CN114886855B - Tripterine nano-drug and preparation method thereof - Google Patents
Tripterine nano-drug and preparation method thereof Download PDFInfo
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- CN114886855B CN114886855B CN202210558023.9A CN202210558023A CN114886855B CN 114886855 B CN114886855 B CN 114886855B CN 202210558023 A CN202210558023 A CN 202210558023A CN 114886855 B CN114886855 B CN 114886855B
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/37—Celastraceae (Staff-tree or Bittersweet family), e.g. tripterygium or spindletree
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y40/00—Manufacture or treatment of nanostructures
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
Abstract
The invention relates to a tripterine nano-drug and a preparation method thereof, wherein the nano-drug is assembled by tripterine to form nano-particles, the nano-particles do not contain other carriers except solvents, and the average particle size of the nano-particles is 20-2000 nm. According to the invention, the tripterine is taken as an assembly primitive, so that the tripterine nano-medicament without a carrier is obtained for the first time, the tripterine nano-medicament disclosed by the invention remarkably improves the solubility of the tripterine, and the tripterine nano-medicament has remarkable size dependence on the killing effect of tumors.
Description
Technical Field
The invention relates to the technical field of nano-drugs, in particular to a tripterine nano-drug and a preparation method thereof.
Background
Tripterine (Celstrol) is a pharmaceutical active ingredient derived from natural plant medicine Tripterygium wilfordii (Tripterygium wilfordii hook. F.), has a series of pharmacological activities of inhibiting obesity, resisting tumor, regulating immunity and the like, and has extremely high clinical application potential for one of five natural medicinal compounds most likely to be developed into modern medicines by journal of Cell. However, tripterine lacks polar functional groups, has poor water solubility and short half-life in vivo, and seriously affects the clinical application of tripterine. Therefore, researchers have been devoted to the development of pharmaceutical carriers of tripterine in an effort to solve the problems of tripterine.
The development of the tripterine drug carrier is concentrated in the fields of liposome, polymer micelle, nano microemulsion and the like at present, so that the solubility and in-vivo targeting of the tripterine can be remarkably improved, and a novel method is provided for the clinical application of the tripterine. However, most nanocarriers involve complex synthetic pathways, process amplification is difficult, and metabolic pathways in vivo are not yet defined.
For example, chinese patent CN110652596B discloses a tripterine nanoparticle, a preparation method and application thereof, wherein the nanoparticle uses biodegradable polyamino acid and polyethylene glycol as structural units, and is degradable in vivo, and degradation products can be directly removed from the body through kidneys.
For another example, chinese patent CN108478542B discloses a preparation method and application of a hyaluronic acid coated tripterine nano-drug, wherein the hyaluronic acid coated tripterine nano-drug is composed of tripterine and hyaluronic acid; the mole concentration of the tripterine is 10-50mM/L; the molar concentration of the hyaluronic acid is 10-50mM/L.
Therefore, researchers need new technology and means to design the nano preparation of the tripterine, and provide a nano medicine formed by self-assembly of the tripterine and a preparation method thereof.
Disclosure of Invention
In order to overcome the problems of the tripterine nano-drug, the invention aims to provide the tripterine nano-drug which does not contain other carriers except solvents and a preparation method thereof.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention relates to a tripterine nano-drug, which is characterized in that the nano-drug is assembled by tripterine to form nano-particles, the nano-particles do not contain other carriers except solvents, and the average particle size of the nano-particles is 20-2000 nm. According to the invention, the tripterine is assembled to form the nano particles, so that the solubility of the tripterine is obviously improved, and the inhibition effect of the medicine on tumors is improved.
In a preferred embodiment of the invention, the Zeta potential of the nanoparticle is between-10 mV and-40 mV.
In a preferred embodiment of the invention, the nanoparticles have an average particle diameter of between 30 and 1000 nm; preferably, the particle size of 80% of the nanoparticles is between 10% of the average particle size.
In a preferred embodiment of the invention, the nanoparticles have an average particle diameter of between 30 and 100 nm. Unexpectedly, the inhibitory activity of the tripterine nano-drug provided by the invention on tumor cells is obviously increased along with the reduction of the particle size.
The invention also relates to a preparation method of the tripterine nano-drug, which is characterized by comprising the following steps:
dissolving tripterine in a good solvent, adding the tripterine poor solvent, uniformly mixing, and standing to obtain the tripterine nano-particles with the size range of 20-2000 nm.
