CN108721650A - A kind of magnetic resonance contrast agent of the Prussian blue material of Gd2 O3 - Google Patents
A kind of magnetic resonance contrast agent of the Prussian blue material of Gd2 O3 Download PDFInfo
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- CN108721650A CN108721650A CN201710250149.9A CN201710250149A CN108721650A CN 108721650 A CN108721650 A CN 108721650A CN 201710250149 A CN201710250149 A CN 201710250149A CN 108721650 A CN108721650 A CN 108721650A
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- prussian blue
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/18—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes
- A61K49/1818—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles
- A61K49/1821—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles
- A61K49/1824—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles coated or functionalised nanoparticles
- A61K49/1827—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles coated or functionalised nanoparticles having a (super)(para)magnetic core, being a solid MRI-active material, e.g. magnetite, or composed of a plurality of MRI-active, organic agents, e.g. Gd-chelates, or nuclei, e.g. Eu3+, encapsulated or entrapped in the core of the coated or functionalised nanoparticle
- A61K49/183—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles coated or functionalised nanoparticles having a (super)(para)magnetic core, being a solid MRI-active material, e.g. magnetite, or composed of a plurality of MRI-active, organic agents, e.g. Gd-chelates, or nuclei, e.g. Eu3+, encapsulated or entrapped in the core of the coated or functionalised nanoparticle having a (super)(para)magnetic core coated or functionalised with an inorganic material or being composed of an inorganic material entrapping the MRI-active nucleus, e.g. silica core doped with a MRI-active nucleus
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Abstract
The present invention relates to a kind of preparation methods of the contrast agent of the Prussian blue material of Gd2 O3, and this method comprises the following steps：（1）Prepare mixed liquor：In carboxylic acid compound aqueous solution, the compound containing gadolinium atom is mixed with molysite, potassium ferrocyanide solution and obtains or in carboxylic acid compound aqueous solution, the compound containing gadolinium atom is mixed into acquisition with ferrous salt, potassium ferricyanide solution；（2）Whipping step at a certain temperature（1）The mixed liquor of preparation；（3）Separating step（2）The nano particle of the Prussian blue material of Gd2 O3 contained in solution, and rinse.Contrast agent material prepared by the present invention replaces the iron atom in Prussian blue material using gadolinium so that the toxicity of the contrast agent material is smaller, more satisfactory at shadow effect.And the preparation method can get the controllable nano particle of size.
Description
Technical field
The invention belongs to medical contrast medium technical fields, and in particular to a kind of magnetic resonance of the Prussian blue material of Gd2 O3 is made
The application of the preparation method of shadow agent and the material in gastrointestinal tract detection.
Background technology
Magnetic resonance imaging（MRI）It is one kind of fault imaging, it obtains electromagnetic signal using electromagnetic induction phenomenon from human body,
And human body information is reconstructed, carry out a kind of method of medical diagnosis on disease.It and x-ray tomography of electronic computer（CT）With
Positron emission tomography（PET）Compared to no ionization radiation injury, having higher soft tissue resolution capability and primary
The advantages that three-dimensional cross-sections are imaged, has been widely used in the diagnostic imaging of each internal organs of whole body.Contrast agents（Also referred to as：Contrast agent）'s
Reasonable employment can effectively improve the signal-to-noise ratio of " lesion with normal structure contrast/noise ratio " and image, to earlier, smaller
Ground finds lesion and shows that the overall picture (content, blood supply, the proximity relations of such as lesion) of lesion will have highly important value.
Contrast agent is that current mr techniques develop most rapid, most tempting one of field.Nineteen eighty-three Weinmann synthesizes
First magnetic resonance contrast agent Gd-DTPA, and the formal U.S. FDA that obtains ratified clinic in 1988, Gd-DTPA is broken to blood-brain barrier
Bad property disease (intracranial inflammation and tumour) and whole body other systems disease have exact diagnosis effect.Scientific research institution of various countries and manufacturer
The numerous and confused novel mr angiography agent for being actively developed exploitation and there is respective uniqueness to strengthen function, and obtain many breakthroughs.Has crowd at present
Mostly novel gadolinium class contrast agent, such as Gd-DOTA, Gd-HP-DOTA, Gd-DTPA-BM, Gd-BOPTA and Gd-EOB-DTPA it is successive on
City, in addition also Mn-DPDP, Ferric Ammonium Citrate and Superparamagnetic Iron Oxide（SPIOs）Contrast agent lists in succession.It can foretell,
Following nuclear magnetism contrast agent will likely be rich and varied as CT contrast agent, and clinician will be according to different needs and reinforcing
The ideal reliable contrast agent of purpose selection.
