CN108079321A - A kind of efficient magnetic resonance contrast agent of magnetic iron oxide - Google Patents

A kind of efficient magnetic resonance contrast agent of magnetic iron oxide Download PDF

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CN108079321A
CN108079321A CN201611037993.5A CN201611037993A CN108079321A CN 108079321 A CN108079321 A CN 108079321A CN 201611037993 A CN201611037993 A CN 201611037993A CN 108079321 A CN108079321 A CN 108079321A
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peg
magnetic resonance
iron oxide
magnetic
contrast agent
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韩会义
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    • 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
    • A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
    • A61K49/10—Organic compounds
    • A61K49/12—Macromolecular compounds
    • A61K49/126—Linear polymers, e.g. dextran, inulin, PEG
    • 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
    • A61K49/1851—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 an organic macromolecular compound, i.e. oligomeric, polymeric, dendrimeric organic molecule
    • A61K49/1857—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 an organic macromolecular compound, i.e. oligomeric, polymeric, dendrimeric organic molecule the organic macromolecular compound being obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. PLGA
    • A61K49/186—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 an organic macromolecular compound, i.e. oligomeric, polymeric, dendrimeric organic molecule the organic macromolecular compound being obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. PLGA the organic macromolecular compound being polyethyleneglycol [PEG]

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Nanotechnology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Radiology & Medical Imaging (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Molecular Biology (AREA)
  • Immunology (AREA)
  • Medicinal Chemistry (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Magnetic Resonance Imaging Apparatus (AREA)

Abstract

Using high temperature thermal decomposition method, the homogeneous ferric oxide nano particles of pattern have been prepared by solvent, reducing agent and dressing agent of hydrophily Organic Alcohol PEG for a kind of efficient magnetic resonance contrast agent of magnetic iron oxide.PEG is successfully modified on the surface of ferric oxide nano particles, can be stably dispersed in deionized water.Magnetic property analysis result shows that sample has superparamagnetism, and PEG SPIONs have good water dispersible and biocompatibility, and higher r2/r1 values have a good application prospect in terms of the magnetic resonance imaging of biomedical applications.

