CN117563570A - Resin for protein adsorption and preparation method thereof - Google Patents

Resin for protein adsorption and preparation method thereof Download PDF

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Publication number
CN117563570A
CN117563570A CN202410061114.0A CN202410061114A CN117563570A CN 117563570 A CN117563570 A CN 117563570A CN 202410061114 A CN202410061114 A CN 202410061114A CN 117563570 A CN117563570 A CN 117563570A
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resin
thiourea
protein adsorption
solution
polyethyleneimine
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CN117563570B (en
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郭东前
邓宁
王鹏
李昕杰
李国超
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Xi'an Innvoate Environmental Protection Technology Co ltd
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Xi'an Innvoate Environmental Protection Technology Co ltd
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    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/22Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/26Synthetic macromolecular compounds
    • B01J20/265Synthetic macromolecular compounds modified or post-treated polymers
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/28Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
    • B01J20/28014Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
    • B01J20/28026Particles within, immobilised, dispersed, entrapped in or on a matrix, e.g. a resin

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  • Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dispersion Chemistry (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)

Abstract

The invention belongs to the technical field of solid adsorbents, and discloses a resin for protein adsorption and a preparation method thereof. The preparation method of the resin comprises the following steps: swelling polystyrene-divinylbenzene polymer microspheres by N, N-dimethylformamide, mixing the microspheres with thiourea solution, and carrying out hydrothermal reaction to obtain a thiourea modified resin carrier; and soaking the thiourea modified resin carrier in carnosic acid solution, and finally placing the thiourea modified resin carrier in a mixed solution of polylysine and polyethyleneimine. According to the invention, the thiourea modified resin carrier treated by carnosic acid can effectively improve the loading effect of the resin on polylysine and polyethyleneimine, so that the adsorption performance is improved and the risk of falling particles is reduced.