Currently, magnetic resonance imaging medical examination, is widely used to clinic, the approval of doctor and patient are obtained, and by
Year's harvest rapid growth trend, this makes the production and sales of MRI contrast agent also rapid growth year by year.External mr imaging technique
It carries out clinical diagnosis and has had reached certain scale, be used as conventional detection means to popularize for physical examination in developed countries such as America and Europes,
Other countries were expected to obtain more common of application as a kind of novel conventional detection means in several years, to the need of contrast agent
The amount of asking will be also continuously increased；With the development of domestic economy, hospital above county level gradually buys magnetic resonance imager, has driven magnetic
Resonance contrast agent demand increases rapidly.Whole world year contrast agent sales volume is more than 2,000,000,000 dollars at present, according to Business
The market intelligence of Communications Company shows that the average year in U.S. MR diagnosis contrast agents market increases
Long rate is 11.5%, to increase most swift and violent category in contrast agents market.In China, the growth in magnetic resonance contrast agents market
More powerful, average growth rate is more than 30%.
Gastrointestinal tract is the chief component of digestive system, is the major organs that the mankind obtain that energy sustains life.Stomach and intestine
The physiological structure in road is complicated, and enterogastric diseases are common diseases, occupy the second of chronic disease, the hair of alimentary tract cancer in China
Sick rate is very high, occupies fifty percent in the cancer of top ten list, and traditional diagnostic mode is basically used for the diagnosis of enterogastric diseases,
But these methods have many shortcomings, and gastroscope, colonoscopy Lesion Detection rate is very high, but checking process is complicated, and patient is very painful,
It need to anaesthetize, patient's receptance is low, and checking process needs the experience with doctor, is susceptible to detection leakage phenomenon；CT radiographies are current
The main means of gastrointestinal examination are carried out, but it changes detection simply by gastrointestinal tract anatomical structure, reaches to solid tumor
Diagnosis.To the early carcinomatous change just with metabolic function slight change, recall rate is not high；Secondly, the X- that CT radiographies use is penetrated
Line is 2% canceration pathogenic factor.Gastrointestinal disease inspection continuously improving derived from instrument these years is carried out with MRI, as one kind
New detection methods, MRI check have radiationless, and rate is high respectively for tissue, can check very subtle biochemistry, metabolic function side
The features such as variation (such as difference of cancer cell and normal cell water content) in face, the early detection of cancer can be carried out.
Presently commercially available more typical contrast agent is complex compound containing Gd, represents object：Gd-DTPA（Magnevist）, Gd classes make
Due to being not sufficiently stable in hydrochloric acid in gastric juice, signal stabilization is poor for shadow agent, is easy to decomposite toxic heavy metal Gd, is not yet approved for facing
Bed magnetic resonance contrast medium for gastrointestinal tract.Commercialized product is Fe agent at present, i.e.,：Ferroso-ferric oxide and Ferric Ammonium Citrate, both are clinical
All it is T2 contrast agent when use（Shadow）, need to use simultaneously with other contrast agent, diagnostic purpose can be reached, thus using by
To considerable restraint.There is presently no a kind of T1 to take orally magnetic resonance contrast agent listing.
Invention content
Both there are good contrasting effects the purpose of the present invention is to provide a kind of, while to low new of body dysfunction
Generation contrast agent, the magnetic resonance contrast agent of specially a kind of Prussian blue material of Gd2 O3.The contrast agent is with Prussian blue knot
Based on structure.
To achieve the above object, the present invention provides a kind of preparation side of the magnetic resonance contrast agent of the Prussian blue material of Gd2 O3
The reaction equation of method, this method is as follows：
Fe3++Gd3++[FeⅡ(CN)6]4-+ carboxylic acid compound → prussian blue nano particle；
Or
Fe2++Gd3++[FeⅢ(CN)6]4-+ carboxylic acid compound → prussian blue nano particle.
Specifically comprise the following steps：
（1）Prepare mixed liquor：In carboxylic acid compound aqueous solution, by the compound containing gadolinium atom and molysite, potassium ferrocyanide
Solution mixing obtains or in carboxylic acid compound aqueous solution, by the compound containing gadolinium atom and ferrous salt, potassium ferricyanide solution
Mixing obtains；
（2）Whipping step at a certain temperature（1）The mixed liquor of preparation；
（3）Separating step（2）The nano particle of the Prussian blue material of Gd2 O3 contained in solution, and rinse.
In the present invention, step 1）Described in carboxylic acid compound, including single carboxylic acid, polycarboxylic acid, various hydroxycarboxylic acids,
Or a combination thereof；It can specifically include acetic acid, ethanedioic acid, citric acid, tartaric acid, adipic acid, gluconic acid, or a combination thereof.
