CN112941655B - Nano-fiber bilirubin adsorbent and preparation method thereof - Google Patents
Nano-fiber bilirubin adsorbent and preparation method thereof Download PDFInfo
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- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
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- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
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- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/16—Synthetic fibres, other than mineral fibres
- D06M2101/18—Synthetic fibres consisting of macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M2101/26—Polymers or copolymers of unsaturated carboxylic acids or derivatives thereof
- D06M2101/28—Acrylonitrile; Methacrylonitrile
Abstract
The invention belongs to the field of biomedical materials, and particularly relates to a nanofiber bilirubin adsorbent and a preparation method thereof, wherein the nanofiber bilirubin adsorbent is obtained through steps of electrostatic spinning, a pore-forming process, grafting modification and the like, and the prepared nanofiber adsorbent can specifically identify bilirubin molecules by utilizing multiple action sites such as electrostatic adsorption, hydrogen bonds, pi-pi action and the like, so that the adsorption quantity and selectivity of the adsorbent are improved; the mesoporous channel communicated with the fiber can increase the utilization rate of the adsorption sites and accelerate the adsorption rate. The nanofiber adsorbent can rapidly and selectively remove bilirubin with high capacity, and the bilirubin removal rate can reach 96.8%. In addition, the nanofiber adsorbent provided by the invention has the advantages of high stability, good compatibility, simple and feasible preparation process, easiness in realization of industrial production, and wide application prospect in the field of preparation of medicines for removing excessive bilirubin in blood.
Description
Technical Field
The invention belongs to the field of biomedical materials, and particularly relates to a nanofiber bilirubin adsorbent and a preparation method thereof.
Background
Bilirubin is the main product of hemoglobin metabolism, but patients with severe hepatitis cannot eliminate bilirubin in time, resulting in excessive accumulation of bilirubin in the blood, known as hyperbilirubinemia. The surplus bilirubin can cause skin yellowing and also can cause a series of injuries to tissues and organs, and even death. Blood perfusion is an important method for treating severe hepatitis and hyperbilirubinemia, and the adsorbent is a key factor for determining perfusion effect. At present, the traditional perfusion adsorbents which are applied to clinic comprise coated active carbon, macroporous adsorption resin, carbonized resin and the like. However, the binding capacity of activated carbon is weak, and the specific surface area of the adsorbent resin is low, so that the therapeutic effect of the adsorbent resin is not ideal. The development of a high-performance bilirubin perfusion adsorbent (searching for an ideal substitute of a traditional adsorbent) is a bottleneck which is urgently needed in clinic and needs to be broken through, and has important significance for improving the quality and efficiency of medical care.
The micro-nano fiber obtained by the electrostatic spinning technology has the advantages of high porosity, simple and controllable preparation, easy modification and the like, so that the micro-nano fiber has great application potential in the field of adsorption separation. Compared with the traditional spherical particle bilirubin adsorbent, the high porosity of the fiber adsorbent can ensure that bilirubin molecules are fully contacted with action sites; when the adsorption column is used as the adsorption column, the stacking among fibers is tighter than the stacking among spherical particles, so that the interception effect is improved; the above is the structural advantage of the electrospun fiber as the bilirubin adsorbent. However, the traditional polymer electrospun fiber does not have an effective bilirubin binding site, and in order to improve the adsorption capacity and selectivity of the electrospun fiber for bilirubin, an adsorption group with specific recognition to bilirubin is necessary to be grafted on the fiber. Besides, besides the gaps formed by stacking among the fibers, the construction of the through and communicated mesoporous channels on the fibers can further improve the utilization rate of adsorption sites, increase the mass transfer rate of bilirubin molecules, and have positive effects on improving the adsorption capacity and accelerating the adsorption speed. Therefore, how to obtain the bilirubin adsorbent clinically required by reasonably designing and effectively regulating and controlling the combination of the electrospun fibers and the pore structure is a technical problem to be solved urgently at present.
