CN109394729A - A kind of medicine-carried system and preparation method thereof loading sulforaphen - Google Patents
A kind of medicine-carried system and preparation method thereof loading sulforaphen Download PDFInfo
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Abstract
The present invention relates to a kind of medicine-carried systems and preparation method thereof for loading sulforaphen, using self-assembly method, by chitosan oligosaccharide, gamma-polyglutamic acid and manganese-zinc ferrite nano-particles reinforcement, 100nm particle below is generated after three kinds of substance cross-linking reactions, loads the sulforaphen extracted in broccoli.The invention also discloses the preparation method and application of the sulforaphen preparation.Sulforaphen Nano medication of the invention, the drug-loading system is when pH is 5.5, simulate acid or alkali environment in tumour cell, it can be sustained more than for 24 hours, preparation is higher than 90%, has positive effect for treatment of cancer, it can not only significantly improve the stability of sulforaphen, and there is sustained release and targeted double effect, application prospect is boundless.
Description
Technical field
The invention belongs to biomedicine fields, are related to a kind of medicine-carried system and preparation method thereof for loading sulforaphen.
Background technique
The transfer mode of drug has vital influence for the therapeutic effect of cancer, and wherein tumor-targeting drug passes
Passing has very big challenge.Research with nanotechnology in field of biomedicine deepens continuously, magnetic Nano material also by
Many concerns.As a kind of important soft magnetic materials, its application value and long-term basic research make manganese-zinc ferrite
Such soft magnetic ferrite is widely used in transformer, magnetic core, magnetic head etc..In recent years, Nanosized Mn-Zn Ferrite is because its is soft
The features such as magnetic characteristic and higher stability, but tumor thermotherapy and in terms of get more and more people's extensive concerning.But
It is exposed magnetic ferrites nanostructure due to being easy induction with high specific surface area, stronger dipolar magnetic interaction
Intergranular aggregation causes partial size to increase, bad stability, is unable to reach the requirement of biomedical applications.Therefore, it is necessary to pass through
The surface modification of magnetic Nano structure reduces intergranular interaction, improves its water-soluble, stability and surface-functional.
Significantly, since the unsaturation of magnetic nanoparticle surface atom, leading to surface, there are many dangling bonds and high
Reactivity site easily makes its structure tend towards stability in conjunction with other atoms, this is provided for its effective surface modification
Possibility.
Chitosan oligosaccharide is the second largest renewable natural polymer for being only second to cellulose in the world.It has biology can
The many merits such as degradation, nontoxicity, bioactivity, biocompatibility and antibiotic property.Contain hydroxyl and amino, property in molecule simultaneously
Matter is more active, can be coupled, activated and be modified to it.Gamma-polyglutamic acid is a kind of water-soluble biodegradable
Polymer substance has the characteristics that edible, nontoxic, cohesiveness, moisture retention.Its application field covers medicine, chemical industry, food
The many aspects such as product, cosmetics and daily chemical product.Especially in field of medicaments, as drug targeting carrier, gamma-polyglutamic acid exists
It can be biodegradable into Endogenous Amino Acids in human body, have no toxic and side effect to human body.Simultaneously as it is there are more side chain carboxyl group, it can
It is used using after modifying it as pharmaceutical carrier.
Sulforaphen is the strongest a kind of isothiocyanate of vigor.Its antitumaous effect is in the breast cancer treatment of rat
It is confirmed.According to zoopery, the sulforaphen of broccoli and its extraction is effective functional food or anticarcinogen, is passed through
Induction II phase enzyme is combined with inhibition I phase enzyme (Cytochrome P450).But sulforaphen is a kind of unstable substance, to temperature
It is sensitive with pH, therefore stability and targeting are improved by medicine-carried system.
Summary of the invention
The present invention is directed to the above-mentioned problems in the prior art, provides a kind of medicine-carried system for loading sulforaphen, tool
There is higher stability and there is targeting and slow release, can be used for oncotherapy in biomedicine field.
Meanwhile the present invention also provides the preparation method of the medicine-carried system of above-mentioned load sulforaphen, using self-assembly method,
By chitosan oligosaccharide, gamma-polyglutamic acid and manganese-zinc ferrite nano-particles reinforcement, sulforaphen is loaded, method is easy to operate.