Description

A kind of efficient magnetic resonance contrast agent of magnetic iron oxide
Technical field
The present invention relates to a kind of contrast agent more particularly to a kind of efficient magnetic resonance contrast agents of magnetic iron oxide.
Background technology
Magnetic ferric oxide nano particles for biomedical sector are usually by Fe3O4Or γ-Fe2O3For core And the dressing agent composition on its surface layer is wrapped in, coating material, with good biocompatibility, may be used as drug by it Carrier, magnetic resonance imaging contrast and tumor magnetic thermal therapy etc..
Ferric oxide nano particles preparation has more report, Sun etc. with ferric acetyl acetonade (Fe (acac)3) for source of iron, phenylate Or benzyl oxide is solvent, oleic acid, oleyl amine are stabilizer, and 1,2- ten six dihydric alcohol is that reducing agent has synthesized the spherical shape that grain size is 4 ~ 8nm Fe3O4Particle.But acquired nano-particle has very strong hydrophobicity, limits its application.And Kim etc. is compound with iron oleate Object is source of iron, and diphenyl ether is solvent, and oleic acid, oleyl alcohol are stabilizer, after nano-particle is obtained by the reaction under high temperature, by further matching somebody with somebody Although body exchange enables ferric oxide nano particles to disperse in deionized water, this makes experimentation become complicated, and into This costliness.At present, domestic medical iron oxide contrast agent depends on import, therefore good using biocompatibility and water solubility The work that good macromolecule organic solvent prepares iron oxide contrast agent is most important.
PEG has the characteristics that good biocompatibility, nontoxic, immunogenicity is low, can be excreted by kidney, in vivo will not There is accumulation, be commonly used to the biochemical drugs such as modifying protein, polypeptide, enzyme and bio-medical material.PEG decorative layers can reduce phagocytosis The phagocytosis of cell increases nano-particle blood circulation time.
The content of the invention
The purpose of the present invention is developing the cost of reduction iron oxide contrast agent, improving its imaging effect, one kind is devised The efficient magnetic resonance contrast agent of magnetic iron oxide.
The technical solution adopted by the present invention to solve the technical problems is：
The raw material for preparing of the efficient magnetic resonance contrast agent of magnetic iron oxide has：Ferric acetyl acetonade；Polyethylene glycol；Deionized water；Toluene, Acetone；
High glycoform DMEM fluid nutrient mediums；Hyclone.
The preparation process of the efficient magnetic resonance contrast agent of magnetic iron oxide is：15gPEG1000 is weighed, is poured into three-neck flask, 80 DEG C are warming up in the case where being stirred continuously, weighs 0.7gFe (acac)3, it is added in flask, crosses heat preservation 10min herein, and be passed through Argon gas, condensation water conservation.260 DEG C are warming up to the heating rate of 7.2 DEG C/min, stops heating after reacting 1h, removes heat source It is cooled to 60 DEG C.Product after cooling is moved among beaker, and the toluene for adding in 60mL carries out ultrasonic disperse, product scatter After, it is adsorbed with magnet in beaker bottom, after black magnetic substance is adsorbed to beaker bottom substantially, supernatant discarding At night, repeat the cleaning process 2 times.Black precipitate is cleaned 2 times again with acetone afterwards, and a part is scattered in deionized water, separately Part vacuum drying, obtains black powder sample.
The beneficial effects of the invention are as follows：
PEG is successfully modified on the surface of ferric oxide nano particles, can be stably dispersed in deionized water.Magnetic property point The result shows that sample has superparamagnetism, PEG-SPIONs has good water dispersible and biocompatibility, higher for analysis R2/r1 values have a good application prospect in terms of the magnetic resonance imaging of biomedical applications.
Specific embodiment
The raw material for preparing of the efficient magnetic resonance contrast agent of magnetic iron oxide has：Ferric acetyl acetonade；Polyethylene glycol；Deionized water； Toluene, acetone；High glycoform DMEM fluid nutrient mediums；Hyclone.
The preparation process of the efficient magnetic resonance contrast agent of magnetic iron oxide is：15gPEG1000 is weighed, is poured into three-neck flask, 80 DEG C are warming up in the case where being stirred continuously, weighs 0.7gFe (acac)3, it is added in flask, crosses heat preservation 10min herein, and be passed through Argon gas, condensation water conservation.260 DEG C are warming up to the heating rate of 7.2 DEG C/min, stops heating after reacting 1h, removes heat source It is cooled to 60 DEG C.Product after cooling is moved among beaker, and the toluene for adding in 60mL carries out ultrasonic disperse, product scatter After, it is adsorbed with magnet in beaker bottom, after black magnetic substance is adsorbed to beaker bottom substantially, supernatant discarding At night, repeat the cleaning process 2 times.Black precipitate is cleaned 2 times again with acetone afterwards, and a part is scattered in deionized water, separately Part vacuum drying, obtains black powder sample.
Using the object phase group of Dutch Panalytical companies χ pert Pro type X ray powder diffractometers analysis sample Into, Cu K α targets, λ=0.15405 nm, operating voltage 40kV, operating current 40mA, sweep speed 2o/min, scanning range 2θ；20o ~80o.It, will with pattern, grain size and the dispersity of Japan Electronics JEOL-2010 type transmission electron microscope observing samples Scattered sample drop in deionized water is added on the copper mesh of carbon film, and the observation of Electronic Speculum load sample platform is put into after drying.Using English The hydration kinetics grain size and Zeta of state's Malvern companies ZEN3690 types nano particle size and Zeta potential analysis-e/or determining sample Potential value.Using the surface group of the NEXUS470 types FTIR spectrum analysis sample of Thermo Electron companies of the U.S. Into test wave-number range is 500 ~ 4000cm-1.The magnetic property of sample uses Quantum Design companies of U.S. MPMSXL-7 types Superconducting quantum interference device (SQUID) measures, and test temperature 300K, magnetic field range is between -60 kA/m and 60 kA/m.Using the U.S. primary OD values at happy 570 nm of company MLDEL680 type microplate reader test cell.Using Perkin Elmer companies of U.S. Optima 7300DV types plasma atomic emission spectrometer measures the content of Fe elements.And by sample preparation into various concentration, using moral 7 T toys magnetic resonance imager of Bruker companies of state Biospec70/30 types observes the T2 relaxivities of test sample, uses Sequence for spin-echo sequence, design parameter is；Repetition time (TR)=10000ms, the echo time (TE)=13,26, 52、104、208、416ms.And sample is further analyzed in the in vivo contrasting effects of Kunming (KM) mouse, specific test parameter is such as Under；The visual field (FOV, field of view)=1.8 × 1.8 cm2, matrix (matrix size)=256 × 256, thickness (slice thickness) =1 mm；Echo time (echo time)=4,11,18,25,32,39,46,53,60,67, 74th, 81ms, repetition time (TR, repetitiontime)=1500ms.
