CN104356308A - Preparation method of bovine serum albumin molecular surface imprinted polymer microspheres - Google Patents
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Abstract
The invention provides a preparation method of bovine serum albumin molecular surface imprinted polymer microspheres. The method comprises the following steps: 1, adding methacryloyl chloride into an acetone solution containing crosslinked polyvinyl alcohol microspheres to form modified microspheres; 2, combining acryloyloxyethyl trimethyl ammonium chloride with bovine serum albumin molecules in a neutral aqueous solution by virtue of strong electrostatic interactions so as to form a host-guest complex; 3, carrying out a crosslinking copolymerization reaction on the metacrylate modified microspheres, the host-guest complex, a crosslinking agent N,N'-methylene bisacrylamide and an initiating agent so as to achieve the surface imprinting of the bovine serum albumin molecules; and 4, repeatedly flushing the imprinted microspheres with sodium chloride and then flushing the imprinted microspheres with distilled water so as to obtain the bovine serum albumin molecular surface imprinted polymer microspheres with a large quantity of template molecular imprinted cavities retained on the surfaces. According to the method, the protein imprinting is carried out on the basis of the electrostatic interactions between the template protein and each functional monomer; and a new molecular design thought for developing a protein molecular imprinting technology is provided. Thus, the method provided by the invention has a positive reference value in the protein separation and purification field.
Description
Technical field
The invention belongs to protein engineering and functional polymer technical field, relate to a kind of preparation with the molecular surface imprinting polymer microballoon of identification selection biomacromolecule characteristic, specifically a kind of preparation method of bovine serum albumin molecular surface imprinting polymer microballoon.
Background technology
Molecularly imprinted polymer (MIPs) is tailored (Well-tailored) class functional polymer material meticulously, its inside is distributed with the imprinted cavity of a large amount of template molecule, these holes are in size, space structure, the aspects such as binding site and template molecule mate to heavens mutually, make molecularly imprinted polymer can carry out specific recognition to template molecule on a molecular scale, have to be similar between antibody-antigene and identify and the specificity combined, therefore artificial antibody (Artificial antibody) or artificial susceptor (Artificial acceptor) is called by people.In the identification, isolation and purification of protein and other, molecular imprinting also has potential, important application prospect, the development of biomacromolecule molecular imprinting, for promoting that the development of the life science subjects such as proteomics, recombinant protein technology and immunology all has very important scientific meaning.But due to protein macromolecule complex structure, bulky and conformation sensitization is fragile, at present about the trace of protein, no matter in theory or practice remains at many difficulties, significantly limit the development of proteins molecularly imprinted technique selectivity.Therefore, protein molecule engram is one and has challenging research field.
At present in western blotting, obviously there is Railway Project: (1) traditional embedding blotting is not suitable for the trace of protein.In highly cross-linked bulk polymer network, protein macromolecule poor mobility, cause low imprinting efficiency and poor bonding properties, and microsphere not easily wash-out [Kryscio D R, Peppas N A. Critical review and perspective of macromolecularly imprinted polymers, Acta Biomaterialia, 2012,8:461 – 473]; (2) selection of solvent is restricted.In organic solvent, although the interaction of hydrogen bond between template protein molecule and monomer (so far, interaction of hydrogen bond between the main master plate molecule-function monomer of most protein molecule engrams) interference-free, be conducive to printing process, but most protein is all poor [the Bossi A of stability and solvability in organic solvent, Bonini F, Turner A P F, Piletsky S A. Molecularly imprinted polymers for the recognition of proteins:The state of the art, Biosensors and Bioelectronics, 2007, 22:1131 – 1137], if be solvent with water, although protein is water-soluble, the interaction of hydrogen bond between template protein-monomer can suffer competition and the destruction of water molecules, is unfavorable for printing process, (3) monomer is single, little [the Verheyen E of range of choice, Schillemans J P, Wijk M van, Demeniex M-A, Hennink W E, Nostrum C F van. Challenges for the effective molecular imprinting of proteins, Biomaterials, 2011,32:3008 – 3020].As mentioned above, interaction of hydrogen bond is still the predominant intermolecular forces basis of current western blotting, therefore the monomer used is confined to acrylamide and acrylic monomer more, and imprinting effect is affected.
