CN114225922A - Low-density lipoprotein adsorbent and efficient preparation method thereof - Google Patents
Low-density lipoprotein adsorbent and efficient preparation method thereof Download PDFInfo
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Abstract
The invention provides a low-density lipoprotein adsorbent and a high-efficiency preparation method thereof, S1 takes polystyrene adsorption resin and adds a swelling agent for full swelling; s2, adding a catalyst A and an epoxy reagent into the swelled polystyrene adsorption resin to carry out ring opening reaction to obtain hydroxylated polystyrene adsorption resin; s3, sequentially carrying out ring-opening and ring-closing reactions on the hydroxylated polystyrene adsorbent resin and epichlorohydrin, and cleaning to obtain the epoxidized polystyrene adsorbent resin; s4 is coupled with polyanion ligand under the action of catalyst B, and is washed to obtain the low-density lipoprotein adsorbent; the catalyst B is one of magnesium chloride, aluminum chloride and ferric bromide. The invention improves the reaction efficiency by respectively adding specific catalysts in the hydroxylation reaction and the coupling reaction of the polystyrene resin, and obviously improves the compatibility with blood and the specific adsorption of low-density lipoprotein by the design of a specific hydrophobic chain.
Description
Technical Field
The invention relates to the technical field of blood adsorbents, in particular to a low-density lipoprotein adsorbent and an efficient preparation method thereof.
Background
Blood adsorption, also known as hemoperfusion, refers to a treatment method in which blood is introduced into a container filled with a fixed adsorbent by means of extracorporeal circulation equipment, and some exogenous and endogenous harmful substances are adsorbed and removed, so as to purify the blood. The selection of the carrier and the ligand and the preparation method of the adsorbent are the core technology of blood adsorption. Polystyrene resin is a carrier which is widely applied in China at present, has large production scale, is low in price, can greatly reduce the overall cost when being used as an adsorbent carrier, but is difficult to activate and modify the surface and couple with macromolecular substances.
Patent CN105032358A discloses an amphiphilic low-density lipoprotein adsorbent and a preparation method thereof, wherein polystyrene divinyl benzene resin is added into acetone solution of m-chloroperoxybenzoic acid for epoxidation modification, and then ligand is coupled to obtain the adsorbent. But the acetone belongs to a tube product, the operation process is dangerous, the workshop scale-up production is not facilitated, and the clearance rate of the prepared adsorbent is below 60%.
Patent CN104492402A discloses a method for preparing an adsorbent for adsorbing low-density lipoprotein for whole blood perfusion, which sequentially performs chloromethylation modification, hydroxylation modification and epoxy activation on macroporous polystyrene resin, and the reaction steps are complex, the preparation efficiency and yield are low, the adsorption rate on low-density lipoprotein is not good, and the preparation is not beneficial to large-scale preparation.
In view of the above, there is a need to design an improved low density lipoprotein adsorbent and a highly efficient preparation method thereof to solve the above problems.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention aims to provide a low-density lipoprotein adsorbent and an efficient preparation method thereof.
In order to achieve the above object, the present invention provides a method for efficiently preparing a low density lipoprotein adsorbent, comprising the steps of:
s1, adding a swelling agent into polystyrene adsorption resin for full swelling;
s2, adding a catalyst A and an epoxy reagent into the swelled polystyrene adsorption resin to perform a ring opening reaction to obtain a hydroxylated polystyrene adsorption resin;
s3, carrying out an open-loop grafting reaction on the hydroxylated polystyrene adsorbent resin and epichlorohydrin, carrying out a closed-loop reaction, and cleaning to obtain an epoxidized polystyrene adsorbent resin;
s4, mixing the epoxidized polystyrene adsorbent resin with a polyanion ligand solution, adding a catalyst B, carrying out coupling reaction, and cleaning to obtain a low-density lipoprotein adsorbent; the catalyst B is one of magnesium chloride, aluminum chloride and ferric bromide.
As a further improvement of the present invention, in step S2, the catalyst a is tetrabutylammonium bromide or ferrous bromide.
