CN102641242B - Method for preparing composite phospholipid sterol lipid - Google Patents
Method for preparing composite phospholipid sterol lipid Download PDFInfo
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- CN102641242B CN102641242B CN 201210073732 CN201210073732A CN102641242B CN 102641242 B CN102641242 B CN 102641242B CN 201210073732 CN201210073732 CN 201210073732 CN 201210073732 A CN201210073732 A CN 201210073732A CN 102641242 B CN102641242 B CN 102641242B
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- lipid
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- phospholipid
- liposome
- sterin
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- 239000002131 composite material Substances 0.000 title claims abstract description 22
- -1 phospholipid sterol lipid Chemical class 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 title abstract description 11
- 229930182558 Sterol Natural products 0.000 title abstract 2
- 235000003702 sterols Nutrition 0.000 title abstract 2
- 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 abstract description 46
- 150000002632 lipids Chemical class 0.000 claims abstract description 43
- 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 claims abstract description 28
- 238000002360 preparation method Methods 0.000 claims abstract description 28
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 claims abstract description 24
- 239000008347 soybean phospholipid Substances 0.000 claims abstract description 24
- 235000012000 cholesterol Nutrition 0.000 claims abstract description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000005303 weighing Methods 0.000 claims abstract description 20
- 229930003427 Vitamin E Natural products 0.000 claims abstract description 14
- 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 abstract description 14
- 235000019165 vitamin E Nutrition 0.000 claims abstract description 14
- 229940046009 vitamin E Drugs 0.000 claims abstract description 14
- 239000011709 vitamin E Substances 0.000 claims abstract description 14
- 238000001914 filtration Methods 0.000 claims abstract description 3
- 239000002502 liposome Substances 0.000 claims description 30
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims description 26
- 150000003904 phospholipids Chemical class 0.000 claims description 25
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 20
- 229930193551 sterin Natural products 0.000 claims description 20
- 229960000905 indomethacin Drugs 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 230000006837 decompression Effects 0.000 claims description 10
- 239000003889 eye drop Substances 0.000 claims description 10
- 229910021538 borax Inorganic materials 0.000 claims description 9
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 9
- 239000004327 boric acid Substances 0.000 claims description 9
- 229940012356 eye drops Drugs 0.000 claims description 9
- 239000004328 sodium tetraborate Substances 0.000 claims description 9
- 235000010339 sodium tetraborate Nutrition 0.000 claims description 9
- 239000007853 buffer solution Substances 0.000 claims description 7
- 239000012528 membrane Substances 0.000 claims description 6
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000007670 refining Methods 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- 239000000872 buffer Substances 0.000 claims description 3
- 239000012467 final product Substances 0.000 claims description 2
- 238000012856 packing Methods 0.000 claims description 2
- 230000001954 sterilising effect Effects 0.000 claims description 2
- 238000004659 sterilization and disinfection Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 3
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical group CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- CFWRDBDJAOHXSH-SECBINFHSA-N 2-azaniumylethyl [(2r)-2,3-diacetyloxypropyl] phosphate Chemical compound CC(=O)OC[C@@H](OC(C)=O)COP(O)(=O)OCCN CFWRDBDJAOHXSH-SECBINFHSA-N 0.000 description 1
- 102000011690 Adiponectin Human genes 0.000 description 1
- 108010076365 Adiponectin Proteins 0.000 description 1
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 239000000232 Lipid Bilayer Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 244000144992 flock Species 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000001095 phosphatidyl group Chemical group 0.000 description 1
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 1
- 150000003905 phosphatidylinositols Chemical class 0.000 description 1
- 229940067626 phosphatidylinositols Drugs 0.000 description 1
- 210000002706 plastid Anatomy 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 150000003408 sphingolipids Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
Abstract
The invention relates to a method for preparing composite phospholipid sterol lipid. The preparation method comprises the following steps of: 1, weighing soybean phospholipid, cholesterol and vitamin E, dissolving by using absolute ethyl alcohol, uniformly mixing and filtering; and 2, putting the lipid solution on a rotary evaporator, decompressing, removing the absolute ethyl alcohol, and forming a film to obtain lipid lumps.
Description
Technical field:
The present invention relates to a kind of preparation method of liposome, particularly a kind of preparation method of composite phospholipid sterin lipid.
