CN105056239B - The composite material and its preparation of functional mesoporous silicon dioxide carried drug and siRNA and the application in preparing anticancer drug - Google Patents
The composite material and its preparation of functional mesoporous silicon dioxide carried drug and siRNA and the application in preparing anticancer drug Download PDFInfo
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Abstract
The composite material and preparation method that a kind of functional mesoporous silicon dioxide carried drug and siRNA are disclosed the invention belongs to functional material carrying medicament and gene technology field and the application in preparing anticancer drug.The composite material is prepared by method comprising the following steps：Mesoporous silicon oxide is added in 3 mercaptopropyl trimethoxysilane solution, heating reaction, separation obtain sulfhydrylation mesoporous silicon oxide, distribute it to 2, in 2 two sulphur, two pyridine solution, heating reaction obtains the mesoporous silicon oxide of disulfide bond modification, it is added into adriamycin aqueous solution, the siRNA of sulfhydrylation is added, detaches, obtains the composite material of functional mesoporous silicon dioxide carried drug and siRNA.The composite material of the present invention is applied to prepare in anticancer drug, can significantly improve the enriching quantity of drug in the cell by drug loading to intracellular, and plays the role of blocking very well mesoporous, discharges the effect for playing cryptiogene in the cell.
Description
Technical field
The invention belongs to functional material carrying medicament and gene technology field, more particularly to a kind of functional mesoporous titanium dioxide
The composite material and preparation method and the application in preparing anticancer drug of silicon carrying medicament and siRNA.
Background technology
Recent year anticancer market is in growing situation, and anticancer drug has leaped second in hospital administration
Position, is only below anti-infectious agent.Currently, the means for the treatment of cancer include mainly surgical operation therapy, radiotherapy and chemicals
Treatment, but these therapies while killing cancer cell again easy damaged normal cell and immunocyte, lack selectively,
And leading to a series of toxic side effect, some more serious adverse reactions can also threaten the life of patient.
Currently, the treatment of part and diffused cancer relies primarily on chemotherapy.However, chemotherapeutics used in treating cancer is universal
In the presence of following limitation：(1) lack targeting：Usually used anticancer drug has universal cytotoxicity, lacks to cancer cell
Selectivity and targeting, leading to normal cell, there is also non-specific endocytosis, damage the proliferation of normal cell, tight to generate
The side effect of weight, therefore the shortcomings of drug shows low therapeutic index, curative effect unobvious；(2) multidrug resistance：Multidrug resistance
So that the anticancer drug entered in cancer cell is constantly pumped out cell, increases pump output, Intracellular drug is caused to reduce, reduce
Effect of the anticancer drug to cancer cell；(3) bioavailability is low：Most of anticancer drug has the work for inhibiting cancer cell well
With, but lower bioavailability largely affects the clinical effectiveness of drug.
Due to drugloading rate height, biological effect is strong, can promote the advantages that cell endocytic is to avoid multidrug resistance, in recent years
The treatment for developing into cancer of Nano medication delivery system, especially nano target medicine delivery system provides a kind of before having very much
The approach of scape.Ideal nano target medicine delivery system should have：(1) the easy functionalization of material surface；(2) high cell-specific
Property and effective cell endocytic；(3) ability of low early seepage and lasting controlled release；(4) carrier itself low toxicity or biology
Compatibility is good；(5) drug can be loaded into carrier and be protected by carrier；(6) dispersibility that carrier has had in Physiological Medium；
(7) carrier is seldom to protein adsorption, does not interfere with effect of the targeting ligand to receptor targeted；(8) carrier will not be in devices such as kidney, livers
Official gathers, and can gradual catabolism.At present applied to nano target medicine delivery system include micro emulsion, polymer micelle,
Liposome and vesica etc. change in the outside stimulus lower structure such as temperature, pH and realize drug controlled release.All due to them
Belong to soft material scope, the structural instability in aqueous medium can not prevent targeted prodrug object from leaking, and lead to not realize effective
Conveying and controlled release.Therefore people carry out in terms of being used for drug conveying and release using the material of stable structure in recent years
Many researchs.In these materials, silicon materials are used for various medicines since good biocompatibility, structure and surface nature are stable
The conveying of object and controlled release research.In addition, silicon also be used to increase the biology of other delivery vehicles such as magnetic nano-particle, polymer
Compatibility.In silicon materials family, mesoporous silicon oxide has evolved into most important and most promising a kind of drug conveying and carries
Body.