Summary of the invention
The object of this invention is to provide a kind of preparation method of bovine serum albumin molecular surface imprinting polymer microballoon, cationic monomer acrylyl oxy-ethyl-trimethyl salmiac is selected to be function monomer, fully studying on the basis of the strong electrostatic interaction in water medium between host-guest, adopt surface imprinted method, implement the surface imprinted of bovine serum albumin molecule, prepare bovine serum albumin molecular surface engram material.
Albumin is the important carrier albumen that in blood plasma, content is the abundantest, has the important physiological function such as accumulating endogenous metabolites and exogenous drugs molecule, participates in many important vital processes.The iso-electric point of bovine serum albumin is 4.7, and in neutral aqueous solution, albumin is negative ion, and per molecule can with more than 200 negative charges.In view of albuminous above-mentioned physics-chem characteristic, by molecular designing and the planning of science, formulate effective preparation strategy and approach: (1) replaces embedding blotting by surface imprinted method; (2) except interaction of hydrogen bond, plan, based on the electrostatic interaction between template protein-function monomer, in water medium, to implement the trace of protein.
The technical solution adopted in the present invention is: a kind of preparation method of bovine serum albumin molecular surface imprinting polymer microballoon, comprises following step:
Step one, adds in the acetone soln containing cross-linking polyvinyl alcohol microballoon by methacrylic chloride and a small amount of acid binding agent sodium carbonate, and a large amount of polymerizable double bond is introduced microsphere surface, forms the modification microballoon being bonded with a large amount of methacrylate based group;
Step 2, in neutral aqueous solution, forms Host-guest complex with bovine serum albumin in conjunction with mix and blend by acrylyl oxy-ethyl-trimethyl salmiac;
Step 3, the modification microballoon being bonded with a large amount of methacrylate based group is added in Host-guest complex, add N again, N '-methylene-bisacrylamide, the reaction of initiator generation crosslinking copolymerization is added after logical nitrogen excluding air, realize the surface imprinted of bovine serum albumin molecule, form bovine serum albumin molecular surface engram microballoon;
Step 4, after bovine serum albumin molecular surface engram microballoon elutriant is rinsed repeatedly, use distilled water flushing again, be then dried to constant weight with vacuum drying oven, obtain the bovine serum albumin molecular surface engram microballoon that a large amount of template molecule imprinted cavity is left on surface.
The content containing cross-linking polyvinyl alcohol microballoon in the acetone soln of cross-linking polyvinyl alcohol microballoon in described step one is 3 ~ 8%; The content of the described methacrylic chloride added is 3 ~ 10% of acetone soln, and temperature of reaction is 25 ~ 50 DEG C, and the reaction times is 5 ~ 10h;
In described step 2, the mol ratio of acrylyl oxy-ethyl-trimethyl salmiac and bovine serum albumin is 100:1 ~ 500:1;
The amount being bonded with the modification microballoon of a large amount of methacrylate based group added in described step 3 is 0.5 ~ 5% of described Host-guest complex, described N, the add-on of N '-methylene-bisacrylamide is 0.1 ~ 0.5% of host-guest mixture, described initiator is ammonium persulphate and sodium bisulfite, the add-on of described ammonium persulphate is 0.05 ~ 0.1% of Host-guest complex, the add-on of described sodium bisulfite is 0.02 ~ 0.05% of Host-guest complex, temperature of reaction is 25 ~ 50 DEG C, and the reaction times is 10 ~ 15h.
Elutriant described in described step 4 is sodium chloride solution, and the concentration of described sodium chloride solution is 1 ~ 4mol/L.
The present invention selects bovine serum albumin to be model protein, exploratory development protein molecule engram new technology, its innovation is: based on (1) electrostatic interaction between template protein-function monomer, the trace of protein is implemented in water medium, so both expand the range of choice of monomer, can imprinting effect be improved again, and effectively improve the movability of protein, solvability and stability; (2) mode adopting graft polymerization and printing process synchronously to carry out achieves the graft polymerization of monomer and the molecular surface engram of protein template molecule crosslinked microsphere is surperficial, so both improve the imprinting efficiency (adsorption selectivity) of protein and bonding properties (identification selection), make again the easy wash-out of microsphere.
Result of study of the present invention is that development proteins molecularly imprinted technique selectivity provides new molecular designing thinking, will have positive reference value in protein separation and purification art.
