CN101385713A - Preparation method of lipoic acid lipid nano-particles - Google Patents
Preparation method of lipoic acid lipid nano-particles Download PDFInfo
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- CN101385713A CN101385713A CNA2008101073023A CN200810107302A CN101385713A CN 101385713 A CN101385713 A CN 101385713A CN A2008101073023 A CNA2008101073023 A CN A2008101073023A CN 200810107302 A CN200810107302 A CN 200810107302A CN 101385713 A CN101385713 A CN 101385713A
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- 235000019136 lipoic acid Nutrition 0.000 title claims abstract description 62
- 229960002663 thioctic acid Drugs 0.000 title claims abstract description 62
- 239000002105 nanoparticle Substances 0.000 title claims abstract description 32
- -1 lipoic acid lipid Chemical class 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000007788 liquid Substances 0.000 claims abstract description 12
- 239000000463 material Substances 0.000 claims abstract description 11
- 150000002632 lipids Chemical class 0.000 claims abstract description 9
- 238000004108 freeze drying Methods 0.000 claims abstract description 7
- 239000002537 cosmetic Substances 0.000 claims abstract description 5
- 239000012847 fine chemical Substances 0.000 claims abstract description 4
- 238000002156 mixing Methods 0.000 claims abstract description 4
- AGBQKNBQESQNJD-SSDOTTSWSA-N (R)-lipoic acid Chemical compound OC(=O)CCCC[C@@H]1CCSS1 AGBQKNBQESQNJD-SSDOTTSWSA-N 0.000 claims description 30
- AGBQKNBQESQNJD-UHFFFAOYSA-N alpha-Lipoic acid Natural products OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 claims description 30
- 239000011159 matrix material Substances 0.000 claims description 18
- 238000005303 weighing Methods 0.000 claims description 12
- 239000006185 dispersion Substances 0.000 claims description 11
- 238000005352 clarification Methods 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 238000013019 agitation Methods 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 102000004895 Lipoproteins Human genes 0.000 claims description 3
- 108090001030 Lipoproteins Proteins 0.000 claims description 3
- 229920001213 Polysorbate 20 Polymers 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 150000004665 fatty acids Chemical class 0.000 claims description 3
- 230000004927 fusion Effects 0.000 claims description 3
- 239000004519 grease Substances 0.000 claims description 3
- 239000003921 oil Substances 0.000 claims description 3
- 235000019198 oils Nutrition 0.000 claims description 3
- 239000012071 phase Substances 0.000 claims description 3
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 claims description 3
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 claims description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 3
- 239000008158 vegetable oil Substances 0.000 claims description 3
- 238000009333 weeding Methods 0.000 claims description 3
- 230000000694 effects Effects 0.000 abstract description 4
- AGBQKNBQESQNJD-UHFFFAOYSA-M lipoate Chemical compound [O-]C(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-M 0.000 abstract 3
- 230000003247 decreasing effect Effects 0.000 abstract 1
- 238000003760 magnetic stirring Methods 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid ester group Chemical class C(CCCCCCCCCCC)(=O)O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N linoleic acid group Chemical class C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 2
- 239000002502 liposome Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002047 solid lipid nanoparticle Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 102000003746 Insulin Receptor Human genes 0.000 description 1
- 108010001127 Insulin Receptor Proteins 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 235000017471 coenzyme Q10 Nutrition 0.000 description 1
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 description 1
- 238000013267 controlled drug release Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 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 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000002539 nanocarrier Substances 0.000 description 1
- 239000007908 nanoemulsion Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- NPCOQXAVBJJZBQ-UHFFFAOYSA-N reduced coenzyme Q9 Natural products COC1=C(O)C(C)=C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C(O)=C1OC NPCOQXAVBJJZBQ-UHFFFAOYSA-N 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 229940035936 ubiquinone Drugs 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
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- Cosmetics (AREA)
Abstract
The invention discloses a preparation method of lipoic acid lipid nanoparticles, the preparation method comprises the following steps: step one: lipid material and lipoic acid are respectively weighed and heated in a constant temperature water tank, a yellow clarified system of the dissolved lipoic acid is obtained after the melting; step two: an emulsifying agent and water are respectively weighed and heated in the constant temperature water tank; step three: an oil phase under the set temperature T is added in a water phase, the clarified system is obtained after the magnetic stirring and the even mixing; step four: the temperature is decreased to the room temperature, dispersed liquid of the lipoic acid lipid nanoparticles is obtained; step five: the freeze drying is carried out on the dispersed liquid in the step four, and the lipoic acid lipid nanoparticles are obtained; the preparation method takes the lipoic acid lipid nanoparticles as a carrier, thereby being conductive to the protection of the activity of lipoic acid, improving the bioavailability and being applied in cosmetics materials or other fine chemical materials.
