CN113087860A - Micron-sized magnetic fluorescent coding microsphere and preparation method thereof - Google Patents
Micron-sized magnetic fluorescent coding microsphere and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a micron-sized magnetic fluorescent coding microsphere and a preparation method thereof, wherein the preparation method comprises the following steps: carrying out polymerization reaction on monodisperse magnetic microspheres, main monomers, a cross-linking agent, an initiator and fluorescent quantum dots in an organic reaction medium to form a polymer shell layer on the surfaces of the monodisperse magnetic microspheres; the fluorescent quantum dots are modified by a polymer containing double bonds; in the process of polymerization reaction, the fluorescent quantum dots are embedded into the polymer shell layer on the surface of the monodisperse magnetic microsphere in a polymerization mode, so that the micron-sized magnetic fluorescent coding microsphere is obtained. The micron-sized magnetic fluorescent coding microsphere prepared by the invention has good uniformity, the size of 4-7 um, higher magnetic responsiveness and excellent fluorescent property.
Description
Technical Field
The invention relates to the technical field of polymer microsphere synthesis, in particular to a micron-sized magnetic fluorescent coding microsphere and a preparation method thereof.
Background
The fluorescent microsphere is obtained by fixing fluorescent components in the interior or on the surface of the polymer microsphere in an embedding or chemical coupling mode, and a plurality of coding arrays can be formed by means of the difference of the microsphere size and the difference of the types and the contents of the fluorescent components, so that the fluorescent coding microsphere is obtained. The liquid phase chip technology based on the fluorescent coding microspheres can realize the quantification of various proteins, cytokines and the like in the same sample by respectively marking various fluorescent coding microspheres with different biological probe molecules.
The magnetic fluorescent coding microspheres are obtained by introducing magnetic components on the basis of the original fluorescent microspheres, redundant impurities in the reaction can be removed by means of a cleaning mode of magnetic separation, the operation is simple and convenient, and the sensitivity and the accuracy of detection can be improved. Therefore, the magnetic fluorescent coding microspheres with uniform size, high fluorescence yield and good stability become a new research hotspot.
At present, the preparation methods of the magnetic fluorescent coding microspheres mainly comprise a direct synthesis method and a swelling method. The direct synthesis method is to introduce magnetic particles and fluorescent components in the synthesis process of the polymer microsphere, and the magnetic nanoparticles are introduced in the synthesis process of the polymer microsphere in patent CN02139365.6, and then fluorescent dye is doped in the magnetic nanoparticles, so that the magnetic fluorescent microsphere is successfully obtained. However, the microspheres prepared in this way have poor homogeneity and large difference in magnetism/fluorescence among microspheres. The swelling method is to take a pre-synthesized monodisperse polymer microsphere as a matrix, simultaneously or step by step introduce magnetic particles and fluorescent components into the polymer microsphere in a swelling mode, and patent CN201010129442.8 swells the monodisperse carboxylated polystyrene microsphere, and then simultaneously add quantum dots and magnetic nanoparticles, thereby preparing the magnetic fluorescent microsphere. However, the microspheres prepared in this way have low magnetic content and poor magnetic response, and the coexistence of the magnetic particles and the quantum dots can affect the stability and fluorescence quantum yield of the quantum dots.
Disclosure of Invention
The technical problem to be solved by the invention is to provide a preparation method of the micron-sized magnetic fluorescent coding microsphere, and the magnetic fluorescent coding microsphere prepared by the method has good uniformity, the size of 4-7 microns, higher magnetic responsiveness and excellent fluorescent property.
