CN104064305B - A kind of method for preparing water-soluble magnetic nanoparticle - Google Patents
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Abstract
The present invention provides a kind of method for preparing water-soluble magnetic nanoparticle.The present invention, is reacted by simple displacement, you can prepare water miscible magnetic nano-particle as part displacer molecule from polyglycol diacid.Using the water-soluble magnetic nanoparticle prepared by the method for the present invention, both the advantages of having remained good dispersion, the superparamagnetism of oil-soluble nano particles, water solublity is provided with again, simultaneously also introduce in nanoparticle surface that fix bridge in nanoparticle surface as biomolecule is function base carboxyl, meet the requirement of biochemical reaction.The water-soluble magnetic nanoparticle is had a wide range of applications in biomedicine fields such as NMR (Nuclear Magnetic Resonance) imaging, targeted drug, immobilized enzyme.
Description
Technical field
The present invention relates to nano material and nanoparticle surface chemical modification, and in particular to one kind prepares water-soluble magnetic and receives
The method of rice corpuscles and the water-soluble magnetic nanoparticle according to prepared by the method and application thereof.
Background technology
Magnetic Fe3O4Nanoparticle has special superparamagnetism, in giant magnetoresistance, magnetic liquid and magnetic recording, mangneto
The aspects such as cold, magnetic detector are with a wide range of applications.Meanwhile, Fe3O4Nanoparticle also has important answering in biomedical sector
With, can apply to protein purification, separate nucleic acid and purification, immune analysis determination, Magnetic Fluid Hyperthermia technology, targeted drug,
The aspects such as immobilized enzyme.Therefore, now concerning Fe3O4The research of magnetic nano-particle is a popular domain.Prepare Fe3O4Magnetic
Property nanoparticle method it is a lot, have coprecipitation, microemulsion method, thermal decomposition method, biological auxiliary synthetic method etc., wherein with high temperature
The particle size topography uniformity of thermal decomposition method synthesis is best.In addition, Oleic acid is usually used（Referred to as OA）Deng as surface work
Property agent is controlling the size or shape of nanoparticle.
In order to extend application of the magnetic nano-particle in biological field, it is necessary to carry out surface to magnetic nano-particle and repair
Decorations, to improve its surface property.Firstly, since the requirement of biochemical reaction, needs to change oil-soluble Fe3O4Magnetic nano-particle
Dispersibility so as to can be scattered in water solution system；Secondly, need in Fe while surface modification3O4Magnetic nano-particle
Surface introduces functional group（- COOH ,-SH- ,-NH2）So as to as the bridge that biomolecule is fixed in nanoparticle surface.Table
What the method for face chemical modification was mainly realized by the chemical reaction between modifying agent and nanoparticle surface, including esterification
Method, modification by coupling, surface graft modification method, part displacement method etc.；Wherein, part displacement method is a kind of more common surface modification
Method, it is main to replace the original oil-soluble molecule in surface by adding excessive additional water soluble molecules, reach the mesh of phase transfer
's.At present, have been reported in Au, FePt, γ-Fe2O3、Fe3O4Nanoparticle surface realizes phase transfer by part displacement；
Used by which, modifying agent is also varied, is such as replaced by water miscible organic molecule, organic macromolecule, polymer molecule
Fe3O4The oil-soluble oleic acid molecular of nanoparticle surface, obtains different aqueous solution systems, can be applicable to optical probe, magnetic point
From fields such as, immobilized enzyme.
Recently, Sun etc. reports a kind of new method, the Fe to oleic acid modified3O4Magnetic nano-particle carries out surface and is modified.
They adopt the Polyethylene Glycol of dual-functional group（Polyethylene Glycol with 2 carboxyls is PEG-diacid）With biological micromolecule dopamine
Condensation reaction is carried out, generating a headband has carboxyl, and other end is the ligand molecular of dopamine, by monolayer exchange reaction,
Part displacement has been carried out to the system of oleic acid modified, Fe has been obtained3O4The water-soluble system of-DPA-PEG-COOH（“Controlled
PEGylation of Monodisperse Fe3O4Nanoparticles for Reduced Non-Specific Uptake
By Macrophage Cells ", Jin Xie et al., Advanced Materials, 19 phases, 3163-3166 page, 2007
Year）.In this system, due to DPA（Dopamine）It is condensed the part to be formed to have very with the Polyethylene Glycol of two carboxyls of band
Good biocompatibility, has very big application prospect in terms of biology, but, the method is relatively complicated, gained particle surface
Structure is extremely complex, and this increased difficulty to follow-up biologic applications, therefore to be more preferably adapted to the water of biological applications
Dissolubility magnetic Fe3O4Nanoparticle, there is a need to and current existing method is further improved.
