CN103007303A - Core-shell type tri-modal nano contrast agent as well as preparation method and application thereof - Google Patents
Core-shell type tri-modal nano contrast agent as well as preparation method and application thereof Download PDFInfo
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- CN103007303A CN103007303A CN2012105532617A CN201210553261A CN103007303A CN 103007303 A CN103007303 A CN 103007303A CN 2012105532617 A CN2012105532617 A CN 2012105532617A CN 201210553261 A CN201210553261 A CN 201210553261A CN 103007303 A CN103007303 A CN 103007303A
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Abstract
The invention discloses a core-shell type tri-modal nano contrast agent, which comprises a metal nano-cluster inner core, wherein the metal nano-cluster inner core comprises metal, human serum albumin and a paramagnetic metal ion coordination compound shell; the human serum albumin is assembled outside the metal to serve as a protecting group; and the paramagnetic metal ion coordination compound shell is used for coating the metal nano-cluster inner core, the shell comprises a chelating agent and paramagnetic metal ions, the chelating agent is connected with the human serum albumin in a covalent manner through an amido bond, and the paramagnetic metal ions are combined on the chelating agent in a coordination manner. The invention further provides a preparation method of the core-shell type tri-modal nano contrast agent.
Description
Technical field
The present invention relates to multi-modal image technology, be specifically related to a kind of MRI/NIR/CT three mode nano-contrast agents, its preparation method and application.
Background technology
Tumor is one of important diseases that threatens human health, and the early diagnosis and therapy of tumor is the key that improves life in patients and cure rate.At present, the molecular imaging technology that is applied to tumor has optical image technology, CT(CT Scan) imaging technique, MRI(nuclear magnetic resonance) molecular imaging technology, ultrasound molecular image technology, SPECT technology, PET technology and NIR(near-infrared fluorescence imaging) technology.But single molecular image technology exists the defective that self is difficult to overcome, and is difficult to obtain quantitative information at human body especially deep tissue such as fluorescence imaging, and the CT imaging technique lacks selectively targeted contrast medium, and ultra sonic imaging resolution is low etc.Single imaging mode is not enough to obtain fully tumor information, unites and uses the different kinds of molecules imaging technique can realize having complementary advantages each other, and comprehensively information is provided for clarifying a diagnosis more accurately.
Multi-modal molecular image technology is injected body with the molecular probe that has simultaneously multiple phenomenon function, by the detection of derived techniques, obtains the diseased region much information, and multi-modal molecular image probe synthetic be the core of multi-modal molecular image technology.The research that develops into multi-modal molecular image probe of nanotechnology provides good platform, in conjunction with multiple imaging function, is applied to the early stage diagnosis and detection of tumor by nano-carrier.In the prior art, in a large number the molecular image probes based on nanotechnology obtain exploitation, such as quantum dot, magnetic nano-particle, near infrared fluorescent dye and radio-labelled molecule, but still can not well solve the problem of the low problem of tumor-targeting and bio-toxicity.
The human serum albumin is the highest protein of content in the blood plasma, the Nano medication as carrier with the human serum albumin has appearred in the prior art, this Nano medication has good biocompatibility and tumor-targeting, reason be tumor cell to the human serum albumin as the Nano medication of carrier have select phagocytic, the tumor cell metabolism is vigorous, can initiatively absorb the human serum albumin in the Nano medication, be the self-energy source, and normal cell is without above-mentioned effect, therefore, the nanoparticle take the human serum albumin as carrier has potential value in the tumor-targeting problem that solves multi-modal nano imaging probe.
In addition, diameter is easily engulfed by reticuloendothelial system (RES) greater than the nanoparticle of 20nm, causes its efficient and sensitivity.Diameter is cleared up less than the lymphsystem in the easy body of the nanoparticle of 10nm, and bio-toxicity reduces.Simultaneously, diameter is realized the direct targeting of tumor less than the easier high osmosis of utilizing vascular system in the tumor tissues of the nanoparticle of 10nm, can not only enter diseased organ or tissue, can also enter tumor cell inside.Therefore, diameter all has potential value less than the multi-modal nano imaging probe of 10nm on solution tumor-targeting problem and bio-toxicity problem.
