CN103462934B - Preparation method of allyl isothiocyanate nanometer lipid carrier - Google Patents
Preparation method of allyl isothiocyanate nanometer lipid carrier Download PDFInfo
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- CN103462934B CN103462934B CN201310418572.7A CN201310418572A CN103462934B CN 103462934 B CN103462934 B CN 103462934B CN 201310418572 A CN201310418572 A CN 201310418572A CN 103462934 B CN103462934 B CN 103462934B
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Abstract
The invention discloses a preparation method of an allyl isothiocyanate nanometer lipid carrier. The preparation method comprises the following steps of dissolving allyl isothiocyanate, a solid lipid material, liquid oil, and a lipid soluble emulsifier in an organic solvent, removing the organic solvent, and heating the resulting product to 60-100 DEG C for melting to obtain an organic phase; dissolving a long-circulating adjuvant, a water soluble emulsifier, and an additive in injection water, and heating the resulting solution to 60-100 DEG C to obtain a water phase; and mixing the organic phase and the water phase at the temperature of 60-100 DEG C to prepare a pre-emulsion; and carrying out ultrasonic or high-pressure homogenizing treatment on the pre-emulsion, and pouring the homogenized product into ice water so as to obtain the allyl isothiocyanate nanometer lipid carrier comprising the following ingredients in percentages by weight: 0.01-8% of allyl isothiocyanate, 0.50-15% of solid lipid material, 0-15% of liquid oil, 0.10-15% of emulsifier, 0-15% of long-circulating adjuvant, 0-15% of additive and the balance of injection water.
Description
Technical field
The present invention relates to field of pharmaceutical preparations, disclose a kind of preparation method of Allyl isothiocyanate nano-lipid carrier, more particularly, the present invention relates to the preparation method that a kind of reticuloendothelial system phagocytic helped avoid in body also can stablize the Allyl isothiocyanate nano-lipid carrier of storage.
Background technology
Allyl isosulfocyanate (Allyl isothiocyanate, AITC) be the main taste compound of mustard oil, because it has distinctive taste and antibiotic property, in recent years about research finds the growth of its energy anticancer, also can use as soil sterilants agriculturally substituting Celfume, therefore allyl isosulfocyanate food additive, food antibacterial anticorrosion, medical treatment is anticancer and be with a wide range of applications in soil disinfection etc.
Allyl isosulfocyanate is a kind of compound had compared with high anti-tumor activity, its antimicrobial spectrum is wider, and toxicity is lower, optionally can act on tumor cell, and intact animal's hemopoietic system and immune system are not affected, animal toleration is good, to Ehrlich tumor, S180 ehrlich ascites carcinoma, Lewis lung cancer, La795 adenocarcinoma of lung, cancer of pancreas, the entity tumors such as gastric cancer all have good inhibitory action, allyl isosulfocyanate effectively can block cancerous cell in G0 ~ G1 phase, and then the growth of inhibition tumor cell, promote the apoptosis of tumor cell, , display allyl isosulfocyanate is the very potential cancer treatment drugs of one.Allyl isosulfocyanate molecular formula: C4H5NS, molecular weight 99.15.
But the intense stimulus abnormal smells from the patient of allyl isosulfocyanate, strong volatility, the in atmosphere oxidizable rotten and easy range of application characteristics such as human body generation injury having been had a strong impact on to it.Therefore, adopt saturated water solution method, with beta-schardinger dextrin-, the process of micro encapsulation enclose is carried out to allyl isosulfocyanate and effectively can eliminate its penetrating odor and the undesirable feature such as volatilization, oxidation, be more convenient for storing and application.
Due to allyl isosulfocyanate, dissolubility is low in aqueous, large to body zest after injection, Half-life in vivo is short, limit its application clinically, therefore improve allyl isosulfocyanate dissolubility with using Modern preparations technology effective is needed, reduce zest, prolong drug action time in vivo and localized clusters amount, better play antitumaous effect.
Nano-lipid carrier (nanostructred lipid carriers, NLC) be by solid lipid nanoparticle (solidlipid nanoparticles, what SLN) develop a kind ofly effectively can avoid the novel drug-loading system that put procedure Chinese medicine is arranged, envelop rate is lower outward, solid lipid nanoparticle (SLN) Problems existing is, it is made up of single matrix material, in preparation process after high pressure homogenize cooling, lipid trends towards forming more regular crystallization, thus causes the outer row that is wrapped medicine or crystallization in the aqueous phase of SLN dispersion.And NLC joins in Solid lipid by obtaining liquid fatty substance under room temperature, thus causing the degree of mixing of crystal to increase, making carrier have higher crystal defect, thus can hold more drug molecule.To be mixed by Solid lipid and liquid fatty substance incompatible with its space just because of NLC and form, make it have special nanostructured.