SiRNA is the ribonucleotide of one section of particular sequence, can be in the table for being transfected into intracellular rear silence corresponding gene
It reaches, achievees the effect that gene interferes (RNAi).However, previous report shows that free siRNA cannot be introduced into cell, need
It is chemically modified or nano particle load can just be efficiently entering cells play effect.
Adriamycin (Dox) is a kind of efficient antibiotic for killing cancer cell, is now widely used in the treatment of cancer.But
Due to not having selectivity, in treatment of cancer larger side effect inhibit its application.The present invention utilizes mesoporous silicon oxide
Plastic packaging Dox, and carry out mesoporous closure using other substances and can effectively load Dox, it is using EPR effects that medicine-carried system is rich
Collect cancer region and cause cell endocytic, drug release reaches best anticancer effect and minimizes side effect in the cell.By Dox
After in plastic packaging to mesoporous silicon oxide, siRNA is connected in meso-porous titanium dioxide silicon face using disulfide bond, is blocked using three-dimensional effect
It is mesoporous, form function mesoporous silicon oxide medicine-carried system.So far the functional mesoporous silica medicine-carried of the present invention is found no
System report use for cancer treatment.
Invention content
In order to overcome the shortcomings and deficiencies of the prior art described above, the primary purpose of the present invention is that providing a kind of functionalization Jie
The composite material of hole silicon dioxide carried drug and siRNA.
Another object of the present invention is to provide the compound of a kind of above-mentioned functional mesoporous silicon dioxide carried drug and siRNA
The preparation method of material.
Still a further object of the present invention is to provide the composite material of above-mentioned functional mesoporous silicon dioxide carried drug and siRNA
Application in preparing anticancer drug.
The purpose of the present invention is realized by following proposal：
A kind of composite material of functional mesoporous silicon dioxide carried drug and siRNA, by method comprising the following steps
It is prepared：
Mesoporous silicon oxide is added in 3- mercaptopropyl trimethoxysilane solution, heating reaction, separation obtains sulfhydrylation
Mesoporous silicon oxide distributes it in 2,2-, bis- sulphur, two pyridine solution, and heating reaction obtains the mesoporous dioxy of disulfide bond modification
SiClx is added into adriamycin aqueous solution, adds the siRNA of sulfhydrylation, and it is negative to obtain functional mesoporous silica for separation
Carry the composite material of drug and siRNA.
The molar ratio of element silicon is preferably 2 in 3- mercaptopropyl trimethoxysilanes and mesoporous silicon oxide used:1~4:1.
The molar ratio of bis- sulphur of 2,2-, two pyridine used and element sulphur in sulfhydrylation mesoporous silicon oxide is preferably 2:1~1:1.
The molar ratio of siRNA used and element sulphur in the mesoporous silicon oxide of disulfide bond modification are preferably 1:2~1:1.
The concentration of the adriamycin aqueous solution is preferably 0.8~1g/L.
The mesoporous silicon oxide is the mesoporous silicon oxide being prepared using standard law.
The concentration of the 3- mercaptopropyl trimethoxysilane solution is preferably 1~1.2Mol/L.
The 3- mercaptopropyl trimethoxysilane solution is preferably 3- mercaptopropyl trimethoxysilane toluene solutions.
The concentration of bis- sulphur of the 2,2-, two pyridine solution is preferably 0.1~0.12Mol/L.
Bis- sulphur of 2,2-, two pyridine solution is preferably bis- sulphur of 2,2-, two pyridine ethanol solution.
The described heating reaction reaction 12~for 24 hours preferably at 80~83 DEG C.
The isolated product washs it is preferable to use deionized water and in 50 DEG C of drying of vacuum.
The composite material of functional mesoporous silicon dioxide carried drug and siRNA that aforementioned present invention is prepared has excellent
The bioactivity of different kill cancer cell, can be applied to prepare in anticancer drug.
