CN114225922B - 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, wherein S1, polystyrene adsorption resin is taken, and a swelling agent is added 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 a hydroxylated polystyrene adsorption resin; s3, sequentially carrying out ring opening and ring closing reactions on the hydroxylated polystyrene adsorption resin and epichlorohydrin, and cleaning to obtain the epoxidized polystyrene adsorption resin; s4, performing a coupling reaction with a polyanion ligand under the action of a catalyst B, and cleaning to obtain the low-density lipoprotein adsorbent; the catalyst B is one of magnesium chloride, aluminum chloride and ferric bromide. According to the invention, the specific catalysts are respectively added in the hydroxylation reaction and the coupling reaction of the polystyrene resin, so that the reaction efficiency is improved, and the compatibility with blood and the specific adsorption of the low-density lipoprotein are remarkably improved through the design of the 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 a high-efficiency preparation method thereof.
Background
Blood adsorption, also known as blood perfusion, refers to a therapeutic method in which blood is introduced into a vessel containing a fixed adsorbent by means of extracorporeal circulation equipment, and certain exogenous and endogenous harmful substances are removed by adsorption, thereby achieving blood purification. Wherein, the selection of the carrier and the ligand and the preparation method of the adsorbent are core technologies of blood adsorption. The polystyrene resin is a carrier with wider domestic application at present, and has large production scale, so the price is lower, and when the polystyrene resin is used as an adsorbent carrier, the whole cost can be greatly reduced, but the surface activation modification and the coupling with macromolecular substances are difficult.
Patent CN105032358A discloses an amphiphilic low-density lipoprotein adsorbent and a preparation method thereof, wherein polystyrene divinylbenzene resin is added with acetone solution of m-chloroperoxybenzoic acid for epoxidation modification, and ligand is coupled to obtain the adsorbent. However, acetone belongs to a pipe product, the operation process is dangerous, the workshop scale-up production is not facilitated, and the clearance of the prepared adsorbent is below 60%.
Patent CN104492402a discloses a preparation method of an adsorbent for adsorbing low-density lipoprotein for whole blood perfusion, which sequentially carries out chloromethylation modification, hydroxylation modification and epoxy activation on macroporous polystyrene resin, and has the advantages of complex reaction steps, low preparation efficiency and yield, poor adsorption rate on low-density lipoprotein and no contribution to large-scale preparation.
In view of the foregoing, there is a need for an improved low density lipoprotein adsorbent and 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 the low-density lipoprotein adsorbent and the efficient preparation method thereof, wherein the epoxy modification of the polystyrene adsorption resin is realized by sequentially adopting the epoxypropane and the epoxychloropropane, then the polyanion ligand is coupled, the preparation efficiency is improved by adding a specific catalyst, and the compatibility with blood and the specific adsorption effect on the low-density lipoprotein are obviously improved by the design of a specific hydrophobic chain.
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 to fully swell;
s2, adding a catalyst A and an epoxy reagent into the swelled polystyrene adsorption resin to carry out ring-opening reaction to obtain a hydroxylated polystyrene adsorption resin;
s3, performing ring-opening grafting reaction on the hydroxylated polystyrene adsorption resin and epoxy chloropropane, then performing ring-opening reaction, and cleaning to obtain the epoxidized polystyrene adsorption resin;
s4, mixing the epoxidized polystyrene adsorption resin with a polyanion ligand solution, adding a catalyst B, performing a 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 the step S2, the molar ratio of the polystyrene adsorption resin to the catalyst A to the epoxy agent is 1 (0.2-1): 2-10.
As a further improvement of the present invention, in step S2, the epoxy agent is propylene oxide.
As a further improvement of the invention, in the step S3, the catalyst of the ring-opening grafting reaction is boron trifluoride diethyl ether, and the catalyst of the ring-closing reaction is sodium hydroxide.
As a further improvement of the present invention, in step S3, 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 this order.
As a further improvement of the present invention, in the step S4, the molar ratio of the epoxidized polystyrene-based adsorbent resin to the catalyst B is 1 (0.02 to 0.5).
As a further improvement of the invention, in the step S4, the mass-volume ratio of the epoxidized polystyrene adsorbent resin to the polyanion ligand solution is 1g (1-4) mL; the concentration of the polyanion 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-like 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 the preparation method of any one of the above.