1 h are reacted at 260 DEG C using high temperature thermal decomposition method and prepare the XRD spectrum of sample, as a result with Fe3O4 PDF standard cards Piece (JCPDS 01-085-1436) unanimously, shows to contain Fe in sample3O4Crystalline phase.But Fe3O4Spinel structure and γ- The structure of Fe2O3 is quite similar, also results in Fe3O4With γ-Fe2O3XRD spectral lines it is essentially identical, some researches show that nanostructureds Under magnetic iron oxide particles be usually all Fe3O4With γ-Fe2O3 Mixed phase.According to Scherrer (Debye-Scherrer) formula It can be evaluated whether the particle size of sample, by Scherrer formula D=K λ/(β cos θ), in formula, what D was represented is crystallite dimension；K is represented Be crystal grain form factor, take 0.90；What λ was represented is incident ray wavelength, and value is 0.15405 nm；What β, θ were represented respectively It is the halfwidth and Bragg angle of (311) crystallographic plane diffraction peak.The average crystal particle diameter that sample is calculated using Scherrer formula is 8.9nm。
The surface state of ferric oxide nano particles under the action of FTIR spectrum, 3433,2922,2861, 1633rd, 1381,1093 and 580cm-1All there is strong absworption peak in place.1633cm-1The absworption peak at place comes from-COO-group Symmetrically flexible peak；1381 cm-1Place is-COO-asymmetric flexible peak, and the appearance of-COO-group is due to PEG under pyroreaction Part of hydroxyl aoxidized, and combined with nano-particle.580 cm-1Place is the absworption peak of the Fe-O of iron oxide.3433cm-1Place It is PEG-OH characteristic absorption peaks；2922、2861 cm-1Place is the characteristic peak of the C-H of PEG；1093 cm-1Place be PEG- C-O-C-absworption peak.According to above analysis, PEG has successfully been modified on the surface of ferric oxide nano particles.
At 260 DEG C ferric oxide nano particles made from reaction be scattered in hydration kinetics grain size in deionized water and Zeta potential value, value are respectively 20nm and -5mV.The hydration power footpath usually measured is the grain size, organic by iron oxide particles Package layer thickness, aquation layer thickness three parts form, and transmission electron microscope is the grain size of magnetic core, therefore hydration kinetics grain size is big In the particle size values that transmission electron microscope observing obtains.In experimentation using 15 DEG C/min heating rates nano-particle obtained by the reaction very Easy coagulation and 30d can be stabilized with 7.2 DEG C/min heating rates nano-particle obtained by the reaction in deionized water, Illustrate that heating rate influences the forming process of particle, so as to influence the stability of particle in deionized water.Theoretically, nanoparticle Gravitation comes from Van der Waals force, dipole and magnetic couple strongly between son, and repulsion comes from the row of electrostatic repulsion and steric hindrance Repulsion.PEG-SPIONs institutes charging property is smaller, but particle can be dispersed stably in deionized water, illustrate particle be with Reunion between particle is prevented by means of the space steric effect of PEG finishing coats.
The hysteresis loops of PEG-SPIONs at 300k show：The remanent magnetism and coercivity of sample are all 0, show prepared by experiment PEG-SPIONs possess superparamagnetism, saturation magnetization 53Am2/kg.
The good biocompatibility and hypotoxicity of ferric oxide nano particles extremely important, general in terms of biologic applications to it MCF-7 (human breast cancer cell) is containing 0,3.13,6.25,12.50,25.00,50.00 and 100.00 μ gFe/mL high sugar respectively In DMEM culture mediums (volume fraction be 10% hyclone, 10% mycillin) culture for 24 hours, with mtt assay test cell survival rate, Analyze cytotoxicity.The survival rate of cell illustrates that PEG-SPIONs has than relatively low substantially all more than 90% under different Fe concentration Toxicity, the hypotoxicity of PEG-SPIONs, which is attributable to surface modification, has the PEG of good biocompatibility.
Iron content in using plasma Atomic Emission Spectrometer AES test sample, prepare 0.06,0.11,0.22,0.45, The test sample of 0.90mmol/L, and test its Relaxivity.T2 weighted imagings are dimmed with concentration increase, and it is preferable right to show Compare effect.Ferro element concentration and the fitting of T2 values are obtained into the r2 values of PEG-SPIONs as 171.22mmol/ (L.s), and measure sample The r1 values of product are 1.90 mmol/ (L.s), r2/r1 90.11.R2/r1 values are assessment particles as T1 contrast medium or T2 pairs Than the important parameter of agent, general r2/r1 is higher, and T2 contrasting effects are better.The PEGSPIONs of synthesis shows that preferable T2 adds Imaging effect is weighed, a kind of effective T2 magnetic resonance imaging contrasts can be used as.
In order to examine effects of the PEG-SPIONs as contrast agent, (10 mg Fe/kg are small by tail vein injection PEG-SPIONs Mouse weight), it is scanned by 7T toys magnetic resonance scanner to injecting front and rear mouse.Inject 5min, 10min and 30min Afterwards, the PEG-SPIONs of synthesis shortens the T2 relaxation times of water proton.After injection for 24 hours, the T2* values of mouse different parts are measured Still there is reduction before relative injection, still there is PEG-SPIONs to play contrast action after injection for 24 hours in blood.PEG decorative layers can The phagocytosis of phagocyte is reduced, increases nano-particle blood circulation time, PEG-SPIONs has very long blood halflife, can It is present in the long period in blood.Surface is shown well in the PEG-SPIONs of negative electricity after being injected in Mice Body Contrast enhanced effect illustrates that it can be used as efficient T2 magnetic resonance imaging contrasts.

