CN105084392A - Manganese potassium ferricyanide crystalline nanoparticles and preparation method for nuclear magnetic resonance contrast agent using same - Google Patents
Manganese potassium ferricyanide crystalline nanoparticles and preparation method for nuclear magnetic resonance contrast agent using same Download PDFInfo
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Abstract
Manganese potassium ferricyanide crystalline nanoparticles and a preparation method for nuclear magnetic resonance contrast agent using the same. The invention relates to compound crystalline nanoparticles represented by the molecular formula KMn[Fe(CN)6](H2O)n and a preparation method for nuclear magnetic resonance contrast agent using the same, wherein n=0-4. The compound crystalline nanoparticles can be used for nuclear magnetic resonance contrast agent.
Description
Technical field
The present invention relates to a kind of molecular formula is KMn [Fe (CN)
6] (H
2o)
nthe preparation method of compound crystal nanometer and mri contrast agent thereof, wherein n=0-4, this compound crystal nano-particle solution can be used as mri contrast agent.
Background technology
The present invention relates to a kind of molecular formula is KMn [Fe (CN)
6] (H
2o)
nthe preparation method of compound crystal nanometer and mri contrast agent thereof, wherein n=0-4, this compound crystal nano-particle solution can be used as mri contrast agent.
Summary of the invention
The invention provides a kind of molecular formula is KMn [Fe (CN)
6] (H
2o)
nthe preparation method of compound crystal nanometer and mri contrast agent thereof, this compound crystal nano-particle solution can be used as mri contrast agent.
1, molecular formula is KMn [Fe (CN)
6] (H
2o)
n, the wherein preparation of the compound crystal of n=0-4, mainly comprises the following steps:
With the ferrous complexing ion [Fe (CN) of six cyanogen
6]
4-with divalent manganesetion Mn
2+by hybrid reaction, obtain crystallization, by this Crystallization Separation out after, at 50 DEG C of freeze-day with constant temperature to constant weight, obtaining molecular formula is KMn [Fe (CN)
6] (H
2o)
n, the wherein compound crystal of n=0-4.
The wherein ferrous complexing ion [Fe (CN) of six cyanogen
6]
4-, by [Fe (CN) 6]
4-concentration is 0.01-0.50 mole
-calculate, by dissolve in the following aqueous solution containing [Fe (CN)
6]
4-compound dissolution in the aqueous citric acid solution of 0.1%-20% (weight), be called A1, or be dissolved in 0.1%-20% (weight) aqueous tartaric acid solution and be called A2, or be dissolved in lactic acid
:a3 is called in the lactic acid aqueous solution of the volume ratio 1: 1-20 of water;
Wherein divalent manganesetion Mn
2+, by Mn
2+concentration is 0.01-0.50 mole of calculating, by dissolve in the following aqueous solution containing Mn
2+compound dissolution in the aqueous citric acid solution of 0.1%-20% (weight), be called B1, or be dissolved in 0.1%-20% (weight) aqueous tartaric acid solution and be called B2, or be dissolved in lactic acid: be called B3 in the lactic acid aqueous solution of the volume ratio 1: 1-20 of water;
A1 to be poured in B1 to obtain into C1, or A1 to be poured in B2 to obtain into C2, or A1 to be poured in B3 to obtain into C3;
A2 to be poured in B1 to obtain into D1, or A2 to be poured in B2 to obtain into D2, or A2 to be poured in B3 to obtain into D3;
A3 to be poured in B1 to obtain into E1, or A3 to be poured in B2 to obtain into E1, or A3 to be poured in B3 to obtain into E3.
Above-mentioned hybrid mode obtains CI, C2, C3, D1, D2, D3, E1, E2, E3 crystallization, and after separating, within the scope of 45 DEG C-65 DEG C, freeze-day with constant temperature is to constant weight, and obtaining its molecular formula is KMn [Fe (CN)
6] (H
2o)
n, wherein n=0-4, crystalline particle particle diameter is between 0.1-120 micron, and the x-ray diffractogram of powder of crystallization is shown in Fig. 1.