Description

Resin for protein adsorption and preparation method thereof
Technical Field
The invention belongs to the technical field of solid adsorbents, and discloses a resin for protein adsorption and a preparation method thereof.
Background
Blood perfusion is a blood purification technique in which the blood of a patient is introduced into a perfusion apparatus containing a solid adsorbent, and exogenous or endogenous toxins, drugs or metabolic wastes which cannot be removed by dialysis in the blood are removed by adsorption. The core technology is mainly internal adsorption resin, and the adsorption resin used in the market at present mainly comprises active carbon, polysaccharide and synthetic resin, wherein the synthetic resin has advantages in mechanical strength, chemical stability and controllability of pore structure and functional groups. In the existing synthetic resin products on the market, macroporous adsorption resin is commonly used for whole blood perfusion, and the adsorption process is realized through physical adsorption of Van der Waals force, hydrogen bonding and the like. The styrene neutral macroporous adsorption resin in the synthetic resin has wider adsorption spectrum, is suitable for adsorbing various pathogenic substances in various diseases, and achieves the purpose of quick effect. Because the molecular weight of the protein is large, the adsorption effect of the broad-spectrum adsorbent is not ideal, and the selectivity is poor. The general method is to modify and modify the framework of the adsorbent to achieve the aim of improving the adsorption effect or specific adsorption. CN112791712a discloses an adsorbent for removing protein-bound uremic toxins by blood perfusion and a preparation method thereof, which adopts a method of imprinting molecules to achieve the purpose of specific adsorption, but has poor adsorption effect. CN111957304a discloses a macroporous adsorption resin for blood perfusion, which achieves the aim of improving the adsorption effect by grafting polyvinylpyrrolidone on the surface of white spheres, but has the risk of falling off particles.
Disclosure of Invention
The object of the present invention is to improve the adsorption properties of resins and reduce the risk of their particles falling off.
In order to solve the technical problems, the present invention provides a resin for protein adsorption and a preparation method thereof to meet the needs in the art.
In one aspect, the present invention relates to a method for preparing a resin for protein adsorption, comprising: swelling polystyrene-divinylbenzene polymer microspheres by N, N-dimethylformamide, mixing the microspheres with thiourea solution, and carrying out hydrothermal reaction to obtain a thiourea modified resin carrier;
and soaking the thiourea modified resin carrier in carnosic acid solution, and finally placing the thiourea modified resin carrier in a mixed solution of polylysine and polyethyleneimine.
Further, in the preparation method of the resin for protein adsorption, the concentration of the thiourea solution is 10-20wt%, and the solvent of the thiourea solution is water;
and the ratio of the swelled polystyrene-divinylbenzene polymer microspheres to the thiourea solution is 1:20-30 in terms of g/mL.
Further, in the preparation method of the resin for protein adsorption, the temperature of the hydrothermal reaction is 150-200 ℃ and the time is 12-48 h.
Further, in the preparation method of the resin for protein adsorption, the concentration of the carnosic acid solution is 20-30wt%, and the solvent of the carnosic acid solution is ethanol;
and the ratio of the thiourea modified resin carrier to the carnosic acid solution is 1:10-20 in terms of g/mL.
Further, in the preparation method of the resin for protein adsorption, the infiltration temperature is 50-60 ℃, and the infiltration time is 8-16 h.
In the preparation method of the resin for protein adsorption, the concentration of the polylysine in the mixed solution of the polylysine and the polyethyleneimine is 3-10wt%, and the concentration of the polyethyleneimine is 3-10wt%.
Further, in the preparation method of the resin for protein adsorption, the reaction temperature in the mixed solution of polylysine and polyethyleneimine is room temperature, and the reaction time is 12-24 hours.
In another aspect, the present invention relates to a resin for protein adsorption, which is prepared by the above-mentioned method for preparing a resin for protein adsorption.
Compared with the prior art, the technical scheme provided by the invention has the following beneficial effects or advantages: (1) According to the invention, a thiourea modification mode is adopted, so that a resin skeleton is grafted with reduced thiocarbonyl and amino functional groups; (2) The invention is used for improving the adsorption effect and the specific adsorption capacity of the resin by grafting polylysine and polyethyleneimine; (3) Experiments show that compared with polystyrene-divinylbenzene polymer microspheres, the thiourea modified resin carrier treated by carnosic acid shows a better effect of combining with polylysine or polyethyleneimine, can effectively improve the adsorption performance of the resin and reduce the falling risk of particles; (4) The invention does not adopt coupling reagents with toxicity risks such as epichlorohydrin, carbonyl diimidazole and the like to deactivate the carrier coupling functional unit, and has better biocompatibility.
