CN105456195A - Antibacterial triclosan liposome and preparation method thereof - Google Patents
Antibacterial triclosan liposome and preparation method thereof Download PDFInfo
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- A61K9/127—Liposomes
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- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
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- A—HUMAN NECESSITIES
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- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
- A61L2300/62—Encapsulated active agents, e.g. emulsified droplets
- A61L2300/626—Liposomes, micelles, vesicles
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Abstract
The invention discloses an antibacterial triclosan liposome and a preparation method thereof. The liposome is mainly prepared from, by weight, 6.2-15.3 arts of triclosan, 78.5-82.5 parts of phospholipid and 4.7-11.5 parts of cholesterol by means of a film dispersion method. The cholesterol and the cholesterol form a film structure of the liposome to have drug molecules of the triclosan entrapped in a lipid bilayer. The preparation method is simple to operate, easy for production and low in cost, and the obtained triclosan liposome is high in drug loading rate, uniform in particle size, controllable in size, good in stability, fine in antibacterial property, good in water solubility and wide in application range, can increase bioavailability of the triclosan obviously, and has good application prospect.
Description
Technical field
The invention belongs to pharmaceutical preparation and anti-biotic material technical field, particularly one carries antimicrobial form medicinal liposome, more particularly, the present invention relates to a kind of antibacterial triclosan liposome and preparation method thereof.
Background technology
Triclosan, formal name used at school is called " triclosan ", and chemical molecular formula is C
12h
7cl
3o
2, be a kind of high-efficient antibacterial agent of broad spectrum type, gram positive bacteria, negative bacterium, yeast and virus all killed and inhibitory action, be widely used among the household chemicals such as soap, toothpaste.But triclosan is hydrophobic antimicrobial agent and easily assembles in water-based and lose activity, thus causes bioavailability to reduce, and limits its range of application.Therefore, how evenly spreading in hydrophilic matrix by hydrophobic triclosan, is the difficult problem that triclosan faces in actual applications.Be at present mostly the product of main active is to increase its dissolubility by adding the organic solvent such as ethylene glycol, glycerol with triclosan, still be difficult to solve the object improving its stability and dauer effect, and the additive such as ethylene glycol also easily produces neurotoxicity, is unfavorable for the extensive use of triclosan water system antimicrobial product.
Liposome (liposome) is that British scholar Bangham and Standish found in nineteen sixty-five, and is applied to pharmaceutical carrier field very soon.Liposome is made up of phospholipid and additives, and phospholipid is amphiprotic substance, and its structure has hydrophilic and lipophilic group, and conventional has egg yolk lecithin, soybean phospholipid etc.The hydrophilic stem forming the lipoid of bilayer forms the surfaces externally and internally of film, and lipophilic end section is in the centre of film, and wall thickness is about 5 ~ 7nm, and the diameter of capsule is generally between 25 ~ 50nm.This structure of liposome can carry various hydrophilic or lyophobic dust, particularly may be used for loading hydrophobic drug to improve the dispersibility of medicine in aqueous systems and activity.Meanwhile, liposome is similar to biofilm structure, can have stronger affinity with cell membrane, can the transparency of enhanced activity thing, improves curative effect, even can control it in in-house distribution by the size changing liposome.Therefore, water-insoluble antibacterials triclosan is encapsulated as liposome, greatly can improves the valid density in its aqueous solution, extend action time, be expected to make the application of triclosan waterborne antibacterial product obtain wide spread.
Summary of the invention
The technical problem to be solved in the present invention is the slightly solubility existed for current antimicrobial triclosan self, be unfavorable for widely using of its antimicrobial product, there is provided a kind of product quality high, uniform particle sizes, product stability is good, the antibacterial triclosan liposome materials that drug loading is high, provides a kind of method simple simultaneously, be easy to generate, the method for this antibacterial triclosan material of lower-cost preparation.
For solving the problems of the technologies described above, the technical solution used in the present invention is:
Antibacterial triclosan liposome of the present invention, its component comprises triclosan, phospholipid, cholesterol, and the weight of each component is triclosan 6.2 ~ 15.3 parts, 78.5 ~ 82.5 parts, phospholipid, 4.7 ~ 11.5 parts, cholesterol.As preferably, the weight of described each component is triclosan 9.2 parts, 82.5 parts, phospholipid, 8.3 parts, cholesterol.
