CN103505419A - Oxygen-carrying lipidosome with low surface tension and preparation method thereof - Google Patents
Oxygen-carrying lipidosome with low surface tension and preparation method thereof Download PDFInfo
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Abstract
The invention relates to a method for preparing an oxygen-carrying lipidosome with low surface tension. The method comprises the following steps: dissolving phospholipid, cholesterol, tyloxapol, hexadecyl alcohol and palmitic acid in an organic solvent, and ultrasonically and uniformly mixing; adding fluorocarbon into a solution, and continuously performing ultrasonic and uniform mixing; slowly dripping the obtained mixed solution into a saline solution, stirring the solution, stirring until the organic solvent is completely volatilized, and obtaining the oxygen-carrying lipidosome coated with the fluorocarbon. The prepared oxygen-carrying lipidosome has relatively low surface tension and is convenient for spreading during pulmonary drug delivery, and a contact area is increased. The oxygen-carrying lipidosome can be applied to aspects of emergency oxygen supply drugs, acute blood supply and the like.
Description
Technical field
The invention belongs to the preparation field of nano material, relate to a kind of water-soluble nano level oxygen carrier liposome and technology of preparing thereof.
Technical background
Perfluorocarbon compound is the resulting compound of hydrogen atom in a class fluorine atom substituted hydrocarbons, under room temperature, be generally colourless transparent liquid, density is high, and stable in properties is difficult for occurring metabolism and decomposes, having the function that fully carries oxygen and carbon dioxide, is desirable liquid breathing medium.Adopting approach in lung, can be acute respiratory distress disease, and the situations such as accident provide treatment.
Adopt direct liquid ventilation method, directly to the fluorocarbons that injects oxygenate in lung, carry out gas exchange, although can improve respiratory distress syndrome (ivrds) patient's lung compliance and oxygenate situation, but easily cause extra injury of lung, clinically application difficult (J. Pediatr., 1990,117:106., Am. J. Pespir. Crit. Care. Med., 2002,165:781).Adopt to suck ventilation, not only can improve lung compliance and oxygenate situation, also can alleviate pneumonia reaction (PLA's medical journal, 2009,34:746.), there is potential researching value.The relevant report of the method is less, and it still needs further research for clinical.
At present, the perfluorocarbon compound of liposome has obtained certain research, but still a kind of clinical required oxygen carrier liposome that meets can not be provided.Adopt injection method can prepare the fluorine carbon liposome compared with small particle diameter, but only adopt phospholipid as becoming film base material, the liposome solutions of acquisition has relatively high surface tension, is difficult to sprawl on alveolar surface, thereby has limited its application.In the one-tenth film base material of phospholipid, add and can reduce capillary alevaire, hexadecanol, Palmic acid, has reduced the surface tension of fluorine carbon liposome, has better improved spreadability, increased gas exchange area, thereby the efficiency of gas exchange is enhanced.
Summary of the invention
In order to overcome the deficiencies in the prior art, the invention provides oxygen carrier liposome of a kind of low surface tension and preparation method thereof.
A kind of oxygen carrier liposome of low surface tension, it is characterized in that, in every 100 milliliters of liposome solutions, contain 0.1-50 gram of fluorocarbons, 1-50 gram of phospholipid, the cholesterol of 1-10 gram, the alevaire of 0-5 gram, the hexadecanol of 0-5 gram, the Palmic acid of 0-5 gram, surplus is water water, the liposome mean diameter in described solution is in 30-150 nanometer.
The preparation method of oxygen carrier liposome, it is characterized in that, comprise the following steps:
(1) meter by weight, by the Palmic acid of the hexadecanol of the alevaire of the cholesterol of 1-500 part phospholipid, 1-50 part, 0-20 part, 0-20 part, 0-20 part, is dissolved in the organic solvent of 1000 parts ultrasonic mix homogeneously;
(2) in being dissolved with the organic solvent of phospholipid, add fluorocarbons 10-500 part, continue ultrasonic mix homogeneously;
(3) the resulting solution of step (2) is slowly dropped in the saline solution of 1000-5000 part, agitating solution, mixing speed is 500-2500 rev/min, is stirred to organic solvent volatilization completely, approximately 2 hours time, can obtain wrapping up the oxygen carrier liposome of fluorocarbons.
