CN103894557B - The preparation method of functionalization golden nanometer particle visual under nuclear magnetic resonance and application - Google Patents
The preparation method of functionalization golden nanometer particle visual under nuclear magnetic resonance and application Download PDFInfo
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Abstract
The invention discloses under a kind of mr imaging technique can the preparation method of new function golden nanometer particle of video picture and application thereof.The present invention adopts the diethylene triamine pentaacetic acid of band sulfydryl to be trim with the Polyethylene Glycol of band sulfydryl, utilizes bonding action stable between Au-S key and reducing agent to prepare functionalization golden nanometer particle, by controlling functions golden nanometer particle and GdCl
3ratio chelating Gd
3+, and engage mPEG-SH, utilize hydrophilic and the bioaffinity of paramagnetism that Gd-DTPA complex is very strong and peg molecule, obtain particle diameter little, distribute homogeneous, can Magnetic Resonance Imaging, long circulating, good biocompatibility golden nanometer particle.This golden nanometer particle can be used for MRI vivo tracking graft at the intravital bio distribution of host and Survival, evaluates the effect caused by graft.The present invention provides new approach for the detection method of MRI vivo tracking graft and drug distribution.
Description
Technical field
The invention belongs to nano imaging diagnostic field, relate to a kind of preparation method and the application that can be used for the new function golden nanometer particle of nuclear magnetic resonance, utilize diethylene triamine pentaacetic acid (DTPA-SH) derivant of band sulfydryl and the Polyethylene Glycol (mPEG-SH) of band sulfydryl to be trim in particular to a kind of, sodium borohydride or sodium citrate are reducing agent and chelating Gd
3+prepare method and the application thereof of the functionalization golden nanometer particle of Novel magnetic resonance imaging.
Background technology
Golden nanometer particle has the character of unique optics, calorifics, electricity, magnetics and chemical aspect, by making it have the bioaffinity of good stability, small-size effect, skin effect, optical effect and uniqueness to the utilization of these character, making golden nanometer particle have all many-sides such as 2 and 3 dimensional organization new material at optical material, biological engineering, medicine, biosensor, catalysis industry, microelectronics industry and structure and there is important application.
Solution of gold nanoparticles is the aurosol of a kind of dispersed phase particles diameter between 1 ~ 150nm, belongs to heterogeneous heterogeneous system, and color is that Chinese red is to aubergine.Gold grain is rounded in the solution, edge-smoothing, complete, and boundary is fully aware of.The surface of golden nanometer particle is with layer of Au Cl
4 -negative charge, the negative charge between particle repels mutually, and interparticle spacing is constant, forms metastable state.But the H As time goes on, in aqueous solution
+also be adsorbed to golden nanometer particle surface gradually, the melanoma cells of particle, thus cause particle accumulation, form the nanoparticle that particle diameter is larger, gather to a certain degree, also can deposit.In long-time, keep stable in order to making the golden nanometer particle of preparation, usually the hydrophobic molecule of last layer to be modified at particle surface, as mercaptan, dendrimer, DNA and protein etc., not only can improve the stability of golden nanometer particle but also its functionalization can be made, thus be applied to the aspects such as molecular recognition, biological label, biological detection, medicine transmission, drug labelling, gene therapy, immunoassay.
Nuclear magnetic resonance (MRI) is a Non-Invasive medical imaging diagnosis technology powerful, can provide live body 3D rendering in real time from cell or molecular level.The development effect of the obvious Contrast-enhanced MRI of MRI contrast agent energy, the normal contrast agent Gd-DTPA(gadolinium-divinyl five amine acetic acid used at present), there is paramagnetism, be distributed in intercellular fluid, it mainly changes magnetic action and its relaxation time of Hydrogen Proton, shorten T1 and T2, the position that pathological changes and blood brain barrier can be made to be damaged produces high signal on T1 weighting picture, realizes enhancement purpose.The DTPA of the two sulfydryl of band can utilize bonding action stable between Au-S key, trim Gd-DTPA is connected to the surface of golden nanometer particle, thus makes golden nanometer particle have paramagnetism.Therefore, by modifying the paramagnetism on golden nanometer particle surface, golden nanometer particle not only can be made to have MRI image displaying function, the stability of golden nanometer particle can also be improved.
