CN107722190A - A kind of polymer with Thermo-sensitive, preparation method and its application on the microballoon with Thermo-sensitive magnetic is prepared - Google Patents
A kind of polymer with Thermo-sensitive, preparation method and its application on the microballoon with Thermo-sensitive magnetic is prepared Download PDFInfo
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Abstract
The present invention relates to a kind of polymer with Thermo-sensitive, preparation method and its application on the microballoon with Thermo-sensitive magnetic is prepared, catechol group and the monomer NIPAM with temperature-responsive are introduced simultaneously first with radical polymerization, obtain the polymer with Thermo-sensitive, make temperature sensing polymer coated magnetic nano-particle by catechol again, the microballoon with Thermo-sensitive magnetic is prepared.This method has potential advantages in medicament transport and insoluble drug release etc..
Description
Technical field
The invention belongs to hybrid nano-material field, more particularly to a kind of polymer with Thermo-sensitive, preparation method
And its application on the microballoon with Thermo-sensitive magnetic is prepared.
Background technology
Polymer as carrier targeted drug system in medical science, pharmaceutically cause extensive concern.Polyethyleneglycol
Methyl ether methacrylate (PMAPEG) has the unique texture of different carbon chain double bond and ester group, and has the structure of similar crown ether
Characteristic, therefore in terms of biomaterial for medical purpose, there is preferable biocompatibility.Poly-N-isopropyl acrylamide (PNIPAM) is
A kind of effective temperature sensing polymer, its lowest critical solution temperature (LCST) are 32 DEG C, close to 37 DEG C of human body temperature, work as the external world
When temperature is higher than lowest critical solution temperature, NIPAM shows hydrophobicity, conversely, it is then hydrophilic, therefore often utilize temperature change pair
The change of its form carrys out Drug controlled release.PMAPEG is combined with PNIPAM copolymerization, can obtain the pharmaceutical carrier of certain performance,
But drug utilization is inefficient, and toxic side effect be present.
In addition, to reduce medicine loss unnecessary in transportation, the machine that toxic side effect kills normal cell is reduced
Rate, improves the effectiveness of medicine, and the 1970s, Pilwat and Widder etc. proposed the concept of magnetic control targeted drug delivery system,
Have become the weight of domestic and international cancer therapy drug dosage form research by the use of magnetic medicinal microglobule as a kind of new targeting drug delivery system
Point and focus.Moreover, since scientist contains substantial amounts of L-3,4 dihydroxyphenylalanine and lysine residue in marine mussel protein secretion liquid, can
The surface of different types of organic and inorganic materials is depended in a humid environment, and so far, catechol and its derivative are
Researcher is caused widely to pay close attention to.3,4- 4-dihydroxy benzaldehydes have good adhesion energy because it contains catechol group
Power, then combined with other functional monomers, its advantage is played to a greater extent.But so far, do not have also a kind of using adjacent
Resorcinol groups introduce the method that magnetic nano-particle prepares pharmaceutical carrier in PMAPEG and PNIPAM copolymerization conjugate.
The content of the invention
It is an object of the invention in place of overcome the deficiencies in the prior art, there is provided a kind of polymer with Thermo-sensitive,
Preparation method and its application on the microballoon with Thermo-sensitive magnetic is prepared, introduce simultaneously in temperature sensing polymer adsorbable
The catechol group of magnetic nano-particle and the NIPAM monomers with temperature-responsive, recycle the temperature sensing polymer system
The standby microballoon with Thermo-sensitive magnetic, can be used as pharmaceutical carrier, be expected to improve the medicinal efficiency of such drug-carrying polymer, reduce poison
Side effect, new approaches are provided for effective control of insoluble drug release material.
One of the technical solution adopted for the present invention to solve the technical problems is：
A kind of polymer with Thermo-sensitive, the structure of the polymer are shown below：
Wherein, x: y: z=1: (1~10): (1~20), the polymer relative molecular weight are 10000~100000.
The two of the technical solution adopted for the present invention to solve the technical problems are：
A kind of method for preparing the above-mentioned polymer with Thermo-sensitive, comprises the following steps：By 4- methacryl amidos
Aniline, NIPA, polyethylene glycol monomethyl ethermethacrylic acid esters and initiator are dissolved in the first solvent, 60~
80 DEG C, under nitrogen protection, 20~30h of stirring reaction, obtained by the preparation method of radical polymerization described with Thermo-sensitive
Polymer；Wherein, the 4- methacryls amido aniline, NIPA, poly glycol monomethyl ether metering system
The mol ratio of acid is 1: 1~20: 1~50；The dosage of the initiator is 4- methacryl amidos aniline, N- isopropyl propylene
The 0.1~5% of acid amides, poly glycol monomethyl ether methacrylic acid gross mass.