By phospholipid, cholesterol, alevaire, hexadecanol, Palmic acid, is dissolved in organic solvent, adds fluorocarbons to make its mix homogeneously, the mixed solution of gained joins in saline solution, stirs and makes organic solvent volatilization completely, can obtain wrapping up the oxygen carrier liposome of fluorocarbons.
Described organic solvent is petroleum ether, chloroform, dichloromethane, ether, normal hexane, ethyl acetate, methanol, a kind of or its combination in toluene.
Described phospholipid is soybean lecithin, Ovum Gallus domesticus Flavus lecithin, hydrolecithin, HSPC, hydrogenation Yolk lecithin, DLPC, two nutmeg phosphatidyl cholines, dipalmitoyl phosphatidyl choline, distearoyl phosphatidylcholine, 1-nutmeg acyl-2-palmitoylphosphatidyl choline, 1-palmityl-2-DSPC, 1-stearoyl-2-palmitoylphosphatidyl choline, POPC, the sub-oleoyl phosphatidylcholine of 1-stearoyl-2-, DOPC, hydrogenation dipalmitoyl phosphatidyl choline, distearoyl phosphatidylcholine, two nutmeg acyl phosphatidic acid, two nutmeg acyl phosphatidic acid, DPPA, DPPA, G 12S3P, two lima bean lotus acyl phosphatidyl ethylene glycol amine, two palmityl phospholipid indulge in ethylene glycol amine, cephalin acyl serine, two nutmeg acyl Phosphatidylserine, two palmityl Phosphatidylserine, E-PG, PE, two nutmeg acyl phosphatidyl glycerols, DPPG, DSPG, DOPG, brain sphingomyelins, a kind of or its combination in two palmityl sphingomyelins or distearyl sphingomyelins.
Described saline solution is normal saline, phosphate buffer, acetate buffer, Basionic buffer, barbitol buffer solution, sodium formate buffer, citrate buffer, ammonia-ammonium chloride buffer, Borax-calcium chloride buffer, acetic acid-lithium salts buffer, acetic acid-sodium-acetate buffer, acetic acid-potassium acetate buffer, acetic acid-ammonium acetate buffer, a kind of in phosphoric acid-triethylamine buffer solution.
Described fluorocarbons is two (F-alkyl) ethylene, is specially two (F-butyl) ethylene, two (F-hexyl) ethylene; F-naphthalane; F-amantadine (FA); F-methyl amantadine (FMA); F-1,3-dimethyl amantadine (FDMA); Perfluoro-2,2,4,4-tetramethylpentane; F-bis-or F-trimethyl bicyclo-[3,3,1] nonane; The fluoridized amine of C7-12, is specially F-tripropyl amine (TPA), F-4-methyl octahydro quinolizine (FMOQ), F-n-methyl-Decahydroisoquinolinpreparation (FMIQ), F-n-methyl decahydroquinoline (FHQ), F-n-cyclohexyl pyrrolidine (FCHP); Bromination perfluorocarbon compound, is specially perfluoro bromide octane (C
8f
17br), 1-bromine 15 fluorine heptane (C
7f
15br), 1-bromine 13 fluorine hexane (C
6f
13br), a kind of or its combination in.
The object of the present invention is to provide a kind of preparation method of oxygen carrier liposome of low surface tension, prepared this oxygen carrier liposome encapsulation is high, and particle diameter is little, surface tension is low, and toxicity is little, is suitable as pulmonary's oxygen supply and uses, and method is easy, be convenient to large-scale production.
The invention has the advantages that:
(1) the oxygen carrier liposome that prepared by the present invention, surface tension is low, can better be sprawled on lung surface, thereby realize pulmonary's oxygen supply.
(2) adopting fluorocarbons is dissolved oxygen material, and oxygen content is high, can realize rapidly gas exchange.
Accompanying drawing explanation
The transmission electron microscope picture of oxygen carrier liposome in Fig. 1 embodiment 1.
The Cytotoxic evaluation of oxygen carrier liposome in Fig. 2 embodiment 3.
The Cytotoxic evaluation of oxygen carrier liposome in Fig. 3 embodiment 3.
Left: not have the cell in the phosphate buffered solution of oxygen carrier liposome; Right: the cell in the phosphate buffer that contains oxygen carrier liposome.