Background technology:
Liposome (liposome) is a kind of synthetic membrane.The phospholipid molecule hydrophilic head inserts in the water in water, and the liposome hydrophobic tail is stretched to air, forms the globular adiponectin plastid of double-deck fat molecule after stirring, and diameter 25～1000nm does not wait.Liposome can be used for transgenic, or the medicine of preparation, the characteristics of utilizing liposome to merge with cell membrane, medicine is sent into definition cell interior biology: when amphiphatic molecule such as phospholipid and sphingolipid are scattered in water, the hydrophobic tail of molecule is tended to flock together, and avoids water, and hydrophilic head is exposed to water, formation have the bilayer structure vesicle, be called liposome.Pharmaceutics definition liposome (liposome): mean drug encapsulation in the lipoids bilayer and the micro-bubbles utricule that forms.
Liposome (Liposomes) is to be formed for film material enclose by phospholipid cholesterol etc.Can form the multilamellar microcapsule when phospholipid is dispersed in water, and every layer be lipid bilayer, separated by water between each layer.
Chinese patent 02153385.7 has been described a kind of Indomethacin liposome eye drops, and it is by indomethacin, and the preparation liposome is with lipid and cushion solution composition, and liposome wherein is comprised of soybean phospholipid, cholesterol and vitamin E, and its preparation method is as follows:
Take by weighing soybean phospholipid, cholesterol and the vitamin E of recipe quantity, make its dissolving, mix homogeneously with dehydrated alcohol.On membrane evaporator, dehydrated alcohol is removed in decompression, obtains the lipid block with lipid soln.
Because this technical method does not limit the relevant technologies parameter, can't control product quality in process of production.Cause large quantities of waste products, caused great waste to resource.
The present invention has carried out technological improvement to the liposome of describing in the Chinese patent 02153385.7 with the preparation method of lipid on the basis of existing technology, has overcome the defective of prior art, has obtained the better liposome lipid of a kind of quality.
Summary of the invention:
The invention provides a kind of liposome lipid, can be called composite phospholipid sterin lipid.
This composite phospholipid sterin lipid is particularly suitable for the preparation of eye drop, especially is fit to the preparation of Indomethacin liposome eye drops.
Therefore the invention provides a kind of preparation method of composite phospholipid sterin lipid, described composite phospholipid sterin iipidomic becomes: soybean phospholipid, cholesterol and vitamin E is characterized in that preparation method is as follows:
Step 1. takes by weighing soybean phospholipid, cholesterol and vitamin E, makes its dissolving with dehydrated alcohol, and mix homogeneously filters.
Step 2. on rotary evaporator, after the dehydrated alcohol film forming is removed in decompression, obtains the lipid block with lipid soln.
The prescription of preferred composite phospholipid sterin lipid of the present invention and being prepared as follows:
Prescription:
Preparation method:
1. take by weighing refining soybean phospholipid, cholesterol and the vitamin E of recipe quantity, make its dissolving, mix homogeneously with dehydrated alcohol;
With lipid soln on rotary evaporator, the decompression remove dehydrated alcohol, obtain the lipid block.
The prescription of most preferred composite phospholipid sterin lipid of the present invention and being prepared as follows:
Prescription:
Preparation method
1. soybean phospholipid 18.17g, the cholesterol 3.85g and the vitamin E 0.0112g that take by weighing recipe quantity put in the beaker, make its dissolving with 60 ℃ of dehydrated alcohol 200ml water-baths, and mix homogeneously filters.
With lipid soln on rotary evaporator, after the dehydrated alcohol film forming is removed in 50 ℃ of decompressions of water-bath, obtain the lipid block.
Composite phospholipid sterin lipid of the present invention is particularly suitable for preparing Indomethacin liposome eye drops, Indomethacin liposome eye drops prescription composition
Preparation method, step is as follows:
Step 1. is the borate buffer solution of 6.7-7.3 by prescription preparation pH, and filtration sterilization is for subsequent use;
Step 2. is with composite phospholipid sterin lipid borate buffer solution aquation;
The indomethacin that step 3. takes by weighing recipe quantity dissolves with borax soln;
Step 4. is regulated pH value with boric acid again with in the 3 composite phospholipid sterin lipids that join with the buffer aquation;
Step 5. high pressure homogenizer is made liposome through 0.1 μ m microporous filter membrane degerming.
Under step 6. sterile working, packing and get final product.
Wherein
The compound method of borate buffer solution is as follows: take by weighing boric acid 2.5g Borax 0.05g, add water and make dissolving and be diluted to scale.
