CN104117073B - A kind of Double-mode imaging nano-micelle and its production and use - Google Patents
A kind of Double-mode imaging nano-micelle and its production and use Download PDFInfo
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Abstract
The invention discloses a kind of Double-mode imaging nano-micelle, it includes CT contrast agent, HONGGUANG fluorescence molecule NPAPF and described CT contrast agent and NPAPF bag is loaded in the bag carrier material in described Double-mode imaging nano-micelle, also disclose preparation method and the purposes of described double mode nano-micelle, fluorescence imaging and CT imaging are combined by it, achieving the targeting Double-mode imaging to vivo tumor and organ, by force and toxicity is the least for long action time, detection signal simultaneously.
Description
Technical field
The invention belongs to biomedical imaging field, relate to a kind of nano-micelle and its production and use,
Relating more specifically to nano-micelle of a kind of Double-mode imaging and its production and use, it is by fluorescence imaging
Combine with CT imaging, it is achieved living animal targeting and imaging.
Background technology
Malignant tumor is one of main disease of harm human health.The data issued according to International Union Against Cancer
Understanding, 2008, the whole world had 12,700,000 people to obtain cancer, and death reaches 7,600,000 people.If do not taked effectively to arrange
Execute, it is contemplated that to the year two thousand thirty, will appear from 26,000,000 every year and increase cases of cancer newly.The most worldwide,
Or in China, cancer has become first cause of the death of the mankind.So, develop effective cancer imaging diagnostic agent
To promoting that compatriots' health is significant.
Aggregation-induced emission (AIE) refers to that class fluorescence chromophore Weak-luminescence under solution state is not even sent out
Light, and a kind of optical physics phenomenon that fluorescence is obviously enhanced under solid-state or coherent condition.There is AIE characteristic
Molecule has, in field of biological detection, the advantage that conventional fluorescent probe molecule can not compare as fluorescent probe.Pass
During the interphase interaction answering fluorescent probe molecule and solvent or other molecules of system, fluorescence intensity weakens, i.e.
Fluorescence-quenching, and when fluorescent probe molecule is assembled to finite concentration, quenching phenomenon can be produced from, no
Cancer location imaging can be used for well.But, there is the fluorescence molecule of AIE characteristic, on the one hand it does not produce
Raw fluorescent quenching, can be attached on biomacromolecule obtain the fluorescence of high brightness, more for fluoroscopic examination
Provide convenience；On the other hand, it occurs fluorescence drastically to brighten after assembling, and can detect as Fluorescence amplification
Quantitative basis.Therefore, the bio-imaging that appears as of this quasi-molecule brings dawn.
Computed tomography (CT) imaging technique is owing to having higher spatial resolution, and easy to use have
Effect, obtain in the early diagnosis and therapy of the most various diseases especially cancer widely should
With, for enhanced CT imaging effect, reach to meet the image quality of needs, develop suitable preparation and just become
Obtain the most necessary.Traditional CT preparation is typically some micromolecular compounds containing iodine, such as iohexol,
Iodized oil, iopanoic acid and amidotrizoic acid etc., these little molecular imaging agent have many shortcomings, such as blood circulation
Time is short, and imaging acting duration is short, and lacks specificity, it is impossible to tissue is carried out targeted imaging,
There is the most again certain Toxicity of Kidney simultaneously.And currently as the nanometre glue beam CT imaging of research hot topic
Agent, has good targeting in vivo, thus has extraordinary in Medical CT field because of it
Application potential.
Patent CN103446595A discloses and a kind of based on nanometer bismuth sulfide becomes with fluorescent dual module formula for CT
The multiprobe of picture.But the bismuth sulfide toxicity that this patent uses is relatively greatly, preparation method is complicated, and the brightest
The acting duration of this Double-mode imaging probe true and the optimal imaging time of both of which.While it is true,
The Double-mode imaging technology that effect fluorescence imaging and CT imaging combine has become the focus of research at present, ability
Territory is badly in need of finding the Double-mode imaging compositions possessing high sensitivity and high spatial resolution double dominant.
Summary of the invention
An object of the present invention is to propose a kind of Double-mode imaging nano-micelle, and it is by fluorescence imaging and CT
Imaging combines, it is achieved that the targeting Double-mode imaging to vivo tumor or organ.