The content of the invention
Therefore, it is an object of the present invention to provide a kind of method for preparing water-soluble magnetic nanoparticle.
It is a further object of the invention to provide the water-soluble magnetic nanoparticle and its use prepared by said method
On the way.
The purpose of the present invention employs the following technical solutions to realize.On the one hand, the invention provides one kind prepares water
The method of dissolubility magnetic nano-particle, which selects polyglycol diacid as part, by part method of replacing by magnetic Nano
Particle is transferred to water phase from oil phase.
Preferably, described magnetic nano-particle is selected from Fe3O4, γ-Fe2O3Or FeO, preferably Fe3O4。
Preferably, described method comprises the following steps：（1）Prepare mixed solution：By polyglycol diacid, chloralkane
Mix with DMF, obtain mixed solution；Wherein described chloralkane and the N,N-dimethylformamide
Volume ratio is 1～3:1, preferably 2:1, the polyglycol diacid is 0.01～0.03 with the volume ratio of the chloralkane:
1, preferably 0.02:1, the chloralkane is selected from dichloromethane, chloroform or trichloroethane, preferably chloroform；（2）
Prepare water-soluble magnetic nanoparticle：According to 1.1mg/ml～2.1mg/ml, preferably the concentration of 1.6mg/ml is to above-mentioned mixing
Magnetic nano-particle is added in solution, under inert gas atmosphere, preferably N2Concussion reaction under atmosphere, obtains water-soluble magnetic
Nanoparticle.
It is highly preferred that described method may particularly include following steps：（1）Prepare mixed solution：By 200 μ L Polyethylene Glycol
Diacid is dissolved in 10mL chloroform and 5mL DMF mixed solutions, is stirred 30 minutes, obtains mixing molten
Liquid；（2）Prepare water-soluble magnetic nanoparticle：The oil-soluble Fe of 25mg are added in above-mentioned mixed solution3O4Nanoparticle, example
The Fe of Oleic acid is coated with such as3O4Nanoparticle, in N2The lower concussion reaction of protection 24 hours, Magnet separates and collects sample, dehydrated alcohol
Washing 3 times, is dried, obtains water solublity Fe3O4Nanoparticle.
On the other hand, the invention provides the water-soluble magnetic nanoparticle of said method preparation, its surface is with biology
Functional group carboxyl.
Preferably, a diameter of 10～30nm of described water-soluble magnetic nanoparticle.
Present invention also offers purposes of the described water-soluble magnetic nanoparticle in biomedical sector.
Preferably, described biomedical sector include protein purification, separate nucleic acid and purification, immune analysis determination,
Magnetic Fluid Hyperthermia technology, targeted drug, optical probe, Magneto separate and immobilized enzyme etc..
Another aspect, the invention provides purposes of the polyglycol diacid in water-soluble magnetic nanoparticle is prepared；It is excellent
Selection of land, the polyglycol diacid is in water-soluble magnetic nanoparticle is prepared as part.
Preferably, wherein the mean molecule quantity of described polyglycol diacid is 400～2000, preferably 600.
As can be seen here, the present invention utilizes simple part method of replacing by oil-soluble Fe3O4Nanoparticle is transferred to water
Phase, prepared water solublity Fe3O4Nanoparticle is not only distributed homogeneous, quality height in water phase, also meets two of biochemical reaction
Require：First, magnetic nano-particle can be scattered in water solution system；Secondly, again in Fe while surface modification3O4Magnetic
Property nanoparticle surface introduce functional group（Such as-COOH) etc..Described oil-soluble Fe3O4Diameter of nano particles is 5～
20nm, and surface capping agents are Oleic acid.Described part is polyglycol diacid, and the functional group that surface introduces is carboxyl.
In sum, the present invention utilizes simple part method of replacing, using the Polyethylene Glycol two with bifunctional group
Sour (HOOC-PEG-COOH is abbreviated as PEG-diacid) modifies Fe directly as part3O4Nanoparticle, is simply reacting
By monolayer exchange reaction under system, direct replacement Fe3O4Oleic acid ligand in nanoparticle, obtains aqueous solution systems, body
Hydrophilic group in system is carboxyl, and part is the Polyethylene Glycol of good two carboxyls of band of biocompatibility, after these features are all
The research that continuous biological enzyme molecule is fixed is laid a good foundation.
