CN104117073A - Dual-mode imaging nano-micelle as well as preparation method and application thereof - Google Patents
Dual-mode imaging nano-micelle as well as preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses dual-mode imaging nano-micelle which comprises a CT (Computed tomography) contrast medium, red fluorescent molecules NPAPF (N-(2-naphthyl)phenylamino)phenyl)-fumaronitrile) and a carrying material for carrying the CT contrast medium and the NPAPF into the dual-mode imaging nano-micelle. The invention further discloses a preparation method and an application of the dual-mode imaging nano-micelle. The dual-mode imaging nano-micelle combines fluorescent imaging and CT imaging, achieves targeted dual-mode imaging of living tumor and organs and meanwhile is long in action time, intensive in detection signal and very small in toxicity.
Description
Technical field
The invention belongs to biomedical imaging field, relate to a kind of nano-micelle and its production and use, relate more specifically to nano-micelle of a kind of Double-mode imaging and its production and use, it combines fluorescence imaging and CT imaging, realizes living animal targeting and imaging.
Background technology
Malignant tumor is one of main disease of harm humans health.Data according to International Union Against Cancer's issue are known, and 2008, the whole world had 1,270 ten thousand people to obtain cancer, and death reaches 7,600,000 people.If do not adopted an effective measure, expect the year two thousand thirty, will there are every year 2600 ten thousand newly-increased cases of cancers.No matter worldwide, still in China, cancer has become first cause of the death of the mankind.So, develop effective cancer imaging diagnostic agent to promoting compatriots' health to be significant.
Aggregation inducing luminous (AIE) refers to that class fluorescence chromophore Weak-luminescence under solution state is even not luminous, and a kind of optical physics phenomenon that fluorescence significantly strengthens under solid-state or coherent condition.The molecule with AIE characteristic has conventional fluorescent probe molecule not compare as fluorescent probe in field of biological detection.Traditional answer fluorescence intensity while interacting between fluorescent probe molecule and solvent or other molecules to weaken, it is Fluorescence-quenching, and when fluorescent probe molecule is focused to finite concentration, can produce self-quenching phenomenon, can not be well for cancer location imaging.Yet, thering is the fluorescence molecule of AIE characteristic, it does not produce fluorescent quenching on the one hand, can be attached to more the fluorescence that obtains high brightness on biomacromolecule, for fluoroscopic examination is provided convenience; On the other hand, after its gathering, there is fluorescence and sharply brighten, can be used as the quantitative basis that Fluorescence amplification detects.Therefore, the bio-imaging that appears as of this quasi-molecule has brought dawn.
Computed tomography (CT) imaging technique is owing to having higher spatial resolution, easy to use effective, at present various diseases is especially widely used in the early diagnosis and therapy of cancer clinically, for enhanced CT imaging effect, reach the image quality of satisfying the demand, develop suitable preparation and just become very necessary.Traditional CT preparation more normally contains the micromolecular compound of iodine, such as iohexol, iodized oil, iopanoic acid and amidotrizoic acid etc., these micromolecule preparations have many shortcomings, for example blood circulation time is short, imaging acting duration is short, and shortage specificity, can not carry out targeted imaging to tissue, under high dose, there is again certain Toxicity of Kidney simultaneously.And at present as the popular nano-micelle CT preparation of research, because it has good targeting in vivo, thereby have extraordinary application potential in Medical CT field.
Patent CN103446595A discloses a kind of multiprobe for CT and the imaging of fluorescent dual module formula based on nanometer bismuth sulfide.Yet the bismuth sulfide toxicity that this patent is used is larger, preparation method is complicated, and clear and definite optimal imaging time of the acting duration of this Double-mode imaging probe and two kinds of patterns not.However, the Double-mode imaging technology that effect fluorescence imaging and CT imaging combine has become the focus of current research, and the Double-mode imaging compositions that possesses high sensitivity and high spatial resolution double dominant is badly in need of finding in this area.
Summary of the invention
One of object of the present invention is to propose a kind of Double-mode imaging nano-micelle, and it combines fluorescence imaging and CT imaging, has realized the targeting Double-mode imaging to vivo tumor or organ.