The three of the technical solution adopted for the present invention to solve the technical problems are：
A kind of method for preparing the microballoon with Thermo-sensitive magnetic using the above-mentioned polymer with Thermo-sensitive, including：
1) by 4- methacryl amidos aniline, NIPA, polyethylene glycol monomethyl ethermethacrylic acid esters
It is dissolved in the first solvent with initiator, under 60~80 DEG C, nitrogen protection, 20~30h of stirring reaction, obtains described with temperature sensitive
The polymer of property；The polymer for coating nano-particle with Thermo-sensitive is obtained by the preparation method of radical polymerization；Its
In, the 4- methacryls amido aniline, NIPA, the mol ratio of poly glycol monomethyl ether methacrylic acid
For 1: 1~20: 1~50；The dosage of the initiator is 4- methacryl amidos aniline, NIPA, poly- second
The 0.1~5% of glycol monomethyl ether methacrylic acid gross mass；
2) it is dispersed in the second solvent by being ultrasonically treated 20~60min magnetic nano-particle, then will
The second solvent for being dispersed with magnetic nano-particle is added dropwise in water dropwise, is uniformly dispersed, is obtained mixed solution；Step 1) is made
The polymer with Thermo-sensitive obtained is dissolved in the second solvent, is added dropwise to dropwise in the mixed solution；Wherein described magnetic is received
The mass ratio of rice corpuscles and the polymer with Thermo-sensitive is 0.1~1：1~10；Then 3~10h is ultrasonically treated, is made second molten
Agent volatilization is complete, obtains the polymer microballoon for being coated with magnetic nano-particle, is the microballoon with Thermo-sensitive magnetic.
The microballoon with Thermo-sensitive magnetic, i.e. schematic diagram after temperature sensing polymer coated magnetic nano-particle are as schemed
Shown in 1, wherein, spheroid placed in the middle is magnetic nano-particle (such as magnetic ferroferric oxide nano-particles), and surrounding bead is neighbour
Resorcinol groups, straightway PMAPEG, curved section PNIPAM.
In one embodiment, first solvent is at least one in tetrahydrofuran, dichloromethane, ether, absolute ethyl alcohol etc.
Kind；The quality of first solvent is 4- methacryl amidos aniline, NIPA, poly glycol monomethyl ether first
5~30 times of base acrylate and initiator gross mass；
In one embodiment, the initiator is azodiisobutyronitrile (AIBN), dibenzoyl peroxide (BPO), azo two
At least one of different heptonitrile (ABVN) etc..
In one embodiment, second solvent is at least one in tetrahydrofuran, dichloromethane, ether, absolute ethyl alcohol etc.
Kind；The magnetic nano-particle, the rate of charge with the polymer of Thermo-sensitive, the second solvent and water are 0.1~1mg：1~
10mg：1~5ml：5~10ml.
In one embodiment, the magnetic nano-particle is that magnetic ferroferric oxide nano-particles and/or magnetic iron oxide are received
Rice corpuscles.
In one embodiment, the preparation method of the magnetic ferroferric oxide nano-particles includes：By (NH4)2Fe(SO4)2·
6H2O is dissolved in distilled water, obtains Fe2+Presoma；By Fe2+Presoma adds and is mixed with the uniform molten of oleic acid, sodium hydroxide and ethanol
In liquid, stirring to the aobvious brown of precipitation；Brown mixture is heated into 8~12h at 180~200 DEG C；Room temperature is finally cooled to, is obtained
Obtain magnetic ferroferric oxide nano-particles.
The four of the technical solution adopted for the present invention to solve the technical problems are：
A kind of use of microballoon with Thermo-sensitive magnetic prepared according to three method of technical scheme as pharmaceutical carrier
On the way, such as medicine sustained and controlled release carrier, or medicament transport carrier.
The microballoon with Thermo-sensitive magnetic, i.e., in aqueous environment after temperature sensing polymer coated magnetic nano-particle
As shown in Fig. 2 when ambient temperature is higher than lowest critical solution temperature, NIPAM shows hydrophobic the schematic diagram of middle release medicine
Property, medicine is by polymer overmold；Conversely, when ambient temperature is less than lowest critical solution temperature, NIPAM shows hydrophily,
Insoluble drug release.
