CN104174037A - A preparation method of a blended contrast agent with T1 and T2 contrast functions - Google Patents

A preparation method of a blended contrast agent with T1 and T2 contrast functions Download PDF

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CN104174037A
CN104174037A CN201310204751.0A CN201310204751A CN104174037A CN 104174037 A CN104174037 A CN 104174037A CN 201310204751 A CN201310204751 A CN 201310204751A CN 104174037 A CN104174037 A CN 104174037A
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contrast agent
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blended
pluronic
ethanol
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CN104174037B (en
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吴仁安
刘荣
徐桂菊
张宇
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Zhangjiagang Institute Of Industrial Technology Dalian Institute Of Chemical Physics China Academy Of Sciences
Dalian Institute of Chemical Physics of CAS
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Abstract

一种具有T1、T2造影功能的掺混型造影剂的制备方法，包括如下步骤：将一种双头双亲有机模板分子溶解于一定溶剂中，然后加入芳香酸、稀土氯化物和ⅥB～ⅧB族氯化物，于适当温度下进行溶剂热反应，制得一种具有T1、T2造影功能的掺混型造影剂纳米粒子。本发明制备的掺混型造影剂材料具有纳米级粒径及较好的T1、T2造影效果。A method for preparing a blended contrast agent with T 1 and T 2 imaging functions, comprising the following steps: dissolving a double-headed amphiphilic organic template molecule in a certain solvent, and then adding aromatic acid, rare earth chloride and VIB～ Group ⅧB chlorides undergo solvothermal reaction at an appropriate temperature to prepare a blended contrast agent nanoparticle with T 1 and T 2 imaging functions. The blended contrast agent material prepared by the invention has a nanoscale particle size and better T 1 and T 2 contrast effects.

