CN101579616B - Method for transforming magnetic nano-particles from oil phase to aqueous phase - Google Patents

Method for transforming magnetic nano-particles from oil phase to aqueous phase Download PDF

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CN101579616B
CN101579616B CN 200910023020 CN200910023020A CN101579616B CN 101579616 B CN101579616 B CN 101579616B CN 200910023020 CN200910023020 CN 200910023020 CN 200910023020 A CN200910023020 A CN 200910023020A CN 101579616 B CN101579616 B CN 101579616B
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magnetic nanoparticle
particles
magnetic nano
water
phase
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CN101579616A (en
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彭明丽
王苗
陈超
崔亚丽
李雅丽
张彩权
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Shaanxi Lifegen Co Ltd
Xi'an Goldmag Nanobiotech Co Ltd
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SHAANXI BEIMEI GENE CO Ltd
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
    • A61K49/18—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes
    • A61K49/1818—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles
    • A61K49/1821—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles
    • A61K49/1824—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles coated or functionalised nanoparticles
    • A61K49/1827—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles coated or functionalised nanoparticles having a (super)(para)magnetic core, being a solid MRI-active material, e.g. magnetite, or composed of a plurality of MRI-active, organic agents, e.g. Gd-chelates, or nuclei, e.g. Eu3+, encapsulated or entrapped in the core of the coated or functionalised nanoparticle
    • A61K49/1833—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles coated or functionalised nanoparticles having a (super)(para)magnetic core, being a solid MRI-active material, e.g. magnetite, or composed of a plurality of MRI-active, organic agents, e.g. Gd-chelates, or nuclei, e.g. Eu3+, encapsulated or entrapped in the core of the coated or functionalised nanoparticle having a (super)(para)magnetic core coated or functionalised with a small organic molecule
    • A61K49/1839—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles coated or functionalised nanoparticles having a (super)(para)magnetic core, being a solid MRI-active material, e.g. magnetite, or composed of a plurality of MRI-active, organic agents, e.g. Gd-chelates, or nuclei, e.g. Eu3+, encapsulated or entrapped in the core of the coated or functionalised nanoparticle having a (super)(para)magnetic core coated or functionalised with a small organic molecule the small organic molecule being a lipid, a fatty acid having 8 or more carbon atoms in the main chain, or a phospholipid
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y25/00—Nanomagnetism, e.g. magnetoimpedance, anisotropic magnetoresistance, giant magnetoresistance or tunneling magnetoresistance
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01F—MAGNETS; INDUCTANCES; TRANSFORMERS; SELECTION OF MATERIALS FOR THEIR MAGNETIC PROPERTIES
    • H01F1/00—Magnets or magnetic bodies characterised by the magnetic materials therefor; Selection of materials for their magnetic properties
    • H01F1/0036—Magnets or magnetic bodies characterised by the magnetic materials therefor; Selection of materials for their magnetic properties showing low dimensional magnetism, i.e. spin rearrangements due to a restriction of dimensions, e.g. showing giant magnetoresistivity
    • H01F1/0045—Zero dimensional, e.g. nanoparticles, soft nanoparticles for medical/biological use
    • H01F1/0054—Coated nanoparticles, e.g. nanoparticles coated with organic surfactant
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01F—MAGNETS; INDUCTANCES; TRANSFORMERS; SELECTION OF MATERIALS FOR THEIR MAGNETIC PROPERTIES
    • H01F1/00—Magnets or magnetic bodies characterised by the magnetic materials therefor; Selection of materials for their magnetic properties
    • H01F1/44—Magnets or magnetic bodies characterised by the magnetic materials therefor; Selection of materials for their magnetic properties of magnetic liquids, e.g. ferrofluids

Abstract

The invention relates to a method for transferring magnetic nano-particles from an oil phase to an aqueous phase. The method comprises the steps of adding an oxidant to an oil-phase magnetic nano-particle solution, oxidizing unsaturated carbon-carbon double bonds in an oleic-acid long chain on the surfaces of oil-phase magnetic nano-particles into hydrophilic carboxyl groups through reaction, and transforming the oil-phase dispersed magnetic nano-particles into aqueous-phase dispersed magnetic nano-particles. The method is simple in process, convenient and fast to operate, effectively reduces the cost for cleaning the oil-phase magnetic nano-particles, realizes the surface carboxyl functional modification of the magnetic nano-particles, and ensures that introduced carboxyl functional groups can be connected to proteins, nucleic acids, medicaments and the like, thereby enabling the magnetic nano-particles to be applied in the field of biological medicines better.