Beneficial effects of the present invention are as follows：
1st, the present invention reacts to obtain monomer containing catechol group using amino-compound, can effectively adsorb ferroso-ferric oxide
Deng nano-particle.
2nd, present invention introduces NIPAM monomers, make polymer while there is magnetic and Thermo-sensitive.
3rd, present invention can apply in cancer therapy drug, utilize magnetic and medicated mobile performance, induced by magnetic field performance and temperature
Response, effective Drug controlled release, it can reach efficient, less toxic effect.
Brief description of the drawings
The invention will be further described with reference to the accompanying drawings and examples.
Fig. 1 is the structural representation of the microballoon with Thermo-sensitive magnetic of the present invention, wherein, spheroid placed in the middle is received for magnetic
Rice corpuscles (such as magnetic ferroferric oxide nano-particles), surrounding bead are catechol group, straightway PMAPEG, curve
Section is PNIPAM
Fig. 2 is that the microballoon with Thermo-sensitive magnetic of the present invention discharges the schematic diagram of medicine in aqueous environment.
Embodiment
Present disclosure is illustrated below by embodiment：
Embodiment 1
(1) synthesis of the polymer with Thermo-sensitive：
In 100mL reaction vessel, 1.76g 4- methacryl amidos aniline, 2.26g N- isopropyl propylene are added
Acid amides, 9.50g polyethylene glycol monomethyl ethermethacrylic acid esters and 150mg AIBN, are dissolved in 30mL tetrahydrofuran, at 70 DEG C
Under the protection of lower and nitrogen, stirring reaction 24h.Reaction terminates rear reaction solution precipitation purification in hexane, obtains described with temperature sensitive
Property polymer, wherein, x: y: z=1: 1: 2, the polymer relative molecular weight be 12400.
(2) synthesis of magnetic ferroferric oxide nano-particles：
By (NH4)2Fe(SO4)2·6H2O is dissolved in 20ml distilled water, obtains 0.002mol Fe2+Presoma；In room temperature
Under, 10mL oleic acid, 1g sodium hydroxides and 10mL ethanol are mixed, stirred；By Fe2+Presoma is added in the homogeneous solution,
Stirring to precipitation shows brown；Brown mixture is transferred in 50mL autoclaves, and 10h is heated at 180 DEG C；It is last cold
But to room temperature, the black product of container bottom is magnetic ferroferric oxide nano-particles.
(3) synthesis of polymer overmold magnetic ferroferric oxide nano-particles：
0.5mg magnetic ferroferric oxide nano-particles are added to ultrasonic 30min in 1.5mL tetrahydrofurans, treat magnetic four
After Fe 3 O nano-particle is uniformly dispersed, solution is added drop-wise in 6mL ultra-pure waters with needle tubing, ultrasonic 30min obtains scattered equal
Even ferroso-ferric oxide mixed solution；The polymer with Thermo-sensitive that 5mg steps (1) are prepared is dissolved in 1mL tetrahydrochysene furans
In muttering, after being completely dissolved, it is added dropwise in ferroso-ferric oxide mixed solution, ultrasonic 5h, after tetrahydrofuran volatilization completely, i.e.,
The polymer microballoon of coated magnetic ferriferrous oxide nano-particle can be obtained, is the microballoon with Thermo-sensitive magnetic.
Embodiment 2
(1) synthesis of the polymer with Thermo-sensitive：
In 100mL reaction vessel, 0.88g 4- methacryl amidos aniline, 2.26g N- isopropyl propylene are added
Acid amides, 7.12g polyethylene glycol monomethyl ethermethacrylic acid esters and 150mg AIBN, are dissolved in 30mL tetrahydrofuran, at 70 DEG C
Under the protection of lower and nitrogen, stirring reaction 24h.Reaction terminates rear reaction solution precipitation purification in hexane, obtains described with temperature sensitive
Property polymer, wherein, x: y: z=1: 2: 3, the polymer relative molecular weight be 15000.
(2) synthesis of magnetic ferroferric oxide nano-particles：
By (NH4)2Fe(SO4)2·6H2O is dissolved in 20ml distilled water, obtains 0.002mol Fe2+Presoma；In room temperature
Under, 10mL oleic acid, 1g sodium hydroxides and 10mL ethanol are mixed, stirred；By Fe2+Presoma is added in the homogeneous solution,
Stirring to precipitation shows brown；Brown mixture is transferred in 50mL autoclaves, and 10h is heated at 180 DEG C；It is last cold
But to room temperature, the black product of container bottom is magnetic ferroferric oxide nano-particles.
