CN101890173A - Preparation method of magnetic resonance imaging contrast agent of magnetic water-soluble chitosan - Google Patents
Preparation method of magnetic resonance imaging contrast agent of magnetic water-soluble chitosan Download PDFInfo
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- CN101890173A CN101890173A CN 201010229022 CN201010229022A CN101890173A CN 101890173 A CN101890173 A CN 101890173A CN 201010229022 CN201010229022 CN 201010229022 CN 201010229022 A CN201010229022 A CN 201010229022A CN 101890173 A CN101890173 A CN 101890173A
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Abstract
The invention discloses a magnetic resonance imaging contrast agent of magnetic water-soluble chitosan and a preparation method thereof. The magnetic resonance imaging contrast agent of magnetic water-soluble chitosan consists of nano ferroferric oxide particles and water-soluble narrow molecular-weight oligomeric chitosan. The method comprises the following steps of: firstly, degrading chitosan into the water-soluble narrow molecular-weight oligomeric chitosan; adding a paramagnetic metallic inorganic salt; hydrolyzing by utilizing the paramagnetic metallic inorganic salt under an alkali condition; in situ making magnetic nano particles generated in the water-soluble narrow molecular-weight oligomeric chitosan; and carrying out magnetic separation and drying to obtain the magnetic resonance imaging contrast agent of the magnetic water-soluble chitosan. The preparation method has strong operability, wide application range, low cost and high yield, needs simple equipment and is suitable for mass production and industrial application. The magnetic resonance imaging contrast agent has certain target, appropriate in vivo residence time, high relaxation efficiency and small toxicity.
Description
Technical field
The present invention relates to the mr imaging technique field, relate in particular to a kind of preparation method of magnetic water-soluble chitosan nuclear magnetic resonance contrast medium.
Background technology
(magnetic resonance imaging is to utilize the influence of organism different tissues outside magnetic field to produce different resonance signals down to come the new technique of imaging MRI), is one of detection means the strongest in the current clinical diagnosis in nuclear magnetic resonance.Most important component is the MRI contrast medium in the MRI technology, in order to strengthen the magnetic resonance signal contrast between normal and the pathological tissues, need use the MRI contrast medium above 30% MRI inspection in the world at present.The MRI contrast medium is some paramagnetisms and superparamagnetism material, and studying more at present is superparamagnetism MRI contrast medium and water solublity MRI contrast medium.Superparamagnetism MRI contrast medium is a kind of to have unique crystal structures Fe
3O
4Be the particular iron magnetisable material of main component, comprise the microminiature Superparamagnetic Iron Oxide of parcels such as the Superparamagnetic Iron Oxide of microminiature Superparamagnetic Iron Oxide, the little aggressiveness of monocrystalline ferrum oxide, liposome and albumin, glucosan, polystyrene, monoclonal antibody etc.Have ferrum oxide colloid injection AMI-25 (FeridexIV), SHU-555A (Resovist), GastrOmark (Advanebd Magnetics), microminiature colloid of iron oxide AMI-227 (Ferumoxtran), NC100150 (Clariscan), the oral gastrointestinal tract contrast medium that have entered clinical practice have AMI-121 (Ferumoxil) and OMP (Obdoscan) etc.Water solublity paramagnetism MRI contrast medium is made up of paramagnetic metal ion and part, and metal ion is mainly Fe
2+, Fe
3+, Mn
2+, Gd
3+And Dy
3+, part is mainly many many carboxylations of ammonia compounds, as diethylenetriamine pentaacetic acid (DTPA), 1,4,7, and 10-tetraazacyclododecanand-1,4,7,10-tetraacethyl (DOTA) and ethylenediaminetetraacetic acid (EDTA) and their derivant.What entered clinical practice has a Gd-DTPA (magnevist, Magnevist), Gd-DTPA-BMA (gadolinium diamidogen, Omniscan), (gadolinium is for alcohol, Prohance), Gd-DOTA (Dotarem) and Gd-DO3A-butrol (Gadobutrol) etc. for Gd-DO3A-HP.