In the present invention, step 1）Described in molysite, ferrous salt, compound containing gadolinium atom be water soluble compound.Its
Molysite, ferrous salt, compound containing gadolinium atom are chloride, sulfate, nitrate, perchlorate or any combination thereof respectively
Salt, content range 10-4 mol/L~102Mol/L, first choice 10-3Mol/L ~ 10 mol/L, preferably 10-3 mol/L~0.1
mol/L。
In the present invention, step 2）The range of reaction temperature is 0 ~ 100 DEG C, 10 DEG C ~ 80 DEG C preferred, preferably 10 DEG C ~ 60
℃。
In the present invention, step 2）The stirring needs are vigorously stirred, to prevent particle of the nanoparticle aggregate at bigger.
In the present invention, step 3）The size of the nano particle of the Prussian blue material of the Gd2 O3 is about 10 ~ 150
Nm, gadolinium atom is with Gd3+It is entrained in Prussian blue material, content is 10% ~ 90%.
The preparation method of the contrast agent of the Prussian blue material of the Gd2 O3, preparation process is simple, and nano particle is big
Small controllable, imaging effect is excellent, high sensitivity, good biocompatibility, and the development and application to clinical video diagnostic technology have
Significance.
With reference to embodiments, it further illustrates the present invention, but the invention is not limited in these embodiments, Ren Heyi
Improvement according to the essence spirit of the present invention or replacement, still fall within range claimed in claims of the present invention.
Description of the drawings
Fig. 1 is rat stomach image under 0.5T in embodiment 4.
Fig. 2 is intestine in rats image under 0.5T in embodiment 4.
Fig. 3 is rat stomach image under 1.5T in embodiment 4.
Fig. 4 is intestine in rats image under 1.5T in embodiment 4.
Specific implementation mode
The following example 1-3 is the embodiment for preparing the compounds of this invention.
Embodiment 1.
Prepare mixed solution A：Contain 1.0 mmol/L ferric trichlorides and gadolinium trichloride in the solution（Ferric trichloride and trichlorine
The molar ratio for changing gadolinium is 9：1）And 0.5 mmol/L citric acid；Prepare mixed solution B：Contain 1.0 in the solution
Mmol/L potassium ferrocyanides K4[Fe(CN)6] and 0.5 mmol/L citric acid；20 mL mixed solution As are taken, are slowly added into mixed
Solution B is closed, is vigorously mixed at room temperature for 3 minutes；After centrifugation, with the mixed liquor (30 of water and acetone:70 V/V) punching
It washes 3 times, obtains the prussian blue nano material of Gd2 O3.X optical diffractions obtain cubical micro-structure (the three-dimensional knot of Fm3m
Structure), electron microscope analysis its be very well ordered cube chip architecture, pore-size distribution concentrates very much, and average nano aperture is about 14 to receive
Rice, is confirmed, Fe/Gd=19 in the nano material by elemental analysis:1.
Embodiment 2.
Prepare mixed solution C：Contain 1.0 mmol/L iron chloride and gadolinium trichloride in the solution（Iron chloride and gadolinium trichloride
Molar ratio be 6:4）And 0.5 mmol/L citric acid；Prepare mixed solution D：Contain 1.0 mmol/L's in the solution
Potassium ferricyanide K4[Fe(CN)6] and 0.5 mmol/L citric acid；In the dark, 20 mL mixed solution Cs and mixed solution are taken
D is mixed, and after shaking up, is exposed 30 minutes in the sun.Nano material gradually forms, solution in 5 to 10 minutes by
It is light green to become navy blue；After centrifugation, with the mixed liquor (30 of water and acetone:70 V/V) it rinses 3 times, it obtains gadolinium and mixes
Miscellaneous prussian blue nano material.Its micro-structure is extremely similar to A, is confirmed by elemental analysis, and Fe/Gd in the nano material=
4:1。
Embodiment 3.
Prepare mixed solution E：Contain 1.0 mmol/L frerrous chlorides and gadolinium trichloride in the solution（Frerrous chloride and trichlorine
The molar ratio for changing gadolinium is 5:5）And 0.5 mmol/L citric acid；Prepare mixed solution F：Contain 1.0 in the solution
The potassium ferricyanide K of mmol/L3[Fe(CN)6] and 0.5 mmol/L citric acid；20 mL mixed solution E are taken, are slowly added into mixed
Solution F is closed, is vigorously mixed at room temperature for 3 minutes；After centrifugation, with the mixed liquor (30 of water and acetone:70 V/V) punching
It washes 3 times, obtains the prussian blue nano material of Gd2 O3.Its micro-structure is extremely similar to A, is confirmed by elemental analysis, should
Fe/Gd=3 in nano material:1.