The specific embodiment
By specific embodiment, technical scheme of the present invention is further described below.Following embodiment further illustrates of the present invention, and is not limited to scope of the present invention.
Embodiment 1: the preparation of oxygen carrier liposome.
By weight, formula is as follows:
2000 parts of normal saline;
200 parts of soybean lecithins;
200 parts of perfluoro bromide octanes; ;
1000 parts of dichloromethane;
5 parts of Palmic acids;
2 parts of alevaires.
Preparation technology:
(1) meter by weight, by 200 parts of soybean lecithins, 5 parts of Palmic acids, 2 parts of alevaires are dissolved in the ether of 2000 parts, ultrasonic mix homogeneously;
(2) in diethyl ether solution, add 200 parts of perfluoro bromide octanes, continue ultrasonic mix homogeneously;
(3) the resulting solution of step (2) is slowly dropped in the normal saline of 2000 parts, agitating solution (mixing speed is 1000 revs/min), is stirred to ether volatilization completely, approximately 2 hours time.Can obtain wrapping up the oxygen carrier liposome of perfluoro bromide octane.This oxygen carrier Liposomal formulation is milky white solution, dilutes 10 times and can obtain light white with the clear solution of blue-opalescent.The surface tension of said preparation is that 29 mN/m liposome sizes distribute (its transmission electron microscope picture as shown in Figure 1) in the scope of 40 100 nm, and the envelop rate of perfluoro bromide octane is about 95 %.
Embodiment 2: the preparation of oxygen carrier liposome.
By weight, formula is as follows:
2000 parts of phosphate buffers;
200 parts of Ovum Gallus domesticus Flavus lecithins;
The mixture of FC-77(PFO and perfluor ring octyl ether) 200 parts;
1000 parts of ether;
1 part of hexadecanol;
1 part of alevaire.
Preparation technology:
(1) meter by weight, by 200 parts of soybean lecithins, 2 parts of hexadecanols, 1 part of alevaire is dissolved in the ether of 1000 parts, ultrasonic mix homogeneously;
(2) in diethyl ether solution, add the mixture of FC-77(PFO and perfluor ring octyl ether) 200 parts, continue ultrasonic mix homogeneously;
(3) the resulting solution of step (2) is slowly dropped in the normal saline of 2000 parts, agitating solution (mixing speed is 1000 revs/min), is stirred to ether volatilization completely, approximately 2 hours time.Can obtain wrapping up the oxygen carrier liposome of perfluoro bromide octane.This oxygen carrier Liposomal formulation is milky white solution, dilutes 10 times and can obtain light white with the clear solution of blue-opalescent.The surface tension of said preparation is that 33 mN/m liposome sizes distribute in the scope of 50 90 nm, and the envelop rate of FC-77 is about 80 %.
Embodiment 3 oxygen carrier liposome toxicity assessments.
The take the logarithm monolayer culture HEK293 epithelial cell of trophophase, with 0.25% membrane proteolytic enzyme and 0.025% disodium EDTA solution digestion single-layer culturing cell, is made into single cell suspension ，Yi Mei hole 1 * 10 with the DMEM cell culture medium containing 10% hyclone
4individual cell is inoculated in 96 orifice plates, and every pore volume 100 microlitres, move into culture plate in CO2 gas incubator, and at 37 ℃, overnight incubation under 5% carbon dioxide and saturated humidity condition, makes cell attachment.Next day, with the fluorine carbon oxygen carrier liposome solutions (adopting the prepared oxygen carrier liposome of embodiment 2) of a series of variable concentrations of phosphate-containing solution preparation.Culture fluid sucking-off by culture dish, adds oxygen carrier liposome solutions, hatches different time for 37 ℃, inhales and abandons supernatant.With phosphate solution, washing twice ，Mei hole, to add 100 microlitre concentration be the tetrazolium bromide solution of 5 mg/ml, continues to cultivate 4 hours.The sodium dodecyl sulfate solution that adds 100 microlitres 10%, cultivates after 4 hours and adopts microplate reader to test, and absorbing wavelength adopts 570 nm.Result as shown in Figure 2.Can find out, under liposome existence condition, cultivating 4 hours, there is not obvious activity decreased in cell, shows that this oxygen carrier liposome does not have toxicity substantially to epithelial cell.