Chitosan is a kind of natural cationic polysaccharide that chitin obtains through deacetylation; have degradability, good film property, excellent biological compatibility and certain excellent properties such as antibiotic and antitumor; be widely used in industries such as medicine, food, chemical industry, environmental protection, have the good reputation of omnipotent polysaccharide.The degree of polymerization is that 6～12 narrow molecular-weight chitosan has good water-solubility, wait with Albumin (human blood serum). that to transport proteic binding ability strong, have multi-efficiencies such as cancer-resisting, angiocardiopathy preventing, raising body immune function, promotion bifidus factor propagation, thereby can be applicable to the medical imaging field.
This method will have the holdup time in certain targeting and the suitable body by preparing with narrow molecular-weight oligo-chitosan coated magnetic nanoparticle, relaxation efficient height, novel nuclear magnetic resonance contrast medium that toxicity is little.It is advantageous that: (1) used chitosan is the oligo-chitosan of narrow molecular-weight, good water solubility; (2) carbohydrate molecule has recognition reaction to Different Organs tissue and focus, improves corresponding selectivity; (3) have certain targeting, can arrive the body disease tissue by carrying medicament, improve therapeutic efficiency; (4) processing and preparing technology is simple, and equipment requirements is low, is easy to processing.
Summary of the invention
The purpose of this invention is to provide a kind of novel NMR (Nuclear Magnetic Resonance)-imaging contrast medium and preparation method thereof, improved relaxation efficient, prolonged the intravital relaxation time, and improvement has reduced toxic and side effects to the selectivity of Different Organs tissue or focus.
The present invention is as follows with the method that the narrow molecular-weight oligo-chitosan modified magnetic nanoparticle of good water solubility prepares the nuclear magnetic resonance contrast medium:
(1) takes by weighing the chitosan of certain mass in reaction vessel, the volume fraction that adds certain volume is the acetic acid solution of 0.01%-10%, the ratio of chitosan and acetic acid solution (quality: be 1 volume): 0.01-100 wherein, stirring the mass fraction that adds certain volume down is the hydrogen peroxide of 5%-30%, wherein the ratio of chitosan and hydrogen peroxide solution (quality: be 1 volume): 0.01-100; The solution of gained is carried out microwave treatment, and wherein microwave treatment conditions is that microwave power is 500-1000w, and temperature is 60-120 ℃, and microwave treatment time is 30-120min; Regulator solution pH adds solvent precipitation and goes out solid to neutral, the reuse organic solvent washing, and vacuum drying promptly gets water solublity narrow molecular-weight oligo-chitosan, and wherein said solvent is ethanol, methanol, acetone etc., and wherein said organic solvent is ether, petroleum ether etc.
(2) in reaction vessel; certain mass above-mentioned prepared water solublity narrow molecular-weight oligo-chitosan be dissolved in that to make its concentration in the deionized water of certain volume be 0.05-0.2g/mL; (ratio of chitosan and divalent iron salt and trivalent iron salt mixture is 400g: 1-10mol to add a certain amount of divalent iron salt and trivalent iron salt again in reaction system; wherein the mol ratio of the iron ion of divalent iron salt and trivalent iron salt is 1: 0.5～5; under the drying nitrogen protection; dropwise drip aqueous slkali; stirring reaction is 2～5 hours under 40～60 ℃ condition; carrying out magnetic after reaction finishes separates; obtain black solid; 40～60 ℃ of following vacuum dryings 24～48 hours; promptly get the magnetic water-soluble chitosan, wherein the aqueous slkali of Di Jiaing can be KOH; NaOH; Ba (OH)
2Solution.
Divalent iron salt described in the present invention and trivalent iron salt can be FeCl
24H
2O, FeCl
36H
2O, FeSO
47H
2O or anhydrous FeCl
3Etc. a series of iron salt.
The present invention compared with prior art has following remarkable advantage:
(1) chitosan is the renewable green resource of natural high yield, has excellent biological compatibility and degradability, and self is nontoxic, and the narrow molecular-weight oligo-chitosan good water solubility of using.(2) product has certain targeting, can selectively distribute in tissue or organ, effectively raises image contrast.(3) operation and equipment needed thereby are simple, and be with low cost, is easy to accomplish scale production.