In described triclosan liposome, triclosan is antibacterials active component, and phospholipid and cholesterol are the basis forming liposome membrane structure.
Triclosan liposome of the present invention belongs to small unilamellar vesicle, it is the vesicle of the bilayer lipid membrane being formed single chamber with phospholipid and cholesterol for film material, cholesterol is distributed in the inside of lipid film bilayer, and triclosan is embedded in the middle of the bilayer of lipid film equally.
The antibacterials active component triclosan of this liposome is embedded in liposome, effectively improves the valid density of triclosan in water, and in conjunction with the stronger affinity advantage of liposome and cell membrane, improves the bioavailable efficiency of triclosan.When liposome contacts with antibacterial in aqueous, liposome membrane can be combined with pre biooxidation, and sustained release Antibacterial Constituents triclosan, plays the effect of killing antibacterial, and therefore this triclosan liposome has good anti-microbial property.
As limitation of the invention, described phospholipid is natural yolk phospholipid, phospholipid of natural soybean or hydrogenated soya phosphatide.Preferably, consider the stability of liposome, described phospholipid is hydrogenated soya phosphatide.Hydrogenated soya phosphatide is obtained through chemical hydrogenation by natural soybean phospholipid, therefore has higher phase transition temperature and stability, and therefore obtained liposome is also more stable.
The preparation method of antibacterial triclosan liposome of the present invention, comprises the steps:
(1) take triclosan, phospholipid, cholesterol respectively in proportion, be fully dissolved in ethanol and be mixed with mixed solution;
In the mixed solution described in step (1), the concentration of phospholipid is 1.25 ~ 5mg/mL.When the concentration of phospholipid is less than 1.25mg/mL, the low medicine delivered payload capability of liposome that causes of content of phospholipid is low; When phospholipid concentration is greater than 5mg/mL, gained liposome is bad, poor stability.Preferably, in mixed solution, the concentration of phospholipid is 2.5mg/mL.
In the mixed solution described in step (1), the weight of phospholipid, cholesterol and triclosan is 1:0.06 ~ 0.14:0.1 ~ 0.4.When cholesterol ratio is too low, the mobility of double-layer of lipoid can be caused to reduce, affect the stability of lipid bilayer; When cholesterol ratio is too high, cholesterol competitively in conjunction with the lipophilic domains of phospholipid, can cause the carrying drug ratio of liposome to reduce, and the fatty acid chain of phospholipid can be made to ossify, and affects the stability of liposome membrane equally.When the ratio of triclosan is too low, the carrying drug ratio of liposome is not high, and medicine effective concentration is low, and Practical significance is little; When the excessive concentration of triclosan, the hydrophilic of gained liposome declines, the less stable of its aqueous solution.Preferably, in mixed solution, the quality proportioning of phospholipid, cholesterol and triclosan is 1:0.1:0.2.
(2) the mixed ethanol solution of the phospholipid described in step (1), cholesterol, triclosan is placed on Rotary Evaporators, slowly removes ethanol, at the bottom of bottle, form milky thin film;
The rotary speed of described Rotary Evaporators is 60 ~ 100 turns/min, and rotational time is 30min ~ 1h, and bath temperature is 40 ~ 60 DEG C.When the rotary speed of Rotary Evaporators is lower than 60 turns/min, the lipid film of formation is thicker; When rotary speed is higher than 100 turns/min, the lipid film of formation is uneven, and all impact generates the uniformity of liposome.When bath temperature is lower than 40 DEG C, do not reach the phase transition temperature of hydrogenated soya phosphatide, cannot film forming; When water solution temperature is higher than 60 DEG C, the easy bumping of alcoholic solution affects film forming.Preferably, the rotary speed of described Rotary Evaporators is 80 turns/min, and rotational time is 45min, bath temperature 55 DEG C.
(3) pure water or buffer solution of sodium phosphate are joined in flask, shaking table vibrates, obtain liposome turbid liquor;
The concentration of buffer solution of sodium phosphate is 0.01mol/L, pH is 7.4, as hydration medium.