The take the logarithm monolayer culture HEK293 epithelial cell of trophophase, with 0.25% membrane proteolytic enzyme and 0.025% disodium EDTA solution digestion single-layer culturing cell, is made into single cell suspension ，Yi Mei hole 1 * 10 with the DMEM cell culture medium containing 10% hyclone
5individual cell is inoculated in Tissue Culture Dish, and 1 milliliter of every pore volume, moves into culture dish in CO2 gas incubator, and at 37 ℃, overnight incubation under 5% carbon dioxide and saturated humidity condition, makes cell attachment.Next day, the phosphate solution (adopting the prepared oxygen carrier liposome of embodiment 2) of preparation fluorine carbon oxygen carrier liposome.In content of phospholipid, the concentration of liposome solutions is 20 mg/ml.Culture fluid sucking-off by culture dish, adds oxygen carrier liposome solutions, hatches 4 hours for 37 ℃, inhales and abandons supernatant.With phosphate solution, wash 3 times, be placed under fluorescence microscope light field and observe, and take pictures.Picture as shown in Figure 3.As can be seen from the figure, adopt the aquicultural cell contain oxygen carrier liposome, and not containing the phosphate solution cultured cells of oxygen carrier liposome, on quantity and pattern, there is no notable difference, show that this oxygen carrier liposome does not have toxicity substantially to epithelial cell.
Claims (7)
1. the oxygen carrier liposome of a low surface tension, it is characterized in that, in every 100 milliliters of liposome solutions, contain 0.1-50 gram of fluorocarbons, 1-50 gram of phospholipid, the cholesterol of 1-10 gram, the alevaire of 0-5 gram, the hexadecanol of 0-5 gram, the Palmic acid of 0-5 gram, surplus is water water, the liposome mean diameter in described solution is in 30-150 nanometer.
2. a kind of preparation method of oxygen carrier liposome of low surface tension according to claim 1, is characterized in that, comprises the following steps:
(1) meter by weight, by the Palmic acid of the hexadecanol of the alevaire of the cholesterol of 1-500 part phospholipid, 1-50 part, 0-20 part, 0-20 part, 0-20 part, is dissolved in the organic solvent of 1000 parts ultrasonic mix homogeneously;
(2) in being dissolved with the organic solvent of phospholipid, add fluorocarbons 10-500 part, continue ultrasonic mix homogeneously;
(3) the resulting solution of step (2) is slowly dropped in the saline solution of 1000-5000 part, agitating solution, mixing speed is 500-2500 rev/min, is stirred to organic solvent volatilization completely, approximately 2 hours time, can obtain wrapping up the oxygen carrier liposome of fluorocarbons.
3. by phospholipid, cholesterol, alevaire, hexadecanol, Palmic acid, is dissolved in organic solvent, adds fluorocarbons to make its mix homogeneously, the mixed solution of gained joins in saline solution, stirs and makes organic solvent volatilization completely, can obtain wrapping up the oxygen carrier liposome of fluorocarbons.
4. a kind of preparation method of oxygen carrier liposome of low surface tension according to claim 2, is characterized in that, described organic solvent is petroleum ether, chloroform, dichloromethane, ether, normal hexane, ethyl acetate, methanol, a kind of or its combination in toluene.
5. a kind of preparation method of oxygen carrier liposome of low surface tension according to claim 2, is characterized in that, described phospholipid is soybean lecithin, Ovum Gallus domesticus Flavus lecithin, hydrolecithin, HSPC, hydrogenation Yolk lecithin, DLPC, two nutmeg phosphatidyl cholines, dipalmitoyl phosphatidyl choline, distearoyl phosphatidylcholine, 1-nutmeg acyl-2-palmitoylphosphatidyl choline, 1-palmityl-2-DSPC, 1-stearoyl-2-palmitoylphosphatidyl choline, POPC, the sub-oleoyl phosphatidylcholine of 1-stearoyl-2-, DOPC, hydrogenation dipalmitoyl phosphatidyl choline, distearoyl phosphatidylcholine, two nutmeg acyl phosphatidic acid, two nutmeg acyl phosphatidic acid, DPPA, DPPA, G 12S3P, two lima bean lotus acyl phosphatidyl ethylene glycol amine, two palmityl phospholipid indulge in ethylene glycol amine, cephalin acyl serine, two nutmeg acyl Phosphatidylserine, two palmityl Phosphatidylserine, E-PG, PE, two nutmeg acyl phosphatidyl glycerols, DPPG, DSPG, DOPG, brain sphingomyelins, a kind of or its combination in two palmityl sphingomyelins or distearyl sphingomyelins.