The beneficial effects of the invention are as follows:
1. the low-density lipoprotein adsorbent provided by the invention realizes the epoxidation modification of polystyrene adsorption resin by sequentially adopting propylene oxide and epichlorohydrin, and then is coupled with polyanion ligand. In this way, the obtained low-density lipoprotein adsorbent has good compatibility with blood, has high adsorption rate on low-density lipoprotein in blood, and has weak adsorption on other non-low-density lipoprotein substances, so that the low-density lipoprotein adsorbent has good effect of removing the low-density lipoprotein in the 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 a coupling reaction, the three are Lewis acids with 2-valence or 3-valence metal ions, and an aqueous solution is acidic or weak-acid, and can form a complex with a specific substance in the reaction, so that the reaction is catalyzed, and the efficiency of the coupling reaction is improved, thereby obtaining the high-efficiency adsorbent.
3. In the process of hydroxylation reaction by propylene oxide, one of tetrabutylammonium bromide and ferrous bromide is added as a catalyst A, so that the adsorbent with higher efficiency can be prepared.
4. After the hydroxylation reaction, methanol or ethanol, 0.1-0.5 mol/L hydrochloric acid and purified water are used for cleaning in sequence, if 0.1-0.5 mol/L hydrochloric acid is absent in the cleaning step, the adsorption efficiency of the adsorbent is directly influenced, and the coupling reaction is possibly influenced because reagents or reaction byproducts of the hydroxylation reaction cannot be cleaned by using the methanol or ethanol and the purified water only, and the effect can be avoided by adding 0.1-0.5 mol/L hydrochloric acid for cleaning.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention will be described in detail with reference to specific embodiments.
It should be further noted that, in order to avoid obscuring the present invention due to unnecessary details, only structures and/or processing steps closely related to aspects of the present invention are shown in the specific embodiments, and other details not greatly related to the present invention are omitted.
In addition, it should be further 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 to fully swell; the swelling agent is dichloroethane.
S2, adding a catalyst A and an epoxy reagent into the swelled polystyrene adsorption resin to carry out ring-opening reaction, so as to obtain the hydroxylated polystyrene adsorption resin, wherein the formula is shown below.
In step S2, the catalyst a is tetrabutylammonium bromide or ferrous bromide. The molar ratio of the polystyrene adsorption resin to the catalyst A to the epoxy agent is 1 (0.2-1) to 2-10. The epoxy agent is propylene oxide. By adding tetrabutylammonium bromide or ferrous bromide, the substitution reaction of propylene oxide and polystyrene can be efficiently catalyzed, and the hydroxyethyl polystyrene resin is obtained.
S3, performing ring-opening grafting reaction on the hydroxylated polystyrene adsorption resin and epoxy chloropropane, then performing ring-opening reaction, and cleaning to obtain the epoxidized polystyrene adsorption resin, wherein the formula is shown below. Wherein the catalyst of the ring-opening grafting reaction is boron trifluoride diethyl ether, epoxy groups and hydroxyl groups are subjected to ring-opening grafting to form propyl ether containing hydroxyl groups and chlorine; the catalyst of ring closure reaction is sodium hydroxide, and hydroxy and chlorine are removed under alkaline condition to reform epoxy group. In the step S3, methanol or ethanol, 0.1-0.5 mol/L hydrochloric acid and purified water are sequentially used for cleaning to obtain the epoxidized polystyrene adsorption resin, and the structure has a certain hydrophobic chain, has good compatibility with blood, and can well adsorb the low-density lipoprotein in the blood after being grafted with polyanion ligand.
S4, mixing the epoxidized polystyrene adsorption resin with a polyanion ligand solution, adding a catalyst B, performing a 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 the step S4, the molar ratio of the epoxidized polystyrene adsorbent resin to the catalyst B is 1 (0.02 to 0.5). In the step S4, the mass volume ratio of the epoxidized polystyrene adsorption resin to the polyanion ligand solution is 1g (1-4) mL; the concentration of the polyanion ligand solution is 100-300 mg/mL. In step S4, the polyanionic ligand is one or more of dextran sulfate, heparin, or heparin-like derivatives.
The invention also provides a low-density lipoprotein adsorbent prepared by the preparation method of any one of the above.
Example 1
A high-efficiency preparation method of a low-density lipoprotein adsorbent comprises the following steps:
(1) 10g of polystyrene resin is taken, 50mL of dichloroethane is added for soaking overnight to fully swell the resin, tetrabutylammonium bromide and propylene oxide are added, the molar ratio of the polystyrene resin to the tetrabutylammonium bromide to the propylene oxide is 1:0.5:5, the polystyrene resin is stirred at 60 ℃ for 8 hours for carrying out ring opening reaction, and methanol, 0.1mol/L hydrochloric acid and purified water are sequentially used for washing after the reaction to obtain the hydroxylated polystyrene resin.
