CN107970454A - A kind of preparation method and application of graphene oxide-lipid nanometer composite material - Google Patents
A kind of preparation method and application of graphene oxide-lipid nanometer composite material Download PDFInfo
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- CN107970454A CN107970454A CN201711178589.4A CN201711178589A CN107970454A CN 107970454 A CN107970454 A CN 107970454A CN 201711178589 A CN201711178589 A CN 201711178589A CN 107970454 A CN107970454 A CN 107970454A
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- graphene oxide
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- nanometer composite
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Liposomes
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
Abstract
The invention discloses a kind of preparation method of graphene oxide-lipid nanometer composite material, belong to materials synthesis and biomedicine technical field；Specific method is：Using the graphene oxide of nano-scale as matrix, liposome is synthesized using rotary evaporation, it is then lipid-modified to graphene oxide progress by electrostatic adsorption, so as to obtain the composite material.The lipid-modified nano-carrier that the present invention synthesizes has preferable stability and dispersiveness in physiological conditions；, using the graphene oxide of nano-scale as kernel, outside one layer of liposome of parcel, two kinds of materials are respectively provided with good biocompatibility for it；Antitumor drug adriamycin is supported on graphene oxide, drug loading rate is high, and stability is good, and medicine is had the function that target slow-release, is effectively improved drug effect and reduces the toxic side effect of medicine.
Description
Technical field
The invention belongs to materials synthesis and biomedicine technical field, and in particular to a kind of graphene oxide-lipid nanometer
The preparation method of composite material and its application in terms of antineoplastic drug carrier.
Background technology
Tumour is to seriously endanger one of refractory disease of human health, and the treatment of chemicals seriously makes treatment because of side effect
Result badly.Targeted therapy is carried out to cancer to improve curative effect using pharmaceutical carrier, toxic side effect is reduced, is opened for the treatment of tumour
New thinking is warded off.The species of presently found anti-cancer medicament carrier is varied, including organic material（Such as protein, fat
Class）, inorganic material and high molecular material etc..Since organic material and high molecular material have degradable, medicine as pharmaceutical carrier
Thing easy to leak and it is of high cost the defects of, in order to overcome these defects, present invention employs a kind of inorganic material graphene oxide work
For the carrier of cancer therapy drug, there is stable structure, load drug stabilisation and drugloading rate greatly, are easily prepared, cost is low etc..
In recent years, developing rapidly with nanosecond science and technology, nano material show increasingly heavier in the application of various fields
The status wanted.Nano medicament carrying system has the stability for improving medicine, the toxic side effect for reducing medicine, realizes the gentle controlled release of targeting
The advantages that medicine and raising bioavilability, cause the concern of biomedicine field.
Graphene oxide has stable two-dimentional monoatomic layer structure, and specific surface area is big, and drugloading rate is big, biocompatibility
It is good.Meanwhile can be reacted by oxygen-containing activated group and specific material and functional modification is carried out to graphene oxide, with up to
To different application purposes.These attributes make graphene oxide become a kind of preferably load and transmit the material of multi-medicament,
Such as adriamycin, ellagic acid, camptothecine.In recent years, graphene oxide is shown very big at numerous aspects of biomedical sector
Application potential, thus paid close attention to be subject to numerous researchers.
But the graphene oxide of unmodified mistake is all quicker to solution environmentals such as solute, acid-base value, ionic strengths
Sense, and under physiological environment（Such as cell culture fluid, phosphate buffer）Solubility is very poor, easily reunites, this is certain
Its application is limited in degree.Graphene oxide, can be by right in vivo and without functionalization effects such as targeting, slow controlled releases
Graphene oxide carries out functionalization, while its stability is increased, also assigns the new functions such as its targeting, slow controlled release.Oxidation
The shortcomings that functional modification of graphene can be divided into covalent functionalization and non-covalent functionalization, covalent modification is decorating molecule and oxygen
Active force between graphite alkene is very strong, and organic solvent is used in preparation process, may be harmful；Therefore, it is of the invention
It is lipid-modified to graphene oxide progress using noncovalent interaction, prepare simply and without using organic solvent.Non-covalent bond function
Change is using non-covalent bond effects such as π π interactions, ionic bond, hydrogen bond and electrostatic interactions, and function is carried out to graphene oxide
Change to improve the dispersiveness and stability of graphene oxide.
Liposome (liposome) is to be scattered in vesicle formed in water phase by lipoid molecule, with membrane structure
Similar, its main component is phosphatide and cholesterol.Make pharmaceutical carrier, liposome has targeting, sustained release and long-acting, reduction
The toxicity of medicine, increase the advantages that stability and good histocompatbility and cellular affinity of medicine.
