CN101942066A - Water-soluble polymer magnetic nanoparticle with fluorescence and preparation method thereof - Google Patents
Water-soluble polymer magnetic nanoparticle with fluorescence and preparation method thereof Download PDFInfo
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Abstract
The invention relates to a water-soluble polymer magnetic nanoparticle with the fluorescence and a preparation method thereof. In the invention, the water-soluble polymer/magnetic nanoparticle with fluorescence is synthesized by using acetylacetone metal salt, and the like as raw materials through various organic metal reactions and by adopting an activity-controlled free radical polymerization method. The synthesized material has biological affinity and favorable fluorescence, is a magnetic material with potential and embodies prominent advantages and wide application prospects in the aspect of acquiring multi-level biological information, such as organs, tissue, cells, molecules, and the like in the biomedical application field. The synthetic polymer/magnetic nanoparticle has good stability and can realize further functionalization the nanoparticle by introducing a biocompatible amino group at the tail end of the polymer.
Description
Technical field
The invention belongs to biological functional material technology field, be specifically related to a kind of water-soluble polymers/magnetic nano-particle and preparation method thereof with photoluminescent property.
Background technology
Magnetic nano-particle has special magnetic property, because its behavior can be controlled by externally-applied magnetic field, makes it have a very important role aspect biomedical and the biotechnology applications.Finishing has the ultra-fine magnetic nano-particle of fluorophor to receive much concern, the ultra-fine magnetic nano-particle of combined with fluorescent group has possessed magnetic and photoluminescent property, and it obtains in the biomedical applications field and embodies outstanding advantage and application prospects aspect the multi-level bioinformation such as organ, tissue, cell, molecule.
The present invention is by synthetic polymkeric substance/magnetic nanometer, and polymer ends is introduced the amino of biological functional, and with a spot of fluorophor mark.
Summary of the invention
Technical problem: the biocompatibility that the objective of the invention is to solve magnetic nano-particle with and in problems such as biological detection marks, a kind of epipolic water-soluble polymers magnetic nano-particle and preparation method thereof that has is provided.
Technical scheme: the present invention adopts steps such as high temperature organic phase co-electrodeposition method, the ultra-fine magnetic nanometer that has synthesized the size homogeneous, utilize ATRP to be aggregated in the polymethyl acid glyceride that its surface articulates biocompatibility, and insert amino in polymer ends, realize water-soluble and can on amino, modify various biological functionality groups, in addition, insert a spot of fluorophor.
Synthetic grain size of magnetic nanometer grains homogeneous, it can apply in the organism preferably.Introduce macromolecule chain section--poly (glycidyl methacrylate) (PGMA) on the magnetic nanometer surface, and on polymer P GMA end, introduce amino, the amino biological functionality group that can be used to connect some biomolecules with specific recognition, realize magnetic nanometer biocompatibility and detection effect, the fluorophor mark.
Provided by the invention have that epipolic water-soluble polymers magnetic nanometer is inner to be the magnetic nano particle daughter nucleus, and its structural representation is as follows:
Wherein,
Be MFe
2O
4Magnetic nanometer nuclear, wherein, metal M is a kind of among Fe, Co, the Mn, magnetic nanometer nuclear size homogeneous, FITC is a fluorophor,
Be the poly (glycidyl methacrylate) macromolecular chain, concrete structure is
M is the polymerization degree, and m is 30-100;
Macromolecular chain by on the end group-the COO-group is connected with the magnetic nanometer nuclear phase.