In order to solve the technical problems, the invention provides the following technical scheme:
in a first aspect, the present invention provides a method for preparing a micron-sized magnetic fluorescent coding microsphere, comprising the following steps:
carrying out polymerization reaction on monodisperse magnetic microspheres, main monomers, a cross-linking agent, an initiator and fluorescent quantum dots in an organic reaction medium to form a polymer shell layer on the surfaces of the monodisperse magnetic microspheres;
the fluorescent quantum dots are modified by a polymer containing double bonds; in the process of polymerization reaction, the fluorescent quantum dots are embedded into the polymer shell layer on the surface of the monodisperse magnetic microsphere in a polymerization mode, so that the micron-sized magnetic fluorescent coding microsphere is obtained.
Further, the monodisperse magnetic microsphere is a magnetic microsphere with the surface modified by a high cross-linked polymer, magnetic particles are uniformly distributed in the high cross-linked polymer, and the cross-linking degree of the high cross-linked polymer is 20-70%.
Further, the monodisperse magnetic microsphere is a surface carboxyl core-shell superparamagnetic polymer microsphere prepared according to the method described in chinese patent CN 108467461A.
Further, the main monomer is a monomer commonly used for polymer microspheres, including but not limited to styrene and methyl methacrylate.
Further, the initiator is an oil-soluble initiator, and can be a peroxide initiator, such as benzoyl peroxide and the like; azo initiators such as azobisisobutyronitrile and the like may also be used. The amount of the initiator is preferably 0.5 to 2.0 wt% of the total amount of the monomers.
Further, the organic reaction medium comprises one or a mixture of more than two of ethanol, isopropanol and acetonitrile.
Further, the crosslinking agent is a monomer containing at least two unsaturated double bonds, including but not limited to one or more of divinylbenzene, ethylene glycol dimethacrylate, and N, N' -methylenebisacrylamide.
Further, the fluorescent quantum dots are core-shell CdSe/ZnS quantum dots or CdS/ZnS quantum dots with surfaces modified by oleic acid, and the size of the fluorescent quantum dots is 2-10 nm. The invention uses surface oleic acid modified quantum dots, and can directly participate in polymerization reaction by virtue of unsaturated double bonds in oleic acid molecules; meanwhile, the quantum dots are oil-soluble, have better affinity with polymers, and are beneficial to improving the embedding efficiency of the quantum dots.
Further, the mass percentage of the fluorescent quantum dots in the monodisperse magnetic microspheres is 0.5-10%. The coding array is obtained by changing the size and the concentration of the fluorescent quantum dots, so that various magnetic fluorescent coding microspheres can be prepared.
Further, the raw material of the polymerization reaction further comprises a functional monomer, wherein the functional monomer is a monomer containing both a functional group and an unsaturated double bond, and includes but is not limited to one or more of a carboxyl functional monomer, an amino functional monomer and an epoxy functional monomer.
Wherein, the carboxyl functional monomer includes but is not limited to acrylic acid, methacrylic acid and undecylenic acid, the amino functional monomer includes but is not limited to aminostyrene and acrylamide, and the epoxy functional monomer includes but is not limited to glycidyl methacrylate.
The functional monomer is introduced in the polymerization process, so that the magnetic fluorescent microsphere with the surface containing functional groups can be directly prepared, and the subsequent biological application is facilitated.
Further, the mass ratio of the main monomer, the functional monomer and the cross-linking agent is 30-70%, 10-20% and 30-50% respectively.
In a second aspect, the invention further provides the micron-sized magnetic fluorescent coding microsphere prepared by the method in the first aspect.
Compared with the prior art, the invention has the beneficial effects that:
1. the invention is based on high cross-linking monodisperse magnetic microspheres, and the fluorescent quantum dots modified by double-bond polymers are embedded into the polymer shell layer on the surface of the magnetic microspheres in a polymerization manner. The magnetic fluorescent coding microsphere prepared by the method has good uniformity, the size of 4-7 um, higher magnetic responsiveness and excellent fluorescence performance. By adjusting the size and the use concentration of the fluorescent quantum dots, various different magnetic fluorescent coding microspheres can be conveniently prepared, and the requirements of multi-component analysis and detection in flow fluorescence can be met.