The method uses a good solvent-poor solvent method to adjust the assembly mode of drug molecules, which is helpful for researchers to design functional nano-assemblies with different morphologies and different sizes. However, there is no current theory of what drugs can form nano-stable nano-assemblies. Through creative research, the invention surprisingly discovers that the tripterine nano-drug is successfully assembled while avoiding the use of complex drug carriers with unknown toxic and side effects. The good solvent-poor solvent method has the advantages of simplicity and easiness in amplification, and can meet the requirements of industrial production.
The source of the tripterine of the present invention is not limited, and for example, commercial tripterine extract with purity of 90% or more can be used.
In a preferred embodiment of the present invention, the good solvent is selected from one or more of methanol, ethanol, propanol, isopropanol, tert-butanol, acetone, N' N-dimethylformamide, tetrahydrofuran, dimethyl sulfoxide, N-methylpyrrolidone, pyridine; preferably, the good solvent is selected from one or more of dimethyl sulfoxide, ethanol, tetrahydrofuran and pyridine.
In a particularly preferred embodiment of the present invention, the good solvent is dimethylsulfoxide, and the tripterine nano-drug with the average particle size of 30-80nm can be obtained by using dimethylsulfoxide.
In a particularly preferred embodiment in the field of the present invention, the good solvent is ethanol, and the tripterine nano-drug with the average particle size of 80-160 nm can be obtained by adopting ethanol.
In a preferred embodiment of the invention, the poor solvent is selected from the group consisting of water, aqueous dextrose, naCl solution, cell culture medium, and aqueous buffer. Preferably, the poor solvent has a pH of between 6 and 8.
The concentration of the tripterine good solvent solution is 1-200 mg/mL.
The volume ratio of the good solvent to the poor solvent is 1-5: 2 to 10.
The standing time of the tripterine nano-drug is 1 min-1 montath.
In a preferred embodiment of the present invention, the preparation method further comprises a step of removing a part of the solvent by dialysis, ultrafiltration or column chromatography after standing.
In a preferred embodiment of the invention, the step of removing part of the solvent is dialysis; preferably, the dialysis time of the tripterine nano-drug is 4-120 hours. Aggregation of the nano-drug particles can be prevented by employing dialysis.
The molecular weight of the dialysis bag selected by the tripterine nano-drug is not particularly limited, so long as the solvent can be ensured to permeate and the nano-drug particles can not permeate.
The invention also relates to application of the tripterine nano-drug in preparation of drugs for inhibiting tumor cell proliferation.
In a preferred embodiment of the invention, the medicament is an injection or an oral preparation, with or without pharmaceutically acceptable excipients. The pharmaceutically acceptable auxiliary materials are not particularly limited as long as they do not damage the nanoparticle structure of the tripterine nano-drug.
The beneficial effects of the invention at least comprise at least one or more of the following beneficial effects:
(1) According to the invention, the tripterine is taken as an assembly primitive, so that the tripterine nano-medicament without a carrier is obtained for the first time, the tripterine nano-medicament disclosed by the invention remarkably improves the solubility of the tripterine, and the tripterine nano-medicament has remarkable size dependence on the killing effect of tumors.
(2) The tripterine nano-drug has excellent stability, can be kept stable in simulated gastric fluid and simulated intestinal fluid, and can be rapidly released in alkaline environment.
(3) The tripterine nano-drug disclosed by the invention is simple in preparation method and good in reproducibility, and the solubility of tripterine is obviously improved.
(4) The inhibitory activity of the tripterine nano-drug to tumor cells is obviously increased along with the reduction of the particle size.
(5) The tripterine nano-drug can simultaneously meet the requirements of clinical injection and oral drug dosage forms.
Drawings
FIGS. 1-4 are SEM and TEM images of the synthesized nanomaterials of examples 1-4, respectively, wherein FIGS. 1-4A are SEM images and FIGS. 1-4B are TEM images.
FIG. 5 is a graph of the DLS particle size distribution of the synthesized nano-drug of examples 1-4.
FIG. 6 is a Zeta potential distribution plot of the synthesized nanomaterials of examples 1-4.
Fig. 7 is an SEM image of the synthesized nanomedicine of examples 1-4 after incubation in simulated gastric fluid for 2 hours.
Fig. 8 is an SEM image of the synthesized nanomedicine of examples 1-4 after 4h incubation in simulated intestinal fluid.
FIG. 9 is a graph showing drug release profiles of the synthesized nanomedicine of example 5 in alkaline PBS.