For reaching this object, the present invention by the following technical solutions:
A Double-mode imaging nano-micelle, it comprises CT contrast agent, HONGGUANG fluorescence molecule NPAPF and described CT contrast agent and NPAPF bag is loaded in to the bag carrier material in described Double-mode imaging nano-micelle.The mass ratio of wherein said CT preparation and NPAPF is 1:1-1:3, for example 1:1,1:2 or 1:3; Described CT preparation and described bag carrier material mass ratio are 1:8-1:15, for example 1:8,1:9 or 1:10.
Described CT contrast agent is the mixture of a kind of in Operand, barium sulfate and gold grain or at least two kinds.
Described bag carrier material is PGA-PEG, DSPE-PEG, PLGA-PEG, PEG-NH
2, a kind of in PEG-COOH, PEG-OPSS, PCL-PEG, TPGS, HS15 and phospholipid or at least two kinds mixture.In the preferred embodiment of the invention, described bag carrier material is PLGA-PEG, DSPE-PEG or PEG-NH
2.
As shown in Figure 1, by the electron-microscope scanning to Double-mode imaging nano-micelle of the present invention, known its particle diameter is 60～100nm to the structure of Double-mode imaging nano-micelle of the present invention, has good tumor and organ targeting.
NPAPF used in the present invention is the luminous HONGGUANG fluorescence molecule of aggregation inducing, and its structure as shown in Equation 1.
Its fluorescence under solid-state or coherent condition significantly strengthens, and can be because of the interaction generation fluorescent quenching with solvent or contrast agent, and the targeting of combining nano preparation, can be gathered in tumor locus and carry out fluorescence imaging.The present invention adopts nanotechnology that CT contrast agent and NPAPF bag are loaded in nano-micelle, prepare the preparation of high fluorescent emission intensity, and realized live body targeting fluorescence/CT Double-mode imaging, overcome the deficiency of existing monotype imaging technique, a kind of nano-micelle preparation of Double-mode imaging is provided.
Another object of the present invention is to provide the preparation method of described Double-mode imaging nano-micelle, comprises two kinds of preferred methods.
First method comprises the following steps: bag carrier material, CT contrast agent and NPAPF are dissolved in to organic solvent, add aqueous solvent and mix, remove organic solvent, obtain described Double-mode imaging nano-micelle.
The preparation method of another kind of described Double-mode imaging nano-micelle comprises the following steps: bag carrier material, CT contrast agent, NPAPF are dissolved in to organic solvent, remove organic solvent, add aqueous solvent aquation, obtain described Double-mode imaging nano-micelle.
Wherein said organic solvent is the mixture of a kind of in chloroform, dichloromethane, acetone, ethanol and methanol or at least two kinds, and in the preferred embodiment of the invention, described organic solvent is chloroform and/or dichloromethane.
Described aqueous solvent is the mixture of a kind of in deionized water, PBS buffer, normal saline, glucose injection and amino acid injection or at least two kinds, in the preferred embodiment of the invention, described aqueous solvent is deionized water, PBS buffer and/or normal saline.
The amount of described organic solvent is solubilized and disperse described NPAPF and the amount of CT contrast agent at least.Describedly remove method that organic solvent uses for solvent evaporation method, emulsion process, the combination of revolving a kind of in embrane method, dialysis, lyophilization or at least two kinds.The volume of described aqueous solvent is 10-15 times of described organic solvent volume, for example 10 times, 11 times, 12 times, 14 times or 15 times, and preferably 10 times.
The present invention also aims to provide the described Double-mode imaging nano-micelle purposes in preparation tumor and the agent of organ targeted imaging.
Double-mode imaging nano-micelle of the present invention, owing to having used special AIE fluorescence molecule NPAPF, makes obviously this defect of weakening of its imaging effect thereby overcome well the common fluorescence molecule of CT preparation cancellation.Adopt tail vein injection mode that a certain amount of nano-micelle is injected in Mice Body, after certain hour, with multispectral small animal living body imaging system and computed tomographic scanner (CT), mice is carried out to fluorescence and CT imaging detection, can learn that Double-mode imaging nano-micelle of the present invention has the double dominant of the high sensitivity of fluorescence imaging and the high spatial resolution of CT imaging concurrently, has good targeting to the tumor locus of the organs such as lymph node of mice and tumor-bearing mice.