(2) The method comprises the steps of (1) carrying out ring-opening grafting on hydroxylated polystyrene resin and epoxy chloropropane under the catalysis of boron trifluoride diethyl ether; then, a 1M NaOH solution (ratio of hydroxylated polystyrene resin, epichlorohydrin to NaOH solution: 1g:0.5mL:1.5 mL) was added, and the mixture was allowed to react at 40℃for 2 hours, and after washing with purified water, an epoxidized polystyrene resin was obtained.
(3) Mixing the epoxidized polystyrene resin and heparin solution (200 mg/mL) in a ratio of 1g to 2mL, adding magnesium chloride, placing the mixture in a coupling reaction at 50 ℃ for 16h, and then fully washing with purified water and saline water and pumping to obtain the low-density lipoprotein adsorbent.
Example 2
Compared with the embodiment 1, the high-efficiency preparation method of the low-density lipoprotein adsorbent is different in 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 other points are substantially the same as those of embodiment 1, and will not be described here again.
Example 3
The efficient preparation method of the low-density lipoprotein adsorbent is different from the embodiment 1 in that the molar ratio of the polystyrene resin to tetrabutylammonium bromide to propylene oxide in the step (1) is 1:1:10. The other points are substantially the same as those of embodiment 1, and will not be described here again.
Example 4
The efficient preparation method of the low-density lipoprotein adsorbent is different from the embodiment 1 in that the molar ratio of the polystyrene resin to tetrabutylammonium bromide to propylene oxide in the step (1) is 1:0.2:2. The other points are substantially the same as those of embodiment 1, and will not be described here again.
Example 5
An efficient preparation method of a low-density lipoprotein adsorbent is different from example 1 in that magnesium chloride in step (3) is replaced with aluminum chloride. The other points are substantially the same as those of embodiment 1, and will not be described here again.
Example 6
An efficient method for preparing a low density lipoprotein adsorbent, which is different from example 1 in that magnesium chloride in step (3) is replaced with ferric bromide. The other points are substantially the same as those of embodiment 1, and will not be described here again.
Example 7
The efficient preparation method of the low-density lipoprotein adsorbent is different from the embodiment 1 in that the molar ratio of the epoxidized polystyrene resin to the magnesium chloride in the step (3) is 1:0.5. The other points are substantially the same as those of embodiment 1, and will not be described here again.
Example 8
The efficient preparation method of the low-density lipoprotein adsorbent is different from the embodiment 1 in that the molar ratio of the epoxidized polystyrene resin to the magnesium chloride in the step (3) is 1:0.02. The other points are substantially the same as those of embodiment 1, and will not be described here again.
Example 9
A method for efficiently producing a low-density lipoprotein adsorbent, which differs from example 1 in that heparin in step (3) is replaced with a dextran sulfate solution (200 mg/mL). The other points are substantially the same as those of embodiment 1, and will not be described here again.
Comparative example 1
A method for efficiently preparing a low-density lipoprotein adsorbent is different from example 1 in that magnesium chloride is not added in step (3). The other points are substantially the same as those of embodiment 1, and will not be described here again.
Comparative example 2
A method for efficiently producing a low-density lipoprotein adsorbent, which is different from example 1 in that a heparin solution in example 1 is grafted by the same method as in step (3) of example 1 after vinyl epoxidation of a polyethylene divinylbenzene resin using m-chloroperoxybenzoic acid. The other points are substantially the same as those of embodiment 1, and will not be described here again.
Comparative example 3
A method for efficiently preparing a low-density lipoprotein adsorbent is different from comparative example 2 in that magnesium chloride is not added in step (3). The other components are substantially the same as those of comparative example 2, and will not be described in detail here.
Comparative example 4
Compared with the embodiment 1, the high-efficiency preparation method of the low-density lipoprotein adsorbent is different in that the step (1) is sequentially washed by methanol and purified water to obtain the hydroxylated polystyrene resin, namely hydrochloric acid is not used for washing. The other points are substantially the same as those of embodiment 1, and will not be described here again.
The adsorption rate of LDL-C by the low-density lipoprotein adsorbent obtained in each of the examples and comparative examples was measured by the following method: weighing 0.50g of the pumped adsorbent, adding 2.5mL of plasma into a 10mL centrifuge tube or a triangular flask, placing on a shaking table with a constant temperature of 37 ℃ and shaking at 120rpm for 2 hours, centrifuging at 3000r/min for 5 minutes, sampling, and sucking the supernatant to be detected; determination of Low Density lipoprotein (LDL-C) content in plasma before and after adsorption Using Low Density lipoprotein cholesterol detection kit and full automatic Biochemical AnalyzerAn amount of; by the formula (C) b -C a )×100％/C b Calculating 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; c (C) a -low density lipoprotein cholesterol content in plasma after 2h of adsorption). The adsorption rate of the adsorbent on high density lipoprotein HDL was measured by the same principle, and the adsorption rates of examples 1 to 9 and comparative examples 1 to 3 were compared, and the results are shown in Table 1.