Description of drawings:
Fig. 1 is the Fourier transform infrared spectroscopy figure of the magnetic water-soluble chitosan nuclear magnetic resonance contrast medium of embodiment 1 gained;
Fig. 2 is the NMR (Nuclear Magnetic Resonance) imaging comparison diagram of the magnetic water-soluble chitosan nuclear magnetic resonance contrast medium of embodiment 1 gained;
Fig. 3 is the transmission electron microscope photo of the magnetic water-soluble chitosan nuclear magnetic resonance contrast medium of embodiment 1 gained.
Concrete embodiment:
Example 1
Take by weighing the commercially available chitosan of 100g in reaction vessel, adding 1000mL volume fraction is 0.5% acetic acid solution, and adding 250mL mass fraction is 30% hydrogen peroxide under stirring, microwave reaction 60min, regulate pH to neutral, add ethanol and separate out solid, the washing of reuse ether, vacuum drying, promptly get water solublity narrow molecular-weight oligo-chitosan, mean molecule quantity is 1460, and the degree of polymerization is 8, molecular weight distributing index (DPI or M
w/ M
n)=1.01-1.05.
In 500 ml flasks, add synthetic water solublity narrow molecular-weight oligo-chitosan 20g, add FeSO
47H
2O 30g, anhydrous FeCl
330g adds 350 ml deionized water.Under the drying nitrogen protection, dropwise drip NaOH solution, stirring reaction is 2～5 hours under 40～60 ℃ condition; carrying out magnetic after reaction finishes separates; obtain black solid,, promptly get the magnetic water-soluble chitosan 40～60 ℃ of following vacuum dryings 24～48 hours.
Fig. 1 is the Fourier transform infrared spectroscopy figure of the magnetic water-soluble chitosan nuclear magnetic resonance contrast medium of embodiment 1 gained, (a) is the infrared spectrum of ferroso-ferric oxide among the figure, (b) being the infrared spectrum of water-soluble chitosan, (c) is the infrared spectrum of magnetic water-soluble chitosan.By contrast as can be known, successfully synthesized the magnetic water-soluble chitosan.
Fig. 2 is the NMR (Nuclear Magnetic Resonance) imaging comparison diagram of the magnetic water-soluble chitosan nuclear magnetic resonance contrast medium of embodiment 1 gained.Along with the increase of ferroso-ferric oxide content, the signal intensity of NMR (Nuclear Magnetic Resonance) imaging comparison diagram increases gradually as seen from the figure.Illustrate that this coordination compound can be used as good " nuclear magnetic resonance contrast medium " and uses.
Fig. 3 is the transmission electron microscope photo of the magnetic water-soluble chitosan nuclear magnetic resonance contrast medium of embodiment 1 gained.As seen from the figure, the magnetic nano-particle particle diameter is approximately 5nm, is evenly distributed in the chitosan.
Example 2
Take by weighing the commercially available chitosan of 100g in reaction vessel, adding 1000mL volume fraction is 0.5% acetic acid solution, and adding 250mL mass fraction is 30% hydrogen peroxide under stirring, microwave reaction 30min, regulate pH to neutral, add ethanol and separate out solid, the washing of reuse ether, vacuum drying, promptly get water solublity narrow molecular-weight oligo-chitosan, mean molecule quantity is 1980, and the degree of polymerization is 11, molecular weight distributing index (DPI or M
w/ M
n)=1.01-1.05.
In 500 ml flasks, add synthetic water solublity narrow molecular-weight oligo-chitosan 20g, add FeSO
47H
2O 30g, anhydrous FeCl
330g adds 350 ml deionized water.Under the drying nitrogen protection, dropwise drip NaOH solution, stirring reaction is 2～5 hours under 40～60 ℃ condition; carrying out magnetic after reaction finishes separates; obtain black solid,, promptly get the magnetic water-soluble chitosan 40～60 ℃ of following vacuum dryings 24～48 hours.
Example 3
Take by weighing the commercially available chitosan of 100g in reaction vessel, adding 1000mL volume fraction is 0.5% acetic acid solution, and adding 250mL mass fraction is 30% hydrogen peroxide under stirring, microwave reaction 90min, regulate pH to neutral, add ethanol and separate out solid, the washing of reuse ether, vacuum drying, promptly get water solublity narrow molecular-weight oligo-chitosan, mean molecule quantity is 1020, and the degree of polymerization is 6, molecular weight distributing index (DPI or M
w/ M
n)=1.01-1.05.