Description
Technical field
The present invention relates to a kind of preparation method of lipoic acid lipid nano-particles.
Background technology
Thioctic acid is as the strongest antioxidant of occurring in nature, can remove nearly all free radical in the body, by regenerate other endogenic antioxidant of redox couple, as vitamin E, Ascorbate and ubiquinone
10Deng.
Because the above-mentioned oxidation resistance of thioctic acid makes it obtain extensive studies in clinical practice.Thioctic acid can strengthen the absorption to glucose of the skeletal muscle of non-insulin-dependent diabetes mellitus animal and erythrocyte, and then blood sugar lowering content, and it can also improve the ratio of insulin receptor kinase simultaneously, thereby has strengthened the metabolism of glucose.Metal ions such as the biological intravital ferrum of all right chelating of thioctic acid, chromium, copper, manganese are avoided its catalysis Fenton reaction, thereby can be suppressed the carcinogenic approach that metal ion generates active oxygen.Studies show that antioxidant and derivant thereof can inducing tumor cells when heavy dose in the food differentiation and apoptosis suppress its propagation.
Present nano-carrier comprises nanoparticle, nanoemulsions, liposome, nano suspending liquid, solid lipid nanoparticle, nano structured lipid carrier etc.Wherein solid lipid nanoparticle and liposome nanometer carrier are referred to as lipid nanoparticle.Lipid nanoparticle has following characteristics: 1, realize the probability that controlled drug release and targeting discharge; 2, improved medicine stability; 3, drug loading is higher; 4, oleophylic and hydrophilic drugs all can facilitate the introduction of; 5, carrier does not have bio-toxicity; 6, avoided the use of organic solvent; 7, can carry out large-scale production and sterilization.
Summary of the invention
The present invention seeks to: a kind of preparation method of lipoic acid lipid nano-particles is provided, and lipoic acid lipid nano-particles helps to protect the activity of thioctic acid as carrier, improves its bioavailability, is applicable as cosmetic material or other fine chemistry industry materials.
Technical scheme of the present invention is: a kind of preparation method of lipoic acid lipid nano-particles comprises the following steps:
Step 1: difference weighing matrix material and thioctic acid, both mass ratioes are matrix material: thioctic acid is 2:1, will matrix material and thioctic acid mix the back and in thermostatic water bath, heat, temperature T=60～80 degree centigrade, the yellow clarification system that obtains having dissolved thioctic acid after the fusion;
Step 2: take by weighing emulsifying agent and water respectively, the amount of emulsifying agent is by the ratio decision of emulsifying agent and lipid, its ratio is an emulsifying agent: matrix material is 6:4～8:2, the amount of water is the remaining part of amount of the thioctic acid and the emulsifying agent of total system weeding of grease material, load, the emulsifying agent that weighs up is added to the water, heat in thermostatic water bath, temperature is temperature T=60～80 degree centigrade;
Step 3: the oil phase under the design temperature T is added aqueous phase, behind the magnetic agitation mix homogeneously, high pressure homogenize circulation three times, pressure is 600bar, must clarify system;
Step 4: reduce to room temperature, promptly get the lipoic acid lipid nano-particles dispersion liquid;
Step 5: the dispersion liquid in the step 4 is carried out the lyophilization processing promptly get lipoic acid lipid nano-particles.
Described matrix material is one or more the mixture in the fatty acid of Vegetable oil lipoprotein after the different hard esterification and 12 carbochains.
Described emulsifying agent is to obtain after two kinds of emulsifier, i.e. mixing of ten polyglycereol monolaurate PGFE10 and Tween20, the mixed proportion of two kinds of emulsifying agents is as described in the step 2 in the blended emulsifier.
Described being can be widely used in as carrier loaded material by matrix material in the fine chemical products such as cosmetics.
Advantage of the present invention is:
1. thioctic acid is a kind of fat-soluble active substance, can well be dissolved in the selected lipid of prescription.
2. thioctic acid has very strong non-oxidizability, is easy to reduced its activity by airborne dioxygen oxidation, and the prepared lipid nanoparticle of this preparation method can avoid thioctic acid directly to contact with air, helps to protect its activity.
3. this preparation method helps to improve the bioavailability of thioctic acid.
4. the lipoic acid lipid nano-particles good stability of this preparation method preparation, lucifuge room temperature preservation three months, outward appearance does not have significant change.