The graphene oxide of nano-scale is made using sonioation method by the present invention, and lipid is synthesized by rotary evaporation
Body, then carries out surface modification using electrostatic interaction to graphene oxide, has obtained stability in physiological conditions with this and has divided
The all preferable graphene oxide-lipid nanometer of scattered property answers material.Meanwhile the parcel of lipid makes pharmaceutical carrier have target slow-release
Effect, significantly reduces poisonous side effect of medicine.
The content of the invention
Graphene oxide layer is environmentally sensitive the invention aims to solving, and easily reunites under physiological environment
Shortcoming, there is provided a kind of preparation method of graphene oxide-lipid composite material, the carrier material hydrophily is strong, under physiological condition
Dispersiveness and stability are good, and drugloading rate is big, Targeting delivery, can reduce toxic side effect of the medicine to body, have a wide range of applications
Prospect.
Present invention firstly provides a kind of graphene oxide-lipid composite material；
The present invention also provides a kind of preparation method of graphene oxide-lipid nanometer composite material, follow the steps below：
（1）Graphene oxide is soluble in water, suspension is obtained, water bath sonicator, obtains graphene oxide aqueous dispersions；
（2）Among yolk phospholipid is dissolved in chloroform, it is placed on Rotary Evaporators and rotates film forming, obtain liposome, it is then plus water-soluble
Acid phosphate buffer solution, rotation make film come off, up to Liposomal dispersion after ultrasound；
（3）By step（1）The magnetic oxygenated graphene and step（2）The Liposomal dispersion mixing is placed on constant temperature
Stirred in oscillator, centrifugation is precipitated, and is dissolved with aqueous phosphate buffer, and ultrasound, receives up to graphene oxide-lipid
Nano composite material.
Step（1）Described in ultrasonic power 250W-400W, 0.5 h-2 h of ultrasonic time, ice-water bath.
Step（1）Described in graphene oxide aqueous dispersions concentration be 0.2 mg/mL-1 mg/mL.
Step（2）Described in yolk phospholipid and chloroform mass ratio be 1:75.
Step（2）Described in the concentration of Liposomal dispersion be 35 mg/mL.
Step（3）Described in liposome and graphene oxide mass ratio be 1:10~30.
In terms of the graphene oxide-lipid nanometer composite material is applied to antineoplastic drug carrier.
Beneficial effects of the present invention：
（1）Graphene oxide prepared by the present invention-lipid nanometer composite material, particle diameter is in the range of 200400 nm, drugloading rate
Up to 120%, after lipid-modified, hence it is evident that improve the dispersed and easily reunion in physiological conditions of carrier material in water
The shortcomings that.By 48 h, GO produces obvious coagulation phenomenon in cell culture fluid, and GO-lipo is in three kinds of decentralized media
Keep good dispersiveness and stability.
（2）Compared with common nanoparticle, the modification of lipid makes pharmaceutical carrier have the function of targeting positioning, i.e.,
It can target at lower ph and rapidly discharge medicine, reduce the toxic side effect of medicine, have broad application prospects.
（3）The preparation method of graphene oxide of the present invention-lipid composite material, oxygen is improved by non-covalent modification
The shortcomings that graphite alkene is easily reunited in physiological conditions.
（4）The present invention is easy to operate, and cost is low, is easy to mass produce, and can be widely applied to sensor and is cured with biology
The fields such as medicine, are especially applied to carry medicine and drug controlled release field.
Brief description of the drawings
Fig. 1 is the graphene oxide prepared by embodiment 1（a）With graphene oxide-lipid（b）The atomic force microscopy of material
Mirror collection of illustrative plates（The coordinate diagram on right side represents the concrete numerical value of the thickness of the particle on drawn straight line in AFM collection of illustrative plates）；
Fig. 2（a）It is the graphene oxide prepared by embodiment 1 respectively in pure water（It is left）, phosphate buffer（PBS, pH are
7.4）With containing 10% hyclone RPMI-1640 nutrient solutions（It is right）In study on the stability figure；
Fig. 2（b）It is graphene oxide-lipid prepared by embodiment 1 respectively in pure water（It is left）, phosphate buffer（PBS,
PH is 7.4）With containing 10% hyclone RPMI-1640 nutrient solutions（It is right）In study on the stability figure；
Fig. 3 is the adriamycin that dissociates in embodiment 4（a）, graphene oxide-adriamycin（b）With graphene oxide-lipid-adriamycin
（c）The scatter diagram in PBS solution；
Fig. 4 is the tablets in vitro figure of graphene oxide-lipid-adriamycin composite material in embodiment 5.