Technical solution of the present invention is as follows:
A kind of medicine-carried system loading sulforaphen wraps up chitosan oligosaccharide and γ-polyglutamic for manganese-zinc ferrite nano grain surface
The mass ratio of the mixture of acid, the manganese-zinc ferrite nano particle and chitosan, gamma-polyglutamic acid is 1:1~20:10
~200.
The drug-loading system is simulated acid or alkali environment in tumour cell, can be sustained more than for 24 hours, accumulation is released when pH is 5.5
Rate is put higher than 90%.
The drug-loading system simulates acid or alkali environment in human body, no slow release effect, and release rate is low when pH is 7.4
In 20%.
Preferably, the medicine-carried system, granularity are less than 100nm.
Preferably, the chitosan oligosaccharide molecular size range is 1KD, and gamma-polyglutamic acid molecular size range is 40KD.
Preferably, the manganese-zinc ferrite nano particle, partial size are 10~30nm, and polydispersity coefficient is below 0.2.
Preferably, the manganese-zinc ferrite nano particle, by FeCl3·6H2O、ZnSO4·7H2O、MnSO4·H2O is pressed
It is prepared according to iron, manganese, zinc molar ratio for 12:4:1.
The medicine-carried system of the load sulforaphen, drug loading rate is 10.26~11.67%, and entrapment efficiency is
25.15~27.25%.
The preparation method of the medicine-carried system of above-mentioned load sulforaphen, comprising the following steps:
(1) FeCl is weighed according to the ratio3·6H2O、ZnSO4·7H2O、MnSO4·H2O, is added deionized water, and stirring and dissolving is added
NaOH reacts 30-90 min；
(2) chitosan oligosaccharide of 1/3~2/3 amount is added, is stirred, reacts, is centrifuged after ultrasound, by bulky grain cryomilling therein
Processing；
(3) remaining chitosan oligosaccharide and gamma-polyglutamic acid are added, is reacted；Freeze-drying, obtains the load medicine body comprising manganese-zinc ferrite
System；
(4) 30min is stirred after carrying medicament sulforaphen being added after cooling；Magnet sedimentation separation after dialysis, last freezing vacuum
Drying, must load the medicine-carried system of sulforaphen.
The chitosan oligosaccharide that the present invention utilizes has the characteristics that antibacterial, nontoxic, good biocompatibility；Gamma-polyglutamic acid tool
There is the features such as moisturizing, nontoxic, good biocompatibility；；Nanosized Mn-Zn Ferrite is because of its soft magnetic characteristic and higher stability
Automatic adjustment heat source temperature can be achieved, there is targeting；Sulforaphen has the effect of very strong inhibition tumour, and four kinds of substances are certainly
100nm particle below is generated after assembling, this method is easy to operate.Beneficial effects of the present invention
1. combining the mode of action of magnetic thermotherapy and chemotherapy
The present invention loads the medicine-carried system of sulforaphen, the CS/ γ-PGA membrane structure and infiltration of nanocrystal surface under the influence of pH
Property change, and alternating magnetic field (ACMF) effect under, the magnetothermal effect based on its kernel, the CS/ γ-of nanocrystal surface
PGA membrane structure and permeability change, thus the drug controlled release for promoting it internal.It is high magnetic and main by playing carrier
Moving-target tropism, fully enrichment and alternation heat production, plays heat-therapeutic action in body tissue.Meanwhile heating can also promote drug
It is discharged into the sensitization of tumor tissues inside and drug molecule, to play Chemotherapy.To the drug for promoting it internal
Controlled release.The mode of action of complex carrier combination magnetic thermotherapy and chemotherapy of the present invention, institute's carrying medicament may be implemented in a period of time
Interior effective growth for inhibiting tumour, than the future that single thermotherapy or chemotherapy have more clinical practice application.
2. stability is good
Typical core-shell structure is presented in the medicine-carried system of the application, and kernel is spherical Magnetic Nanocrystals Containing, and shell is by uniform, cause
Close CS/ γ-PGA composition, shows good dispersibility, and have preferable stability；Magnetic characterization as the result is shown its have
There is superior magnetic property, and coercivity and remanent magnetism are approximately zero, embodies significant superparamagnetism.It is examined again after 40 days
Survey, as a result with it is consistent before, it was demonstrated that there is good stability.Drug release that is highly stable at normal temperature, and including simultaneously
Rate is lower.