In 500 ml flasks, add synthetic water solublity narrow molecular-weight oligo-chitosan 20g, add FeSO
47H
2O 30g, anhydrous FeCl
330g adds 350 ml deionized water.Under the drying nitrogen protection, dropwise drip NaOH solution, stirring reaction is 2～5 hours under 40～60 ℃ condition; carrying out magnetic after reaction finishes separates; obtain black solid,, promptly get the magnetic water-soluble chitosan 40～60 ℃ of following vacuum dryings 24～48 hours.
Example 4
Take by weighing the commercially available chitosan of 100g in reaction vessel, adding 1000mL volume fraction is 0.5% acetic acid solution, and adding 250mL mass fraction is 30% hydrogen peroxide under stirring, microwave reaction 90min, regulate pH to neutral, add ethanol and separate out solid, the washing of reuse ether, vacuum drying, promptly get water solublity narrow molecular-weight oligo-chitosan, mean molecule quantity is 1020, and the degree of polymerization is 6, molecular weight distributing index (DPI or M
w/ M
n)=1.01-1.05.
In 500 ml flasks, add synthetic water solublity narrow molecular-weight oligo-chitosan 20g, add FeCl
24H
2O 10g, FeCl
36H
2O 25g adds 350 ml deionized water.Under the drying nitrogen protection, dropwise drip NaOH solution, stirring reaction is 2～5 hours under 40～60 ℃ condition; carrying out magnetic after reaction finishes separates; obtain black solid,, promptly get the magnetic water-soluble chitosan 40～60 ℃ of following vacuum dryings 24～48 hours.
Example 5
Take by weighing the commercially available chitosan of 100g in reaction vessel, adding 1000mL volume fraction is 0.5% acetic acid solution, and adding 250mL mass fraction is 30% hydrogen peroxide under stirring, microwave reaction 30min, regulate pH to neutral, add ethanol and separate out solid, the washing of reuse ether, vacuum drying, promptly get water solublity narrow molecular-weight oligo-chitosan, mean molecule quantity is 1980, and the degree of polymerization is 11, molecular weight distributing index (DPI or M
w/ M
n)=1.01-1.05.
In 500 ml flasks, add synthetic water solublity narrow molecular-weight oligo-chitosan 30g, add FeCl
24H
2O 10g, FeCl
36H
2O 25g adds 350 ml deionized water.Under drying nitrogen protection, dropwise drip KOH solution, stirring reaction is 2～5 hours under 40～60 ℃ condition, carries out magnetic after reaction finishes and separates, and obtains black solid, 40～60 ℃ of following vacuum dryings 24～48 hours, promptly gets the magnetic water-soluble chitosan.
Example 6
Take by weighing the commercially available chitosan of 100g in reaction vessel, adding 1000mL volume fraction is 0.5% acetic acid solution, and adding 250mL mass fraction is 30% hydrogen peroxide under stirring, microwave reaction 60min, regulate pH to neutral, add ethanol and separate out solid, the washing of reuse ether, vacuum drying, promptly get water solublity narrow molecular-weight oligo-chitosan, mean molecule quantity is 1460, and the degree of polymerization is 8, molecular weight distributing index (DPI or M
w/ M
n)=1.01-1.05.
In 500 ml flasks, add synthetic water solublity narrow molecular-weight oligo-chitosan 40g, add FeCl
24H
2O 10g, FeCl
36H
2O 25g adds 350 ml deionized water.Under drying nitrogen protection, dropwise drip KOH solution, stirring reaction is 2～5 hours under 40～60 ℃ condition, carries out magnetic after reaction finishes and separates, and obtains black solid, 40～60 ℃ of following vacuum dryings 24～48 hours, promptly gets the magnetic water-soluble chitosan.
