putting the mixed solution into ultrasonic equipment for ultrasonic mixing, and controlling the ultrasonic mixing time to be 3min to form polyethyleneimine emulsion;
the third step: preparing polyethyleneimine modified magnetic graphene oxide: weighing 40mg of magnetic graphene oxide, dissolving the magnetic graphene oxide in 40ml of phosphate buffer solution with the pH value of 7.4, then putting the mixed solution into ultrasonic equipment for ultrasonic mixing, and controlling the ultrasonic mixing time to be 5min so as to uniformly disperse the mixed solution; then sequentially adding 100mg of carbodiimide hydrochloride, 50mg of N-hydroxysuccinimide and 200mg of polyethyleneimine emulsion into the mixed solution, uniformly stirring, filtering to obtain a filter cake, repeatedly washing the filter cake for 10 times by using 1000ml of ultrapure water to obtain a polyethyleneimine modified magnetic graphene oxide precipitate, and then carrying out vacuum drying on the polyethyleneimine modified magnetic graphene oxide precipitate, wherein the temperature of the vacuum drying is controlled to be 40-60 ℃, and the drying time is 1 day, so as to finally obtain the polyethyleneimine modified magnetic graphene oxide;
the fourth step: preparing magnetic graphene oxide modified by polyethyleneimine loaded with folic acid: weighing 20mg of polyethyleneimine modified magnetic graphene oxide, dissolving in 20ml of ultrapure water, adding 4mg of silane coupling agent and 20mg of folic acid powder, wherein the silane coupling agent is 3-aminopropyltriethoxysilane, placing the mixed solution into ultrasonic equipment for ultrasonic mixing, and controlling the ultrasonic mixing time to be 2 hours to obtain the folic acid loaded polyethyleneimine modified magnetic graphene oxide.
Example two
Referring to fig. 1-2, a method for preparing magnetic graphene oxide capable of adsorbing amyloid beta includes the following steps:
the first step is as follows: preparing magnetic graphene oxide; weighing 30mg of graphene oxide, dissolving the graphene oxide in 30ml of diethylene glycol solution, uniformly stirring, putting the mixed solution into ultrasonic equipment for ultrasonic mixing, controlling the ultrasonic mixing time to be 30min, then sequentially adding 250mg of sodium acetate and 200mg of ferric chloride hexahydrate under the action of magnetic stirring to form uniform yellow suspension, putting the suspension into a reaction kettle, adjusting the temperature of the reaction kettle to be 200 ℃, enabling the suspension to react in the reaction kettle at 200 ℃ for 10h, putting the suspension into a centrifugal machine, centrifuging the suspension for 5min at the speed of 3000r/min, pouring out supernatant above the precipitate to obtain precipitate, sequentially centrifuging and washing the precipitate for 20 times by 300ml of absolute ethyl alcohol and 350ml of distilled water to obtain high-quality magnetic graphene oxide precipitate, and then carrying out vacuum drying on the high-quality magnetic graphene oxide precipitate, obtaining magnetic graphene oxide;
the second step is that: preparing a polyethyleneimine matrix:
a, preparing a polyethyleneimine emulsion: mixing 10mL of 20% polyethyleneimine water solution, 10mL of liquid paraffin and 2mL of polyvinyl alcohol pore-forming agent in percentage by mass, adding a surfactant into the mixed solution to form a mixed solution, wherein the final concentration of the surfactant is 0.06g/mL, putting the mixed solution into ultrasonic equipment for ultrasonic mixing, and controlling the ultrasonic mixing time to be 3min to form polyethyleneimine emulsion;
b pre-crosslinking polymerization reaction: taking 20mL of the polyethyleneimine emulsion, slowly dropwise adding 20mL of a cross-linking agent under the action of magnetic stirring, and pre-crosslinking for 2 hours, wherein the adding mass of the cross-linking agent is the same as that of the polyethyleneimine emulsion;
c, crosslinking polymerization reaction: under the condition of magnetic stirring, taking 20mL of the pre-crosslinking mixture prepared by the pre-crosslinking polymerization reaction, slowly and dropwise adding 10mL of sodium hydroxide solution, controlling the concentration of the sodium hydroxide solution to be 2.0mol/L, centrifuging the mixture after the reaction is finished, centrifuging and removing supernatant to obtain a polyethyleneimine matrix, wherein the polyethyleneimine matrix needs to be washed with isopropanol, anhydrous ether and distilled water for 10 times respectively.