Description

One has T 1, T 2the preparation method of the mix type contrast agent of radiography function
Technical field
The invention belongs to contrast agent material field, be specifically related to one and there is T 1, T 2the preparation method of the mix type contrast agent of radiography function.
Background technology
In order to realize targeting efficiency to tumor tissues of gene or pharmaceutical carrier and the dynamic monitoring of therapeutic effect, people introduce carrier by contrast agent conventionally.Because tumor tissues compared with normal structure, has abundant blood vessel network structure, contrast agent can be by the abundant blood vessel network of tumor tissues and vessel wall permeability in the more enrichment of tumor locus.Utilize contrast agent can change the contrast between normal structure and tumor tissues, reach the effect of better observation tumor tissues.
Strengthen type according to developing and divide, the MRI contrast agent using is at present divided into two classes: opaque contrast medium T 1with negative contrast medium T 2.They are respectively by strengthening the 1/T of regional area 1or 1/T 2relaxivity reaches picture signal and strengthens the effect that picture brightens or picture is dimmed.But under different scanning pulse train, for same contrast agent, the picture signal that can not simultaneously reach strengthens picture and brightens and the dimmed effect of picture.Although for example opaque contrast medium Gd-DTPA has T simultaneously 1and T 2radiography effect, but T 1radiography effect is better than T 2radiography effect, negative contrast medium SPIO is contrary.The T simultaneously having had in order to realize a kind of contrast agent 1and T 2radiography effect, the unpredictable danger of avoiding the dissimilar contrast agent of multiple injection to bring to patient.The present invention has developed a kind of method of preparing mix type contrast agent material by hydro-thermal reaction.The method has the advantages that preparation is simple, reaction condition is gentle, be easy to control.The mix type contrast agent material of preparing can reach good T simultaneously 1and T 2radiography effect is the novel contrast agent material of a class.
Summary of the invention
The object of the present invention is to provide one to there is T 1, T 2the preparation method of the mix type contrast agent of radiography function, the method is to do template with double end parents organic molecule, under the condition existing at aromatic acid, a kind of mix type contrast agent that blending rare earth ion and VI B～VIII B family ion are being prepared in steam pressure system.Mix type contrast agent material prepared by the present invention has Nano Particle and good T 1, T 2radiography effect.
The invention provides one and there is T 1, T 2the preparation method of the mix type contrast agent of radiography function, the method comprises the steps:
(1) by a kind of double end parents' organic formwork molecular melting in solvent, ultrasonic at 30～50 DEG C it is fully dissolved;
(2) aromatic acid, rare earth chloride and VI B～VIII B family chloride are slowly added in above-mentioned (1) solution, continue ultrasonic until obtain the solution of homogeneous transparent;
(3) clear solution obtaining in (2) is added in hydrothermal reaction kettle, at 70～150 DEG C of reaction 24～72h, obtain granule precipitate;
(4) granule precipitate organic solvent washing step (3) being obtained is removed unreacting material;
(5) solid obtaining in (4) is put into 60～80 DEG C of backflow 24h of organic solvent to remove double end parents organic formwork molecule;
(6), finally by the product organic solvent washing in (5), in 40 DEG C～200 DEG C vacuum dryings, obtain mix type contrast agent.
Provided by the invention have a T 1, T 2the preparation method of the mix type contrast agent of radiography function, in step (1), described double end parents' organic formwork molecule is polyether surfactant; Described polyether surfactant is one or more in polyoxyethylene and polyoxypropylene block copolymers Pluronic F127, Pluronic F108, Pluronic P123, Pluronic P103, Pluronic P104, Pluronic P105, Pluronic P85, Pluronic P65.
Provided by the invention have a T 1, T 2the preparation method of the mix type contrast agent of radiography function, in step (1), described solvent is one or both in secondary deionized water, ethanol.
Provided by the invention have a T 1, T 2the preparation method of the mix type contrast agent of radiography function, in step (2), described aromatic acid is one or more in p-phthalic acid, diaminourea p-phthalic acid, Trimesic acid, M-phthalic acid; Cation in described rare earth chloride can be one or more in praseodymium (Pr), neodymium (Nd), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutecium (Lu); Cation in described VI B～VIII B chloride can be one or more in ferrum (Fe), cobalt (Co), nickel (Ni), manganese (Mn).
Provided by the invention have a T 1, T 2the preparation method of the mix type contrast agent of radiography function, in step (4), described organic solvent is ethanol water miscible agent (mixed proportion is 4:1～1:1), N, N-diethylformamide, N, dinethylformamide, N,N-dimethylacetamide, N, N-dimethyl propylene amide, N, N-diethyl acetamide, N, one or more in N-diethyl propionic acid amide..
