CN106924215A - Carry curcumin enoxolone modification mesoporous silicon dioxide nano particle and preparation method thereof - Google Patents
Carry curcumin enoxolone modification mesoporous silicon dioxide nano particle and preparation method thereof Download PDFInfo
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- CN106924215A CN106924215A CN201611010584.6A CN201611010584A CN106924215A CN 106924215 A CN106924215 A CN 106924215A CN 201611010584 A CN201611010584 A CN 201611010584A CN 106924215 A CN106924215 A CN 106924215A
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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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/51—Nanocapsules; Nanoparticles
- A61K9/5107—Excipients; Inactive ingredients
- A61K9/5115—Inorganic compounds
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/12—Ketones
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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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/51—Nanocapsules; Nanoparticles
- A61K9/5107—Excipients; Inactive ingredients
- A61K9/5123—Organic compounds, e.g. fats, sugars
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Abstract
The invention belongs to field of pharmaceutical preparations.Curcumin enoxolone modification mesoporous silicon dioxide nano particle and preparation method thereof is carried the present invention relates to one kind.The load curcumin enoxolone modification mesoporous silicon dioxide nano particle that the present invention is prepared can realize that active targeting is administered.Said preparation drugloading rate is high, preparation process is simple, low production cost, it is easy to industrialized production, can reduce side effects of pharmaceutical drugs while curative effect of medication is strengthened.
Description
Technical field
Curcumin enoxolone modification mesoporous silicon dioxide nano particle and preparation method thereof is specifically related to carried herein, belongs to medicine
Thing formulation art.
Background technology
Liver cancer is a kind of common cancer, and in the whole world, especially developing country has the incidence of disease higher and death
Rate.Chemotherapy is still one of primary treatments of cancer so far.However, due to a lack of selection index system, chemotherapeutics is killing cancer
While disease cell, substantial amounts of normal cell is also killed.Therefore, traditional chemotherapy has serious side effect, such as serious
System toxicity, complication, compliance is poor and easily produces drug resistance.
Administration nano-drug administration system because its numerous advantage be always cancer target administration aspect research focus.Nanometer administration system
System can improve the pharmacodynamics and pharmacokinetics feature of medicine, while medication effect is remarkably reinforced, maximized reduction
Side effects of pharmaceutical drugs.Mesoporous silicon dioxide nano particle because of the surface with easily modification and functionalization, huge surface area and higher
Pore volume, the features such as unique meso-hole structure and good stability, become that Tumor Targeting Drug Delivery System aspect is new to grind
Study carefully focus.
Curcumin is the extract in the rhizome of plant turmeric.Modern pharmacology research finds that curcumin has anti-inflammatory, resists
Liver fibrosis, anti-angiogenesis and numerous pharmacological activities such as antitumor.However, because curcumin has slightly water-soluble, low life
The features such as thing availability and big dosage, its clinical practice is limited by very large.In the present invention, carried by by curcumin
Enter to drugloading rate mesoporous silicon dioxide nano particle high it is mesoporous in, be expected to solve the above problems.
Enoxolone is extracted from the rhizome of Radix Glycyrrhizae, among candy and tinned food is widely used in as sweetener.
In recent years research finds that there is special enoxolone acceptor in liver, these acceptors can specifically bind with enoxolone,
And study and find expression quantity of the enoxolone acceptor in tumor cell of liver apparently higher than in its around normal liver cell
Expression quantity.Separately having substantial amounts of research confirms, the nanoparticle of surface modification enoxolone can be thin with specific targeting liver tumour
Born of the same parents.
In patent of the present invention, by the method described in patent of the present invention, can will be sweet by way of Covalent bonding together
Careless hypo acid modification is on the surface of mesoporous silicon dioxide nano particle.The enoxolone modification mesoporous silicon dioxide nano particle for preparing
With huge specific surface area, pore volume and adjustable particle diameter very high.The nanoparticle has load higher to curcumin
Dose.Load curcumin enoxolone modification mesoporous silicon dioxide nano particle prepared by the present invention enters body circulation through tail vein injection
Afterwards, it is possible to use the EPR effects of tumor blood vessels reach liver neoplasm tissue through tumor vessel.Reach the load of tumor tissues
Curcumin enoxolone modification mesoporous silicon dioxide nano particle can be swollen by the enoxolone molecule of its surface modification and liver
The enoxolone acceptor on oncocyte surface realizes that receptors ligand specifically binds, and is then entered by receptor-mediated endocytosis mechanism
Enter inside tumor cells, the medicine curcumin entrained by it is discharged immediately, finally realize liver tumor cells specific target
To administration.
In sum, the load curcumin enoxolone modification mesoporous silicon dioxide nano particle that prepared by the present invention is improving difficult
The solubility of soluble drug is low and while the characteristic such as bioavilability, it is possible to achieve liver tumor cells are selectively targeted to be given
Medicine, while the side effect that medicine is brought is reduced, greatly strengthens the therapeutic action of medicine.
