CN102973518A - Perfluorocarbon compound lipidosome nanosphere and preparation method thereof - Google Patents
Perfluorocarbon compound lipidosome nanosphere and preparation method thereof Download PDFInfo
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- CN102973518A CN102973518A CN2012105492520A CN201210549252A CN102973518A CN 102973518 A CN102973518 A CN 102973518A CN 2012105492520 A CN2012105492520 A CN 2012105492520A CN 201210549252 A CN201210549252 A CN 201210549252A CN 102973518 A CN102973518 A CN 102973518A
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Abstract
The invention relates to a perfluorocarbon compound lipidosome nanosphere and a preparation method of the perfluorocarbon compound lipidosome nanosphere. The perfluorocarbon compound lipidosome nanosphere is characterized in that the average grain diameter of the perfluorocarbon compound lipidosome nanosphere is 100-150 nanometers and is a nanosphere with a structure formed by covering inner-layer perfluorbromooctane by an outer-layer polylactic acid-glycolic acid copolymer; and the encapsulation efficiency of the outer-layer polylactic acid-glycolic acid copolymer to the inner-layer perfluorbromooctane in the nanosphere is more than 80%. The invention further relates to a preparation method of the perfluorocarbon compound nanosphere. According to the perfluorocarbon compound nanosphere disclosed by the invention, the covering layer of the outer layer is the polylactic acid-glycolic acid copolymer with good biocompatibility and can be degraded into lactic acid and glycolic acid in vivo; and the two products are byproducts of a human metabolic pathway so that no toxic side effects on a human body are caused. According to the perfluorocarbon compound nanosphere, the inner layer is the perfluorbromooctane and can be used as ultrasonic diagnosis reagents and blood substitutes. A preparation process of the perfluorocarbon compound nanosphere disclosed by the invention is simple to operate and feasible, and can carry out continuous product.
Description
Technical field
The present invention relates to a kind of nanosphere and preparation method thereof, be specially a kind of perfluorocarbon compound and receive liposome rice ball and preparation method thereof.
Background technology
Perfluorocarbon compound is a class ring-type or the straight chain shape organic compound that form after the hydrogen atom in the Hydrocarbon is all replaced by fluorine atom and since carbon atom and fluorine atom pretend and exert oneself, fluorocarbons has extraordinary stability.Perfluorocarbon compound is water insoluble, and the function of good dissolving non-polar gas is arranged, and can be used as the carrier of oxygen and carbon dioxide.Fluorocarbons dissolved oxygen ability on the biomedical applications is 35-44mmolL-1, the dissolved carbon dioxide ability is 200mmolL-1, because its ability that has good dissolving or discharge oxygen, fluorocarbons have been employed with the partial liquid ventilation take the fluorine carbon solution as the gas exchange medium and have treated neonate acute respiratory distress syndrome and blood substitute.The fluorocarbons of using in the organism requires its particle diameter to be about 200 nanometers or less, this is because the larger fluorocarbons of particle diameter can not be even with aqueous solution in the body, can not be stable be suspended in the solution, and the solution that the fluorocarbon nano ball is made, the fluorocarbons oxygen exchange area that disperses is very large, more can play the oxygen effect of taking.Perfluoro bromide octane is the chain fluorocarbons that end has a bromine atoms.The preparation method that Granted publication number has been invented the fluorocarbon nanometer medicine-carrying preparation take block copolymer as carrier for the patent of invention of CN 10200871 B, the perfluorocarbon compound that the method adopts is FC77.Compare with FC77, the perfluoro bromide octane boiling point is higher, can effectively prevent the perfluorocarbon compound volatilization causes in the preparation process waste of raw materials problem and the lower problem of envelop rate.
Poly(D,L-lactide-co-glycolide (poly (lactic-co-glycolic acid), PLGA) be polymerized at random by lactic acid and hydroxyacetic acid, it is a kind of degradable functional polymer organic compound, catabolite is lactic acid and hydroxyacetic acid, the by-product of people's metabolic pathway, therefore can toxic side effect to organism.Poly(D,L-lactide-co-glycolide authenticates by FDA in the U.S., is formally included into American Pharmacopeia as pharmaceutic adjuvant.Poly(D,L-lactide-co-glycolide has good encystation and the performance of film forming, is widely used in pharmacy, medical engineering material and modernized industrial field, as: skin transplantation, wound suture, body is implanted into, the micro-nano grain of rice, pharmaceutical carrier etc.