Claims (2)

1. a kind of efficient magnetic resonance contrast agent of magnetic iron oxide, preparing raw material has：Ferric acetyl acetonade；Polyethylene glycol；Deionized water； Toluene, acetone；High glycoform DMEM fluid nutrient mediums；Hyclone.
2. the efficient magnetic resonance contrast agent of magnetic iron oxide according to claim 1, it is characterized in that preparation process is：It weighs 15gPEG1000 is poured into three-neck flask, and 80 DEG C are warming up in the case where being stirred continuously, and weighs 0.7gFe (acac)3, it is added to flask In, heat preservation 10min is crossed herein, and is passed through argon gas, condensation water conservation；260 DEG C are warming up to the heating rate of 7.2 DEG C/min, Stop heating after reacting 1h, remove heat source and be cooled to 60 DEG C；Product after cooling is moved among beaker, and adds in the first of 60mL Benzene carries out ultrasonic disperse, after product scatter, is adsorbed with magnet in beaker bottom, when black magnetic substance is inhaled substantially After being attached to beaker bottom, at supernatant discarding night, the cleaning process is repeated 2 times；Black precipitate cleans 2 times with acetone again afterwards, and one It is partially dispersed in deionized water, another part vacuum drying obtains black powder sample.
CN201611037993.5A 2016-11-23 2016-11-23 A kind of efficient magnetic resonance contrast agent of magnetic iron oxide Pending CN108079321A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114112097A (en) * 2021-12-08 2022-03-01 华中科技大学 Magnetic nanoparticle temperature measurement method based on electron paramagnetic resonance integral spectrum full width at half maximum

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114112097A (en) * 2021-12-08 2022-03-01 华中科技大学 Magnetic nanoparticle temperature measurement method based on electron paramagnetic resonance integral spectrum full width at half maximum

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CN108079321A (en) A kind of efficient magnetic resonance contrast agent of magnetic iron oxide

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