2, molecular formula is KMn [Fe (CN)
6] (H
2o)
n, wherein the preparation of the compound crystal nanoparticle of n=0-4 mainly comprises the following steps:
Be KMn [Fe (CN) by molecular formula
6] (H
2o) n, wherein the compound crystal corrosion of n=0.-4 is in the aqueous solution of N.F,USP MANNITOL, meglumine, polyvinylpyrrolidone at formula, or corrosion is in the aqueous solution of N.F,USP MANNITOL, meglumine, polyvinylpyrrolidone, nicotinic acid, Zonon D, halfcystine at formula, or corrosion is in the aqueous solution of N.F,USP MANNITOL, meglumine, polyvinylpyrrolidone, nicotinic acid, Zonon D at formula, or corrosion is in the aqueous solution of N.F,USP MANNITOL, meglumine, polyvinylpyrrolidone, nicotinic acid, halfcystine at formula, or corrosion is in the aqueous solution of N.F,USP MANNITOL, meglumine, polyvinylpyrrolidone, Zonon D, halfcystine at formula, or corrosion is in N.F,USP MANNITOL, meglumine, polyvinylpyrrolidone, cigarette aqueous acid at formula, or corrosion is in the aqueous solution of N.F,USP MANNITOL, meglumine, polyvinylpyrrolidone, Zonon D at formula, or corrosion is in the aqueous solution of N.F,USP MANNITOL, meglumine, polyvinylpyrrolidone, halfcystine at formula, it is transparent that above-mentioned corrosion process need constantly be stirred to solution, in above-mentioned corrosion process, polyvinylpyrrolidone can use chitosan, or available dextran, or available carboxyl dextran, or available dextran, or available Sensor Chip CM 5, or available polyoxyethylene glycol substitutes, in above-mentioned each formula, the consumption of composition is respectively: N.F,USP MANNITOL consumption is 3-20% (weight), meglumine consumption is 1.0%-25% (weight), polyvinylpyrrolidone consumption is 1.5%-20% (weight), chitosan dosage is 1.5%-15% (weight), dextran consumption is 1.5%-15% (weight), carboxyl dextran consumption is 1.5%-15% (weight), dextran consumption is 1.5%-15% (weight), Sensor Chip CM 5 consumption is 1.5%-15% (weight), polyoxyethylene glycol consumption is 1.5%-15% (weight), nicotinic acid consumption is 0.01-5.0% (weight), Zonon D consumption is 0.01-5.0% (weight), bladder propylhomoserin consumption is 0.01%-5.0% (weight), in said process, continue after each composition adds to stir 0.5-24 hour, the molecular formula forming stable transparent is KMn [Fe (CN)
6] (H
2o)
nthe nano-particle solution of compound crystal.Divalent manganesetion content is between 0.1-200mM, and PH is between 7.60-12.50, and Nanoparticle Size is between 0.1nm-200nm.
3, molecular formula is KMn [Fe (CN)
6] (H
2o)
n, wherein the preparation of the nanoparticle contrast agent of the compound crystal of n=0-4 mainly comprises the following steps:
Be KMn [Fe (CN) by prepared molecular formula
6] (H
2o)
nwherein the nano-particle solution of the compound crystal of n=0-4 is mixed with the concentration containing manganese 2-50mM, through 0.22 μ n millipore filtration sterile filtration, aseptic subpackaged in cillin bottle, i.e. obtained liquid Manganese hexacyanoferrate potassium crystallization nano-NMR contrast medium, can use by injection for intravenous;
Be KMn [Fe (CN) by prepared molecular formula
6] (H
2o)
nwherein the nano-particle solution of the compound crystal of n=0-4 is mixed with the concentration containing manganese 2-50mM, through 0.22 μm of millipore filtration sterile filtration, gained filtrate, by aseptic spray chilling vacuum-drying or vacuum freeze-drying method process, obtains dry powder, aseptic subpackaged in cillin bottle, i.e. obtained solid-state Manganese hexacyanoferrate potassium crystallization nano-NMR contrast medium, use front water for injection or injection normal saline dilution, be made into the concentration containing manganese 2-50mM, can use by injection for intravenous.
4, molecular formula is KMn [Fe (CN)
6] (H
2o)
n, wherein the nanoparticle mri contrast agent of the compound crystal of n=0-4 shows for rat liver magnetic resonance imaging result:
The remarkable blast of T1 contrastographic picture, signal enhancement value is more than 2 times of blank signal, sees Fig. 4, Fig. 5;
Big white mouse after radiography experiment is raised 2 weeks, period its outward appearance and behavior no abnormality seen.
Accompanying drawing explanation
Fig. 1 is the molecular formula prepared by the embodiment of the present invention 1 is KMn [Fe (CN)
6] (H
2o)
n, the wherein compound crystal of n=0-4, its powder x-ray diffraction figure is Fig. 1.
Fig. 2 is the molecular formula prepared by the embodiment of the present invention 2 is KMn [Fe (CN)
6] (H
2o)
n, the wherein nano-particle solution of the compound crystal of n=0-4, through transmission electron microscope observing to nanoparticle be Fig. 2, nano particle diameter is between 40-70nm.
