CN101757643A - Emulsion based on stabilizing agent, preparation method and application thereof - Google Patents
Emulsion based on stabilizing agent, preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses an emulsion based on stabilizing agent, a preparation method and application thereof, belonging to the technical field of biomedicine. Chemical coprecipitation method is carried out on polylactic acid and iron halide to prepare stabilizing agent; or 1-(3 dimethylamino propyl)3 ethyl carbodiimide and polymine are further adopted for modifying to obtain stabilizing agent; stabilizing agent is mixed with water phase and oil phase to prepare emulsion, and emulsion is applied gene vector, magnetic resonance imaging contrast agent or ultrasonic diagnosis contrast agent. The stabilizing agent prepared in the invention has better hydrophily, lipophilicity and magnetism, and has certain electropositivity after modification; the prepared emulsion has magnetism and electropositivity, and a potential to be used as contrast agent for magnetic gene vector and magnetic resonance imaging; the emulsion prepared by supplying sulfur hexafluoride also has a potential to be used as contrast agent for ultrasonic diagnosis.
Description
Technical field
The present invention relates to the Emulsion in a kind of biological medicine technology field and its production and use, specifically is a kind of Emulsion based on stabilizing agent and its production and use.
Background technology
Emulsion be a kind of drop of liquid phase be dispersed in another kind of with it formed heterogeneous mixture in complete inconsistent liquid phase.The objectionable intermingling of two kinds of liquid phases makes the two produce surface tension in the place that is in contact with one another, when a kind of liquid phase is dispersed in the another kind of liquid phase with the form of drop, the contact area of the two obviously increases, cause chemical potential energy to increase, and can be spontaneously between the drop collision and fusion free energy of covering the loss, therefore Emulsion is a kind of thermodynamic unstable system, and the preparation of stable emulsion need be created one deck kinetics barrier to stop their gathering between drop and drop.It is amphipathic that the use of surfactant just is that it has, can be stabilized in mutual exclusive biphase between, reduce surface tension, thereby reduce the free energy that loses in the Emulsion forming process.Yet the amphipathic of it also makes it can be adsorbed on the surface of any solid dielectric, influences the latter's wettability significantly, and this has limited the range of application of Emulsion to a certain extent, just skin is had certain stimulation such as the surfactant that uses in the cosmetics.
In recent years, micropartical is considered to replace surfactant and prepares stable emulsion, and this Emulsion that is prepared into as stabilizing agent with solids is called as Pickering Emulsion, commemorates his finder Mr.S.U.Pickering with this.Research and report about Pickering Emulsion are to emerge in an endless stream in recent years, and content relates to various aspects such as preparation and phenetic analysis.Pickering Emulsion also be applied to simultaneously produce and life in the middle of, as being used as binding agent, sealant and waterproof coating are used in the cosmetics such as shampoo and hair conditioner or the like.The solids that are used for stablizing Pickering Emulsion also must meet some requirements, their shape, and size and hydrophobicity etc. all have in various degree influence to the stability of Emulsion.Contact angle such as particle and drop is exactly one of hydrophobic feature, and contact angle is more little, shows that particle is easy of more the drop moistening, is not easy to stop the gathering between the drop more, and the Emulsion of formation is also unstable more.Have only the hydrophobic particle of part, that is to say and the contact angle of drop particles near 90 degree, just can be by the moistening respectively of mutual exclusive two kinds of liquid phases, thus be attached to the surface of drop better, stop its gathering, also just stablized Emulsion better.The particle that often is used at present to prepare Pickering Emulsion comprises silicate, aluminate, and titanate, sial, metal-oxide, carbon black, nitride, cadmium selenide etc., and major part is based on SiO
2The particle that makes up on the basis.
Summary of the invention
The objective of the invention is to overcome the deficiencies in the prior art, a kind of Emulsion based on stabilizing agent and its production and use is provided, can prepare and have the stabilizing agent of amphipathic property preferably, and has positive charge and magnetic, utilize the emulsion of the stabilizing agent preparation after modifying to have magnetic and electropositive, can be used as the contrast agent that magnetic genophore or nuclear magnetic resonance are used.