Detailed description of the invention
Fig. 1 is the FTIR map of sulforaphen sample after silica gel column chromatography post separation；
Fig. 2 is chitosan oligosaccharide/gamma-polyglutamic acid nanoparticle transmission electron microscope (TEM)；
Fig. 3 is the transmission electron microscope (TEM) for the medicine-carried system that embodiment 3 loads sulforaphen；
Fig. 4 is that free sulforaphen and embodiment 3 load release profiles of the medicine-carried system of sulforaphen at different pH.
Specific embodiment
The present invention is further explained in the light of specific embodiments, but the present invention is not limited to following embodiments.
The preparation process of herein described sulforaphen are as follows:
1) it takes the broccoli seed of freeze-drying to be mechanically pulverized, deionized water is added and soaks seed powder, 30 min of ultrasound
Afterwards, 4 h are digested at 45 DEG C；Ethyl acetate, ultrasound 30 min of extraction is added in the sample digested, filter is collected in filter paper filtering
Liquid takes upper layer；Rotary evaporation is concentrated, and sulforaphen crude extract is obtained, and acetonitrile is added；3 mL sulforaphens of accurate measurement are thick
Extract solution, upper silica gel column chromatography；
2) upper silica gel column chromatography (cm of 2 cm × 20, wet method dress post), 3 mL of applied sample amount after extract filter membrane.With ethyl acetate:
Acetonitrile is eluent, flow velocity is transferred to 0.5 mL/min, every 2 mL collects 1 bottle.
The purity of the sulforaphen of extraction is 84.8 ± 2.4%, and the yield of every gram of broccoli seed (dry weight) sulforaphen is
5.9 mg。
Embodiment 1
A kind of medicine-carried system loading sulforaphen wraps up chitosan oligosaccharide and γ-polyglutamic for manganese-zinc ferrite nano grain surface
The mass ratio of the mixture of acid, the manganese-zinc ferrite nano particle and chitosan, gamma-polyglutamic acid is 1:1:10.
The preparation method of the medicine-carried system of above-mentioned load sulforaphen, comprising the following steps:
(1) it is 12:4:1 according to iron, manganese, zinc molar ratio, weighs FeCl3·6H2O、ZnSO4·7H2O、MnSO4·H2O is added
Deionized water, the agitating and heating at 95 DEG C are added NaOH and react 90 min；The manganese-zinc ferrite nano particle, partial size are
30nm；
(2) chitosan oligosaccharide of 1/3~2/3 amount is added, mixes, after 95 DEG C of reaction 1h, ultrasound, centrifugation, by bulky grain liquid nitrogen therein
Ball-milling treatment；Preferably, the chitosan oligosaccharide molecular size range is 1KD；
(3) remaining chitosan oligosaccharide is added and 60 DEG C of γ-polyglutamic acid is reacted 1h again, be freeze-dried, obtain comprising manganese-zinc ferrite
Reaction system, stir 30min after carrying medicament sulforaphen is added after cooling；Preferably, the medicine-carried system, granularity are small
In 100nm.Preferably, gamma-polyglutamic acid molecular size range is 40KD.
(4) 30min is stirred after carrying medicament sulforaphen being added after cooling；Magnet sedimentation separation after dialysis, finally freezes
Vacuum drying must load the medicine-carried system of sulforaphen.
Embodiment 2
A kind of medicine-carried system loading sulforaphen wraps up chitosan oligosaccharide and γ-polyglutamic for manganese-zinc ferrite nano grain surface
The mass ratio of the mixture of acid, the manganese-zinc ferrite nano particle and chitosan, gamma-polyglutamic acid is 1:20:200.