5. the lipoic acid lipid nanometer favorable repeatability of this preparation method preparation, the mean diameter that repeats to prepare for three times are respectively 143,156,161nm.
6. preparation process is simple and convenient.
Description of drawings
Below in conjunction with drawings and Examples the present invention is further described:
Fig. 1 is the schematic flow sheet of preparation process of the present invention.
The specific embodiment
Embodiment: a kind of preparation method of lipoic acid lipid nano-particles comprises the following steps:
Step 1: difference weighing matrix material and thioctic acid, both mass ratioes are matrix material: thioctic acid is 2:1, will matrix material and thioctic acid mix the back and in thermostatic water bath, heat, temperature T=60～80 degree centigrade, the yellow clarification system that obtains having dissolved thioctic acid after the fusion;
Step 2: take by weighing emulsifying agent and water respectively, the amount of emulsifying agent is by the ratio decision of emulsifying agent and lipid, its ratio is an emulsifying agent: matrix material is 6:4～8:2, the amount of water is the remaining part of amount of the thioctic acid and the emulsifying agent of total system weeding of grease material, load, the emulsifying agent that weighs up is added to the water, heat in thermostatic water bath, temperature is temperature T=60～80 degree centigrade;
Step 3: the oil phase under the design temperature T is added aqueous phase, behind the magnetic agitation mix homogeneously, high pressure homogenize circulation three times, pressure is 600bar, must clarify system;
Step 4: reduce to room temperature, promptly get the lipoic acid lipid nano-particles dispersion liquid;
Step 5: the dispersion liquid in the step 4 is carried out the lyophilization processing promptly get lipoic acid lipid nano-particles.
Described matrix material is one or more the mixture in the fatty acid of Vegetable oil lipoprotein after the different hard esterification and 12 carbochains.
Described emulsifying agent is to obtain after two kinds of emulsifier, i.e. mixing of ten polyglycereol monolaurate PGFE10 and Tween20, the mixed proportion of two kinds of emulsifying agents is as described in the step 2 in the blended emulsifier.
Described being can be widely used in as carrier loaded material by matrix material in the fine chemical products such as cosmetics.
Embodiment one:
1. take by weighing 1.8 gram lauric acids, 1.8 gram aqueous dispersion linoleic acid derivatives are put into sample cell;
2.60 ℃ heating in water bath adds 2.0 gram thioctic acid after it is melted fully again, obtains yellow clarification system after the stirring;
3. take by weighing 7.2 gram PGFE10,7.2 gram Tween20,70 gram distilled water, put into sample cell.
4. heating in water bath under uniform temp;
5. the yellow clarification system that will dissolve thioctic acid fully joins aqueous phase;
6. magnetic agitation is 2 minutes;
7. high pressure homogenize circulates three times under 600bar pressure;
8. reduce to room temperature and get the lipoic acid lipid nano-particles dispersion liquid;
9. lyophilization is handled and is promptly got lipoic acid lipid nano-particles.
Embodiment two:
1. take by weighing 3.375 gram lauric acids, 1.25 gram thioctic acid, put into sample cell;
2.60 ℃ heating in water bath dissolves it fully, obtains yellow clarification system;
3. take by weighing 2.3625 gram Tween20,5.5125 gram PGFE10,87.5 gram water, add in the sample cell;
4. heating in water bath under uniform temp;
5. the yellow clarification system that will dissolve thioctic acid fully joins aqueous phase;
6. magnetic agitation is 2 minutes;
7. high pressure homogenize circulates three times under 600bar pressure;
8. reduce to room temperature and get the lipoic acid lipid nano-particles dispersion liquid;
9. lyophilization is handled and is promptly got lipoic acid lipid nano-particles.
Embodiment three:
1. take by weighing 1.8 gram lauric acids, 1.8 gram aqueous dispersion linoleic acid derivatives are put into sample cell;
2.60 ℃ heating in water bath adds 2.0 gram thioctic acid after it is melted fully again, obtains yellow clarification system after the stirring;
3. take by weighing 12.98 gram PGFE10,1.44 gram Tween20,80 gram distilled water, put into sample cell.
4. heating in water bath under uniform temp;
5. the yellow clarification system that will dissolve thioctic acid fully joins aqueous phase;
6. magnetic agitation is 2 minutes;
7. high pressure homogenize circulates three times under 600bar pressure;
8. reduce to room temperature and get the lipoic acid lipid nano-particles dispersion liquid;
9. lyophilization is handled and is promptly got lipoic acid lipid nano-particles.