As a further improvement of the invention, in step S2, the molar ratio of the polystyrene adsorbent resin to the catalyst A and the epoxy reagent is 1 (0.2-1) to (2-10).
As a further improvement of the present invention, in step S2, the epoxy reagent is propylene oxide.
As a further improvement of the present invention, in step S3, the ring-opening grafting catalyst is boron trifluoride diethyl etherate, and the ring-closing catalyst is sodium hydroxide.
In a further improvement of the present invention, in step S3, the resin is sequentially washed with methanol or ethanol, 0.1 to 0.5mol/L hydrochloric acid, and purified water to obtain the epoxidized polystyrene-based adsorbent resin.
In a further improvement of the present invention, in step S4, the molar ratio of the epoxidized polystyrene-based adsorbent resin to the catalyst B is 1 (0.02-0.5).
As a further improvement of the invention, in step S4, the mass-to-volume ratio of the epoxidized polystyrene-based adsorbent resin to the polyanion ligand solution is 1g (1-4) mL; the concentration of the polyanionic ligand solution is 100-300 mg/mL.
As a further improvement of the present invention, in step S4, the polyanionic ligand is one or more of dextran sulfate, heparin or heparin derivatives.
As a further improvement of the present invention, in step S1, the swelling agent is dichloroethane.
The invention also provides a low-density lipoprotein adsorbent prepared by any one of the preparation methods.
The invention has the beneficial effects that:
1. the low-density lipoprotein adsorbent provided by the invention adopts epoxypropane and reduced chloropropane in sequence to realize epoxidation modification of polystyrene adsorbent resin, and then polyanion ligand coupling is carried out. By doing so, the obtained low density lipoprotein adsorbent has good compatibility with blood, not only has high adsorption rate to low density lipoprotein in blood, but also has weak adsorption to other non-low density lipoprotein substances, thus having good effect of removing low density lipoprotein in blood.
2. In the high-efficiency preparation method of the low-density lipoprotein adsorbent, one of magnesium chloride, aluminum chloride and ferric bromide is added as a catalyst B in the coupling reaction, the magnesium chloride, the aluminum chloride and the ferric bromide belong to Lewis acid with metal ions of 2-valent or 3-valent, an aqueous solution is acidic or weakly acidic, and can form a complex with a specific substance in the reaction so as to catalyze the reaction, so that the efficiency of the coupling reaction can be improved, and the high-efficiency adsorbent is obtained.
3. In the invention, one of tetrabutylammonium bromide and ferrous bromide is added as a catalyst A in the hydroxylation reaction process of propylene oxide, so that the adsorbent with higher efficiency can be prepared.
4. After the hydroxylation reaction, the adsorbent is sequentially washed by methanol or ethanol, 0.1-0.5 mol/L hydrochloric acid and purified water, if 0.1-0.5 mol/L hydrochloric acid is lacked in the washing step, the adsorption efficiency of the adsorbent is directly influenced, probably because reagents or reaction byproducts of the hydroxylation reaction cannot be washed clean by the methanol or the ethanol and the purified water, the coupling reaction is influenced, and the influence can be avoided by adding 0.1-0.5 mol/L hydrochloric acid for washing.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is described in detail below with reference to specific embodiments.
It should be noted that, in order to avoid obscuring the present invention with unnecessary details, only the structures and/or processing steps closely related to the scheme of the present invention are shown in the specific embodiments, and other details not closely related to the present invention are omitted.
In addition, it is also to be noted that 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 invention provides a high-efficiency preparation method of a low-density lipoprotein adsorbent, which comprises the following steps:
s1, adding a swelling agent into polystyrene adsorption resin for full swelling; the swelling agent is dichloroethane.
S2, adding a catalyst A and an epoxy reagent into the swelled polystyrene adsorption resin to perform a ring opening reaction to obtain the hydroxylated polystyrene adsorption resin, which is shown in the following formula.
