CN109394700A - A kind of preparation method of the nano-complex of the graphene oxide-loaded polypentenol-fullerene of chitosan- - Google Patents
A kind of preparation method of the nano-complex of the graphene oxide-loaded polypentenol-fullerene of chitosan- Download PDFInfo
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- CN109394700A CN109394700A CN201811606281.XA CN201811606281A CN109394700A CN 109394700 A CN109394700 A CN 109394700A CN 201811606281 A CN201811606281 A CN 201811606281A CN 109394700 A CN109394700 A CN 109394700A
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Abstract
The present invention provides a kind of preparation methods of the nano-complex of the graphene oxide-loaded polypentenol-fullerene of chitosan-, its main feature is that: (1) toluene solution of fullerene and polypentenol is slowly dropped in emulsifier, heating stirring obtains oily phase；After stable system, a certain amount of deionized water phase inversion is added, then improves temperature, a large amount of deionized waters are added, are stirred by ultrasonic wave added, obtains polypentenol/fullerene nanoemulsions；(2) chitosan-acetic acid solution is slowly added dropwise into graphene oxide water solution, after heating stirring, folic acid ammonia spirit is slowly added dropwise into wherein, heating stirring finishes to get chitosan-graphene oxide compound dispersion liquid；(3) after step (1), (2) resulting two kinds of liquid heating stirrings being mixed, sodium tripolyphosphate solution is slowly added thereto, after being stirred under heating, the chilled nano-complex being dried in vacuo up to the graphene oxide-loaded polypentenol-fullerene of chitosan-.
Description
Technical field
The present invention relates to a kind of preparations of the nano-complex of the graphene oxide-loaded polypentenol-fullerene of chitosan-
Method belongs to biomedicine field.
Technical background
Polypentenol (polyprenols, GBP) is with C5Isopentene group is the lipids of structural unit, is biology
Important activity ingredient in body cell film in glycoprotein synthesis process, participates in a variety of metabolism in organism, and bioactivity is very wide
It is general.Polypentenol is the key product of biological cell membrane glycoprotein biosynthesis, is distributed with free state alcohol or phosphate form
In cell membrane, and a variety of physiological metabolism activities in organism can be participated in, therefore polypentenol can be used as good drug fortune
Transmission carrier.Drug is sent into cell interior as good biological cell membrane carrier using polypentenol and participates in metabolism, it can be compared with
The bioavilability and targeting of good raising drug, to achieve the purpose that reduce drug usage amount and side effect.
Early-stage study absolutely proves that polypentenol has the active synergistic effect of certain antibacterial, anticancer drug, therefore will
Polypentenol exploitation has good application prospect at medicament synergistic agent.Polypentenol has strong-hydrophobicity, water is insoluble in, in people
Body and the intracorporal bioavilability of animal are lower, more influence its bioactivity research and related preparations exploitation.Therefore, by receiving
Polypentenol is effectively embedded or is dispersed by rice preparation technique, is the pass for solving related preparations and its bioavailability concerns
Key.Chitosan is the alkaline glycosaminoglycan of cation in natural polysaccharide, and good biocompatibility is nontoxic, no antigen, biological can drop
Solution, can encapsulate the compound of opposed polarity, be a kind of excellent pharmaceutical carrier.Chitosan and liposoluble constituent such as unsaturated fat
Acid, cholesterol etc. are that have good biocompatibility and stability with interaction of hydrogen bond.The amino cation of chitosan with
The phospho anion of sodium tripolyphosphate carries out intramolecular or intermolecular cross-linking by electrostatic attraction, can be further formed load rouge
The chitosan-sodium tripolyphosphate nano-carrier of soluble components.Folic acid is vitamin B11, can be used as enzyme and come synthetic DNA, body growth
Folic acid is required with breeding, is the important coenzyme of one carbon unit transferase.Folic acid does not poison, is more stable, immunogenicity is weak,
It specifically can act on forming compound with the folacin receptor of cell surface, both binding force is very strong, has height to tumour
Selectivity, therefore folic acid is often used as the modified compound of tumor-targeting drug.C60Fullerene is in a kind of simple substance carbon
Three kinds of allotropes being found have cagelike structure, possess 60 P tracks, and the big pi bond constituted can form a kind of conjugation
System, so that it has the ability by electronics and electron.C60Fullerene is caught due to its excellent strong anti-oxidation, free radical
Catch, the characteristics such as light absorption, superconducting semiconductor, perfect structure, DNA is affine, electron acceptor, efficient absorption, embedded molecule, by
It is widely applied to daily cosmetics, medicine intermediate, health care product, rubber/thin-film material modifying agent, high new energy, composite material
The numerous areas such as additive.Graphene oxide is to prepare gained generally by graphite oxide, i.e., introduces in graphene molecules
The oxygen-containing groups such as carboxyl, hydroxyl, epoxy group can be dispersed in water and other hydrophilic solvents, have good bio-compatible
Property and can functionalization feature, it can be achieved that drug it is orderly adsorb and release action.
