CN103304732A - Monodisperse core-shell structure polymer nano particle as well as preparation and application thereof - Google Patents
Monodisperse core-shell structure polymer nano particle as well as preparation and application thereof Download PDFInfo
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Abstract
The invention belongs to the technical field of high molecular materials and analysis and relates to a monodisperse core-shell structure polymer nano particle as well as preparation and application thereof. The polymer nano particle is a core-shell type copolymer of an acrylic acid cross-linking agent and a monoene phenylboronic acid functional monomer; and the polymer nano particle is prepared by using a one-pot method, that is, precipitation polymerization with the combination of in-situ package strategy. Synthesis steps of the conventional core-shell structure polymer particles are simplified, and the polymer nano particle has the characteristics of rapidness, convenience and easiness, low cost, multiple boric acid functional monomers on the surface, and the like. The polymer nano particle can be used for separating or enriching glycoprotein with a 1,2-cis-glycol structure, and has good practical values and application prospects in the fields of proteomics and the like.
Description
Technical field
The present invention relates to the enrichment of glycoprotein, specifically a kind of single distributed nuclei shell structure polymer nano-particle and preparation thereof and in the glycoprotein enrichment, using.
Background technology
As everyone knows, the composition of protein is extremely complicated and constantly change, even at different cells or the isocellular different times of same species, all there is significant difference in the composition of protein.Especially for posttranslational modification albumen, often become focus and the difficult point of proteomics research because of its low abundance and complicacy.
Glycoprotein plays an important role in the biological procedureses such as cell adhesion, signal transduction, immunity and tumour generation as the important posttranslational modification albumen of a class.In recent years, although mass-spectrometric technique has become the effective tool of research glycoprotein glycosylation site information and glycan structure ownership, but because the glycoprotein abundance is low, that glycopeptide accounts for total peptide section ratio is little, often covered by abundant non-glycopeptide during analyzing and testing, therefore before analyzing, need to carry out selective enrichment to glycoprotein/glycopeptide.
The most frequently used glycoprotein enriching method comprises the lectin affinity chromatography, hydrazides and boric acid functionalization material etc. at present.Wherein borate method is to utilize the reversible action between o-dihydroxy and material surface boric acid base group on the sugar chain and the selective separation that realizes glycoprotein.This method step is simple and efficient, has avoided the destruction of sugar chain structure, and enriched product and mass spectrum compatibility.Have and study successfully 3-amino-benzene boric acid is immobilized in macropore silicon ball, ferriferrous oxide particles and nm gold particles surface (Xu Y, Wu Z, Zhang L, Lu H, Yang P, Webley P.A, Zhao D.Anal.Chem.2009,81,503-508; Zhang L, Xu Y, Yao H, Xie L, Yao J, Lu H, Yang P.Chem.--Eur.J.2009,15,10158-10166; Tang J, Liu Y, Qi D, Yao G, Deng C, Zhang X.Proteomics.2009,9,5046-5055), yet the rear modification grafting strategy efficient that adopts is lower and step is extremely loaded down with trivial details.There is the mode of research and utilization copolymerization to prepare boric acid functionalization integral post (L Ren, Y Liu, M Dong, Z.Liu.J.Chromatogr.A.2009,1216,8421-8425; Z Lin, J Pang, HYang, Z Cai, L Zhang, G.Chen, Chem.Commun.2011,47,9675-9677; Y Liu, L Ren, Z Liu.Chem.Commun.2011,47,5067-5069), though the boric acid bonding efficiency improves and the glycoprotein concentration effect is better, the restriction of the column capacity of integral post own is so that materials is unfavorable for the pre-treatment of mass-producing protein sample.
Summary of the invention
For above deficiency, the purpose of this invention is to provide and a kind ofly prepare easyly, have the good single distributed nuclei shell structure polymer nano-particle of glycoprotein concentration effect and specificity.Another purpose provides a kind of efficiently " one kettle way " nucleocapsid structure preparation strategy.
For achieving the above object, the technical solution used in the present invention is:
A kind of single distributed nuclei shell structure polymer nano-particle, it is characterized in that: its particle diameter is 400-700nm, the polydispersity coefficient of granularity is that (" polydispersity coefficient " is 0.03-0.05 to 0.03-0.05, polydispersity coefficient wherein: refer to the heterogeneity index that dynamic light scattering (DLS) particle size analyzer is measured, also can be referred to as: the heterogeneity index of particle size)
With 4-vinylphenylboronic acid, N, N '-methylene-bisacrylamide is as monomer, and the mode by precipitation polymerization in water alcohol mixed system at first makes the polymkeric substance parent nucleus; Subsequently without steps such as any centrifugal, washing and transfers, under original polymerizing condition, continue in system, to add 4-vinylphenylboronic acid function monomer, thereby " one kettle way " makes single distributed nuclei shell structure polymer nano-particle of rich surface boronic acid containing functional group.