For reaching this purpose, the present invention by the following technical solutions:
A kind of Double-mode imaging nano-micelle, it include CT contrast agent, HONGGUANG fluorescence molecule NPAPF and
Described CT contrast agent and NPAPF bag are loaded in the bag carrier material in described Double-mode imaging nano-micelle.Its
Described in the mass ratio of CT preparation and NPAPF be 1:1-1:3, such as 1:1,1:2 or 1:3；Described CT
Preparation and described bag carrier material mass ratio are 1:8-1:15, such as 1:8,1:9 or 1:10.
Described CT contrast agent is the mixture of a kind of or at least two in Operand, barium sulfate and gold grain.
Described bag carrier material is PGA-PEG, DSPE-PEG, PLGA-PEG, PEG-NH2、PEG-COOH、
A kind of or the mixture of at least two in PEG-OPSS, PCL-PEG, TPGS, HS15 and phospholipid.?
In the preferred embodiment of the invention, described bag carrier material is PLGA-PEG, DSPE-PEG or PEG-NH2。
The structure of the Double-mode imaging nano-micelle of the present invention is as it is shown in figure 1, double mode by the present invention
The electron-microscope scanning of imaging nano-micelle, it is known that its particle diameter is 60～100nm, has good tumor and organ target
Tropism.
NPAPF used in the present invention is the HONGGUANG fluorescence molecule of aggregation-induced emission, its structure such as formula 1 institute
Show.
Its fluorescence under solid-state or coherent condition is obviously enhanced, and will not mutual because of with solvent or contrast agent
There is fluorescent quenching in effect, in conjunction with the targeting of nanometer formulation, can be gathered in tumor locus and carry out fluorescence one-tenth
Picture.The present invention uses nanotechnology CT contrast agent and NPAPF bag to be loaded in nano-micelle, prepares height
The preparation of fluorescent emission intensity, and achieve live body targeting fluorescence/CT Double-mode imaging, overcome existing list
The deficiency of mode imaging technology, it is provided that the nano-micelle preparation of a kind of Double-mode imaging.
It is a further object of the present invention to provide the preparation method of described Double-mode imaging nano-micelle, including two kinds
Preferably method.
First method comprises the following steps: be dissolved in organic molten by bag carrier material, CT contrast agent and NPAPF
Agent, adds aqueous solvent and mixes, and removes organic solvent, obtains described Double-mode imaging nano-micelle.
The preparation method of another kind of described Double-mode imaging nano-micelle comprises the following steps: by bag carrier material,
CT contrast agent, NPAPF are dissolved in organic solvent, remove organic solvent, add aqueous solvent aquation, obtain
Described Double-mode imaging nano-micelle.
Wherein said organic solvent is the one in chloroform, dichloromethane, acetone, ethanol and methanol or at least
The mixture of two kinds, in a preferred embodiment of the present invention, described organic solvent is chloroform and/or dichloromethane
Alkane.
Described aqueous solvent is deionized water, PBS, normal saline, glucose injection and amino
The mixture of a kind of or at least two in acid injection, in a preferred embodiment of the present invention, described water
Property solvent is deionized water, PBS and/or normal saline.
The amount of described organic solvent be at least solubilized and disperse described NPAPF and CT contrast agent amount.Institute
Stating and removing the method that used of organic solvent is solvent evaporation method, emulsion process, rotation embrane method, dialysis, lyophilizing
The combination of a kind of or at least two in method.The volume of described aqueous solvent is described organic solvent volume
10-15 times, such as 10 times, 11 times, 12 times, 14 times or 15 times, preferably 10 times.
The Double-mode imaging nano-micelle that the present invention also aims to provide described is preparing tumor and organ target
Purposes in preparation.