Embodiment
With reference to specific embodiment, the present invention is described further, but protection scope of the present invention is not limited in
This：
Embodiment 1：
（1）Graphene oxide aqueous dispersions are broken into the graphene oxide aqueous dispersions of nano-scale, work(with cell crushing instrument
Rate 400w, 0.5 h of ultrasonic time, carry out in ice-water bath；（2）Yolk phospholipid is weighed, and is dissolved in suitable chloroform, then
Measure the solution to be placed in eggplant-shape bottle, rotation film forming is allowed to using Rotary Evaporators（First rotation half a minute vacuumizes again）.Then
Appropriate PBS solution is added into container and rotating makes film come off；（3）Content in eggplant-shape bottle is poured into 10 mL centrifuge tubes
In, ultrasonic disperse is allowed to clarify；（4）Prepare the graphene oxide water solution that a certain amount of concentration is 1 mg/mL.Take 5 mL
Centrifuge tube is some, is separately added into the matter of graphene oxide solution, liposome solutions and appropriate pure water, graphene oxide and liposome
Amount is than being 15：1, it is placed in constant temperature oscillator and is stirred overnight（37℃）；（5）Solution is centrifuged（13000r, 30 min）, discard
Clearly, precipitation is scattered in appropriate PBS solution, ultrasonic disperse is allowed to clarify, and obtains lipid-modified graphene oxide（Concentration 0.2
mg/mL）.
As shown in atomic force microscopy diagram spectrum result（Fig. 1 a）, the average-size of graphene oxide is in 200 ± 2 nm, thickness
In 1 nm or so, the graphene oxide for successfully preparing nano-scale using clasmatosis method is indicated.By liposome
After on to graphene oxide, thickness increases to 8nm, this illustrates the surface that lipid has successfully been coated to graphene oxide.
Particle diameter measurements also indicate that graphene oxide particle diameter is 237 ± 2 nm, and the particle diameter of lipid-modified graphene oxide then increases
To 250 ± 2 nm, particle diameter is increased slightly, but is still in Nano grade, this explanation successfully arrives liposome
The surface of graphene oxide, and lipid-modified graphene oxide favorable dispersibility.The Zeta potential of graphene oxide is ﹣
33.82 mV, the current potential of liposome is 40.36 mV of ﹣；And it is changed into 42.79 mV of ﹣ through lipid-modified graphene oxide current potential,
The change of Zeta potential shows that successfully parcel arrives surface of graphene oxide to liposome.Stability result（As shown in Figure 2）
Show, graphene oxide-lipid keeps good dispersiveness and stability in three kinds of decentralized media.Further relate to use lipid
Body can obviously improve the shortcomings that graphene oxide is easily reunited in physiological environment, enhancing after surface modification is carried out to graphene oxide
Its stability and dispersiveness.
Embodiment 2：
（1）Graphene oxide aqueous dispersions are broken into the graphene oxide aqueous dispersions of nano-scale, work(with cell crushing instrument
Rate 300w, 1 h of ultrasonic time, carry out in ice-water bath；（2）Yolk phospholipid is weighed, and is dissolved in suitable chloroform, Ran Houliang
Take the solution to be placed in eggplant-shape bottle, rotation film forming is allowed to using Rotary Evaporators（First rotation half a minute vacuumizes again）, it is then past
Appropriate PBS solution is added in container and rotating makes film come off；（3）Content in eggplant-shape bottle is poured into 10 mL centrifuge tubes,
Ultrasonic disperse is allowed to clarify；（4）The graphene oxide water solution that a certain amount of concentration is 1 mg/mL is prepared, takes 5 mL to centrifuge
Manage some, be separately added into the mass ratio of graphene oxide solution, liposome solutions and appropriate pure water, graphene oxide and liposome
For 10：1, it is placed in constant temperature oscillator and is stirred overnight（37℃）；（5）Solution is centrifuged（13000r, 30 min）, supernatant discarding will
Precipitation is scattered in appropriate PBS solution, and ultrasonic disperse is allowed to clarify, and obtains lipid-modified graphene oxide（0.2 mg/ of concentration
mL）.
Particle diameter measurements show that graphene oxide particle diameter is 229 ± 2nm, and particle diameter is changed into 246 ± 2 after lipid-modified
nm.The Zeta potential of graphene oxide is 33.78 mV of ﹣, and after lipid encapsulation, Zeta potential is changed into 41.58 mV of ﹣.