Described magnetic nanometer nuclear has following three kinds of forms:
1) magnetic nanometer nuclear is Fe
3O
4, adhering to poly (glycidyl methacrylate) around the magnetic nanometer, polymer ends is introduced amino and a small amount of fluorescein of biocompatibility, and its structure is as follows:
2) magnetic nanometer nuclear is CoFe
2O
4, adhering to poly (glycidyl methacrylate) around the magnetic nanometer, polymer ends is introduced amino and a small amount of fluorescein of biocompatibility, and its structure is as follows:
3) magnetic nanometer nuclear is MnFe
2O
4, adhering to poly (glycidyl methacrylate) around the magnetic nanometer, polymer ends is introduced amino and a small amount of fluorescein of biocompatibility, and its structure is as follows:
The synthetic method concrete steps of water-soluble polymers/magnetic nanometer with photoluminescent property are as follows:
A. magnetic nanometer nuclear is synthetic: in the dibenzyl ether solvent, ferric acetyl acetonade is 1, and 2-16 glycol, oleic acid, oleyl amine pyrolytic decomposition prepare monodispersed magnetic nanometer, and concrete steps are as follows:
With ferric acetyl acetonade (III), 1,2-16 glycol, oleic acid, oleyl amine are dissolved in the dibenzyl ether,
Stir at the condition lower magnetic force that constantly feeds nitrogen, mixing solutions is heated to 200 ℃ continues 2 hours, be warmed up to 300 ℃ of following reheat one hour then, be cooled to room temperature, add small amount of ethanol, have black precipitate to generate.Centrifugation goes out black precipitate, then it is dispersed in the hexane solution that contains oleic acid and oleyl amine, and the dark solution that centrifugation goes out adds small amount of ethanol once more, and centrifugation goes out black precipitate and is magnetic nanometer.Drying under reduced pressure is at 0-4 ℃ of following cryopreservation;
B. initiator is introduced on magnetic nanometer nuclear surface: the surface that initiator 3-chloropropionic acid is introduced magnetic nanometer nuclear by metathesis, and concrete steps are as follows:
The magnetic nanometer that oleic acid is stable is dispersed in the hexane solution of 3-chloropropionic acid, under nitrogen protection, normal temperature magnetic agitation 24 hours, centrifugation obtains introducing the magnetic nanometer of initiator, wash repeatedly and drying under reduced pressure with normal hexane, at 0-4 ℃ of following cryopreservation;
C. synthesizing of water miscible polymkeric substance magnetic nanometer: on the magnetic nanometer that is connected to 3-chloropropionic acid initiator, by the synthetic poly (glycidyl methacrylate)/magnetic nanometer of active controllable free-radical method, concrete steps are as follows:
The magnetic nanometer of introducing initiator directly is dissolved in the tetrahydrofuran (THF) (THF), logical nitrogen 15 minutes adds CuCl and N N N ' N ' N, and " pentamethyl-diethylenetriamine, logical again nitrogen 10 minutes; with the mixing solutions sealing was 50 ℃ of water-bath lower magnetic forces stirrings 18 hours.After finishing, reaction uses THF diluting reaction mixed solution, centrifugation gained mixed solution, removal cupric precipitation splashes into residual mixed liquor in the ethanol, obtains the Vandyke brown precipitation, with resolution of precipitate in THF, the remaining precipitation of centrifugation, redissolve-precipitation-centrifugal process three times, vacuum-drying, obtain polymkeric substance/magnetic nanometer
Under the nitrogen protection condition, 1g polymkeric substance/magnetic nanometer is dissolved in the mixing solutions of THF, Virahol of 20mL, the anhydrous ethylenediamine that adds 10mL, magnetic agitation is 72 hours in 60 ℃, vacuum decompression revolves except that THF, centrifugation is auburn to sink to the bottom, and with removing ethanol and ionized water repetitive scrubbing on a small quantity, high-intensity magnetic field separation down obtains water miscible polymkeric substance magnetic nanometer;
D. water-soluble polymers/magnetic nanometer synthetic that has photoluminescent property: the amino terminal by fluorophor and polymkeric substance/magnetic nanometer surface reacts, and prepares the water-soluble polymers magnetic nanometer with photoluminescent property, and concrete steps are as follows:
Fluorescein is dissolved in the water, adds the above-mentioned magnetic nanometer that makes, the normal temperature magnetic agitation is 48 hours under the situation of logical nitrogen, and the high-intensity magnetic field separation obtains the final water-soluble polymers/magnetic nanometer with photoluminescent property.
Beneficial effect: the present invention is by steps such as employing high temperature organic phase co-electrodeposition methods, the synthesizing superfine magnetic nanometer, and utilize ATRP to be aggregated in the ethylene diamine-modified poly (glycidyl methacrylate) that its surface articulates biocompatibility, and on small part amino, introduce fluorophor, mark detecting signal.