The present invention has following beneficial effect:
(1) Double-mode imaging nano-micelle of the present invention has been used special aggregation inducing luminous fluorescent molecule NPAPF, greatly reduced the fluorescent quenching effect that CT contrast agent causes, the nano-micelle making combines fluorescence imaging and CT imaging, both can carry out fluorescence imaging detection and also can carry out CT imaging analysis, successfully realize the Double-mode imaging to vivo tumor or organ.
(2) it can be amphiphatic preparing Double-mode imaging nano-micelle of the present invention bag carrier material used, and its hydrophilic segment can extend the blood circulation time of micelle, thereby micelle can have good long circulating effect in vivo.Common fluorescence molecule and contrast agent persistent period are generally no more than 6h, and Double-mode imaging nano-micelle preparations of the present invention is when injection detects after 24h, still has very strong fluorescence and CT signal.
(3) Double-mode imaging nano-micelle particle diameter of the present invention is 60～100nm, has good tumor or organ targeting.
(4) low, the good biocompatibility of Double-mode imaging nano-micelle toxicity of the present invention, under the condition of high concentration 60 μ g/mL Double-mode imaging nano-micelles, cell survival rate is still more than 80%.
(5) Double-mode imaging nano-micelle of the present invention is only by a shot, and when can realize two kinds of patterns, imaging detects, and tumor and organ targeting are good, and still can clearly carry out imaging detection after long injection of sustainable time of imaging 24h.If use respectively NPAPF and contrast agent, not only need multiple injection, and the optimum detection time of different imaging patterns is also different.
(6) Double-mode imaging nano-micelle preparation of the present invention is simple, can amplify production, has extraordinary practicality and market using value.
Accompanying drawing explanation
Fig. 1 is the structure chart of Double-mode imaging nano-micelle of the present invention.
Fig. 2 is the Electronic Speculum figure of Double-mode imaging nano-micelle of the present invention.
Fig. 3 is the cytotoxicity analysis figure of Double-mode imaging nano-micelle of the present invention
Fig. 4 is after tumor-bearing mice administration Double-mode imaging nano-micelle of the present invention, the fluorescence imaging figure of 0h and 24h mice contrast.
Fig. 5 is after tumor-bearing mice administration Double-mode imaging nano-micelle of the present invention, the CT image of 0h and 24h mice contrast.
Fig. 6 is after tumor-bearing mice administration Double-mode imaging nano-micelle of the present invention, the organ targeting fluorescence imaging figure of mice.
Fig. 7 is after tumor-bearing mice administration Double-mode imaging nano-micelle of the present invention, the organ targeting CT image of mice.
The specific embodiment
Below in conjunction with accompanying drawing and by the specific embodiment, further illustrate technical scheme of the present invention.
Embodiment 1
The microscopic pattern of Double-mode imaging nano-micelle of the present invention is observed:
Double-mode imaging nano-micelle prepared by the present invention carries out electron-microscope scanning, sees Fig. 1, and visible described Double-mode imaging nano-micelle is spheroidal particle, and its diameter is 80nm left and right.
Embodiment 2
Double-mode imaging nano-micelle of the present invention, by following method, prepare:
CT preparation, NPAPF and PLGA-PEG are dissolved in chloroform according to the mass ratio of 1:1:8;
The chloroformic solution of gained is mixed with the deionized water of 10 times of volumes, remove organic solvents, chloroform, obtain the nano-micelle of described Double-mode imaging.
Embodiment 3
Double-mode imaging nano-micelle of the present invention, by following method, prepare:
CT preparation: NPAPF:DSPE-PEG is dissolved in chloroform according to the mass ratio of 1:1:8;
The chloroformic solution of gained is mixed with the deionized water of 10 times of volumes, remove organic solvents, chloroform, obtain the nano-micelle of described Double-mode imaging.