Utilize Poly(D,L-lactide-co-glycolide that perfluoro bromide octane is wrapped up the nanosphere that is prepared into, not only can be used as contrast agent and carry out ultra sonic imaging, can also carry out as artificial blood the treatment of clinical anoxia symptom.
Summary of the invention
In order to overcome the defective of prior art, the invention provides a kind of perfluorocarbon compound liposome nanosphere and preparation method thereof,
A kind of perfluorocarbon compound liposome nanosphere is characterized in that the mean diameter of described perfluorocarbon compound liposome nanosphere is the 100-500 nanometer, and structure is the nanosphere that outer Poly(D,L-lactide-co-glycolide wrapping inner layer perfluoro bromide octane forms; Described nanosphere ectomesoderm Poly(D,L-lactide-co-glycolide is more than 80% to the envelop rate of internal layer perfluoro bromide octane.
A kind of preparation method of perfluorocarbon compound liposome nanosphere is characterized in that, comprises the steps:
(1) get Poly(D,L-lactide-co-glycolide 0.01-1 gram, perfluoro bromide octane 10-100 μ L fully is dissolved in the organic solvent 2-6 milliliter, obtains solution A; Wherein, perfluoro bromide octane and Poly(D,L-lactide-co-glycolide mass ratio are 0.1-1; The volume ratio of perfluoro bromide octane and organic solvent is 0.01
-0.1;
(2) A solution is mixed with surfactant solution 5-100 milliliter, wherein the concentration of surfactant is 1%-4%(w/v in the surfactant solution), A solution and surfactant solution volume ratio are 0.05-0.5; Ultra-sonic dispersion 1-10 minute, wherein ultrasonic power was 50W-300W, magnetic agitation 3-12 hour, obtains solution B;
(3) purification mode: with the solution B bag filter of packing into, with deionized water dialysis 3-5 days, then with the sample lyophilizing, obtain perfluorocarbon compound liposome nanosphere.
Described surfactant is a kind of in sodium cholate, the NaTDC.
Described organic solvent is a kind of in dichloromethane, the chloroform.
Described Poly(D,L-lactide-co-glycolide molecular weight is 150,000, and the ratio of polylactic acid and hydroxyacetic acid is 75:25.
The particle diameter of described perfluorocarbon compound liposome nanosphere was controlled by supersound process time and power.
The outer layer thickness of described perfluorocarbon compound liposome nanosphere is controlled with the ratio of Poly(D,L-lactide-co-glycolide by regulating perfluoro bromide octane, and when perfluoro bromide octane: during the increase of Poly(D,L-lactide-co-glycolide ratio, outer layer thickness diminishes.
Prepared perfluorocarbon compound liposome nanosphere can solve size problem and the envelop rate problem of existing fluorocarbons, utilize Poly(D,L-lactide-co-glycolide to carry out the skin parcel with crossing, and can improve greatly its bioavailability and safety in vivo.
Entrapment efficiency determination: utilize the UV, visible light spectrophotometric spectra to measure, adopt the multicomponent computational methods, specific as follows
In the formula
,
With
Be respectively sample at λ
1, λ
2, λ
3The ultraviolet absorption value at place, C
x, C
y, C
zBe respectively the concentration of x component, y component and z component;
,
With
Respectively that x component, y component and z component are in wavelength X
1The molar absorption coefficient at place;
,
With
Respectively that x component, y component and z component are in wavelength X
2The molar absorption coefficient at place;
,
With
Respectively that x component, y component and z component are in wavelength X
3The molar absorption coefficient at place;
,
With
,
With
,
With
Can use the standard solution of x, y and z respectively at λ
1, λ
2, λ
3Calculate behind place's mensuration absorbance and try to achieve.Will
,
With
,
With
,
With
The substitution equation group can get the concentration C of three components
x, C
y, C
Z.λ wherein
1, λ
2, λ
3The place is respectively 217nm, 250nm and 280nm.