Duration of oscillation in described step (3) is 25 ~ 40min, can make the abundant swelling hydration of thin film.Lipid occurs swelling and by eluting from level to level, great majority define multilamellar liposome.Preferably, described duration of oscillation is 30min.
(4) in ice-water bath, Probe Ultrasonic Searching is carried out to the liposome turbid liquor obtained in step (3), form transparency liquid; Filter, collect filtrate, obtain the aqueous solution of antibacterial triclosan liposome.
The method of described Probe Ultrasonic Searching is: arranging power is 80 ~ 120W; Adopt circulating ultrasonic, at every turn ultrasonic 0.6 ~ 1s, interval 0.6 ~ 0.8s, ultrasonic time 10 ~ 30min, carry out in ice-water bath.The present invention adopts probe type ultrasonic method, multilamellar liposome larger for particle diameter is separated into further the less unilamellar liposome of particle diameter, make the liposomal particle size that obtains less and more homogeneous, prevent heat accumulation in ultrasonic procedure from causing phospholipid oxidation by the cooling of ice-water bath.Preferably, the method for described Probe Ultrasonic Searching is: arranging power is 100W; Adopt circulating ultrasonic, each ultrasonic 0.8s, interval 0.8s, ultrasonic time 20min.
The disposable sterilized syringe filter filtration sterilization in 0.22 μm of aperture is adopted in described step (4).Both can control particle diameter, improve homogeneity, by filtering the antibacterial of removing in solution, degerming effect can be reached, be convenient to practical application again.
Calculate can obtain by ultraviolet-visible absorption spectroscopy, in the triclosan liposome that the present invention obtains, the efficient loading rate 6.2 ~ 15.3% of triclosan, the valid density of triclosan can reach 0.12 ~ 0.3mg/mL in aqueous, effectively improve the water solublity of triclosan, and then its range of application in water system antimicrobial product can be made more extensive.
Antibacterial triclosan liposome the present invention obtained, for the preparation of deep layer antimicrobial form dermal agent, has the dry goods medical apparatus and instruments of antibacterial action or other products and the application in waterborne antibacterial material.
Wherein preferably, above-mentioned triclosan liposome may be used for for the application in multiple antimicrobial form medicament, fabric and the waterborne antibacterial materials such as escherichia coli, staphylococcus aureus, Candida albicans.
After adopting technique scheme, the beneficial effect that the present invention obtains is: liposome of the present invention adopts triclosan, phospholipid, cholesterol to be raw material, and to regulate the weight of each raw material, Antibacterial Constituents triclosan is embedded in liposome, drug product quality is high, uniform particle sizes, good stability, drug loading is high, effectively improve the valid density of medicine in water, there is cell membrane affinity, entering in cell by merging, release active medicine, improves the antibacterial effect of medicine.Meanwhile, the preparation method of triclosan liposome of the present invention improves product quality, and drug loading is large, and method is simple, and be easy to generate, cost is lower.
Accompanying drawing explanation
Fig. 1 is the structural representation of triclosan liposome, and phospholipid and cholesterol form liposome bimolecular film structure, and triclosan molecule is embedded in the middle of the bilayer of phospholipid.1 is Whole structure model figure, the hydrophobic chain of 2 expression phospholipid, and the water-wet side of 3 expression phospholipid, 4 represent cholesterol, and 5 represent triclosans.
Fig. 2 is the grain size distribution of the triclosan liposome prepared by embodiment 3, and liposome has more homogeneous size, and mean diameter is 52nm, is small unilamellar vesicle.
Fig. 3 is the ultraviolet-visible absorption spectroscopy figure of the triclosan liposome solutions prepared by embodiment 3, and the charging ratio calculating triclosan by its standard curve by the characteristic absorption peak of triclosan in 280nm position is 9.2%.
Fig. 4 is the antibacterial effect of the triclosan liposome prepared by embodiment 3: 2-a is matched group; 2-b is triclosan liposome group, and in bacterium liquid, triclosan valid density is 10 μ g/mL.Bacteria tested is escherichia coli.