The present invention mechanism be：
Jie that the functional mesoporous silicon dioxide carried drug of the present invention and the composite material of siRNA are acted on carrying medicament
Hole silica is core, and surface connects siRNA by disulfide bond and carries out mesoporous closure, while playing carrying medicament and siRNA
Effect.The functional mesoporous silicon dioxide carried drug of the present invention and the composite material of siRNA can be good at drug loading
Into intracellular, the enriching quantity of drug in the cell is significantly improved.Also, being covalently keyed siRNA in composite material can be very
Play the role of well blocking mesoporous and the effect for playing cryptiogene can be discharged in the cell.The preparation method of the present invention is simple, obtains
To material can directly preserve and use.
The present invention compared with the existing technology, has the following advantages and advantageous effect：
(1) composite material of functional mesoporous silicon dioxide carried drug of the invention and siRNA, which not only have, kills cancer
The effect of cell, and have the function of causing cancer cell-apoptosis, it is suitable for preparing inhibition cancer cell drug.
(2) functional mesoporous silicon dioxide carried drug of the invention is connected with the composite material of siRNA using disulfide bond
SiRNA is played in mesoporous silicon oxide and is blocked mesoporous effect.It can be to high expression paddy Guang in cancer cell after cellular uptake
Sweet peptide response causes disulfide bonds while releasing adriamycin and siRNA.
(3) composite material of functional mesoporous silicon dioxide carried drug of the invention and siRNA can significantly improve Ah
Mycin cell accumulation, especially in the enrichment of nuclear area.Covalent bond siRNA can significantly improve gene silencing effect
Rate achievees the effect that silence target gene.
Description of the drawings
Fig. 1 is perspective Electronic Speculum (TEM) figure of the mesoporous silicon oxide of embodiment 1.
Fig. 2 is the perspective Electronic Speculum of the functional mesoporous silicon dioxide carried drug of embodiment 1 and the composite material of siRNA
(TEM) figure.
Fig. 3 is the functional mesoporous silicon dioxide carried drug of embodiment 2 and the composite material cytotoxicity figure of siRNA.
Wherein, MSNs-SS-Py is the mesoporous silicon oxide of functionalization, and DOX is adriamycin, and MSNs@DOX are the function of loading adriamycin
Change mesoporous silicon oxide, MSNs-SS-siRNA@DOX are the composite material for loading adriamycin and siRNA.
Fig. 4 is the composite material drug-rich figure in the cell of functional mesoporous silicon dioxide carried drug and siRNA.Its
In, Free DOX are free adriamycin, and MSNs-SS-siRNA@DOX are the composite material for loading adriamycin and siRNA.
Fig. 5 is the design sketch of the composite material cryptiogene expression of functional mesoporous silicon dioxide carried siRNA.Wherein,
MSNs is mesoporous silicon oxide, and MSNs-SS-siRNA is that mesoporous silicon oxide loads siRNA, and MSNs-SS-NCsiRNA is mesoporous
Silicon dioxide carried out of order siRNA, Free siRNA are free siRNA, and Lipo2000+siRNA is business liposome 2000
SiRNA is loaded, as positive control.
Specific implementation mode
With reference to embodiment and attached drawing, the present invention is described in further detail, but embodiments of the present invention are unlimited
In this.
As long as it is pure above that the purity of the raw materials used in the present invention reaches chemistry, source is commercially available.
Embodiment 1：The preparation of the composite material of functional mesoporous silicon dioxide carried drug and siRNA
The preparation of mesoporous silicon oxide (MSNs)：Cetyl trimethylammonium bromide (CTAB, 500mg) is dissolved in distillation
Water (250mL), is then added NaOH aqueous solutions (1.75mL, 2Mol/L), and mixed solution is heated to 80 DEG C with vigorous stirring.When
After temperature is stablized, ethyl orthosilicate (TEOS, 2mL) is slowly added to mixed solution.Nano-particle leaves the heart by 10000 after 2h
It collects within 3 minutes, with ethyl alcohol and distills water washing three times.To remove template, the nano-particle of collection is resuspended in ethyl alcohol
(80mL) contains in concentrating hydrochloric acid (4mL, 37%), flows back at 80 DEG C for 24 hours, and leave the heart by 10000 collects for 3 minutes, uses ethyl alcohol
With distillation water washing three times, it is dried in vacuum overnight at 50 DEG C of nano-particle.Its pattern passes through TEANAI-10 type transmission electron microscopies
Mirror (TEM) is observed, as shown in Figure 1.Its grain size is in 80nm or so.