The Double-mode imaging nano-micelle of the present invention owing to employing special AIE fluorescence molecule NPAPF, from
And this overcoming that CT preparation cancellation common fluorescent molecular makes that its imaging effect substantially weakens well lacks
Fall into.Use tail vein injection mode to be injected in Mice Body by a certain amount of nano-micelle, use after certain time
Multispectral small animal living body imaging system and computed tomographic scanner (CT) carry out fluorescence and CT to mice
Image checking, be appreciated that the Double-mode imaging nano-micelle of the present invention have concurrently fluorescence imaging high sensitivity and
The double dominant of the high spatial resolution of CT imaging, to organ and the tumors of tumor-bearing mice such as the lymph nodes of mice
There is good targeting at position.
The method have the advantages that
(1) the Double-mode imaging nano-micelle of the present invention employs special aggregation-induced emission fluorescence molecule
NPAPF, greatly reduces the fluorescent quenching effect that CT contrast agent causes, and fluorescence is become by prepared nano-micelle
Picture and CT imaging combine, and both can carry out fluorescence imaging detection and can also carry out CT imaging analysis, become
Achieve to merit the Double-mode imaging to vivo tumor or organ.
(2) the bag carrier material used by Double-mode imaging nano-micelle preparing the present invention can be amphiphatic,
Its hydrophilic segment can extend the blood circulation time of micelle, thus micelle can have the longest following in vivo
Ring effect.Common fluorescence molecule and contrast agent persistent period are usually no more than 6h, and bimodulus of the present invention
When formula imaging nano-micelle preparations detects after injecting 24h, still there is the strongest fluorescence and CT signal.
(3) the Double-mode imaging nano-micelle particle diameter of the present invention is 60～100nm, have good tumor or
Organ targeting.
(4) the Double-mode imaging nano-micelle toxicity of the present invention is low, good biocompatibility, in high concentration 60
Under conditions of μ g/mL Double-mode imaging nano-micelle, cell survival rate is still more than 80%.
(5) the Double-mode imaging nano-micelle of the present invention is only by a shot, can realize both of which
While image checking, tumor and organ targeting are good, and imaging sustainable time length injection 24h after still may be used
Clearly carry out image checking.If using NPAPF and contrast agent respectively, not only need multiple injection, and
The optimum detection time of different imaging patterns is the most different.
(6) the Double-mode imaging nano-micelle preparation of the present invention is simple, can amplify production, have extraordinary
Practicality and market using value.
Accompanying drawing explanation
Fig. 1 is the structure chart of the Double-mode imaging nano-micelle of the present invention.
Fig. 2 is the Electronic Speculum figure of the Double-mode imaging nano-micelle of the present invention.
Fig. 3 is the cytotoxicity analysis figure of the Double-mode imaging nano-micelle of the present invention
Fig. 4 is after tumor-bearing mice is administered the Double-mode imaging nano-micelle of the present invention, 0h and 24h mice
Fluorescence imaging figure contrasts.
Fig. 5 is after tumor-bearing mice is administered the Double-mode imaging nano-micelle of the present invention, 0h and 24h mice
CT image contrasts.
Fig. 6 is after tumor-bearing mice is administered the Double-mode imaging nano-micelle of the present invention, the organ targeting of mice
Fluorescence imaging figure.
Fig. 7 is after tumor-bearing mice is administered the Double-mode imaging nano-micelle of the present invention, the organ targeting of mice
CT image.
Detailed description of the invention
Further illustrate technical scheme below in conjunction with the accompanying drawings and by detailed description of the invention.
Embodiment 1
The microscopic pattern of the Double-mode imaging nano-micelle of the present invention is observed:
The Double-mode imaging nano-micelle preparing the present invention carries out electron-microscope scanning, sees Fig. 1, it is seen that described bimodulus
Formula imaging nano-micelle is spheroidal particle, its a diameter of about 80nm.
Embodiment 2
The Double-mode imaging nano-micelle of the present invention, prepares by following method:
CT preparation, NPAPF and PLGA-PEG are dissolved in chloroform according to the mass ratio of 1:1:8；
By chloroformic solution and the deionized water mixing of 10 times of volumes of gained, remove organic solvents, chloroform, to obtain final product
Nano-micelle to described Double-mode imaging.
Embodiment 3
The Double-mode imaging nano-micelle of the present invention, prepares by following method:
CT preparation: NPAPF:DSPE-PEG is dissolved in chloroform according to the mass ratio of 1:1:8；
By chloroformic solution and the deionized water mixing of 10 times of volumes of gained, remove organic solvents, chloroform, to obtain final product
Nano-micelle to described Double-mode imaging.
