CN1785258A - Tea tree oil liposome and its preparation method - Google Patents
Tea tree oil liposome and its preparation method Download PDFInfo
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- CN1785258A CN1785258A CN 200510110316 CN200510110316A CN1785258A CN 1785258 A CN1785258 A CN 1785258A CN 200510110316 CN200510110316 CN 200510110316 CN 200510110316 A CN200510110316 A CN 200510110316A CN 1785258 A CN1785258 A CN 1785258A
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- 239000010677 tea tree oil Substances 0.000 title claims abstract description 63
- 229940111630 tea tree oil Drugs 0.000 title claims abstract description 63
- 239000002502 liposome Substances 0.000 title claims description 40
- 238000002360 preparation method Methods 0.000 title claims description 8
- 239000003960 organic solvent Substances 0.000 claims abstract description 22
- 239000003381 stabilizer Substances 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims description 13
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 150000003904 phospholipids Chemical class 0.000 claims description 9
- 239000000725 suspension Substances 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
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- 239000012736 aqueous medium Substances 0.000 claims description 6
- 235000012000 cholesterol Nutrition 0.000 claims description 6
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- 239000000203 mixture Substances 0.000 claims description 6
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- 238000006703 hydration reaction Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
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- 229910019142 PO4 Inorganic materials 0.000 claims description 2
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- 210000000481 breast Anatomy 0.000 claims description 2
- 239000008366 buffered solution Substances 0.000 claims description 2
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
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- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 2
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- 150000002632 lipids Chemical class 0.000 abstract description 2
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- 206010068319 Oropharyngeal pain Diseases 0.000 description 1
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- 241000700584 Simplexvirus Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 208000002474 Tinea Diseases 0.000 description 1
- 241000130764 Tinea Species 0.000 description 1
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- Medicines Containing Plant Substances (AREA)
Abstract
A lipid containing tea tree oil with high sterilizing effect is prepared from tea tree oil, phosphatide and lipophilic stabilizer through dissolving them in organic solvent, vacuum evaporation of organic solvent, adding appropriate organic solvent and water-phase medium, dissolving the residue, ultrasonic emulsifying, vacuum evaporation of organic solvent and hydrating.
Description
Technical field
The invention belongs to pharmaceutical preparation or cosmetic field, be specifically related to a kind of tea tree oil liposome and preparation method thereof.
Background technology
Tea tree oil (tea tree oil) is the volatile essential oil of extracting from several plant leafs of Myrtaceae Melaleuca, can produce by activated mononuclear cell inflammation-inhibiting medium, thereby the permeability that also can change microbial film suppresses many malignant bacterias and mycete.Confirm that through the strictest in the world KST antibacterial tests (Keelsey-sykes test) tea tree oil has very strong killing and inhibitory action to most gram positive bacterias, gram negative bacteria, fungus and herpes simplex virus.Be considered to current the strongest effective and nontoxic, zest is low, active strong natural bactericidal agent, in medical treatment, have to surpass 100 kinds of first aid purposes, as be used for the treatment of piebaldism, acne, tinea, refer to bacterium, gynecological infection, oral cavity are painful, furuncle, acne, clavus, gingivitis, herpes, freeze painful, der Halsschmerz, en, insect bite, knife injury, scratch and can spray applications in family's sterilization and health etc.
Patent application about the medical applications of tea tree oil is arranged much both at home and abroad.U.S. Pat 5716625 discloses anti-skin irritant purposes, U.S. Pat 6413555 discloses the obliterating agent of treatment nail fungi, U.S. Pat 5009890 discloses the purposes of treatment burn, U.S. Pat 5215748 discloses the purposes of treatment big gun rash, Chinese patent 02129299.X discloses a kind of disinfection compositions that contains tea tree oil, Chinese patent CN1461214A discloses a kind of the cured atopic dermatitis of tea tree oil and compositions of asteatosis and inhibition skin pruritus of containing, and Chinese patent 97194879 discloses a kind of compositions that contains the treatment acne of tea tree oil.
Though tea tree oil has many good qualities, also may produce skin when its concentration is higher stimulates, and to epithelial cell and fibroblast toxigenicity, its some composition (as cineol) can cause allergic reaction.Therefore be necessary to seek the zest that suitable method suppresses or reduce tea tree oil.
