CN104721844A - Novel CT (Computerized Tomography), MRI (Magnetic Resonance Imaging) and rare-earth fluorescence three-function microspheres as well as preparation method and application thereof - Google Patents
Novel CT (Computerized Tomography), MRI (Magnetic Resonance Imaging) and rare-earth fluorescence three-function microspheres as well as preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses novel CT (Computerized Tomography), MRI (Magnetic Resonance Imaging) and rare-earth fluorescence three-function microspheres as well as a preparation method and an application thereof. The shells of the three-function microspheres are made from styrene and a complex which has the dual functions of CT and fluorescence and contains rare-earth europium (III), the cores of the three-function microspheres are made from Fe3O4 nano particles, and the three-function microspheres are prepared by a two-step seed emulsifier-free emulsion polymerization method. The Fe3O4 nano particles wrapped in the microspheres endow the microspheres with an MRI function; and the complex in the shells of the microspheres endows the microspheres with a CT function and a fluorescence function. The microspheres have uniform particle sizes, simple synthesis conditions, favorable biocompatibility and good MRI and CT effects, belong to the crossing field of materials and biological medicine and have potential application values.
Description
Technical field
The present invention relates to material science and biomedicine technical field, particularly relate to a kind of new CT, MRI, rare-earth fluorescent three functional microsphere and its preparation method and application.
Background technology
The research of composite nano-microsphere has a long history, and is the study hotspot in field to the functional exploitation of Material cladding always.Nowadays, material is environmental response such as, Separation of Proteins, Gene segregation, purification of water quality, target drug-carrying, and medicament slow release is treated, and the several functions such as fluorescent probe have had tremendous development in commercial production and biomedicine field.
At biomedicine field, nano composite material has very large potential using value.Many image-forming diagnoses are as fluorescence imaging, CT scan (CT), positron e mission computed tomography (PET) and nuclear magnetic resonance (MRI) etc. often all need to add nano composite material with Enhanced Imaging effect.Wherein MRI is the real-time detection means of a kind of conventional hurtless measure, high spatial resolution.Different according to relaxation direction (laterally with longitudinal direction), its contrast agent can be divided into T
1and T
2two classes, correspondence is just strengthening and is bearing enhancing radiography two kinds of effects respectively.Fe
3o
4nanoparticle, due to its good superparamagnetism, can be used as T
2radiography, its using dosage is little, and toxic and side effects is little, thus has very large research potential.
CT is a kind of conventional diagnostic process means equally, and can provide the three dimensional structure details of high-resolution tissue efficiently, it mainly divides unenhanced and contrast enhancement.Contrast agent conventional on the market is at present mainly containing iodine micromolecule contrast agent, and what laboratory synthesized contains iodine rare-earth europium (III) coordination compound Eu (AA)
2(DTA) Phen, has CT simultaneously, fluorescent dual function, is to a kind of linguistic term containing iodine micromolecule contrast agent, has very large Scientific Research Potential.
Give composite nano-microsphere several functions is study hotspot always.Multiple imaging means is often also used to combine to reach higher diagnostic accuracy in image-forming diagnose.Therefore, we attempt with styrene and have CT, fluorescent dual-function be shell containing iodine rare-earth europium (III) coordination compound, with Fe
3o
4nanoparticle is core, is made have rare-earth fluorescent, the polymer microsphere of MRI and CT radiography triple functions by the method for two-step method seeded soap-free emulsion polymerization, although the microsphere with this type of triple functions has been reported, with containing iodine rare earth compounding and Fe
3o
4the microsphere that nanoparticle combines rarely has report, has very large researching value.
Summary of the invention
The object of the present invention is to provide a kind of new CT, MRI, the preparation method of rare-earth fluorescent three functional microsphere, and attempt as potential MRI and CT contrast agent, be applied at biomedicine field.
The present invention adopts following technical scheme:
New CT of the present invention, MRI, rare-earth fluorescent three functional microsphere, kernel is Fe
3o
4nanoparticle, shell is styrene and have CT, fluorescent dual-function containing iodine rare-earth europium (III) coordination compound Eu (AA)
2(DTA) Phen.
The particle diameter of described microsphere is 50-200nm.