Embodiment 4：The application of the Prussian blue contrast agent material of Gd2 O3 gastrointestinal tract in rats.
Gastrointestinal tract imaging test under different magnetic field has been carried out using rat, by animal on an empty stomach 2 days, carried out with physiological saline
Gavage is tested for control group, is administration group with the Prussian blue contrast agent material gavage of Gd2 O3, observes imaging effect.
Fig. 1 is rat stomach imaging experiment under 0.5T, and the Prussian blue contrast agent material of description of test Gd2 O3 pours into stomach
Afterwards, T1 contrasting effects can be shown, after forty minutes, can be emptied from stomach.
Fig. 2 is intestine in rats imaging experiment under 0.5T, and the Prussian blue contrast agent material of description of test Gd2 O3 is after gavage
40min shows T1 effects into enteron aisle in enteron aisle.It is emptied substantially after 120min.
Fig. 3 is rat stomach imaging test under 1.5T, and the Prussian blue contrast agent material of description of test Gd2 O3 pours into stomach
After 10 min, T1 contrasting effects can be shown.
Fig. 4 is intestine in rats imaging experiment under 1.5T, and the Prussian blue contrast agent material of description of test Gd2 O3 is after gavage
40min shows T1 effects into enteron aisle in enteron aisle.
The Prussian blue nano material containing gadolinium (Gd3+) element of the present invention is not limited to such use, such material
Material and synthesis mode can be also used for medical imaging, drug carrier, medical diagnosis on disease and biologic medical research.
Claims (7)
1. a kind of preparation method of the magnetic resonance contrast agent of the Prussian blue material of Gd2 O3, this method comprises the following steps：
（1）Prepare mixed liquor：In carboxylic acid compound aqueous solution, by the compound containing gadolinium atom and molysite, potassium ferrocyanide
Solution mixing obtains or in carboxylic acid compound aqueous solution, by the compound containing gadolinium atom and ferrous salt, potassium ferricyanide solution
Mixing obtains；
（2）Whipping step at a certain temperature（1）The mixed liquor of preparation；
（3）Separating step（2）The nano particle of the Prussian blue material of Gd2 O3 contained in solution, and rinse.
2. a kind of step 1 of claim 1）Described in carboxylic acid compound, including single carboxylic acid, polycarboxylic acid, various hydroxyls
Carboxylic acid, or a combination thereof；It can specifically include acetic acid, ethanedioic acid, citric acid, tartaric acid, adipic acid, gluconic acid or its group
It closes.
3. a kind of step 1 of claim 1）Described in molysite, ferrous salt, compound containing gadolinium atom be water-soluble chemical combination
Object.
4. its molysite, ferrous salt, compound containing gadolinium atom are chloride, sulfate, nitrate, perchlorate respectively or its is any
The salt of combination, content range 10-4 mol/L~102Mol/L, first choice 10-3Mol/L ~ 10 mol/L, preferably 10-3 mol/L~
0.1 mol/L。
5. a kind of step 2 of claim 1）The range of reaction temperature is 0 ~ 100 DEG C, 10 DEG C ~ 80 DEG C, preferably 10 DEG C preferred
~60℃。
6. a kind of stirring needs of claim 1 are vigorously stirred, to prevent particle of the nanoparticle aggregate at bigger.
7. a kind of step 3 of claim 1）The size of the nano particle of the Prussian blue material of the Gd2 O3 is about 10 ~
150 nm, gadolinium atom is with Gd3+It is entrained in Prussian blue material, content is 10% ~ 90%.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103623435A (en) * | 2012-08-20 | 2014-03-12 | 苏州迈格锐意医药科技有限公司 | Nanometer magnetic resonance contrast material, nanometer magnetic resonance contrast agent and preparation method of nanometer magnetic resonance contrast agent |
| CN105963696A (en) * | 2016-05-05 | 2016-09-28 | 广西师范大学 | Preparation method and applications of targeting prussian blue nano particles |
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- 2017-04-17 CN CN201710250149.9A patent/CN108721650A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103623435A (en) * | 2012-08-20 | 2014-03-12 | 苏州迈格锐意医药科技有限公司 | Nanometer magnetic resonance contrast material, nanometer magnetic resonance contrast agent and preparation method of nanometer magnetic resonance contrast agent |
| CN105963696A (en) * | 2016-05-05 | 2016-09-28 | 广西师范大学 | Preparation method and applications of targeting prussian blue nano particles |
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