The envelop rate computing formula is: envelop rate=purification is the front perfluoro bromide octane concentration of perfluoro bromide octane concentration ÷ purification * 100% afterwards, utilizes the envelop rate of multicomponent determination of uv absorption perfluoro bromide octane.In entrapment efficiency determination, perfluorocarbon compound liposome nanosphere is used with the deionized water of front solution with volume of not purifying and is disperseed.
Advantage of the present invention is: the method adopt biocompatibility preferably Poly(D,L-lactide-co-glycolide as outer lapping, this material can degradation in vivo become lactic acid and hydroxyacetic acid, these two kinds of by-products that product is people's metabolic pathway, therefore can not produce toxic and side effects to human body, greatly improve clinical value; The envelop rate of the nanosphere that the method obtains is 80%, and particle diameter is at 100-500nm, and the long preservation stability inferior is better, and this method technique is very simple, and is easy to operate, can produce continuously.
Description of drawings
Fig. 1 is the hydration particle size distribution figure of the perfluorocarbon compound nanosphere of embodiment 1.
Can know on scheme and find out that perfluorocarbon compound nanosphere average particle diameter is about 120 nanometers.
Fig. 2 is the hydration particle size distribution figure of the perfluorocarbon compound nanosphere of embodiment 2.
Can know on scheme and find out that perfluorocarbon compound nanosphere average particle diameter is about 224 nanometers.
Fig. 3 is the hydration particle size distribution figure of the perfluorocarbon compound nanosphere of embodiment 3.
Can know on scheme and find out that perfluorocarbon compound nanosphere average particle diameter is about 400 nanometers.
Fig. 4 is the scanning electron microscope (SEM) photograph of the perfluorocarbon compound nanosphere of embodiment 4.
Can know on scheme and find out that the perfluorocarbon compound nano-particle is spherical, be nucleocapsid structure, wherein stratum nucleare is thicker, and shell is very thin, and perfluorocarbon compound nanosphere particle diameter is about 500 nanometers.
Fig. 5 is the scanning electron microscope (SEM) photograph of the perfluorocarbon compound nanosphere of embodiment 2.
Can know on scheme and find out that the perfluorocarbon compound nano-particle is spherical, be nucleocapsid structure, wherein stratum nucleare is thicker, and shell is thinner, and perfluorocarbon compound nanosphere particle diameter is about 200 nanometers.
Fig. 6 is the scanning electron microscope (SEM) photograph of the perfluorocarbon compound nanosphere of embodiment 5.
Can know on scheme and find out that the perfluorocarbon compound nano-particle is spherical, be nucleocapsid structure, wherein stratum nucleare is thicker, and shell is relatively thick, and perfluorocarbon compound nanosphere particle diameter is about 200 nanometers.
Specific implementation method
Embodiment 1:
A, get Poly(D,L-lactide-co-glycolide 0.1g, perfluoro bromide octane 60 μ L fully are dissolved in the 4mL dichloromethane, obtain solution A;
B, add 1.5% deoxycholic acid sodium solution 20ml in the solution A, ultra-sonic dispersion 7min, ultrasonic power are 200W, and magnetic agitation 4 hours obtains solution B;
C, purification mode: with the solution B bag filter of packing into, with deionized water dialysis 5 days, then with the sample lyophilizing, obtain final products.
Embodiment 2:
A. get Poly(D,L-lactide-co-glycolide 0.1g, perfluoro bromide octane 60 μ L fully are dissolved in the 4mL dichloromethane, obtain solution A;
B. in solution A, add 1.5% deoxycholic acid sodium solution 20ml, ultra-sonic dispersion 5min, ultrasonic power control 200W, magnetic agitation 4 hours obtains solution B;
C. the mode of purifying: with the solution B bag filter of packing into, with deionized water dialysis 5 days, then with the sample lyophilizing, obtain final products.
Embodiment 3:
A. get Poly(D,L-lactide-co-glycolide 0.1g, perfluoro bromide octane 60 μ L fully are dissolved in the 4mL dichloromethane, obtain solution A;
B. add 1.5% deoxycholic acid sodium solution 20ml in solution A, ultra-sonic dispersion 2 min, ultrasonic power are 120W, and magnetic agitation 4 hours obtains solution B;
C. the mode of purifying: with the solution B bag filter of packing into, with deionized water dialysis 5 days, then with the sample lyophilizing, obtain final products.