The third step: preparing polyethyleneimine modified magnetic graphene oxide: weighing 20mg of magnetic graphene oxide, dissolving the magnetic graphene oxide in 20ml of phosphate buffer solution with the pH value of 7.4, then putting the mixed solution into ultrasonic equipment for ultrasonic mixing, and controlling the ultrasonic mixing time to be 5min so as to uniformly disperse the mixed solution; then sequentially adding 100mg of carbodiimide hydrochloride, 100mg of N-hydroxysuccinimide and 300mg of polyethyleneimine matrix into the mixed solution, uniformly stirring, filtering to obtain a filter cake, repeatedly washing the filter cake for 10 times by using 1000ml of ultrapure water to obtain a polyethyleneimine modified magnetic graphene oxide precipitate, and then carrying out vacuum drying on the polyethyleneimine modified magnetic graphene oxide precipitate, wherein the temperature of the vacuum drying is controlled to be 40-60 ℃, and the drying time is 1 day, so as to finally obtain polyethyleneimine modified magnetic graphene oxide;
the fourth step: preparing magnetic graphene oxide modified by polyethyleneimine loaded with folic acid: weighing 20mg of polyethyleneimine modified magnetic graphene oxide, dissolving in 20ml of ultrapure water, adding 3mg of silane coupling agent and 20mg of folic acid powder, wherein the silane coupling agent is 3-aminopropyl triethoxysilane, then placing the mixed solution into ultrasonic equipment for ultrasonic mixing, and controlling the ultrasonic mixing time to be 2 hours, so as to obtain the polyethyleneimine modified magnetic graphene oxide loaded with folic acid.
It is now known that a β deposition is one of the important pathological features of Alzheimer's Disease (AD), and is a common pathway for the induction of AD for a variety of reasons, and is also a key factor in the development and progression of AD. Therapeutic strategies aimed at abeta clearance are one of the currently mainstream research directions. The magnetic graphene oxide capable of adsorbing the beta-amyloid has wide application prospect in research and development of medicines for diseases related to the beta-amyloid, and experiments show that the magnetic graphene oxide can realize rapid elimination of the beta-amyloid, does not participate in metabolism, and is an ideal elimination material. In the performance experiment of the mouse model with the Alzheimer's disease, namely the Morris water maze experiment, before and after the application of the invention, the comparison graphs are shown in the attached drawings 3 and 4, the attached drawing 3 is a mouse path without the application of the invention, and the attached drawing 4 is a mouse path without the application of the invention. The invention provides a brand new thought for the research and development of medicaments for beta amyloid related diseases including Alzheimer's disease, and is expected to become a medicament for preventing and treating Alzheimer's disease.
In summary, the magnetic graphene oxide capable of adsorbing amyloid beta and the preparation method thereof provided by the invention comprise magnetic graphene oxide, a polyethyleneimine matrix, a silane coupling agent and folic acid, wherein the polyethyleneimine matrix is synthesized by the silane coupling agent, the graphene oxide is compounded on the polyethyleneimine matrix, and the folic acid is loaded on the graphene oxide; the graphene oxide has a high specific surface area and rich surface functional groups, so that the graphene oxide has certain adsorption capacity, the graphene oxide magnetic material is subjected to graft modification by using polyethyleneimine, and a novel adsorption material obtained by compounding safe folic acid has a good adsorption effect on beta amyloid protein.
It is noted that, herein, relational terms such as first and second, and the like may be used solely to distinguish one entity or action from another entity or action without necessarily requiring or implying any actual such relationship or order between such entities or actions. Also, the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be able to cover the technical solutions and the inventive concepts of the present invention within the technical scope of the present invention.