Detailed description of the invention
For enabling above-mentioned purpose of the present invention, feature and advantage become apparent more, are described in detail below in conjunction with the specific embodiment of the present invention.Set forth a lot of detail in the following description so that fully understand the present invention.But the present invention can be much different from alternate manner described here to implement, those skilled in the art can when without prejudice to doing similar improvement when intension of the present invention, therefore the present invention is by the restriction of following public concrete enforcement.
Be specific embodiment part below.
Embodiment 1
Take natural yolk phospholipid, cholesterol, triclosan respectively in proportion, add in a certain amount of ethanol, fully dissolve and obtain mixed ethanol solution, wherein phospholipid concentration is 3.5mg/mL, and the quality proportioning of phospholipid, cholesterol and triclosan is 1:0.1:0.13.
Join in round-bottomed flask by the mixed ethanol solution of above-mentioned phospholipid, cholesterol, triclosan, be placed on Rotary Evaporators that speed setting is 60 turns/min, rotary evaporation 30min in 40 DEG C of water-baths, removing ethanol, forms milky thin film at the bottom of bottle;
Be 0.01M, pH using concentration be that 7.4 phosphate buffers join in flask as hydration medium, shaking table vibrates 25min, obtains liposome turbid liquor;
Be that 80W carry out Probe Ultrasonic Searching with ultrasonic power by the liposome turbid liquor obtained in ice-water bath, circulating ultrasonic set-up mode is: each ultrasonic 0.6s, interval 0.6s; Ultrasonic time is 10min.
By the ultrasonic clear solution obtained, filtered by the disposable syringe filter in 0.22 μm of aperture, collect filtrate, obtain triclosan liposome solutions.
The triclosan liposome obtained in this embodiment, its each ingredients weight parts proportioning is triclosan 9.3 parts, 82.5 parts, phospholipid, 8.2 parts, cholesterol, and the charging ratio of the triclosan finally obtained is 9.3%.
Embodiment 2
Take phospholipid of natural soybean, cholesterol, triclosan respectively in proportion, add in a certain amount of ethanol, fully dissolve and obtain mixed ethanol solution, wherein phospholipid concentration is 3mg/mL, and the quality proportioning of phospholipid, cholesterol and triclosan is 1:0.12:0.2.
Join in round-bottomed flask by the mixed ethanol solution of above-mentioned phospholipid, cholesterol, triclosan, be placed on Rotary Evaporators that speed setting is 100 turns/min, rotary evaporation 1h in 60 DEG C of water-baths, removing ethanol, forms milky thin film at the bottom of bottle;
Join in flask using pure water as hydration medium, shaking table vibrates 40min, obtains liposome turbid liquor;
Be that 120W carry out Probe Ultrasonic Searching with ultrasonic power by the liposome turbid liquor obtained in ice-water bath, circulating ultrasonic set-up mode is: each ultrasonic 1s, interval 0.8s; Ultrasonic time is 30min.
By the ultrasonic clear solution obtained, filtered by the disposable syringe filter in 0.22 μm of aperture, collect filtrate, obtain triclosan liposome solutions.
The triclosan liposome obtained in this embodiment, its each ingredients weight parts proportioning is triclosan 12 parts, 78.5 parts, phospholipid, 9.5 parts, cholesterol, and the charging ratio of the triclosan finally obtained is 12%.
Embodiment 3
Take hydrogenated soya phosphatide, cholesterol, triclosan respectively in proportion, add in a certain amount of ethanol, fully dissolve and obtain mixed ethanol solution, wherein phospholipid concentration is 2.5mg/mL, and the quality proportioning of phospholipid, cholesterol and triclosan is 1:0.1:0.2.
Join in round-bottomed flask by the mixed ethanol solution of above-mentioned phospholipid, cholesterol, triclosan, be placed on Rotary Evaporators that speed setting is 80 turns/min, rotary evaporation 45min in 55 DEG C of water-baths, removing ethanol, forms milky thin film at the bottom of bottle;
Be 0.01M, pH using concentration be that 7.4 phosphate buffers join in flask as hydration medium, shaking table vibrates 30min, obtains liposome turbid liquor;
Be that 100W carry out Probe Ultrasonic Searching with ultrasonic power by the liposome turbid liquor obtained in ice-water bath, circulating ultrasonic set-up mode is: each ultrasonic 0.8s, interval 0.8s; Ultrasonic time is 20min.
