CN101474154B - 4-(1-phenethyl)-1,3-dihydroxy benzene liposome and preparation method thereof - Google Patents
4-(1-phenethyl)-1,3-dihydroxy benzene liposome and preparation method thereof Download PDFInfo
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- CN101474154B CN101474154B CN2009100455129A CN200910045512A CN101474154B CN 101474154 B CN101474154 B CN 101474154B CN 2009100455129 A CN2009100455129 A CN 2009100455129A CN 200910045512 A CN200910045512 A CN 200910045512A CN 101474154 B CN101474154 B CN 101474154B
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Abstract
The invention relates to the technical field of medicine and cosmetics, in particular to lipidosome preparation formulation of 4-(1- phenethyl)-1 and 3-dihydroxy benzene and a preparation method thereof. The invention prepares the 4-(1- phenethyl)-1, 3-dihydroxy benzene into lipidosome, overcomes the defects of the insufficient application of existing 4-(1- phenethyl)-1 and 3-dihydroxy benzene in percutaneous administration preparation and cosmetics, improves the stability and percutaneous performance of the 4-(1- phenethyl)-1and 3-dihydroxy benzene and reduces the acrimony of the 4-(1- phenethyl)-1 and 3-dihydroxy benzene for the skin, thus better exerting the healing effect.
Description
Technical field
The present invention relates to medicine and cosmetics technical field, is 4-(1-phenethyl)-1, liposome dosage form of 3-dihydroxy benzenes and preparation method thereof.
Background technology
4-(1-phenethyl)-1, the 3-dihydroxy benzenes is a kind of tyrosinase inhibitor, effect with blast skin and hair and anti-senile plaque, 4-(1-phenethyl)-1 has been arranged at present, the 3-dihydroxy benzenes be used for the report (" diphenylmethane derivatives is as the purposes of tyrosinase inhibitor ", number of patent application 200480014939.8) of cosmetics or medicine for removing speckle as tyrosinase inhibitor.But because 4-(1-phenethyl)-1, the 3-dihydroxy benzenes is a phenolic compound, water solublity and fat-soluble all relatively poor, the skin transmitance is lower, and easily oxidized, has certain zest, so limited 4-(1-phenethyl)-1, the application of 3-dihydroxy benzenes in percutaneous drug administration preparation and cosmetic field.
Liposome is the hydrophilic vesicle that is made of phospholipid bilayer, have the encapsulated stability of drug of raising, promote advantages such as drug transdermal absorbs, the action time of prolong drug, reduction medicine irritation, but do not see that so far the 3-dihydroxy benzenes is made the report of liposome dosage form with 4-(1-phenethyl)-1.
Summary of the invention
The invention provides a kind of 4-(1-phenethyl)-1, liposome dosage form of 3-dihydroxy benzenes and preparation method thereof, to overcome existing 4-(1-phenethyl)-1, the deficiency of 3-dihydroxy benzenes in percutaneous drug administration preparation and cosmetic applications, improve 4-(1-phenethyl)-1, the stability of 3-dihydroxy benzenes, transdermal performance reduce 4-(1-phenethyl)-1, the 3-dihydroxy benzenes makes it bring into play curative effect better to the zest of skin.
4-of the present invention (1-phenethyl)-1, the liposome component and the proportioning of 3-dihydroxy benzenes are as follows:
Wherein, said matrix material is selected from the 1-2 kind in soybean lecithin, Ovum Gallus domesticus Flavus lecithin, distearoyl phosphatidylcholine, dipalmitoyl phosphatidyl choline, ceramide, the dimyristoyl phosphatidyl choline, or is selected from 1-2 kind in soybean lecithin, Ovum Gallus domesticus Flavus lecithin, distearoyl phosphatidylcholine, dipalmitoyl phosphatidyl choline, ceramide, the dimyristoyl phosphatidyl choline and adds 1-2 kind in sodium cholate, poloxamer 188, the cholesterol; Stabilizing agent is selected from the 1-3 kind in glycerol, propylene glycol, PEG400, the ethanol.