FIG. 10 is a particle size distribution of the nano-drug obtained in example 6 using different organic solvents as good solvents.
FIG. 11 is a particle size distribution of nano-drugs obtained in example 7 using different concentrations of tripterine stock solutions.
FIG. 12 is a photograph of 1L of the nano-drug prepared in example 8 using ethanol as a good solvent.
FIG. 13 MTT cell Activity test of the nanoparticles synthesized in examples 1-4 and tripterine powder.
Detailed Description
The present invention is described in detail below with reference to examples, and unless otherwise defined in the specification of the present invention, all technical terms herein are used according to conventional definitions commonly used and understood by one of ordinary skill in the art. The experimental methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials, unless otherwise specified, are commercially available.
Example 1
A preparation method of a tripterine nano-drug comprises the following steps:
taking a certain amount of tripterine, adding dimethyl sulfoxide to prepare 10mg/mL stock solution, taking 100 mu L of the stock solution into an EP tube, adding 900 mu L of water, standing for 5min, and dialyzing for 24h to obtain the tripterine nano-drug.
Fig. 1 shows SEM and TEM images of tripterine nano-drugs, and fig. 1 and 5 show that the tripterine nano-drugs prepared in this example have uniform size, uniform dispersion and 30-80nm size, and fig. 6 shows Zeta potential of the drugs as-18 mV.
(1) Gastrointestinal stability of granules
Preparing simulated gastric fluid and simulated intestinal fluid, taking 100 mu L of tripterine nano-drug, adding 900 mu L of the solution, incubating for 2 hours in the simulated gastric fluid, centrifuging, taking sediment, adding the simulated intestinal fluid, incubating for 4 hours, centrifuging to obtain sediment, and carrying out SEM characterization on the sediment.
The results are shown in figures 7 and 8, the tripterine nano-drug can be kept stable in simulated gastric fluid (figure 7) and intestinal fluid (figure 8), and can meet the requirement of oral administration.
(2) MTT cell Activity assay
MCF-7 cells are inoculated on a 96-cell culture plate, tripterine nano particles and tripterygium wilfordii drug powder with different concentrations are incubated with the cells for 24 hours, then the culture medium is removed, PBS is used for washing twice, fresh culture medium is replaced, MTT is prepared into 5mg/mL stock solution, the stock solution is added into an orifice plate, and absorbance is measured at 570nm after incubation for 4 hours.
As shown in figure 13, the inhibition effect of the tripterine nano-drug on tumors is obviously better than that of tripterine powder.
Example 2
A preparation method of a tripterine nano-drug comprises the following steps:
taking a certain amount of tripterine, adding ethanol to prepare 10mg/mL stock solution, taking 100 mu L of the stock solution into an EP tube, adding 900 mu L of water, standing for 5min, and dialyzing for 24h to obtain the tripterine nano-drug.
Fig. 2 shows SEM and TEM images of tripterine nano-drugs, and fig. 2 and 5 show that the tripterine nano-drugs prepared in this example have uniform size, uniform dispersion, and 80-160 nm size, and fig. 6 shows Zeta potential of the drugs as-21 mV.
(1) Gastrointestinal stability of granules
Preparing simulated gastric fluid and simulated intestinal fluid, taking 100 mu L of tripterine nano-drug, adding 900 mu L of the solution, incubating for 2 hours in the simulated gastric fluid, centrifuging, taking sediment, adding the simulated intestinal fluid, incubating for 4 hours, centrifuging to obtain sediment, and carrying out SEM characterization on the sediment.
The results are shown in figures 7 and 8, the tripterine nano-drug can be kept stable in simulated gastric fluid (figure 7) and intestinal fluid (figure 8), and can meet the requirement of oral administration.
(2) MTT cell Activity assay
MCF-7 cells are inoculated on a 96-cell culture plate, tripterine nano-drug and tripterygium wilfordii drug powder with different concentrations are incubated with the cells for 24 hours, then the culture medium is removed, PBS is used for washing twice, fresh culture medium is replaced, MTT is prepared into 5mg/mL stock solution, the stock solution is added into an orifice plate, and absorbance is measured at 570nm after incubation for 4 hours.
As shown in figure 13, the inhibition effect of the tripterine nano-drug on tumors is obviously better than that of tripterine powder.
Example 3
A preparation method of a tripterine nano-drug comprises the following steps:
taking a certain amount of tripterine, adding tetrahydrofuran to prepare 10mg/mL stock solution, taking 100 mu L of the stock solution into an EP tube, adding 900 mu L of water, standing for 5min, and dialyzing for 24h to obtain the tripterine nano-drug.