Disclosure of Invention
In order to solve the technical problem, the invention provides a nanofiber bilirubin adsorbent, and a preparation method thereof comprises the following steps:
(1) dissolving polyacrylonitrile, a pore-forming agent and a pore propping agent in an organic solvent to obtain a mixed solution, wherein the mass fraction of the polyacrylonitrile is 4-20 wt%, the mass fraction of the pore-forming agent is 6-40 wt% and the mass fraction of the pore propping agent is 2-30 wt%, stirring the mixed solution until the mixed solution is clear, and then performing electrostatic spinning to obtain the blended nanofiber;
(2) placing the blended nanofiber obtained in the step (1) in an eluent to remove a pore-forming agent from the fiber, wherein the elution temperature is 20-80 ℃, the elution time is 2-48 h, and drying the eluted blended nanofiber to obtain the nanofiber with a through and communicated mesoporous channel;
(3) placing the nanofiber with the through and communicated mesoporous channel obtained in the step (2) in a polyamine compound solution, refluxing at 80-200 ℃ or carrying out solvothermal reaction for 1-24 h, washing and drying to obtain amine-functionalized nanofiber; placing the amine functionalized nanofiber in a halogenated compound solution, carrying out reflux or solvothermal reaction for 2-48 h at 40-200 ℃, washing and drying to obtain the nanofiber bilirubin adsorbent with multiple action sites and communicated with mesoporous channels in a penetrating manner.
Further, the organic solvent in the step (1) is N, N-dimethylformamide or dimethyl sulfoxide.
Further, the pore-forming agent in the step (1) is one of polyethylene oxide, polyvinylpyrrolidone, polyacrylic acid, polyacrylamide or polyvinyl alcohol; the pore channel propping agent is one or any combination of activated carbon powder, boehmite, graphene oxide, a metal-organic framework material, a porous aromatic framework material, a covalent organic framework material, a carbon nano tube, ferroferric oxide nano particles or a molecular sieve.
Further, the eluent in the step (2) is one or any combination of water or ethanol.
Further, the polyamine compound in the step (3) is diethylenetriamine, N-diethylethylenediamine, N-dimethylaminoethylenediamine, N-dimethyl-1, 3-propanediamine, N-ethylethylenediamine, triethylenetetramine, tetraethylenepentamine, N-diisopropylethylenediamine, N- (2-aminoethyl) piperazine, 1- (2-aminoethyl) -4-methylpiperazine, N' -bis (2 aminoethyl) -piperazine, N- (2-aminoethyl) pyrrolidine, 1, 4-bis (3-aminopropyl) piperazine, N-methylethylenediamine, N-di-N-propylethylenediamine, N-N-propylethylenediamine, tris (2-aminoethyl) amine or polyethyleneimine, or any combination thereof; the halogenated compound in the step (3) is one or any combination of benzyl bromide, 4-methylbenzyl bromide, 2- (bromomethyl) naphthalene, 1,3, 5-tri (bromomethyl) benzene, 1-bromo-2-methylpropane, 1-bromoalkane (with the carbon number of 2-18), 1-bromo-4-methylpentane, 5-bromo-1-pentene, 1-chloroalkane (with the carbon number of 2-18), chloroisobutane or benzyl chloride.
Further, the solvent in the solvent thermal reaction in the step (3) is one or any combination of water, ethanol, ethylene glycol, acetonitrile, nitrobenzene or tetrahydrofuran.
Further, the mass fraction of the polyamine in the polyamine compound solution in the step (3) is 2-80 wt%; the mass fraction of the halogenated compound in the halogenated compound solution is 1-50 wt%.
The invention also provides application of the nanofiber bilirubin adsorbent in preparation of a medicine for removing excessive bilirubin in blood.
Has the advantages that:
the invention constructs a channel with multiple action sites (electrostatic adsorption, hydrogen bonds, pi-pi action and the like) and through and communicated mesopores on the electro-spinning polyacrylonitrile fiber by simulating the combination mode (electrostatic interaction, van der Waals force) of bilirubin and human serum albumin in human blood and hopefully utilizing the porous property of the channel through pore-forming by a template agent and graft modification (detailed in figure 1). The nanofiber has multiple action sites such as electrostatic action, hydrophobic action, hydrogen bonds and the like, and can enhance the binding energy of the nanofiber adsorbent to bilirubin and improve the adsorption capacity and selectivity; the nanofiber is also provided with a through and communicated mesoporous channel, so that more adsorption sites can be exposed, and the mass transfer rate of bilirubin molecules on the fiber can be accelerated.