Embodiment
Below in conjunction with embodiment, the present invention is further elaborated:
A preparation method for bovine serum albumin molecular surface imprinting polymer microballoon, comprises the steps:
Step one, the cross-linking polyvinyl alcohol microballoon of 3 ~ 8% is soaked in acetone soln and makes it fully swelling, add the methacrylic chloride of 3 ~ 10 % and a small amount of acid binding agent sodium carbonate again, 25 ~ 50 DEG C of isothermal reaction 5 ~ 10h, obtained surface bond has the modification microballoon of a large amount of methacrylate based group;
Step 2, in neutral aqueous solution, by means of strong electrostatic interaction, numerous cationic monomer acrylyl oxy-ethyl-trimethyl salmiac is automatically in conjunction with around bovine serum albumin macromole: namely in the phosphate buffered saline buffer of neutrality, add the acrylyl oxy-ethyl-trimethyl salmiac of 0.5 ~ 5%, be that 100:1 ~ 500:1 adds bovine serum albumin according to the mol ratio of acrylyl oxy-ethyl-trimethyl salmiac and bovine serum albumin, stirring forms Host-guest complex after making their interaction for some time;
Step 3, moves into described Host-guest complex and is equipped with in the four-hole boiling flask of reflux condensing tube, agitator and thermometer; Add the modification microballoon of 0.5 ~ 5%, soak for some time, then add the N of 0.1 ~ 0.5%, N '-methylene-bisacrylamide, logical nitrogen 30min, the air in eliminating system; System is warming up to 25 ~ 50 DEG C; also the ammonium persulphate of 0.05 ~ 0.1% and the sodium bisulfite of 0.02 ~ 0.05% is added under agitation in nitrogen protection; make surface that graft crosslinking copolymerization occur, 10 ~ 15h is carried out in reaction, realizes the surface imprinted microballoon of bovine serum albumin molecule.
Step 4, the surface imprinted microballoon of the bovine serum albumin molecule of step 3 gained is leached, with the abundant wash-out of 1 ~ 4mol/L sodium chloride solution, till can't detect bovine serum albumin molecule in elutriant, then use distilled water repetitive scrubbing, namely vacuum-drying obtain and surperficially leave a large amount of template molecule imprinted cavity bovine serum albumin molecular surface engram microballoon.
Embodiment 1
2 g cross-linking polyvinyl alcohol microballoons are soaked in the acetone soln of 40 mL and make it fully swelling, then add the methacrylic chloride of 2 mL and a small amount of acid binding agent sodium carbonate, 40 DEG C of isothermal reaction 10 h, obtained modification microballoon.
3.1 g template molecule bovine serum albumins are dissolved in the phosphate buffered saline buffer of 95 mL pH=7.4, add 5 mL monomer propylene acyloxyethyl trimethyl ammonium chlorides, after making their interaction for some time, solution is moved into and is equipped with in the four-hole boiling flask of reflux condensing tube, agitator and thermometer; Add 1 g modification microballoon, soak 12 h, then add 0.16 g linking agent N, N '-methylene-bisacrylamide, logical nitrogen 30min, the air in eliminating system; System is warming up to 35 DEG C, also adds 0.058 g ammonium persulphate and 0.029 g sodium bisulfite under agitation in nitrogen protection, make surface grafting crosslinking reaction carry out 12 h; After reaction terminates, leached by microballoon, with the abundant wash-out of 2mol/L sodium chloride solution, till can't detect bovine serum albumin molecule in elutriant, then use distilled water repetitive scrubbing, namely vacuum-drying obtain bovine serum albumin molecular surface engram microballoon.
Embodiment 2
4 g cross-linking polyvinyl alcohol microballoons are soaked in the acetone soln of 50 mL and make it fully swelling, then add the methacrylic chloride of 5 mL and a small amount of acid binding agent sodium carbonate, 50 DEG C of isothermal reaction 5 h, obtained modification microballoon.
1.8 g template molecule bovine serum albumins are dissolved in the phosphate buffered saline buffer of 95 mL pH=7.4, add 5 mL monomer propylene acyloxyethyl trimethyl ammonium chlorides, after making their interaction for some time, solution is moved into and is equipped with in the four-hole boiling flask of reflux condensing tube, agitator and thermometer; Add 3g modification microballoon, soak 12 h, then add 0.1g linking agent N, N '-methylene-bisacrylamide, logical nitrogen 30min, the air in eliminating system; System is warming up to 25 DEG C, also adds 0.072 g ammonium persulphate and 0.039 g sodium bisulfite under agitation in nitrogen protection, make surface grafting crosslinking reaction carry out 10 h; After reaction terminates, leached by microballoon, with the abundant wash-out of 1mol/L sodium chloride solution, till can't detect bovine serum albumin molecule in elutriant, then use distilled water repetitive scrubbing, namely vacuum-drying obtain bovine serum albumin molecular surface engram microballoon.