Provided by the invention have a T 1, T 2the preparation method of the mix type contrast agent of radiography function, in step (5), described organic solvent is the one in methanol, ethanol, methanol-water miscible agent (mixed proportion is 5:1～1:5), ethanol water miscible agent (mixed proportion is 5:1～1:5).
Provided by the invention have a T 1, T 2the preparation method of the mix type contrast agent of radiography function, in step (6), described organic solvent is the one in methanol, ethanol, methanol-water miscible agent (mixed proportion is 5:1～1:5), ethanol water miscible agent (mixed proportion is 5:1～1:5).
The present invention compared with prior art has following excellent beneficial effect:
Mix type contrast agent material prepared by the present invention has Nano Particle and good T 1, T 2radiography effect.
Brief description of the drawings
Fig. 1 is by the rare-earth cation Gd of regulation and control different proportion in the embodiment of the present invention 1 3+with VIII B cation Fe 3+, the mix type contrast agent Gd of preparation 80fe 20transmission electron microscope picture;
Fig. 2 is by the rare-earth cation Gd of regulation and control different proportion in the embodiment of the present invention 2 3+with VIII B cation Fe 3+, the mix type contrast agent Gd of preparation 20fe 80transmission electron microscope picture;
Fig. 3 is by the rare-earth cation Gd of regulation and control different proportion in the embodiment of the present invention 1 3+with VIII B cation Fe 3+, the mix type contrast agent Gd of preparation 80fe 20mR image;
Fig. 4 is by the rare-earth cation Gd of regulation and control different proportion in the embodiment of the present invention 2 3+with VIII B cation Fe 3+, the mix type contrast agent Gd of preparation 20fe 80mR image.
Detailed description of the invention
The following examples will be further described the present invention, but not thereby limiting the invention.
Embodiment 1
1,0.718g F127 is dissolved in 25mL secondary deionized water, the ultrasonic 30min of 50 degree fully dissolves it.
2,0.189g p-phthalic acid, 0.160g gadolinium trichloride and 0.041g Iron(III) chloride hexahydrate are slowly added in above-mentioned solution,, continue ultrasonic until obtain the solution of homogeneous transparent.
3, the clear solution obtaining in 2 is added in hydrothermal reaction kettle, at 150 DEG C of reaction 24h.
4, after reaction finishes, by the centrifugal reactant liquor secondary deionized water reactant liquor that goes.
5, then crude product is washed to twice with DMF again, to remove unreacting material.
6, the solid obtaining in 5 is put into ethanol 80 degree 1d to remove F127.
7, finally product washing with alcohol 3 times of F127 will be removed in 6.After 60 DEG C of vacuum drying 24h, obtain target product Gd 80fe 20.Embodiment 2
1,0.718g F127 is dissolved in 25mL secondary deionized water, the ultrasonic 30min of 50 degree fully dissolves it.
2,0.189g p-phthalic acid, 0.04g gadolinium trichloride and 0.164g Iron(III) chloride hexahydrate are slowly added in above-mentioned solution,, continue ultrasonic until obtain the solution of homogeneous transparent.
3, the clear solution obtaining in 2 is added in hydrothermal reaction kettle, at 150 DEG C of reaction 24h.
4, after reaction finishes, by the centrifugal reactant liquor secondary deionized water reactant liquor that goes.
5, then crude product is washed to twice with DMF again, to remove unreacting material.
6, the solid obtaining in 5 is put into ethanol 80 degree 1d to remove F127.
7, finally product washing with alcohol 3 times of F127 will be removed in 6.After 60 DEG C of vacuum drying 24h, obtain target product Gd 20fe 80.
Embodiment 3-6
Embodiment 3-6 and embodiment 1～2 difference see the following form:
T 1, T 2contrast agent structure and MR property representation
The mix type contrast agent Gd that adopts MinMR-60 that JEM-2000EX transmission electron microscope that Japanese JEOL Electronics Co., Ltd produces and Shanghai Niumai Electronic Technology Co., Ltd. produce and NMI20 magnetic resonance device to prepare the present invention 80fe 20and Gd 20fe 80particle diameter pattern and contrast agent imaging characterize, result is as shown in Fig. 1～4.
The mix type contrast agent Gd of the preparation of the embodiment of the present invention 1～2 shown in Fig. 1～4 80fe 20and Gd 20fe 80dispersion of materials is all very even, and the similar acicular texture of the former similar Fructus Mori structure the latter, size is respectively in 70nm(short end), 150nm(long end) and 140nm(short end), 890nm(long end).In addition compared with matched group ferroso-ferric oxide, along with the increase of contrast concentration, the T of two kinds of mix type contrast agent 1weighted imaging, brightness increases gradually, T 2weighted imaging, brightness reduces gradually.And matched group ferroso-ferric oxide, along with the increase of contrast concentration, T 1weighted imaging brightness there is not variation, T substantially 2weighted imaging brightness reduces gradually, and this explanation mix type contrast agent has T simultaneously 1and T 2radiography effect.