Fig. 3 shows SEM and TEM images of tripterine nano-drugs, and fig. 3 and 5 show that the tripterine nano-drugs prepared in this example have uniform size, uniform dispersion and 240-640 nm size, and fig. 6 shows Zeta potential of the drugs as-28 mV.
(1) Gastrointestinal stability of granules
Preparing simulated gastric fluid and simulated intestinal fluid, taking 100 mu L of tripterine nano-drug, adding 900 mu L of the solution, incubating for 2 hours in the simulated gastric fluid, centrifuging, taking sediment, adding the simulated intestinal fluid, incubating for 4 hours, centrifuging to obtain sediment, and carrying out SEM characterization on the sediment.
The results are shown in figures 7 and 8, the tripterine nano-drug can be kept stable in simulated gastric fluid (figure 7) and intestinal fluid (figure 8), and can meet the requirement of oral administration.
(2) MTT cell Activity assay
MCF-7 cells are inoculated on a 96-cell culture plate, tripterine nano-drug and tripterygium wilfordii drug powder with different concentrations are incubated with the cells for 24 hours, then the culture medium is removed, PBS is used for washing twice, fresh culture medium is replaced, MTT is prepared into 5mg/mL stock solution, the stock solution is added into an orifice plate, and absorbance is measured at 570nm after incubation for 4 hours.
As shown in figure 13, the inhibition effect of the tripterine nano-drug on tumors is obviously better than that of tripterine powder.
Example 4
A preparation method of a tripterine nano-drug comprises the following steps:
taking a certain amount of tripterine, adding pyridine, preparing into 10mg/mL stock solution, taking 100 mu L of the stock solution into an EP tube, adding 900 mu L of water, standing for 5min, and dialyzing for 24h to obtain the tripterine nano-drug.
Fig. 4 shows SEM and TEM images of tripterine nano-drugs, and fig. 4 and 5 show that the tripterine nano-drugs prepared in this example have uniform size, uniform dispersion and 550-1200 nm size, and fig. 6 shows Zeta potential of the drugs as-36 mV.
(1) Gastrointestinal stability of granules
Preparing simulated gastric fluid and simulated intestinal fluid, taking 100 mu L of tripterine nano particles, adding 900 mu L of the solution, incubating for 2 hours in the simulated gastric fluid, centrifuging, taking the precipitate, adding the simulated intestinal fluid, incubating for 4 hours, centrifuging to obtain the precipitate, and carrying out SEM characterization on the precipitate.
The results are shown in figures 7 and 8, the tripterine nano-drug can be kept stable in simulated gastric fluid (figure 7) and intestinal fluid (figure 8), and can meet the requirement of oral administration.
(2) MTT cell Activity assay
MCF-7 cells are inoculated on a 96-cell culture plate, tripterine nano-drug and tripterygium wilfordii drug powder with different concentrations are incubated with the cells for 24 hours, then the culture medium is removed, PBS is used for washing twice, fresh culture medium is replaced, MTT is prepared into 5mg/mL stock solution, the stock solution is added into an orifice plate, and absorbance is measured at 570nm after incubation for 4 hours.
As shown in figure 13, the inhibition effect of the tripterine nano-drug on tumors is obviously better than that of tripterine powder.
Example 5
A preparation method of a tripterine nano-drug comprises the following steps:
taking a certain amount of tripterine, respectively adding dimethyl sulfoxide, ethanol, THF and pyridine to prepare 10mg/mL stock solution, taking 100 mu L of the stock solution into an EP tube, adding 900 mu L of water, standing for 5min, and dialyzing for 24h to obtain the tripterine nano-medicament with different particle sizes.
(1) In vitro drug release test of granules
Preparing PBS solution with pH= 9.0,0.1M (containing 0.5% Tween 80), placing 1mL of the tripterine nano particles in a dialysis bag with molecular weight of 3500, placing in 50mL of the PBS solution, taking 1.5mL of peripheral PBS solution at different time points, adding 1.5mL of PBS solution, and measuring the absorption value at 423nm of the taken solution by ultraviolet-visible absorption spectrum to calibrate the concentration of the tripterine so as to obtain the release curve of the tripterine in an alkaline pH environment.
As shown in FIG. 9, the tripterine nano-drug can be quickly released in an alkaline buffer solution.