The concrete steps of described single distributed nuclei shell structure polymer nano-particle preparation are as follows,
1) form polymer core: 4-vinylphenylboronic acid, N, N '-methylene-bisacrylamide monomer and initiator were scattered in the water-ethanol mixed solvent, made polymer core at 60-80 ℃ of lower polyreaction 12-24 hour.
2) original position is wrapped up: continue to add the ethanolic soln that contains 4-vinylphenylboronic acid function monomer and initiator in resulting polymers nuclear solution system, 60-80 ℃ of lower the reaction 4-10 hour.
3) centrifugation obtains the nucleocapsid structure polymer nano-particle, washing with alcohol number time, and vacuum-drying is to constant weight.
Step 1) ethanol accounts for the 10%-30% of total solvent volume in the described water-ethanol mixing solutions; 4-vinylphenylboronic acid and N, the mol ratio of N '-methylene-bisacrylamide monomer is 1: 4-8, total moles monomer concentration is 0.1-0.3mol/L; Initiator is Diisopropyl azodicarboxylate, and its add-on accounts for the 1-3% of monomer total mass.
Step 2) the mole number concentration of the 4-vinylphenylboronic acid of described adding is 0.1-0.3mol/L; Initiator is Diisopropyl azodicarboxylate, and its quality accounts for the 10-20% of rear adding 4-vinylphenylboronic acid function monomer quality; After add ending, ethanol accounts for the 20%-40% of the total solvent volume that water and ethanol consists of.
The single distributed nuclei shell structure polymer nano-particle that makes is used for the selective enrichment of glycoprotein.
" one kettle way ", be that precipitation polymerization is in conjunction with original position parcel strategy, as a kind of simple and efficient nucleocapsid structure polymer nano-particle preparation method, often can be from simple raw material monomer, need not any additive, and without the separation of intermediate, directly obtain the polymer particle of nucleocapsid structure.Have the reaction conditions gentleness, with low cost and advantages of environment protection, this paper adopts " one kettle way " to realize the preparation of single distributed nuclei shell structure polymer nano-particle just.
The present invention has following advantage:
1. the size distribution of nucleocapsid structure polymer nano-particle of the present invention is narrower, realizes single the dispersion.Particle is totally smooth, does not contain any additive and stablizer, has preferably wetting ability.
2. the present invention uses two kinds of monomers in the mixed system of water alcohol, utilizes " one kettle way ", obtains boric acid functionalization nucleocapsid structure polymer nano-particle; By the coupling between active group, the combination that glycoprotein is easy and reversible and particle surface, selective enrichment and the MALDI-TOFMS direct analysis of realization glycoprotein.
3. the formation of polymer core outside 4-vinylphenylboronic acid shell so that a large amount of boric acid functional groups are contained on the surface of nucleocapsid structure polymer nano-particle of the present invention, and has higher glycoprotein loading capacity.
Description of drawings
Fig. 1 is the synthetic schematic diagram of single distributed nuclei shell structure polymer nano-particle.
Fig. 2 is polymkeric substance parent nucleus scanning electron microscope (SEM) photograph a); B) single distributed nuclei shell structure polymer nano-particle scanning electron microscope (SEM) photograph.
Fourier's infrared spectrogram of Fig. 3 list distributed nuclei shell structure polymer nano-particle.The charateristic avsorption band (1373 and 1348cm that boric acid base group occurred
-1)
(horseradish peroxidase is HRP) with non-glycoprotein (bovine serum albumin, BSA) the concentration effect figure of mixing solutions (mass ratio 1: 1) to glycoprotein for Fig. 4 list distributed nuclei shell structure polymer nano-particle.A) stoste; B) supernatant; C) enriched product.
(horseradish peroxidase is HRP) with non-glycoprotein (bovine serum albumin, BSA) the concentration effect figure of mixing solutions (mass ratio 1: 500) to glycoprotein for Fig. 5 list distributed nuclei shell structure polymer nano-particle.A) stoste; B) supernatant; C) enriched product.
Embodiment
The below adopts specific embodiment that technical scheme of the present invention is described further.