The preparation method of the medicine-carried system of above-mentioned load sulforaphen, comprising the following steps:
(1) it is 12:4:1 according to iron, manganese, zinc molar ratio, weighs FeCl3·6H2O、ZnSO4·7H2O、MnSO4·H2O is added
Deionized water, the agitating and heating at 95 DEG C are added NaOH and react 30 min；The manganese-zinc ferrite nano particle, partial size are
10nm；
(2) chitosan oligosaccharide of 1/3~2/3 amount is added, mixes, after 95 DEG C of reaction 1h, ultrasound, centrifugation, by bulky grain liquid nitrogen therein
Ball-milling treatment；Preferably, the chitosan oligosaccharide molecular size range is 1KD；
(3) remaining chitosan oligosaccharide is added and 60 DEG C of γ-polyglutamic acid is reacted 1h again, be freeze-dried, obtain comprising manganese-zinc ferrite
Reaction system, stir 30min after carrying medicament sulforaphen is added after cooling；Preferably, the medicine-carried system, granularity are small
In 100nm.Preferably, gamma-polyglutamic acid molecular size range is 40KD.
(4) 30min is stirred after carrying medicament sulforaphen being added after cooling；Magnet sedimentation separation after dialysis, finally freezes
Vacuum drying must load the medicine-carried system of sulforaphen.
Embodiment 3:
A kind of medicine-carried system loading sulforaphen wraps up chitosan oligosaccharide and γ-polyglutamic for manganese-zinc ferrite nano grain surface
The mass ratio of the mixture of acid, the manganese-zinc ferrite nano particle and chitosan, gamma-polyglutamic acid is 1:10:100.
The preparation method of above-mentioned medicine-carried system, step include:
1) it is 12:4:1 according to iron, manganese, zinc molar ratio, weighs FeCl3·6H2O、ZnSO4·7H2O、MnSO4·H2O is added
Isothermal reaction 1h after NaOH is added in deionized water, the agitating and heating at 95 DEG C；
2) chitosan oligosaccharide of 1/3~2/3 amount is added, is mixed, after 95 DEG C of reaction 1h, ultrasound, centrifugation, by bulky grain liquid nitrogen therein
Ball-milling treatment；Preferably, the chitosan oligosaccharide molecular size range is 1KD；
3) remaining chitosan oligosaccharide is added and 60 DEG C of γ-polyglutamic acid is reacted 1h again, be freeze-dried, obtain comprising manganese-zinc ferrite
Reaction system；Preferably, the medicine-carried system, granularity are less than 100nm.Preferably, gamma-polyglutamic acid molecular size range is
40KD。
4) 30min is stirred after carrying medicament sulforaphen being added after cooling；After magnetic fluid is passed through dialysis, magnet sedimentation
Separation, last freezing vacuum drying, must load the medicine-carried system of sulforaphen.
Comparative example 1: manganese-zinc ferrite nano particle is used alone
1) manganese-zinc ferrite nano particle is taken to be added in deionized water, after 95 DEG C of reaction 1h, ultrasound, centrifugation, by big therein
After grain cryomilling processing, 60 DEG C are reacted 1h again, the agitating and heating at 95 DEG C, isothermal reaction 1h, and carrying medicament is added after cooling
30min is stirred after sulforaphen；
2) after by magnetic fluid by dialysis, magnet sedimentation separation, last freezing vacuum drying must load the load medicine of sulforaphen
System.
Comparative example 2: chitosan oligosaccharide medicine-carried system is used alone
1) at 95 DEG C under agitating and heating, with the chitosan oligosaccharide of 1/3~2/3 amount of deionized water dissolving, ultrasound, centrifugation, will it is therein greatly
After the processing of particle cryomilling, 60 DEG C of reheating 1h of remaining chitosan oligosaccharide are added, are freeze-dried, carrying medicament trailing plants is added after cooling
30min is stirred after foretelling thionin；
4) after by chitosan oligosaccharide medicine-carried system by dialysis, freezing vacuum drying must load the medicine-carried system of sulforaphen.
Comparative example 3: chitosan oligosaccharide/manganese-zinc ferrite nano particle is used alone
1) it is 12:4:1 according to iron, manganese, zinc molar ratio, weighs FeCl3·6H2O、ZnSO4·7H2O、MnSO4·H2O is added
Isothermal reaction 1h after NaOH is added in deionized water, the agitating and heating at 95 DEG C；
2) chitosan oligosaccharide of 1/3~2/3 amount is added, mixes, after 95 DEG C of reaction 1h, ultrasound, centrifugation, by bulky grain liquid nitrogen ball therein
Mill processing；
3) remaining 60 DEG C of chitosan oligosaccharide are added and react 1h again, be freeze-dried, obtain the reaction system comprising manganese-zinc ferrite；
4) 30min is stirred after carrying medicament sulforaphen being added after cooling；After magnetic fluid is passed through dialysis, magnet sedimentation point
From last freezing vacuum drying must load the medicine-carried system of sulforaphen.