Fig. 3 is the molecular formula prepared by the embodiment of the present invention 2 is KMn [Fe (CN)
6] (H
2o)
n, the wherein nano-particle solution of the compound crystal of n=0-4, doing ultimate analysis energy spectrogram through transmission electron microscope is Fig. 3, and the ratio recording potassium, manganese and iron is about 1: 1: 1.
Fig. 4 is the molecular formula prepared by the embodiment of the present invention 2 is KMn [Fe (CN)
6] (H
2o)
nthe wherein nano-particle solution of the compound crystal of n=0-4, through being prepared into the intravenous injection sample containing manganese 10mM, by the dosage of 1ml/300g by before in tail vein injection to big white mouse body, do magnetic resonance imaging, obtain magnetic resonance imaging T1 image and the signal value of the rat liver before injection.
Fig. 5 is the molecular formula prepared by the embodiment of the present invention 2 is KMn [Fe (CN)
6] (H
2o)
nthe wherein nano-particle solution of the compound crystal of n=0-4, through being prepared into the intravenous injection sample containing bivalent manganese 10mM, by the dosage of 1ml/300g by tail vein injection in big white mouse body, do magnetic resonance imaging, the magnetic resonance imaging T1 image of rat liver and signal value when must inject latter 20 minutes.
Embodiment
Embodiment 1:
KMn [Fe (CN)
6] (H
2o)
n, the preparation of the wherein Manganese hexacyanoferrate potassium crystallization of n=0-4
Take 1.0561 grams of K
4[Fe (CN)
6] 3 (H
2o) put into 100 ml beakers, add acid: the lactic acid aqueous solution 25ml of the volume ratio 1: 10 of water dissolves completely, be called for short sample A; Take 0.9896 gram of MnCl
24H
2o puts into 100 ml beakers, adds lactic acid: the lactic acid aqueous solution 25ml of the volume ratio 1: 10 of water dissolves completely, is called for short sample B; A sample is poured in the beaker of B sample, beaker mouth is sealed with sealing compound, under lucifuge, room temperature leaves standstill and produces a large amount of fine crystalline after 12 hours, with 0.22-0.45 μm of filtering with microporous membrane, crystallize to that filtrate PH is unchanged by washed with de-ionized water, by the crystallization after cleaning, at 50 DEG C, freeze-day with constant temperature is to constant weight, and obtaining molecular formula is KMn [Fe (CN)
6] (H
2o)
n, the wherein Manganese hexacyanoferrate potassium crystallization of n=0-4, its x-ray diffractogram of powder is shown in Fig. 1.
Embodiment 2:
Molecular formula is KMn [Fe (CN)
6] (H
2o)
n, the preparation of the nanoparticle of the wherein Manganese hexacyanoferrate potassium crystallization of n=0-4
Take 8.50g N.F,USP MANNITOL, add water to 65ml, add meglumine 6.00g, nicotinic acid 0.0109g, Zonon D 0.0242g, halfcystine 0.0180g, polyvinylpyrrolidone 9.00g again, continuous stirring, and be progressively heated to 60 DEG C, maintain 60 DEG C and dissolve completely to polyvinylpyrrolidone, solution is that micro-Huang is transparent, and then be cooled to room temperature, be called for short sample A.
Taking molecular formula is KMn [Fe (CN)
6] (H
2o)
n, wherein the Manganese hexacyanoferrate crystallization 0.2734g of n=0-4 joins in sample A, and constantly stir, dissolve completely to this crystallization, solution is amber transparent, and continue stirring 12 hours, obtaining molecular formula is KMn [Fe (CN)
6] (H
2o)
n, the wherein Manganese hexacyanoferrate crystalline nanoparticles solution of n=0-4, is called for short sample B.The pH value recording sample B is 9.0; Nanoparticle equiblibrium mass distribution in the solution in transmission electron microscope observation to sample B, particle diameter, in 40-70nm scope, is shown in Fig. 2; Transmission electron microscope ultimate analysis power spectrum records potassium in sample B: manganese: the atomic ratio of iron is about 1: 1: 1, sees Fig. 3;
Embodiment 3:
Be KMn [Fe (CN) by molecular formula prepared in embodiment 2
6] (H
2o)
n, wherein the nano-particle solution sample B of the compound crystal of n=0-4 is mixed with the concentration containing manganese 10mM, through 0.22 μm of millipore filtration sterile filtration, aseptic subpackaged in cillin bottle, namely obtained liquid Manganese hexacyanoferrate potassium crystallization nano-NMR contrast medium, is called for short sample C, can use by injection for intravenous;
Embodiment 4:
Be KMn [Fe (CN) by molecular formula prepared in embodiment 2
6] (H
2o)
nwherein the nano-particle solution sample B of the compound crystal of n=0-4 is mixed with the concentration containing manganese 10mM, and through 0.22 μm of millipore filtration sterile filtration, gained filtrate is through sterile cryo vacuum drying treatment, obtain dry powder, aseptic subpackaged in cillin bottle, namely obtained solid-state Manganese hexacyanoferrate potassium crystallization nano-NMR contrast medium, is called for short sample D, use front water for injection or injection normal saline dilution, be made into the concentration containing manganese 10mM, be called for short sample E, can use by injection for intravenous.