6. a kind of preparation method of oxygen carrier liposome of low surface tension according to claim 2, it is characterized in that, described saline solution is normal saline, phosphate buffer, acetate buffer, Basionic buffer, barbitol buffer solution, sodium formate buffer, citrate buffer, ammonia-ammonium chloride buffer, Borax-calcium chloride buffer, acetic acid-lithium salts buffer, acetic acid-sodium-acetate buffer, acetic acid-potassium acetate buffer, acetic acid-ammonium acetate buffer, a kind of in phosphoric acid-triethylamine buffer solution.
7. a kind of preparation method of oxygen carrier liposome of low surface tension according to claim 2, is characterized in that, described fluorocarbons is two (F-alkyl) ethylene, is specially two (F-butyl) ethylene, two (F-hexyl) ethylene; F-naphthalane; F-amantadine (FA); F-methyl amantadine (FMA); F-1,3-dimethyl amantadine (FDMA); Perfluoro-2,2,4,4-tetramethylpentane; F-bis-or F-trimethyl bicyclo-[3,3,1] nonane; The fluoridized amine of C7-12, is specially F-tripropyl amine (TPA), F-4-methyl octahydro quinolizine (FMOQ), F-n-methyl-Decahydroisoquinolinpreparation (FMIQ), F-n-methyl decahydroquinoline (FHQ), F-n-cyclohexyl pyrrolidine (FCHP); Bromination perfluorocarbon compound, is specially perfluoro bromide octane (C
8f
17br), 1-bromine 15 fluorine heptane (C
7f
15br), 1-bromine 13 fluorine hexane (C
6f
13br), a kind of or its combination in.
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Cited By (8)
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| WO2016019627A1 (en) * | 2014-08-08 | 2016-02-11 | Shenzhen Hightide Biopharmaceutical, Ltd. | Liquid formulation compositions, medicament delivery devices, and methods of preparation and use thereof |
| CN105362220A (en) * | 2014-08-08 | 2016-03-02 | 深圳君圣泰生物技术有限公司 | Preparation, preparation method and uses thereof |
| CN105435227A (en) * | 2014-08-08 | 2016-03-30 | 深圳君圣泰生物技术有限公司 | Liquid preparation composition and preparation method and use and solid preparation thereof |
| CN105434346A (en) * | 2014-08-08 | 2016-03-30 | 深圳君圣泰生物技术有限公司 | Preparation composition and preparation method and use thereof |
| CN105435344A (en) * | 2015-12-15 | 2016-03-30 | 上海纳米技术及应用国家工程研究中心有限公司 | Portable efficient oxygen supply spraying device for lung |
| CN106361701A (en) * | 2016-08-31 | 2017-02-01 | 上海交通大学 | Liposome drug carrier and preparation method and application thereof |
| CN110585135A (en) * | 2019-01-28 | 2019-12-20 | 玉林师范学院 | Preparation method of oxygen-producing nano liposome |
| CN113801344A (en) * | 2021-09-15 | 2021-12-17 | 复旦大学 | Oxygen-loaded fluorine-containing temperature-sensitive hydrogel and preparation method and application thereof |
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| WO2016019627A1 (en) * | 2014-08-08 | 2016-02-11 | Shenzhen Hightide Biopharmaceutical, Ltd. | Liquid formulation compositions, medicament delivery devices, and methods of preparation and use thereof |
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| CN113801344A (en) * | 2021-09-15 | 2021-12-17 | 复旦大学 | Oxygen-loaded fluorine-containing temperature-sensitive hydrogel and preparation method and application thereof |
| CN113801344B (en) * | 2021-09-15 | 2022-08-12 | 复旦大学 | Oxygen-loaded fluorine-containing temperature-sensitive hydrogel and preparation method and application thereof |
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