Claims (2)
1. the preparation method of magnetic water-soluble chitosan nuclear magnetic resonance contrast medium is characterized in that carrying out according to following step:
(1) takes by weighing the chitosan of certain mass, the volume fraction that adds certain volume is the acetic acid solution of 0.01%-10%, wherein the ratio of chitosan and acetic acid solution counts 1 with quality and volume ratio: 0.01-100, stirring the mass fraction that adds certain volume down is the hydrogen peroxide of 5%-30%, and wherein the ratio of chitosan and hydrogen peroxide solution counts 1 with quality and volume ratio: 0.01-100; The solution of gained is carried out microwave treatment, and wherein microwave treatment conditions is that microwave power is 500-1000w, and temperature is 60-120 ℃, and microwave treatment time is 30-120min; Regulator solution pH adds solvent precipitation and goes out solid to neutral, the reuse organic solvent washing, and vacuum drying promptly gets water solublity narrow molecular-weight oligo-chitosan, and wherein said solvent is ethanol, methanol, acetone, and wherein said organic solvent is ether, petroleum ether;
(2) in reaction vessel; certain mass above-mentioned prepared water solublity narrow molecular-weight oligo-chitosan be dissolved in that to make its concentration in the deionized water of certain volume be 0.05-0.2g/mL; in reaction system, add a certain amount of divalent iron salt and trivalent iron salt again; wherein the ratio of chitosan and divalent iron salt and trivalent iron salt mixture is 400g: 1-10mol; wherein the mol ratio of the iron ion of divalent iron salt and trivalent iron salt is 1: 0.5～5; under the drying nitrogen protection; dropwise drip aqueous slkali; stirring reaction is 2～5 hours under 40～60 ℃ condition; carrying out magnetic after reaction finishes separates; obtain black solid; 40～60 ℃ of following vacuum dryings 24～48 hours; promptly get the magnetic water-soluble chitosan, wherein the aqueous slkali of Di Jiaing can be KOH; NaOH; Ba (OH)
2Solution.
2. the preparation method of magnetic water-soluble chitosan nuclear magnetic resonance contrast medium according to claim 1 is characterized in that wherein said divalent iron salt and trivalent iron salt can be FeCl
24H
2O, FeCl
36H
2O, FeSO
47H
2O or anhydrous FeCl
3
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Cited By (4)
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| CN106727691A (en) * | 2016-12-21 | 2017-05-31 | 湖北工程学院 | For antitumor medicine composition and preparation method thereof, parenteral solution |
| CN108888780A (en) * | 2018-06-25 | 2018-11-27 | 浙江理工大学 | A kind of superparamagnetic carboxyl chitosan/Fe3O4The preparation method of particle Micelle-like Nano-structure of Two |
| CN109603765A (en) * | 2018-12-14 | 2019-04-12 | 陕西师范大学 | A kind of chitosan oligomer magnetic bead, preparation method and applications |
| CN114306650A (en) * | 2022-01-21 | 2022-04-12 | 南方医科大学 | Magnetic ferroferric oxide nanoparticles and preparation method and application thereof |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106727691A (en) * | 2016-12-21 | 2017-05-31 | 湖北工程学院 | For antitumor medicine composition and preparation method thereof, parenteral solution |
| CN108888780A (en) * | 2018-06-25 | 2018-11-27 | 浙江理工大学 | A kind of superparamagnetic carboxyl chitosan/Fe3O4The preparation method of particle Micelle-like Nano-structure of Two |
| CN108888780B (en) * | 2018-06-25 | 2021-06-29 | 浙江理工大学 | Superparamagnetic carboxylated chitosan/Fe3O4Method for preparing particle nano aggregate |
| CN109603765A (en) * | 2018-12-14 | 2019-04-12 | 陕西师范大学 | A kind of chitosan oligomer magnetic bead, preparation method and applications |
| CN109603765B (en) * | 2018-12-14 | 2021-07-16 | 陕西师范大学 | Magnetic bead of chitosan oligosaccharide, preparation method and application thereof |
| CN114306650A (en) * | 2022-01-21 | 2022-04-12 | 南方医科大学 | Magnetic ferroferric oxide nanoparticles and preparation method and application thereof |
| CN114306650B (en) * | 2022-01-21 | 2022-12-06 | 南方医科大学 | Magnetic ferroferric oxide nanoparticles and preparation method and application thereof |
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