Drawings
In order to more clearly illustrate the embodiments of the invention or the technical solutions in the prior art, the drawings that are required in the embodiments or the description of the prior art will be briefly described, it being obvious that the drawings in the following description are only some embodiments of the invention, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
FIG. 1 is a graph showing the results of the test of the adsorption performance of a resin to a protein.
FIG. 2 is a graph showing the results of the particle shedding test of the resin.
Detailed Description
The following describes the technical aspects of the present invention with reference to examples, but the present invention is not limited to the following examples.
The experimental methods and the detection methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available unless otherwise specified.
Example 1
This example provides a process for preparing a resin for protein adsorption.
Step 1: the polystyrene-divinylbenzene polymer microspheres (with the crosslinking degree of about 10 percent, the particle size distribution of 10-50 mu m and the pore size distribution of 5-100 nm) are washed by absolute ethyl alcohol and then immersed in N, N-dimethylformamide (with the purity of more than 99.9 percent) for 12 hours.
Step 2: and (3) mixing the polystyrene-divinylbenzene polymer microspheres obtained in the step (1) with 10wt% thiourea solution (solid-liquid ratio is 1:20, g/mL), putting the mixture into a high-pressure hydrothermal reaction kettle for carrying out hydrothermal reaction at 150 ℃ for 12 hours, taking out the mixture, and washing off residual chemical reagents on the resin surface and in the pore canal by using ethanol and pure water to obtain the thiourea modified resin carrier.
Step 3: and (3) soaking the thiourea modified resin carrier in a 20wt% carnosic acid solution (solid-liquid ratio is 1:10, g/mL) at 50 ℃ for 8 hours, taking out, placing the resin carrier in a mixed solution of polylysine and polyethyleneimine (the concentration of polylysine is 3wt% and the concentration of polyethyleneimine is 3 wt%) for reaction at room temperature for 12 hours, and washing with ethanol and water after the reaction is completed, and drying to obtain the resin. The carnosic acid solution is dissolved by using ethanol as a solvent and ultrasonically. The thiourea solution is dissolved by stirring with ultrapure water as a solvent.
Example 2
This example provides a process for preparing a resin for protein adsorption.
Step 1: the polystyrene-divinylbenzene polymer microspheres (with the crosslinking degree of about 10 percent, the particle size distribution of 10-50 mu m and the pore size distribution of 5-100 nm) are washed by absolute ethyl alcohol and then immersed in N, N-dimethylformamide (with the purity of more than 99.9 percent) for 12 hours.
Step 2: and (3) mixing the polystyrene-divinylbenzene polymer microspheres obtained in the step (1) with a 15wt% thiourea solution (solid-liquid ratio is 1:25, g/mL), putting the mixture into a high-pressure hydrothermal reaction kettle for hydrothermal reaction at 180 ℃ for 24 hours, taking out the mixture, and washing off residual chemical reagents on the resin surface and in the pore canal by using ethanol and pure water to obtain the thiourea modified resin carrier.
Step 3: and (3) soaking the thiourea modified resin carrier in a 25wt% carnosic acid solution (solid-to-liquid ratio is 1:15, g/mL) at 55 ℃ for 12 hours, taking out, placing the resin carrier in a mixed solution of polylysine and polyethyleneimine (the concentration of polylysine is 5wt% and the concentration of polyethyleneimine is 5 wt%) for 18 hours at room temperature, washing with ethanol and water after the reaction is completed, and drying to obtain the resin. The carnosic acid solution is dissolved by using ethanol as a solvent and ultrasonically. The thiourea solution is dissolved by stirring with ultrapure water as a solvent.
Example 3
This example provides a process for preparing a resin for protein adsorption.
Step 1: the polystyrene-divinylbenzene polymer microspheres (with the crosslinking degree of about 10 percent, the particle size distribution of 10-50 mu m and the pore size distribution of 5-100 nm) are washed by absolute ethyl alcohol and then immersed in N, N-dimethylformamide (with the purity of more than 99.9 percent) for 12 hours.