Solid lipid material is the carrier of allyl isosulfocyanate, and different ingredients need select corresponding matrix material as thing carrier, and different pharmaceutical carriers need screen different emulsifying agents and additives kind; Fluid oil guarantees that drug-carrying nanometer particle exists with irregular crystal form, as existed with solid-state crystal defect or unformed form, the effect of emulsifying agent and additives forms stable emulsifying agent film packaging medicine and matrix material, simultaneously, long circulating adjuvant can be added, effect is modified the surface of nanoparticle, makes it avoid in vivo by liver, the engulfing of spleen reticuloendothelial system.
In sum, allyl isosulfocyanate is made nano-lipid carrier, improve bioavailability, reduce zest, prolong the objects such as medicine surplus action time.Therefore, the novel form researching and developing allyl isosulfocyanate is very important.
Summary of the invention
For prior art, the invention provides a kind of novel form carrier of allyl isosulfocyanate---the preparation method of Allyl isothiocyanate nano-lipid carrier, Allyl isothiocyanate nano-lipid carrier can overcome the phenomenon that solid lipid nanoparticle put procedure Chinese medicine is arranged, poor stability, envelop rate are low outward; Allyl isothiocyanate nano-lipid carrier drug loading is higher, performance is more stable, and preparation Absorbable organic halogens is stored.Another object of the present invention is to provide a kind of method preparing Allyl isothiocyanate nano-lipid carrier of the present invention.
Allyl isosulfocyanate is wrapped in lipoid core by the present invention, adds the dissolubility of allyl isosulfocyanate, greatly reduces zest, and preparation reaches the clearer and more definite effect such as targeting, controlled release to a certain extent, and physicochemical properties are stablized.
For achieving the above object, the invention provides a kind of preparation method of Allyl isothiocyanate nano-lipid carrier, described Allyl isothiocyanate nano-lipid carrier is grouped into by each one-tenth of following percetage by weight: allyl isosulfocyanate 0.01 ~ 8%; Solid lipid material 0.50 ~ 15%; Fluid oil 0 ~ 15%; Emulsifying agent 0.10 ~ 15%; Long circulating adjuvant 0 ~ 15%; Additives 0 ~ 15%; Surplus is water for injection; The preparation method of described Allyl isothiocyanate nano-lipid carrier comprises the following steps:
Allyl isosulfocyanate, Solid lipid material, fluid oil, fat-soluble emulsifier are dissolved in organic solvent, then remove organic solvent, and be heated to 60 ~ 100 DEG C of meltings, to form organic facies;
Long circulating adjuvant, water soluble emulsifier, additives are dissolved in water for injection, and are heated to 60 ~ 100 DEG C, to form aqueous phase;
At 60 ~ 100 DEG C of temperature, by described organic facies and aqueous phase mixing under stirring or shear conditions, to prepare colostrum;
Ultrasonic or high pressure homogenize process is carried out to described colostrum, and in impouring frozen water, thus obtained Allyl isothiocyanate nano-lipid carrier; Or first do not remove organic facies organic solvent, at the temperature of 0 ~ 100 DEG C, by described organic facies and aqueous phase mixing under stirring or shear conditions, prepare colostrum, ultrasonic or high pressure homogenize process is carried out by described, adopt reduction vaporization or vacuum drying method removing organic solvent again, obtain Allyl isothiocyanate nano-lipid carrier.
Preferably, described organic solvent is selected from dichloromethane, chloroform, acetone, methanol, ethanol, ether, oxolane or isopropyl alcohol and combination in any thereof.
Preferably, freeze drying protectant is added further to make lyophilized formulations to described obtained Allyl isothiocyanate nano-lipid carrier.
Again preferably, described freeze drying protectant is selected from trehalose, sucrose, mannitol, glucose, sodium chloride, lactose, sorbose, dextran, glycerol or glycine and combination in any thereof.
The Allyl isothiocyanate nano-lipid carrier prepared by the preparation method of Allyl isothiocyanate nano-lipid carrier of the present invention has the following advantages:
1. Allyl isothiocyanate nano-lipid carrier of the present invention improves the dissolubility of allyl isosulfocyanate, reduce zest, prolong drug action time in vivo and localized clusters amount, better performance antitumaous effect, reduce the toxic and side effects of allyl isosulfocyanate, improve the toleration of body.
2. preparation of the present invention can overcome solid lipid nanoparticle put procedure Chinese medicine and arranges outward, the phenomenon that envelop rate is low, and Allyl isothiocyanate nano-lipid carrier drug loading is higher, performance is more stable, and preparation Absorbable organic halogens is stored.