Described microsphere can produce the fluorescence emission peak of 593nm and 617nm two wavelength under the uv excitation light that wavelength is 276nm irradiates.
Described three functional microsphere microspheres have T
2weighting nuclear-magnetism contrast imaging (MRI) effect, its contrasting effects is directly proportional to Concentraton gradient.
Described three functional microspheres have CT scan (CT) effect, and its contrasting effects is directly proportional to Concentraton gradient.
New CT of the present invention, MRI, rare-earth fluorescent three functional microsphere is obtained by the method for two-step method seeded soap-free emulsion polymerization, and concrete grammar is as follows:
(1) with acrylic acid, the adjacent luxuriant and rich with fragrance hello purine of 1,10-, CT prepared by amidotrizoic acid, fluorescent dual-function containing iodine rare-earth europium (III) coordination compound Eu (AA)
2(DTA) Phen; Fe is prepared with chemical coprecipitation
3o
4nanoparticle, adds oleic acid, and the modification of undecylenic acid sodium two step becomes aqueous;
(2) by aqueous Fe
3o
4nanoparticle, styrene, glycidyl methacrylate and initiator potassium persulfate are added to the water, and stir in reactor, at 60-80 DEG C, react 1-2h, add Eu (AA)
2(DTA) Phen, continues reaction 4-7h, obtains new CT of the present invention, MRI, rare-earth fluorescent three functional microsphere emulsion.
In step (1), CT, fluorescent dual-function containing iodine rare-earth europium (III) coordination compound Eu (AA)
2(DTA) preparation method of Phen is:
Step one: by acrylic acid (AA), 1, the adjacent luxuriant and rich with fragrance hello purine (Phen) of 10-, amidotrizoic acid (DTA) adds reactor with the mol ratio of 2.5:1:1.5, the mixed solution of second alcohol and water selected by solvent, amount of alcohol added is that the adjacent luxuriant and rich with fragrance hello purine of every 1mmol adds 45ml, and mixed proportion is ethanol and water volume ratio 5:1, uniform stirring;
Step 2: the alcoholic solution (0.1mol/L) of Europium chloride is added reactor, wherein the mol ratio of Europium chloride and the adjacent luxuriant and rich with fragrance hello purine of 1,10-is 1:1, uniform stirring, and temperature controls at 60 DEG C, reaction 7h;
Step 3: filtered by product obtained for step 2, alcohol wash 4 times, is placed in vacuum drying oven, 40 DEG C of vacuum dryings, both obtains white powder product.
In step (1), oleic acid, undecylenic acid sodium and Fe
3o
4the mass ratio of nanoparticle is (1-3): (1-2): 1.
In step (2), aqueous Fe
3o
4nanoparticle, styrene, glycidyl methacrylate and initiator, Eu (AA)
2(DTA) addition of Phen accounts for the ratio of gross mass and is: 5-8wt%, 3-5wt%, 0.1-0.6wt%, 0.05-0.2wt%, 0.1-0.2wt%, all the other are the content of aqueous solvent.
New CT of the present invention, MRI, rare-earth fluorescent three functional microsphere may be used for biomedicine field optical imagery, CT and MRI field.
New CT of the present invention, MRI, the Fe that rare-earth fluorescent three functional microsphere is inner coated
3o
4nanoparticle gives its nuclear-magnetism contrast imaging (MRI) function, and the coordination compound of microsphere housing parts gives its CT scan (CT) and fluorescent functional.The uniform particle diameter of described microsphere, synthesis condition is simple, and biocompatibility is good, has good MRI and CT imaging effect, belongs to the crossing domain of material and biological medicine, have potential using value.
Good effect of the present invention is as follows:
The present invention uses seeded soap-free emulsion polymerization, and synthesis condition is green gentle, avoids emulsifying agent to affect.Fe
3o
4nanoparticle covered effect is good, microspherulite diameter uniform, controllable, and magnetic kernel and the polystyrene organic layer contained between iodine rare earth compounding layer can reduce Fluorescence-quenching, microsphere has CT simultaneously, MRI, rare-earth fluorescent triple functions, can as potential Medical CT, the contrast agent of MRI equipment.The preparation of this type of multi-functional microsphere also provides a kind of thinking direction newly, has good research application potential.
