CN102114416B - Method for preparing protein molecularly imprinted polymer particles - Google Patents
Method for preparing protein molecularly imprinted polymer particles Download PDFInfo
- Publication number
- CN102114416B CN102114416B CN 200910248928 CN200910248928A CN102114416B CN 102114416 B CN102114416 B CN 102114416B CN 200910248928 CN200910248928 CN 200910248928 CN 200910248928 A CN200910248928 A CN 200910248928A CN 102114416 B CN102114416 B CN 102114416B
- Authority
- CN
- China
- Prior art keywords
- protein
- solution
- preparation
- silica gel
- concentration
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 108090000623 proteins and genes Proteins 0.000 title claims abstract description 50
- 102000004169 proteins and genes Human genes 0.000 title claims abstract description 50
- 239000002245 particle Substances 0.000 title abstract description 16
- 238000000034 method Methods 0.000 title abstract description 12
- 229920000344 molecularly imprinted polymer Polymers 0.000 title abstract description 8
- 229920000642 polymer Polymers 0.000 claims abstract description 31
- 239000000243 solution Substances 0.000 claims abstract description 29
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- 238000002360 preparation method Methods 0.000 claims abstract description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000000741 silica gel Substances 0.000 claims abstract description 15
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 15
- 238000001179 sorption measurement Methods 0.000 claims abstract description 11
- 239000012460 protein solution Substances 0.000 claims abstract description 7
- 229920000620 organic polymer Polymers 0.000 claims abstract description 3
- 230000002776 aggregation Effects 0.000 claims abstract 3
- 239000011324 bead Substances 0.000 claims description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 11
- 239000008363 phosphate buffer Substances 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 claims description 7
- 239000011259 mixed solution Substances 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000003431 cross linking reagent Substances 0.000 claims description 4
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 3
- 239000012153 distilled water Substances 0.000 claims description 3
- 239000011159 matrix material Substances 0.000 claims description 3
- 238000004321 preservation Methods 0.000 claims description 3
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 2
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 2
- 239000004088 foaming agent Substances 0.000 claims description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 2
- NXGWSWBWEQYMND-UHFFFAOYSA-N piperazine;prop-2-enamide Chemical compound NC(=O)C=C.NC(=O)C=C.C1CNCCN1 NXGWSWBWEQYMND-UHFFFAOYSA-N 0.000 claims description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims 2
- 229920001213 Polysorbate 20 Polymers 0.000 claims 1
- 238000004220 aggregation Methods 0.000 claims 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims 1
- 238000011095 buffer preparation Methods 0.000 claims 1
- 238000005260 corrosion Methods 0.000 claims 1
- 230000007797 corrosion Effects 0.000 claims 1
- 239000002270 dispersing agent Substances 0.000 claims 1
- 125000005395 methacrylic acid group Chemical group 0.000 claims 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 claims 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 claims 1
- 235000021075 protein intake Nutrition 0.000 claims 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 7
- 229910052710 silicon Inorganic materials 0.000 abstract description 7
- 239000010703 silicon Substances 0.000 abstract description 7
- 238000003795 desorption Methods 0.000 abstract description 3
- 238000005516 engineering process Methods 0.000 abstract description 3
- 238000005054 agglomeration Methods 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- 238000001914 filtration Methods 0.000 abstract 1
- 230000010355 oscillation Effects 0.000 abstract 1
- 238000005086 pumping Methods 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000004925 denaturation Methods 0.000 description 3
- 230000036425 denaturation Effects 0.000 description 3
- 235000003642 hunger Nutrition 0.000 description 3
- 230000037351 starvation Effects 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 102000008192 Lactoglobulins Human genes 0.000 description 2
- 108010060630 Lactoglobulins Proteins 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 108010066476 ribonuclease B Proteins 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000009870 specific binding Effects 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000001262 western blot Methods 0.000 description 2
- 101000955144 Drosophila melanogaster WASH complex subunit 1 Proteins 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- KVBCYCWRDBDGBG-UHFFFAOYSA-N azane;dihydrofluoride Chemical compound [NH4+].F.[F-] KVBCYCWRDBDGBG-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000006249 magnetic particle Substances 0.000 description 1
- 238000012703 microemulsion polymerization Methods 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000010410 reperfusion Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 238000002336 sorption--desorption measurement Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Images
Landscapes
- Peptides Or Proteins (AREA)
Abstract
The invention relates to preparation of protein molecularly imprinted polymer particles, in particular relates to a particulate organic polymer synthesized by a protein molecularly imprinted technology. The protein molecularly imprinted polymer particles are prepared through the following steps: preparing a reacting solution; adsorbing a protein solution in the ducts of porous silica gel by oscillation or filtration and other methods; pumping the reacting solution into the ducts of the silica gel through a vacuum pump or other methods; performing a polymerization or agglomeration reaction in the ducts of the silica gel; and corroding silicon spheres after the polymerization or agglomeration reaction is completed so as to obtain the protein molecularly imprinted polymer particles. The invention has the advantages that the preparation method is simple and convenient, and the polymer particles have regular particle diameters and large adsorption capacity to template protein. Compared with other molecularly imprinted polymer particle preparation methods, the method provided by the invention has few preparation steps, and the prepared polymer particles have the characteristics of high adsorption and desorption speed on the template protein as well as good specificity identification to the template protein.