A. get Poly(D,L-lactide-co-glycolide 0.1g, perfluoro bromide octane 100 μ L fully are dissolved in the 6mL dichloromethane, obtain solution A;
B. add 1.5% deoxycholic acid sodium solution 20ml in solution A, ultra-sonic dispersion 2min, ultrasonic power are 120W, and magnetic agitation 4 hours obtains solution B;
C. the mode of purifying: with the solution B bag filter of packing into, with deionized water dialysis 5 days, then with the sample lyophilizing, obtain final products.
Embodiment 5:
A. get Poly(D,L-lactide-co-glycolide 0.5g, perfluoro bromide octane 60 μ L fully are dissolved in the 4mL chloroform, obtain solution A;
B. add 1.5% deoxycholic acid sodium solution 20ml in solution A, ultra-sonic dispersion 5min, ultrasonic power are 200W, and magnetic agitation 4 hours obtains solution B;
C. the mode of purifying: with the solution B bag filter of packing into, with deionized water dialysis 5 days, then with the sample lyophilizing, obtain final products.
Each reaction condition of table one is on the envelop rate impact of perfluoro bromide octane in perfluoro bromide octane-Poly(D,L-lactide-co-glycolide nanosphere
The Poly(D,L-lactide-co-glycolide consumption | The perfluoro bromide octane consumption | Solvent load | Dosage of surfactant | Ultrasonic time | Ultrasonic power | Envelop rate |
0.1g | 60μL | The 4mL dichloromethane | 1.5% deoxycholic acid sodium solution 20ml | 7min | 200W | 84% |
0.1g | 60μL | The 4mL dichloromethane | 1.5% deoxycholic acid sodium solution 20ml | 5min | 200W | 87% |
0.1g | 60μL | The 4mL dichloromethane | 1.5% deoxycholic acid sodium solution 20ml | 2min | 120W | 87% |
0.1g | 100μL | The 6mL dichloromethane | 1.5% deoxycholic acid sodium solution 20ml | 2min | 120W | 81% |
0.5g | 60μL | The 4mL chloroform | 1.5% deoxycholic acid sodium solution 20ml | 5min | 200W | 89% |
Claims (8)
1. a perfluorocarbon compound liposome nanosphere is characterized in that, the mean diameter of described perfluorocarbon compound liposome nanosphere is the 100-500 nanometer, and structure is the nanosphere that outer Poly(D,L-lactide-co-glycolide wrapping inner layer perfluoro bromide octane forms; Described nanosphere ectomesoderm Poly(D,L-lactide-co-glycolide is more than 80% to the envelop rate of internal layer perfluoro bromide octane.
2. the preparation method of described a kind of perfluorocarbon compound liposome nanosphere according to claim 1 is characterized in that, comprises the steps:
(1) get Poly(D,L-lactide-co-glycolide 0.01-1 gram, perfluoro bromide octane 10-100 μ L fully is dissolved in the organic solvent 2-6 milliliter, obtains solution A; Wherein, perfluoro bromide octane and Poly(D,L-lactide-co-glycolide mass ratio are 0.1-1; The volume ratio of perfluoro bromide octane and organic solvent is 0.01
-0.1;
(2) A solution is mixed with surfactant solution 5-100 milliliter, wherein the concentration of surfactant is 1%-4%(w/v in the surfactant solution), A solution and surfactant solution volume ratio are 0.05-0.5; Ultra-sonic dispersion 1-10 minute, wherein ultrasonic power was 50W-300W, magnetic agitation 3-12 hour, obtains solution B;
(3) purification mode: with the solution B bag filter of packing into, with deionized water dialysis 3-5 days, then with the sample lyophilizing, obtain perfluorocarbon compound liposome nanosphere.
3. the preparation method of described a kind of perfluorocarbon compound liposome nanosphere according to claim 2 is characterized in that, described surfactant is a kind of in sodium cholate, the NaTDC.
