CN103143042A - Superpara magnetism polymeric microsphere magnetic resonance imaging (MRI) contrast agent and preparation method thereof - Google Patents

Superpara magnetism polymeric microsphere magnetic resonance imaging (MRI) contrast agent and preparation method thereof Download PDF

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CN103143042A
CN103143042A CN201310045055XA CN201310045055A CN103143042A CN 103143042 A CN103143042 A CN 103143042A CN 201310045055X A CN201310045055X A CN 201310045055XA CN 201310045055 A CN201310045055 A CN 201310045055A CN 103143042 A CN103143042 A CN 103143042A
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contrast agent
magnetic resonance
resonance imaging
polymer microballoon
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CN103143042B (en
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戴李宗
陈凌南
曾碧榕
康启龙
高辉
罗伟昂
许一婷
余世荣
叶华立
李聪
陈国荣
毛杰
刘新瑜
何凯斌
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Xiamen University
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Abstract

The invention discloses a superpara magnetism polymeric microsphere magnetic resonance imaging (MRI) contrast agent and a preparation method of the superpara magnetism polymeric microsphere MRI contrast agent, and relates to the MRI contrast agent used for diagnosis and treatment and the preparation method of the MRI contrast agent used for the diagnosis and the treatment. Polymeric microspheres are formed by polymerizable amphiphilic macromolecules, styrene monomers and Fe3O4 nano particles in a one-time batch feeding polymerization mode. Each microsphere comprises a core-shell structure, an inner core envelopes the superpara magnetism Fe3O4 particles, and a shell layer surface contains abundant functional groups. The microspheres are enabled to have targeting functions through coupling targeting molecules, and suitable for targeting MRI for certain diseases. The superpara magnetism polymeric microspheres are simple in synthetic process, low in preparation cost, controllable in microsphere particle diameter, stable in form, good in biocompatibility (BC) and MRI effect, and good in popularization and application values.