The present invention realizes by following technical scheme,
First aspect the present invention relates to a kind of stabilizing agent, and this stabilizing agent can be prepared by following method: get high molecular polymer and iron halide and adopt chemical coprecipitation to prepare magnetic nano-particle, be i.e. stabilizing agent;
Described preparation method specifically is meant: with FeCl
3And FeCl
2Be dissolved in the de aerated water preparation iron salt solutions; Get high molecular polymer and be dissolved in the de aerated water, get solution, this solution is mixed with iron salt solutions, get mixed solution; Mixed solution is placed ice-water bath, under nitrogen protection, carry out following operation while stirring: dropwise drip the aqueous solution of NaOH, when pH value is 10.5～11, stop titration, continue ice bath; With the solution oil bath, centrifugal under nitrogen protection, get supernatant, drying obtains stabilizing agent.
Second aspect, the present invention relates to a kind of method of modifying of aforementioned stable agent: after getting the mixing of MES solution and stirring of 1-(3-dimethylamino-propyl)-3-ethyl carbodiimide, described stabilizing agent and polymine, through the dialysis dried, get the positively charged stabilizing agent.
The third aspect the present invention relates to a kind of Emulsion based on stabilizing agent, and its component is: water, oil phase and described stabilizing agent.
Fourth aspect the present invention relates to a kind of Emulsion based on the positively charged stabilizing agent, and this Emulsion is the emulsion of W/O/W structure, and its component is: water, oil phase and described positively charged stabilizing agent.
The 5th aspect the present invention relates to the preparation method of above-mentioned Emulsion based on the positively charged stabilizing agent, comprises the steps:
Preparation described in the step 2 is meant: react under lasting ultransonic environment.
The 6th aspect the present invention relates to the purposes of above-mentioned Emulsion, and this Emulsion is used to prepare genophore or magnetic resonance imaging contrast.
The 7th aspect the present invention relates to the preparation method of another kind based on the Emulsion of positively charged stabilizing agent, comprises the steps:
Preparation described in the step 2 is meant: react under lasting ultransonic environment;
Eight aspect the present invention relates to the purposes of above-mentioned Emulsion, and this Emulsion is used to prepare the purposes of ultrasonic diagnosis with contrast agent.
Compared with prior art, the present invention has following beneficial effect: the stabilizing agent of the present invention's preparation is a kind of solids, after composite modified with PEI, has amphipathic property preferably, and has positive charge and magnetic; Utilize the Emulsion of the stabilizing agent preparation of modified of the present invention to have magnetic and electropositive, can be used as the contrast agent that magnetic genophore or nuclear magnetic resonance are used; Simultaneously, ultrasonic limit, limit leads to sulfur hexafluoride gas in the process of preparation Emulsion, then can obtain containing the Emulsion of sulfur hexafluoride, and this Emulsion can be used as the novel type radiographic contrast of ultrasonic imaging diagnosis.
Description of drawings
Fig. 1 is the apparent figure of W/O colostrum and W/O/W emulsion;
Fig. 2 is observed W/O colostrum and W/O/W emulsion figure as a result under 40 times of optical microscopes;
Fig. 3 is the W/O/W emulsion and agarose gel electrophoresis figure after DNA combines;
Fig. 4 carries the effect comparative result of pGL3-control plasmid transfection COS-7 cell for the W/O/W emulsion;
Fig. 5 is external nuclear magnetic resonance (the T2 weighting phase) photo of W/O/W emulsion and stabilizing agent;
Fig. 6 is the aspect graph of W/O/W emulsion under TEM;
Fig. 7 is the external imaging results of W/O/W emulsion under diasonograph.
The specific embodiment
Below embodiments of the invention are elaborated, present embodiment is being to implement under the prerequisite with the technical solution of the present invention, provided detailed embodiment and concrete operating process, but protection scope of the present invention is not limited to following embodiment.