Example 6
A preparation method of a tripterine nano-drug comprises the following steps:
taking a certain amount of tripterine, respectively adding methanol, ethanol, propanol, isopropanol, tertiary butanol, acetone, N' -N-dimethylformamide, tetrahydrofuran, dimethyl sulfoxide, N-methylpyrrolidone and pyridine to prepare 10mg/mL stock solution, taking 100 mu L of the stock solution into an EP tube, adding 900 mu L of water, standing for 5min, and dialyzing for 24h to obtain the tripterine nano-medicament with different particle sizes.
Fig. 10 shows DLS distribution of tripterine nano-drugs prepared using different organic solvents, and the results show that nano-drugs with different particle size distribution can be obtained by using different organic solvents.
Example 7
A preparation method of a tripterine nano-drug comprises the following steps:
taking a certain amount of tripterine, respectively adding ethanol, respectively preparing into 1mg/mL,5mg/mL,10mg/mL and 20mg/mL stock solution, taking 100 mu L of the stock solution into an EP tube, adding 900 mu L of water, standing for 5min, and dialyzing for 24h to obtain the tripterine nano-particles.
Fig. 11 shows DLS distribution of tripterine nanoparticles at different concentrations, and the results show that nano-drugs with different particle size distribution can be obtained by using tripterine stock solutions with different concentrations.
Example 8
A preparation method of a tripterine nano-drug comprises the following steps:
taking 1g of tripterine, adding into a 1L mobile phase solvent bottle, adding 100mL of ethanol, preparing a 10mg/mL stock solution, adding 900mL of water, standing for 5min, and dialyzing for 24h to obtain the tripterine nano-drug.
The result is shown in figure 12, the preparation method of the tripterine nano-drug can realize the preparation scale of 1L and the industrialization enlargement.
The foregoing describes preferred embodiments of the present invention, but is not intended to limit the invention thereto. Modifications and variations to the embodiments disclosed herein may be made by those skilled in the art without departing from the scope and spirit of the invention.
Claims (7)
1. A tripterine nano-drug is characterized in that the nano-drug is assembled by tripterine to form nano-particles, the nano-particles do not contain other carriers except solvents, the average particle size of the nano-particles is 30 nm-100 nm,
the tripterine nano-drug is prepared by a preparation method comprising the following steps:
dissolving tripterine in a good solvent, adding the tripterine poor solvent, uniformly mixing, and standing to obtain tripterine nano-particles with the size range of 30 nm-100 nm;
the good solvent is dimethyl sulfoxide.
2. The nano-drug of claim 1, wherein Zeta potential of the nano-particles is between-10 mV and-40 mV.
3. The nano-drug according to claim 1 or 2, wherein 80% of the particles of the nano-particles have a particle size of between ±10% of the average particle size.
4. The nano-drug of claim 1, wherein the poor solvent is selected from one or more of water, aqueous dextrose, naCl solution, cell culture medium, and aqueous buffer.
5. The nano-drug according to claim 1, wherein the preparation method further comprises a step of removing a part of the solvent by dialysis, ultrafiltration or column chromatography after the standing.
6. Use of the tripterine nano-drug according to any one of claims 1-5 in the preparation of a medicament for inhibiting tumor cell proliferation.
7. The use according to claim 6, wherein the medicament is an injectable or an oral formulation, with or without pharmaceutically acceptable excipients.
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| EP2525782B1 (en) * | 2010-01-18 | 2019-03-13 | Concept Medical Research Private Limited | Formulations of nano-carriers and methods of preparing the same |
| FR3047665B1 (en) * | 2016-02-17 | 2020-12-11 | Pf Medicament | CELASTROL AND ITS DERIVATIVES IN THE TREATMENT OF PRE-CANCEROUS SKIN TUMORS AND PATHOLOGIES |
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| JP2011111429A (en) * | 2009-11-30 | 2011-06-09 | Hosokawa Micron Corp | Method for producing medicament-containing nano particle |
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| CN109646403A (en) * | 2019-01-11 | 2019-04-19 | 福州大学 | A kind of preparation method of carrier-free immunosuppressive macrocyclic lactone medicament nano granule |
| CN109771660A (en) * | 2019-03-07 | 2019-05-21 | 北京林业大学 | It is a kind of to respond the preparation of pectin-adriamycin/tripterine nanometer particle with pH |
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| 黄甜甜 等.高载药量雷公藤红素纳米混悬剂的制备及体外评价.《中草药》.2020,第51卷(第8期),2125-2133. * |
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