The adsorbent has simple preparation process and low cost of raw materials, part of the raw materials can be recycled, and the industrial production is easy to realize; because the base material polyacrylonitrile is non-toxic, the obtained adsorbent has good blood compatibility and biocompatibility. The multiple action sites of the fiber adsorbent disclosed by the invention can selectively and specifically identify bilirubin molecules; the mesoporous channels are communicated in a penetrating way, so that the grafting density of functional groups can be increased, the utilization rate of action sites can be improved, and the mass transfer rate of bilirubin molecules can be accelerated; when the fibrous adsorbent is used as an adsorption column, the fiber can be well packed and formed, and the space is saved compared with the space of a granular adsorbent; therefore, the nanofiber bilirubin adsorbent provided by the invention has multiple action sites and runs through and communicates with the mesoporous channel, can be used for rapidly and selectively removing excessive bilirubin in blood in a large capacity, and has good application prospects in clinic.
The pore size of the nanofiber bilirubin adsorbent obtained by the method is 5 nm-300 nm.
Drawings
FIG. 1: the invention is a flow diagram for preparing a nanofiber bilirubin adsorbent which has multiple action sites and penetrates and is communicated with a mesoporous channel;
FIG. 2 is a schematic diagram: example 2 SEM image of nanofiber bilirubin adsorbent with multiple action sites and through-connected mesoporous channels obtained in step (3).
Detailed Description
The present invention is further described below by way of examples, but the embodiments of the present invention are not limited thereto, and should not be construed as limiting the scope of the invention.
Example 1:
(1) dissolving polyacrylonitrile, a metal-organic framework material and a polyvinylpyrrolidone agent in N, N-dimethylformamide to obtain a mixed solution, wherein the mass fraction of the polyacrylonitrile in the mixed solution is 4 wt%, the mass fraction of the polyvinylpyrrolidone in the mixed solution is 6 wt%, and the mass fraction of the metal-organic framework material in the mixed solution is 10 wt%, stirring the mixed solution until the mixed solution is clear, and then carrying out electrostatic spinning to obtain the blended nanofiber;
(2) placing the blended nanofiber obtained in the step (1) in ethanol to remove polyvinylpyrrolidone from the fiber, wherein the elution temperature is 80 ℃, the elution time is 2 hours, and the eluted blended nanofiber is dried to obtain the nanofiber with a through and communicated mesoporous channel;
(3) placing the nanofiber with the through and communicated mesoporous channel obtained in the step (2) in 80 wt% of triethylene tetramine aqueous solution for reflux reaction at 100 ℃ for 24 hours to obtain functionalized nanofiber; placing the amine functionalized nano-fiber in 50 wt% of 1-bromooctane ethanol solution, performing reflux reaction at 40 ℃ for 48 hours, washing and drying to obtain the nano-fiber bilirubin adsorbent with multiple action sites and communicated with a mesoporous channel.
Example 2:
(1) dissolving polyacrylonitrile, carbon nano tubes and polyacrylic acid in N, N-dimethylformamide to obtain a mixed solution, wherein the mass fraction of the polyacrylonitrile in the mixed solution is 20 wt%, the mass fraction of the polyacrylic acid is 25 wt%, and the mass fraction of the carbon nano tubes is 6 wt%, stirring the mixed solution until the mixed solution is clear, and then carrying out electrostatic spinning to obtain the blended nano fibers;
(2) placing the blended nanofiber obtained in the step (1) in water to remove polyacrylic acid from the fiber, wherein the elution temperature is 120 ℃, the elution time is 48 hours, and the eluted blended nanofiber is dried to obtain the nanofiber with through-communicated mesoporous channels;
(3) placing the nanofiber with the through and communicated mesoporous channel obtained in the step (2) in an N-N-propyl ethylenediamine aqueous solution with the mass fraction of 2 wt% for reflux reaction at 160 ℃ for 6 hours to obtain amine functionalized nanofiber; placing the amine-functionalized nano-fiber in 20 wt% of benzyl chloroacetonitrile solution, carrying out reflux reaction at 100 ℃ for 3h, washing and drying to obtain the nano-fiber bilirubin adsorbent with multiple action sites and communicated mesoporous channels (see figure 2 for details).