The present invention is prepared for the oil-in-water type of load polypentenol and fullerene using the methods of ultrasonic wave added emulsification first
Nanoemulsions are the nanoemulsions of basic active matter with polypentenol and fullerene.It is medium, benefit based on above-mentioned nanoemulsions
With folacin coupled chitosan and graphene oxide, and it is prepared for using ionic cross-linking the nanometer of load polypentenol and fullerene
The nano-complex of the graphene oxide-loaded polypentenol-fullerene of compound, i.e. chitosan-, meets the parent of polypentenol
Water formulation requirement improves bioavilability, increases the purpose of bioactivity to reach.
Summary of the invention
To achieve the above object, the nanometer for having invented a kind of graphene oxide-loaded polypentenol-fullerene of chitosan-is multiple
The preparation method of object is closed, the technical proposal for solving the technical problem of the invention is as follows.
The method for making the nano-complex of the graphene oxide-loaded polypentenol-fullerene of above-mentioned chitosan-, technique
Step is:
The first step, polypentenol-fullerene nanoemulsions preparation: by the toluene solution containing fullerene and polypentenol
It is slowly dropped in the mixture that emulsifier is Triton X-100 and n-octyl alcohol, and in 35~50 DEG C of heating conditions
Under, it stirs at low speed, obtains oily phase；After stable system, stirs at low speed down and continuously add a certain amount of deionized water phase inversion, body
System will be become muddy from clarification, and then under 50~80 DEG C of heating conditions, a large amount of deionized waters are added, and pass through ultrasonic wave added high speed
0.1~1h is stirred, system, which becomes transparent or semitransparent shape, can be obtained polypentenol/fullerene nanoemulsions；
Second step, chitosan-graphene oxide compound dispersion liquid preparation: by certain density chitosan-acetic acid solution
It is slowly added dropwise into graphene oxide water solution, 1~10h is heated and stirred at low speed at 45~70 DEG C, it then will be certain density
Folic acid ammonia spirit is slowly added dropwise into wherein, and 1~10h is heated and stirred at low speed at 45~70 DEG C, finishes up to chitosan-oxidation
Graphene complex dispersion liquid；
Third step, the preparation of the nano-complex of the graphene oxide-loaded polypentenol-fullerene of chitosan-: by first
The resulting polypentenol of one step process-fullerene nanoemulsions are slowly added into the resulting chitosan-graphite oxide of the second one step process
In alkene compound dispersion liquid, 1~5h is heated and stirred at low speed at 35~50 DEG C, it is then that certain density sodium tripolyphosphate is molten
Liquid is slowly added thereto, and 1~10h is heated and stirred at low speed at 45~70 DEG C, after chilled be dried in vacuo up to chitosan-
The nano-complex of graphene oxide-loaded polypentenol-fullerene.