The content of the invention
The problems such as it is an object of the invention to be directed to low current therapies drug targeting efficiency and big toxicity, there is provided one kind carries ginger
Flavine enoxolone modifies mesoporous silicon dioxide nano particle.Load curcumin enoxolone modification meso-porous titanium dioxide prepared by the present invention
Silicon nanoparticle have prepare it is simple, the advantages of low cost and good Targeting Effect.
The purpose of the present invention is realized by following technical solution：
Step 1：Weigh cetyl trimethylammonium bromide (CTAB) and NaOH (NaOH) is dissolved in 80 DEG C of deionization
In water.Draw tetraethyl orthosilicate (TEOS) to be added drop-wise in above-mentioned solution, constant temperature stirring reaction 3h.6% methanol hydrochloride solution (v/v)
Backflow washes away template CTAB, is collected by centrifugation, and obtains mesoporous silicon dioxide nano particle.
Step 2：Use mesoporous silicon dioxide nano obtained in 3- aminopropyl triethoxysilanes (APTES) modification step 1
Grain, obtains amido modified mesoporous silicon dioxide nano particle.
Step 3：Weigh enoxolone, activation of catalyst, the enoxolone active ester for being activated.
Step 4：The step of amido modified mesoporous silicon dioxide nano particle and recipe quantity that the step of weighing recipe quantity 2 obtains
3 obtain enoxolone active ester, are scattered in the anhydrous dimethyl sulfoxide of recipe quantity, heating stirring reaction, obtain enoxolone and repair
Decorations mesoporous silicon dioxide nano particle.
Step 5：Enoxolone modification mesoporous silicon dioxide nano particle obtained in the curcumin and step 3 of recipe quantity is weighed,
It is dissolved or dispersed in the ethanol of recipe quantity, revolving removes ethanol, is dried to obtain load curcumin enoxolone and modifies mesoporous dioxy
SiClx nanoparticle.
Brief description of the drawings
Fig. 1 is that the enoxolone prepared by present example 1 modifies mesoporous silicon dioxide nano particle (A), amido modified Jie
The FTIR spectrum figure of hole silica dioxide nano particle (B) and mesoporous silicon dioxide nano particle (C)
Fig. 2 is that mesoporous silicon dioxide nano particle (A) and enoxolone prepared by the embodiment of the present invention 1 modify mesoporous dioxy
The transmission plot of SiClx nanoparticle (B), scale is 100nm in figure
Fig. 3 is bulk drug curcumin (A) in the embodiment of the present invention 1, carries curcumin mesoporous silicon dioxide nano particle (B) and carries
The HepG2 cellular uptake figures of curcumin enoxolone modification mesoporous silicon dioxide nano particle (C).
Specific embodiment
In order to further illustrate the present invention and its advantage, following specific embodiment is given, it should be understood that these embodiments
It is only limitted to the limitation illustrated not as the scope of the invention.
Embodiment 1
1. the preparation of mesoporous silicon dioxide nano particle
1.0 parts of CTAB and 0.28 part of NaOH are weighed respectively to be dissolved in 80 DEG C of 480 parts of deionized waters, are drawn 5 parts of TEOS and are added dropwise
To in above-mentioned solution, constant temperature mechanical agitation 3h is collected by centrifugation product.6% methanol hydrochloride solution (v/v) backflow is washed away in product
Template CTAB, centrifuge washing collects product, dries, and blank mesoporous silicon dioxide nano particle is obtained.
2. the preparation of amido modified mesoporous silicon dioxide nano particle
Weigh 0.4 part of blank mesoporous silicon dioxide nano particle to be added in 25 parts of methyl alcohol, ultrasonic disperse, in above-mentioned solution
1.5 parts of APTES is added dropwise, at room temperature after stirring reaction 24h, absolute ethanol washing for several times, is collected by centrifugation product, dries, obtain
Amido modified mesoporous silicon dioxide nano particle.
3. enoxolone modifies the preparation of mesoporous silicon dioxide nano particle
1.0 parts of enoxolones are taken respectively, and 0.52 part of NHS, 0.94 part of DCC and 0.5 part of triethylamine is dissolved in 20 parts of anhydrous dimethyls
In sulfoxide, 25 DEG C of lucifuge stirring reaction 24h.Reaction is filtered after terminating, ether washing, is dried to obtain enoxolone active ester.
0.5 part of amido modified mesoporous silicon dioxide nano particle and 0.3 part of enoxolone active ester are weighed, 20 parts of nothings are added to
In water dimethyl sulfoxide, 60 DEG C of lucifuge stirring reaction 24h.Centrifuge washing, collects, and obtains enoxolone modification mesoporous silicon oxide and receives
The grain of rice.