The experiment material that present embodiment relates to is as follows:
Ferrous chloride, iron chloride, sodium hydroxide is analytical pure, available from Shanghai chemical reagents corporation of Chinese Medicine group;
Polylactic acid (PLA) is visitd rich bio tech ltd available from Shanghai;
1-(3-dimethylamino-propyl)-3-ethyl carbodiimide (EDC) is available from Sigma company;
Polymine (PEI) 25000 is available from Sigma company;
Soybean oil, commercially available;
Sulfur hexafluoride (SF
6) gas is available from the red Ward kind of center gas limited company;
African green monkey kidney cell line COS-7 cell is available from ATCC;
RPMI-1640 culture medium and serum are all available from GIBICO company;
Luciferase report plasmid pGL3-control is available from U.S. Promega company;
The PCS plasmid is open in Chinese invention patent application CN101095951 prospectus;
The luciferase detection kit is available from U.S. Promega company;
BCA protein quantification test kit is available from Shanghai industry Lik-Sang thing technology company;
The stabilizing agent preparation method of present embodiment is as follows:
Take by weighing 730mg FeCl
3With 360mg FeCl
2Be dissolved in the 5ml de aerated water, get iron salt solutions; Get the PLA of 2.8g afterwards, be dissolved in the 2ml de aerated water, get solution, this solution is mixed with iron salt solutions, get mixed solution; Mixed solution is placed ice-water bath (2～4 ℃), carry out following operation while stirring under nitrogen protection: dropwise drip the aqueous solution of NaOH (5M), pH meter on-line monitoring pH value stops titration when pH value is 10.5～11, continues ice bath 30 minutes; Under nitrogen protection,, make the granule ripening with 85 ℃ of oil bath heating of solution 2 hours; After reaction finishes, 9000rpm, 4 ℃ centrifugal 10 minutes, remove bulky grain precipitation, keep supernatant, similarity condition recentrifuge 10 minutes further removes the bulky grain precipitation, keeps supernatant, obtains the magnetic particle solution of about 10ml; Further, can obtain magnetic nano-particle solid (being the MP-PLA magnetic particle), i.e. stabilizing agent by the drying of dialysing.
The method of preparing emulsion of present embodiment is as follows:
Utilize the ultrasonic preparation of aforementioned stable agent W/O Emulsion: get the solution (being the stock solution of PLA magnetic particle) that dialysis obtains, dilute 5 times after, get 100ul and mix with the 900ul soybean oil, 25 ℃, 30% ultrasound intensity, ultrasonic 7 times, each 5S on, 6S off, the Emulsion of W/O.
Present embodiment adopts with embodiment 1 identical materials and step and prepares stabilizing agent, and prepares the method for Emulsion based on described stabilizing agent, specifically comprises the steps:
Utilize the ultrasonic preparation of aforementioned stable agent O/W Emulsion: get the solution (being the stock solution of PLA magnetic particle) that dialysis obtains, dilute 5 times after, get 900ul and mix with the 100ul soybean oil, 25 ℃, 30% ultrasound intensity, ultrasonic 7 times, each 5S on, 6S off, the Emulsion of O/W.
Present embodiment adopts the stabilizing agent for preparing positively charged with embodiment 1 identical materials, and this preparation method specifically comprises the steps:
Take by weighing 730mg FeCl
3With 360mg FeCl
2Be dissolved in the 5ml de aerated water, get iron salt solutions; Get the PLA of 2.8g afterwards, be dissolved in the 2ml de aerated water, get solution, this solution is mixed with iron salt solutions, get mixed solution; Mixed solution is placed ice-water bath (2～4 ℃), carry out following operation while stirring under nitrogen protection: dropwise drip the aqueous solution of NaOH (5M), pH meter on-line monitoring pH value stops titration when pH value is 10.5～11, continues ice bath 30 minutes; Under nitrogen protection,, make the granule ripening with 85 ℃ of oil bath heating of solution 2 hours; After reaction finishes, 9000rpm, 4 ℃ centrifugal 10 minutes, remove bulky grain precipitation, keep supernatant, similarity condition recentrifuge 10 minutes further removes the bulky grain precipitation, keeps supernatant, obtains the magnetic particle solution of about 10ml; Further, can obtain the magnetic nano-particle solid by drying;
PEI25000 is dissolved in the MES solution (0.05M MES, 0.5M NaCl) of pH6.0, makes that the final concentration of PEI25000 is 0.1667g/ml, get the MES solution of PEI; Get the magnetic particle solution of 400ul step 1 gained, the MES solution of 240ul PEI, 80ulEDC, mix, stirring reaction is 2 hours under the room temperature, afterwards solution is placed molecular weight 10, dialyse 4 hours in 0000 the bag filter to remove free PEI and EDC, obtain the stock solution of MP-PLA-EDC-PEI magnetic particle, drying gets stabilizing agent.