Accompanying drawing explanation
Fig. 1 is new CT in example 2, MRI, and rare-earth fluorescent three functional microsphere is at the image of transmission electron microscope TEM.
Fig. 2 is new CT in example 3, MRI, the MRI contrastographic picture of rare-earth fluorescent three functional microsphere in experimental mouse body.
Fig. 3 is new CT in example 3, MRI, the external CT contrastographic picture of rare-earth fluorescent three functional microsphere.
Detailed description of the invention
The following examples describe in further detail of the present invention.
Embodiment 1
Step one: with Europium chloride, acrylic acid (AA), the adjacent luxuriant and rich with fragrance hello purine (Phen) of 1,10-, amidotrizoic acid (DTA) prepares CT with mol ratio 2.5:1:1.5, fluorescent dual-function containing iodine rare-earth europium (III) coordination compound Eu (AA)
2(DTA) Phen; Fe is prepared with chemical coprecipitation
3o
4nanoparticle, adds oleic acid, and the modification of undecylenic acid sodium two step becomes aqueous.
Step 2: by aqueous Fe
3o
4nanoparticle, styrene, glycidyl methacrylate and initiator potassium persulfate are added to the water, and stir in reactor, at 60 DEG C, react 1h, add Eu (AA)
2(DTA) Phen, continues reaction 4h, obtains a kind of new CT, MRI, rare-earth fluorescent three functional microsphere emulsion.Wherein, aqueous Fe
3o
4nanoparticle, styrene, glycidyl methacrylate and initiator, Eu (AA)
2(DTA) addition of Phen accounts for the ratio of gross mass and is: 5wt%, 3.5wt%, 0.3wt%, 0.05wt%, 0.1wt%, all the other are the content of aqueous solvent.
Embodiment 2
Step one: with Europium chloride, acrylic acid (AA), the adjacent luxuriant and rich with fragrance hello purine (Phen) of 1,10-, amidotrizoic acid (DTA) prepares CT with mol ratio 2.5:1:1.5, fluorescent dual-function containing iodine rare-earth europium (III) coordination compound Eu (AA)
2(DTA) Phen; Fe is prepared with chemical coprecipitation
3o
4nanoparticle, adds oleic acid, and the modification of undecylenic acid sodium two step becomes aqueous.
Step 2: by aqueous Fe
3o
4nanoparticle, styrene, glycidyl methacrylate and initiator potassium persulfate are added to the water, and stir in reactor, at 70 DEG C, react 1h, add Eu (AA)
2(DTA) Phen, continues reaction 5h, obtains a kind of new CT, MRI, rare-earth fluorescent three functional microsphere emulsion.Wherein, aqueous Fe
3o
4nanoparticle, styrene, glycidyl methacrylate and initiator, Eu (AA)
2(DTA) addition of Phen accounts for the ratio of gross mass and is: 6wt%, 4wt%, 0.4wt%, 0.1wt%, 0.1wt%, all the other are the content of aqueous solvent.
Embodiment 3
Step one: with Europium chloride, acrylic acid (AA), the adjacent luxuriant and rich with fragrance hello purine (Phen) of 1,10-, amidotrizoic acid (DTA) prepares CT with mol ratio 2.5:1:1.5, fluorescent dual-function containing iodine rare-earth europium (III) coordination compound Eu (AA)
2(DTA) Phen; Fe is prepared with chemical coprecipitation
3o
4nanoparticle, adds oleic acid, and the modification of undecylenic acid sodium two step becomes aqueous.
Step 2: by aqueous Fe
3o
4nanoparticle, styrene, glycidyl methacrylate and initiator potassium persulfate are added to the water, and stir in reactor, at 70 DEG C, react 1h, add Eu (AA)
2(DTA) Phen, continues reaction 5h, obtains a kind of new CT, MRI, rare-earth fluorescent three functional microsphere emulsion.Wherein, aqueous Fe
3o
4nanoparticle, styrene, glycidyl methacrylate and initiator, Eu (AA)
2(DTA) addition of Phen accounts for the ratio of gross mass and is: 6.5wt%, 4wt%, 0.5wt%, 0.1wt%, 0.1wt%, all the other are the content of aqueous solvent.