3. compared with the Emulsion of allyl isosulfocyanate, liposome, preparation of the present invention is modified by long circulating adjuvant nanoparticle surface, help avoid engulfing of liver spleen reticuloendothelial system in body, and there is slow-release function, can prolong drug circulation time in vivo.
Detailed description of the invention
In order to make object of the present invention, technical scheme and advantage clearly understand, below in conjunction with embodiment, the present invention is further elaborated.Should be appreciated that specific embodiment described herein only in order to explain the present invention, be not intended to limit the present invention.
Allyl isosulfocyanate is wrapped in lipoid core by the present invention, adds the dissolubility of allyl isosulfocyanate, greatly reduces zest, and preparation reaches the clearer and more definite effect such as targeting, controlled release to a certain extent, and physicochemical properties are stablized.
Allyl isothiocyanate nano-lipid carrier of the present invention, it is made up of the treatment allyl isosulfocyanate of effective dose, solid lipid material, fluid oil, emulsifying agent, long circulating adjuvant and water for injection substantially.
Specifically, in the present embodiment, Allyl isothiocyanate nano-lipid carrier provided by the invention contains following ingredients:
The triglyceride category that described Solid lipid material comprises is in three stearic acid, three Palmic acids, trilauryl, three oleic acid etc., the glyceride of long-chain fatty acid, partial glyceride is glyceryl monostearate, contains list, two, the synthetic glyceride of triglyceride etc. and compound thereof; Described fatty acid is stearic acid, Palmic acid, docosanoic acid, sad, myristic acid, and steroid, comprises cholesterol, and paraffin paper class comprises spermol cetylate, spermol hexadecylic acid fat, microcrystalline wax and composition thereof.
Described fluid oil is selected from crude vegetal, as soybean oil, Oleum Arachidis hypogaeae semen, olive oil, safflower oil, the medium chain fatty acid glycerine acid of chain length between C8 ~ C10, oleic acid, linoleic acid, isopropyl myristate, vitamin E, vitamin A, vitamin lipid, preferably, this fluid oil is soybean oil, the medium chain fatty glyceride of chain length between C8 ~ C10 or vitamin E.
Described emulsifying agent comprises fat-soluble emulsifier and water soluble emulsifier, described fat-soluble emulsifier is selected from phospholipid, it comprises lecithin, lecithin and composition thereof, soybean lecithin, Ovum Gallus domesticus Flavus lecithin, hydrolecithin, the smooth class of fatty acid Pyrusussuriensis, as Span60, Span80, poly yamanashi esters, as Tween60, Tween80 and combination in any thereof, described water soluble emulsifier is selected from polyoxyethylene, poiyoxypropylene copolymer class, as Poloxamer series, Pluronic series, polyoxyethylene fatty acid lipid, polyoxyethylene aliphatic alcohol ether class and combination in any thereof, preferably, this emulsifying agent is lecithin, hydrolecithin, Poloxamer188, Span60, Span80 or Tween80,
Described long circulating adjuvant to be PEG molecular weight be 1000 ~ 10000 stearate, PEG molecular weight is at 1000 ~ 10000 vitamin e succinate, PEG stearate and molecular weight are the mixture of the PEG of 200 ~ 10000, Myrj class, Brij class, PEG-DSPE, PEG-dipalmitoyl phosphatidyl choline, PEG-DPPE, ganglioside, polyacrylamide, chitosan, Polyethylene Glycol gathers cetyl itrile group propionic ester, molecular weight is the PEG of 200 ~ 10000, PVP or PVA and combination in any thereof, preferably, the lipid that this PEG modifies to be PEG molecular weight be 1000 ~ 5000 stearate or vitamin E polyethylene glycol succinate, preferably, the lipid that this PEG modifies to be PEG molecular weight be 1000 ~ 5000 stearate or vitamin E polyethylene glycol succinate.
Allyl isosulfocyanate long-circulating nanoliposome carrier of the present invention comprises the additives of 0 ~ 10wt% further, preferably include the additives of 0 ~ 5wt%, described additives can play increases preparation stability, regulate osmotic pressure, antioxidative effect, be selected from osmotic pressure regulator, as glycerol, propylene glycol, mannitol etc., interfacial film stabilizing agent, as oleic acid, enuatrol etc., complexing of metal ion agent, as EDTA, edetate disodium salt; Antioxidant, as vitamin C, vitamin E etc.; Molecular weight is PEG, PVP or PVA and the combination in any thereof of 200 ~ 10000, antiseptic, as benzalkonium bromide, Benzalkonii Chloridum, parabens, Pyrusussuriensis acids; Preferably, these additives are glycerol, mannitol, enuatrol, EDTA, benzalkonium bromide, vitamin E, PEG and combination in any thereof.