The method of preparing emulsion of present embodiment comprises the steps:
Implementation result
(1) phenetic analysis of the magnetic particle before and after being connected with PEI
Get magnetic particle (MP-PLA) and stabilizing agent (MP-PLA-EDC-PEI), get equal-volume deionized water ddH respectively
2Carry out Zeta potential and particle diameter detection after the O dilution, the results are shown in Table 1, therefrom as can be seen, with respect to MP-PLA, it is big that the particle diameter of MP-PLA-EDC-PEI becomes, surface potential is also just being become by negative, illustrate that PEI has been connected the surface of MP-PLA, because the part carboxyl reaction on itself and the PLA, so make the negative charge on magnetic particle surface reduce, cause particle accumulation, it is big that particle diameter becomes; Simultaneously, make the MP-PLA-EDC-PEI surface have numerous amino, so surface potential is for just again because PEI is connected to the MP-PLA surface.
Table 1
| ??MP-PLA | ??MP-PLA-EDC-PEI | ??W/O/W??multi-emulsion | |
| ??particle??size | ??34nm | ??1.59um | ??140.4nm |
| ??Zeta??potential | ??-34.1mv | ??40.8mv | ??55.5mv |
(2) the apparent pattern and the study on the stability of Emulsion
With ordinary camera and optical microscope the apparent pattern of colostrum and emulsion is observed.Ordinary camera the results are shown in Figure 1, and A is oil phase and the water before colostrum forms, and B is the W/O colostrum, and C is the W/O/W emulsion; With PBS colostrum is diluted 5 times respectively then, emulsion is observed under 40 times of optical microscopes after diluting 40 times, the results are shown in Figure 2, A is the colostrum after diluting, B is the emulsion after diluting, as can be seen, the apparent homogeneous that all compares of formed colostrum and emulsion, it is more stable that light microscopic is observed the emulsion droplet form down, the emulsion droplet particle size distribution of emulsion is homogeneous more, and can see the situation of the little emulsion droplet of cover in a lot of big emulsion droplets, and the emulsion that has formed W/O/W really is described, also further proof only just can form relatively stable emulsion with the MP-PLA-EDC-PEI magnetic particle as stabilizing agent under the situation that does not add any surfactant.Emulsion at room temperature leaves standstill, and can stablize 48 hours, be divided into gradually then two-layer, but up and down two-layer boundary is still very fuzzy, is still emulsion, just the upper oil phase ratio is big, lower layer of water phase ratio is big; Its dilution was left standstill 36 hours after 100 times, and observation still can be seen finely dispersed emulsion droplet under the optical microscope.Above evidence shows that the emulsion stability of the stabilizing agent preparation that utilizes present embodiment is better.
(3) the W/O/W emulsion is external in conjunction with the DNA ability
Be placed on 10 with after 10 times of the emulsion dilutions; in 0000 the bag filter; dialysis is 4 hours in PBS; get then emulsion after the 2ul dialysis after 5 times of dilutions respectively with 0.5,1,1.5,2,2.5,3,3.5, the PCS plasmid of the 1.25ug/ul of 4ul mixes; leave standstill under the room temperature and go up the sample electrophoresis after 10 minutes, and get the 1ulPCS plasmid in contrast.0.8% agarose gel, 80V, electrophoresis 20 minutes is observed under gel imaging system then and is taken pictures, and finds the bonded optimal proportion of emulsion and DNA.Agarose gel electrophoresis the results are shown in Figure 3, track after band 1～9 represents the PCS plasmid of 1.25ug/ul of 2ul emulsion and 0.5,1,1.5,2,2.5,3,3.5,4ul compound respectively, as can be seen, preceding 4 swimming lanes almost do not have the appearance of band, the DNA band has then appearred in all the other swimming lanes, the PCS plasmid that this explanation 2ul emulsion can compound 2ul.
(4) the outer-gene transfection of W/O/W emulsion
According to 2*10
4The density of individual cells/well evenly is inoculated in 24 orifice plates with the COS-7 cell, cultivate after 16 hours, 1640 culture medium that change serum-free into continue to cultivate 4 hours, same then in 1640 culture medium of serum-free, product after compound carries out transfection to the Emulsion that every hole adds different volumes (0.1,0.2,0.3,0.4ul) with the pGL3-control plasmid of 3ul 0.4ug/ul, the PEI of 0.024ul0.1667g/ml equally and the pGL3-control plasmid of 3ul 0.4ug/ul compound as positive control; 4 parallel holes of each concentration, transfection 3.5 hours.After removing supernatant, changing the culture medium that contains 10% serum into continues to cultivate 24 hours, remove culture fluid then, wash cell twice with PBS, reuse lysate cell lysis, 130ul lysate/hole, 37 ℃, cracking 0.5 hour is got the 10ul lysate then and is mixed with the 10ulLuciferace substrate mixture, and illumination meter detects down.The results are shown in Figure 4,, can carry exogenous gene with the MP-PLA-EDC-PEI magnetic particle as the emulsion of the W/O/W of stabilizing agent preparation the cos-7 cell is carried out in-vitro transfection, and have certain transfection efficiency from transfection results.In four different Emulsion concentration, the transfection effect of 0.2ul is best, illustrates that also there is certain toxicity in this Emulsion, only finds suitable N/P, just can reach best transfection effect.