Description

The method that a kind of oil phase magnetic nanoparticle shifts to water
Technical field
The present invention relates to preparation, structure, performance and the application study field thereof of inorganic compounding functional material, the magnetic nanoparticle that is specifically related to a kind of oil phase dispersion is converted into the method for the magnetic nanoparticle of water dispersion.
Background technology
Magnetic Nano material is a kind of new material that development in recent years is got up; It had both had the character of nano material, also had special magnetic property, thereby can be widely used in biological and medical field; Like magnetic resonance imaging (MRI); Separating of cell and albumen, drug targeting, the diagnosis of cancer and treatment etc.
At present, in the chemical synthesis process of magnetic nanoparticle, the magnetic nanoparticle of high-temperature decomposition preparation is like employing pyrolytic iron oleate compound, Alivisatos group thermal decomposition Fe (CO) such as Hyeon 5, pyrolytic Fe (acac) such as Sun 3The ferric oxide nano particles that makes has monodispersity, narrow diameter distribution, advantage such as magnetic responsiveness is good, and lattice defect is few, and size and pattern are controlled.Yet; The ferric oxide nano particles that these methods obtain is being coated by oleic acid; Since water insoluble and limited its application greatly at biomedical sector, how the oil-soluble magnetic nanoparticle is converted into water miscible magnetic nanoparticle and has obtained paying close attention to widely.
(α-CD) modifies the oil phase magnetic nanoparticle like human alpha-cyclodextrins such as Yang; Make the hydrophobic cavity of the oleic acid long-chain entering α-CD on magnetic grain surface, draw in aqueous phase [Nano Letters, 2003 to magnetic nanoparticle through the hydrophilic radical of α-CD exocoel; 3,1555]; Human amphiphilic macromolecule Pluronic F-127 such as Qin coat the oil phase magnetic nanoparticle; Pluronic F-127 is embedded in the oil phase long-chain on magnetic nanoparticle surface; Utilize the hydrophily of chain end hydroxyl to realize phase transfer [Adv.Mater.2007,19,1874]; People such as Lee modify the 3-mercaptopropionic acid on the oil phase magnetic nanoparticle, change the magnetic grain over to aqueous phase [IEEE TransNanotech.2008,7; 111]; Also some people utilizes surfactant to make system be emulsion, and the organic solvent that volatilizees then makes magnetic nanoparticle get into aqueous phase [Nano Lett.2005; 5,645].Magnetic nanoparticle after above method water shifts is not all introduced activity functional groups, also needs further rhetorical function group to use.
Summary of the invention
In order to solve the problems of the technologies described above; The invention provides a kind of method that realizes the transfer of oil phase magnetic nanoparticle water through oxidation reaction; This method can be carried out water with the oil phase magnetic nanoparticle quickly and shifted; The carboxyl function group of introducing simultaneously can also connect albumen, nucleic acid, medicine etc., with magnetic nanoparticle better be applied to biomedicine field.
The technical scheme that the present invention addresses the above problem:
Scheme one
The oil phase magnetic nanoparticle may further comprise the steps to the method that water shifts:
The magnetic nanoparticle that (1) will be coated with oleic acid is dispersed in organic mixed solvent, obtains the magnetic fluid that solid contents is 0.5～50mg/ml;
(2) adding concentration is the aqueous oxidizing agent solution of 0.01～0.5mol/L, stirring reaction 0.5～24h; The mass ratio of this oxidant and magnetic nanoparticle is 1～5: 1;
(3) with externally-applied magnetic field magnetic nanoparticle is separated from solution, abandoned supernatant, water cleans magnetic nanoparticle, is dispersed in the water.
Organic mixed solvent in the above-mentioned steps (1) is nonpolar and mixture polar organic solvent; Non-polar organic solvent can be n-hexane, toluene, chloroform or cyclohexane, and polar organic solvent can be in oxolane, ethyl acetate or the acetonitrile one or more, and the volume ratio of this non-polar organic solvent and polar organic solvent is 1: 0.5～10.
Oxidant can be O in the above-mentioned steps (2) 3, KMnO 4, H 2O 2, OsO 4, K 2Cr 2O 7, CrO 3, NaIO 4Or NaClO.
Above-mentioned steps also can add catalyst in (2), and the mass ratio of catalyst and magnetic nanoparticle is 0.001～0.04: 1, and this catalyst can be V 2O 5, PtCl 2Or RuCl 3
Scheme two
The oil phase magnetic nanoparticle may further comprise the steps to the method that water shifts:
The magnetic nanoparticle that (1) will be coated with oleic acid is dispersed in the microemulsion system, obtains the magnetic fluid that solid contents is 0.5～50mg/ml;
(2) adding concentration is the aqueous oxidizing agent solution of 0.01～0.5mol/L, stirring reaction 0.5～24h; The mass ratio of this oxidant and magnetic nanoparticle is 1～5: 1;
(3) with externally-applied magnetic field magnetic nanoparticle is separated from solution, abandoned supernatant, water cleans magnetic nanoparticle, is dispersed in the water.
Contain organic solvent, water and surfactant in the microemulsion system of above-mentioned steps (1); Surfactant can be softex kw, polyoxyethylene alcohol, Tween 20 or neopelex, and the concentration of surfactant in microemulsion is 0.7～200mmol/L.