Summary of the invention
The present invention is intended to solve above-mentioned problems of the prior art, one aspect of the present invention proposes a kind of core-shell type three mode nano-contrast agents, comprise: the metal nanometre cluster kernel, described metal nanometre cluster kernel comprises metal, and is assembled in the outer human serum albumin as blocking group of metal; Wrap up the paramagnetic metal ion coordination compound shell of described metal nano kernel, described shell comprises the covalently bound chelating agen by amido link and human albumin, and coordination is incorporated into the paramagnetic metal ion on the chelating agen.
Preferably, described core-shell type nano-contrast agent diameter is less than 10nm.
Preferably, described metal nanometre cluster is human albumin-gold nanoclusters or human albumin-silver nanoclusters.
Preferably, described chelating agen is ethylenediaminetetraacetic acid (EDTA) or diethylenetriamine pentaacetic acid (DTPA).
Preferably, described paramagnetic metal ion is the trivalent ion of manganese ion, iron ion or lanthanide series rare-earth elements.
Preferably, described paramagnetic metal ion is Gd
3+
The present invention provides the method for preparing described core-shell type nano-contrast agent on the other hand, comprising:
Metal nanometre cluster preparation: metal ion mixes with the human serum albumin, obtains the first mixed liquor, and the pH value of the first mixed liquor is transferred to 10.0-14.0, reacts to obtain metal nanometre cluster solution;
Chelating agen and metal nanometre cluster covalent bond: in gained metal nanometre cluster solution, add buffer, obtain the second mixed solution, in the second mixed solution, add chelating agen, obtain the 3rd mixed solution, the pH value of the 3rd mixed solution is transferred to 6.0-14.0, and reaction obtains chelating agen-metal nanometre cluster solution;
Chelating agen-metal nanometre cluster is combined with the paramagnetic metal ion coordination: in acid solution, paramagnetic metal ion is dissolved, obtain the 4th mixed liquor, the 4th mixed liquor is mixed with chelating agen-metal nanometre cluster solution, obtain the 5th mixed liquor, the pH value of the 5th mixed solution is transferred to 6.0-8.0, and reaction obtains core-shell type nano-radiography agent solution.
Preferably, described preparation method also comprises: core-shell type nano-radiography agent solution is placed bag filter, respectively at dialysing in buffer and the distilled water.
Preferably, the amount of substance of metal and human serum albumin's mass ratio are (5-10) μ mol:(25-50 in the described metal nanometre cluster preparation) mg.
Preferably, human serum albumin and chelating agen mass ratio are (100-200) in described chelating agen and the metal nanometre cluster covalent bond: (28-50).
Core-shell type three mode nano-contrast agents provided by the invention have the metal nanometre cluster kernel that has fluorescent effect in near-infrared region because containing, and can be used for the NIR imaging; Contain the paramagnetic metal ion with nuclear magnetic resonance effects in the shell of contrast agent of the present invention, described contrast agent also can be used for the MRI imaging; Usually contain the golden or silver-colored of high atomic number in the metal nanometre cluster kernel of contrast agent of the present invention, the absorbance of X ray is high, it is little that contrast agent of the present invention has a nano-scale, easier tissue or the organ of entering, change tissue or organ to the absorption of X ray, therefore described contrast agent also can be used for the CT imaging.
Beneficial effect of the present invention is, the combining nano technology connects paramagnetic metal ion take the human serum albumin as carrier, has realized NIR, CT and MRI three mode imagings, has improved tumor-targeting; Prepared core-shell type nano-contrast agent particle diameter is little, and bio-toxicity is low; Preparation method is simple.
Description of drawings
Fig. 1 is the transmission electron microscope picture of the core-shell type nano-contrast agent of preparation among the embodiment 1.
The specific embodiment
In order to make those skilled in the art better understand the application's technical scheme, below in conjunction with the accompanying drawing in the embodiment of the present application, the technical scheme in the embodiment of the present application is carried out clear, complete description.