Fullerene mass percent contained by the toluene solution of fullerene and polypentenol is in the first step of the present invention
0.01%~1%, contained polypentenol mass percent is 0.1%~8%；Emulsifier be Triton X-100 with
The mass ratio of n-octyl alcohol is 1: 1~5；The toluene solution and emulsifier of fullerene and polypentenol are 1: 0.2 using mass ratio
~10；The power of ultrasound is 400~600W.
Acetic acid quality percentage is 1%~5% in acetum in second step of the present invention；Shell is poly- in chitosan-acetic acid solution
The mass percent of sugar is 0.1%~10%；Mass percent in graphene oxide water solution containing graphene oxide is
0.05%~5%；Mass percent in ammonia spirit containing ammonia is 1%~3%；The quality percentage of folic acid in folic acid ammonia spirit
Than being 0.1%~5%；The mass ratio that uses of folic acid and chitosan and graphene oxide is 1: 10~100: 1~10.
Polypentenol-fullerene nanoemulsions and chitosan-graphene oxide compound dispersion liquid in third step of the present invention
The mass ratio that uses with sodium tripolyphosphate solution is 1: 1~100: 1~10, contains sodium tripolyphosphate in sodium tripolyphosphate solution
Mass percent is 0.1%~5%.
The polypentenol is from any one of ginkgo leaf, pine needle and mulberry leaf.
The rate stirred at low speed is 200~1000r/min；The rate of high-speed stirred is 10000~15000r/
min。
Beneficial effects of the present invention show themselves in that
It is negative that the present invention uses the methods of ultrasonic wave added emulsification coupled ion crosslinking to be prepared for a kind of chitosan-graphene oxide
Polypentenol-fullerene nano-complex is carried, particle diameter distribution is up to 27.3~82.1nm, average grain diameter in lotion
44.9nm；The carrying drug ratio of polypentenol and fullerene is respectively 24.77% and 3.81%, and encapsulation rate is respectively 91.40% He
93.32%；Release Performance is good, no phenomenon of burst release；Internal stability is good within three months；It is thin to the high metastatic hepatic carcinoma of MHCC97H people
The proliferation of born of the same parents and transfer have obvious inhibiting effect.
Nano-complex character made of the present invention is stablized, and water dispersible is good, and biological action is obvious.The dosage form can
Meet scientific research relevant biological activity requirement of experiment, and may be added to that fluid, semifluid and other higher correlation systems of water content
In agent or product, the hydrophilic formulation requirement of polypentenol had not only been met, but also can reach and improve bioavilability, increase bioactivity
The purpose of.
Nano-complex character made of the present invention is stablized, and water dispersible is good, overcomes polypentenol because hydrophobicity is strong
And molecular weight is larger, it is difficult to the problems such as being balanced in water phase, to improve polypentenol in scientific research, functional food and medicine
In field a possibility that practical application.
The invention avoids the participations of the toxic compounds such as the method for chemical crosslinking such as aldehydes, utilize nontoxic trimerization
The phospho anion of sodium phosphate and the amino cation of chitosan carry out intramolecular or intermolecular cross-linking by electrostatic attraction, both
The bioactivity of original matrix, and safety and environmental protection are increased, has in practical application and correlation function product development and well answers
Use prospect.
The nano-complex of the graphene oxide-loaded polypentenol-fullerene of chitosan-made of the present invention has good
Anticancer activity, can be developed into functional food and drug with anti-cancer function.
Detailed description of the invention:
The scanning electron microscope analysis figure of the nano-complex of the graphene oxide-loaded polypentenol-fullerene of Fig. 1 chitosan-
Particle diameter distribution of the nano-complex of the graphene oxide-loaded polypentenol-fullerene of Fig. 2 chitosan-in lotion
Figure
Specific embodiment
Following embodiment is some citings of the invention, should not be seen as limitation of the invention.