Polyethylene Glycol is the macromolecule with hydrophilic, compliance and bioaffinity, have that structure is simple, inexpensive, nontoxic, non-immunogenicity and terminal hydroxy group be easy to the advantages such as derivatization, be widely used for the field of medicaments such as multi-medicament preparation, Surface Modification of Medical Polymer Materials.Peg molecule is introduced on golden nanometer particle surface, macromolecule layer protective layer can be formed, for golden nanometer particle provides new spatial stability together with DTPA derivant.Meanwhile, the structural specificity of peg molecule makes liver reticuloendothelial system decline to some extent to golden nanometer particle Scavenging activity, residence time in extension body.
Summary of the invention
The preparation method of new function golden nanometer particle visual under the object of this invention is to provide a kind of nuclear magnetic resonance, can be used for MRI vivo tracking graft at the intravital bio distribution of host and Survival, or as biotransformation in the body of the real-time tracer drug of pharmaceutical carrier.
First the present invention by the DTPA derivant of synthesis containing two sulfydryl, utilizes the bonding action between Au-S key to prepare functionalized nano grain, complexation Gd
3+rejoin mPEG-SH, the new function golden nanometer particle that obtained MRI is visual.This nanoparticle can be used for MRI vivo tracking transplanted cells at the intravital bio distribution of host and Survival, hurtless measure, the effect of evaluation caused by graft intuitively, or as biotransformation in the body of the real-time tracer drug of pharmaceutical carrier, therefore have Clinical practice prospect extensively.
Provided by the present invention prepare Novel magnetic resonance imaging under the method for visual golden nanometer particle, first be for raw material with diethylene triamine pentaacetic acid (DTPA), react with mercaptoethylmaine and triethylamine, after reacting by heating, filter lyophilizing, obtain the DTPA derivant containing two sulfydryl; The DTPA derivant containing two sulfydryl is added, with NaBH in solution of gold nanoparticles
4or sodium citrate is reducing agent, low pressure evaporation and concentration, after filtration drying, obtains functionalization golden nanometer particle; Finally by the colloid solution of functionalization golden nanometer particle and GdCl
3reaction, by chelating Gd
3+the Polyethylene Glycol mPEG-SH of rear splicing tpae sulfydryl, obtaining can the new function golden nanometer particle of macrocyclic Magnetic Resonance Imaging.
Its principle is: synthesis containing the DTPA derivant of two sulfydryl, and is trim with mPEG-SH, utilizes bonding action stable between Au-S key and chemical preparation functionalization golden nanometer particle, and by itself and Gd
3+chelating, utilizes the paramagnetism that Gd-DTPA complex is very strong, obtains the new function golden nanometer particle that MRI is visual.
Concrete steps prepared by functionalization golden nanometer particle visual under a kind of nuclear magnetic resonance provided by the invention are as follows: the diethylene triamine pentaacetic acid (DTPA) of 2g adds 40mLN, dinethylformamide (DMF), is heated to 70 DEG C and makes it fully dissolve (solution 1).Be that 1:0.5 ~ 1:1 takes appropriate mercaptoethylmaine by the mass ratio of DTPA and mercaptoethylmaine, be that 1:1 ~ 1:2 takes appropriate triethylamine and adds after 30mLDMF fully dissolves and be added in solution 1 by the mass ratio of mercaptoethylmaine and triethylamine, stir at 60 ~ 80 DEG C of lower magnetic forces and spend the night, solution is cooled to ice bath after room temperature, treat the visible adularescent powder precipitation of naked eyes, filter, appropriate chloroformic solution is added to after filtrate being concentrated, to forming white depositions, filter, and wash with 50mL chloroformic solution, vacuum drying obtains the two sulfydryl DTPA derivant of white powder, with the chlorauric acid solution of 120mL methanol solution preparation 0.05 ~ 0.5mM, the ratio being 1:1 ~ 1:10 in gold chloride and the DTPA derivant mass ratio of two sulfydryl takes appropriate two sulfydryl DTPA derivant and is dissolved