Relative to existing Fe3O4The water-soluble system of-DPA-PEG-COOH, the method for the present invention are more simple, by a step
The displacement of method part is obtained the Fe of water-solubility function3O4Nano-particle, and avoid the surface texture caused due to DPA
The big defect of complicated, biological utilisation difficulty.Additionally, the transmission electron microscope photo before and after being replaced by part can find its tool
There is the dispersibility of height.
The water solublity Fe prepared using the method for the present invention3O4Nanoparticle, had both remained oil-soluble nano particles
High-quality, such as good dispersion, superparamagnetism etc., are provided with water solublity again, while also introducing function base in nanoparticle surface.
The bridge that the function base can be fixed in nanoparticle surface as biomolecule, meets the requirement of biochemical reaction, nuclear-magnetism into
The biomedicine fields such as picture, targeted drug, immobilized enzyme all have a wide range of applications.
Description of the drawings
Hereinafter, with reference to accompanying drawing describing embodiments of the invention in detail, wherein：
Fig. 1 a are Fe before part of the present invention displacement3O4The transmission electron microscope picture of nanoparticle；
Fig. 1 b are Fe after part of the present invention displacement3O4The transmission electron microscope picture of nanoparticle；
Fig. 2 is that part of the present invention replaces Fe after the displacement of front and part3O4The M-H magnetization curve figures of nanoparticle.
Specific embodiment
The present invention is expanded on further below in conjunction with preferred embodiment, but these embodiments are only limitted to the explanation present invention, not
The scope of the present invention can be limited.
Embodiment 1The method for preparing water-soluble magnetic nanoparticle
The present embodiment is the method for preparing water-soluble magnetic nanoparticle provided by the present invention, and which comprises the following steps：
The first step：By 200 μ L polyglycol diacids（Purchased from Sigma-Aldrich companies, molecular weight is 600）.It is dissolved in
In 10mL chloroform and 5mL DMF mixed solutions, stir 30 minutes, obtain mixed solution.
Second step：Synthesis good dispersion, high-quality oil-soluble Fe3O4Nanoparticle：With Fe (acac)3For presoma, lead to
Cross high temperature oil phase pyrolysismethod and prepare Fe3O4Nanoparticle（Refer to document：Sun S.H.,Zeng H.,Rob in son D.B.,
e t al..J.Am.Chem.Soc.[J],2004,126(1):273-279）, under argon protection, by 0.17604g Fe
(acac)3And 215825g1,2- hexadecane diol is dissolved in 20mL benzyl ethers, 119mL Oleic acid and 2mL oleyl amines, stirring are added
And 200 DEG C are heated to, temperature is promoted to 300 DEG C and constant temperature 1h by constant temperature 2h, is stopped heating, is made reactant liquor naturally cold under stirring
But to room temperature, dark solution is obtained, adds 40mL dehydrated alcohol, centrifugation, vacuum drying, product to treat in being stored in normal hexane
With.
3rd step：The oil-soluble Fe of 25mg are added in mixed solution in the above-mentioned first step3O4Nanoparticle, in N2Protect
The lower concussion reaction of shield 24 hours, Magnet separates and collects sample, and absolute ethanol washing 3 times is dried, obtains water solublity and function of surface
Fe of the group for carboxyl3O4Nanoparticle.
Embodiment 2The structural characterization of water-soluble magnetic nanoparticle
The present embodiment is the structural characterization of the water-soluble magnetic nanoparticle according to prepared by the method for embodiment 1.
Fe before part displacement3O4The transmission electron microscope picture of nanoparticle as shown in Figure 1a, part displacement after Fe3O4Nanoparticle
Transmission electron microscope picture as shown in Figure 1 b.Wherein, Fig. 1 a are oil-soluble Fe3O4Nanoparticle is dissolved in normal hexane（That is embodiment 1
The particle that second step is obtained）, concentration is 1.6mg/ml, and Fig. 1 b are water miscible Fe3O4Nanoparticle is soluble in water, and concentration is also
1.6mg/ml。
Instrument title：200KV lanthanum hexaboride transmission electron microscopes, INSTRUMENT MODEL：Tecnai G220S-TWIN, producer：
FEI Co. of the U.S., voltage：200KV.