(3) synthesis of polymer overmold magnetic ferroferric oxide nano-particles：
0.5mg magnetic ferroferric oxide nano-particles are added to ultrasonic 30min in 1.5mL tetrahydrofurans, treat magnetic four
After Fe 3 O nano-particle is uniformly dispersed, solution is added drop-wise in 7mL ultra-pure waters with needle tubing, ultrasonic 30min obtains scattered equal
Even ferroso-ferric oxide mixed solution；The polymer with Thermo-sensitive that 6mg steps (1) are prepared is dissolved in 1.5mL tetrahydrochysenes
In furans, after being completely dissolved, it is added dropwise in ferroso-ferric oxide mixed solution, ultrasonic 5h, after tetrahydrofuran volatilization completely,
The polymer microballoon of coated magnetic ferriferrous oxide nano-particle can be obtained, is the microballoon with Thermo-sensitive magnetic.
Embodiment 3
(1) synthesis of the polymer with Thermo-sensitive：
In 100mL reaction vessel, 1.41g 4- methacryl amidos aniline, 3.62g N- isopropyl propylene are added
Acid amides, 3.80g polyethylene glycol monomethyl ethermethacrylic acid esters and 150mg AIBN, are dissolved in 30mL tetrahydrofuran, at 70 DEG C
Under the protection of lower and nitrogen, stirring reaction 24h.Reaction terminates rear reaction solution precipitation purification in hexane, obtains described with temperature sensitive
Property polymer, wherein, x: y: z=1: 2: 1, the polymer relative molecular weight be 13100.
(2) synthesis of magnetic ferroferric oxide nano-particles：
By (NH4)2Fe(SO4)2·6H2O is dissolved in 20ml distilled water, obtains 0.002mol Fe2+Presoma；In room temperature
Under, 10mL oleic acid, 1g sodium hydroxides and 10mL ethanol are mixed, stirred；By Fe2+Presoma is added in the homogeneous solution,
Stirring to precipitation shows brown；Brown mixture is transferred in 50mL autoclaves, and 10h is heated at 180 DEG C；It is last cold
But to room temperature, the black product of container bottom is magnetic ferroferric oxide nano-particles.
(3) synthesis of polymer overmold magnetic ferroferric oxide nano-particles：
0.5mg magnetic ferroferric oxide nano-particles are added to ultrasonic 30min in 1.5mL absolute ethyl alcohols, treat magnetic four
After Fe 3 O nano-particle is uniformly dispersed, solution is added drop-wise in 7mL ultra-pure waters with needle tubing, ultrasonic 30min obtains scattered equal
Even ferroso-ferric oxide mixed solution；It is anhydrous that the polymer with Thermo-sensitive that 6mg steps (1) are prepared is dissolved in 1.5mL
In ethanol, after being completely dissolved, it is added dropwise in ferroso-ferric oxide mixed solution, ultrasonic 5h, after absolute ethyl alcohol volatilization completely,
The polymer microballoon of coated magnetic ferriferrous oxide nano-particle can be obtained, is the microballoon with Thermo-sensitive magnetic.
Embodiment 4
(1) synthesis of the polymer with Thermo-sensitive：
In 100mL reaction vessel, 1.41g 4- methacryl amidos aniline, 1.81g N- isopropyl propylene are added
Acid amides, 7.60g polyethylene glycol monomethyl ethermethacrylic acid esters and 200mg AIBN, are dissolved in 30mL tetrahydrofuran, at 70 DEG C
Under the protection of lower and nitrogen, stirring reaction 24h.Reaction terminates rear reaction solution precipitation purification in hexane, obtains described with temperature sensitive
Property polymer, wherein, x: y: z=1: 1: 2, the polymer relative molecular weight be 13100.
(2) synthesis of magnetic ferroferric oxide nano-particles：
By (NH4)2Fe(SO4)2·6H2O is dissolved in 20ml distilled water, obtains 0.002mol Fe2+Presoma；In room temperature
Under, 10mL oleic acid, 1g sodium hydroxides and 10mL ethanol are mixed, stirred；By Fe2+Presoma is added in the homogeneous solution,
Stirring to precipitation shows brown；Brown mixture is transferred in 50mL autoclaves, and 10h is heated at 180 DEG C；It is last cold
But to room temperature, the black product of container bottom is magnetic ferroferric oxide nano-particles.