in 40mL methanol and 2mL acetum (solution 2), gradually solution 2 is added in chlorauric acid solution under the state stirred, this mixed solution color from yellow becomes orange, after 5 minutes, disposablely in this mixed solution again add appropriate borane reducing agent sodium hydride or sodium citrate (reducing agent/gold chloride molar ratio 1:1), room temperature magnetic agitation 0.5 ~ 3h low pressure evaporation and concentration, filter, precipitate uses 0.01mol/LHCl successively, water, washed with diethylether, functionalization golden nanometer particle is obtained after drying, 60mg functionalization golden nanometer particle powder adds the colloid solution of obtained golden nanometer particle in 30mL0.01mol/LNaOH solution, by functionalization golden nanometer particle and GdCl
3mass ratio be that 1:20 ~ 1:40 takes appropriate GdCl
3add under stirring at room temperature, low pressure evaporative removal part solution, then add isopyknic acetone with reactant liquor and precipitate, filter, dry black powder, then it is suspended in 10mL0.005 ~ 0.05mg/mLmPEG-SH again and stirs 1h, wherein the mass ratio of functionalization golden nanometer particle and mPEG-SH is 3:1 ~ 1:1, lyophilization (-54 DEG C, 36h), functionalization golden nanometer particle visual under obtaining Novel magnetic resonance imaging.
Different from other functionalization golden nanometer particles, the new function golden nanometer particle that the present invention is visual under obtaining a kind of nuclear magnetic resonance, its advantage is: can be used for MRI vivo tracking graft (comprising microencapsulation artificial cell transplantation field) at the intravital bio distribution of host and Survival, hurtless measure, the effect of evaluation caused by graft intuitively, or as biotransformation in the body of the real-time tracer drug of pharmaceutical carrier, and the step of synthesizing nano-particle is simple, easy to operate, good stability.The present invention extends new direction at nano imaging diagnostic field.
Accompanying drawing explanation
Fig. 1 is the structure chart of new function golden nanometer particle visual under nuclear magnetic resonance;
Fig. 2 is transmission electron microscope (TEM) figure of new function golden nanometer particle visual under nuclear magnetic resonance.
Detailed description of the invention
The preparation method of functionalization golden nanometer particle of the present invention is as follows
Step 1: the synthesis of two sulfydryl DTPA derivant
The diethylene triamine pentaacetic acid (DTPA) of 2g is added 40mLN, dinethylformamide (DMF), be heated to 70 DEG C and make it fully dissolve (solution 1).Be that 1:0.5 ~ 1:1 takes appropriate mercaptoethylmaine by the mass ratio of DTPA and mercaptoethylmaine, be that 1:1 ~ 1:2 takes appropriate triethylamine and adds after 30mLDMF fully dissolves and be added in solution 1 by the mass ratio of mercaptoethylmaine and triethylamine, stir at 60 ~ 80 DEG C of lower magnetic forces and spend the night, solution is cooled to ice bath after room temperature, treat the visible adularescent powder precipitation of naked eyes, filter, appropriate chloroformic solution is added to after filtrate being concentrated, to forming white depositions, filter, and wash with 50mL chloroformic solution, vacuum drying obtains the two sulfydryl DTPA derivant of white powder.
Step 2: the preparation of functionalization golden nanometer particle
With the chlorauric acid solution of 120mL methanol solution preparation 0.05 ~ 0.5mM, the ratio being 1:1 ~ 1:10 in gold chloride and the DTPA derivant mass ratio of two sulfydryl takes appropriate two sulfydryl DTPA derivant and is dissolved in 40mL methanol and 2mL acetum (solution 2), gradually solution 2 is added in chlorauric acid solution under the state stirred, this mixed solution color from yellow becomes orange, after 5 minutes, disposablely in this mixed solution again add appropriate borane reducing agent sodium hydride (sodium borohydride/gold chloride molar ratio 1:1), room temperature magnetic agitation 0.5 ~ 3h low pressure evaporation and concentration, filter, precipitate uses 0.01mol/LHCl successively, water, washed with diethylether, functionalization golden nanometer particle is obtained after drying.