Embodiment 4
The Double-mode imaging nano-micelle of the present invention, prepares by following method:
By CT preparation: NPAPF:PEG-NH2It is dissolved in dichloromethane according to the mass ratio of 1:1:8；
By dichloromethane solution and the deionized water mixing of 10 times of volumes of gained, remove organic solvent dichloromethane
Alkane, i.e. obtains the nano-micelle of described Double-mode imaging.
Embodiment 5
The Double-mode imaging nano-micelle of the present invention, prepares by following method:
CT preparation: NPAPF:PGA-PEG is dissolved in dichloromethane according to the mass ratio of 1:1:8；
By dichloromethane solution and the deionized water mixing of 10 times of volumes of gained, remove organic solvent dichloromethane
Alkane, i.e. obtains the nano-micelle of described Double-mode imaging.
Embodiment 6
The Double-mode imaging nano-micelle of the present invention, prepares by following method:
CT preparation: NPAPF:PEG-OPSS is dissolved in chloroform according to the mass ratio of 1:1:8；
By chloroformic solution and the normal saline mixing of 10 times of volumes of gained, remove organic solvents, chloroform, to obtain final product
Nano-micelle to described Double-mode imaging.
Embodiment 7
The Double-mode imaging nano-micelle of the present invention, prepares by following method:
CT preparation: NPAPF:PEG-COOH is dissolved in chloroform according to the mass ratio of 1:1:8；
By chloroformic solution and the normal saline mixing of 10 times of volumes of gained, remove organic solvents, chloroform, to obtain final product
Nano-micelle to described Double-mode imaging.
Embodiment 8
The Double-mode imaging nano-micelle of the present invention, prepares by following method:
CT preparation: NPAPF:TPGS is dissolved in dichloromethane according to the mass ratio of 1:1:8；
By dichloromethane solution and the normal saline mixing of 10 times of volumes of gained, remove organic solvent dichloromethane
Alkane, i.e. obtains the nano-micelle of described Double-mode imaging.
Embodiment 9
The Double-mode imaging nano-micelle of the present invention, prepares by following method:
CT preparation: NPAPF:HS15 is dissolved in dichloromethane according to the mass ratio of 1:1:8；
By dichloromethane solution and the normal saline mixing of 10 times of volumes of gained, remove organic solvent dichloromethane
Alkane, i.e. obtains the nano-micelle of described Double-mode imaging.
Embodiment 10
The Double-mode imaging nano-micelle of the present invention, prepares by following method:
CT preparation: NPAPF:PCL-PEG is dissolved in chloroform according to the mass ratio of 1:1:8；
By chloroformic solution and the PBS mixing of 10 times of volumes of gained, remove organic solvents, chloroform, i.e.
Obtain the nano-micelle of described Double-mode imaging.
Embodiment 11
The Double-mode imaging nano-micelle of the present invention, prepares by following method:
CT preparation: NPAPF: phospholipid is dissolved in chloroform according to the mass ratio of 1:1:8；
By chloroformic solution and the PBS mixing of 10 times of volumes of gained, remove organic solvents, chloroform, i.e.
Obtain the nano-micelle of described Double-mode imaging.
Embodiment 12
The Double-mode imaging nano-micelle of the present invention, prepares by following method:
CT preparation: NPAPF:PLGA-PEG is dissolved in dichloromethane according to the mass ratio of 1:1:8；
By dichloromethane solution and the PBS mixing of 10 times of volumes of gained, remove organic solvent dichloro
Methane, i.e. obtains the nano-micelle of described Double-mode imaging.
Embodiment 13
The Double-mode imaging nano-micelle of the present invention, prepares by following method:
CT preparation: NPAPF:DSPE-PEG is dissolved in dichloromethane according to the mass ratio of 1:1:8；
By dichloromethane solution and the PBS mixing of 10 times of volumes of gained, remove organic solvent dichloro
Methane, i.e. obtains the nano-micelle of described Double-mode imaging.