(3) synthesis of polymer overmold magnetic ferroferric oxide nano-particles：
0.5mg magnetic ferroferric oxide nano-particles are added to ultrasonic 40min in 1.5mL tetrahydrofurans, treat magnetic four
After Fe 3 O nano-particle is uniformly dispersed, solution is added drop-wise in 6mL ultra-pure waters with needle tubing, ultrasonic 40min obtains scattered equal
Even ferroso-ferric oxide mixed solution；The polymer with Thermo-sensitive that 5mg steps (1) are prepared is dissolved in 1mL tetrahydrochysene furans
In muttering, after being completely dissolved, it is added dropwise in ferroso-ferric oxide mixed solution, ultrasonic 6h, after tetrahydrofuran volatilization completely, i.e.,
The polymer microballoon of coated magnetic ferriferrous oxide nano-particle can be obtained, is the microballoon with Thermo-sensitive magnetic.
Embodiment 5
(1) synthesis of the polymer with Thermo-sensitive：
In 100mL reaction vessel, 1.41g 4- methacryl amidos aniline, 3.62g N- isopropyl propylene are added
Acid amides, 3.80g polyethylene glycol monomethyl ethermethacrylic acid esters and 200mg AIBN, are dissolved in 30mL absolute ethyl alcohol, at 70 DEG C
Under the protection of lower and nitrogen, stirring reaction 24h.Reaction terminates rear reaction solution precipitation purification in hexane, obtains described with temperature sensitive
Property polymer, wherein, x: y: z=1: 2: 1, the polymer relative molecular weight be 13200.
(2) synthesis of magnetic ferroferric oxide nano-particles：
By (NH4)2Fe(SO4)2·6H2O is dissolved in 20ml distilled water, obtains 0.002mol Fe2+Presoma；In room temperature
Under, 10mL oleic acid, 1g sodium hydroxides and 10mL ethanol are mixed, stirred；By Fe2+Presoma is added in the homogeneous solution,
Stirring to precipitation shows brown；Brown mixture is transferred in 50mL autoclaves, and 10h is heated at 180 DEG C；It is last cold
But to room temperature, the black product of container bottom is magnetic ferroferric oxide nano-particles.
(3) synthesis of polymer overmold magnetic ferroferric oxide nano-particles：
0.5mg magnetic ferroferric oxide nano-particles are added to ultrasonic 30min in 1.5mL absolute ethyl alcohols, treat magnetic four
After Fe 3 O nano-particle is uniformly dispersed, solution is added drop-wise in 6mL ultra-pure waters with needle tubing, ultrasonic 30min obtains scattered equal
Even ferroso-ferric oxide mixed solution；The polymer with Thermo-sensitive that 6mg steps (1) are prepared is dissolved in the anhydrous second of 2mL
In alcohol, after being completely dissolved, it is added dropwise in ferroso-ferric oxide mixed solution, ultrasonic 6h, after absolute ethyl alcohol volatilization completely, i.e.,
The polymer microballoon of coated magnetic ferriferrous oxide nano-particle can be obtained, is the microballoon with Thermo-sensitive magnetic.
It is described above, only present pre-ferred embodiments, therefore the scope that the present invention is implemented can not be limited according to this, i.e., according to
The equivalent changes and modifications that the scope of the claims of the present invention and description are made, all should still it belong in the range of the present invention covers.
Claims (9)
- A kind of 1. polymer with Thermo-sensitive, it is characterised in that：The structure of the polymer is shown below：Wherein, x: y: z=1: 1~10: 1~20, the polymer relative molecular weight is 10000~100000.
- A kind of 2. method for preparing the polymer with Thermo-sensitive described in claim 1, it is characterised in that：By 4- metering systems Amide groups aniline, NIPA, polyethylene glycol monomethyl ethermethacrylic acid esters and initiator are dissolved in the first solvent, Under 60~80 DEG C, nitrogen protection, 20~30h of stirring reaction, the polymer with Thermo-sensitive is obtained；Wherein, the 4- Methacryl amido aniline, NIPA, the mol ratio of poly glycol monomethyl ether methacrylic acid are 1: 1~20 : 1~50；The dosage of the initiator is 4- methacryl amidos aniline, NIPA, poly glycol monomethyl ether The 0.1~5% of methacrylic acid gross mass.