The preparation of 1 polypentenol of embodiment-fullerene nanoemulsions
It is poly- that the 10mL toluene solution for containing 0.1% fullerene and 2% polypentenol, which is slowly dropped to 50mL emulsifier,
In the mixture of ethylene glycol octyl phenyl ether and n-octyl alcohol (mass ratio 1: 1, HLB value 9.2), and under 40 DEG C of heating conditions,
It is stirred evenly with 500r/min speed, obtains oily phase；After stable system, to continuously add 20% under the stirring of 500r/min speed
Deionized water phase inversion is measured, system will be become muddy from clarification, then under 70 DEG C of heating conditions, 5 times of amount deionized waters are added,
The ultrasonic wave added of 500W power simultaneously stirs 0.25h simultaneously with 12000r/min speed, and system becomes transparent or semitransparent shape
Obtain polypentenol/fullerene nanoemulsions.
The preparation of 2 chitosans of embodiment-graphene oxide compound dispersion liquid
The 100mL acetum for containing 1% chitosan is slowly added dropwise into 40mL and contains the water-soluble of 0.1% graphene oxide
In liquid, is heated at 60 DEG C and 10h is stirred with 500r/min speed, then slowly drip the ammonia spirit that 4mL contains 0.5% folic acid
It is added thereto, is heated at 70 DEG C and 10h is stirred with 500r/min speed, finish up to chitosan-graphene oxide compound point
Dispersion liquid；
The preparation and performance of 3 chitosan of embodiment-graphene oxide-loaded polypentenol-fullerene nano-complex
Measurement result
The resulting polypentenol of 10mL embodiment 1-fullerene nanoemulsions are slowly added into 2 gained of 100mL embodiment
Chitosan-graphene oxide compound dispersion liquid in, and at 50 DEG C heat with 500r/min speed stir 5h, will then contain
There is the solution of 1% sodium tripolyphosphate to be slowly added thereto, heated at 60 DEG C and 10h is stirred with 500r/min speed, is passed through after finishing
Vacuum freezedrying is for 24 hours above to get the nano-complex of the graphene oxide-loaded polypentenol-fullerene of chitosan-.
The nano-complex of polypentenol-fullerene graphene oxide-loaded to chitosan-made of the above method carries out
Performance measurement, stability and biological activity determination, as the result is shown the material in lotion particle diameter distribution up to 27.3~82.1nm,
Average grain diameter is 44.9nm；The carrying drug ratio of polypentenol and fullerene is respectively 24.77% and 3.81%, and encapsulation rate is respectively
91.40% and 93.32%；Release Performance is good, no phenomenon of burst release；Internal stability is good within three months；MHCC97H people's height is shifted
Property liver cancer cells proliferation and transfer have obvious inhibiting effect.
Claims (9)
1. a kind of preparation method of the nano-complex of the graphene oxide-loaded polypentenol-fullerene of chitosan-, feature exist
In:
(1) polypentenol-fullerene nanoemulsions preparation: the toluene solution containing fullerene and polypentenol is slowly added dropwise
It is to emulsifier in the mixture of Triton X-100 and n-octyl alcohol, and under 35~50 DEG C of heating conditions, low speed is stirred
It mixes uniformly, obtains oily phase；It after stable system, stirs at low speed down and continuously adds a certain amount of deionized water phase inversion, system will be by clear
Become muddy clearly, then under 50~80 DEG C of heating conditions, a large amount of deionized waters are added, pass through ultrasonic wave added high-speed stirred 0.1
~1h, system, which becomes transparent or semitransparent shape, can be obtained polypentenol/fullerene nanoemulsions；
(2) chitosan-graphene oxide compound dispersion liquid preparation: certain density chitosan-acetic acid solution is slowly added dropwise
Into in graphene oxide water solution, 1~10h is heated and stirred at low speed at 45~70 DEG C, then by certain density folic acid ammonium hydroxide
Solution is slowly added dropwise into wherein, and 1~10h is heated and stirred at low speed at 45~70 DEG C, finishes multiple up to chitosan-graphene oxide
Close object dispersion liquid；
(3) preparation of the nano-complex of the graphene oxide-loaded polypentenol-fullerene of chitosan-: by step (1) method institute
Polypentenol-fullerene the nanoemulsions obtained are slowly added into the resulting chitosan of step (2) method-graphene oxide compound
In dispersion liquid, 1~5h is heated and stirred at low speed at 35~50 DEG C, then slowly adds certain density sodium tripolyphosphate solution
Enter wherein, 1~10h heated and stirred at low speed at 45~70 DEG C, after chilled be dried in vacuo up to chitosan-graphite oxide
Alkene loads polypentenol-fullerene nano-complex.