Embodiment 3
1 g cross-linking polyvinyl alcohol microballoon is soaked in the acetone soln of 50 mL and makes it fully swelling, then add the methacrylic chloride of 5 mL and a small amount of acid binding agent sodium carbonate, 30 DEG C of isothermal reaction 8 h, obtained modification microballoon.
5 g template molecule bovine serum albumins are dissolved in the phosphate buffered saline buffer of 95 mL pH=7.4, add 10 mL monomer propylene acyloxyethyl trimethyl ammonium chlorides, after making their interaction for some time, solution is moved into and is equipped with in the four-hole boiling flask of reflux condensing tube, agitator and thermometer; Add 5g modification microballoon, soak 12 h, then add 0.48g linking agent N, N '-methylene-bisacrylamide, logical nitrogen 30min, the air in eliminating system; System is warming up to 50 DEG C, also adds 0.098g ammonium persulphate and 0.045 g sodium bisulfite under agitation in nitrogen protection, make surface grafting crosslinking reaction carry out 15 h; After reaction terminates, leached by microballoon, with the abundant wash-out of 4mol/L sodium chloride solution, till can't detect bovine serum albumin molecule in elutriant, then use distilled water repetitive scrubbing, namely vacuum-drying obtain bovine serum albumin molecular surface engram microballoon.
Embodiment 4
The research of adsorption selectivity
Bovine serum albumin phosphate buffered saline buffers different for 20 mL concentration is placed in respectively the tool plug Erlenmeyer flask of several 50 mL, add the trace microballoon that the quality prepared according to embodiment 1-3 accurately taken is 0.03g, in 25 DEG C of constant temperature oscillation 10h, centrifugation, recording the saturated binding capacity of bovine serum albumin in supernatant liquor is 108mg/g, record according to same method that to prepare the saturated binding capacity of bovine serum albumin molecular surface engram microballoon to N,O-Diacetylmuramidase according to embodiment 1-3 be 0.03mg/g, the saturated binding capacity of bovine hemoglobin is 0.67mg/g, illustrate that bovine serum albumin molecular surface engram microballoon does not have adsorptivity to N,O-Diacetylmuramidase and bovine hemoglobin, and to bovine serum albumin molecule, there is very high adsorption selectivity.
Embodiment 5
The research of identification selection performance
The binary liquid mixture of 16.0 μm of mol/L bovine serum albumins and bovine hemoglobin is with pH=7.4 phosphate buffer soln compound concentration, get 20 mL mixing solutionss in tool plug Erlenmeyer flask, the quality prepared according to exemplifying embodiment 1-3 adding precise is the bovine serum albumin molecular surface engram microballoon of 0.03g, 10 h that vibrate in 25 DEG C of constant temperature oscillators make combination reach balance, centrifugation, trace microballoon is 60.22 to the selectivity coefficient of bovine serum albumin, be 1.485 to the selectivity coefficient of bovine hemoglobin, show that bovine serum albumin molecular surface engram microballoon has special identification selection to bovine serum albumin.
Claims (5)
1. a preparation method for bovine serum albumin molecular surface imprinting polymer microballoon, is characterized in that: comprise the steps:
Step one, adds in the acetone soln containing cross-linking polyvinyl alcohol microballoon by methacrylic chloride and a small amount of acid binding agent sodium carbonate, and a large amount of polymerizable double bond is introduced microsphere surface, forms the modification microballoon being bonded with a large amount of methacrylate based group;
Step 2, in neutral aqueous solution, forms Host-guest complex with bovine serum albumin in conjunction with mix and blend by acrylyl oxy-ethyl-trimethyl salmiac;
Step 3, the modification microballoon being bonded with a large amount of methacrylate based group is added in Host-guest complex, add N again, N '-methylene-bisacrylamide, the reaction of initiator generation crosslinking copolymerization is added after logical nitrogen excluding air, realize the surface imprinted of bovine serum albumin molecule, form bovine serum albumin molecular surface engram microballoon;
Step 4, after bovine serum albumin molecular surface engram microballoon elutriant is rinsed repeatedly, use distilled water flushing again, be then dried to constant weight with vacuum drying oven, obtain the bovine serum albumin molecular surface engram microballoon that a large amount of template molecule imprinted cavity is left on surface.