Description
Technical field
The present invention relates to the preparation of protein molecule engram polymer beads, specifically prepare a kind of granular molecularly imprinted polymer, realize specific identification and combination to the template albumen in the solution.
Background technology
At nature, a lot of life processes all relate to molecular recognition, touch reaction etc. such as immune response, ligand-receptor effect and enzyme.Therefore, molecular recognition plays a part important and special in the life evolution process.Molecular imprinting (MIT) then is the manual simulation to this process.Contain the molecularly imprinted polymer (MIP) in manual identified site by preparation, realize the high selectivity identification to a certain specific target molecule.Because the final goal of MIT is realize artificial antibody's molecule synthetic, therefore relates to numerous subjects such as polymer chemistry, material science, biochemistry, host-guest chemistry and supramolecular chemistry, is to have challenging research field.Traditional molecular engram material is prepared into first integral material mostly, sieves by grinding again, obtains particle diameter large (5-100 μ m) and particle in irregular shape.Therefore not only as chromatograph packing material the time post effect lower, and for large molecule, during such as Western blotting, sorption and desorption speed is all very slow.For addressing the above problem, the polymer beads engram technology has obtained people's concern in recent years, the imprinted polymer particle of regular shape, and the mass transfer velocity of energy Effective Raise sample, and can be used as SPE and chromatograph packing material.Recently, the employing microemulsion polymerization methods such as Tong have synthesized the protein molecule engram magnetic-particle, have larger adsorption capacity (Tan, C.J.; Tong, Y.W.Anal.Chem.2007,79,299-306), but preparation process is loaded down with trivial details, and prepared imprinted polymer is selectively relatively poor.Bossi etc. are take the silicon ball as matrix, having prepared HAS is the trace particle of template albumen, the sorption and desorption speed, but need first template albumen covalency to be fixed on silicon ball surface, remove with oxalic acid again after forming imprinted sites, complex steps, and the trace silicon ball adsorption capacity of preparation is lower, selectively also undesirable.(Bonini,F.;Piletsky,S.;Turner,A.P.F.;Speghini,A.;Bossi,A.Biosens.Bioelectron.2007,22,2322-2328)。
Summary of the invention
The object of the present invention is to provide a kind of preparation method of protein-imprinted polymer particle, in the hope of solving template protein wash-out difficulty when preparing protein-imprinted polymer, resulting imprinted material adsorption-desorption speed is slow, and adsorption capacity is little, the shortcoming of poor selectivity.
For achieving the above object, the technical solution used in the present invention is:
Take the organic polymer reaction solution as example: use Methacrylamide, methacrylic acid is function monomer, and the piperazine bisacrylamide is crosslinking agent, and ammonium sulfate and polysorbas20 are auxiliary reagent, and phosphate buffer is that solvent is mixed with reaction solution.Protein solution is adsorbed in the duct of Bio-sil by methods such as vibration or suction filtrations.After in reaction solution, adding initator, in the duct of vavuum pump with reaction solution suction silica gel.Starvation room temperature reaction 24 hours, erode the silicon ball after, obtain the protein molecule engram polymer beads.