Embodiment 3：
（1）Graphene oxide aqueous dispersions are broken into the graphene oxide aqueous dispersions of nano-scale, work(with cell crushing instrument
Rate 250w, 1.5 h of ultrasonic time, carry out in ice-water bath；（2）Yolk phospholipid is weighed, and is dissolved in suitable chloroform, then
Measure the solution to be placed in eggplant-shape bottle, rotation film forming is allowed to using Rotary Evaporators（First rotation half a minute vacuumizes again）, then
Appropriate PBS solution is added into container and rotating makes film come off；（3）Content in eggplant-shape bottle is poured into 10 mL centrifuge tubes
In, ultrasonic disperse is allowed to clarify；（4）The graphene oxide water solution that a certain amount of concentration is 1 mg/mL is prepared, takes 5 mL
Centrifuge tube is some, is separately added into the quality of graphene oxide solution, phospholipid solution and appropriate pure water, graphene oxide and liposome
Than for 20：1, which is placed in constant temperature oscillator, is stirred overnight（37℃）；（5）Solution is centrifuged（13000r, 30 min）, supernatant discarding will
Precipitation is scattered in appropriate PBS solution, and ultrasonic disperse is allowed to clarify, and obtains lipid-modified graphene oxide（0.2 mg/ of concentration
mL）.
Particle diameter measurements show that graphene oxide particle diameter is 231 ± 2 nm, after lipid-modified particle diameter be changed into 258 ±
2 nm.The Zeta potential of graphene oxide is 34.08 mV of ﹣, and after lipid encapsulation, Zeta potential is changed into 42.36 mV of ﹣.
Embodiment 4：
（1）Graphene oxide aqueous dispersions are broken into the graphene oxide aqueous dispersions of nano-scale, work(with cell crushing instrument
Rate 250w, 1.5 h of ultrasonic time, carry out in ice-water bath；（2）Yolk phospholipid is weighed, and is dissolved in suitable chloroform, then
Measure the solution to be placed in eggplant-shape bottle, rotation film forming is allowed to using Rotary Evaporators（First rotation half a minute vacuumizes again）, then
Appropriate PBS solution is added into container and rotating makes film come off；（3）Content in eggplant-shape bottle is poured into 10 mL centrifuge tubes
In, ultrasonic disperse is allowed to clarify；（4）The graphene oxide water solution that a certain amount of concentration is 1 mg/mL is prepared, takes 5 mL
Centrifuge tube is some, is separately added into the quality of graphene oxide solution, phospholipid solution and appropriate pure water, graphene oxide and liposome
Than for 30：1, which is placed in constant temperature oscillator, is stirred overnight（37℃）；（5）Solution is centrifuged（13000r, 30 min）, supernatant discarding will
Precipitation is scattered in appropriate PBS solution, and ultrasonic disperse is allowed to clarify, and obtains lipid-modified graphene oxide（0.2 mg/ of concentration
mL）.
Particle diameter measurements show that graphene oxide particle diameter is 230 ± 2 nm, after lipid-modified particle diameter be changed into 254 ±
2 nm.The Zeta potential of graphene oxide is 34.08 mV of ﹣（Fig. 2）, after lipid encapsulation, Zeta potential is changed into 42.36 mV of ﹣.
Example 5：Load the preparation of graphene oxide-lipid composite material of adriamycin
Graphene oxide -200 mg of lipid composite material is taken, is placed in centrifuge tube, adds Doxorubicin solution（1 mg/mL）200 μ
L, 24 h of isothermal vibration（37℃）, centrifugation, takes supernatant to dilute, and at 480 nm, supernatant is measured with ultraviolet spectrophotometry
With the absorbance of adriamycin comparison liquid, and then calculate drugloading rate.Test result indicates that the adriamycin of graphene oxide-lipid is born
Carrying capacity is 121.2%, relatively low compared with graphene oxide, but it significantly improves graphene oxide-lipid-adriamycin in physiology
Condition（PBS buffer, cell culture fluid etc.）Under stability（Fig. 3）.