1. the preparation of single distributed nuclei shell structure polymer nano-particle
As shown in Figure 1, take by weighing 33.8mg 4-vinylphenylboronic acid (VPBA) and join in the 50mL round-bottomed flask that contains 2mL ethanol ultrasonic 5min.After monomer dissolving, continue in flask, to add 8mL water, 212.2mg N, N '-methylene-bisacrylamide (MBAA) and 5mg Diisopropyl azodicarboxylate (AIBN), ultrasonic until mixture all dissolves.Flask is placed oil bath, be warming up to 70 ℃ from room temperature, and under this temperature, keep stirring, heating 18 hours.After reaction finished, solution was the milk shape, thereby makes the polymkeric substance parent nucleus.
Take by weighing respectively 33.8mg VPBA and 5mg AIBN, ultrasonic dissolution is in 2mL ethanol.This solution is joined in the polymerization system of above-mentioned reaction end, 70 ℃ are stirred down, heated 6 hours, and solution still is the milk shape.After question response finished, stopped heating was cooled to room temperature.With this solution centrifugal (15000g * 20min), abandon supernatant.Adopt ethanolic soln the nucleocapsid structure polymer nano-particle that separation obtains to be washed the centrifugal supernatant of abandoning.Repetitive operation three times is to remove the oligomer chain that forms in unreacted monomer and the reaction.Vacuum-drying is to constant weight, thereby makes single distributed nuclei shell structure polymer nano-particle.
2. the sign of polymer nano-particle
Scanning electron microscope (SEM) photograph as shown in Figure 2, the size distribution of the polymer core that precipitation polymerization makes is narrower, median size is that (Fig. 2 a) for 250nm; The median size of the Multifunctional Aids for Paper--Core-shell Structure Polymer Particles that forms behind the original position parcel is 550nm, and smooth surface, singly disperse, shell thickness is 150nm (Fig. 2 b).
Fourier's infrared spectrum characterization result as shown in Figure 3,1373 and 1348cm
-1The stretching vibration absorption peak that B-O occurred has proved the existence of material mesoboric acid group.
Embodiment 2
1. protein mixed solution preparation
With glycoprotein (horseradish peroxidase, HRP) with non-glycoprotein (bovine serum albumin, BSA) mix at 1: 1 in mass ratio, and be dissolved in (pH 9.0) in the 50mM ammonium bicarbonate buffer solution, thereby make the protein mixed solution that concentration is 100ng/ μ L.
2. selective enrichment glycoprotein
Take by weighing the 1mg nucleocapsid structure polymer nano-particle of embodiment 1 preparation, be scattered in the above-mentioned protein mixed solution of 200 μ L, the gentle concussion of room temperature 2 hours, the centrifugal supernatant of abandoning after reaction finishes.50mM ammonium bicarbonate buffer solution (pH 9.0) detergent number time, the centrifugal supernatant of abandoning.In the material that separation obtains, add 50% acetonitrile solution (trifluoroacetic acid volume fraction 1%) that 20 μ L contain trifluoroacetic acid, the gentle concussion of room temperature 1 hour.The centrifuging and taking supernatant directly carries out MALDI-TOF MS and identifies.
3.MALDI-TOF MS analyzes
0.5 μ L enriched product and 0.5 μ L SA matrix (the 20mg/mL sinapinic acid is dissolved in 60% acetonitrile solution that contains 1% trifluoroacetic acid) are put successively on the MALDI target plate, after the sample spot drying, carried out Mass Spectrometric Identification.MALDI-TOF MS experiment is to carry out on Ultraflex III TOF/TOF (Bruker Daltonics, Bremen, Germany), adopts linear positive ion mode during detection.
As shown in Figure 4, after hud typed polymer nano-particle enrichment, the HRP strength of signal significantly improves (a curve) than stoste; And without the non-specific absorption of BSA, disturb albumen to exist only in (b curve) among the supernatant.Show that material has preferably glycoprotein accumulation ability and good wetting ability (c curve).
Embodiment 3
In order to investigate selectivity and the non-specific absorption of polymer nano-particle in the glycoprotein enrichment process, further carry out interference experiment.HRP and BSA are mixed in mass ratio at 1: 500, and be dissolved in (pH 9.0) in the 50mM ammonium bicarbonate buffer solution, thereby make the protein mixed solution that concentration is 25.05 μ g/ μ L.Take by weighing 1mg nucleocapsid structure polymer nano-particle, carry out glycoprotein enrichment and follow-up MALDI-TOF MS evaluation with the condition of embodiment 2.
As shown in Figure 5, HRP in the stoste is because concentration is extremely low, so that the mass spectrum response signal is suppressed by BSA and can't detect (a curve); After hud typed polymer nano-particle enrichment, the HRP strength of signal significantly improves (c curve); And got rid of the impact of disturbing albumen, made BSA only among supernatant, obtain detecting (b curve).Show that material has high selectivity to glycoprotein.