The present invention combines the MRI radiography function three of nanotechnology, human serum albumin's tumor-targeting and paramagnet, has invented a kind of contrast agent, has effectively realized NIR, CT and MRI three mode imagings.
Contrast agent of the present invention is the core-shell type nano-contrast agent; its kernel is metal nanometre cluster; being made of metal and human serum albumin, is a kind ofly to form core, the molecular level aggregation that the human serum albumin assembles as blocking group by the several of metal to tens atoms.For example, the metal nanometre cluster among the present invention can be human albumin-gold nanoclusters or human albumin-silver nanoclusters.Metal nanometre cluster is the water soluble molecules aggregation with fluorescence, but its distinctive quantum size effect makes the harmony in visible light arrives the near-infrared region scope of its fluorescence emission spectrum.Simultaneously, good biocompatibility and light stability make it become high performance biomarker.
The shell of core-shell type nano-contrast agent is made of the paramagnetic metal ion coordination compound, comprise by the covalently bound chelating agen of human albumin in amido link and the kernel, and coordination is incorporated into the paramagnetic metal ion on the chelating agen.Make contrast agent of the present invention have the MRI imaging function by introducing paramagnet at the metal nanometre cluster kernel.For example, chelating agen can be ethylenediaminetetraacetic acid (EDTA) or diethylenetriamine pentaacetic acid (DTPA), but does not get rid of other available chelating agen.Paramagnetic metal ion is selected the trivalent ion of manganese ion, iron ion or lanthanide series rare-earth elements.Paramagnetic metal ion is preferably Gd
3+, Eu
3+, Fe
3+Or Mn
2+, Gd more preferably
3+Or Mn
2+, most preferably be Gd
3+
The present invention also provides the method for this core-shell type nano-contrast agent of preparation, mainly may further comprise the steps:
At first, preparation metal nanometre cluster.Comprise metal and human serum albumin in the metal nanometre cluster, be used to form the composition of core-shell type nano-contrast agent kernel portion.Metal ion is mixed with the human serum albumin, obtain the first mixed liquor, the pH value of the first mixed liquor is transferred to 10.0-14.0, reaction obtains metal nanometre cluster solution.Can help even mixing by stirring, concussion, the mode such as ultrasonic when preparing the first mixed liquor.It is optional with NaOH solution or KOH solution to regulate the first mixed liquor pH value.Reaction condition is preferably incubation, and more preferably 37 ℃ of incubations are followed gentle agitation or placed slightly concussion on the shaking table.The amount of substance of metal and human serum albumin's mass ratio are preferably (5-10) μ mol:(25-50 in the described metal nanometre cluster preparation) mg, more preferably 1 μ mol:10mg-1 μ mol:5mg most preferably is 1 μ mol:10mg or 1 μ mol:5mg.
Then, preparation chelating agen and metal nanometre cluster covalent conjunct agent (chelating agen-metal nanometre cluster).Add buffer in gained metal nanometre cluster solution, obtain the second mixed solution, add chelating agen in the second mixed solution, obtain the 3rd mixed solution, the pH value of the 3rd mixed solution is transferred to 6.0-14.0, reaction obtains chelating agen-metal nanometre cluster solution.Be preferably the PBS solution of pH6-14 with buffer, can help even mixing by modes such as stirring, concussions when preparing the second mixed liquor or the 3rd mixed liquor.Regulate the 3rd mixed liquor pH value by dripping NaOH solution or KOH solution.Reaction temperature is preferably room temperature, follows gentle agitation or places slightly concussion on the shaking table.Human serum albumin and chelating agen mass ratio are preferably and are (100-200) in described chelating agen and the metal nanometre cluster covalent bond: (28-50), more preferably 100:25-100:32 most preferably is 100:28,125:40 or 200:50.
Then, preparation contains the acid solution of paramagnetic metal ion, and with the standby core-shell type nano-contrast agent of above-mentioned chelating agen-metal nanometre cluster solution mixing system.In acid solution, with the paramagnetic metal ion dissolving, obtain the 4th mixed liquor, the 4th mixed liquor is mixed with chelating agen-metal nanometre cluster solution, obtain the 5th mixed liquor, the pH value of the 5th mixed solution is transferred to 6.0-8.0, reaction obtains core-shell type nano-radiography agent solution.Regulate the 5th mixed liquor pH value by dripping NaOH solution or KOH solution.Reaction temperature is preferably room temperature, follows gentle agitation or places slightly concussion on the shaking table.