This polymkeric substance/magnetic nanometer of synthetic has excellent biological compatibility and strong photoluminescent property.The macromolecule chain section that introduce on its surface is poly (glycidyl methacrylate) (PGMA), and PGMA has well water-soluble and biocompatibility.Introduce aminoly on the polymer ends, amino can be used to connect the biological functionality group that has the biomolecules of specific recognition with some, realizes the detection to specific biological molecules, in addition also further biological functional as connecing as certain drug etc.Introduce fluorophor, mark detecting signal.
Embodiment
In order to understand the present invention better, further specify technical scheme of the present invention below by specific embodiment.
Embodiment 1, Fe
3O
4Synthetic as the water-soluble polymers magnetic nanometer with photoluminescent property of magnetic nanometer nuclear
(1) magnetic nanometer is synthetic
Concrete steps are as follows:
With ferric acetyl acetonade (III) (1.766g, 0.337mL, 5mmol), 1; 2-16 glycol (6.461g, 25mmol), oleic acid (4.237g, 4.761mL; 15mmol), (4.012g, 4.935mL 15mmol) are dissolved in the 50mL dibenzyl ether oleyl amine; in the condition magnetic agitation that constantly feeds nitrogen; under nitrogen protection, mixing solutions is heated to 200 ℃ and continues 2 hours, be warmed up to 300 ℃ of following reheat one hour then, remove the thermal source cool to room temperature; add 100mL ethanol, have black precipitate to generate.Centrifugation is 10 minutes under 6000 rev/mins speed, centrifugation goes out black precipitate, and it is dispersed in the 40mL hexane solution that contains 1mL oleic acid and 1mL oleyl amine, centrifugation is 10 minutes under 6000 rev/mins speed, the black precipitate that centrifugation goes out is magnetic nanometer, with the magnetic nanometer drying under reduced pressure, preserve down at 0-4 ℃.
(2) introducing of initiator on the magnetic nanometer
Concrete steps are as follows:
The magnetic nanometer that 100mg oleic acid is stable is dispersed in the hexane solution of 3-chloropropionic acid of 0.25mol/L of 100mL; the normal temperature magnetic agitation is 24 hours under argon shield; centrifugation is 4 minutes under 6000 rev/mins the speed; centrifugation obtains introducing the magnetic nanometer of initiator; with three drying under reduced pressure of normal hexane washing, preserve down at 0-4 ℃.
(3) water miscible polymkeric substance/magnetic nanometer is synthetic
The magnetic nanometer of 60.0mg being introduced initiator is dissolved among the 3mL THF, obtains a transparent brown solution, logical nitrogen 15 minutes, add 5.1mg CuCl and 24mg dipyridyl, logical again argon gas 10 minutes, the mixing solutions sealing was stirred 18 hours at 30 ℃ of water-bath lower magnetic forces.With 1: 5 ratio tetrahydrofuran (THF) diluting reaction mixed solution, 4 minutes centrifugation gained of centrifugation mixed solution under 4000 rev/mins speed was removed the copper precipitation, and residual mixed liquor is splashed in the 200mL ether, obtains the Vandyke brown precipitation after reaction was finished.With resolution of precipitate in ethanol, 4 minutes remaining precipitations of centrifugation of centrifugation under 2000 rev/mins speed, redissolve-precipitation-centrifugal process three times, vacuum-drying obtains water miscible polymkeric substance/magnetic nanometer.
(4) water miscible polymkeric substance/fluorescence magnetic nanometer is synthetic
By fluorophor and amino reaction, the polymkeric substance/fluorescent nano particles of synthesizing water-solubility.
Concrete steps are as follows:
0.02 fluorescein is dissolved in the 10mL water, add the above-mentioned magnetic nanometer that makes of 20mg, the normal temperature magnetic agitation is 48 hours under the situation of logical nitrogen, the separating obtained magnetic nanometer of high-intensity magnetic field, washing with alcohol repeatedly finally obtains having the water-soluble polymers/magnetic nanometer of photoluminescent property.