The whole body that the lipid physical ability reduces medicine absorbs, and avoids the toxic and side effects of medicine, and is biodegradable, non-stimulated to skin, reduces dosage thereby can also form storage storehouse slow releasing pharmaceutical in skin.But do not see the research report of tea tree oil liposome both at home and abroad.
Summary of the invention
The objective of the invention is to disclose a kind of liposome that contains tea tree oil and preparation method thereof, be intended to wrap in the liposome by tea tree oil, realize reducing the zest of tea tree oil, the injection speed of regulation and control tea tree oil, the purpose of reduction dosage, and the novel form of a kind of tea tree oil of expectation exploitation.
The present invention is by tea tree oil, and phospholipid and lipotropy stabilizing agent are prepared into tea tree oil liposome.
Preparation method of the present invention is that tea tree oil, phospholipid and lipotropy stabilizing agent fully are dissolved in certain density organic solvent, and the evaporated under reduced pressure organic solvent makes the raw material film forming.Add an amount of organic solvent and aqueous media dissolving membranoid substance and ultrasonic one-tenth breast again, the evaporated under reduced pressure organic solvent, the gained suspension continues hydration 2～6 hours.
Phospholipid of the present invention is lecithin.
The present invention selects for use the lipotropy stabilizing agent to come the stabilized liposome body structure, the leakage of minimizing medicine, rotten.Described stabilizing agent comprises, cholesterol, stearylamine, phosphatidic acid, tocopherol, vitamin E, preferred cholesterol.
Phospholipid of the present invention and lipotropy stabilizing agent mass ratio are 1: 1～7: 1; The ratio of the quality of tea tree oil and phospholipid and the two gross mass of lipotropy stabilizing agent, promptly medicine fat mass ratio is 0.0015: 1～0.020: 1.
Organic solvent of the present invention is the mixture of chloroform, ether, and its density is near 1gL
-1
The used aqueous media of the present invention is the phosphate buffered solution according to 2000 editions standard preparations of Chinese Pharmacopoeia, pH value 6.5～7.4, preferred 6.8.
Aqueous media and volume of organic solvent ratio is 0.5: 1～3: 1 among the present invention.
The tea tree oil liposome envelop rate that adopts the inventive method to obtain can reach more than 84% favorable reproducibility.The particle diameter of liposome is not more than 500nm.Preserve envelop rate after 3 months in refrigerator, pH value has no significant change, and particle diameter slightly increases, and slow-releasing is good, and bactericidal effect is remarkable.
Description of drawings
Fig. 1 is the tea tree oil liposome electromicroscopic photograph, amplifies 12000 times.
Fig. 2 is the tea tree oil liposome electromicroscopic photograph, amplifies 50000 times.
Fig. 3 is the tea tree oil liposome volumetric particle size distribution.
Fig. 4 is the release in vitro curve of tea tree oil liposome.
The specific embodiment
By following embodiment the specific embodiment of the present invention is described, but protection scope of the present invention is not limited to this.
The preparation of embodiment 1 tea tree oil liposome
Tea tree oil, lecithin, cholesterol fully are dissolved in the mixed organic solvents of chloroform, ether, and (density is about 1gL
-1), the evaporated under reduced pressure organic solvent makes the raw material film forming.Adding mixed organic solvents and pH again in the membranoid substance and be 6.8 PBS dissolves, with the ultrasonic ultrasonic 120s of intensity psychrolusia that stopped 5 seconds in 5 seconds, the evaporated under reduced pressure organic solvent, the gained suspension continues hydration 4 hours, make tea tree oil liposome, its envelop rate is as shown in table 1.