In step S2, the catalyst a is tetrabutylammonium bromide or ferrous bromide. The molar ratio of the polystyrene adsorption resin to the catalyst A and the epoxy reagent is 1 (0.2-1) to 2-10. The epoxy reagent is propylene oxide. By adding tetrabutylammonium bromide or ferrous bromide, the substitution reaction of the propylene oxide and the polystyrene can be efficiently catalyzed, and the hydroxyethyl polystyrene resin is obtained.
And S3, carrying out an open-loop grafting reaction on the hydroxylated polystyrene adsorbent resin and epichlorohydrin, carrying out a closed-loop reaction, and cleaning to obtain the epoxidized polystyrene adsorbent resin, which is shown in the following formula. Wherein, the catalyst of the ring-opening grafting reaction is boron trifluoride diethyl etherate, and epoxy groups and hydroxyl groups are subjected to ring-opening grafting to form propyl ether containing hydroxyl and chlorine; the catalyst for ring closure reaction is sodium hydroxide, and hydroxyl and chlorine are removed under alkaline condition to form epoxy group again. In step S3, sequentially washing with methanol or ethanol, 0.1-0.5 mol/L hydrochloric acid and purified water to obtain the epoxidized polystyrene-based adsorption resin, wherein the structure has a certain hydrophobic chain and good compatibility with blood, and can well adsorb low-density lipoprotein in blood after being grafted with polyanionic ligand.
S4, mixing the epoxidized polystyrene adsorbent resin with a polyanion ligand solution, adding a catalyst B, carrying out coupling reaction, and cleaning to obtain a low-density lipoprotein adsorbent; the catalyst B is one of magnesium chloride, aluminum chloride and ferric bromide.
In step S4, the molar ratio of the epoxidized polystyrene-based adsorbent resin to the catalyst B is 1 (0.02 to 0.5). In step S4, the mass-to-volume ratio of the epoxidized polystyrene-based adsorbent resin to the polyanion ligand solution is 1g (1-4) mL; the concentration of the polyanionic ligand solution is 100-300 mg/mL. In step S4, the polyanionic ligand is one or more of dextran sulfate, heparin, or a heparin-like derivative.
The invention also provides a low-density lipoprotein adsorbent prepared by any one of the preparation methods.
Example 1
A high-efficiency preparation method of a low-density lipoprotein adsorbent comprises the following steps:
(1) adding 10g of polystyrene resin into 50mL of dichloroethane, soaking overnight to fully swell the resin, adding tetrabutylammonium bromide and propylene oxide, wherein the molar ratio of the polystyrene resin to the tetrabutylammonium bromide to the propylene oxide is 1:0.5:5, stirring at 60 ℃ to react for 8 hours for ring-opening reaction, and washing with methanol, 0.1mol/L hydrochloric acid and purified water in sequence after the reaction to obtain the hydroxylated polystyrene resin.
(2) Carrying out ring-opening grafting on hydroxylated polystyrene resin and epoxy chloropropane under the catalytic action of boron trifluoride diethyl etherate; then adding 1M NaOH solution (the ratio of the hydroxylated polystyrene resin, the epichlorohydrin to the NaOH solution is 1g:0.5mL:1.5mL), placing at 40 ℃ for reaction for 2h, and washing with purified water to obtain the epoxidized polystyrene resin.
(3) Mixing the epoxidized polystyrene resin with a heparin solution (200mg/mL) in a ratio of 1g to 2mL, adding magnesium chloride, wherein the molar ratio of the epoxidized polystyrene resin to the magnesium chloride is 1:0.2, placing the mixture at 50 ℃ for coupling reaction for 16 hours, and then fully washing the mixture with purified water and saline and pumping the mixture to obtain the low-density lipoprotein adsorbent.
Example 2
Compared with the embodiment 1, the difference of the high-efficiency preparation method of the low-density lipoprotein adsorbent is that the catalyst in the step (1) is ferrous bromide, and the molar ratio of the polystyrene resin to the ferrous bromide to the propylene oxide is 1:1: 5. The rest is substantially the same as that of embodiment 1, and will not be described herein.