Embodiment 2, CoFe
2O
4Synthetic as the water miscible fluorescence magnetic nanometer of magnetic nanometer nuclear
(1) magnetic nanometer is synthetic
Concrete steps are as follows:
With ferric acetyl acetonade (III) (1.413g; 4mmol), acetylacetone cobalt (II) (0.5503g; 2mmol), 1; 2-16 glycol (7.753g; 30mmol), oleic acid (5.084g; 5.713mL; 18mmol), (4.814g, 5.922mL 18mmol) are dissolved in the 60mL dibenzyl ether oleyl amine; in the condition magnetic agitation that constantly feeds nitrogen; under nitrogen protection, mixing solutions is heated to 200 ℃ and continues 2 hours, be warmed up to 300 ℃ of following reheat one hour then, remove the thermal source cool to room temperature; add 100mL ethanol, have black precipitate to generate.Centrifugation is 10 minutes under 6000 rev/mins speed, centrifugation goes out black precipitate, and it is dispersed in the 40mL hexane solution that contains 1mL oleic acid and 1mL oleyl amine, centrifugation is 10 minutes under 6000 rev/mins speed, the black precipitate that centrifugation goes out is magnetic nanometer, the magnetic nanometer drying under reduced pressure is preserved down at 0-4 ℃.
(2) introducing of initiator on the magnetic nanometer
Concrete steps are as follows:
The magnetic nanometer that 100mg oleic acid is stable is dispersed in the hexane solution of 3-chloropropionic acid of 0.25mol/L of 100mL; the normal temperature magnetic agitation is 24 hours under argon shield; centrifugation is 4 minutes under 6000 rev/mins the speed; centrifugation obtains introducing the magnetic nanometer of initiator; three drying under reduced pressure of normal hexane washing are preserved down at 0-4 ℃.
(3) water miscible polymkeric substance/magnetic nanometer is synthetic
The magnetic nanometer of 60.0mg being introduced initiator directly is dissolved in poly-(ethylene glycol) methacrylate monomer of 6mL, obtain a transparent brown solution, logical argon gas 15 minutes, NN N ' N ' the N that adds 10.2mg CuCl and 25 μ L " pentamethyl-diethylenetriamine; logical again nitrogen 10 minutes;, stirred 18 hours at 50 ℃ of water-bath lower magnetic forces with the mixing solutions sealing.With 1: 5 THF diluting reaction mixed solution, 4000 rev/mins of centrifugation gained mixed solutions were removed the cupric precipitation, and residual mixed liquor is splashed in the ethanol, obtain the Vandyke brown precipitation after reaction was finished.With resolution of precipitate in the THF of 10mL, the remaining precipitation of centrifugation, redissolve-precipitation-centrifugal process three times, vacuum-drying obtains the magnetic nanometer of polymkeric substance parcel.
(4) have water-soluble polymers/magnetic nanometer synthetic of photoluminescent property
By fluorophor and amino reaction, synthetic water-soluble polymers/magnetic nanometer with photoluminescent property.
Concrete steps are as follows:
0.02 fluorescein is dissolved in the 10mL water, add the above-mentioned magnetic nanometer that makes of 20mg, the normal temperature magnetic agitation is 48 hours under the situation of logical nitrogen, and the separating obtained magnetic nanometer of high-intensity magnetic field is finally had the water-soluble polymers/magnetic nanometer of photoluminescent property.
Claims (3)
1. one kind has epipolic water-soluble polymers magnetic nano-particle, it is characterized in that this nanoparticle has following structure: inner is the magnetic nano particle daughter nucleus,
Wherein,
Be MFe
2O
4Magnetic nanometer nuclear, wherein, metal M is a kind of among Fe, Co, the Mn, magnetic nanometer nuclear size homogeneous, FITC is a fluorophor,
M is the polymerization degree, and m is 30-100;
Macromolecular chain by on the end group-the COO-group is connected with the magnetic nanometer nuclear phase.