The core-shell type nano-contrast agent that is formed in the solution can be further purified.Core-shell type nano-radiography agent solution is placed bag filter, respectively at dialysing in buffer and the distilled water.The purpose of dialysis is to remove inorganic molecules.Described buffer is preferably PBS solution.Core-shell type nano-radiography agent solution is placed bag filter, the 1-300h that at first in PBS solution, dialyses, every 1-12h changes PBS solution; Place again dialysis 1-12h in the distilled water.
Below be embodiment.
Employed experimental technique is conventional method if no special instructions among the following embodiment.
Used material, reagent etc. if no special instructions, all can obtain from commercial channels among the following embodiment.
Raw material and reagent:
Chlorauric acid solution; The HAS(human serum albumin) solution; DTPACA(diethylenetriamine pentaacetic acid cyclic anhydride); The PBS(phosphate buffer) solution; NaOH solution; HCl solution; GdCl
3.6H
2O; Distilled water.
Embodiment 1
The preparation of a, gold nanoclusters:
10mmol/L chlorauric acid solution and 50mg/mL HSA solution are bathed in 37 ℃ of lower temperature, make above-mentioned two kinds of solution constant temperature to 37 ℃, the 0.5mL chlorauric acid solution is joined in the 0.5mL HSA solution, mix homogeneously, add again 1mol/L NaOH solution 0.05mL, the adjusting pH value is strong basicity (pH10.0-14.0), and the gained mixed liquor is placed 37 ℃ of shaking table incubation 12h, forms metal nanometre cluster solution.
B, chelating agen and metal nanometre cluster covalent bond:
Get above-mentioned metal nanometre cluster solution 4ml, add 0.2mL PBS solution (2mol/L, pH=9), mix, in above-mentioned mixed solution, add 28mg DTPACA powder, with the titration of 5mol/L NaOH solution, adjust pH value to 6.0-8.0, place shaking table reaction 2h under the room temperature, obtain chelating agen-metal nanometre cluster solution.
C, chelating agen-metal nanometre cluster are combined with the paramagnetic metal ion coordination:
Take by weighing 30mg GdCl
3.6H
2O is dissolved among the 1mL1mol/L HCl, obtains Gd
3+Acid solution is with Gd
3+Acid solution is poured in gained chelating agen-metal nanometre cluster solution, with the titration of 5mol/LNaOH solution, adjusts pH value to 6.0-8.0, places shaking table reaction 2h under the room temperature, obtains core-shell type nano-radiography agent solution.
D, core-shell type nano-contrast agent purification:
Gained core-shell type nano-radiography agent solution is moved into bag filter, under the room temperature, bag filter is placed the 16h that dialyses in the 500ml PBS buffer, every 8h changes the new PBS buffer of liquid, after bag filter is placed the 8h that dialyses in the 500ml distilled water, remove inorganic molecules in the solution.
Fig. 1 is the transmission electron microscope picture of the core-shell type nano-contrast agent for preparing in the present embodiment, as shown in Figure 1, core-shell type nano-contrast agent particle diameter of the present invention little (diameter is less than 10nm), good dispersion, suspension stability is good.
Embodiment 2
The preparation of a, gold nanoclusters:
10mmol/L chlorauric acid solution and 50mg/mL HSA solution are bathed in 37 ℃ of lower temperature, make above-mentioned two kinds of solution constant temperature to 37 ℃, the 1mL chlorauric acid solution is joined in the 1mL HSA solution, mix homogeneously, add again 1mol/L NaOH solution 0.05mL, the adjusting pH value is strong basicity (pH10.0-14.0), and the gained mixed liquor is placed 37 ℃ of shaking table incubation 24h, forms metal nanometre cluster solution.