2. The invention is based on the cross-linked monodisperse magnetic polymer microsphere, the size reaches 3-5 um, and a method is provided for preparing the large-size uniform fluorescent coding microsphere; the monodisperse magnetic polymer microspheres are modified by high cross-linked polymers, so that the integrity of the magnetic microspheres in subsequent organic medium repolymerization is ensured.
3. The invention takes the quantum dots as the fluorescent substance, and the prepared fluorescent coding microsphere has high fluorescent yield, strong signal and narrow emission spectrum.
Drawings
FIG. 1 is the fluorescence signal intensity of the surface carboxyl magnetic fluorescent microsphere prepared in example 1;
FIG. 2 is an SEM image of surface amino magnetic fluorescent microspheres prepared in example 2;
FIG. 3 is the scattered light signal of the surface amino magnetic fluorescent microspheres prepared in example 2 on a flow cytometer.
Detailed Description
The present invention is further described below in conjunction with the following figures and specific examples so that those skilled in the art may better understand the present invention and practice it, but the examples are not intended to limit the present invention.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.
The experimental methods used in the following examples are conventional methods unless otherwise specified, and materials, reagents and the like used therein are commercially available without otherwise specified.
Example 1
The surface highly crosslinked carboxyl magnetic microspheres were prepared according to the method described in patent ZL201810169129.3, with the parameters adjusted, the average particle diameter of 3 μm and CV of 3.1%.
Weighing 2g of the magnetic microspheres, carrying out magnetic separation, and washing with absolute ethyl alcohol once. 200g of isopropanol, 10g of styrene, 2g of methacrylic acid, 0.1g of CdSe/ZnS fluorescent quantum dots, 8g of N, N' -methylenebisacrylamide and 0.2g of azodiisobutyronitrile are sequentially added, and after ultrasonic dispersion is carried out for 10min, the mixture is added into a reaction bottle, water bath is carried out at 70 ℃, stirring is carried out at 200rpm, and reaction is carried out for 10 h. Sampling and carrying out magnetic separation, and carrying out magnetic separation and cleaning by using isopropanol and deionized water in sequence to obtain the magnetic fluorescent microsphere with the surface carboxyl, wherein the size is 3.5 mu m.
FIG. 1 is a fluorescence spectrum of the surface carboxyl magnetic fluorescent microsphere prepared in example 1. As can be seen from the figure, the microspheres emit intense fluorescence at 500nm with a narrow emission spectrum.
Example 2
The surface highly crosslinked carboxyl magnetic microspheres are prepared according to the method described in patent ZL201810169129.3 by adjusting parameters, and have the average particle diameter of 4.8 mu m and the CV of 2.5 percent.
Weighing 2g of the magnetic microspheres, carrying out magnetic separation, and washing with absolute ethyl alcohol once. Adding 200g of acetonitrile, 12g of methyl methacrylate, 5g of acrylamide, 0.2g of CdSe/ZnS fluorescent quantum dots, 8g of ethylene glycol dimethacrylate and 0.25g of azodiisobutyronitrile in sequence, ultrasonically dispersing for 10min, adding into a reaction bottle, carrying out water bath at 80 ℃, stirring at 200rpm, and reacting for 10 h. And (3) sampling, carrying out magnetic separation, and carrying out magnetic separation and cleaning by using ethanol and deionized water in sequence to obtain the magnetic fluorescent microspheres with amino groups on the surfaces, wherein the size of the microspheres is 5.6 microns.
FIG. 2 is an SEM image of the surface amino magnetic fluorescent microspheres prepared in example 2, and it can be seen that the prepared microspheres have uniform size.
FIG. 3 is the scattered light signal of the surface amino magnetic fluorescent microsphere prepared in example 2 on a flow cytometer, and it can be seen from the figure that the microsphere has good uniformity and dispersibility under a liquid phase system.