2. according to claim 1 have an epipolic water-soluble polymers magnetic nano-particle, it is characterized in that described magnetic nanometer nuclear has following three kinds of forms:
1) magnetic nanometer nuclear is Fe
3O
4, adhering to poly (glycidyl methacrylate) around the magnetic nanometer, polymer ends is introduced amino and a small amount of fluorescein of biocompatibility, and its structure is as follows:
2) magnetic nanometer nuclear is CoFe
2O
4, adhering to poly (glycidyl methacrylate) around the magnetic nanometer, polymer ends is introduced amino and a small amount of fluorescein of biocompatibility, and its structure is as follows:
3) magnetic nanometer nuclear is MnFe
2O
4, adhering to poly (glycidyl methacrylate) around the magnetic nanometer, polymer ends is introduced amino and a small amount of fluorescein of biocompatibility, and its structure is as follows:
3. preparation method with epipolic water-soluble polymers magnetic nano-particle as claimed in claim 1 is characterized in that concrete steps are as follows:
A. magnetic nanometer nuclear is synthetic: in the dibenzyl ether solvent, ferric acetyl acetonade is 1, and 2-16 glycol, oleic acid, oleyl amine pyrolytic decomposition prepare monodispersed magnetic nanometer, and concrete steps are as follows:
With ferric acetyl acetonade (III), 1,2-16 glycol, oleic acid, oleyl amine are dissolved in the dibenzyl ether,
Stir at the condition lower magnetic force that constantly feeds nitrogen, mixing solutions is heated to 200 ℃ continues 2 hours, be warmed up to 300 ℃ of following reheat one hour then, be cooled to room temperature, add small amount of ethanol, have black precipitate to generate.Centrifugation goes out black precipitate, then it is dispersed in the hexane solution that contains oleic acid and oleyl amine, and the dark solution that centrifugation goes out adds small amount of ethanol once more, and centrifugation goes out black precipitate and is magnetic nanometer.Drying under reduced pressure is at 0-4 ℃ of following cryopreservation;
B. initiator is introduced on magnetic nanometer nuclear surface: the surface that initiator 3-chloropropionic acid is introduced magnetic nanometer nuclear by metathesis, and concrete steps are as follows:
The magnetic nanometer that oleic acid is stable is dispersed in the hexane solution of 3-chloropropionic acid, under nitrogen protection, normal temperature magnetic agitation 24 hours, centrifugation obtains introducing the magnetic nanometer of initiator, wash repeatedly and drying under reduced pressure with normal hexane, at 0-4 ℃ of following cryopreservation;
C. water miscible polymkeric substance/magnetic nanometer is synthetic: on the magnetic nanometer that is connected to 3-chloropropionic acid initiator, by the synthetic poly (glycidyl methacrylate)/magnetic nanometer of active controllable free-radical method, concrete steps are as follows:
The magnetic nanometer of introducing initiator directly is dissolved in the tetrahydrofuran (THF) (THF), logical nitrogen 15 minutes adds CuCl and N N N ' N ' N, and " pentamethyl-diethylenetriamine, logical again nitrogen 10 minutes; with the mixing solutions sealing was 50 ℃ of water-bath lower magnetic forces stirrings 18 hours.After finishing, reaction uses THF diluting reaction mixed solution, centrifugation gained mixed solution, removal cupric precipitation splashes into residual mixed liquor in the ethanol, obtains the Vandyke brown precipitation, with resolution of precipitate in THF, the remaining precipitation of centrifugation, redissolve-precipitation-centrifugal process three times, vacuum-drying, obtain polymkeric substance/magnetic nanometer
Under the nitrogen protection condition, 1g polymkeric substance/magnetic nanometer is dissolved in the mixing solutions of THF, Virahol of 20mL, the anhydrous ethylenediamine that adds 10mL, magnetic agitation is 72 hours in 60 ℃, vacuum decompression revolves except that THF, centrifugation is auburn to sink to the bottom, and with removing ethanol and ionized water repetitive scrubbing on a small quantity, high-intensity magnetic field separation down obtains water miscible polymkeric substance/magnetic nanometer;
D. water-soluble polymers/magnetic nanometer synthetic that has photoluminescent property: the amino terminal by fluorophor and polymkeric substance/magnetic nanometer surface reacts, and prepares the water-soluble polymers/magnetic nanometer with photoluminescent property, and concrete steps are as follows:
Fluorescein is dissolved in the water, adds the above-mentioned magnetic nanometer that makes, the normal temperature magnetic agitation is 48 hours under the situation of logical nitrogen, and the high-intensity magnetic field separation obtains the final water-soluble polymers/magnetic nanometer with photoluminescent property.
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| CN110964145A (en) * | 2019-11-12 | 2020-04-07 | 中山大学 | Magnetic polymer microsphere based on acetylacetone group and preparation method thereof |
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