In the preparation, its preparation method comprises the following steps Allyl isothiocyanate nano-lipid carrier of the present invention:
(1) allyl isosulfocyanate, Solid lipid material, fluid oil, fat-soluble emulsifier are dissolved in organic solvent, then by organic solvent such as removing such as method such as decompression rotary evaporation or vacuum drying etc., and are heated to 60 ~ 100 DEG C of meltings to form organic facies;
(2) long circulating adjuvant, water soluble emulsifier, additives are dissolved in water for injection, and are heated to 60 ~ 100 DEG C, to form aqueous phase;
(3) at the temperature of 60 ~ 100 DEG C, by described organic facies and aqueous phase mixing under stirring or shear conditions, to prepare colostrum;
(4) ultrasonic or high pressure homogenize process is carried out to described colostrum, thus obtained Allyl isothiocyanate nano-lipid carrier.
Can frozen dried be carried out to obtained Allyl isothiocyanate nano-lipid carrier further or preserve as 4 DEG C of lower seals, to the technique that obtained Allyl isothiocyanate nano-lipid carrier carries out frozen dried be wherein: by 1 ~ 40%(weight ratio) freeze drying protectant be dissolved in the aqueous dispersion of Allyl isothiocyanate nano-lipid carrier of the present invention, this freeze drying protectant is selected from trehalose, mannitol, sucrose, glucose, sodium chloride, lactose, sorbitol, dextran, glycerol or glycine and combination in any thereof, better to ensure forming lyophilized powder crystal formation, then be divided in cillin bottle, and be placed in freezer dryer-45 DEG C of pre-freeze 2.5h, then-50 DEG C are cooled to 5 DEG C/h, maintain 10h, 0 DEG C is warming up to again with 5 DEG C/h, maintain 8h, finally be warming up to 10 DEG C insulation 10h after outlet, jump a queue and seal.
Embodiment one
A kind of Allyl isothiocyanate nano-lipid carrier, it consists of: allyl isosulfocyanate 5mg, GMS60mg, MCT20uL, lecithin 150mg, dehydrated alcohol 5mL, PEG200020mg, Tween8040mg, water for injection 50mL.
Preparation method is as follows:
Allyl isosulfocyanate, GMS, MCT, lecithin are dissolved in dehydrated alcohol, decompression rotary evaporation removing dehydrated alcohol, and are heated to 80 DEG C of meltings to form organic facies; PEG2000, Tween80 are dissolved in water for injection, and are heated to 80 DEG C, to form aqueous phase; At the temperature of 80 DEG C, under agitation by described organic facies and aqueous phase mixing, to prepare colostrum; High pressure homogenize process is carried out to described colostrum, and in impouring frozen water, thus obtained Allyl isothiocyanate nano-lipid carrier.
The drug loading and the envelop rate that measure Allyl isothiocyanate nano-lipid carrier are respectively 7.82% and 87.6%
Embodiment two
A kind of Allyl isothiocyanate nano-lipid carrier, it consists of: allyl isosulfocyanate 5mg, GMS60mg, MCT20uL, lecithin 150mg, dehydrated alcohol 5mL, PEG200020mg, Tween8040mg, water for injection 100mL.
Preparation method is as follows:
Allyl isosulfocyanate, GMS, MCT, lecithin are dissolved in dehydrated alcohol, decompression rotary evaporation removing dehydrated alcohol, and are heated to 80 DEG C of meltings to form organic facies; PEG2000, Tween80 are dissolved in water for injection, and are heated to 80 DEG C, to form aqueous phase; At the temperature of 80 DEG C, under agitation by described organic facies and aqueous phase mixing, to prepare colostrum; High pressure homogenize process is carried out to described colostrum, and in impouring frozen water, thus obtained Allyl isothiocyanate nano-lipid carrier.
The drug loading and the envelop rate that measure Allyl isothiocyanate nano-lipid carrier are respectively 6.53% and 72.7%
Embodiment three
A kind of Allyl isothiocyanate nano-lipid carrier, it consists of: allyl isosulfocyanate 10mg, GMS60mg, MCT20uL, lecithin 150mg, dehydrated alcohol 5mL, PEG200020mg, Tween8040mg, water for injection 50mL.