Embodiment 14
The Double-mode imaging nano-micelle of the present invention, prepares by following method:
By CT preparation: NPAPF:PEG-NH2It is dissolved in chloroform according to the mass ratio of 1:1:8；
By chloroformic solution and the glucose for injection solution mixing of 10 times of volumes of gained, remove organic solvent chlorine
Imitative, i.e. obtain the nano-micelle of described Double-mode imaging.
Embodiment 15
The Double-mode imaging nano-micelle of the present invention, prepares by following method:
CT preparation: NPAPF:PGA-PEG is dissolved in chloroform according to the mass ratio of 1:1:8；
By chloroformic solution and the glucose for injection solution mixing of 10 times of volumes of gained, remove organic solvent chlorine
Imitative, i.e. obtain the nano-micelle of described Double-mode imaging.
Embodiment 16
The Double-mode imaging nano-micelle of the present invention, prepares by following method:
CT preparation: NPAPF:PEG-OPSS is dissolved in dichloromethane according to the mass ratio of 1:1:8；
By dichloromethane solution and the glucose for injection solution mixing of 10 times of volumes of gained, remove organic molten
Agent dichloromethane, i.e. obtains the nano-micelle of described Double-mode imaging.
Embodiment 17
The Double-mode imaging nano-micelle of the present invention, prepares by following method:
CT preparation: NPAPF:PEG-COOH is dissolved in dichloromethane according to the mass ratio of 1:1:8；
By dichloromethane solution and the glucose for injection solution mixing of 10 times of volumes of gained, remove organic molten
Agent dichloromethane, i.e. obtains the nano-micelle of described Double-mode imaging.
Embodiment 18
The Double-mode imaging nano-micelle of the present invention, prepares by following method:
Similar embodiment 2-17 preparation method, wherein the mass ratio of CT preparation and bag carrier material is 1:9.
Embodiment 19
The Double-mode imaging nano-micelle of the present invention, prepares by following method:
Similar embodiment 2-17 preparation method, wherein the mass ratio of CT preparation and bag carrier material is 1:10.
Embodiment 20
The Double-mode imaging nano-micelle of the present invention, prepares by following method:
Similar embodiment 2-17 preparation method, wherein CT preparation and NPAPF mass ratio are 1:2.
Embodiment 21
The Double-mode imaging nano-micelle of the present invention, prepares by following method:
Similar embodiment 2-17 preparation method, wherein CT preparation and NPAPF mass ratio are 1:3.
Embodiment 22
Double-mode imaging nano-micelle cytotoxicity analysis of the present invention
According to the conventional method in field, the cytotoxicity of the Double-mode imaging nano-micelle of the present invention is carried out
Analyze.As shown in Figure 3.The Double-mode imaging nano-micelle culture fluid of 6 kinds of variable concentrations of configuration carries out cell
Cultivate, and detect its cell survival rate.Condition at higher concentration 60 μ g/mL Double-mode imaging nano-micelle
Under, cell survival rate is still more than 80%, and along with concentration increases, survival rate downward trend is slow.Explanation
The Double-mode imaging nano-micelle toxicity of the present invention is low, good biocompatibility.
Embodiment 23
Tumor locus Double-mode imaging detection after tumor-bearing mice injection 24h
Use tail vein injection mode that the Double-mode imaging nano-micelle of the 200 μ L present invention is injected into lotus tumor
Mice Body in, 0h and 24h is simultaneously with multispectral small animal living body imaging system and computed tomography
Instrument (CT) carries out fluorescence and CT image checking to mouse tumor position.The mice fluorogram of gained and CT figure
See Fig. 4 and Fig. 5.Common fluorescence molecule and contrast agent persistent period are usually no more than 6h, and institute of the present invention
State Double-mode imaging nano-micelle preparations inject detect after 24h time, still there is the strongest fluorescence and CT
Signal, and tumor-targeting is the best.