Claims (8)
1. single distributed nuclei shell structure polymer nano-particle, it is characterized in that: its particle diameter is 400-700nm, the polydispersity coefficient of granularity is 0.03-0.05;
With 4-vinylphenylboronic acid and N, N '-methylene-bisacrylamide is nuclear for 1:4-8 by the polymer particle that precipitation polymerization makes in molar ratio, in the poly-4-vinylphenylboronic acid of nuclear surface in situ parcel, form smooth surface and with the polymer nano-particle of the nucleocapsid structure of boric acid functional group.
2. according to the described single distributed nuclei shell structure polymer nano-particle of claim 1, it is characterized in that: the thickness of shell is 50-250nm, and 4-vinylphenylboronic acid ratio of massfraction in nuclear and shell two-phase is 15-45%.
3. the preparation method of the described single distributed nuclei shell structure polymer nano-particle of claim 1, it is characterized in that: with 4-vinylphenylboronic acid, N, N '-methylene-bisacrylamide is as monomer, in the water-ethanol mixed system, pass through " one kettle way ", be that precipitation polymerization is tactful in conjunction with the original position parcel, obtain a kind of polymer nano-particle with nucleocapsid structure.
4. according to preparation method claimed in claim 3, it is characterized in that:
Concrete steps are as follows:
1) form polymer core: with 4-vinylphenylboronic acid, N, N '-methylene-bisacrylamide monomer and initiator were scattered in the water-ethanol mixed solvent, made polymer core at 60-80 ℃ of lower polyreaction 12-24 hour;
2) original position parcel: in the polymer core solution system that obtains, continue to add the ethanolic soln that contains 4-vinylphenylboronic acid function monomer and initiator, 60-80 ℃ of lower the reaction 4-10 hour;
3) centrifugation obtains the nucleocapsid structure polymer nano-particle, uses washing with alcohol, and vacuum-drying is to constant weight.
5. according to the preparation method of the described single distributed nuclei shell structure polymer nano-particle of claim 4, it is characterized in that: form polymer core period, 4-vinylphenylboronic acid and N, the mol ratio of N '-methylene-bisacrylamide is 1:4-8, total moles monomer concentration is 0.1-0.3mol/L; Original position is wrapped up period, and the mole number concentration that adds the 4-vinylphenylboronic acid in system is 0.1-0.3mol/L.
6. according to the preparation method of the described single distributed nuclei shell structure polymer nano-particle of claim 4, it is characterized in that: described initiator is Diisopropyl azodicarboxylate, nucleation its add-on in period accounts for the 1-3% of monomer (4-vinylphenylboronic acid and N, N '-methylene-bisacrylamide monomer) total mass; Original position parcel its add-on in period accounts for the 10-20% of monomer (the 4-vinylphenylboronic acid function monomer that adds after during the original position parcel) total mass.
7. according to the preparation method of the described single distributed nuclei shell structure polymer nano-particle of claim 4, it is characterized in that: nucleation period, ethanol accounts for the 10%-30% of total solvent volume in the water alcohol mixed system; Original position parcel period, the 4-vinylphenylboronic acid and the initiator that adopt dissolve with ethanol to add, add end after, ethanol accounts for the 20%-40% of the total solvent volume that water and ethanol consists of.
8. the described single distributed nuclei shell structure polymer nano-particle of claim 1 can be used for selective enrichment glycoprotein.
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| CN104610497A (en) * | 2013-11-04 | 2015-05-13 | 复旦大学 | Core-shell structured bioadhesive polymer nanoparticle, and preparation method and application thereof |
| CN105131164A (en) * | 2015-09-18 | 2015-12-09 | 北京化工大学 | Method for preparing monodisperse polymeric microspheres adopting snowman-shaped, dumbbell-shaped, raspberry-shaped or core-shell structure through one-step dispersion polymerization |
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| CN104610497A (en) * | 2013-11-04 | 2015-05-13 | 复旦大学 | Core-shell structured bioadhesive polymer nanoparticle, and preparation method and application thereof |
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| CN107082840B (en) * | 2017-05-05 | 2019-07-23 | 中国科学院理化技术研究所 | A kind of acrylamido phenyl boric acid polymer and its preparation and application |
| CN110028611A (en) * | 2019-05-07 | 2019-07-19 | 中国科学院合肥物质科学研究院 | A kind of monodisperse shell core formula polystyrene microsphere and preparation method thereof |
| CN112430289A (en) * | 2020-11-09 | 2021-03-02 | 南昌大学 | High-selectivity phenylboronic acid functionalized organic polymer and preparation method and application thereof |
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