The envelop rate of table 1 tea tree oil liposome
| Sample | Lecithin and cholesterol mass ratio | Medicine fat mass ratio | PBS and organic solvent volume ratio | Envelop rate % |
| 1 2 3 4 5 | 3∶1 5∶1 3∶1 3∶1 3∶1 3∶1 3∶1 3∶1 | 0.0045∶1 0.0030∶1 0.0075∶1 0.0105∶1 0.0105∶1 0.0075∶1 0.0075∶1 0.0075∶1 | 1∶1 1∶1 1∶1 0.5∶1 2∶1 0.5∶1 1∶1 1∶1 | 80.45 77.26 84.51 81.31 80.47 85.11 84.42 83.98 |
The entrapment efficiency determination method is as follows:
Take by weighing the certain mass product, calculate the amount of contained tea tree oil wherein as M in its ratio that accounts for gross product
AlwaysTo wherein adding an amount of petroleum ether extraction, centrifugal, petroleum ether layer Rotary Evaporators reclaim under reduced pressure, residue is 50ml with the anhydrous alcohol solution standardize solution, measure absorbance in the 294nm place, (experiment records: A=0.09063C+0.1001 (r=0.99976, n=5, concentration range 0～4ulml by the tea tree oil standard curve
-1)) calculate the amount of its pairing tea tree oil as M
TripBe calculated as follows the envelop rate of product:
EN%=(M
Always-M
Trip) * 100%/M
Always
Morphologic observation: get 1g tea tree oil liposome product with 20 times of PBS dilutions after, drip that to be placed to film forming on copper mesh even, unnecessary liquid volatilizes, and transmission electron microscope is observed down, product is spherical large unilamellar vesicle, outward appearance rounding, outer ring are the fat layer that comprises tea tree oil, and be thick and homogeneous is continuous, disperse each other between liposome particles, independent, see Fig. 1, Fig. 2.
Particle size distribution measuring: get 2g tea tree oil liposome product and measure volumetric particle size distribution for 50 times with the PBS dilution, as Fig. 3 prepared fresh sample a curve, the particle size range of products therefrom is (284.7 ± 121.5) nm.Product is preserved after 3 months and is handled with method, and particle diameter slightly increases, and is (361.5 ± 212.2) nm, sees 3 months curves of Fig. 3 sample a refrigerator placement.
Get the 1ml tea tree oil, (volume ratio is a dehydrated alcohol: tween 80: tea tree oil: PBS=1: 1: 1: 15 solution) dilution is packed in release medium is soaked the bag filter of 24h for 2.5 times with release medium to contain the liposome of 1ml tea tree oil and blank liposome, (removing bubble in the bag) tightened at two ends, be suspended in the tool plug conical flask that fills the 20ml release medium, 37 ± 1 ℃ of water bath with thermostatic control constant speed stir (120r/min), different time sampling 5ml adds equality of temperature simultaneously with the fresh release medium of volume.The UV value of each time point tea tree oil is proofreaied and correct with the UV value that receives liquid, and the UV value of tea tree oil liposome is proofreaied and correct with the UV value of the blank liposome of corresponding time point, and same sample is got the empirical average value 3 times.By formula: Q
n=20C
n+ 5 ∑ C
N-1Calculate cumulative release amount Q
n(C is the drug level that calculates gained according to standard curve, and n is the sampling number of times).With the cumulative release percentage rate to the time map Fig. 4.
The result shows that tea tree oil solution rate of release is very fast, and the cumulative release rate just reaches 92.6% during 4h, tends to balance behind the 6h.And during 6h in the liposome release rate of tea tree oil only be 54.37%, just tend to balance during 18h, show that tea tree oil liposome has a tangible slow release effect external.
Embodiment 4: the stability of tea tree oil liposome
Get 3 batches of each trisections of tea tree oil liposome product, place refrigerator, room temperature and 37 ℃ of constant incubators to preserve respectively, the envelop rate of observing samples, the variation of outward appearance, color and luster and pH value, as shown in table 2.The result shows that tea tree oil liposome was preserved after 3 months in refrigerator, envelop rate, pH value have no significant change, and mode of appearance is also more stable; More stable in the product that room temperature is preserved month, buff appearred in the rear surface in one month, and pH also begins to reduce, and it is oxidized illustrate that liposome has a part; The liposome of 37 ℃ of preservations is extremely unstable, and complete oxidation is rotten during 20d, and this explanation tea tree oil liposome low temperature storage is stablized.