2. a kind of nano-complex of the graphene oxide-loaded polypentenol-fullerene of chitosan-according to claim 1
Preparation method, it is characterised in that polypentenol is any one of from ginkgo leaf, pine needle and mulberry leaf.
3. a kind of nano-complex of the graphene oxide-loaded polypentenol-fullerene of chitosan-according to claim 1
Preparation method, it is characterised in that fullerene quality contained by the toluene solution of fullerene described in step (1) and polypentenol
Percentage is 0.01%~1%, and contained polypentenol mass percent is 0.1%~8%；Emulsifier is polyethylene glycol octyl
The mass ratio of phenyl ether and n-octyl alcohol is 1: 1~5；The toluene solution and emulsifier of fullerene and polypentenol use mass ratio
It is 1: 0.2~10；The power of ultrasound is 400~600W.
4. a kind of nano-complex of the graphene oxide-loaded polypentenol-fullerene of chitosan-according to claim 1
Preparation method, it is characterised in that in acetum described in step (2) acetic acid quality percentage be 1%~5%；Chitosan vinegar
The mass percent of chitosan is 0.1%~10% in acid solution；Containing the quality of graphene oxide in graphene oxide water solution
Percentage is 0.05%~5%；Mass percent in ammonia spirit containing ammonia is 1%~3%；Folic acid in folic acid ammonia spirit
Mass percent is 0.1%~5%；The mass ratio that uses of folic acid and chitosan and graphene oxide is 1: 10~100: 1~10.
5. a kind of nano-complex of the graphene oxide-loaded polypentenol-fullerene of chitosan-according to claim 1
Preparation method, it is characterised in that polypentenol described in step (3)-fullerene nanoemulsions and chitosan-graphene oxide
The mass ratio that uses of compound dispersion liquid and sodium tripolyphosphate solution is 1: 1~100: 1~10, is contained in sodium tripolyphosphate solution
The mass percent of sodium tripolyphosphate is 0.1%~5%.
6. a kind of nano-complex of the graphene oxide-loaded polypentenol-fullerene of chitosan-according to claim 1
Preparation method, it is characterised in that the rate stirred at low speed be 200~1000r/min；The rate of high-speed stirred be 10000~
15000r/min。
7. a kind of chitosan-graphene oxide-loaded poly- penta made from described in any item preparation methods according to claim 1~6
Enol-fullerene nano-complex.
8. a kind of nano-complex of the graphene oxide-loaded polypentenol-fullerene of chitosan-according to claim 7
Preparation method, it is characterised in that the nano-complex of the graphene oxide-loaded polypentenol-fullerene of the chitosan-exists
Particle diameter distribution is up to 27.3~82.1nm, average grain diameter 44.9nm in lotion；The carrying drug ratio of polypentenol and fullerene is respectively
24.77% and 3.81%, encapsulation rate is respectively 91.40% and 93.32%.
9. a kind of nano-complex of the graphene oxide-loaded polypentenol-fullerene of chitosan-according to claim 7
Preparation method, it is characterised in that the nano-complex of the graphene oxide-loaded polypentenol-fullerene of the chitosan-
Release Performance is good, no phenomenon of burst release；Internal stability is good within three months；To the proliferation of the high metastatic hepatic carcinoma cell of MHCC97H people
There is obvious inhibiting effect with transfer.
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Application publication date: 20190301 |