Embodiment 4
Step one: with Europium chloride, acrylic acid (AA), the adjacent luxuriant and rich with fragrance hello purine (Phen) of 1,10-, amidotrizoic acid (DTA) prepares CT with mol ratio 2.5:1:1.5, fluorescent dual-function containing iodine rare-earth europium (III) coordination compound Eu (AA)
2(DTA) Phen; Fe is prepared with chemical coprecipitation
3o
4nanoparticle, adds oleic acid, and the modification of undecylenic acid sodium two step becomes aqueous.
Step 2: by aqueous Fe
3o
4nanoparticle, styrene, glycidyl methacrylate and initiator potassium persulfate are added to the water, and stir in reactor, at 75 DEG C, react 1-2h, add Eu (AA)
2(DTA) Phen, continues reaction 6h, obtains a kind of new CT, MRI, rare-earth fluorescent three functional microsphere emulsion.Wherein, aqueous Fe
3o
4nanoparticle, styrene, glycidyl methacrylate and initiator, Eu (AA)
2(DTA) addition of Phen accounts for the ratio of gross mass and is: 7wt%, 3wt%, 0.5wt%, 0.05wt%, 0.15wt%, all the other are the content of aqueous solvent.
Embodiment 5
Step one: with Europium chloride, acrylic acid (AA), the adjacent luxuriant and rich with fragrance hello purine (Phen) of 1,10-, amidotrizoic acid (DTA) prepares CT with mol ratio 2.5:1:1.5, fluorescent dual-function containing iodine rare-earth europium (III) coordination compound Eu (AA)
2(DTA) Phen; Fe is prepared with chemical coprecipitation
3o
4nanoparticle, adds oleic acid, and the modification of undecylenic acid sodium two step becomes aqueous.
Step 2: by aqueous Fe
3o
4nanoparticle, styrene, glycidyl methacrylate and initiator potassium persulfate are added to the water, and stir in reactor, at 75 DEG C, react 1.5h, add Eu (AA)
2(DTA) Phen, continues reaction 6h, obtains a kind of new CT, MRI, rare-earth fluorescent three functional microsphere emulsion.Wherein, aqueous Fe
3o
4nanoparticle, styrene, glycidyl methacrylate and initiator, Eu (AA)
2(DTA) addition of Phen accounts for the ratio of gross mass and is: 7wt%, 3wt%, 0.6wt%, 0.1wt%, 0.2wt%, all the other are the content of aqueous solvent.
Fig. 1 is TEM (Tecnai G20, the FEI Corp.USA) design sketch of microsphere of the present invention, and as seen from the figure, microsphere size is homogeneous, only has about 100nm, good dispersion in aqueous phase, substantially even coated Fe in each microsphere
3o
4nanoparticle.
Fig. 2 is that microsphere of the present invention is at clinical MR (MAGNETOM Trio, A TimSystem 3T, Siemens, Munich, Germany) upper Mice Body interimage design sketch, Measuring Time point is respectively: 0min, 30min, 60min, 120min, 180min, 300min.As seen from the figure, along with the prolongation of time, microsphere progresses into kidney, spleen, and contrasting effects increases gradually, and can continue long time (>300min).
Fig. 3 is that the design sketch of the external CT (Aquilion ONE 640, Toshiba, Japan) of microsphere is shown, as seen from the figure, from right to left, along with the increase of microsphere concentration, CT contrasting effects strengthens.
Although illustrate and describe embodiments of the invention, for the ordinary skill in the art, be appreciated that and can carry out multiple change, amendment, replacement and modification to these embodiments without departing from the principles and spirit of the present invention, scope of the present invention is by claims and equivalents thereof.
Claims (8)
1. a new CT, MRI, rare-earth fluorescent three functional microsphere, is characterized in that: described microsphere kernel is Fe
3o
4nanoparticle, shell is styrene and have CT, fluorescent dual-function containing iodine rare-earth europium (III) coordination compound Eu (AA)
2(DTA) Phen.
2. new CT as claimed in claim 1, MRI, rare-earth fluorescent three functional microsphere, is characterized in that: the particle diameter of described microsphere is 50-200nm.