Enoxolone modification mesoporous silicon dioxide nano particle and the mesoporous silicon oxide prepared above that will be prepared
Nanoparticle and amido modified mesoporous silicon dioxide nano particle are vacuum dried, and send Fourier infrared detection, and the spectrogram for obtaining is shown in figure
1.Three samples occur in that the characteristic absorption peak of mesoporous silicon dioxide nano particle, and representative several characteristic absorption peaks are such as
Under：1076cm-1It is the stretching vibration peak of Si-O-Si, 470cm-1For the bending of Si-O-Si shakes peak, 960cm-1It is Si-OH's
Stretching vibration peak.Compared to the infrared spectrogram of blank mesoporous silicon dioxide nano particle, amido modified mesoporous silicon dioxide nano particle
Spectrogram is in 2922cm-1And 2855cm-1Place occurs in that two obvious new absworption peaks, and the two absworption peaks are amido modified Jie
C-H stretching vibration peaks in the silica dioxide nano particle propyl group of hole, the appearance of the two new absworption peaks demonstrates amido modified mesoporous
The successful preparation of silica dioxide nano particle.In addition, comparing blank mesoporous silicon dioxide nano particle and amido modified meso-porous titanium dioxide
The infared spectrum of silicon nanoparticle, enoxolone modifies mesoporous silicon dioxide nano particle in 1700cm-1, 1606cm-1And 1447cm-1
Place occurs in that new absworption peak, 1700cm-1And 1447cm-1It is the characteristic absorption peak of amido link, 1606cm-1It is speculated as Radix Glycyrrhizae time
The stretching vibration peak of carbon carbon unsaturated double-bond in acid molecule, the appearance at these peaks successfully demonstrates enoxolone and modifies mesoporous dioxy
The successful preparation of SiClx nanoparticle.
The enoxolone modification mesoporous silicon dioxide nano particle and blank mesoporous silicon dioxide nano particle that will be prepared into are made
Transmission microscopy observation is made in the aqueous dispersions of suitable concn, censorship, as a result such as Fig. 2.It can be seen that enoxolone is modified
Mesoporous silicon dioxide nano particle and blank mesoporous silicon dioxide nano particle size are homogeneous, and shape is in similar round, and particle diameter distribution exists
110nm or so.Compared with blank mesoporous silicon dioxide nano particle, enoxolone modification mesoporous silicon dioxide nano particle surface has one
Kind similar membranoid substance, indirect proof enoxolone modifies the successful preparation of mesoporous silicon dioxide nano particle.
4. the preparation that curcumin enoxolone modifies mesoporous silicon dioxide nano particle is carried
Weigh 0.16 part of enoxolone modification mesoporous silicon dioxide nano particle and 0.04 part of curcumin is scattered in 20 parts of nothing
In water-ethanol, ultrasonic disperse, rotary evaporation removes ethanol, and 50% ethanol solution (40 parts) washes away unnecessary medicine, obtains carrying ginger
Flavine enoxolone modifies mesoporous silicon dioxide nano particle.Weigh a certain amount of load curcumin enoxolone modification meso-porous titanium dioxide
Silicon nanoparticle, ethanol dissolves medicine therein, dilutes suitable multiple, takes determined by ultraviolet spectrophotometry its drugloading rate to be
8.78 ± 1.24%.
5. cellular uptake experiment
The invention institute is investigated from the cells of HepG 2 (being provided by Chongqing City's biochemistry and molecule pharmacology key lab)
The cell-targeting ability for carrying curcumin enoxolone modification mesoporous silicon dioxide nano particle of preparation.Concrete operation step is as follows：
The cells of 12 orifice plate culture HepG 2 to certain concentration, per hole to certain volume various concentrations containing bulk drug curcumin,
Carry curcumin mesoporous silicon dioxide nano particle and carry the nutrient solution that curcumin enoxolone modifies mesoporous silicon dioxide nano particle, incubate
After cultivating certain hour in case, cell is collected, using Syrups by HPLC cell to the intake of medicine curcumin, as a result seen
Fig. 3.As seen from the figure, compared to bulk drug curcumin group and load curcumin mesoporous silicon dioxide nano particle group, curcumin is carried sweet
Careless hypo acid modification silica dioxide nano particle can be remarkably reinforced intake of the cell to medicine, as a result confirm the load prepared by the invention
Curcumin mesoporous silicon dioxide nano particle has good cell-targeting ability.
Claims (3)
- It is 1. a kind of to carry curcumin enoxolone modification mesoporous silicon dioxide nano particle, it is characterised in that：Described nanoparticle be Mesoporous silicon dioxide nano particle surface modification enoxolone molecule, and in enoxolone modification mesoporous silicon dioxide nano particle Curcumin has been carried in mesoporous.