Claims (4)
1. the preparation method of a lipoic acid lipid nano-particles is characterized in that comprising the following steps:
Step 1: difference weighing matrix material and thioctic acid, both mass ratioes are matrix material: thioctic acid is 2:1, will matrix material and thioctic acid mix the back and in thermostatic water bath, heat, temperature T=60～80 degree centigrade, the yellow clarification system that obtains having dissolved thioctic acid after the fusion;
Step 2: take by weighing emulsifying agent and water respectively, the amount of emulsifying agent is by the ratio decision of emulsifying agent and lipid, its ratio is an emulsifying agent: matrix material is 6:4～8:2, the amount of water is the remaining part of amount of the thioctic acid and the emulsifying agent of total system weeding of grease material, load, the emulsifying agent that weighs up is added to the water, heat in thermostatic water bath, temperature is temperature T=60～80 degree centigrade;
Step 3: the oil phase under the design temperature T is added aqueous phase, behind the magnetic agitation mix homogeneously, high pressure homogenize circulation three times, pressure is 600bar, must clarify system;
Step 4: reduce to room temperature, promptly get the lipoic acid lipid nano-particles dispersion liquid;
Step 5: the dispersion liquid in the step 4 is carried out the lyophilization processing promptly get lipoic acid lipid nano-particles.
2. the preparation method of lipoic acid lipid nano-particles according to claim 1 is characterized in that: described matrix material is one or more the mixture in the fatty acid of Vegetable oil lipoprotein after the different hard esterification and 12 carbochains.
3. the preparation method of lipoic acid lipid nano-particles according to claim 1, it is characterized in that: described emulsifying agent is to obtain after two kinds of emulsifier, i.e. mixing of ten polyglycereol monolaurate PGFE10 and Tween20, the mixed proportion of two kinds of emulsifying agents is as described in the step 2 in the blended emulsifier.
4. the preparation method of lipoic acid lipid nano-particles according to claim 1 is characterized in that: described being can be widely used in as carrier loaded material by matrix material in the fine chemical products such as cosmetics.
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| Application Number | Priority Date | Filing Date | Title |
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| CN2008101073023A CN101385713B (en) | 2008-10-24 | 2008-10-24 | Preparation method of lipoic acid lipid nano-particles |
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| CN2008101073023A CN101385713B (en) | 2008-10-24 | 2008-10-24 | Preparation method of lipoic acid lipid nano-particles |
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| CN101385713A true CN101385713A (en) | 2009-03-18 |
| CN101385713B CN101385713B (en) | 2012-01-04 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102614091A (en) * | 2011-01-27 | 2012-08-01 | 夏强 | Resveratrol nanostructured lipid carrier and preparation method thereof |
| CN107820422A (en) * | 2015-05-21 | 2018-03-20 | 摩纳哥奥夫塔尔米斯公司 | Ophthalmic composition comprising lipoic acid and class mucus shaped polymer |
| CN112641727A (en) * | 2020-12-28 | 2021-04-13 | 北京工商大学 | Antioxidant water-in-oil-in-water type micro-nano multiple emulsion and preparation method and application thereof |
| CN114010522A (en) * | 2021-12-22 | 2022-02-08 | 郑州大学 | Lipoic acid mixed micelle and preparation method and application thereof |
-
2008
- 2008-10-24 CN CN2008101073023A patent/CN101385713B/en not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102614091A (en) * | 2011-01-27 | 2012-08-01 | 夏强 | Resveratrol nanostructured lipid carrier and preparation method thereof |
| CN102614091B (en) * | 2011-01-27 | 2014-01-22 | 夏强 | Resveratrol nanostructured lipid carrier and preparation method thereof |
| CN107820422A (en) * | 2015-05-21 | 2018-03-20 | 摩纳哥奥夫塔尔米斯公司 | Ophthalmic composition comprising lipoic acid and class mucus shaped polymer |
| CN112641727A (en) * | 2020-12-28 | 2021-04-13 | 北京工商大学 | Antioxidant water-in-oil-in-water type micro-nano multiple emulsion and preparation method and application thereof |
| CN114010522A (en) * | 2021-12-22 | 2022-02-08 | 郑州大学 | Lipoic acid mixed micelle and preparation method and application thereof |
| CN114010522B (en) * | 2021-12-22 | 2023-10-13 | 郑州大学 | Lipoic acid mixed micelle and preparation method and application thereof |
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| Publication number | Publication date |
|---|---|
| CN101385713B (en) | 2012-01-04 |
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