Embodiment 4
Double-mode imaging nano-micelle of the present invention, by following method, prepare:
By CT preparation: NPAPF:PEG-NH
2according to the mass ratio of 1:1:8, be dissolved in dichloromethane;
The dichloromethane solution of gained is mixed with the deionized water of 10 times of volumes, remove organic solvent dichloromethane, obtain the nano-micelle of described Double-mode imaging.
Embodiment 5
Double-mode imaging nano-micelle of the present invention, by following method, prepare:
CT preparation: NPAPF:PGA-PEG is dissolved in dichloromethane according to the mass ratio of 1:1:8;
The dichloromethane solution of gained is mixed with the deionized water of 10 times of volumes, remove organic solvent dichloromethane, obtain the nano-micelle of described Double-mode imaging.
Embodiment 6
Double-mode imaging nano-micelle of the present invention, by following method, prepare:
CT preparation: NPAPF:PEG-OPSS is dissolved in chloroform according to the mass ratio of 1:1:8;
The chloroformic solution of gained is mixed with the normal saline of 10 times of volumes, remove organic solvents, chloroform, obtain the nano-micelle of described Double-mode imaging.
Embodiment 7
Double-mode imaging nano-micelle of the present invention, by following method, prepare:
CT preparation: NPAPF:PEG-COOH is dissolved in chloroform according to the mass ratio of 1:1:8;
The chloroformic solution of gained is mixed with the normal saline of 10 times of volumes, remove organic solvents, chloroform, obtain the nano-micelle of described Double-mode imaging.
Embodiment 8
Double-mode imaging nano-micelle of the present invention, by following method, prepare:
CT preparation: NPAPF:TPGS is dissolved in dichloromethane according to the mass ratio of 1:1:8;
The dichloromethane solution of gained is mixed with the normal saline of 10 times of volumes, remove organic solvent dichloromethane, obtain the nano-micelle of described Double-mode imaging.
Embodiment 9
Double-mode imaging nano-micelle of the present invention, by following method, prepare:
CT preparation: NPAPF:HS15 is dissolved in dichloromethane according to the mass ratio of 1:1:8;
The dichloromethane solution of gained is mixed with the normal saline of 10 times of volumes, remove organic solvent dichloromethane, obtain the nano-micelle of described Double-mode imaging.
Embodiment 10
Double-mode imaging nano-micelle of the present invention, by following method, prepare:
CT preparation: NPAPF:PCL-PEG is dissolved in chloroform according to the mass ratio of 1:1:8;
The chloroformic solution of gained is mixed with the PBS buffer of 10 times of volumes, remove organic solvents, chloroform, obtain the nano-micelle of described Double-mode imaging.
Embodiment 11
Double-mode imaging nano-micelle of the present invention, by following method, prepare:
By CT preparation: NPAPF: phospholipid is dissolved in chloroform according to the mass ratio of 1:1:8;
The chloroformic solution of gained is mixed with the PBS buffer of 10 times of volumes, remove organic solvents, chloroform, obtain the nano-micelle of described Double-mode imaging.
Embodiment 12
Double-mode imaging nano-micelle of the present invention, by following method, prepare:
CT preparation: NPAPF:PLGA-PEG is dissolved in dichloromethane according to the mass ratio of 1:1:8;
The dichloromethane solution of gained is mixed with the PBS buffer of 10 times of volumes, remove organic solvent dichloromethane, obtain the nano-micelle of described Double-mode imaging.
Embodiment 13
Double-mode imaging nano-micelle of the present invention, by following method, prepare:
CT preparation: NPAPF:DSPE-PEG is dissolved in dichloromethane according to the mass ratio of 1:1:8;
The dichloromethane solution of gained is mixed with the PBS buffer of 10 times of volumes, remove organic solvent dichloromethane, obtain the nano-micelle of described Double-mode imaging.
Embodiment 14
Double-mode imaging nano-micelle of the present invention, by following method, prepare:
By CT preparation: NPAPF:PEG-NH
2according to the mass ratio of 1:1:8, be dissolved in chloroform;
The chloroformic solution of gained is mixed with the glucose for injection solution of 10 times of volumes, remove organic solvents, chloroform, obtain the nano-micelle of described Double-mode imaging.