Embodiment 24
Tumor-bearing mice organ Double-mode imaging detects
Use tail vein injection mode that the Double-mode imaging nano-micelle of the present invention of 200 μ L is injected into lotus tumor
In Mice Body, simultaneously with multispectral small animal living body imaging system and computed tomographic scanner (CT) after 24h
Mouse lymph nodes, liver, spleen, kidney and other organs are carried out fluorescence and CT image checking.The mice of gained
Organ targeting fluorogram and CT figure are shown in Fig. 6 and Fig. 7.From fluorogram 6, the Double-mode imaging of the present invention
Nano-micelle is the best to fluorescence and the CT imaging effect of organ, successfully achieves only by once noting
Penetrate, detect while both of which imaging can be carried out.
Applicant states, the present invention illustrates the method detailed of the present invention by above-described embodiment, but the present invention
It is not limited to above-mentioned method detailed, does not i.e. mean that the present invention has to rely on above-mentioned method detailed and could implement.
Person of ordinary skill in the field is it will be clearly understood that any improvement in the present invention, each former to product of the present invention
The equivalence of material is replaced and the interpolation of auxiliary element, concrete way choice etc., all falls within the protection model of the present invention
Within the scope of enclosing and disclosing.
Claims (8)
1. a Double-mode imaging nano-micelle, its by CT contrast agent, HONGGUANG fluorescence molecule NPAPF with
And described CT contrast agent and NPAPF bag are loaded in the bag carrier material system in described Double-mode imaging nano-micelle
Becoming, described CT contrast agent is the mixture of a kind of or at least two in Operand, barium sulfate and gold grain,
Described bag carrier material is PGA-PEG, DSPE-PEG, PLGA-PEG, PEG-NH2、
One or at least two in PEG-COOH, PEG-OPSS, PCL-PEG, TPGS, HS15 and phospholipid
The mixture planted, the mass ratio of described CT preparation and NPAPF is 1:1-1:3；Described CT preparation and
Described bag carrier material mass ratio is 1:8-1:15.
The preparation method of Double-mode imaging nano-micelle the most according to claim 1, its feature exists
In, comprise the following steps: bag carrier material, CT contrast agent and NPAPF are dissolved in organic solvent, add water
Property solvent mixing, remove organic solvent, obtain described Double-mode imaging nano-micelle.
The preparation method of Double-mode imaging nano-micelle the most according to claim 1, its feature exists
In, comprise the following steps: bag carrier material, CT contrast agent, NPAPF are dissolved in organic solvent, and removing has
Machine solvent, adds aqueous solvent aquation, obtains described Double-mode imaging nano-micelle.
4. according to the preparation method described in Claims 2 or 3, it is characterised in that described organic solvent is chlorine
A kind of or the mixture of at least two in imitative, dichloromethane, acetone, ethanol and methanol.
5. according to the preparation method described in Claims 2 or 3, it is characterised in that described aqueous solvent is for going
One in ionized water, PBS, normal saline, glucose injection and amino acid injection or extremely
The mixture of few two kinds.
6. according to the preparation method described in Claims 2 or 3, it is characterised in that described removing organic solvent
The method used is the one in solvent evaporation method, emulsion process, rotation embrane method, dialysis, lyophilization or extremely
The combination of few two kinds.
7. according to the preparation method described in Claims 2 or 3, it is characterised in that the body of described aqueous solvent
Amass 10-15 times for described organic solvent volume.
Double-mode imaging nano-micelle the most according to claim 1 becomes in preparation tumor and organ targeting
As the purposes in agent.
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| CN110075320B (en) * | 2019-04-24 | 2021-09-17 | 温州医科大学 | Bimodal tracer for targeting non-small cell lung cancer |
| CN110302399B (en) * | 2019-05-07 | 2022-02-22 | 牡丹江医学院 | Targeted enhanced CT imaging contrast agent and preparation method thereof |
| CN114588278A (en) * | 2022-02-23 | 2022-06-07 | 康达洲际医疗器械有限公司 | fluorescence-CT bimodal molecular probe, preparation method and application thereof |
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| CN103446595A (en) * | 2013-08-01 | 2013-12-18 | 华中科技大学 | Multifunctional probe for CT (Computed Tomography) and dual-mode fluorescent imaging based on nanometer bismuth sulfide |
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| Pluronic F127–folic acid encapsulated nanoparticles with aggregation-induced emission characteristics for targeted cellular imaging;Hongguang Lu et al.;《RSC Adv.》;20140407;第4卷;第18460-18466页 * |
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