Example 3
Compared with the embodiment 1, the difference of the high-efficiency preparation method of the low-density lipoprotein adsorbent is that the molar ratio of the polystyrene resin, the tetrabutylammonium bromide and the propylene oxide in the step (1) is 1:1: 10. The rest is substantially the same as that of embodiment 1, and will not be described herein.
Example 4
Compared with the embodiment 1, the difference of the high-efficiency preparation method of the low-density lipoprotein adsorbent is that the molar ratio of the polystyrene resin, the tetrabutylammonium bromide and the propylene oxide in the step (1) is 1:0.2: 2. The rest is substantially the same as that of embodiment 1, and will not be described herein.
Example 5
A method for efficiently producing a low-density lipoprotein adsorbent, which is different from example 1 in that magnesium chloride in step (3) is replaced with aluminum chloride. The rest is substantially the same as that of embodiment 1, and will not be described herein.
Example 6
A method for efficiently producing a low-density lipoprotein adsorbent, which is different from example 1 in that magnesium chloride in step (3) is replaced with ferric bromide. The rest is substantially the same as that of embodiment 1, and will not be described herein.
Example 7
A high-efficiency preparation method of a low-density lipoprotein adsorbent is different from the method of example 1 in that the molar ratio of the epoxidized polystyrene resin to the magnesium chloride in the step (3) is 1: 0.5. The rest is substantially the same as that of embodiment 1, and will not be described herein.
Example 8
A high-efficiency preparation method of a low-density lipoprotein adsorbent is different from the method of example 1 in that the molar ratio of the epoxidized polystyrene resin to the magnesium chloride in the step (3) is 1: 0.02. The rest is substantially the same as that of embodiment 1, and will not be described herein.
Example 9
A method for efficiently producing a low-density lipoprotein adsorbent, which is different from that of example 1 in that heparin in step (3) is replaced with a dextran sulfate solution (200 mg/mL). The rest is substantially the same as that of embodiment 1, and will not be described herein.
Comparative example 1
A method for efficiently preparing a low-density lipoprotein adsorbent, which is different from that of example 1 in that magnesium chloride is not added in step (3). The rest is substantially the same as that of embodiment 1, and will not be described herein.
Comparative example 2
A method for efficiently producing a low-density lipoprotein adsorbent, which is different from that of example 1 in that a heparin solution in example 1 is grafted by a method similar to that in step (3) of example 1 after vinyl epoxidation of a polyethylene divinylbenzene resin using m-chloroperoxybenzoic acid. The rest is substantially the same as that of embodiment 1, and will not be described herein.
Comparative example 3
A method for efficiently preparing a low-density lipoprotein adsorbent, which is different from comparative example 2 in that magnesium chloride is not added in step (3). The rest is substantially the same as in comparative example 2 and will not be described again.
Comparative example 4
Compared with the embodiment 1, the difference of the high-efficiency preparation method of the low-density lipoprotein adsorbent is that the hydroxylated polystyrene resin is obtained by sequentially washing the low-density lipoprotein adsorbent with methanol and purified water in the step (1), namely, hydrochloric acid is not adopted for washing. The rest is substantially the same as that of embodiment 1, and will not be described herein.
The low-density lipoprotein adsorbents obtained in the examples and comparative examples were measured for their adsorption rates to LDL-C, which were determined by the following test methods: weighing 0.50g of the drained adsorbent into a 10mL centrifuge tube or a triangular flask, adding 2.5mL of plasma, placing on a shaker at constant temperature of 37 ℃, shaking at 120rpm for 2h, centrifuging at 3000r/min for 5min, sampling, and sucking supernatant to be tested; measuring the content of low-density lipoprotein (LDL-C) in the plasma before and after adsorption by using a low-density lipoprotein cholesterol detection kit and a full-automatic biochemical analyzer; by the formula (C)b-Ca)×100％/CbCalculating the adsorption rate of the adsorbent to the low-density lipoprotein LDL-C (C)b-low density lipoprotein cholesterol content in plasma prior to adsorption; caLow density lipoprotein cholesterol content in plasma after 2h of adsorption). The adsorption rate of the adsorbent to high density lipoprotein HDL was measured by the same principle, and the results of comparing the adsorption rates of examples 1 to 9 and comparative examples 1 to 3 are shown in Table 1.