Embodiment 15
Double-mode imaging nano-micelle of the present invention, by following method, prepare:
CT preparation: NPAPF:PGA-PEG is dissolved in chloroform according to the mass ratio of 1:1:8;
The chloroformic solution of gained is mixed with the glucose for injection solution of 10 times of volumes, remove organic solvents, chloroform, obtain the nano-micelle of described Double-mode imaging.
Embodiment 16
Double-mode imaging nano-micelle of the present invention, by following method, prepare:
CT preparation: NPAPF:PEG-OPSS is dissolved in dichloromethane according to the mass ratio of 1:1:8;
The dichloromethane solution of gained is mixed with the glucose for injection solution of 10 times of volumes, remove organic solvent dichloromethane, obtain the nano-micelle of described Double-mode imaging.
Embodiment 17
Double-mode imaging nano-micelle of the present invention, by following method, prepare:
CT preparation: NPAPF:PEG-COOH is dissolved in dichloromethane according to the mass ratio of 1:1:8;
The dichloromethane solution of gained is mixed with the glucose for injection solution of 10 times of volumes, remove organic solvent dichloromethane, obtain the nano-micelle of described Double-mode imaging.
Embodiment 18
Double-mode imaging nano-micelle of the present invention, by following method, prepare:
Similar embodiment 2-17 preparation method, wherein the mass ratio of CT preparation and bag carrier material is 1:9.
Embodiment 19
Double-mode imaging nano-micelle of the present invention, by following method, prepare:
Similar embodiment 2-17 preparation method, wherein the mass ratio of CT preparation and bag carrier material is 1:10.
Embodiment 20
Double-mode imaging nano-micelle of the present invention, by following method, prepare:
Similar embodiment 2-17 preparation method, wherein CT preparation and NPAPF mass ratio are 1:2.
Embodiment 21
Double-mode imaging nano-micelle of the present invention, by following method, prepare:
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 Double-mode imaging nano-micelle of the present invention is analyzed.As shown in Figure 3.The Double-mode imaging nano-micelle culture fluid of 6 kinds of variable concentrations of configuration carries out cell culture, and detects its cell survival rate.Under the condition of higher concentration 60 μ g/mL Double-mode imaging nano-micelles, cell survival rate is still more than 80%, and along with concentration increases, survival rate downward trend is slow.Illustrate that Double-mode imaging nano-micelle toxicity of the present invention is low, good biocompatibility.
Embodiment 23
After tumor-bearing mice injection 24h, tumor locus Double-mode imaging detects
Adopt tail vein injection mode that 200 μ L Double-mode imaging nano-micelle of the present invention is injected in the Mice Body of lotus tumor, 0h and 24h use multispectral small animal living body imaging system and computed tomographic scanner (CT) to carry out fluorescence to mouse tumor position simultaneously and CT imaging detects.Mice fluorogram and the CT figure of gained are shown in Fig. 4 and Fig. 5.Common fluorescence molecule and contrast agent persistent period are generally no more than 6h, and Double-mode imaging nano-micelle preparations of the present invention is when injection detects after 24h, still have very strong fluorescence and CT signal, and tumor-targeting is very good.
Embodiment 24
Tumor-bearing mice organ Double-mode imaging detects
Adopt tail vein injection mode that the Double-mode imaging nano-micelle of the present invention of 200 μ L is injected in tumor-bearing mice body, after 24h, use multispectral small animal living body imaging system and computed tomographic scanner (CT) to carry out fluorescence and CT imaging detection to mouse lymph nodes, liver, spleen, kidney and other organs simultaneously.Mice organ targeting fluorogram and the CT figure of gained are shown in Fig. 6 and Fig. 7.From fluorogram 6, Double-mode imaging nano-micelle of the present invention is all very good to the fluorescence of organ and CT imaging effect, has only successfully realized by a shot, when can carry out two kinds of mode imagings, detects.
Applicant's statement, the present invention illustrates detailed method of the present invention by above-described embodiment, but the present invention is not limited to above-mentioned detailed method, does not mean that the present invention must rely on above-mentioned detailed method and could implement.Person of ordinary skill in the field should understand, any improvement in the present invention, to the selection of the interpolation of the equivalence replacement of each raw material of product of the present invention and auxiliary element, concrete mode etc., within all dropping on protection scope of the present invention and open scope.