Example 3:
(1) dissolving polyacrylonitrile, boehmite and polyvinyl alcohol in dimethyl sulfoxide to obtain a mixed solution, wherein the mass fraction of polyacrylonitrile in the mixed solution is 10 wt%, the mass fraction of polyvinyl alcohol is 40 wt%, and the mass fraction of carbon nano tubes is 10 wt%, stirring the mixed solution to be clear, and then performing electrostatic spinning to obtain the blended nano-fiber;
(2) placing the blended nanofiber obtained in the step (1) in water to remove polyvinyl alcohol from the fiber, wherein the elution temperature is 20 ℃, the elution time is 24 hours, and drying the eluted blended nanofiber to obtain the nanofiber with through and communicated mesoporous channels;
(3) placing the nanofiber with the through and communicated mesoporous channel obtained in the step (2) in 80 wt% of polyethyleneimine water solution to perform hydrothermal reaction for 1h at 120 ℃ to obtain amine-functionalized nanofiber; and then placing the amine functionalized nano-fiber in a nitrobenzene solution of 1-bromo-2-methylpropane with the mass fraction of 50 wt% for reflux reaction at 60 ℃ for 12 hours, and then washing and drying to obtain the nano-fiber bilirubin adsorbent with multiple action sites and communicated with the mesoporous channel.
Example 4:
(1) dissolving polyacrylonitrile, a porous aromatic skeleton material and polyethylene oxide in N, N-dimethylformamide to obtain a mixed solution, wherein the mass fraction of the polyacrylonitrile in the mixed solution is 12 wt%, the mass fraction of the polyethylene oxide in the mixed solution is 40 wt%, and the mass fraction of the porous aromatic skeleton material in the mixed solution is 12 wt%, stirring the mixed solution until the mixed solution is clarified, and performing electrostatic spinning to obtain the blended nanofiber;
(2) placing the blended nanofiber obtained in the step (1) in ethanol to remove polyethylene oxide from the fiber, wherein the elution temperature is 70 ℃, the elution time is 36 hours, and drying the eluted blended nanofiber to obtain the nanofiber with through and communicated mesoporous channels;
(3) placing the nanofiber with the through and communicated mesoporous channel obtained in the step (2) in 40 wt% of N, N-dimethyl-1, 3-propane diamine aqueous solution for reflux reaction at 90 ℃ for 24 hours to obtain amine functionalized nanofiber; placing the amine functionalized nano-fiber in an acetone solution of 45 wt% of 2- (bromomethyl) naphthalene, performing reflux reaction at 50 ℃ for 10 hours, washing and drying to obtain the nano-fiber bilirubin adsorbent with multiple action sites and communicated with a mesoporous channel.
Example 5:
(1) dissolving polyacrylonitrile, ferroferric oxide nanoparticles and a polyvinylpyrrolidone agent in N, N-dimethylformamide to obtain a mixed solution, wherein the mass fraction of polyacrylonitrile in the mixed solution is 15 wt%, the mass fraction of polyvinylpyrrolidone in the mixed solution is 30 wt%, and the mass fraction of ferroferric oxide nanoparticles in the mixed solution is 8 wt%, stirring the mixed solution to be clear, and then carrying out electrostatic spinning to obtain the blended nanofiber;
(2) placing the blended nanofiber obtained in the step (1) in water to remove polyvinylpyrrolidone from the fiber, wherein the elution temperature is 120 ℃, the elution time is 48 hours, and the eluted blended nanofiber is dried to obtain the nanofiber with a through and communicated mesoporous channel;
(3) placing the nanofiber with the through and communicated mesoporous channel obtained in the step (2) in 20 wt% N- (2-aminoethyl) piperazine acetonitrile solution for reflux reaction at 100 ℃ for 13h to obtain amine functionalized nanofiber; placing the amine functionalized nano-fiber in tetrahydrofuran solution of 1-chloropentane with the mass fraction of 20 wt%, performing reflux reaction at 60 ℃ for 24h, washing and drying to obtain the nano-fiber bilirubin adsorbent with multiple action sites and communicated with the mesoporous channel.
The adsorption performance and the hemolysis ratio of the adsorbents obtained in examples 1 to 5 on bilirubin are shown in Table 1 below, and the control group was BL300 one-time-use bilirubin adsorbent resin produced by Asahi Kasei-Coli medical Co.
The pore size of the nanofiber bilirubin adsorbent obtained in the embodiment is 5-300 nm.