Claims (5)
1. The preparation method of the magnetic graphene oxide capable of adsorbing the amyloid beta is characterized by comprising the following steps of:
s1: preparing magnetic graphene oxide; weighing 15-30mg of graphene oxide, dissolving the graphene oxide in 15-30ml of diethylene glycol solution, uniformly stirring, putting the mixed solution into ultrasonic equipment for ultrasonic mixing, controlling the ultrasonic mixing time to be 26-30min, then sequentially adding 250mg of sodium acetate and 200mg of ferric chloride hexahydrate under the action of magnetic stirring to form uniform yellow suspension, putting the suspension into a reaction kettle, adjusting the temperature level in the reaction kettle to 200 ℃, enabling the suspension to react in the reaction kettle for 8-10h at 200 ℃, then putting the suspension into a centrifuge, centrifuging the suspension for 5min at the revolution of 3000r/min, then pouring out the supernatant above the precipitate to obtain the precipitate, centrifuging and washing the precipitate for 10-20 times by sequentially using 400ml of anhydrous ethanol and 350ml of distilled water, obtaining high-quality magnetic graphene oxide precipitate, and then carrying out vacuum drying on the high-quality magnetic graphene oxide precipitate to obtain magnetic graphene oxide;
s2: preparing a polyethyleneimine matrix:
a, preparing polyethyleneimine emulsion: mixing 8-10 mL of 20% polyethyleneimine water solution, 10-12 mL of liquid paraffin and 2mL of polyvinyl alcohol pore-forming agent in percentage by mass, adding a surfactant into the mixed solution to form a mixed solution, wherein the final concentration of the surfactant is 0.04-0.06 g/mL, putting the mixed solution into ultrasonic equipment for ultrasonic mixing, and controlling the ultrasonic mixing time to be 2-3min to form polyethyleneimine emulsion;
b pre-crosslinking polymerization reaction: taking 15-20 mL of the polyethyleneimine emulsion, slowly dropwise adding 15-20 mL of a cross-linking agent under the action of magnetic stirring, and pre-crosslinking for 2-3 hours;
c, crosslinking polymerization reaction: under the condition of magnetic stirring, slowly dropwise adding 5-10 mL of sodium hydroxide solution into 20mL of pre-crosslinked mixture prepared by the pre-crosslinking polymerization reaction, controlling the concentration of the sodium hydroxide solution to be 1.0-2.0 mol/L, after the reaction is finished, performing centrifugal treatment on the mixture, and centrifuging to remove supernatant to obtain a polyethyleneimine matrix;
s3: preparing polyethyleneimine modified magnetic graphene oxide: weighing 20-40mg of magnetic graphene oxide, dissolving the magnetic graphene oxide in 20-40ml of phosphate buffer solution with the pH value of 7.4, then putting the mixed solution into ultrasonic equipment for ultrasonic mixing, and controlling the ultrasonic mixing time to be 5-10min to ensure that the mixed solution is uniformly dispersed; then sequentially adding 200mg of carbodiimide hydrochloride, 50-117mg of N-hydroxysuccinimide and 400mg of polyethyleneimine matrix into the mixed solution, uniformly stirring, filtering to obtain a filter cake, repeatedly washing the filter cake for 10 times by using 1000ml of ultrapure water to obtain a polyethyleneimine modified magnetic graphene oxide precipitate, and then carrying out vacuum drying on the polyethyleneimine modified magnetic graphene oxide precipitate to finally obtain polyethyleneimine modified magnetic graphene oxide;
s4: preparing magnetic graphene oxide modified by polyethyleneimine loaded with folic acid: weighing 5-20mg of polyethyleneimine modified magnetic graphene oxide, dissolving in 5-20ml of ultrapure water, adding 1-4mg of silane coupling agent and 5-20mg of folic acid powder, placing the mixed solution into ultrasonic equipment for ultrasonic mixing, and controlling the ultrasonic mixing time to be 1-2 hours to obtain the polyethyleneimine modified magnetic graphene oxide loaded with folic acid.
2. The method according to claim 1, wherein in S2, the addition amount of the cross-linking agent is the same as the addition amount of the polyethyleneimine emulsion.
3. The method according to claim 1, wherein in S2, the polyethyleneimine matrix is obtained by washing with isopropanol, dehydrated ether, and distilled water for 5-10 times.
4. The method for preparing magnetic graphene oxide capable of adsorbing beta-amyloid according to claim 1, wherein the temperature of vacuum drying of S3 is controlled to be 40-60 ℃, and the drying time is 1-2 days.
5. The method for preparing magnetic graphene oxide capable of adsorbing amyloid beta according to claim 1, wherein in S4, the silane coupling agent is 3-aminopropyltriethoxysilane.
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