The stability of table 2 tea tree oil liposome
| Time d | Preservation condition | The investigation project | ||||||
| Sample a | EN% sample b | Sample c | Sample a | PH sample b | Sample c | | ||
| 0 5 5 5 10 10 10 15 15 15 20 20 20 30 30 60 60 90 90 | 37 ℃ of refrigerator room temperatures of 37 ℃ of refrigerator room temperatures of 37 ℃ of refrigerator room temperatures of 37 ℃ of refrigerator room temperatures of refrigerator room temperature refrigerator room temperature refrigerator room temperature | 84.42 83.87 83.65 78.28 83.51 82.89 69.39 84.01 82.77 49.52 83.78 80.86 / 83.56 77.54 82.98 73.33 83.07 69.95 | 83.98 83.54 82.98 79.32 83.91 81.76 72.48 83.03 81.27 53.66 82.65 80.61 / 82.22 78.11 82.78 75.28 82.66 71.04 | 85.11 84.89 84.27 77.35 84.56 82.96 68.63 84.78 83.21 51.07 84.32 81.03 / 84.43 80.57 83.89 76.45 83.71 70.92 | 6.69 6.69 6.69 6.61 6.69 6.69 6.51 6.69 6.69 6.48 6.69 6.68 / 6.69 6.66 6.69 6.58 6.69 6.43 | 6.71 6.71 6.71 6.67 6.71 6.71 6.56 6.71 6.71 6.51 6.71 6.69 / 6.71 6.66 6.71 6.61 6.71 6.52 | 6.67 6.67 6.67 6.63 6.67 6.67 6.54 6.67 6.66 6.45 6.67 6.66 / 6.66 6.64 6.67 6.59 6.66 6.49 | -- - - + - - + - - ++ - - +++ - + - + -- ++ |
Annotate: outward appearance sign symbol is in the table: milky white homogeneous suspension (--); Milky white suspension, the surface has oil to ooze out, little Huang (-); The milky white suspension of lower floor, surface deep yellow (+); The milky white suspension of lower floor, surface deep yellow more than half (++); The buff suspension, rotten (+++).
Embodiment 5 sterilization experiments
The tea tree oil liposome bactericidal assay adopts agar dilution.
Get 10ml tea tree oil liposome (containing tea tree oil 2ml), (volume ratio is a dehydrated alcohol: tween 80: tea tree oil: PBS=1: 1: 1: 15 solution) be diluted to 50ml with release medium, get an amount of successively, with the nutrient agar dilution, make tea tree oil liposome concentration be respectively 0.24%, 0.48%, 0.64%, 0.8% and 1.6%.Experimental strain is escherichia coli and staphylococcus aureus.
The result shows under each concentration of above-mentioned tea tree oil liposome and there is no growth, shows that the tea tree oil liposome bactericidal effect is remarkable.
Claims (10)
1. one kind contains liposome of tea tree oil and preparation method thereof, it is characterized in that: tea tree oil, phospholipid and lipotropy stabilizing agent are dissolved in the organic solvent, after the evaporated under reduced pressure organic solvent film forming, add an amount of organic solvent and aqueous media dissolving membranoid substance and ultrasonic one-tenth breast, the evaporated under reduced pressure organic solvent, the gained suspension continues hydration 2～6 hours.
2. method according to claim 1 is characterized in that described phospholipid is lecithin.
3. method according to claim 1 is characterized in that, described lipotropy stabilizing agent comprises, cholesterol, stearylamine, phosphatidic acid, tocopherol, one or more in the vitamin E.
4. method according to claim 3 is characterized in that, the preferred cholesterol of described lipotropy stabilizing agent.
5. method according to claim 1 is characterized in that, the mass ratio of phospholipid and lipotropy stabilizing agent is 1: 1～7: 1.
6. method according to claim 1 is characterized in that, the ratio of the quality of tea tree oil and phospholipid and the two gross mass of lipotropy stabilizing agent, and promptly medicine fat mass ratio is 0.0015: 1～0.020: 1.
7. method according to claim 1 is characterized in that, described organic solvent is the mixture of chloroform and ether.