2. the preparation method of a kind of bovine serum albumin molecular surface imprinting polymer microballoon according to claim 1, it is characterized in that: the content containing cross-linking polyvinyl alcohol microballoon in the acetone soln of cross-linking polyvinyl alcohol microballoon described in step one is 3 ~ 8%, the content of the described methacrylic chloride added is 3 ~ 10% of acetone soln, temperature of reaction 25 ~ 50 DEG C, reaction times 5 ~ 10h.
3. the preparation method of a kind of bovine serum albumin molecular surface imprinting polymer microballoon according to claim 1, is characterized in that: the mol ratio of acrylyl oxy-ethyl-trimethyl salmiac described in step 2 and bovine serum albumin is 100:1 ~ 500:1.
4. the preparation method of a kind of bovine serum albumin molecular surface imprinting polymer microballoon according to claim 1, it is characterized in that: the add-on being bonded with the modification microballoon of a large amount of methacrylate based group described in step 3 is 0.5 ~ 5% of described Host-guest complex, described N, the add-on of N '-methylene-bisacrylamide is 0.1 ~ 0.5% of described host-guest mixture, described initiator is ammonium persulphate and sodium bisulfite, described ammonium persulphate add-on is 0.05 ~ 0.1% of Host-guest complex, described sodium bisulfite add-on is 0.02 ~ 0.05% of Host-guest complex, temperature of reaction 25 ~ 50 DEG C, reaction times 10 ~ 15h.
5. the preparation method of a kind of bovine serum albumin molecular surface imprinting polymer microballoon according to claim 1, it is characterized in that: elutriant described in step 4 is sodium chloride solution, the concentration of described sodium chloride solution is 1 ~ 4mol/L.
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| CN104744702A (en) * | 2015-03-26 | 2015-07-01 | 华中农业大学 | Bovine serum albumin surface molecular imprinted polymer and preparation method thereof |
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| CN105175639A (en) * | 2015-11-02 | 2015-12-23 | 中北大学 | Method for preparing trypsin adsorption microbeads with grafting brushes |
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| CN105669918A (en) * | 2016-02-25 | 2016-06-15 | 中北大学 | Preparation method of trypsin surface imprinted microspheres by taking methacrylic acid as monomer |
| CN107314997A (en) * | 2017-06-30 | 2017-11-03 | 三峡大学 | Bioprotein trace hydrogel surface strengthens the preparation method of Raman scattering substrate |
| CN108409906A (en) * | 2018-03-16 | 2018-08-17 | 福州大学 | A kind of ionic hydrogels and preparation method thereof of alternative absorption bovine serum albumin |
| CN108409906B (en) * | 2018-03-16 | 2019-06-07 | 福州大学 | A kind of ionic hydrogels and preparation method thereof of alternative absorption bovine serum albumin |
| CN109517170A (en) * | 2018-11-01 | 2019-03-26 | 西安交通大学 | Bovine serum albumin(BSA) magnetism bionic immune analysis kit and its application |
| WO2021008215A1 (en) * | 2019-07-18 | 2021-01-21 | 广东省医疗器械研究所 | Polymer composite microsphere, preparation method therefor and use thereof |
| CN110478943A (en) * | 2019-07-25 | 2019-11-22 | 湖北大学 | The preparation method of phosphorylation serine imprinted polymer Microcolumn |
| CN111303347A (en) * | 2020-03-12 | 2020-06-19 | 蚌埠学院 | Preparation method of core-shell type temperature-sensitive protein molecularly imprinted polymer microspheres |
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Effective date of registration: 20210715 Address after: 030006 room 503, block C, 529 south central ring street, Taiyuan learning District, Taiyuan Xiaodian District, Shanxi. Patentee after: SHANXI TIEJU ENVIRONMENTAL PROTECTION TECHNOLOGY Co.,Ltd. Address before: 030051 No. 3, Xueyuan Road, Shanxi, Taiyuan Patentee before: NORTH University OF CHINA |