4-of the present invention (1-phenethyl)-1,3-dihydroxy benzenes method for preparing lipidosome is as follows:
1) preparation lipid soln:
With 4-(1-phenethyl)-1,3-dihydroxy benzenes and matrix material and stabilizing agent are dissolved in organic solvent by proportioning, 50 ℃-80 ℃ dissolvings down, make lipid soln, and said organic solvent is selected from the 1-2 kind in chloroform, methanol, ethanol, the dichloromethane;
2) preparation lipid aqueous dispersions:
Above-mentioned lipid soln is put in the Rotary Evaporators, and rotating thin film evaporation organic solvent forms lipid membrane routinely, routinely with lipid membrane hydration, vibration, makes the lipid aqueous dispersions again; Or directly lipid soln is injected aqueous solution, vibration mixes, and makes the lipid aqueous dispersions;
3) preparation liposome:
Above-mentioned lipid aqueous dispersions is carried out second emulsifying, promptly get 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome, said second emulsifying method can adopt high pressure homogenize emulsifying, mechanical agitation emulsifying, ultrasonic emulsification or colloid mill emulsifying.
Detect through Ma Erwen particle diameter instrument, the mean diameter of liposome of the present invention is 85.2nm.
4-of the present invention (1-phenethyl)-1,3-dihydroxy benzenes liposome mainly contains following several respects advantage:
1) 4-(1-phenethyl)-1, the stability of 3-dihydroxy benzenes have been improved.Liposome is rolled in pharmaceutical pack in the middle of the lipid bimolecular, can avoid the destruction of unstable factors such as light, oxygen, acid, alkali to medicine, thereby improves stability of drug.Liposome not only improves the external stability of medicine, and can improve medicine stability in vivo, thus action time in the prolong drug body.
2) reduce 4-(1-phenethyl)-1, the zest of 3-dihydroxy benzenes.4-(1-phenethyl)-1, the 3-dihydroxy benzenes itself has very strong zest, and liposome is rolled in pharmaceutical pack in the middle of the bimolecular, can avoid the zest that in use produces.
3) improve 4-(1-phenethyl)-1, the transdermal performance of 3-dihydroxy benzenes.Liposome is the pharmaceutical carrier that is made of the class lipid bilayer, has bigger similarity and histocompatibility with biological tissue, can improve the skin penetration of medicine.Liposome can not only improve the skin penetration of medicine, and more medicine is trapped between epidermis and the corium, and enters the dose minimizing of blood system, thereby can effectively avoid the general untoward reaction.Liposome promotes the medicine skin penetration mainly by mechanism of action such as hydration, fusion, penetrations.
4 for most of cosmetic formulations, its substrate is hydrophilic or emulsion-type substrate, this is hydrophilic or lipophilic composition with regard to the component in requiring to fill a prescription, 4-(1-phenethyl)-1,3-dihydroxy benzenes hydrophilic and lipotropy are all not strong, this is to containing 4-(1-phenethyl)-1, and the preparation of 3-dihydroxy benzenes cosmetics brings difficulty.Liposome is a kind of highly hydrophilic pharmaceutical carrier, with 4-(1-phenethyl)-1, the 3-dihydroxy benzenes can obviously improve the hydrophilic of medicine with liposomal encapsulated, make and contain 4-(1-phenethyl)-1, the pharmaceutical preparation of 3-dihydroxy benzenes and the preparation of cosmetics are more simple, convenient.
The specific embodiment
Now in conjunction with the embodiments the present invention is described in detail.
Embodiment 1: preparation 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome
Get 4-(1-phenethyl)-1,3-dihydroxy benzenes 1g, soybean lecithin 3.8g, cholesterol 1.2g, place the round-bottomed flask of 1000ml, add 50ml chloroform and methanol mixed solution (chloroform: methanol=1: 1), dissolve down at 55 ℃, put rotating thin film evaporation in 55 ℃ of waters bath with thermostatic control, make the formation lipid membrane; Adding is preheated to 55 ℃ distilled water 994ml then, hydration, and vibration gets colostrum; Colostrum is carried out second emulsifying with high pressure homogenizer, can obtain 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome 1000g.