Preparation method is as follows:
Allyl isosulfocyanate, GMS, MCT, lecithin are dissolved in dehydrated alcohol, decompression rotary evaporation removing dehydrated alcohol, and are heated to 80 DEG C of meltings to form organic facies; PEG2000, Tween80 are dissolved in water for injection, and are heated to 80 DEG C, to form aqueous phase; At the temperature of 80 DEG C, under agitation by described organic facies and aqueous phase mixing, to prepare colostrum; High pressure homogenize process is carried out to described colostrum, and in impouring frozen water, thus obtained Allyl isothiocyanate nano-lipid carrier.
The drug loading and the envelop rate that measure Allyl isothiocyanate nano-lipid carrier are respectively 9.22% and 90.3%.
The foregoing is only preferred embodiment of the present invention, not in order to limit the present invention, all any amendments done within the spirit and principles in the present invention, equivalent replacement and improvement etc., all should be included within protection scope of the present invention.
Claims (5)
1. the preparation method of Allyl isothiocyanate nano-lipid carrier, is characterized in that, it is grouped into by each one-tenth of following percetage by weight: allyl isosulfocyanate 0.01 ~ 8%; Solid lipid material 0.50 ~ 15%; Fluid oil 0 ~ 15%; Emulsifying agent 0.10 ~ 15%; Long circulating adjuvant 0 ~ 15%; Additives 0 ~ 15%; Surplus is water for injection; This preparation method comprises the following steps:
Allyl isosulfocyanate, Solid lipid material, fluid oil, fat-soluble emulsifier are dissolved in organic solvent, then remove organic solvent, and be heated to 60 ~ 100 DEG C of meltings, to form organic facies;
Long circulating adjuvant, water soluble emulsifier, additives are dissolved in water for injection, and are heated to 60 ~ 100 DEG C, to form aqueous phase;
At 60 ~ 100 DEG C of temperature, by described organic facies and aqueous phase mixing under stirring or shear conditions, to prepare colostrum;
Ultrasonic or high pressure homogenize process is carried out to described colostrum, and in impouring frozen water, thus obtained Allyl isothiocyanate nano-lipid carrier.
2. the preparation method of Allyl isothiocyanate nano-lipid carrier, is characterized in that, it is grouped into by each one-tenth of following percetage by weight: allyl isosulfocyanate 0.01 ~ 8%; Solid lipid material 0.50 ~ 15%; Fluid oil 0 ~ 15%; Emulsifying agent 0.10 ~ 15%; Long circulating adjuvant 0 ~ 15%; Additives 0 ~ 15%; Surplus is water for injection; This preparation method comprises the following steps:
Allyl isosulfocyanate, Solid lipid material, fluid oil, fat-soluble emulsifier are dissolved in organic solvent, then remove organic solvent, and be heated to 60 ~ 100 DEG C of meltings, to form organic facies;
Long circulating adjuvant, water soluble emulsifier, additives are dissolved in water for injection, and are heated to 60 ~ 100 DEG C, to form aqueous phase;
At the temperature of 0 ~ 100 DEG C, by described organic facies and aqueous phase mixing under stirring or shear conditions, prepare colostrum, carry out ultrasonic or high pressure homogenize process by described, adopt reduction vaporization or vacuum drying method removing organic solvent again, obtain Allyl isothiocyanate nano-lipid carrier.
3. the preparation method of Allyl isothiocyanate nano-lipid carrier according to claim 1 and 2, is characterized in that: described organic solvent is selected from dichloromethane, chloroform, acetone, methanol, ethanol, ether, oxolane or isopropyl alcohol and combination in any thereof.
4. the preparation method of Allyl isothiocyanate nano-lipid carrier according to claim 1 and 2, is characterized in that: add freeze drying protectant further to make lyophilized formulations to described obtained Allyl isothiocyanate nano-lipid carrier.
5. the preparation method of Allyl isothiocyanate nano-lipid carrier according to claim 4, is characterized in that: described freeze drying protectant is selected from trehalose, sucrose, mannitol, glucose, sodium chloride, lactose, sorbose, dextran, glycerol or glycine and combination in any thereof.
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| CN103446076A (en) * | 2013-09-16 | 2013-12-18 | 上海海虹实业(集团)巢湖今辰药业有限公司 | Allyl isothiocyanate solid lipid nanoparticle and preparation method thereof |
| CN106333353A (en) * | 2016-08-25 | 2017-01-18 | 江南大学 | High-stability mustard oil nanometer emulsion and preparation method thereof |
| CN111568892A (en) * | 2020-05-26 | 2020-08-25 | 中南大学湘雅二医院 | Use of AITC |
| CN114916651B (en) * | 2022-05-19 | 2024-03-29 | 成都科建生物医药有限公司 | Mustard essential oil liposome and preparation method and application thereof |
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