Description

A kind of superparamagnetic polymer microballoon magnetic resonance imaging contrast agent and preparation method thereof
Technical field
The invention belongs to composite and molecular image field, relate to a kind of magnetic resonance imaging contrast agent and preparation method thereof, magnetic resonance imaging contrast agent that especially a kind of superparamagnetic polymer microballoon builds and preparation method thereof.
Background technology
Nuclear magnetic resonance (MRI) is one of detection means the strongest in current clinical diagnosis, safety with radiationless damage, can be to technology motilities such as arbitrary orientation tomoscans, the details of spatial resolution and physiological tissue and organ clearly can be provided.In MRI, because the relaxation time of some different tissues or tumor tissues is overlapped, can not carries out dynamic scan and measure organ dysfunction, need to improve image contrast by contrast medium.
Magnetic resonance imaging contrast agent can be divided into paramagnetism contrast medium, ferromagnetism contrast medium and superparamagnetism contrast medium usually, and they are all to reach the radiography purpose by the intensity that interior extraneous relaxation effect and susceptibility change tissue signal indirectly.The advantages such as wherein, the superparamagnetism contrast medium has specificity owing to distributing in human body, using dosage is few, safety, toxic and side effects are little become the focus of present research and development.In this field, (the preparation method of magnetic resonance imaging contrast agent of magnetic water-soluble chitosan such as Zhang Qi, Chinese patent, CN101890173A) with degradation of chitosan be water solublity narrow molecular-weight oligo-chitosan, then add the superparamagnetism metal inorganic salt, utilize metal inorganic salt to be hydrolyzed under alkali condition, generate magnetic nano-particle at water solublity narrow molecular-weight oligo-chitosan situ, obtain superparamagnetic water-soluble chitosan magnetic resonance imaging contrast agent after magnetic separates drying; Cai Weis etc. (a kind of Superparamagnetism magnetic resonance contrast medium and preparation method thereof, Chinese patent, publication number CN101002951A) disclose the Fe that a kind of surface coats polyhydric alcohol 3O 4Nanoparticle, its preparation method be with iron containing compounds in polyhydric alcohol solutions through pyroreaction, cooling, precipitate, separate, be scattered in aqueous solution and filtration sterilization finally obtains a kind of Superparamagnetism magnetic resonance imaging contrast; (the magnetic resonance contrast agent that a kind of amphiphilic polysaccharide parcel superparamagnetic nanoparticle builds and preparation method thereof such as Ai Hua, Chinese patent, publication number CN102380109A) form micelle based on non-polymerizable type amphiphile, amphiphilic molecule self assembly effect, refill and carry hydrophobicity superparamagnetic nanoparticle acquisition water-soluble compound.The prepared stable composite of this kind method is poor, and the poor controllability in operating process, is not suitable for the application of complex environment.Poplar bodyguard equality (a kind of Fe3O4 SiO2-T nanoparticle and its preparation method and application, Chinese patent, publication number CN102085381A) adopts high temperature pyrolysis to prepare Fe 3O 4Nanoparticle wraps up silicon dioxide and is connected amino, then connects the magnetic resonance sensors that thymus pyrimidine has prepared a kind of magnetic resonance imaging contrast agent and detected mercury ion, but its application under alkali condition is restricted.
In sum, relevant superparamagnetic polymer microballoon magnetic resonance imaging contrast agent especially has nucleocapsid structure, embedded Fe 3O 4Nanoparticle, particle diameter are controlled, magnetic resonance imaging contrast agent that acid-fast alkali-proof is good there is not yet report.
Superparamagnetic polymer microballoon magnetic resonance imaging contrast agent of the present invention is with polymerisable parents' macromole, styrene monomer and Fe 3O 4Nanoparticle is through the initiated polymerization that once feeds intake, and method is simple.Wherein, polymerisable parents' macromole is that the different pure dibasic acid esters of maleic acid (being made through two step esterifications by maleic anhydride, octadecanol, Polyethylene Glycol) can participate in cinnamic polymerization, make microsphere have good stability, not only can solve common polyhydric alcohol to Fe 3O 4The problem that the nanoparticle parcel is not firm, but also overcome general silica as the not alkaline-resisting limitation of shell, possess good acid-fast alkali-proof; Simultaneously, Polyethylene Glycol gives shell abundant hydroxyl, makes microsphere have target function by the coupling targeted molecular.Microsphere good biocompatibility of the present invention, MRI imaging effect are good, and particle diameter is controlled, can prepare the microsphere of 20 ~ 500nm, satisfies the imaging radiography demand of different tissues and pathological changes, has potential using value.
Summary of the invention
The object of the invention is to provide a kind of superparamagnetic polymer microballoon magnetic resonance imaging contrast agent and preparation method thereof.
Described a kind of superparamagnetic polymer microballoon magnetic resonance imaging contrast agent is by polymerisable parents' macromole, styrene monomer and Fe 3O 4Nanoparticle is through the initiated polymerization that once feeds intake; Microsphere is nucleocapsid structure, and kernel is polystyrene and inlays Fe 3O 4Nanoparticle, shell are polymerisable parents' macromole.
Described polyalcohol microspherulite diameter is 20 ~ 500nm.
Described Fe 3O 4Nano particle diameter is 2 ~ 10nm.
Described polymerisable parents' macromole is that maleic anhydride, long-chain fatty alcohol, Polyethylene Glycol obtain through two step esterifications.
The preparation method of described a kind of superparamagnetic polymer microballoon magnetic resonance imaging contrast agent is as follows:
(1) chemical coprecipitation prepares magnetic Fe 3O 4Nanoparticle adds the long-chain unsaturated fatty acid modification, improves Fe 3O 4The hydrophobicity of nanoparticle surface.
(2) with Fe 3O 4Nanoparticle, styrene monomer, the different pure dibasic acid esters of maleic acid, initiator are added to the water, and react 12 ~ 36h under 50 ~ 80 ℃ namely to obtain a kind of superparamagnetic polymer microballoon magnetic resonance contrast agent.
(3) step (2) gained superparamagnetic polymer microballoon magnetic flux is crossed coupling folic acid, obtain having the magnetic resonance contrast agent of target function.