Embodiment 5:
By the sample C that obtains in embodiment 3 by the dosage of 1ml/300g by tail vein injection in big white mouse body, do magnetic resonance imaging experiment, record magnetic resonance imaging T1 image and the signal value of rat liver before injection sample C, see Fig. 4; The magnetic resonance imaging T1 image of rat liver and signal value when 20 minutes after injection sample C, be shown in Fig. 5.The remarkable blast of rat liver magnetic resonance imaging image after injection sample C, signal value is more than 2 times before injection sample C, and the big white mouse after injection sample C is raised 2 weeks, period big white mouse outward appearance and behavior no abnormal.
Claims (12)
1. a molecular formula is KMn [Fe (CN)
6] (H
2o)
nthe preparation method of compound crystal nanoparticle and mri contrast agent thereof, wherein n=0-4.
2. molecular formula is KMn [Fe (CN) according to claim 1
6] (H
2o)
ncompound crystal nanoparticle, its preparation process is that first to prepare molecular formula be KMn [Fe (CN)
6] (H
2o)
ncompound crystal, wherein n=0-4, then prepare molecular formula for KMn [Fe (CN) with this compound crystal
6] (H
2o)
ncompound crystal nanoparticle, wherein n=0-4.
3. molecular formula is KMn [Fe (CN) according to claim 2
6] (H
2o)
ncompound crystal, is characterized in that, with the ferrous complexing ion [Fe (CN) of six cyanogen
6]
4-with divalent manganesetion Mn
2+, by hybrid reaction, obtain crystallization, by this Crystallization Separation out after, at 50 DEG C of freeze-day with constant temperature to constant weight, obtaining molecular formula is KMn [Fe (CN)
6] (H
2o)
nthe crystallization of compound, wherein n=0-4.
4. ferrous complexing ion [Fe (CN) of six cyanogen according to claim 3
6]
4-, it is characterized in that, by [Fe (CN)
6]
4-concentration is 0.01-0.50 mole
-calculate, by dissolve in the following aqueous solution containing [Fe (CN)
6]
4-compound dissolution 0.1%-20% (weight) aqueous citric acid solution or be dissolved in 0.1%-20% (weight) aqueous tartaric acid solution or be dissolved in lactic acid: in the lactic acid aqueous solution of the volume ratio 1: 1-20 of water.
5. divalent manganesetion Mn according to claim 3
2+, it is characterized in that, by Mn
2+concentration is 0.01
-0.50 mole of calculating, by dissolve in the following aqueous solution containing Mn
2+compound dissolution 0.1%-20% (weight) aqueous citric acid solution or be dissolved in 0.1%-20% (weight) aqueous tartaric acid solution or be dissolved in lactic acid: in the lactic acid aqueous solution of the volume ratio 1: 1-20 of water.
6. molecular formula is KMn [Fe (CN) according to claim 3
6] (H
2o)
nthe crystallization of compound, the crystalline powder X-ray diffractogram of this compound is Fig. 1.
7. molecular formula is KMn [Fe (CN) according to claim 2
6] (H
2o)
nthe crystallization of compound, crystalline particle particle diameter is between 0.1-120 micron.