Embodiment 2: preparation 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome
Get 4-(1-phenethyl)-1,3-dihydroxy benzenes 80g, soybean lecithin 20g, usefulness ethanol 100ml with its dissolving, gets lipid soln under 75 ℃ of heating in water bath; Get glycerol 700g, distilled water 100ml, mix homogeneously, heating in water bath to 75 ℃, water.Lipid soln is made a bet into aqueous phase at 75 ℃, and jolting is even, gets colostrum.Colostrum put carries out second emulsifying in the high pressure homogenizer, get final product 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome 1000g.
Embodiment 3: preparation 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome
Get 4-(1-phenethyl)-1,3-dihydroxy benzenes 100g, Ovum Gallus domesticus Flavus lecithin 50g, cholesterol 50g, ceramide 20g puts in the revolving bottle, adds the 200ml dichloromethane, under 50 ℃ of heating,, put rotating thin film evaporation in 50 ℃ of waters bath with thermostatic control, make the formation lipid membrane its dissolving; Adding is preheated to 65 ℃ distilled water 780ml then, hydration, and vibration gets colostrum; Colostrum is carried out second emulsifying with ultrasonic emulsification, can obtain 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome 1000g.
Example executes 4: preparation 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome
Get 4-(1-phenethyl)-1,3-dihydroxy benzenes 30g, distearoyl phosphatidylcholine 30g, dipalmitoyl phosphatidyl choline 50g, cholesterol 10g, usefulness ethanol 200ml with its dissolving, gets lipid soln under 70 ℃ of heating in water bath; Get propylene glycol 300g, PEG400 g, distilled water 180ml, mix homogeneously, heating in water bath to 70 ℃, water.Lipid soln is made a bet into aqueous phase at 70 ℃, and jolting is even, gets colostrum.Again colostrum is put and is carried out second emulsifying in the high pressure homogenizer, get final product 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome 1000g.
Embodiment 5: preparation 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome
Get 4-(1-phenethyl)-1,3-dihydroxy benzenes 10g, dimyristoyl phosphatidyl choline 80g place the round-bottomed flask of 1000ml, add the 200ml chloroform, under 60 ℃,, put rotating thin film evaporation in 60 ℃ of waters bath with thermostatic control, make the formation lipid membrane above-mentioned lipid components dissolving; Adding is preheated to 60 ℃ distilled water 910ml then, hydration, and vibration gets colostrum; Colostrum is carried out second emulsifying with colloid mill, can obtain 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome 1000g.
Embodiment 6: preparation 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome
Get 4-(1-phenethyl)-1,3-dihydroxy benzenes 40g, soybean lecithin 80g, usefulness ethanol 200ml with its dissolving, gets lipid soln under 80 ℃ of heating in water bath; This lipid soln is dispersed in the 680ml distilled water that is heated to 80 ℃, stirs, mix, get colostrum; Colostrum is carried out second emulsifying with the mechanical agitation emulsification instrument, get final product 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome 1000g.
Embodiment 7: preparation 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome
Get 4-(1-phenethyl)-1,3-dihydroxy benzenes 80g, soybean lecithin 20g, (dichloromethane: ethanol=1: 2) 65 ℃ of following water-baths are dissolved, and put in the rotary flask to use 200ml dichloromethane and alcohol mixed solution, thin film evaporation is rotated in 65 ℃ of waters bath with thermostatic control down, makes the formation lipid membrane; Take by weighing 130g poloxamer 188, be dissolved in the distilled water of 770ml, get water.With dissolving, the prepared lipid membrane of hydration under 65 ℃ of water-baths of water, after stirring, get colostrum.Colostrum is carried out second emulsifying with high pressure homogenizer, can obtain 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome 1000g.