B, chelating agen and metal nanometre cluster covalent bond:
Get above-mentioned metal nanometre cluster solution 5ml, add 0.2mL PBS solution (4mol/L, pH=9), mix, in above-mentioned mixed solution, add 40mg DTPACA powder, with the titration of 5mol/LNaOH solution, adjust pH value to 9.0, place shaking table reaction 1h under the room temperature, obtain chelating agen-metal nanometre cluster solution.
C, chelating agen-metal nanometre cluster are combined with the paramagnetic metal ion coordination:
Take by weighing 50mg GdCl
3.6H
2O is dissolved among the 0.05mL1mol/L HCl, obtains Gd
3+Acid solution is with Gd
3+Acid solution is poured in gained chelating agen-metal nanometre cluster solution, with the titration of 3mol/L NaOH solution, adjusts pH value to 10.0, places shaking table reaction 1h under the room temperature, obtains core-shell type nano-radiography agent solution.
D, core-shell type nano-contrast agent purification:
Gained core-shell type nano-radiography agent solution is moved into bag filter, under the room temperature, bag filter is placed the 16h that dialyses in the 500ml PBS buffer, every 8h changes the new PBS buffer of liquid, after bag filter is placed the 8h that dialyses in the 500ml distilled water, remove inorganic molecules in the solution.
Embodiment 3
The preparation of a, gold nanoclusters:
20mmol/L chlorauric acid solution and 100mg/mL HSA solution are bathed in 37 ℃ of lower temperature, make above-mentioned two kinds of solution constant temperature to 37 ℃, the 0.5mL chlorauric acid solution is joined in the 0.5mL HSA solution, mix homogeneously, add again 1mol/L NaOH solution 0.1mL, the adjusting pH value is strong basicity (pH10.0-14.0), and the gained mixed liquor is placed 37 ℃ of shaking table incubation 20h, forms metal nanometre cluster solution.
B, chelating agen and metal nanometre cluster covalent bond:
Get above-mentioned metal nanometre cluster solution 4ml, add 0.1mL PBS solution (3mol/L, pH=9), mix, in above-mentioned mixed solution, add 50mg DTPACA powder, with the titration of 3mol/LNaOH solution, adjust pH value to 10.0, place shaking table reaction 3h under the room temperature, obtain chelating agen-metal nanometre cluster solution.
C, chelating agen-metal nanometre cluster are combined with the paramagnetic metal ion coordination:
Take by weighing 70mg GdCl
3.6H
2O is dissolved among the 3mL0.5mol/L HCl, obtains Gd
3+Acid solution is with Gd
3+Acid solution is poured in gained chelating agen-metal nanometre cluster solution, with the titration of 6mol/LNaOH solution, adjusts pH value to 9.0, places shaking table reaction 3h under the room temperature, obtains core-shell type nano-radiography agent solution.
D, core-shell type nano-contrast agent purification:
Gained core-shell type nano-radiography agent solution is moved into bag filter, under the room temperature, bag filter is placed the 32h that dialyses in the 500ml PBS buffer, every 8h changes the new PBS buffer of liquid, after bag filter is placed the 8h that dialyses in the 500ml distilled water, remove inorganic molecules in the solution.
Above-described embodiment of the present invention does not consist of the restriction to protection domain of the present invention.Any modification of doing within the spirit and principles in the present invention, be equal to and replace and improvement etc., all should be included within the claim protection domain of the present invention.
Claims (10)
1. core-shell type three mode nano-contrast agents comprise:
The metal nanometre cluster kernel, described metal nanometre cluster kernel comprises metal, and is assembled in the outer human serum albumin as blocking group of metal; With
Wrap up the paramagnetic metal ion coordination compound shell of described metal nano kernel, described shell comprises the covalently bound chelating agen by amido link and human albumin, and coordination is incorporated into the paramagnetic metal ion on the chelating agen.
2. core-shell type three mode nano-contrast agents according to claim 1 is characterized in that diameter is less than 10nm.
3. core-shell type three mode nano-contrast agents according to claim 1 is characterized in that described metal nanometre cluster is human albumin-gold nanoclusters or human albumin-silver nanoclusters.
4. core-shell type three mode nano-contrast agents according to claim 1 is characterized in that, described chelating agen is ethylenediaminetetraacetic acid (EDTA) or diethylenetriamine pentaacetic acid (DTPA).