Implementation result example
Drug-loading system is prepared in embodiment 1-3 and comparative example 1-3 and is analyzed as follows table.
Table 1 embodiment 1-3 and comparative example 1-3 is prepared drug-loading system and carries medicine situation and network analysis
| Project | Partial size/nm | Load factor/% | Encapsulation rate/% | The sustained release time/h | Stability/day |
| Embodiment 1 | 70 | 10.26 | 24.38 | 24 | 40 |
| Embodiment 2 | 65 | 10.96 | 26.45 | 24 | 40 |
| Embodiment 3 | 49 | 11.67 | 27.25 | 24 | 40 |
| Comparative example 1 | 15 | 5.81 | 12.70 | 4 | 40 |
| Comparative example 2 | 198 | 8.56 | 17.14 | 8 | 15 |
| Comparative example 2 | 75 | 7.34 | 15.89 | 8 | 30 |
Note: the sustained release time is that drug concentration reaches effective concentration sustainable release time.
Claims (10)
1. a kind of medicine-carried system for loading sulforaphen wraps up chitosan oligosaccharide for manganese-zinc ferrite nano grain surface and γ-is poly-
The mixture of glutamic acid loads sulforaphen, which is characterized in that the manganese-zinc ferrite nano particle and chitosan, γ-are poly-
The mass ratio of glutamic acid is 1:1~20:10~200.
2. drug-loading system according to claim 1, which is characterized in that for the drug-loading system when pH is 5.5, simulation is swollen
Acid or alkali environment in oncocyte can be sustained more than for 24 hours, and preparation is higher than 90%.
3. drug-loading system according to claim 1, which is characterized in that the drug-loading system is simulated when pH is 7.4
Acid or alkali environment in human body, no slow release effect, and release rate are lower than 20%.
4. drug-loading system according to claim 1, which is characterized in that the medicine-carried system, granularity are less than 100nm.
5. drug-loading system according to claim 1, which is characterized in that the chitosan oligosaccharide molecular size range is 1KD, γ-
Polyglutamic acid molecular size range is 40KD.
6. drug-loading system according to claim 1, which is characterized in that the manganese-zinc ferrite nano particle, partial size are
10~30nm, polydispersity coefficient is below 0.2.
7. drug-loading system according to claim 1, which is characterized in that the manganese-zinc ferrite nano particle, by
FeCl3·6H2O、ZnSO4·7H2O、MnSO4·H2O is prepared according to iron, manganese, zinc molar ratio for 12:4:1.
8. drug-loading system according to claim 1, which is characterized in that the medicine-carried system of the load sulforaphen, drug
Load factor is 10.26~11.67%, and entrapment efficiency is 25.15~27.25%.
9. a kind of preparation method of the medicine-carried system of load sulforaphen described in claim 1, which is characterized in that including following
Step:
(1) FeCl is weighed according to the ratio3·6H2O、ZnSO4·7H2O、MnSO4·H2O, is added deionized water, and stirring and dissolving is added
NaOH reacts 30-90 min；
(2) chitosan oligosaccharide of 1/3~2/3 amount is added, is stirred, reacts, is centrifuged after ultrasound, by bulky grain cryomilling therein
Processing；
(3) remaining chitosan oligosaccharide and gamma-polyglutamic acid are added, is reacted；Freeze-drying, obtains the load medicine body comprising manganese-zinc ferrite
System；
(4) it is stirred after carrying medicament sulforaphen being added after cooling；Magnet sedimentation separation after dialysis, last freezing vacuum drying,
The medicine-carried system of sulforaphen must be loaded.
10. preparation method according to claim 9, which is characterized in that the reaction temperature of step (1) are as follows: 90-98 DEG C.
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| CN110403919A (en) * | 2019-08-29 | 2019-11-05 | 长江师范学院 | A kind of preparation method of rouge radish thionin capsule of nano |
| CN110403919B (en) * | 2019-08-29 | 2021-11-02 | 长江师范学院 | Preparation method of carmine sulforaphane nano microcapsule |
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