Embodiment 8: preparation 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome
Get 4-(1-phenethyl)-1,3-dihydroxy benzenes 80g, soybean lecithin 12g, Ovum Gallus domesticus Flavus lecithin 10g, (chloroform: ethanol=1: 2) 70 ℃ of following water-baths are dissolved, and put in the rotary flask to use 200ml chloroform and alcohol mixed solution, the rotating thin film evaporation makes the formation lipid membrane in 55 ℃ of waters bath with thermostatic control; Get propylene glycol 500g, ethanol 100g, be dissolved in the 298ml distilled water, get water.With aqueous phase dissolved, the prepared lipid membrane of hydration, after stirring, get colostrum.Colostrum is carried out second emulsifying with high pressure homogenizer, can obtain 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome 1000g.
Embodiment 9: preparation 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome
Get 4-(1-phenethyl)-1,3-dihydroxy benzenes 50g, soybean lecithin 20g, cholesterol 2g with 70 ℃ of following water-bath dissolvings of 200ml ethanol, get lipid soln; Take by weighing propylene glycol 600g, be dissolved in the distilled water of 328ml, get water.Lipid soln is made a bet into aqueous phase for 60 ℃, after stirring, get colostrum.Colostrum is carried out second emulsifying with high pressure homogenizer, can obtain 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome 1000g.
Embodiment 10: preparation 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome
Get 4-(1-phenethyl)-1,3-dihydroxy benzenes 50g, soybean lecithin 12g, cholesterol 1g, (chloroform: 65 ℃ of following water-baths dissolvings ethanol=2: 1) get lipid soln to use 100ml chloroform and alcohol mixed solution, put rotating thin film evaporation in 60 ℃ of waters bath with thermostatic control, make the formation lipid membrane; Get propylene glycol 200g, sodium cholate 80g, be dissolved in the distilled water of 657ml, get water.With dissolving, the prepared lipid membrane of hydration under 70 ℃ of water-baths of water, after stirring, get colostrum.Colostrum is carried out second emulsifying with high pressure homogenizer, can obtain 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome 1000g.
4-(1-phenethyl)-1, the experiment of 3-dihydroxy benzenes liposome stability
Experiment divides two groups, be 4-(1-phenethyl)-1,3-dihydroxyphenyl ethanol solution group and 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome group, 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome is by embodiment 6 preparations, every group is repeated 3 batches, with 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome and 4-(1-phenethyl)-1,3-dihydroxyphenyl ethanol solution is placed under 25 ℃ of temperature, relative humidity 75% condition.Every month is respectively with high effective liquid chromatography for measuring 4-(1-phenethyl)-1 wherein after placing, 3-dihydroxy benzenes content 1 time, with 30 days be 1 month, detect 3 months, represent with 1,2,3 successively, first day 4-(1-phenethyl)-1,3-dihydroxy benzenes content is 100%, represents with 0 month, represented with 1,2,3 successively in 3 months, 1,2, March the medicament contg that detects with the ratio of the medicament contg that detected in 0 month, can draw medicament contg and change percentage rate, the results are shown in Table 1.
Table 1:4-(1-phenethyl)-1,3-dihydroxyphenyl ethanol solution, 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome stability compares, n=3
By table 1 as seen, 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome stability is apparently higher than 4-(1-phenethyl)-1,3-dihydroxyphenyl ethanol solution.
Claims (7)
1. a 4-(1-phenethyl)-1, the liposome of 3-dihydroxy benzenes, its component and proportioning are as follows:
Component percentages % (W/V)
4-(1-phenethyl)-1,3-dihydroxy benzenes 0.1-10
Matrix material 0.5-15
Stabilizing agent 0-70
Distilled water surplus
Said matrix material is selected from the 1-2 kind in soybean lecithin, Ovum Gallus domesticus Flavus lecithin, distearoyl phosphatidylcholine, dipalmitoyl phosphatidyl choline, ceramide, the dimyristoyl phosphatidyl choline, or is selected from 1-2 kind in soybean lecithin, Ovum Gallus domesticus Flavus lecithin, distearoyl phosphatidylcholine, dipalmitoyl phosphatidyl choline, ceramide, the dimyristoyl phosphatidyl choline and adds 1-2 kind in sodium cholate, poloxamer 188, the cholesterol; Said stabilizing agent is selected from the 1-3 kind in glycerol, propylene glycol, PEG400, the ethanol.