Be specially:
1). elute for fear of protein denaturation with the albumen that adsorbs in the silica gel duct, the proposal reactions system is water, and reacting solution pH value is 4-11 (isoelectric point according to protein is determined);
Contained organic solution can not make protein denaturation, volumetric concentration 0-20%; Such as acetonitrile, dimethyl sulfoxide (DMSO); The inorganic salt concentration 0.01-1M of pore-foaming agent.Because kinds of protein is numerous, character is complicated, can be adjusted according to actual conditions.If reaction system is nonaqueous phase, selection principle does not elute the protein that is adsorbed on first Silica Surface again for must guarantee that the reactant liquor solvent can not make protein denaturation simultaneously.The reaction solution viscosity is decided on pore size and reperfusion mode, must guarantee that reaction solution can enter in the silica gel duct.
The pH value of used phosphate buffer is 5-6.5 in this example.The final weight concentration of each component of adding in the phosphate buffer is: template albumen 0.2~1.6%, function monomer 3.0~6.0%, crosslinking agent 5.0~12.0%, auxiliary reagent 2.0~5.0%, the ratio of phosphate buffer and acetonitrile volume is 1: 4~1: 6.
2). can be take the Bio-sil particle of different-grain diameter as matrix, in order to be conducive to protein and reaction solution transporting in the duct, advise channel diameter minimum be 5 times of protein molecule diameters, be preferably protein molecule diameter more than 10 times.The template protein solution is adsorbed in the duct of Bio-sil by methods such as vibration or suction filtrations, the mass ratio of protein and silica gel is 1: 10~1: 20, in reaction solution, add initator, weight concentration is 0.08~0.2%, reaction solution is pumped in the duct of silica gel starvation reaction 24 hours by vavuum pump.Polymerisation finishes post-etching and falls the silicon ball, obtains the protein molecule engram polymer beads.
3). the protein molecule engram polymer beads for preparing washed 24 hours with containing 10% dodecyl sodium sulfate (mass/volume concentration) and the acetic acid mixed solution of 10% (volumetric concentration), repeatedly wash with distilled water at last, until efflux pH value is about 7.Dry preservation under the room temperature.
Advantage of the present invention is: (1) this method preparation method is easy, and step is few; (2) the polymer beads particle diameter of preparation rule; (3) the Western blotting block polymer of preparation has faster mass transfer rate, higher adsorption capacity and better molecular recognition characteristic; (4) the protein molecule engram particulate polymers for preparing can be used as sorbing material and joins in the solution, perhaps comes template albumen in the specific binding solution as the filler of solid-phase extraction column.
Description of drawings
Fig. 1 is the scanning electron microscope (SEM) photograph (* 20000) of the protein molecule engram polymer beads of preparation
Fig. 2 is the HPLC chromatogram of four protein mixed solutions, from left to right is respectively ribonuclease B, cromoci, the chromatographic peak of PSA and beta lactoglobulin.
Fig. 3 is the chromatogram after the mixed solution of four albumen passes through protein molecule engram polymer beads adsorption treatment.Can see that the template albumen (PSA) in the solution is removed by specificity after processing, and very little to the absorption of other protein.This shows that the protein molecule engram polymer beads has preferably selective recognition capability to template molecule.
The specific embodiment
Prepare in accordance with the following steps a kind of protein-imprinted polymer particle.
Embodiment 1
The final weight concentration of each component of adding in the phosphate buffer is: template albumen 0.2~1.6%, function monomer 3.0~6.0%, crosslinking agent 5.0~12.0%, auxiliary reagent 2.0~5.0%, the ratio of phosphate buffer and acetonitrile volume is 1: 4~1: 6.The pH value of phosphate buffer is the interior adjusting of the scope of template albumen isoelectric point ± 2.
The template protein solution is adsorbed in the duct of Bio-sil by methods such as vibration or suction filtrations, the mass ratio of protein and silica gel is 1: 8-1: 20, in reaction solution, add initator and rate accelerating material, weight concentration is 0.08~0.2%, reaction solution is pumped in the duct of silica gel by vavuum pump, starvation reaction 24 hours, heat cause the control temperature below 60 ℃.Polymerisation is used hydrogen fluoride after finishing, and ammonium acid fluoride or sodium hydroxide solution erode the silicon ball, obtain the protein molecule engram polymer beads.
The protein molecule engram polymer beads for preparing washed 24 hours with containing 10% dodecyl sodium sulfate (mass/volume concentration) and the acetic acid mixed solution of 10% (volumetric concentration), repeatedly wash with distilled water at last, until efflux pH value is about 7.Dry preservation under the room temperature.