Described long-chain unsaturated fatty acid is a kind of in the long-chain unsaturated fatty acids such as oleic acid, 9-undecylenic acid, tridecylenic acid, and consumption is Fe 3O 41 ~ 1.5 times of nanoparticle.
Described Fe 3O 4The content of nanoparticle, styrene monomer, the different pure dibasic acid esters of maleic acid, initiator is followed successively by: 1 ~ 5wt%, 5 ~ 15wt%, 0.001 ~ 5wt%, 0.001 ~ 1wt%, surplus is deionized water.
Described initiator is azo-initiator, organic peroxy class initiator, redox system etc., as azodiisobutyronitrile, potassium peroxydisulfate, benzoyl peroxide etc.
The particle diameter of superparamagnetic polymer microballoon of the present invention is controlled, and the microsphere that can prepare as required different-grain diameter carries out radiography to different tissues and organ; The nucleocapsid structure of polymer microballoon has not only improved stability and the acid-fast alkali-proof of contrast medium greatly, can also carry out the different targeted molecular of coupling by the abundant functional group of microsphere surface, satisfies the radiography demand of different lesions.Simultaneously, superparamagnetic polymer microballoon magnetic resonance imaging contrast agent toxic and side effects of the present invention is little, has the applications well prospect.
The explanation of accompanying drawing table
The TEM of superparamagnetic polymer microballoon magnetic resonance imaging contrast agent figure in Fig. 1 embodiment 1.
The hysteresis curve figure of Fig. 2 embodiment 1 superparamagnetic polymer microballoon magnetic resonance imaging contrast agent.
The nuclear magnetic resonance figure of Fig. 3 embodiment 1 and embodiment 2 superparamagnetic polymer microballoons (Varian7.0T MRI, 1～4 represents that respectively the magnetic microsphere concentration ratio is 1,1/2,1/4 and 1/8, upper row is embodiment 1 experimental result, low-grades are embodiment 2 experimental results).
1/T in Fig. 4 embodiment 1 2Concern matched curve with concentration change.
The experimental result of table 1 embodiment 2～9.
The cell survival experimental result of table 2 embodiment 11～15.
The specific embodiment
The present invention will be further described below by embodiment.
The preparation of embodiment 1 superparamagnetic polymer microballoon magnetic resonance imaging contrast agent
With 5.41gFeCl 36H 2O and 2.78gFeSO 47H 2O is dissolved in the 40mL deionized water, logical nitrogen deoxygenation 30min; 3.54gNaOH be dissolved in the 10mL deionized water, slowly add, add 2mL oleic acid after 60 ℃ of reaction 1h, be warming up to 80 ℃ of ripenings one hour, obtain the magnetic Fe with superparamagnetism of size 2 ~ 10nm 3O 4Nanoparticle.With the magnetic Fe after modification 3O 4Nanoparticle with washing with alcohol 2 ~ 3 times to neutral, dry for standby.Get made 0.4gFe 3O 4Nanoparticle, 2mL styrene, the different pure dibasic acid esters of 0.04g maleic acid, 40mL deionized water once feed intake, add the 0.02g Ammonium persulfate. and be warming up to 65 ℃ of reaction 12 ~ 36h after stirring 30min, the superparamagnetic polymer microballoon magnetic that obtains particle diameter 200 ~ 300nm is total to contrast medium; Magnetic separates, and dialysis separates purifies to microsphere.
The structure of prepared superparamagnetic polymer microballoon magnetic resonance imaging contrast agent is characterized by the JEM-2100 high-resolution-ration transmission electric-lens, two-layer core shell structure as can be seen from Fig. 1, particle diameter is 200 ~ 300nm, internal layer is polystyrene, skin is the different pure dibasic acid esters of poly, and as seen is inlaid with Fe at kernel 3O 4Nanoparticle; Its magnetic property is measured (Fig. 2) by SQUID superconductive quantum interference gaussmeter, and result shows remanent magnetization and coercivity all close to 0, almost exists without magnetic hysteresis, has superparamagnetism; Utilize the 7.0T magnetic resonance imager to characterize the nuclear magnetic resonance effect of variable concentrations superparamagnetic polymer microballoon magnetic resonance imaging contrast agent, result is compared with pure water as shown in Figure 3, and microsphere has good nuclear magnetic resonance contrast; For ease of describing relaxation process, usually T 2Inverse be defined as relaxation rate R 2, Fig. 4 be the relaxation rate that calculates with the relation curve of magnetic microsphere concentration change, visible relaxation rate and solution concentration satisfy linear relationship preferably.
Embodiment 2 ~ 9
With embodiment 1 technique, change feeding intake of styrene, the different pure dibasic acid esters of maleic acid, Ammonium persulfate., the superparamagnetic polymer microballoon magnetic resonance contrast agent of preparation different-grain diameter, result is as shown in table 1.
Embodiment 10 superparamagnetic polymer microballoon magnetic resonance imaging contrast agent cytotoxicity tests
The Hela cell is implanted in 10mL Tissue Culture Dish bottle, and condition is 37 ℃, saturated humidity, 5%CO 2, cultivating system is that superparamagnetic polymer microballoon magnetic resonance imaging contrast agent concentration is the DMEM culture medium of 100 μ g/mL.The survival rate of experimental result cell reaches 89%, illustrates that toxic and side effects is little.
Embodiment 11 ~ 15
With embodiment 10 techniques, change superparamagnetic polymer microballoon magnetic resonance imaging contrast agent concentration, gained cell survival rate experimental result is as shown in table 2.
Embodiment 16 has the preparation of the superparamagnetic polymer microballoon magnetic resonance imaging contrast agent of target function
With the folic acid solution of phosphate buffer preparation 1mg/mL, get 10mL and add 40mg1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloric acid, 100mgN-N-Hydroxysuccinimide and 40mg superparamagnetic polymer microballoon, stir 24h under nitrogen protection.After reaction finishes, sample is carried out magnetic separate, with phosphate buffer washing 2 ~ 3 times, last lyophilization 36h namely gets the superparamagnetic polymer microballoon magnetic resonance imaging contrast agent with target function.
Table 1
Embodiment 2 3 4 5 6 7 8 9
Fe 3O 4/g 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4
Styrene/mL 2 2 2 2 2 2 2 2
Deionized water/mL 40 40 40 40 40 40 40 40
Ammonium persulfate ./g 0.020 0.020 0.021 0.021 0.021 0.022 0.023 0.024
The different pure dibasic acid esters/g of maleic acid 0.02 0.03 0.06 0.08 0.10 0.20 0.30 0.40
Microsphere average grain diameter/nm 489 423 189 146 109 61 47 28
Table 2
Figure BDA00002816783700041