2. by the described 4-of claim 1 (1-phenethyl)-1,3-dihydroxy benzenes liposome is characterized in that said matrix material is soybean lecithin or Ovum Gallus domesticus Flavus lecithin, and content is 1%-%5; Stabilizing agent is glycerol or ethanol, and content is 40%-70%.
3. by the described 4-of claim 2 (1-phenethyl)-1,3-dihydroxy benzenes liposome is characterized in that said matrix material is an Ovum Gallus domesticus Flavus lecithin, and content is 2%; Stabilizing agent is a glycerol, and content is 65%.
4. claim 1 or 2 or 3 described 4-(1-phenethyl)-1, the preparation method of 3-dihydroxy benzenes liposome, step is as follows:
1) preparation lipid soln: press proportioning with 4-(1-phenethyl)-1,3-dihydroxy benzenes, matrix material and stabilizing agent are dissolved in organic solvent under 50 ℃-80 ℃, make lipid soln, said organic solvent is selected from the 1-2 kind in chloroform, methanol, ethanol, the dichloromethane;
2) preparation lipid aqueous dispersions: above-mentioned lipid soln is put Rotary Evaporators rotating thin film evaporation organic solvent, form lipid membrane; With lipid membrane hydration, vibration, make the lipid aqueous dispersions; Or directly lipid soln is injected aqueous solution, vibration mixes, and makes the lipid aqueous dispersions;
3) preparation of liposome: above-mentioned lipid aqueous dispersions is carried out second emulsifying, make 4-(1-phenethyl)-1,3-dihydroxy benzenes liposome, said second emulsifying method is selected from high pressure homogenize emulsifying, mechanical agitation emulsifying, ultrasonic emulsification or colloid mill emulsifying.
5. by the described 4-of claim 4 (1-phenethyl)-1, the preparation method of 3-dihydroxy benzenes liposome is characterized in that said organic solvent is chloroform, alcoholic acid mixed liquor, and proportioning is 1: 10-10: 1, and temperature is controlled at 60 ℃-75 ℃; Said second emulsifying method is high pressure homogenize emulsifying or ultrasonic emulsification.
6. by the described 4-of claim 5 (1-phenethyl)-1, the preparation method of 3-dihydroxy benzenes liposome is characterized in that said organic solvent is an ethanol, and temperature is controlled between 70 ℃-75 ℃; The second emulsifying method is high pressure homogenize emulsifying.
7. claim 1 or 2 or 3 described 4-(1-phenethyl)-1, the application of 3-dihydroxy benzenes liposome in preparation percutaneous drug administration preparation or cosmetics.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1798550A (en) * | 2003-05-30 | 2006-07-05 | 西姆莱斯有限责任两合公司 | Use of diphenylmethane derivatives as tyrosinase inhibitors |
| WO2007077258A1 (en) * | 2006-01-05 | 2007-07-12 | Symrise Gmbh & Co. Kg | Stabilized preparations comprising phenolic compounds and benzophenones |
| WO2007077260A9 (en) * | 2006-01-05 | 2007-09-13 | Symrise Gmbh & Co Kg | Formulations of low oil content comprising diphenylmethane derivatives |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1798550A (en) * | 2003-05-30 | 2006-07-05 | 西姆莱斯有限责任两合公司 | Use of diphenylmethane derivatives as tyrosinase inhibitors |
| WO2007077258A1 (en) * | 2006-01-05 | 2007-07-12 | Symrise Gmbh & Co. Kg | Stabilized preparations comprising phenolic compounds and benzophenones |
| WO2007077260A9 (en) * | 2006-01-05 | 2007-09-13 | Symrise Gmbh & Co Kg | Formulations of low oil content comprising diphenylmethane derivatives |
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