Oxidant can be O in the above-mentioned steps (2) 3, KMnO 4, H 2O 2, OsO 4, K 2Cr 2O 7, CrO 3, NaIO 4Or NaClO.
Above-mentioned steps also can add catalyst in (2), and the mass ratio of catalyst and magnetic nanoparticle is 0.001～0.04: 1, and this catalyst can be V 2O 5, PtCl 2Or RuCl 3
Advantage of the present invention:
The present invention is through oxidation reaction, and a step has been realized the phase transfer of magnetic nanoparticle and two purposes of carboxyl-functional modification on surface; This method technology is simple, simple and efficient to handle; Reduced cleaning charge usefulness effectively, and can further connect albumen, nucleic acid, medicine etc., thereby magnetic nanoparticle has been applied to biomedicine field better through carboxylic group to the oil phase magnetic nanoparticle.
Description of drawings
Fig. 1 is the reaction principle sketch map of this method.
Fig. 2 is magnetic nanoparticle oil phase/water scatter diagram before and after the reaction; Wherein A is a magnetic nanoparticle oil phase scatter diagram before the reaction, and B is a reaction back magnetic nanoparticle water scatter diagram; 1 and 3 is n-hexanes, and 2 and 4 is ultra-pure waters.
Fig. 3 is the Fe that disperses in the n-hexane 3O 4The TEM figure of magnetic nanoparticle.
Fig. 4 is the Fe after water shifts 3O 4The TEM figure of magnetic nanoparticle.
The specific embodiment
As shown in Figure 1, reaction principle of the present invention is: be oxidized to the carboxyl of possess hydrophilic property to the unsaturated carbon-carbon double bond in the oleic acid long-chain on oil phase magnetic nanoparticle surface, the magnetic nanoparticle that oil phase is disperseed is converted into the magnetic nanoparticle that water disperses.
Its specific embodiment is following:
Embodiment 1:
With Fe 3O 4Magnetic nanoparticle is dispersed in the n-hexane, obtains the Fe that solid contents is 20mg/ml 3O 4The hexane solution of magnetic nanoparticle is got this solution 2ml, adds 2ml ethyl acetate and 2ml acetonitrile, stirs this organic mixed solution is mixed, again with 124mg NaIO 4With 0.8mg RuCl 3Be dissolved in the 3ml water, be added drop-wise in above-mentioned organic mixed solution, stirring reaction 2h, reaction utilizes externally-applied magnetic field with Fe after finishing 3O 4Magnetic nanoparticle is separated from solution, supernatant discarded solution, Fe 3O 4Magnetic nanoparticle cleans 3 times with ultra-pure water, is dispersed in the ultra-pure water, promptly obtains the Fe that water disperses 3O 4Magnetic nanoparticle.Magnetic nanoparticle oil phase dispersity such as Fig. 2 (A) and shown in Figure 3 before the reaction, wherein 1 is n-hexane, the 2nd, ultra-pure water can be seen Fe 3O 4Magnetic nanoparticle is dispersed in the n-hexane, reaction back magnetic nanoparticle water dispersity such as Fig. 2 (B) and shown in Figure 4, and wherein 3 is n-hexanes, the 4th, ultra-pure water can be seen Fe 3O 4Magnetic nanoparticle has been distributed in the ultra-pure water.
Embodiment 2:
With Fe 3O 4Magnetic nanoparticle is dispersed in the n-hexane, obtains the Fe that solid contents is 20mg/ml 3O 4The hexane solution of magnetic nanoparticle; Get this solution 2ml, add 10ml ultra-pure water and 30mg softex kw (CTAB), ultrasonic agitation 20min makes the formation microemulsion; Add 0.057mlNaClO solution (Cl>=8%); Stirring reaction 50min, regulator solution pH value=12.5 add 0.285ml NaClO solution and 0.8mg RuCl more then 3, continuing stirring reaction 1h, reaction utilizes externally-applied magnetic field with Fe after finishing 3O 4Magnetic nanoparticle is separated from solution, supernatant discarded solution, Fe 3O 4Magnetic nanoparticle cleans 3 times with ultra-pure water, is dispersed in the ultra-pure water, promptly obtains the Fe that water disperses 3O 4Magnetic nanoparticle.Magnetic nanoparticle oil phase dispersity such as Fig. 2 (A) and shown in Figure 3 before the reaction, wherein 1 is n-hexane, the 2nd, ultra-pure water can be seen Fe 3O 4Magnetic nanoparticle is dispersed in the n-hexane, reaction back magnetic nanoparticle water dispersity such as Fig. 2 (B) and shown in Figure 4, and wherein 3 is n-hexanes, the 4th, ultra-pure water can be seen Fe 3O 4Magnetic nanoparticle has been distributed in the ultra-pure water.
Embodiment 3:
With Fe 3O 4Magnetic nanoparticle is dispersed in the n-hexane, obtains the Fe that solid contents is 20mg/ml 3O 4The hexane solution of magnetic nanoparticle is got this solution 2ml, adds the 6ml oxolane, 124mgNaIO 4With 0.8mg RuCl 3Be dissolved in the 3ml water, be added drop-wise in the above-mentioned organic solution, stirring reaction 3h, reaction utilizes externally-applied magnetic field with Fe after finishing 3O 4Magnetic nanoparticle is separated from solution, supernatant discarded solution, Fe 3O 4Magnetic nanoparticle cleans 3 times with ultra-pure water, is dispersed in the ultra-pure water, promptly obtains the Fe that water disperses 3O 4Magnetic nanoparticle.Magnetic nanoparticle oil phase dispersity such as Fig. 2 (A) and shown in Figure 3 before the reaction, wherein 1 is n-hexane, the 2nd, ultra-pure water can be seen Fe 3O 4Magnetic nanoparticle is dispersed in the n-hexane, reaction back magnetic nanoparticle water dispersity such as Fig. 2 (B) and shown in Figure 4, and wherein 3 is n-hexanes, the 4th, ultra-pure water can be seen Fe 3O 4Magnetic nanoparticle has been distributed in the ultra-pure water.