Claims (8)

1. superparamagnetic polymer microballoon magnetic resonance imaging contrast agent is by polymerisable parents' macromole, styrene monomer and Fe 3O 4The nanoparticle initiated polymerization forms; Microsphere is nucleocapsid structure, and kernel is polystyrene and inlays Fe 3O 4Nanoparticle, shell are polymerisable parents' macromole.
2. a kind of superparamagnetic polymer microballoon magnetic resonance imaging contrast agent according to claim 1, is characterized in that described polyalcohol microspherulite diameter is 20 ~ 500nm.
3. a kind of superparamagnetic polymer microballoon magnetic resonance imaging contrast agent according to claim 1, is characterized in that described Fe 3O 4Nano particle diameter is 2 ~ 10nm.
4. a kind of superparamagnetic polymer microballoon magnetic resonance imaging contrast agent according to claim 1 is characterized in that described polymerisable parents' macromole is that maleic anhydride, long-chain fatty alcohol, Polyethylene Glycol obtain through two step esterifications.
5. the preparation method of a superparamagnetic polymer microballoon magnetic resonance imaging contrast agent is characterized in that step is as follows:
(1) chemical coprecipitation prepares magnetic Fe 3O 4Nanoparticle adds the long-chain unsaturated fatty acid modification, improves Fe 3O 4The hydrophobicity of nanoparticle surface;
(2) with Fe 3O 4Nanoparticle, styrene monomer, the different pure dibasic acid esters of maleic acid, initiator are added to the water, and react 12 ~ 36h under 50 ~ 80 ℃ namely to obtain a kind of superparamagnetic polymer microballoon magnetic resonance contrast agent;
(3) step (2) gained superparamagnetic polymer microballoon magnetic flux is crossed coupling folic acid, obtain having the magnetic resonance contrast agent of target function.
6. the preparation method of a kind of superparamagnetic polymer microballoon magnetic resonance imaging contrast agent according to claim 5, it is characterized in that described long-chain unsaturated fatty acid is a kind of in the long-chain unsaturated fatty acids such as oleic acid, 9-undecylenic acid, tridecylenic acid, consumption is Fe 3O 41 ~ 1.5 times of nanoparticle.
7. the preparation method of a kind of superparamagnetic polymer microballoon magnetic resonance imaging contrast agent according to claim 5, is characterized in that described Fe 3O 4The content of nanoparticle, styrene monomer, the different pure dibasic acid esters of maleic acid, initiator is followed successively by: 1 ~ 5wt%, 5 ~ 15wt%, 0.001 ~ 5wt%, 0.001 ~ 1wt%, surplus is deionized water.
8. the preparation method of a kind of superparamagnetic polymer microballoon magnetic resonance imaging contrast agent according to claim 5, is characterized in that described initiator is azo-initiator, organic peroxy class initiator, redox system.
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