The compound method of borax soln is as follows: take by weighing the surplus Borax and add water and make dissolving and be diluted to scale.
The compound method of boric acid solution is as follows: take by weighing surplus boric acid and add water and make dissolving and be diluted to scale.
The compound method of composite phospholipid sterin lipid is as follows:
Prescription: soybean phospholipid 165g, cholesterol 35g, vitamin E 0.2g
Preparation method:
1. take by weighing soybean phospholipid, cholesterol and the vitamin E of recipe quantity, make its dissolving with dehydrated alcohol, mix homogeneously filters.
With lipid soln on rotary evaporator, the decompression remove the dehydrated alcohol film forming after, obtain the lipid block.
Liposome membrane mainly is comprised of soybean phospholipid and cholesterol.Soybean phospholipid is as raw material take the refining soybean phospholipid powder that extracts from Semen sojae atricolor; through repeatedly refining extraction of advanced technologies; thereby the yellow that obtains to brown semisolid becomes block; it is multiple phosphatidyl mixture; its main component is phosphatidylcholine (PC), PHOSPHATIDYL ETHANOLAMINE (PE; claim again cephalin) and phosphatidylinositols (PI claims again lipositol).For product quality is controlled, we are on the basis of strict raw soybeans phospholipid PC content, increase is carried out assay to the soybean phospholipid in the composite phospholipid sterin lipid, cholesterol, by the quantitative analysis to main component in the composite phospholipid sterin lipid, control and estimate the quality of product.
Table 1 sample soybean phospholipid and cholesterol mass ratio (every g soybean phospholipid is than the g number of cholesterol)
| Lot number | 100901 | 100902 | 100903 | 100904 |
| Measurement result | 0.204g | 0.211g | 0.213g | 0.208g |
Table 2 long term test examination result
The result shows that sample was stored 12 months under 6 ℃ of conditions of temperature, pH value, mean diameter, osmotic pressure, envelop rate, content etc. have no significant change; Peroxide value increases to some extent, but up to specification; Related substance increases to some extent, but up to specification, the interpret sample steady quality.
The invention has the advantages that:
Be used for the preparation of Indomethacin liposome eye drops with the Liposomes of the inventive method preparation, the product that obtains has the stability better than prior art,
The Indomethacin liposome eye drops stability experiment result of table 3 prior art preparation:
The product that prior art obtains, through the placement of 9 months (6 ℃ of conditions of temperature), related substance 2.25%, peroxide value 11 is much larger than the present invention.
The specific embodiment:
Further specify by the following examples the present invention, but not as limitation of the present invention.
Embodiment 1
Preparation composite phospholipid sterin lipid
One. prescription
Two. technique:
1. take by weighing refining soybean phospholipid 82.4g, cholesterol 17.5g and the vitamin E 0.1001g of recipe quantity, make its dissolving, mix homogeneously with dehydrated alcohol.
With lipid soln on rotary evaporator, the decompression remove dehydrated alcohol, obtain the lipid block.
Heavy altogether: 99.1g (yield 99.1%)
Cholesterol and soybean phospholipid mass ratio 0.204
Embodiment 2
Prescription:
Operation:
1. soybean phospholipid 18.2g, the cholesterol 3.9g and the vitamin E 0.0112g that take by weighing recipe quantity put in the beaker, make its dissolving with dehydrated alcohol, and mix homogeneously filters.
With lipid soln on rotary evaporator, the decompression remove the dehydrated alcohol film forming after, obtain the lipid block.
Heavy altogether: 21.3g (yield 96.8%)
Cholesterol and soybean phospholipid mass ratio 0.211
Embodiment 3
Prescription:
Operation:
1. take by weighing soybean phospholipid 165.1g, cholesterol 35.2g and the vitamin E 0.2019g of recipe quantity, make its dissolving with dehydrated alcohol, mix homogeneously filters.
With lipid soln on rotary evaporator, the decompression remove the dehydrated alcohol film forming after, obtain the lipid block.
Heavy altogether: 197.4g (yield 98.7%)
Cholesterol and soybean phospholipid mass ratio 0.213
Embodiment 4
Prescription:
Operation:
1. take by weighing soybean phospholipid 330.1g, cholesterol 70.1g and the vitamin E 0.4068g of recipe quantity, make its dissolving with dehydrated alcohol, mix homogeneously filters.