In summary, the magnetic fluorescent coding microsphere prepared by the invention is based on the monodisperse high cross-linked magnetic polymer microsphere, quantum dots are introduced into a polymer shell layer on the surface in a later polymerization mode, and various magnetic fluorescent coding microspheres can be obtained by changing the size and concentration of the quantum dots. The magnetic fluorescent coding microsphere prepared by the method has the characteristics of uniform size, high fluorescence yield and easiness in surface functionalization.
The above-mentioned embodiments are merely preferred embodiments for fully illustrating the present invention, and the scope of the present invention is not limited thereto. The equivalent substitution or change made by the technical personnel in the technical field on the basis of the invention is all within the protection scope of the invention. The protection scope of the invention is subject to the claims.
Claims (10)
1. A preparation method of micron-sized magnetic fluorescent coding microspheres is characterized by comprising the following steps:
carrying out polymerization reaction on monodisperse magnetic microspheres, main monomers, a cross-linking agent, an initiator and fluorescent quantum dots in an organic reaction medium to form a polymer shell layer on the surfaces of the monodisperse magnetic microspheres;
the fluorescent quantum dots are modified by a polymer containing double bonds; in the process of polymerization reaction, the fluorescent quantum dots are embedded into the polymer shell layer on the surface of the monodisperse magnetic microsphere in a polymerization mode, so that the micron-sized magnetic fluorescent coding microsphere is obtained.
2. The method according to claim 1, wherein the monodisperse magnetic microsphere is a magnetic microsphere with a surface modified by a highly cross-linked polymer, the magnetic particles are uniformly distributed in the highly cross-linked polymer, and the degree of cross-linking of the highly cross-linked polymer is 20% to 70%.
3. The method for preparing micron-sized magnetic fluorescent coding microspheres according to claim 2, wherein the monodisperse magnetic microspheres are surface carboxyl core-shell superparamagnetic polymer microspheres prepared according to the method described in chinese patent CN 108467461A.
4. The method of claim 1, wherein the main monomer comprises styrene and/or methyl methacrylate.
5. The method for preparing micron-sized magnetic fluorescence-encoded microspheres according to claim 1, wherein the cross-linking agent comprises one or more of divinylbenzene, ethylene glycol dimethacrylate, and N, N' -methylenebisacrylamide; the initiator comprises a peroxide initiator and an azo initiator, and the dosage of the initiator is 0.5-2.0 wt% of the total amount of the monomers; the organic reaction medium comprises one or more than two of ethanol, isopropanol and acetonitrile.
6. The preparation method of the micron-sized magnetic fluorescent coding microsphere of claim 1, wherein the fluorescent quantum dots are core-shell CdSe/ZnS quantum dots or CdS/ZnS quantum dots with surfaces modified by oleic acid, and the size of the fluorescent quantum dots is 2-10 nm.
7. The method for preparing micron-sized magnetic fluorescent coding microspheres according to claim 1, wherein the fluorescent quantum dots account for 0.5-10% of the monodisperse magnetic microspheres by mass.
8. The method for preparing micron-sized magnetic fluorescent coding microspheres according to claim 1, wherein raw materials for the polymerization reaction further comprise functional monomers, wherein the functional monomers are monomers simultaneously containing functional groups and unsaturated double bonds, and comprise one or more of carboxyl functional monomers, amino functional monomers and epoxy functional monomers;
the carboxyl functional monomer comprises acrylic acid, methacrylic acid and undecylenic acid, the amino functional monomer comprises aminostyrene and acrylamide, and the epoxy functional monomer comprises glycidyl methacrylate.
9. The method for preparing the micron-sized magnetic fluorescent coding microsphere as claimed in claim 8, wherein the mass ratio of the main monomer, the functional monomer and the cross-linking agent is 30-60%, 10-20% and 30-50% respectively.
10. Micron-sized magnetic fluorescently encoded microspheres made according to the method of any of claims 1-9.
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