Claims (10)

1.一种具有T1、T2造影功能的掺混型造影剂的制备方法，其特征在于：该方法包括如下步骤：1. A method for preparing a blended contrast agent with T1 and T2 imaging functions, characterized in that: the method comprises the steps of: （1）将一种双头双亲有机模板分子溶解于溶剂中，在30～50℃下超声使其充分溶解；(1) Dissolving a double-headed amphiphilic organic template molecule in a solvent and ultrasonically dissolving it at 30-50°C; （2）将芳香酸、稀土氯化物及ⅥB～ⅧB族氯化物慢慢加入上述（1）溶液中，继续超声直到得到均匀透明的溶液；(2) Slowly add aromatic acids, rare earth chlorides and group VIB~ⅧB chlorides into the above solution (1), and continue to sonicate until a uniform and transparent solution is obtained; （3）将（2）中得到的透明溶液加入水热反应釜中，在70～150℃反应24～72h，得到颗粒析出物；(3) Add the transparent solution obtained in (2) into a hydrothermal reaction kettle, and react at 70-150°C for 24-72 hours to obtain granular precipitates; （4）将步骤（3）得到的颗粒析出物用有机溶剂洗涤除去未反应原料；(4) washing the precipitated particles obtained in step (3) with an organic solvent to remove unreacted raw materials; （5）将（4）中得到的固体放入有机溶剂中60～80℃回流24h以除掉双头双亲有机模板分子；(5) Put the solid obtained in (4) into an organic solvent and reflux at 60-80°C for 24 hours to remove the double-headed amphiphilic organic template molecules; （6）最后将（5）中的产物用有机溶剂洗涤，于40℃～200℃真空干燥，得到掺混型造影剂。(6) Finally, the product in (5) is washed with an organic solvent, and dried in vacuum at 40°C to 200°C to obtain a blended contrast agent. 2.按照权利要求1所述具有T1、T2造影功能的掺混型造影剂的制备方法，其特征在于：步骤（1）中，所述双头双亲有机模板分子为聚醚类表面活性剂。2. According to the preparation method of the blended contrast agent with T 1 and T 2 imaging functions according to claim 1, it is characterized in that: in step (1), the double-headed amphiphilic organic template molecule is a polyether surface active agent. 3.按照权利要求2所述具有T1、T2造影功能的掺混型造影剂的制备方法，其特征在于：步骤（1）中，所述聚醚类表面活性剂为聚氧乙烯与聚氧丙烯嵌段共聚物Pluronic F127、Pluronic F108、Pluronic P123、Pluronic P103、Pluronic P104、Pluronic P105、Pluronic P85、Pluronic P65中的一种或两种以上。3. According to the preparation method of the blended contrast agent with T 1 and T 2 contrast functions according to claim 2, it is characterized in that: in step (1), the polyether surfactant is polyoxyethylene and poly One or more of the oxypropylene block copolymers Pluronic F127, Pluronic F108, Pluronic P123, Pluronic P103, Pluronic P104, Pluronic P105, Pluronic P85, Pluronic P65. 4.按照权利要求1所述具有T1、T2造影功能的掺混型造影剂的制备方法，其特征在于：步骤（1）中，所述溶剂为二次去离子水、乙醇中的一种或两种。4. According to the preparation method of the blended contrast agent with T 1 and T 2 contrast functions according to claim 1, it is characterized in that: in step (1), the solvent is one of secondary deionized water and ethanol one or two. 5.按照权利要求1所述具有T1、T2造影功能的掺混型造影剂的制备方法，其特征在于：步骤（2）中，所述芳香酸为对苯二甲酸、二氨基对苯二甲酸、均三苯甲酸、间苯二甲酸中的一种或两种以上；5. According to the preparation method of the blended contrast agent with T 1 and T 2 contrast functions according to claim 1, it is characterized in that: in step (2), the aromatic acid is terephthalic acid, diaminop-phenylene One or more of dicarboxylic acid, m-tribenzoic acid, and isophthalic acid; 步骤（2）中，所述稀土氯化物中的阳离子可为镨（Pr）、钕（Nd）、钐（Sm）、铕（Eu）、钆（Gd）、铽（Tb）、镝（Dy）、钬（Ho）、铒（Er）、铥（Tm）、镱（Yb）、镥（Lu）中的一种或两种以上；In step (2), the cations in the rare earth chloride can be praseodymium (Pr), neodymium (Nd), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy) One or more of holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu); 步骤（2）中，所述ⅥB～ⅧB族氯化物中的阳离子可为铁（Fe）、钴(Co)、镍（Ni）、锰（Mn）中的一种或两种以上；In step (2), the cations in the group VIB-VIIIB chlorides can be one or more of iron (Fe), cobalt (Co), nickel (Ni), and manganese (Mn); 步骤（2）中，所述稀土氯化物和ⅥB～ⅧB族氯化物中阳离子的物质量比为4:1～1:4；In step (2), the mass ratio of the cations in the rare earth chlorides to the group VIB-VIIIB chlorides is 4:1-1:4; 步骤（2）中，所述芳香酸在反应液中的浓度范围为：1～4mM。In step (2), the concentration range of the aromatic acid in the reaction liquid is: 1-4mM. 6.按照权利要求1所述具有T1、T2造影功能的掺混型造影剂的制备方法，其特征在于：步骤（4）中，所述有机溶剂为乙醇水混溶剂、N,N-二乙基甲酰胺、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N,N-二甲基丙酰胺、N,N-二乙基乙酰胺、N,N-二乙基丙酰胺中的一种或两种以上。6. According to the preparation method of the blended contrast agent with T 1 and T 2 imaging functions according to claim 1, it is characterized in that: in step (4), the organic solvent is an ethanol water-miscible solvent, N,N- Diethylformamide, N,N-Dimethylformamide, N,N-Dimethylacetamide, N,N-Dimethylpropionamide, N,N-Diethylacetamide, N,N- One or more than two kinds of diethylpropionamide. 7.按照权利要求6所述具有T1、T2造影功能的掺混型造影剂的制备方法，其特征在于：所述乙醇水混溶剂的比例为4:1～1:1。7 . The method for preparing the blended contrast agent with T 1 and T 2 imaging functions according to claim 6 , wherein the ratio of the ethanol-water miscible solvent is 4:1˜1:1. 8.按照权利要求1所述具有T1、T2造影功能的掺混型造影剂的制备方法，其特征在于：步骤（5）中，所述有机溶剂为甲醇、乙醇、甲醇水混溶剂、乙醇水混溶剂中的一种。8. According to the preparation method of the blended contrast agent with T 1 and T 2 imaging functions according to claim 1, it is characterized in that: in step (5), the organic solvent is methanol, ethanol, methanol water-miscible solvent, One of the ethanol water miscible solvents. 9.按照权利要求1所述具有T1、T2造影功能的掺混型造影剂的制备方法，其特征在于：步骤（6）中，所述有机溶剂为甲醇、乙醇、甲醇水混溶剂、乙醇水混溶剂中的一种。9. According to the preparation method of the blended contrast agent with T 1 and T 2 imaging functions according to claim 1, it is characterized in that: in step (6), the organic solvent is methanol, ethanol, methanol water-miscible solvent, One of the ethanol water miscible solvents. 10.按照权利要求8或9所述具有T1、T2造影功能的掺混型造影剂的制备方法，其特征在于：所述甲醇水混溶剂的比例为5:1～1:5；所述乙醇水混溶剂的比例为5:1～1:5。10. According to claim 8 or 9, the preparation method of the blended contrast agent with T 1 and T 2 contrast functions, characterized in that: the ratio of the methanol-water miscible solvent is 5:1-1:5; The ratio of the ethanol-water miscible solvent is 5:1-1:5.
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