Template albumen is PSA (PSA).
The synthesis condition of polymer beads is as shown in the table:
Application examples
The protein molecule engram particulate polymers for preparing can be used as sorbing material and joins in the solution, perhaps comes template albumen in the specific binding solution as the filler of solid-phase extraction column.
Fig. 2 is the HPLC chromatogram of four protein mixed solutions, from left to right is respectively ribonuclease B, cromoci, the chromatographic peak of PSA and beta lactoglobulin.
Fig. 3 is the chromatogram after the mixed solution of four albumen passes through protein molecule engram polymer beads adsorption treatment.Can see that the template albumen (PSA) in the solution is removed by specificity after processing, and very little to the absorption of other protein.This shows that the protein molecule engram polymer beads has preferably selective recognition capability to template molecule.
Claims (3)
1. the preparation method of a protein molecule engram polymer beads is characterized in that:
First with protein adsorption in the hole of Bio-sil, then pour into reaction solution, and react, carry out at last the corrosion of silica gel, obtain the protein molecule engram polymer beads;
Described reaction solution is organic polymer soln, and reaction system is water, and reacting solution pH value is 4-11;
The reaction that reaction solution occurs in the silica gel duct is polymerisation or aggregation; Reaction result is to be full of continuous integral material in the silica gel duct;
The Bio-sil that the polymer beads of preparation different-grain diameter is selected different-grain diameter and aperture is as matrix, and the duct of Bio-sil is interconnected; Silica gel channel diameter 〉=5 times protein molecule diameter;
Described protein is the protein solution that any or multiple protein is made into, and protein solution concentration 0.1-5mg/mL, the mass ratio of protein and silica gel are 1: 8-1: 20;
Described protein solution is the phosphate buffer of protein, and the pH value is 4-11, and the protein final weight concentration of adding in the phosphate buffer is 0.2~1.6%;
Described reaction solution adopts the phosphate buffer preparation, and the final weight concentration of each component is: function monomer concentration is 3.0~6.0%, and crosslinking agent piperazine bisacrylamide concentration is 5.0~12.0%,
Function monomer is methacrylic acid and Methacrylamide, and their mass ratio is 1: 15-21; Initator is that the ammonium persulfate weight concentration is 0.01-0.04%, and rate accelerating material is N, N, and N`, N`-tetramethylethylenediamine weight concentration is 0.05-0.2%; Dispersant Tween-20 or acetonitrile weight concentration are 0-20%; The pore-foaming agent ammonium sulfate concentrations is 0.01-1M;
The mol ratio of function monomer and protein consumption is 2000-4000: 1.
2. according to preparation method claimed in claim 1, it is characterized in that: reaction temperature 23-27 ℃, time 14-24 hour.
3. according to preparation method claimed in claim 1, it is characterized in that:
The protein molecule engram polymer beads for preparing washed 24 hours with the acetic acid mixed solution of the dodecyl sodium sulfate that contains mass/volume concentration 10% and volumetric concentration 10%, repeatedly wash with distilled water at last, until efflux pH value is 7, dry preservation under the room temperature;
The protein molecule engram polymer beads for preparing has the ability of with template protein-specific being combined similar with antibody.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 200910248928 CN102114416B (en) | 2009-12-30 | 2009-12-30 | Method for preparing protein molecularly imprinted polymer particles |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 200910248928 CN102114416B (en) | 2009-12-30 | 2009-12-30 | Method for preparing protein molecularly imprinted polymer particles |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102114416A CN102114416A (en) | 2011-07-06 |
CN102114416B true CN102114416B (en) | 2013-01-30 |
Family
ID=44213403
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 200910248928 Expired - Fee Related CN102114416B (en) | 2009-12-30 | 2009-12-30 | Method for preparing protein molecularly imprinted polymer particles |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN102114416B (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103585979B (en) * | 2013-09-26 | 2016-08-17 | 湖南中烟工业有限责任公司 | A kind of cigarette filter rod polymeric sorbent and its preparation method and application |
CN104403043B (en) * | 2014-12-12 | 2016-06-22 | 南开大学 | The molecular engram microsphere of discrete group albumen H4-K16 acetylation labeling polypeptide |