- 2. a kind of curcumin enoxolone that carries as claimed in claim 1 modifies mesoporous silicon dioxide nano particle, including following systems Standby step：A () weighs 0.1-5 parts of cetyl trimethylammonium bromide (CTAB) and 0.05-0.5 parts of NaOH (NaOH) adds To in 50-500 parts of 80 DEG C of deionized waters, draw 1-10 parts of tetraethyl orthosilicate (TEOS) and be added drop-wise in above-mentioned solution, stir 0.5- 24h, 50-150 part of 6% methanol hydrochloride solution washed product, is collected by centrifugation, and obtains blank mesoporous silicon dioxide nano particle；B () claims Take the blank mesoporous silicon dioxide nano particle that 0.4 part of step (a) obtains to be scattered in 5-20 parts of methyl alcohol, draw 0.1-2 parts of 3- ammonia Propyl-triethoxysilicane (APTES) is added in above-mentioned solution, stirring reaction, and washing is collected, and obtains amido modified mesoporous two Silica nanoparticle；C () weighs 0.1-2 parts of enoxolone and 0.1-2 parts of catalyst is added in 5-30 parts of anhydrous dimethyl sulfoxide, Lucifuge is reacted, the enoxolone active ester that product is activated through filtration washing；D () weighs 0.1-2 parts of step (c) and prepares Enoxolone active ester and 0.1-2 parts of amido modified mesoporous silicon dioxide nano particle, be added to 5-30 parts of anhydrous dimethyl sulfoxide In, stirring reaction, filtration washing obtains enoxolone modification mesoporous silicon dioxide nano particle；E () weighs 0.1-1 parts of step (d) Both are added to 5-50 by enoxolone modification mesoporous silicon dioxide nano particle and 0.01-0.5 parts of the curcumin for preparing Part ethanol in, ultrasound, stirring, revolving removes ethanol, prepares load curcumin enoxolone modification mesoporous silicon oxide and receives The grain of rice.
- 3. the load curcumin enoxolone as described in claim 1 and 2 modifies mesoporous silicon dioxide nano particle, it is characterised in that：Described catalyst is N-N- HOSu NHSs (NHS), dicyclohexylcarbodiimide (DCC), 1- hydroxy benzos three Nitrogen azoles (HOBT), 1- (3- dimethylamino-propyls) -3- ethyl-carbodiimide hydrochlorides (EDCL) or thionyl chloride.
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Cited By (5)
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| CN107375214A (en) * | 2017-07-27 | 2017-11-24 | 重庆医科大学 | A kind of modified with folic acid montmorillonite nano preparation for carrying medicine and preparation method thereof |
| CN109010850A (en) * | 2018-08-01 | 2018-12-18 | 上海师范大学 | A kind of preparation method and application of the hollow mesopore silicon dioxide nano material for the glucan-modified Gd2 O3 loading curcumin |
| CN109665532A (en) * | 2018-12-04 | 2019-04-23 | 昆明理工大学 | A kind of biomass mesopore silicon dioxide nano material and preparation method thereof |
| CN110898006A (en) * | 2019-11-07 | 2020-03-24 | 莆田学院 | Drug-loaded micron mesoporous silicon, transdermal preparation thereof, preparation method and application |
| CN111273002A (en) * | 2020-02-13 | 2020-06-12 | 中国农业大学 | Microorganism detection method based on pigment and acid release response and application thereof |
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Cited By (8)
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| CN107375214A (en) * | 2017-07-27 | 2017-11-24 | 重庆医科大学 | A kind of modified with folic acid montmorillonite nano preparation for carrying medicine and preparation method thereof |
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| CN109010850A (en) * | 2018-08-01 | 2018-12-18 | 上海师范大学 | A kind of preparation method and application of the hollow mesopore silicon dioxide nano material for the glucan-modified Gd2 O3 loading curcumin |
| CN109010850B (en) * | 2018-08-01 | 2021-10-22 | 上海师范大学 | Preparation method and application of curcumin-loaded glucan-modified gadolinium-doped hollow mesoporous silica nanomaterial |
| CN109665532A (en) * | 2018-12-04 | 2019-04-23 | 昆明理工大学 | A kind of biomass mesopore silicon dioxide nano material and preparation method thereof |
| CN110898006A (en) * | 2019-11-07 | 2020-03-24 | 莆田学院 | Drug-loaded micron mesoporous silicon, transdermal preparation thereof, preparation method and application |
| CN110898006B (en) * | 2019-11-07 | 2021-11-05 | 莆田学院 | Drug-loaded micron mesoporous silicon, transdermal preparation thereof, preparation method and application |
| CN111273002A (en) * | 2020-02-13 | 2020-06-12 | 中国农业大学 | Microorganism detection method based on pigment and acid release response and application thereof |
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