- 3. a kind of polymer with Thermo-sensitive using described in claim 1 prepares the side of the microballoon with Thermo-sensitive magnetic Method, it is characterised in that：Including：1) by 4- methacryl amidos aniline, NIPA, polyethylene glycol monomethyl ethermethacrylic acid esters and draw Hair agent is dissolved in the first solvent, under 60~80 DEG C, the nitrogen protection, 20~30h of stirring reaction, is obtained described with Thermo-sensitive Polymer；Wherein, the 4- methacryls amido aniline, NIPA, poly glycol monomethyl ether metering system The mol ratio of acid is 1: 1~20: 1~50；The dosage of the initiator is 4- methacryl amidos aniline, N- isopropyl propylene The 0.1~5% of acid amides, poly glycol monomethyl ether methacrylic acid gross mass；2) magnetic nano-particle is dispersed in the second solvent, then will be dispersed with the second solvent of magnetic nano-particle by It is added dropwise in water, is uniformly dispersed, obtains mixed solution；The polymer with Thermo-sensitive obtained by step 1) is dissolved in second In solvent, it is added dropwise to dropwise in the mixed solution；The matter of wherein described magnetic nano-particle and the polymer with Thermo-sensitive Amount is than being 0.1~1：1~10；Then 3~10h is ultrasonically treated, makes the volatilization of the second solvent complete, obtains being coated with magnetic nano particle The polymer microballoon of son, it is the microballoon with Thermo-sensitive magnetic.
- 4. according to the method in claim 2 or 3, it is characterised in that：The initiator is azodiisobutyronitrile, peroxidating two At least one of benzoyl, ABVN.
- 5. according to the method in claim 2 or 3, it is characterised in that：First solvent be tetrahydrofuran, dichloromethane, At least one of ether, absolute ethyl alcohol；The quality of first solvent is 4- methacryl amidos aniline, N- isopropyls third 5~30 times of acrylamide, polyethylene glycol monomethyl ethermethacrylic acid esters and initiator gross mass.
- 6. according to the method for claim 3, it is characterised in that：Second solvent is tetrahydrofuran, dichloromethane, second At least one of ether, absolute ethyl alcohol；The magnetic nano-particle, the throwing with the polymer of Thermo-sensitive, the second solvent and water Expect that ratio is 0.1~1mg：1~10mg：1~5ml：5~10ml.
- 7. according to the method for claim 3, it is characterised in that：The magnetic nano-particle is magnetic ferroferric oxide nanometer Particle and/or magnetic ferric oxide nano particles.
- 8. according to the method for claim 7, it is characterised in that：The preparation method of the magnetic ferroferric oxide nano-particles Including：By (NH4)2Fe(SO4)2·6H2O is dissolved in distilled water, obtains Fe2+Presoma；By Fe2+Presoma add be mixed with oleic acid, In the homogeneous solution of sodium hydroxide and ethanol, stirring to the aobvious brown of precipitation；Brown mixture heats at 180~200 DEG C to 8~ 12h；Room temperature is finally cooled to, obtains magnetic ferroferric oxide nano-particles.
- A kind of 9. use of the microballoon with Thermo-sensitive magnetic prepared by method according to claim 11 as pharmaceutical carrier On the way.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115672261A (en) * | 2022-10-31 | 2023-02-03 | 江苏海洋大学 | Polymer-modified attapulgite containing sulfhydryl Schiff base side group and preparation method thereof |
| CN115970071A (en) * | 2022-12-02 | 2023-04-18 | 西南交通大学 | Magnetic drug-loaded nanoparticle applied to drug-coated balloon and preparation method thereof |
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2017
- 2017-10-17 CN CN201710965931.9A patent/CN107722190A/en active Pending
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| PUZHEN LI ET AL: "Mussel-Inspired Multidentate Block Copolymer to Stabilize Ultrasmall Superparamagnetic Fe3O4 for Magnetic Resonance Imaging Contrast Enhancement and Excellent Colloidal Stability", 《CHEMISTRY OF MATERIALS》 * |
| SIRAPRAPA MEEROD ET AL: "Hydrophilic magnetic nanoclusters with thermo-responsive properties and their drug controlled release", 《JOURNAL OF MAGNETISM AND MAGNETIC MATERIALS》 * |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115672261A (en) * | 2022-10-31 | 2023-02-03 | 江苏海洋大学 | Polymer-modified attapulgite containing sulfhydryl Schiff base side group and preparation method thereof |
| CN115672261B (en) * | 2022-10-31 | 2024-02-20 | 江苏海洋大学 | Sulfhydryl Schiff base side group-containing polymer modified attapulgite and preparation method thereof |
| CN115970071A (en) * | 2022-12-02 | 2023-04-18 | 西南交通大学 | Magnetic drug-loaded nanoparticle applied to drug-coated balloon and preparation method thereof |
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