TABLE 1 results of adsorption rate test for examples 1 to 9 and comparative examples 1 to 4
| Adsorbent and process for producing the same | Adsorption Rate of LDL-C | Adsorption Rate of HDL |
| Example 1 | 66.1％ | 5.3％ |
| Example 2 | 57.8％ | 5.1％ |
| Example 3 | 51.1％ | 6.0％ |
| Example 4 | 46.9％ | 5.3％ |
| Example 5 | 65.5％ | 5.3％ |
| Example 6 | 66.3％ | 5.7％ |
| Example 7 | 52.3％ | 5.7％ |
| Example 8 | 40.5％ | 6.2％ |
| Example 9 | 68.2％ | 5.1％ |
| Comparative example 1 | 30.2％ | 7.5％ |
| Comparative example 2 | 45.4％ | 12.5％ |
| Comparative example 3 | 25.7％ | 13.6％ |
| Comparative example 4 | 36.3％ | 15.9％ |
As can be seen from examples 1, 6 to 9 and comparative example 1, when two polyanionic compounds heparin and dextran sulfate were used as ligands, the coupling reaction efficiency could be significantly improved by adding a specific catalyst, and the adsorption rate of LDL-C by the prepared adsorbent could be significantly improved because the specific catalyst formed a complex with a specific substance to catalyze the reaction. A comparison of examples 1 and 6-8 shows that the molar ratio of epoxidized carrier to catalyst B is optimally 1: 0.2.
From the example 1 and the comparative examples 2 to 3, it can be seen that epoxy propane and epoxy chloropropane are sequentially adopted to realize epoxidation modification of polystyrene adsorbent resin, and then polyanion ligands are coupled, so that the obtained low-density lipoprotein adsorbent has good compatibility with blood, not only has higher adsorption rate on low-density lipoprotein in blood, but also has weaker adsorption on other non-low-density lipoprotein substances, and therefore, the removal effect on the low-density lipoprotein in blood is better.
The comparison between the example 1 and the comparative example 4 shows that the adsorption rate of the adsorbent can be obviously improved by adding hydrochloric acid during cleaning, the non-specific adsorption (adsorption rate of HDL) of the adsorbent can be reduced, the reagent or the reaction byproduct of the previous step reaction cannot be cleaned by using methanol or ethanol or purified water, so that the subsequent reaction is influenced, and the influence can be avoided by adding 0.1-0.5 mol/L hydrochloric acid for cleaning.
In conclusion, the invention adopts epoxypropane and epichlorohydrin to realize epoxidation modification of the polystyrene adsorbent resin in sequence, and then polyanion ligand is coupled. By doing so, the obtained low density lipoprotein adsorbent has good compatibility with blood, not only has high adsorption rate to low density lipoprotein in blood, but also has weak adsorption to other non-low density lipoprotein substances, thus having good effect of removing low density lipoprotein in blood. By respectively adding specific catalysts in the hydroxylation reaction and the coupling reaction of the polystyrene resin and adding the step of washing with hydrochloric acid in the washing process, the reaction efficiency is improved, and the adsorption efficiency of the prepared adsorbent is improved.
Although the present invention has been described in detail with reference to the preferred embodiments, it will be understood by those skilled in the art that various changes may be made and equivalents may be substituted for elements thereof without departing from the spirit and scope of the present invention.