8. method according to claim 7 is characterized in that, the density of preferred organic solvent is near 1gL
-1
9. method according to claim 1 is characterized in that, aqueous media is that pH is 6.5～7.4 phosphate buffered solution, preferred pH=6.8.
10. method according to claim 1 is characterized in that, aqueous media and volume of organic solvent ratio are 0.5: 1～3: 1.
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| CN 200510110316 CN1785258A (en) | 2005-11-11 | 2005-11-11 | Tea tree oil liposome and its preparation method |
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|---|---|---|---|
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Cited By (7)
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|---|---|---|---|---|
| CN101829074A (en) * | 2010-05-18 | 2010-09-15 | 南宁辰康生物科技有限公司 | Standardized recombinant tea tree oil and preparing method thereof |
| CN102949460A (en) * | 2012-06-29 | 2013-03-06 | 上海莱博生物科技有限公司 | Application of melaleuca alternifolia oil and preparation thereof |
| CN104606063A (en) * | 2015-03-04 | 2015-05-13 | 王海龙 | Cosmetic active ingredient-containing lipidosome as well as preparation method and application thereof |
| CN105287379A (en) * | 2015-08-10 | 2016-02-03 | 江苏大学 | High-stability antibacterial agent containing tea tree oil nanoliposomes and method for preparing high-stability antibacterial agent containing tea tree oil essential oil nanoliposomes |
| CN105536031A (en) * | 2016-02-03 | 2016-05-04 | 常州市奥普泰科光电有限公司 | A kind of preparation method of tea tree oil liposome anti-inflammatory antibacterial medical dressing |
| CN108210569A (en) * | 2018-03-29 | 2018-06-29 | 晨光生物科技集团股份有限公司 | A kind of tea tree oil microcapsule and its granule |
| CN108653096A (en) * | 2018-07-11 | 2018-10-16 | 中山市智联企业孵化器发展有限公司 | A kind of skin daily nursing liquid and preparation method thereof |
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2005
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Cited By (12)
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| CN101829074A (en) * | 2010-05-18 | 2010-09-15 | 南宁辰康生物科技有限公司 | Standardized recombinant tea tree oil and preparing method thereof |
| CN102949460A (en) * | 2012-06-29 | 2013-03-06 | 上海莱博生物科技有限公司 | Application of melaleuca alternifolia oil and preparation thereof |
| CN104606063A (en) * | 2015-03-04 | 2015-05-13 | 王海龙 | Cosmetic active ingredient-containing lipidosome as well as preparation method and application thereof |
| CN104606063B (en) * | 2015-03-04 | 2021-07-16 | 王海龙 | Liposome containing cosmetic active ingredients and preparation method and application thereof |
| CN105287379A (en) * | 2015-08-10 | 2016-02-03 | 江苏大学 | High-stability antibacterial agent containing tea tree oil nanoliposomes and method for preparing high-stability antibacterial agent containing tea tree oil essential oil nanoliposomes |
| CN105536031A (en) * | 2016-02-03 | 2016-05-04 | 常州市奥普泰科光电有限公司 | A kind of preparation method of tea tree oil liposome anti-inflammatory antibacterial medical dressing |
| CN108721679A (en) * | 2016-02-03 | 2018-11-02 | 丁永新 | A kind of anti-inflammatory antibacterial medical dressing |
| CN105536031B (en) * | 2016-02-03 | 2018-12-11 | 浙江康诚工业产品设计有限公司 | A kind of preparation method of tea tree oil liposome anti-inflammatory antibacterial medical dressing |
| CN108721679B (en) * | 2016-02-03 | 2020-11-20 | 唐山市博世德医疗器械有限公司 | An anti-inflammatory and bacteriostatic medical dressing |
| CN108210569A (en) * | 2018-03-29 | 2018-06-29 | 晨光生物科技集团股份有限公司 | A kind of tea tree oil microcapsule and its granule |
| CN108210569B (en) * | 2018-03-29 | 2021-03-23 | 晨光生物科技集团股份有限公司 | Tea tree oil microcapsule and granules thereof |
| CN108653096A (en) * | 2018-07-11 | 2018-10-16 | 中山市智联企业孵化器发展有限公司 | A kind of skin daily nursing liquid and preparation method thereof |
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