4. the preparation method of described a kind of perfluorocarbon compound liposome nanosphere according to claim 2 is characterized in that, described organic solvent is a kind of in dichloromethane, the chloroform.
5. the preparation method of described a kind of perfluorocarbon compound liposome nanosphere according to claim 2 is characterized in that described Poly(D,L-lactide-co-glycolide molecular weight is 150,000, and the ratio of polylactic acid and hydroxyacetic acid is 75:25.
6. the preparation method of described a kind of perfluorocarbon compound liposome nanosphere according to claim 2 is characterized in that the particle diameter of described perfluorocarbon compound liposome nanosphere was controlled by supersound process time and power.
7. the preparation method of described a kind of perfluorocarbon compound liposome nanosphere according to claim 2, it is characterized in that, the outer layer thickness of described perfluorocarbon compound liposome nanosphere is controlled by the ratio of regulating perfluoro bromide octane and Poly(D,L-lactide-co-glycolide, when perfluoro bromide octane: when the Poly(D,L-lactide-co-glycolide ratio increased, outer layer thickness diminished.
8. the preparation method of described a kind of perfluorocarbon compound liposome nanosphere according to claim 2 is characterized in that, comprises the steps:
(1) get Poly(D,L-lactide-co-glycolide 0.1 gram, perfluoro bromide octane 60 μ L fully are dissolved in 4 milliliters of dichloromethane, obtain solution A;
(2) in solution A, add 20 milliliters of 1.5% deoxycholic acid sodium solutions, ultra-sonic dispersion 5 minutes, ultrasonic power control 200W, magnetic agitation 4 hours obtains solution B;
(3) purification mode: with the solution B bag filter of packing into, with deionized water dialysis 5 days, then with the sample lyophilizing, obtain final products.
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Cited By (4)
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CN103751106A (en) * | 2013-11-27 | 2014-04-30 | 上海纳米技术及应用国家工程研究中心有限公司 | Water-soluble perfluorooctyl bromide-liposome nanosphere and preparation method thereof |
CN104548148A (en) * | 2014-12-31 | 2015-04-29 | 深圳先进技术研究院 | Poly(lactic-co-glycolic acid) particles for dual imaging, as well as preparation method and application of poly(lactic-co-glycolic acid) particles |
CN107569717A (en) * | 2017-08-07 | 2018-01-12 | 上海纳米技术及应用国家工程研究中心有限公司 | Bone renovating material and its application with tissue oxygen-supplying function |
CN112823783A (en) * | 2019-11-21 | 2021-05-21 | 中国人民解放军军事科学院军事医学研究院 | Bionic erythrocyte formed by coating perfluorocarbon with multi-layer polyelectrolyte microcapsules and preparation method thereof |
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103751106A (en) * | 2013-11-27 | 2014-04-30 | 上海纳米技术及应用国家工程研究中心有限公司 | Water-soluble perfluorooctyl bromide-liposome nanosphere and preparation method thereof |
CN104548148A (en) * | 2014-12-31 | 2015-04-29 | 深圳先进技术研究院 | Poly(lactic-co-glycolic acid) particles for dual imaging, as well as preparation method and application of poly(lactic-co-glycolic acid) particles |
CN104548148B (en) * | 2014-12-31 | 2017-09-22 | 深圳先进技术研究院 | Double imaging PLGA particulates and its preparation method and application |
CN107569717A (en) * | 2017-08-07 | 2018-01-12 | 上海纳米技术及应用国家工程研究中心有限公司 | Bone renovating material and its application with tissue oxygen-supplying function |
CN107569717B (en) * | 2017-08-07 | 2020-09-18 | 上海纳米技术及应用国家工程研究中心有限公司 | Bone repair material with tissue oxygenation function and application thereof |
CN112823783A (en) * | 2019-11-21 | 2021-05-21 | 中国人民解放军军事科学院军事医学研究院 | Bionic erythrocyte formed by coating perfluorocarbon with multi-layer polyelectrolyte microcapsules and preparation method thereof |
CN112823783B (en) * | 2019-11-21 | 2023-04-21 | 中国人民解放军军事科学院军事医学研究院 | Bionic red blood cell formed by wrapping perfluorocarbon with multi-layer polyelectrolyte microcapsule and preparation method thereof |
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