Step 3: the preparation of functionalization golden nanometer particle
With the chlorauric acid solution of 120mL methanol solution preparation 0.05 ~ 0.5mM, the ratio being 1:1 ~ 1:10 in gold chloride and the DTPA derivant mass ratio of two sulfydryl takes appropriate two sulfydryl DTPA derivant and is dissolved in 40mL methanol and 2mL acetum (solution 2), gradually solution 2 is added in chlorauric acid solution under the state stirred, this mixed solution color from yellow becomes orange, after 5 minutes, disposablely in this mixed solution again add appropriate reducing agent sodium citrate (sodium citrate/gold chloride molar ratio 1:1), room temperature magnetic agitation 0.5 ~ 3h low pressure evaporation and concentration, filter, precipitate uses 0.01mol/LHCl successively, water, washed with diethylether, functionalization golden nanometer particle is obtained after drying.
Step 4: functionalization golden nanometer particle chelating Gd
3+the preparation of complex
60mg functionalization golden nanometer particle powder adds the colloid solution of obtained golden nanometer particle in 30mL0.01mol/LNaOH solution, by functionalization golden nanometer particle and GdCl
3mass ratio be that 1:20 ~ 1:40 takes appropriate GdCl
3add under stirring at room temperature, low pressure evaporative removal part solution, then add isopyknic acetone with reactant liquor and precipitate, filter, dry, obtain functionalization golden nanometer particle chelating Gd
3+complex.
Step 5: functionalization golden nanometer particle engages the preparation of mPEG-SH complex
By functionalization golden nanometer particle chelating Gd
3+the black powder of complex is 3:1 ~ 1:1 by the mass ratio of itself and mPEG-SH, again stirring at normal temperature 1h in 10mL0.005 ~ 0.05mg/mLmPEG-SH is suspended in, lyophilization (-54 DEG C, 36h), new function golden nanometer particle visual under obtaining nuclear magnetic resonance.
The new function golden nanometer particle finally obtained is see Fig. 1 and Fig. 2.
Claims (7)
1. the preparation method of functionalization golden nanometer particle visual under a nuclear magnetic resonance, it is characterized in that being prepared by following process: first with diethylene triamine pentaacetic acid DTPA for raw material, react with mercaptoethylmaine and triethylamine, filter lyophilizing after reacting by heating, obtain the DTPA derivant containing two sulfydryl; The DTPA derivant containing two sulfydryl is added, with NaBH in chlorauric acid solution
4or sodium citrate is reducing agent, low pressure evaporation and concentration, after filtration drying, obtains functionalization golden nanometer particle; Again by the colloid solution of functionalization golden nanometer particle and GdCl
3reaction, by chelating Gd
3+after, the Polyethylene Glycol mPEG-SH of splicing tpae sulfydryl, functionalization golden nanometer particle visual under obtaining Novel magnetic resonance imaging.
2. preparation method according to claim 1, is characterized in that: described diethylene triamine pentaacetic acid and the mass ratio of mercaptoethylmaine are 1:0.5 ~ 1:1, and the mass ratio of mercaptoethylmaine and triethylamine is 1:1 ~ 1:2, and reaction temperature is 60 ~ 80 DEG C.
3. preparation method according to claim 1, it is characterized in that: the thing mass concentration of the chlorauric acid solution used in functionalization golden nanometer particle preparation process is 0.05 ~ 0.5mM, gold chloride is 1:1 ~ 1:10 with the mass ratio of two sulfydryl DTPA, the molar ratio of borane reducing agent sodium hydride or sodium citrate and gold chloride is 1:1, response time is 0.5 ~ 3h, and reaction temperature is room temperature.
4. preparation method according to claim 1, is characterized in that: functionalization golden nanometer particle and GdCl
3volume ratio be 1:20 ~ 1:40, for precipitating acetone consumption and the reactant liquor equal-volume of golden nanometer particle in reaction system, the response time is 0.5 ~ 3h, and reaction temperature is room temperature.
5. preparation method according to claim 1, is characterized in that: the mass ratio of described functionalization golden nanometer particle and mPEG-SH is 3:1 ~ 1:1, and the molecular weight of described mPEG-SH is 5000, and concentration is 0.005 ~ 0.05mg/mL.