Step 2: and (3) mixing the polystyrene-divinylbenzene polymer microspheres obtained in the step (1) with a 20wt% thiourea solution (solid-liquid ratio is 1:30, g/mL), putting the mixture into a high-pressure hydrothermal reaction kettle, performing hydrothermal reaction at 200 ℃ for 48 hours, taking out, and washing off residual chemical reagents on the resin surface and in the pore canal by using ethanol and pure water to obtain the thiourea modified resin carrier.
Step 3: and (3) soaking the thiourea modified resin carrier in a 30wt% carnosic acid solution (solid-liquid ratio is 1:20, g/mL) at 60 ℃ for 16h, taking out, placing the resin carrier in a mixed solution of polylysine and polyethyleneimine (the concentration of polylysine is 10wt% and the concentration of polyethyleneimine is 10 wt%) for reaction at room temperature for 24h, washing with ethanol and water after the reaction is completed, and drying to obtain the resin. The carnosic acid solution is dissolved by using ethanol as a solvent and ultrasonically. The thiourea solution is dissolved by stirring with ultrapure water as a solvent.
Comparative example 1
This comparative example provides a resin preparation process of a resin carrier that has not been modified with thiourea.
Step 1: the polystyrene-divinylbenzene polymer microspheres (with the crosslinking degree of about 10 percent, the particle size distribution of 10-50 mu m and the pore size distribution of 5-100 nm) are washed by absolute ethyl alcohol and then immersed in N, N-dimethylformamide (with the purity of more than 99.9 percent) for 12 hours.
Step 2: and (3) washing the polystyrene-divinylbenzene polymer microspheres obtained in the step (1) with ethanol and pure water to remove residual chemical reagents on the resin surface and in the pore canal, thereby obtaining the resin carrier.
Step 3: soaking a resin carrier in 30wt% carnosic acid solution (solid-liquid ratio is 1:20, g/mL) at 60 ℃ for 16h, taking out, placing the resin carrier in a mixed solution of polylysine and polyethyleneimine (the concentration of polylysine is 10wt% and the concentration of polyethyleneimine is 10 wt%) for reaction at room temperature for 24h, washing with ethanol and water after the reaction is completed, and drying to obtain the resin. The carnosic acid solution is dissolved by using ethanol as a solvent and ultrasonically. The thiourea solution is dissolved by stirring with ultrapure water as a solvent.
Comparative example 2
This comparative example is identical to example 3, except that it has not been treated with carnosic acid solution.
Example 4
The present example provides performance tests for the resins prepared in examples 1-3 and comparative examples 1-2, with CN104492402a as a control.
(1) Lipoprotein adsorption Property
In a 20mL three-necked flask with a stopper, 2mL of resin (the resin prepared in example 1-3, comparative example 1-2 and example 1 of CN 104492402A) and 4mL of plasma (the lipoprotein concentration is 130-140 mg/dL) of a patient suffering from hyperlipidemia are added according to the ratio of 1mL of resin to 2mL of serum, the flask is placed in a constant temperature water tank at 37 ℃ for shaking for 1 hour, the lipoprotein content in the serum before and after absorption is detected by sucking the serum, the absorption rate is calculated, and the test result is shown in figure 1.
As can be seen from FIG. 1, the adsorption effect of the resin on the protein can be effectively improved by grafting polylysine and polyethyleneimine compared with comparative examples 1-2 and the prior art.
(2) Particle shedding performance
The resins obtained in examples 1 to 3, comparative examples 1 to 2 and example 1 of CN104492402A were subjected to a particle shedding test (refer to the particle shedding test in YY/T0464-2019, single use hemoperfusion apparatus) and the test results are shown in FIG. 2.
As can be seen from FIG. 2, the thiourea modified resin carrier treated by carnosic acid in the invention has a better effect of combining with polylysine or polyethyleneimine compared with polystyrene-divinylbenzene polymer microspheres, and can effectively improve the adsorption performance of the resin and reduce the risk of falling particles.
(3) Biocompatibility of
Part 4 of the biological evaluation of medical devices according to GB/T16886.4-2003: the hemolysis rate of the adsorbent was selectively evaluated in the blood interaction test, and the test results are shown in table 1.
TABLE 1 adsorbent hemolysis rate
As shown in Table 1, the hemolysis rate of the adsorbent provided by the invention is lower than 2%, meets the requirement of 5%, and has better biocompatibility.
As described above, the basic principles, main features and advantages of the present invention are better described. The above examples and description are merely illustrative of preferred embodiments of the present invention, and the present invention is not limited to the above examples, and various changes and modifications to the technical solution of the present invention by those skilled in the art should fall within the scope of protection defined by the present invention without departing from the spirit and scope of the present invention.