Claims (10)
1. A high-efficiency preparation method of a low-density lipoprotein adsorbent is characterized by comprising the following steps:
s1, adding a swelling agent into polystyrene adsorption resin for full swelling;
s2, adding a catalyst A and an epoxy reagent into the swelled polystyrene adsorption resin to perform a ring opening reaction to obtain a hydroxylated polystyrene adsorption resin;
s3, carrying out an open-loop grafting reaction on the hydroxylated polystyrene adsorbent resin and epichlorohydrin, carrying out a closed-loop reaction, and cleaning to obtain an epoxidized polystyrene adsorbent resin;
s4, mixing the epoxidized polystyrene adsorbent resin with a polyanion ligand solution, adding a catalyst B, carrying out coupling reaction, and cleaning to obtain a low-density lipoprotein adsorbent; the catalyst B is one of magnesium chloride, aluminum chloride and ferric bromide.
2. The method for efficiently producing the low-density lipoprotein adsorbent of claim 1 wherein in step S2, the catalyst a is tetrabutylammonium bromide or ferrous bromide and the epoxy agent is propylene oxide.
3. The method for efficiently producing the low-density lipoprotein adsorbent of claim 1, wherein in step S2, the molar ratio of the polystyrene-based adsorption resin to the catalyst A and the epoxy agent is 1 (0.2-1) to (2-10).
4. The method for efficiently producing the low-density lipoprotein adsorbent of claim 1 wherein in step S3, the ring-opening grafting catalyst is boron trifluoride ethyl ether and the ring-closing catalyst is sodium hydroxide.
5. The method for efficiently producing the low-density lipoprotein adsorbent of claim 1, wherein the epoxidized polystyrene-based adsorbent resin is obtained by washing with methanol or ethanol, 0.1 to 0.5mol/L hydrochloric acid and purified water in sequence in step S3.
6. The method for efficiently producing a low-density lipoprotein adsorbent according to claim 1, wherein in step S4, the molar ratio of the epoxidized polystyrene-based adsorbent resin to the catalyst B is 1 (0.02-0.5).
7. The method for efficiently preparing the low-density lipoprotein adsorbent of claim 1, wherein in step S4, the mass-to-volume ratio of the epoxidized polystyrene-based adsorbent resin to the polyanionic ligand solution is 1g (1-4) mL; the concentration of the polyanionic ligand solution is 100-300 mg/mL.
8. The method of claim 1, wherein in step S4, the polyanionic ligand is one or more of dextran sulfate, heparin or heparin derivatives.
9. The method for efficiently producing the low-density lipoprotein adsorbent of claim 1 wherein the swelling agent is dichloroethane in step S1.
10. A low-density lipoprotein adsorbent produced by the production method according to any one of claims 1 to 9.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104492402A (en) * | 2014-12-31 | 2015-04-08 | 珠海健帆生物科技股份有限公司 | Preparation method of adsorbent for adsorbing low-density lipoprotein (LDL) for whole blood perfusion |
| CN104525155A (en) * | 2014-12-31 | 2015-04-22 | 珠海健帆生物科技股份有限公司 | Adsorbent used for absorbing low density lipoprotein (LDL) in whole blood perfusion and preparation method of adsorbent |
| CN105032358A (en) * | 2015-06-19 | 2015-11-11 | 佛山市博新生物科技有限公司 | Amphipathic low-density lipoprotein adsorbent and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104492402A (en) * | 2014-12-31 | 2015-04-08 | 珠海健帆生物科技股份有限公司 | Preparation method of adsorbent for adsorbing low-density lipoprotein (LDL) for whole blood perfusion |
| CN104525155A (en) * | 2014-12-31 | 2015-04-22 | 珠海健帆生物科技股份有限公司 | Adsorbent used for absorbing low density lipoprotein (LDL) in whole blood perfusion and preparation method of adsorbent |
| CN105032358A (en) * | 2015-06-19 | 2015-11-11 | 佛山市博新生物科技有限公司 | Amphipathic low-density lipoprotein adsorbent and preparation method thereof |
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Inventor after: Zhang Yuan Inventor after: Yu Zengcheng Inventor after: Wang Yefu Inventor before: Zhang Yuan Inventor before: Zhang Lei Inventor before: Chen Menglin Inventor before: Yu Zengcheng Inventor before: Wang Yefu |
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