CN101385713B - Preparation method of lipoic acid lipid nano-particles - Google Patents
Preparation method of lipoic acid lipid nano-particles Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title abstract description 7
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- 239000007788 liquid Substances 0.000 claims abstract description 12
- 239000000463 material Substances 0.000 claims abstract description 10
- 238000004108 freeze drying Methods 0.000 claims abstract description 7
- 238000002156 mixing Methods 0.000 claims abstract description 5
- 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 17
- 238000000034 method Methods 0.000 claims description 13
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- 238000005303 weighing Methods 0.000 claims description 12
- 238000005352 clarification Methods 0.000 claims description 10
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 7
- 238000013019 agitation Methods 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 229920001213 Polysorbate 20 Polymers 0.000 claims description 4
- 239000012071 phase Substances 0.000 claims description 4
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 claims description 4
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- 230000004927 fusion Effects 0.000 claims description 3
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- OYHQOLUKZRVURQ-HZJYTTRNSA-N linoleic acid group Chemical class C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 3
- 238000012545 processing Methods 0.000 claims description 3
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- 230000000694 effects Effects 0.000 abstract description 4
- 239000012847 fine chemical Substances 0.000 abstract description 3
- 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
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- 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
- 102000004895 Lipoproteins Human genes 0.000 description 2
- 108090001030 Lipoproteins Proteins 0.000 description 2
- 238000013461 design Methods 0.000 description 2
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- 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
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 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
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- 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
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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 method for preparing of lipoic acid lipid nano-particles.
Background technology
Thioctic acid can be removed free radical nearly all in the body as the strongest antioxidant of occurring in nature, through other endogenic antioxidant of redox couple regeneration, like vitamin E, Ascorbate and ubiquinone
10Deng.
Because the above-mentioned oxidation resistance of thioctic acid makes it in clinical practice, obtain extensive studies.Thioctic acid can strengthen the absorption to glucose of skeletal muscle and the erythrocyte of non-insulin-dependent diabetes mellitus animal, 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.Research shows, 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 method for preparing 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 method for preparing 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; Matrix material and thioctic acid are mixed the back 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, and 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, and the emulsifying agent that weighs up is added to the water; In thermostatic water bath, heat, 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 be Vegetable oil lipoprotein and the main chain after the different hard esterification have 12 carbon atoms fatty acid in one or more mixture.
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 such as step 2 are said in the blended emulsifier.
Said 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 lipid that prescription selects for use.
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 method for preparing can avoid thioctic acid directly to contact with air, helps to protect its activity.
3. this method for preparing helps to improve the bioavailability of thioctic acid.
4. the lipoic acid lipid nano-particles good stability of this method for preparing preparation, lucifuge room temperature preservation three months, outward appearance does not have significant change.
5. the lipoic acid lipid nanometer favorable repeatability of this method for preparing 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 accompanying drawing and embodiment the present invention is further described:
Fig. 1 prepares the schematic flow sheet of process for the present invention.
The specific embodiment
Embodiment: a kind of method for preparing 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; Matrix material and thioctic acid are mixed the back 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, and 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, and the emulsifying agent that weighs up is added to the water; In thermostatic water bath, heat, 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 be Vegetable oil lipoprotein and the main chain after the different hard esterification have 12 carbon atoms fatty acid in one or more mixture.
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 such as step 2 are said in the blended emulsifier.
Said 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 (3)
1. the method for preparing 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, matrix material and thioctic acid is mixed the back in thermostatic water bath, heat, temperature T=60～80 degree centigrade; Obtain having dissolved the yellow clarification system of thioctic acid after the fusion, be oil phase;
Step 2: take by weighing emulsifying agent and water respectively; The ratio of emulsifying agent and 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, and the emulsifying agent that weighs up is added to the water, and in thermostatic water bath, heats; Temperature is temperature T=60～80 degree centigrade, is water;
Step 3: the oil phase that step 1 is obtained adds the aqueous phase that step 2 obtains, behind the magnetic agitation mix homogeneously, and high pressure homogenize circulation three times, pressure is 600bar, must clarify system;
Step 4: gained clarification system is reduced to room temperature, promptly gets 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 method for preparing of lipoic acid lipid nano-particles according to claim 1 is characterized in that: described matrix material is selected from mixing of lauric acid or lauric acid and aqueous dispersion linoleic acid derivative.
3. the method for preparing of lipoic acid lipid nano-particles according to claim 1; It is characterized in that: described emulsifying agent is ten polyglycereol monolaurate PGFE10 and the mixing of Tween20, in the blended emulsifier mass ratio of PGFE10 and Tween20 be selected from 1: 1,7: 3 or 9: 1.
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| CN102614091B (en) * | 2011-01-27 | 2014-01-22 | 夏强 | Resveratrol nanostructured lipid carrier and preparation method thereof |
| US10940206B2 (en) * | 2015-05-21 | 2021-03-09 | Ophtalmis Monaco | Ophthalmic composition comprising lipoic acid and a mucomimetic 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 |
| 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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