Claims (10)
1. a Double-mode imaging nano-micelle, it comprises CT contrast agent, HONGGUANG fluorescence molecule NPAPF and described CT contrast agent and NPAPF bag is loaded in to the bag carrier material in described Double-mode imaging nano-micelle.
2. Double-mode imaging nano-micelle according to claim 1, is characterized in that, the mass ratio of described CT preparation and NPAPF is 1:1-1:3; Described CT preparation and described bag carrier material mass ratio are 1:8-1:15.
3. Double-mode imaging nano-micelle according to claim 1 and 2, is characterized in that, described CT contrast agent is the mixture of a kind of in Operand, barium sulfate and gold grain or at least two kinds.
4. according to the Double-mode imaging nano-micelle described in claim 1-3 any one, it is characterized in that, described bag carrier material is PGA-PEG, DSPE-PEG, PLGA-PEG, PEG-NH
2, a kind of in PEG-COOH, PEG-OPSS, PCL-PEG, TPGS, HS15 and phospholipid or at least two kinds mixture.
5. according to the preparation method of the Double-mode imaging nano-micelle described in claim 1-4 any one, it is characterized in that, comprise the following steps: bag carrier material, CT contrast agent and NPAPF are dissolved in to organic solvent, add aqueous solvent and mix, remove organic solvent, obtain described Double-mode imaging nano-micelle.
6. according to the preparation method of the Double-mode imaging nano-micelle described in claim 1-4 any one, it is characterized in that, comprise the following steps: bag carrier material, CT contrast agent, NPAPF are dissolved in to organic solvent, remove organic solvent, add aqueous solvent aquation, obtain described Double-mode imaging nano-micelle.
7. according to the preparation method described in claim 5 or 6, it is characterized in that, described organic solvent is the mixture of a kind of in chloroform, dichloromethane, acetone, ethanol and methanol or at least two kinds;
Preferably, described aqueous solvent is the mixture of a kind of in deionized water, PBS buffer, normal saline, glucose injection and amino acid injection or at least two kinds.
8. according to the preparation method described in claim 5 or 6, it is characterized in that, described in remove method that organic solvent uses for solvent evaporation method, emulsion process, the combination of revolving a kind of in embrane method, dialysis, lyophilization or at least two kinds.
9. according to the preparation method described in claim 5 or 6, it is characterized in that, the volume of described aqueous solvent is 10-15 times of described organic solvent volume.
10. the purposes in preparation tumor and the agent of organ targeted imaging according to the Double-mode imaging nano-micelle described in right 1-4 any one.
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Cited By (4)
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| CN109135729A (en) * | 2018-06-28 | 2019-01-04 | 华南理工大学 | A kind of temperature response type luminescent gold nano-micelle and preparation method thereof and the application in visualization temperature detection |
| CN110075320A (en) * | 2019-04-24 | 2019-08-02 | 温州医科大学 | A kind of bimodal tracer targeting non-small cell lung cancer |
| CN110302399A (en) * | 2019-05-07 | 2019-10-08 | 牡丹江医学院 | A kind of targeting 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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| US20120288442A1 (en) * | 2011-05-11 | 2012-11-15 | Atomic Energy Council-Institute Of Nuclear Energy Research | Nuclear Imaging Method Using Molecular Target Detection Agent for Liver Fibrosis |
| 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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| US20120288442A1 (en) * | 2011-05-11 | 2012-11-15 | Atomic Energy Council-Institute Of Nuclear Energy Research | Nuclear Imaging Method Using Molecular Target Detection Agent for Liver Fibrosis |
| 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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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109135729A (en) * | 2018-06-28 | 2019-01-04 | 华南理工大学 | A kind of temperature response type luminescent gold nano-micelle and preparation method thereof and the application in visualization temperature detection |
| CN110075320A (en) * | 2019-04-24 | 2019-08-02 | 温州医科大学 | A kind of bimodal tracer targeting non-small cell lung cancer |
| CN110302399A (en) * | 2019-05-07 | 2019-10-08 | 牡丹江医学院 | A kind of targeting 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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| CN104117073B (en) | 2016-10-26 |
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