5. core-shell type three mode nano-contrast agents according to claim 1 is characterized in that described paramagnetic metal ion is the trivalent ion of manganese ion, iron ion or lanthanide series rare-earth elements.
6. core-shell type three mode nano-contrast agents according to claim 5 is characterized in that described paramagnetic metal ion is Gd
3+
7. prepare the method for each described core-shell type nanometer three mode contrast agent in the claim 1 to 6, comprising:
Metal nanometre cluster preparation: metal ion mixes with the human serum albumin, obtains the first mixed liquor, and the pH value of the first mixed liquor is transferred to 10.0-14.0, reacts to obtain metal nanometre cluster solution;
Chelating agen and metal nanometre cluster covalent bond: in gained metal nanometre cluster solution, add buffer, obtain the second mixed solution, in the second mixed solution, add chelating agen, obtain the 3rd mixed solution, the pH value of the 3rd mixed solution is transferred to 6.0-14.0, and reaction obtains chelating agen-metal nanometre cluster solution;
Chelating agen-metal nanometre cluster is combined with the paramagnetic metal ion coordination: in acid solution, paramagnetic metal ion is dissolved, obtain the 4th mixed liquor, the 4th mixed liquor is mixed with chelating agen-metal nanometre cluster solution, obtain the 5th mixed liquor, the pH value of the 5th mixed solution is transferred to 6.0-8.0, and reaction obtains core-shell type nano-radiography agent solution.
8. preparation method according to claim 7 also comprises:
Core-shell type three mode nano-radiography agent solutions are placed bag filter, respectively at dialysing in buffer and the distilled water.
9. preparation method according to claim 7 is characterized in that, the amount of substance of metal and human serum albumin's mass ratio are (5-10) μ mol:(25-50 in the described metal nanometre cluster preparation) mg.
10. preparation method according to claim 7 is characterized in that, human serum albumin and chelating agen mass ratio are (100-200) in described chelating agen and the metal nanometre cluster covalent bond: (28-50).
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| CN104672462A (en) * | 2015-03-05 | 2015-06-03 | 北京工商大学 | Multi-tooth bionic ligand for improving biocompatibility and stability of nano particles as well as preparation method of multi-tooth bionic ligand |
| CN104801722A (en) * | 2015-03-13 | 2015-07-29 | 武汉理工大学 | Preparation method of human serum albumin gold nanoclusters |
| CN105238394A (en) * | 2015-09-26 | 2016-01-13 | 福建医科大学 | 3-mercaptopropionic acid-human serum-gold nanometer clusters fluorescent material and preparation method thereof |
| CN105950150A (en) * | 2016-03-16 | 2016-09-21 | 深圳大学 | Core/shell-type multifunctional nano material and preparation method thereof |
| CN105950150B (en) * | 2016-03-16 | 2018-05-08 | 深圳大学 | A kind of core-shell type multifunctional nano material and preparation method thereof |
| WO2018036078A1 (en) * | 2016-08-23 | 2018-03-01 | 红婴生物科技股份有限公司 | Method for preparing solution containing ligand-bonded gold nanoclusters |
| CN113413470A (en) * | 2021-05-31 | 2021-09-21 | 深圳先进技术研究院 | Tumor diagnosis and treatment agent and preparation method and application thereof |
| WO2022252012A1 (en) * | 2021-05-31 | 2022-12-08 | 深圳先进技术研究院 | Tumor diagnosis and treatment agent, preparation method therefor and application thereof |
| CN113413470B (en) * | 2021-05-31 | 2024-01-16 | 深圳先进技术研究院 | Tumor diagnosis and treatment agent and preparation method and application thereof |
| CN116496786A (en) * | 2023-07-01 | 2023-07-28 | 北京建工环境修复股份有限公司 | Gadolinium nanocluster fluorescent probe and application thereof in environment detection |
| CN116496786B (en) * | 2023-07-01 | 2023-09-29 | 北京建工环境修复股份有限公司 | Gadolinium nanocluster fluorescent probe and application thereof in environment detection |
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