It is seen that before and after part displacement, there is no significant change, explanation in the particle diameter and pattern of nano-particle
The method of the present invention does not affect oil-soluble Fe3O4Premium properties of the nanoparticle sheet in terms of the such as shape and particle diameter.It is simultaneously logical
Cross contrast can be seen that, the water solublity Fe obtained by the present invention3O4Nanoparticle under same concentrations shows to be substantially better than crude oil
The dispersive property of dissolubility nanoparticle, so as to obtain more preferably technique effect.
Part replaces Fe after the displacement of front and part3O4The M-H magnetization curves of nanoparticle are as shown in Fig. 2 wherein curve a is
Fe before part displacement3O4Nanoparticle（Fe3O4- OA is represented by the Fe of oleic acid modified3O4）M-H magnetization curves, curve b be part
Fe after displacement3O4Nanoparticle（Fe3O4- PEG diacid represent the Fe modified by polyglycol diacid3O4）M-H magnetic it is bent
Line.
Instrument title：Analysis of Physical instrument（PPMS）, INSTRUMENT MODEL：PPMS-9, company-information：U.S. Quantum
Design Inc.（Quantum Design, Inc. of the U.S.）, experiment condition：H scopes are ± 15000Oe, and temperature is 298K.
The figure is obtained Fe3O4The value of the saturation magnetization of nanoparticle, answering for aspects such as later stage Magneto separates
With.Can be seen that from the figure, the water solublity Fe after part displacement3O4Nanoparticle still maintains the super suitable of former oil-soluble nano particles
Magnetic.
Claims (8)
1. a kind of method for preparing water-soluble magnetic nanoparticle, it is characterised in that the method uses polyglycol diacid conduct
Magnetic nano-particle is transferred to water phase from oil phase by part method of replacing, obtains water-soluble magnetic nanoparticle by part；Its
In, the method comprises the following steps：
(1) prepare mixed solution：Polyglycol diacid, chloralkane and DMF are mixed, mixing is obtained molten
Liquid；Wherein described chloralkane is 1～3 with the volume ratio of the N,N-dimethylformamide:1, the polyglycol diacid with
The volume ratio of the chloralkane is 0.01～0.03:1, the chloralkane is selected from dichloromethane, chloroform or three chloroethenes
Alkane；
(2) prepare water-soluble magnetic nanoparticle：Add in above-mentioned mixed solution according to the concentration of 1.1mg/ml～2.1mg/ml
Enter magnetic nano-particle, under inert gas atmosphere concussion reaction, obtain water-soluble magnetic nanoparticle；
Wherein described magnetic nano-particle is selected from Fe3O4, γ-Fe2O3Or FeO.
2. method according to claim 1, it is characterised in that the magnetic nano-particle is Fe3O4。
3. method according to claim 1 and 2, it is characterised in that in step (1), the chloralkane and the N,
The volume ratio of dinethylformamide is 2:1.
4. method according to claim 1 and 2, it is characterised in that in step (1), polyglycol diacid and the chlorine
It is 0.02 for the volume ratio of alkane:1.
5. method according to claim 1 and 2, it is characterised in that in step (1), the chloralkane are three chloromethanes
Alkane.
6. method according to claim 1 and 2, it is characterised in that in step (2), according to 1.6mg/ml concentration to
Magnetic nano-particle is added in above-mentioned mixed solution.
7. method according to claim 1 and 2, it is characterised in that in step (2), in N2Concussion reaction under atmosphere, obtains
To water-soluble magnetic nanoparticle.
8. a kind of method for preparing water-soluble magnetic nanoparticle, it is characterised in that the method is comprised the following steps：
(1) prepare mixed solution：200 μ L polyglycol diacids are dissolved in into 10mL chloroform and 5mL N, N- dimethyl formyl
In amine mixed solution, stir 30 minutes, obtain mixed solution；
(2) prepare water-soluble magnetic nanoparticle：The oil-soluble Fe of 25mg are added in above-mentioned mixed solution3O4Nanoparticle,
N2The lower concussion reaction of protection 24 hours, Magnet separate and collect sample, and absolute ethanol washing 3 times is simultaneously dried, and obtains water solublity Fe3O4
Nanoparticle.
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| CN102815753A (en) * | 2012-08-24 | 2012-12-12 | 上海交通大学 | Fe3O4 nano-particles with high dispersion stability in water phase, and preparation method thereof |
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| CN102557149B (en) * | 2010-12-16 | 2014-01-15 | 国家纳米科学中心 | Method for preparing water-soluble nanometer iron oxide |
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