(5) external magnetic resonance (MRI) imaging of W/O/W emulsion
Get stabilizing agent stock solution and W/O/W emulsion stock solution respectively, carry out suitably doubling dilution with deionized water, obtain a series of different ferrum element steady concentration dilution agent liquid and W/O/W emulsion diluents of containing. use the 3T MRI scanner (TrioTim) of Siemens Company to detect the MRI signal intensity (T2 weighting phase) of above-mentioned sample then.Used parameter is: 20 ℃, and 3T, spin-ethosequence, TR are 8000ms, TE sees Fig. 5 for the 19ms. concrete outcome.A is stabilizing agent MP-PLA-EDC-PEI, and B is the W/O/W emulsion.Therefrom as can be seen, within the specific limits, for a given ferrum element concentration, the W/O/W emulsion is compared with stabilizing agent MP-PLA-EDC-PEI, demonstrate darker image relatively, that is to say that the W/O/W emulsion can increase the contrast of image relatively more strongly, have the potentiality of the contrast agent that becomes magnetic resonance (MRI) imaging.
(6) preparation contains SF
6The W/O/W emulsion
Prepare the W/O colostrum according to the method in the method for preparing emulsion step 1, with after 6 times of the stock solution of the MP-PLA-EDC-PEI magnetic particle dilutions, get 450ul as outer water afterwards, 50ul W/O colostrum is that the limit leads to SF after the two mixes as interior water
6The limit continues ultrasonic (100W), and ventilate respectively 2min and 5min promptly obtain the emulsion of two kinds of gassiness.TEM (transmission electron microscope) observes down after diluting 50 times, and more different duration of ventilation are to the influence of the pattern of the emulsion droplet of the emulsion that forms, and with the ultrasound measuring instrument of hospital detect in the emulsion emulsion droplet gassiness whether and air content how much.
Fig. 6 is the aspect graph of W/O/W emulsion under TEM; The emulsion emulsion droplet under TEM that can see short duration of ventilation (2min) formation is generally very little, and particle diameter is about 100～200nm, and emulsion droplet shortage third dimension, sees Fig. 6 A, Fig. 6 B; The emulsion that long duration of ventilation (5min) forms is observed then most of emulsion droplet under TEM generally bigger, and particle diameter is 500nm～1um, and emulsion droplet is generally spherical in shape, and third dimension is very strong, sees Fig. 6 C, Fig. 6 D.Contrast by two kinds of emulsions has proved SF
6Gas is enclosed in the middle of the emulsion droplet, makes emulsion droplet become big, and darker around brighter in the middle of the emulsion droplet, also illustrates that the outer surface that the MP-PLA-EDC-PEI magnetic particle wraps in emulsion droplet has played function of stabilizer simultaneously.Ultrasound measuring instrument detects, and adopts the pattern of CPS MSK, the frequency of 14.0MHz.The emulsion that ventilation 2min forms is observed under the external supersonic pattern, and it is just fewer just to have begun bubble, continues that development effect weakens gradually under the ultrasound condition, probably can keep about 6min, sees Fig. 7 A, Fig. 7 B; And the emulsion that ventilation 5min forms is under the external supersonic pattern, and then bubble is just than comparatively dense at the beginning, and development effect probably can be kept about 10min under lasting ultrasound condition, sees Fig. 7 C, Fig. 7 D, and this illustrates SF
6Gas has been enclosed in the middle of the emulsion droplet of emulsion, and the emulsion that forms has the potentiality that become ultrasonic diagnosis usefulness contrast agent.
Claims (12)
1. the preparation method of a stabilizing agent is characterized in that, gets high molecular polymer and iron halide and adopts chemical coprecipitation to prepare magnetic nano-particle, be i.e. stabilizing agent.