By the ultrasonic clear solution obtained, filtered by the disposable syringe filter in 0.22 μm of aperture, collect filtrate, obtain triclosan liposome solutions.
The triclosan liposome obtained in this embodiment, its each ingredients weight parts proportioning is triclosan 9.2 parts, 82.5 parts, phospholipid, 8.3 parts, cholesterol, and the charging ratio of the triclosan finally obtained is 9.2%.
Embodiment 4
Take hydrogenated soya phosphatide, cholesterol, triclosan respectively in proportion, add in a certain amount of ethanol, fully dissolve and obtain mixed ethanol solution, wherein phospholipid concentration is 1.25mg/mL, and the quality proportioning of phospholipid, cholesterol and triclosan is 1:0.06:0.4.
Join in round-bottomed flask by the mixed ethanol solution of above-mentioned phospholipid, cholesterol, triclosan, be placed on Rotary Evaporators that speed setting is 90 turns/min, rotary evaporation 35min in 60 DEG C of water-baths, removing ethanol, forms milky thin film at the bottom of bottle;
Be 0.01M, pH using concentration be that 7.4 phosphate buffers join in flask as hydration medium, shaking table vibrates 30min, obtains liposome turbid liquor;
Be that 90W carry out Probe Ultrasonic Searching with ultrasonic power by the liposome turbid liquor obtained in ice-water bath, circulating ultrasonic set-up mode is: each ultrasonic 0.7s, interval 0.7s; Ultrasonic time is 25min.
By the ultrasonic clear solution obtained, filtered by the disposable syringe filter in 0.22 μm of aperture, collect filtrate, obtain triclosan liposome solutions.
The triclosan liposome obtained in this embodiment, its each ingredients weight parts proportioning is triclosan 15.3 parts, 80 parts, phospholipid, 4.7 parts, cholesterol, and the charging ratio of the triclosan finally obtained is 15.3%.
Embodiment 5
Take hydrogenated soya phosphatide, cholesterol, triclosan respectively in proportion, add in a certain amount of ethanol, fully dissolve and obtain mixed ethanol solution, wherein phospholipid concentration is 5mg/mL, and the quality proportioning of phospholipid, cholesterol and triclosan is 1:0.14:0.1.
Join in round-bottomed flask by the mixed ethanol solution of above-mentioned phospholipid, cholesterol, triclosan, be placed on Rotary Evaporators that speed setting is 80 turns/min, rotary evaporation 35min in 60 DEG C of water-baths, removing ethanol, forms milky thin film at the bottom of bottle;
Be 0.01M, pH using concentration be that 7.4 phosphate buffers join in flask as hydration medium, shaking table vibrates 25min, obtains liposome turbid liquor;
Be that 80W carry out Probe Ultrasonic Searching with ultrasonic power by the liposome turbid liquor obtained in ice-water bath, circulating ultrasonic set-up mode is: each ultrasonic 0.6s, interval 0.6s; Ultrasonic time is 10min.
By the ultrasonic clear solution obtained, filtered by the disposable syringe filter in 0.22 μm of aperture, collect filtrate, obtain triclosan liposome solutions.
The triclosan liposome obtained in this embodiment, its each ingredients weight parts proportioning is triclosan 6.2 parts, 82.3 parts, phospholipid, 11.5 parts, cholesterol, and the charging ratio of the triclosan finally obtained is 6.2%.
The above embodiment only have expressed several embodiment of the present invention, and it describes comparatively concrete and detailed, but therefore can not be interpreted as the restriction to the scope of the claims of the present invention.It should be pointed out that for the person of ordinary skill of the art, without departing from the inventive concept of the premise, can also make some distortion and improvement, these all belong to protection scope of the present invention.Therefore, the protection domain of patent of the present invention should be as the criterion with claims.