8., according to claim 3, be KMn [Fe (CN) by molecular formula
6] (H
2o)
nthe crystallization corrosion of compound is in the aqueous solution of N.F,USP MANNITOL, meglumine, polyvinylpyrrolidone at formula, or corrosion is in the aqueous solution of N.F,USP MANNITOL, meglumine, polyvinylpyrrolidone, nicotinic acid, Zonon D, halfcystine at formula, or corrosion is in the aqueous solution of N.F,USP MANNITOL, meglumine, polyvinylpyrrolidone, nicotinic acid, Zonon D at formula, or corrosion is in the aqueous solution of N.F,USP MANNITOL, meglumine, polyvinylpyrrolidone, nicotinic acid, halfcystine at formula, or corrosion is in the aqueous solution of N.F,USP MANNITOL, meglumine, polyvinylpyrrolidone, Zonon D, halfcystine at formula, or corrosion is in N.F,USP MANNITOL, meglumine, polyvinylpyrrolidone, cigarette aqueous acid at formula, or corrosion is in the aqueous solution of N.F,USP MANNITOL, meglumine, polyvinylpyrrolidone, Zonon D at formula, or corrosion is in the aqueous solution of N.F,USP MANNITOL, meglumine, polyvinylpyrrolidone, halfcystine at formula, it is transparent that above-mentioned corrosion process need constantly be stirred to solution, in above-mentioned dissolving or corrosion process, polyvinylpyrrolidone can use chitosan, or available dextran, or available carboxyl dextran, or available dextran, or available Sensor Chip CM 5, or available polyoxyethylene glycol substitutes, in above-mentioned each formula, the consumption of composition is respectively: N.F,USP MANNITOL consumption is 2-20% (weight), meglumine consumption is 1.0%-25% (weight), polyvinylpyrrolidone consumption is 1.5%-20% (weight), chitosan dosage is 1.5%-15% (weight), dextran consumption is 1.5%-15% (weight), carboxyl dextran consumption is 1.5%-15% (weight), dextran consumption is 1.5%-15% (weight), Sensor Chip CM 5 consumption is 1.5%-15% (weight), polyoxyethylene glycol consumption is 1.5%-15% (weight), nicotinic acid consumption is 0.01-5.0% (weight), Zonon D consumption is 0.01-5.0% (weight), halfcystine consumption is 0.01%
-5.0% (weight), in said process, continue after each composition adds to stir 0.5-36 hour, the molecular formula forming stable transparent is KMn [Fe (CN)
6] (H
2o)
nthe nano-particle solution of compound crystal.
9. nano-particle solution according to claim 8, divalent manganesetion content is between 0.1-400mM.
10. nano-particle solution according to claim 8, is characterized in that PH is between 7.60-12.50.
11. nano-particle solution according to claim 8, is characterized in that described Nanoparticle Size is between 0.1nm-200nm.
12. nano-particle solution according to claim 8, is characterized in that described nano-particle solution or its lyophilized powder can be used as mri contrast agent bulk drug used for intravenous injection.
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Cited By (4)
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| CN105079824A (en) * | 2014-05-19 | 2015-11-25 | 吴学文 | Hexacyano-metal complex nanoparticle of manganese and nuclear magnetic resonance contrast agent of nanoparticle |
| CN107343962A (en) * | 2016-05-04 | 2017-11-14 | 吴学文 | Prussian blue nano and its synthetic method |
| CN108017070A (en) * | 2017-12-18 | 2018-05-11 | 吴学文 | The synthesis of Manganese hexacyanoferrate potassium white crystals |
| CN109095477A (en) * | 2017-06-21 | 2018-12-28 | 吴学文 | The synthesis of Manganese hexacyanoferrate potassium crystallization |
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| US20130257378A1 (en) * | 2012-03-28 | 2013-10-03 | Yuhao Lu | Transition Metal Hexacyanoferrate Battery Cathode with Single Plateau Charge/Discharge Curve |
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| CN105016358A (en) * | 2014-04-30 | 2015-11-04 | 吴学文 | Manganese hexacyanoferrate nanocrystal and preparation method of nuclear magnetic resonance contrast medium of same |
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| US20130257378A1 (en) * | 2012-03-28 | 2013-10-03 | Yuhao Lu | Transition Metal Hexacyanoferrate Battery Cathode with Single Plateau Charge/Discharge Curve |
| CN103449477A (en) * | 2012-05-29 | 2013-12-18 | 顾世海 | Novel nanometer material contrast agent and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105079824A (en) * | 2014-05-19 | 2015-11-25 | 吴学文 | Hexacyano-metal complex nanoparticle of manganese and nuclear magnetic resonance contrast agent of nanoparticle |
| CN107343962A (en) * | 2016-05-04 | 2017-11-14 | 吴学文 | Prussian blue nano and its synthetic method |
| CN109095477A (en) * | 2017-06-21 | 2018-12-28 | 吴学文 | The synthesis of Manganese hexacyanoferrate potassium crystallization |
| CN108017070A (en) * | 2017-12-18 | 2018-05-11 | 吴学文 | The synthesis of Manganese hexacyanoferrate potassium white crystals |
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