CN108079957B (en) * | 2016-11-21 | 2020-08-11 | 中国科学院大连化学物理研究所 | N-phosphorylated peptide fragment and protein enrichment material, and preparation and application thereof |
CN111068624B (en) * | 2019-12-27 | 2023-07-21 | 西北工业大学 | Preparation method of molecular imprinting mesoporous material with enlarged aperture |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101463105A (en) * | 2007-12-21 | 2009-06-24 | 中国科学院大连化学物理研究所 | Protein imprinted material and use thereof for removing albumin from human blood serum |
-
2009
- 2009-12-30 CN CN 200910248928 patent/CN102114416B/en not_active Expired - Fee Related
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101463105A (en) * | 2007-12-21 | 2009-06-24 | 中国科学院大连化学物理研究所 | Protein imprinted material and use thereof for removing albumin from human blood serum |
Non-Patent Citations (2)
Title |
---|
M.E. Brown et al..Protein binding to peptide-imprinted porous silica scaffolds.《Chemical Engineering Journal》.2008,第137卷参见第98页第2节. * |
刘秋叶等.硅胶修饰-表面分子印迹牛血红蛋白及其识别性能的研究.《化学学报》.2008,第66卷(第1期),第57页第1.2节. * |
Also Published As
Publication number | Publication date |
---|---|
CN102114416A (en) | 2011-07-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Masini et al. | Porous monoliths for on-line sample preparation: a review | |
Chen et al. | Synthesis of surface molecularly imprinted nanoparticles for recognition of lysozyme using a metal coordination monomer | |
JP5021320B2 (en) | Flow-through porous monolith combined with ion exchange particles | |
Wu et al. | Recent advances in green reagents for molecularly imprinted polymers | |
CN103408785B (en) | Preparation method of cerium ion surface imprinted polymer based on silicon-based mesoporous molecular sieve | |
Liang et al. | Ordered macroporous molecularly imprinted polymers prepared by a surface imprinting method and their applications to the direct extraction of flavonoids from Gingko leaves | |
Li et al. | Fabrication of surface protein-imprinted nanoparticles using a metal chelating monomer via aqueous precipitation polymerization | |
CN102114416B (en) | Method for preparing protein molecularly imprinted polymer particles | |
CN101463105B (en) | Protein imprinted material and use thereof for removing albumin from human blood serum | |
CN108079974B (en) | Preparation method of protein print macromolecular adsorbent and adsorption device | |
Baran et al. | Efficient adsorption of hemoglobin from aqueous solutions by hybrid monolithic cryogel column | |
CN106883411B (en) | Preparation of superparamagnetic core-shell structure mesoporous molecularly imprinted polymer and application of superparamagnetic core-shell structure mesoporous molecularly imprinted polymer as solid phase extractant | |
CN107955171A (en) | A kind of preparation method and adsorbent equipment of protein binding toxin imprinted silica gel adsorbent | |
Sun et al. | A restricted access molecularly imprinted polymer coating on metal–organic frameworks for solid-phase extraction of ofloxacin and enrofloxacin from bovine serum | |
Dmitrienko et al. | Use of molecular imprinted polymers for the separation and preconcentration of organic compounds | |
Song et al. | Thermo-responsive adsorption and separation of amino acid enantiomers using smart polymer-brush-modified magnetic nanoparticles | |
Ding et al. | Preparation and characterization of biocompatible molecularly imprinted poly (ionic liquid) films on the surface of multi-walled carbon nanotubes | |
Jian et al. | Research progress of the molecularly imprinted cryogel | |
Ergün et al. | Ion imprinted beads embedded cryogels for in vitro removal of iron from β‐thalassemic human plasma | |
Qiao et al. | High-surface-area interconnected macroporous nanofibrous cellulose microspheres: a versatile platform for large capacity and high-throughput protein separation | |
Ektirici et al. | Selective recognition of nucleosides by boronate affinity organic-inorganic hybrid monolithic column | |
Han et al. | An ionic liquid–molecularly imprinted composite based on graphene oxide for the specific recognition and extraction of cancer antigen 153 | |
Zhang et al. | Synergistic effect of polyhedral oligomeric semisiloxane and boronate affinity molecularly imprinted polymer in a solid-phase extraction system for selective enrichment of ovalbumin | |
Bo et al. | Grafting copolymer brushes on polyhedral oligomeric silsesquioxanes silsesquioxane-decorated silica stationary phase for hydrophilic interaction liquid chromatography | |
Erzengin et al. | Monolithic hydrophobic cryogel columns for protein separation |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20130130 |