6. the functionalization golden nanometer particle that obtains of preparation method according to claim 1, its application comprises: for MRI vivo tracking graft at the intravital bio distribution of host and Survival, or as biotransformation in the body of the real-time tracer drug of pharmaceutical carrier.
7. the preparation method of functionalization golden nanometer particle visual under a nuclear magnetic resonance, it is characterized in that: concrete steps are as follows: the diethylene triamine pentaacetic acid (DTPA) of 2g adds 40mLN, dinethylformamide (DMF), is heated to 70 DEG C and makes it fully dissolve, obtain solution 1; Be that 1:0.5 ~ 1:1 takes appropriate mercaptoethylmaine by the mass ratio of DTPA and mercaptoethylmaine, be that 1:1 ~ 1:2 takes appropriate triethylamine and adds after 30mLDMF fully dissolves and be added in solution 1 by the mass ratio of mercaptoethylmaine and triethylamine, stir at 60 ~ 80 DEG C of lower magnetic forces and spend the night, solution is cooled to ice bath after room temperature, treat the visible adularescent powder precipitation of naked eyes, filter, appropriate chloroformic solution is added to after filtrate being concentrated, to forming white depositions, filter, and wash with 50mL chloroformic solution, vacuum drying obtains the two sulfydryl DTPA derivant of white powder;
With the chlorauric acid solution of 120mL methanol solution preparation 0.05 ~ 0.5mM, the ratio being 1:1 ~ 1:10 in gold chloride and the DTPA derivant mass ratio of two sulfydryl takes appropriate two sulfydryl DTPA derivant and is dissolved in 40mL methanol and 2mL acetum obtains solution 2, gradually solution 2 is added in chlorauric acid solution under the state stirred, this mixed solution color from yellow becomes orange, after 5 minutes, disposablely in this mixed solution again add appropriate borane reducing agent sodium hydride or sodium citrate, wherein reducing agent and gold chloride molar ratio are 1:1, room temperature magnetic agitation 0.5 ~ 3h low pressure evaporation and concentration, filter, precipitate uses 0.01mol/LHCl successively, water, washed with diethylether, functionalization golden nanometer particle is obtained after drying,
60mg functionalization golden nanometer particle powder adds the colloid solution of obtained golden nanometer particle in 30mL0.01mol/LNaOH solution, by functionalization golden nanometer particle and GdCl
3mass ratio be that 1:20 ~ 1:40 takes appropriate GdCl
3add under stirring at room temperature, low pressure evaporative removal part solution, then add isopyknic acetone with reactant liquor and precipitate, filter, dry black powder; Then it is suspended in 10mL0.005 ~ 0.05mg/mLmPEG-SH again and stirs 1h, wherein the mass ratio of functionalization golden nanometer particle and mPEG-SH is 3:1 ~ 1:1, at-54 DEG C of lyophilization 36h, functionalization golden nanometer particle visual under obtaining Novel magnetic resonance imaging.
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| CN101549161A (en) * | 2009-05-13 | 2009-10-07 | 中南大学 | Liver, spleen specific positive magnetic nuclear resonance contrast agent and method of preparing the same |
| CN101745124A (en) * | 2010-01-21 | 2010-06-23 | 上海纳米技术及应用国家工程研究中心有限公司 | Gadolinium-containing silicon dioxide nanosphere magnetic resonance contrast agent and preparation method thereof |
| CN103079642A (en) * | 2010-07-16 | 2013-05-01 | 丹麦科技大学 | Nanoparticle-guided radiotherapy |
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| CN101549161A (en) * | 2009-05-13 | 2009-10-07 | 中南大学 | Liver, spleen specific positive magnetic nuclear resonance contrast agent and method of preparing the same |
| CN101745124A (en) * | 2010-01-21 | 2010-06-23 | 上海纳米技术及应用国家工程研究中心有限公司 | Gadolinium-containing silicon dioxide nanosphere magnetic resonance contrast agent and preparation method thereof |
| CN103079642A (en) * | 2010-07-16 | 2013-05-01 | 丹麦科技大学 | Nanoparticle-guided radiotherapy |
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