With lipid soln on membrane evaporator, the decompression remove the dehydrated alcohol film forming after, obtain the lipid block.
Heavy altogether: 397.0g (yield 99.3%)
Cholesterol and soybean phospholipid mass ratio 0.208
Embodiment 5
One. Indomethacin liposome eye drops prescription (1L) is (0.4ml:2ml)
Two. technique:
(1) preparation borate buffer solution: take by weighing boric acid 2.5g Borax 0.05g, add water and make dissolving and be diluted to scale.
(2) preparation borax soln: take by weighing Borax 2.4g and add water and make dissolving and be diluted to scale.
(3) preparation boric acid solution: take by weighing boric acid 11.6g and add water and make dissolving and be diluted to scale.
(4) composite phospholipid sterin lipid 75g is added the borate buffer solution aquation;
(5) taking by weighing indomethacin 5g adds borax soln and makes dissolving;
(6) (5) gradation is slowly joined in the composite phospholipid sterin lipid of using the buffer aquation, stir.
(7) add again boric acid solution and regulate in right amount pH value;
(8) be crushed to liposome with high pressure homogenizer.
Claims (1)
1. the preparation method of Indomethacin liposome eye drops is characterized in that, the prescription of described Indomethacin liposome eye drops is as follows:
Preparation method is as follows:
Step 1. preparation pH is the borate buffer solution of 6.7-7.3, and filtration sterilization is for subsequent use;
Step 2. is with composite phospholipid sterin lipid borate buffer solution aquation;
The indomethacin that step 3. takes by weighing recipe quantity dissolves with borax soln;
Step 4. joins the solution of step 3 in the composite phospholipid sterin lipid of using the buffer aquation, regulates pH value with boric acid again;
Step 5. high pressure homogenizer is made liposome through 0.1 μ m microporous filter membrane degerming;
Under step 6. sterile working, packing and get final product;
Wherein, the prescription of described composite phospholipid sterin lipid is:
Preparation method is as follows:
1) takes by weighing refining soybean phospholipid, cholesterol and vitamin E, make its dissolving, mix homogeneously with dehydrated alcohol;
2) with lipid soln on rotary evaporator, the decompression remove dehydrated alcohol, obtain the lipid block.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201210073732 CN102641242B (en) | 2012-03-19 | 2012-03-19 | Method for preparing composite phospholipid sterol lipid |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201210073732 CN102641242B (en) | 2012-03-19 | 2012-03-19 | Method for preparing composite phospholipid sterol lipid |
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| CN102641242A CN102641242A (en) | 2012-08-22 |
| CN102641242B true CN102641242B (en) | 2013-10-16 |
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Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106727328B (en) * | 2017-01-04 | 2020-03-13 | 中国药科大学 | Method for preparing liposome based on ternary complex of medicine-phospholipid-cholesterol |
| CN107961167B (en) * | 2017-12-20 | 2021-03-26 | 吉林国健生命工程科学技术有限公司 | Placenta extract gel preparation and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007046318A1 (en) * | 2005-10-17 | 2007-04-26 | Kowa Co., Ltd. | Liquid preparation for external application containing indomethacin |
| WO2009105534A2 (en) * | 2008-02-21 | 2009-08-27 | Ista Pharmaceuticals | Ophthalmic nsaids as adjuvants |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1206987C (en) * | 2002-11-29 | 2005-06-22 | 孙仁俊 | Indomethacin liposome eye drops |
| CN101095695A (en) * | 2007-08-10 | 2008-01-02 | 孙猛 | Liposome artificial tear eye drops |
-
2012
- 2012-03-19 CN CN 201210073732 patent/CN102641242B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007046318A1 (en) * | 2005-10-17 | 2007-04-26 | Kowa Co., Ltd. | Liquid preparation for external application containing indomethacin |
| WO2009105534A2 (en) * | 2008-02-21 | 2009-08-27 | Ista Pharmaceuticals | Ophthalmic nsaids as adjuvants |
Non-Patent Citations (2)
| Title |
|---|
| 吲哚美辛脂质体滴眼液在家兔眼内的药动学;李兰芳等;《中国医院药学杂志》;20051231;第25卷(第1期);21-23 * |
| 李兰芳等.吲哚美辛脂质体滴眼液在家兔眼内的药动学.《中国医院药学杂志》.2005,第25卷(第1期),21-23. |
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