Example 6：The insoluble drug release for loading graphene oxide-lipid composite material of adriamycin is investigated
1mL is carried medicine graphene oxide-lipid to be added separately in bag filter, is tightened, being then immersed into 20 mL pH is
In 5.0 and 7.4 PBS buffer solutions, vibration and timing in 37 DEG C of constant temperature oscillation casees are placed on, successively will in different time points
Dissolution medium all takes out and is supplemented in 20 new mL PBS buffer after persistent oscillation.By the dissolution medium of taking-up fluorescence point
Light photometry（Excitation wavelength is 488 nm, and measure wavelength is 591 nm, 10 nm of slit）Its fluorescence intensity is measured, then basis
Standard curve tries to achieve the burst size of adriamycin.Acquired results are as shown in figure 4, medicine has substantially from the release in the carrier material
PH dependences, discharged when pH is relatively low comparatively fast, burst size is big, can be effectively reduced the toxic side effect of medicine.
Claims (8)
1. a kind of graphene oxide-lipid nanometer composite material, it is characterised in that the composite material is with the oxidation of nano-scale
Graphene is kernel, yolk phospholipid is synthesized liposome by rotary evaporation, liposome is wrapped up by electrostatic adsorption
On the surface of carrier.
2. a kind of graphene oxide-lipid nanometer composite material and preparation method thereof, it is characterised in that include the following steps：
（1）Graphene oxide is soluble in water, suspension is obtained, water bath sonicator, obtains graphene oxide aqueous dispersions；
（2）Among yolk phospholipid is dissolved in chloroform, it is placed on Rotary Evaporators and rotates film forming, obtain liposome, it is then plus water-soluble
Acid phosphate buffer solution, rotation make film come off, up to Liposomal dispersion after ultrasound；
（3）By step（1）The magnetic oxygenated graphene and step（2）The Liposomal dispersion mixing is placed on constant temperature
Stirred in oscillator, centrifugation is precipitated, and is dissolved with aqueous phosphate buffer, and ultrasound, receives up to graphene oxide-lipid
Nano composite material.
3. a kind of preparation method of graphene oxide-lipid nanometer composite material according to claim 2, its feature exist
In step（1）Described in ultrasonic power 250W-400W, 0.5 h-2 h of ultrasonic time, ice-water bath.
4. a kind of preparation method of graphene oxide-lipid nanometer composite material according to claim 2, its feature exist
In step（1）Described in graphene oxide aqueous dispersions concentration be 0.2 mg/mL-1 mg/mL.
5. a kind of preparation method of graphene oxide-lipid nanometer composite material according to claim 2, its feature exist
In step（2）Described in yolk phospholipid and chloroform mass ratio be 1:75.
6. a kind of preparation method of graphene oxide-lipid nanometer composite material according to claim 2, its feature exist
In step（2）Described in the concentration of Liposomal dispersion be 35 mg/mL.
7. a kind of preparation method of graphene oxide-lipid nanometer composite material according to claim 2, its feature exist
In step（3）Described in liposome and graphene oxide mass ratio be 1:10~30.
A kind of 8. graphene oxide-lipid nanometer composite material application according to any claim in claim 1-7
In the preparation of Drug controlled release and antineoplastic drug carrier.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108653212A (en) * | 2018-06-22 | 2018-10-16 | 江苏大学 | A kind of preparation method and application of lipid-modified molybdenum disulfide nano-composite material |
| CN111149798A (en) * | 2020-01-09 | 2020-05-15 | 华南农业大学 | Water-based graphene oxide nano pesticide and preparation method and application thereof |
| CN111500284A (en) * | 2020-05-13 | 2020-08-07 | 暨南大学 | Nano-liposome encapsulating graphene quantum dots, preparation and application thereof in biological enzyme activity detection |
| CN114314575A (en) * | 2021-11-27 | 2022-04-12 | 徐玲艳 | Preparation device and method of liposome modified nano graphene |
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2017
- 2017-11-23 CN CN201711178589.4A patent/CN107970454B/en active Active
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108653212A (en) * | 2018-06-22 | 2018-10-16 | 江苏大学 | A kind of preparation method and application of lipid-modified molybdenum disulfide nano-composite material |
| CN111149798A (en) * | 2020-01-09 | 2020-05-15 | 华南农业大学 | Water-based graphene oxide nano pesticide and preparation method and application thereof |
| CN111500284A (en) * | 2020-05-13 | 2020-08-07 | 暨南大学 | Nano-liposome encapsulating graphene quantum dots, preparation and application thereof in biological enzyme activity detection |
| WO2021227336A1 (en) * | 2020-05-13 | 2021-11-18 | 暨南大学 | Nanoliposome encapsulating graphene quantum dot, preparation, and application thereof in activity detection of bioenzyme |
| CN114314575A (en) * | 2021-11-27 | 2022-04-12 | 徐玲艳 | Preparation device and method of liposome modified nano graphene |
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