Claims (8)

1. A method for preparing a resin for protein adsorption, comprising: swelling polystyrene-divinylbenzene polymer microspheres by N, N-dimethylformamide, mixing the microspheres with thiourea solution, and carrying out hydrothermal reaction to obtain a thiourea modified resin carrier;
and soaking the thiourea modified resin carrier in carnosic acid solution, and finally placing the thiourea modified resin carrier in a mixed solution of polylysine and polyethyleneimine.
2. The method for preparing a resin for protein adsorption according to claim 1, wherein the concentration of the thiourea solution is 10-20 wt%, and the solvent of the thiourea solution is water;
and the ratio of the swelled polystyrene-divinylbenzene polymer microspheres to the thiourea solution is 1:20-30 in terms of g/mL.
3. The method for preparing a resin for protein adsorption according to claim 2, wherein the hydrothermal reaction is carried out at a temperature of 150-200 ℃ for a time of 12-48 hours.
4. The method for preparing the resin for protein adsorption according to claim 1, wherein the concentration of the carnosic acid solution is 20-30wt%, and the solvent of the carnosic acid solution is ethanol;
and the ratio of the thiourea modified resin carrier to the carnosic acid solution is 1:10-20 in terms of g/mL.
5. The method for preparing a resin for protein adsorption according to claim 4, wherein the soaking temperature is 50-60 ℃, and the soaking time is 8-16 h.
6. The method for preparing a resin for protein adsorption according to claim 1, wherein the concentration of polylysine in the mixed solution of polylysine and polyethyleneimine is 3-10wt%, and the concentration of polyethyleneimine is 3-10wt%.
7. The method for preparing a resin for protein adsorption according to claim 6, wherein the reaction temperature in the mixed solution of polylysine and polyethyleneimine is room temperature and the reaction time is 12-24 hours.
8. A resin for protein adsorption, characterized in that it is prepared by the method for preparing a resin for protein adsorption according to any one of claims 1 to 7.
CN202410061114.0A 2024-01-16 2024-01-16 Resin for protein adsorption and preparation method thereof Active CN117563570B (en)

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Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1615156A (en) * 2002-01-18 2005-05-11 先进菲涛尼克斯有限公司 Preparation of resinates
KR20090115515A (en) * 2008-05-02 2009-11-05 방민숙 A manufacturing method of adsorptive composition having antimicrobial and deodorant function
WO2013030838A2 (en) * 2011-08-29 2013-03-07 Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. Dendrimer-lyotropic liquid crystal (llc) systems
CN104525151A (en) * 2014-12-02 2015-04-22 佛山市博新生物科技有限公司 Endotoxin adsorbent used in hemoperfusion, and preparation method thereof
CN105709703A (en) * 2016-01-30 2016-06-29 浙江理工大学 Reparation and application of chelating resin and mercury ion detection method
CN112321838A (en) * 2020-10-22 2021-02-05 华东理工大学 Preparation method and application of nano polyethyleneimine grafted phenolic resin and photocatalytic hydrogen peroxide detection method
CN114288998A (en) * 2021-12-16 2022-04-08 健帆生物科技集团股份有限公司 Adsorption resin and preparation method and application thereof
CN115505166A (en) * 2022-09-23 2022-12-23 浙江工业大学 Thiourea modified resin-based nano material, preparation method and method for deeply removing selenate in water by using same
CN117123198A (en) * 2023-09-27 2023-11-28 佛山市博新生物科技有限公司 Modification method of blood purification adsorption material

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1615156A (en) * 2002-01-18 2005-05-11 先进菲涛尼克斯有限公司 Preparation of resinates
KR20090115515A (en) * 2008-05-02 2009-11-05 방민숙 A manufacturing method of adsorptive composition having antimicrobial and deodorant function
WO2013030838A2 (en) * 2011-08-29 2013-03-07 Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. Dendrimer-lyotropic liquid crystal (llc) systems
CN104525151A (en) * 2014-12-02 2015-04-22 佛山市博新生物科技有限公司 Endotoxin adsorbent used in hemoperfusion, and preparation method thereof
CN105709703A (en) * 2016-01-30 2016-06-29 浙江理工大学 Reparation and application of chelating resin and mercury ion detection method
CN112321838A (en) * 2020-10-22 2021-02-05 华东理工大学 Preparation method and application of nano polyethyleneimine grafted phenolic resin and photocatalytic hydrogen peroxide detection method
CN114288998A (en) * 2021-12-16 2022-04-08 健帆生物科技集团股份有限公司 Adsorption resin and preparation method and application thereof
CN115505166A (en) * 2022-09-23 2022-12-23 浙江工业大学 Thiourea modified resin-based nano material, preparation method and method for deeply removing selenate in water by using same
CN117123198A (en) * 2023-09-27 2023-11-28 佛山市博新生物科技有限公司 Modification method of blood purification adsorption material

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