Claims (3)

1. an oil phase magnetic nanoparticle is characterized in that to the method that water shifts, and may further comprise the steps:
The magnetic nanoparticle that (1) will be coated with oleic acid is dispersed in organic mixed solvent system, obtains the magnetic fluid that solid contents is 0.5～50mg/ml;
Described organic mixed solvent is nonpolar and mixture polar organic solvent; Wherein, non-polar organic solvent is n-hexane, toluene, chloroform or cyclohexane, and polar organic solvent is one or more in oxolane, ethyl acetate or the acetonitrile, and the volume ratio of non-polar organic solvent and polar organic solvent is 1: 0.5～10;
(2) adding concentration is the aqueous oxidizing agent solution of 0.01～0.5mol/L, stirring reaction 0.5～24h; The mass ratio of said oxidant and magnetic nanoparticle is 1～5: 1;
(3) with externally-applied magnetic field magnetic nanoparticle is separated from solution, abandoned supernatant, water cleans magnetic nanoparticle, is dispersed in the water.
2. oil phase magnetic nanoparticle according to claim 1 is characterized in that to the method that water shifts: oxidant is O in the said step (2) 3, KMnO 4, H 2O 2, OsO 4, K 2Cr 2O 7, CrO 3, NaIO 4Or NaClO.
3. the method that oil phase magnetic nanoparticle according to claim 2 shifts to water, it is characterized in that: said step also adds catalyst in (2), and the mass ratio of catalyst and magnetic nanoparticle is 0.001～0.04: 1, and said catalyst is V 2O 5, PtCl 2Or RuCl 3
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CN102436885A (en) * 2011-09-08 2012-05-02 西北大学 Method for dispersing iron-based magnetic nanocrystals
CN105931794B (en) * 2016-06-28 2017-11-14 马鞍山福来伊环保科技有限公司 A kind of recovery and treatment method of application and magnetic flow liquid of the inorganic agent in magnetic flow liquid recycling field
CN105931793B (en) * 2016-06-28 2018-05-11 马鞍山福来伊环保科技有限公司 The magnetic flow liquid recovery and treatment method that a kind of oleic acid is modified
CN105906130B (en) * 2016-06-28 2019-01-11 马鞍山福来伊环保科技有限公司 A kind of the recovery processing agent and its application method of the magnetorheological fluid that oleic acid is modified
CN106098288B (en) * 2016-06-28 2018-06-08 马鞍山福来伊环保科技有限公司 A kind of magnetorheological fluid recovery processing agent and preparation method thereof
CN107474828A (en) * 2017-07-21 2017-12-15 闽南师范大学 A kind of water-solubleization method of oil-soluble sulphur based semiconductor quantum dot
CN109207142A (en) * 2018-10-31 2019-01-15 牡丹江医学院 A kind of preparation method that hydrophobic nano particle is changed into hydrophilic nanoparticles
CN113230418A (en) * 2021-05-12 2021-08-10 中国药科大学 Preparation method and application of iron nanoparticles with ultra-small core-shell structure

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