2. the preparation method of stabilizing agent according to claim 1 is characterized in that, described preparation method specifically is meant: with FeCl
3And FeCl
2Be dissolved in the de aerated water preparation iron salt solutions; Get high molecular polymer and be dissolved in the de aerated water, get solution, this solution is mixed with iron salt solutions, get mixed solution; Mixed solution is placed ice-water bath, under nitrogen protection, carry out following operation while stirring: dropwise drip the aqueous solution of NaOH, when pH value is 10.5～11, stop titration, continue ice bath; With the solution oil bath, centrifugal under nitrogen protection, get supernatant, drying gets stabilizing agent.
3. the method for modifying of a stabilizing agent according to claim 1, it is characterized in that, after getting the mixing of MES solution and stirring of 1-(3-dimethylamino-propyl)-3 ethyl carbodiimide, described stabilizing agent and polymine,, get the positively charged stabilizing agent through the dialysis dried.
4. the synthetic Emulsion of stabilizing agent that preparation method according to claim 1 obtains is characterized in that, this Emulsion is water in oil emulsion or oil in water emulsion, and its component is: water, oil phase and described stabilizing agent.
5. the purposes of an Emulsion according to claim 4 is characterized in that, this Emulsion is used to prepare magnetic resonance imaging contrast.
6. the synthetic Emulsion of positively charged stabilizing agent that method of modifying according to claim 3 obtains is characterized in that this Emulsion is the emulsion of W/O/W structure, and its component is: water, oil phase and described positively charged stabilizing agent.
7. the preparation method of Emulsion according to claim 6 is characterized in that, comprises the steps:
Step 1 adopts ultrasonic method to prepare the colostrum of oil-in-water structure;
Step 2 is utilized the colostrum of oil-in-water structure and the emulsion that the positively charged stabilizing agent prepares the W/O/W structure, i.e. Emulsion.
8. the preparation method of Emulsion according to claim 7 is characterized in that, the preparation described in the step 2 is meant: react under lasting ultransonic environment.
9. the purposes of an Emulsion according to claim 6 is characterized in that, this Emulsion is used to prepare genophore.
10. the synthetic Emulsion of positively charged stabilizing agent that method of modifying according to claim 3 obtains is characterized in that this Emulsion is the emulsion of W/O/W structure, and its component is: water, oil phase, described positively charged stabilizing agent and sulfur hexafluoride.
11. the preparation method of an Emulsion according to claim 10 is characterized in that, comprises the steps:
Step 1 adopts ultrasonic method to prepare the colostrum of oil-in-water structure;
Step 2 is utilized the colostrum and the positively charged stabilizing agent of oil-in-water structure, at the emulsion that continues to feed preparation W/O/W structure under the condition of sulfur hexafluoride, i.e. Emulsion.
12. the purposes of an Emulsion according to claim 10 is characterized in that, this Emulsion is used to prepare the ultrasonic diagnosis contrast agent.
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| CN108333343A (en) * | 2017-01-19 | 2018-07-27 | 深圳市新产业生物医学工程股份有限公司 | Immune magnetic compound, preparation method including its antigen capture agent, kit, system and application |
| CN109568591A (en) * | 2019-01-14 | 2019-04-05 | 中国科学院化学研究所 | A kind of software micro-nano motor and preparation method thereof |
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| CN101474414A (en) * | 2009-02-06 | 2009-07-08 | 上海师范大学 | Preparation and application of polymer-coated magnetic nanoparticle contrast agent |
| US20100008854A1 (en) * | 2008-07-11 | 2010-01-14 | Seung Joo Haam | Metal nanocomposite, preparation method and use thereof |
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| US20100008854A1 (en) * | 2008-07-11 | 2010-01-14 | Seung Joo Haam | Metal nanocomposite, preparation method and use thereof |
| CN101474414A (en) * | 2009-02-06 | 2009-07-08 | 上海师范大学 | Preparation and application of polymer-coated magnetic nanoparticle contrast agent |
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| Title |
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| 《中国优秀博硕士学位论文全文数据库 (博士) 医药卫生科技辑》 20070615 刘书朋 磁性纳米颗粒的制备及其在药物作用靶点生物淘洗中的应用 , 第06 期 2 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108333343A (en) * | 2017-01-19 | 2018-07-27 | 深圳市新产业生物医学工程股份有限公司 | Immune magnetic compound, preparation method including its antigen capture agent, kit, system and application |
| CN109568591A (en) * | 2019-01-14 | 2019-04-05 | 中国科学院化学研究所 | A kind of software micro-nano motor and preparation method thereof |
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