Table 1: the adsorption performance of examples 1-5 and the control group to bilirubin and the hemolysis rate of the material.
| Hemolysis ratio (%) | Bilirubin removal rate (%) | |
| Example 1 | 1.1 | 72.4 |
| Example 2 | 1.2 | 75.1 |
| Example 3 | 0.6 | 96.8 |
| Example 4 | 0.3 | 82.9 |
| Example 5 | 1.0 | 69.8 |
| Control group | 0.8 | 73.9 |
Claims (7)
1. A nanofiber bilirubin adsorbent is characterized in that: the preparation method comprises the following steps:
(1) dissolving polyacrylonitrile, a pore-forming agent and a pore propping agent in an organic solvent to obtain a mixed solution, wherein the mass fraction of the polyacrylonitrile is 4-20 wt%, the mass fraction of the pore-forming agent is 6-40 wt% and the mass fraction of the pore propping agent is 2-30 wt%, stirring the mixed solution until the mixed solution is clear, and then performing electrostatic spinning to obtain the blended nanofiber;
(2) placing the blended nanofiber obtained in the step (1) in an eluent to remove a pore-forming agent from the fiber, wherein the elution temperature is 20-80 ℃, the elution time is 2-48 h, and drying the eluted blended nanofiber to obtain the nanofiber with a through and communicated mesoporous channel;
(3) placing the nanofiber with the through and communicated mesoporous channel obtained in the step (2) in a polyamine compound solution, refluxing at 80-200 ℃ or carrying out solvothermal reaction for 1-24 h, washing and drying to obtain amine-functionalized nanofiber; placing the amine functionalized nano-fiber in a halogenated compound solution, refluxing at 40-200 ℃ or carrying out solvothermal reaction for 2-48 h, washing and drying to obtain a nano-fiber bilirubin adsorbent which has multiple action sites and is communicated with a mesoporous channel in a penetrating manner;
the polyamine compound in the step (3) is diethylenetriamine, N-diethylethylenediamine, N-dimethylamino-ethylenediamine, N-dimethyl-1, 3-propanediamine, N-ethylethylenediamine, triethylenetetramine, tetraethylenepentamine, N-diisopropylethylenediamine or N- (2-aminoethyl) piperazine, 1- (2-aminoethyl) -4-methylpiperazine, N' -bis (2-aminoethyl) -piperazine, N- (2-aminoethyl) pyrrolidine, 1, 4-bis (3-aminopropyl) piperazine, N-methylethylenediamine, N-di-N-propylethylenediamine, N-N-propylethylenediamine, tris (2-aminoethyl) amine or polyethyleneimine, or any combination thereof; the halogenated compound in the step (3) is one or any combination of benzyl bromide, 4-methylbenzyl bromide, 2- (bromomethyl) naphthalene, 1,3, 5-tri (bromomethyl) benzene, 1-bromoalkane with the carbon number of 2-18, 5-bromo-1-pentene, 1-chloroalkane with the carbon number of 2-18, chloroisobutane or benzyl chloride.
2. The nanofiber bilirubin adsorbent of claim 1, wherein: the organic solvent in the step (1) is N, N-dimethylformamide or dimethyl sulfoxide.
3. The nanofiber bilirubin adsorbent of claim 1, wherein: the pore-forming agent in the step (1) is one of polyethylene oxide, polyvinylpyrrolidone, polyacrylic acid, polyacrylamide or polyvinyl alcohol; the pore channel propping agent is one or any combination of activated carbon powder, boehmite, graphene oxide, a metal-organic framework material, a covalent organic framework material, a carbon nano tube, ferroferric oxide nano particles or a molecular sieve.
4. The nanofiber bilirubin adsorbent of claim 1, wherein: the eluent in the step (2) is one or any combination of water or ethanol.
5. The nanofiber bilirubin adsorbent of claim 1, wherein: and (3) the solvent in the solvent thermal reaction is one or any combination of water, ethanol, ethylene glycol, acetonitrile, nitrobenzene or tetrahydrofuran.
6. The nanofiber bilirubin adsorbent of claim 1, wherein: the mass fraction of the polyamine in the polyamine compound solution in the step (3) is 2-80 wt%; the mass fraction of the halogenated compound in the halogenated compound solution is 1-50 wt%.
7. Use of a nanofiber bilirubin adsorbent as claimed in any one of claims 1 to 6 in the manufacture of a medicament for the clearance of excess bilirubin in the blood.
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| JPH04322659A (en) * | 1991-04-23 | 1992-11-12 | Sekisui Chem Co Ltd | Bilirubin and adsorbent for bile acid |
| JP4775001B2 (en) * | 2005-03-31 | 2011-09-21 | 東レ株式会社 | Material that removes albumin-unbound and glucuronic acid-unconjugated bilirubin |
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| CN112941655A (en) | 2021-06-11 |
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