TABLE 1 adsorption test results for examples 1-9 and comparative examples 1-4
| 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, 6-9 and comparative example 1, when two polyanion compounds of heparin and dextran sulfate are used as ligands, the coupling reaction efficiency can be remarkably improved by adding a specific catalyst, and the adsorption rate of the prepared adsorbent to LDL-C is remarkably improved because the specific catalyst and a specific substance form a complex, thereby catalyzing the reaction. As can be seen from a comparison of examples 1 and 6-8, the molar ratio of epoxidized support to catalyst B is optimally 1:0.2.
From example 1 and comparative examples 2 to 3, it can be seen that the epoxypropane and the epoxychloropropane are sequentially used to realize the epoxidation modification of the polystyrene adsorption resin, and then the polyanion ligand is coupled, so that the obtained low-density lipoprotein adsorbent has good compatibility with blood, has higher adsorption rate on low-density lipoprotein in blood, and has weaker adsorptivity on other non-low-density lipoprotein substances, thus having better effect of removing the low-density lipoprotein in blood.
As can be seen from the comparison between example 1 and comparative example 4, the addition of hydrochloric acid during the washing can significantly improve the adsorption rate of the adsorbent and reduce the non-specific adsorption (adsorption rate of HDL) thereof, and it is likely that the reagent or reaction by-product of the previous reaction cannot be washed cleanly with methanol or ethanol alone and purified water, which results in affecting the subsequent reaction, and the addition of 0.1 to 0.5mol/L hydrochloric acid for washing can avoid such an effect.
In summary, the invention sequentially adopts propylene oxide and epichlorohydrin to realize the epoxidation modification of the polystyrene adsorption resin, and then the polyanion ligand is coupled. In this way, the obtained low-density lipoprotein adsorbent has good compatibility with blood, has high adsorption rate on low-density lipoprotein in blood, and has weak adsorption on other non-low-density lipoprotein substances, so that the low-density lipoprotein adsorbent has good effect of removing the low-density lipoprotein in the blood. By adding specific catalysts in the hydroxylation reaction and the coupling reaction of the polystyrene resin and adding a hydrochloric acid cleaning step in the cleaning process, the reaction efficiency is improved, and the adsorption efficiency of the prepared adsorbent is improved.
The above embodiments are only for illustrating the technical solution of the present invention and not for limiting the same, and although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications and equivalents may be made thereto without departing from the spirit and scope of the technical solution of the present invention.
Claims (2)
1. The efficient preparation method of the low-density lipoprotein adsorbent is characterized by comprising the following steps of:
s1, adding a swelling agent into polystyrene adsorption resin to fully swell; the swelling agent is dichloroethane;
s2, adding a catalyst A and an epoxy reagent into the swelled polystyrene adsorption resin to carry out ring-opening reaction to obtain a hydroxylated polystyrene adsorption resin; the catalyst A is tetrabutylammonium bromide or ferrous bromide, and the epoxy reagent is propylene oxide; the molar ratio of the polystyrene adsorption resin to the catalyst A to the epoxy agent is 1 (0.2-1) (2-10);
s3, performing ring-opening grafting reaction on the hydroxylated polystyrene adsorption resin and epoxy chloropropane, then performing ring-opening reaction, and cleaning to obtain the epoxidized polystyrene adsorption resin; the catalyst of the ring-opening grafting reaction is boron trifluoride diethyl ether, and the catalyst of the ring-closing reaction is sodium hydroxide; in the step S3, methanol or ethanol, 0.1-0.5 mol/L hydrochloric acid and purified water are used for cleaning in sequence to obtain the epoxidized polystyrene adsorption resin;
s4, mixing the epoxidized polystyrene adsorption resin with a polyanion ligand solution, adding a catalyst B, performing a coupling reaction, and cleaning to obtain a low-density lipoprotein adsorbent; the catalyst B is one of magnesium chloride, aluminum chloride and ferric bromide; the molar ratio of the epoxidized polystyrene adsorption resin to the catalyst B is 1 (0.02-0.5); the mass volume ratio of the epoxidized polystyrene adsorption resin to the polyanion ligand solution is 1g (1-4) mL; the concentration of the polyanion ligand solution is 100-300 mg/mL; the polyanion ligand is one or more of dextran sulfate, heparin or heparin derivatives.
2. A low-density lipoprotein adsorbent prepared by the method of claim 1.
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| 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 |
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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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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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| GR01 | Patent grant | ||
| GR01 | Patent grant |