Claims (11)
1. an antibacterial triclosan liposome, its composition comprises triclosan, phospholipid, cholesterol, it is characterized in that: the weight of each component is triclosan 6.2 ~ 15.3 parts, 78.5 ~ 82.5 parts, phospholipid, 4.7 ~ 11.5 parts, cholesterol.
2. antibacterial triclosan liposome according to claim 1, is characterized in that: the weight of described each component is triclosan 9.2 parts, 82.5 parts, phospholipid, 8.3 parts, cholesterol.
3. antibacterial triclosan liposome according to claim 1, is characterized in that: described phospholipid is natural yolk phospholipid, phospholipid of natural soybean or hydrogenated soya phosphatide, wherein preferred hydrogenated soya phosphatide.
4. antibacterial triclosan liposome according to claim 1, is characterized in that: in described each component, triclosan is Antibacterial Constituents, and phospholipid and cholesterol are the basis forming liposome membrane structure.
5. antibacterial triclosan liposome according to claim 1, is characterized in that: described antibacterial liposome materials is transparent milk white liquid, the charging ratio measuring wherein triclosan through UV-Visible absorption spectrum is 6.2 ~ 15.3%.
6. the preparation method of antibacterial triclosan liposome according to claim 1, is characterized in that, adopt film dispersion method preparation, concrete steps are as follows:
(1) phospholipid, cholesterol and triclosan is taken respectively in proportion; Phospholipid, cholesterol, triclosan are added in ethanol successively, fully dissolves, be mixed with the mixed ethanol solution of phospholipid, cholesterol, triclosan;
(2) the mixed ethanol solution of phospholipid step (1) obtained, cholesterol, triclosan joins in round-bottomed flask, is placed on Rotary Evaporators, and removing ethanol, forms milky thin film at the bottom of bottle;
(3) hydration medium such as pure water or phosphate buffer is joined in the flask of step (3), shaking table vibrates, obtain liposome turbid liquor;
(4) liposome turbid liquor that step (4) obtains is carried out Probe Ultrasonic Searching in ice-water bath, form transparency liquid; Filter, collect filtrate, obtain described antibacterial triclosan liposome.
7. the preparation method of antibacterial triclosan liposome according to claim 6, is characterized in that: in the mixed ethanol solution of phospholipid, cholesterol, triclosan described in step (1), the concentration of phospholipid is 1.25 ~ 5mg/mL; The weight of phospholipid, cholesterol and triclosan is 1:0.06 ~ 0.14:0.1 ~ 0.4.
8. the preparation method of antibacterial triclosan liposome according to claim 6, it is characterized in that: described in step (2), the rotary speed of Rotary Evaporators is 60 ~ 100 turns/min, bath temperature is set to 40 ~ 60 DEG C, and the rotary evaporation time is 30min ~ 1h.
9. the preparation method of antibacterial triclosan liposome according to claim 6, is characterized in that: the concentration of phosphate buffer described in step (3) is 0.01mol/L, pH is 7.4; Duration of oscillation is 25 ~ 40min.
10. the preparation method of antibacterial triclosan liposome according to claim 6, is characterized in that: described in step (4), the method for Probe Ultrasonic Searching is: arranging power is 80 ~ 120W; Adopt circulating ultrasonic, at every turn ultrasonic 0.6 ~ 1s, interval 0.6 ~ 0.8s; Ultrasonic time is 10 ~ 30min.
The preparation method of 11. antibacterial triclosan liposomees according to claim 6, is characterized in that: filtering described in step (4) is the disposable sterilized syringe filter in employing 0.22 μm of aperture.
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| CN109090440A (en) * | 2018-08-10 | 2018-12-28 | 武汉轻工大学 | A kind of monascorubin unilamellar liposome and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013043830A1 (en) * | 2011-09-20 | 2013-03-28 | Molecular Express, Inc. | Nanoparticle formulations of poorly soluble compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2013043830A1 (en) * | 2011-09-20 | 2013-03-28 | Molecular Express, Inc. | Nanoparticle formulations of poorly soluble compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109090440A (en) * | 2018-08-10 | 2018-12-28 | 武汉轻工大学 | A kind of monascorubin unilamellar liposome and preparation method thereof |
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