3. new CT as claimed in claim 1, MRI, rare-earth fluorescent three functional microsphere, is characterized in that: described microsphere can produce the fluorescence emission peak of 593nm and 617nm two wavelength under the uv excitation light that wavelength is 276nm irradiates.
4. prepare the new CT as described in any one of claim 1-3, MRI, the method for rare-earth fluorescent three functional microsphere, is characterized in that: described microsphere is obtained by the method for two-step method seeded soap-free emulsion polymerization, and concrete grammar is as follows:
(1) with acrylic acid, the adjacent luxuriant and rich with fragrance hello purine of 1,10-, CT prepared by amidotrizoic acid, fluorescent dual-function containing iodine rare-earth europium (III) coordination compound Eu (AA)
2(DTA) Phen; Fe is prepared with chemical coprecipitation
3o
4nanoparticle, adds oleic acid, and the modification of undecylenic acid sodium two step becomes aqueous;
(2) by aqueous Fe
3o
4nanoparticle, styrene, glycidyl methacrylate and initiator potassium persulfate are added to the water, and stir in reactor, at 60-80 DEG C, react 1-2h, add Eu (AA)
2(DTA) Phen, continues reaction 4-7h, obtains new CT of the present invention, MRI, rare-earth fluorescent three functional microsphere emulsion.
5. preparation method as claimed in claim 1, is characterized in that: in step (1), CT, and the preparation method containing iodine rare-earth europium (III) coordination compound Eu (AA) 2 (DTA) Phen of fluorescent dual-function is as follows:
Step one: by acrylic acid (AA), 1, the adjacent luxuriant and rich with fragrance hello purine (Phen) of 10-, amidotrizoic acid (DTA) adds reactor with the mol ratio of 2.5:1:1.5, the mixed solution of second alcohol and water selected by solvent, amount of alcohol added is that the adjacent luxuriant and rich with fragrance hello purine of every 1mmol adds 45ml, and mixed proportion is ethanol and water volume ratio 5:1, uniform stirring;
Step 2: the alcoholic solution of Europium chloride is added reactor, wherein in alcoholic solution, the concentration of Europium chloride is 0.1mol/L, and the mol ratio of Europium chloride and the adjacent luxuriant and rich with fragrance hello purine of 1,10-is 1:1, uniform stirring, and temperature controls at 60 DEG C, reaction 7h;
Step 3: filtered by product obtained for step 2, alcohol wash 4 times, is placed in vacuum drying oven, 40 DEG C of vacuum dryings, both obtains white powder product.
6. preparation method as claimed in claim 1, is characterized in that: in step (1), oleic acid, undecylenic acid sodium and Fe
3o
4the mass ratio of nanoparticle is (1-3): (1-2): 1.
7. preparation method as claimed in claim 1, is characterized in that: in step (2), aqueous Fe
3o
4nanoparticle, styrene, glycidyl methacrylate and initiator, Eu (AA)
2(DTA) addition of Phen accounts for the ratio of gross mass and is: 5-8wt%, 3-5wt%, 0.1-0.6wt%, 0.05-0.2wt%, 0.1-0.2wt%, all the other are the content of aqueous solvent.
8. the new CT as described in any one of claim 1-3, MRI, rare-earth fluorescent three functional microsphere at biomedicine field optical imagery, the application of CT and MRI.
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CN114984874A (en) * | 2022-06-20 | 2022-09-02 | 重庆理工大学 | Method for preparing magnetic/fluorescent/temperature-sensitive colloidal crystal microspheres by micro-fluidic method and product thereof |
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CN105963721A (en) * | 2016-06-06 | 2016-09-28 | 湖北大学 | BaGdF5 and europium-polyphenols reticulation nanocomposite and preparation method and application thereof |
CN106237346A (en) * | 2016-08-05 | 2016-12-21 | 湖北大学 | A kind of MRI guides photo-thermal therapy multi-functional diagnosis and treatment probe and its preparation method and application |
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CN114984874A (en) * | 2022-06-20 | 2022-09-02 | 重庆理工大学 | Method for preparing magnetic/fluorescent/temperature-sensitive colloidal crystal microspheres by micro-fluidic method and product thereof |
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