The above-mentioned MSNs (50mg) being prepared is dissolved in the 3- mercaptopropyi trimethoxy silicon of ethyl alcohol (20mL) and 1.8mL
In alkane (MPTMS) mixed solution in a nitrogen atmosphere 50 DEG C stirring for 24 hours.Then, particle by be collected by centrifugation (10000 turns,
5min), sulfhydrylation mesoporous silicon oxide (MSNs-SH) is obtained.By mesoporous silicon oxide (MSNs-SH) (60mg) weight of sulfhydrylation
New to be dispersed in 5mL methanol (containing 0.1g 2,2- dithiodipyridines), mixture is stirred at room temperature for 24 hours, and nano-particle passes through
It is collected by centrifugation, with ethyl alcohol and water washing three times, is dried in vacuum overnight at 50 DEG C, obtain the mesoporous silicon oxide of disulfide bond modification
Nano-particle.
The adriamycin aqueous solution for preparing 1g/L, the mesoporous silicon dioxide nano particle that above-mentioned disulfide bond is modified sub (50mg) point
It is scattered in solution, ultrasonic 12h, particle is by being collected by centrifugation (10000 turns, 5min).Meanwhile by the mercapto-modified (Shanghai siRNA
Lucky horse biology Co., Ltd) and dithiothreitol (DTT) (DTT) incubation 2h, the disulfide bond formed between siRNA is broken, it is then excessive
DTT is sloughed using glucan column.The nano-particle for loading adriamycin is resuspended in PBS buffer solution (pH 7.4), is incubated at 4 DEG C
Educate 2 times of equivalent siRNA-SH 48h, leaving the heart 5 minutes 10000 collects, obtain functional mesoporous silicon dioxide carried drug and
The composite material of siRNA.Its pattern is observed by TEANAI-10 types transmission electron microscope (TEM), as shown in Figure 2.Its grain size
In 100nm or so, some features of mesoporous silicon oxide, such as cavernous structure and spherical morphology are still kept.
Embodiment 2：The composite material of functional mesoporous silicon dioxide carried drug and siRNA are as the external of anticancer drug
Experiment
This experimental selection human breast cancer cell (MCF-7 matches neat (Shanghai) bioengineering Co., Ltd) is situated between as functionalization
The silica medicine-carried system anticancer experimental subjects in hole.
MTT test methods：With 0.25% trypsin digestion and cell 5 minutes, cell is gently blown and beaten with suction pipe into suspension
Cell suspension in device centrifuge tube takes 10 μ L cell suspending liquids to use tricks rolling counters forward viable count, and adjustment viable cell concentrations are 5 ×
103/ mL is added on 96 well culture plates, per 100 μ L of hole, after cultivating 24 hours, is separately added into what various concentration embodiment 1 was prepared
Composite material is placed in 37 DEG C, volume fraction 5%CO2Culture 24 hours.4 20 holes μ L/ of hours addition MTT before the end, 4
Liquid is discarded supernatant after hour, 100 holes μ L/ DMSO are added, is vibrated 15 minutes or so, and microplate reader measures OD values, wavelength 450nm.
Survival rate is calculated according to the following formula, evaluation drug kills cancer cell effect.Experimental result is as shown in Figure 3.
Survival rate %=medicine feeding holes mean OD value/control wells mean OD value × 100%
Embodiment 3：The composite material of functional mesoporous silicon dioxide carried drug and siRNA in the cell make by drug-rich
With
By the MCF-7 cells in logarithmic phase with after 0.25% 3~5min of trypsin digestion cell, after centrifugation, use
Its mixing is inoculated with 1 × 10 by culture medium4A cell adds the culture of 2mL in the little groove of laser co-focusing ware, after 1h
Liquid, 5%CO2, cultivate for 24 hours in 37 DEG C of incubator.It is separately added into the 10 μ g/mL of composite material and phase that embodiment 1 is prepared
Adriamycin processing the cell 1h and 3h of equivalent.The culture medium in ware is then sucked, after then being rinsed three times with PBS, adds 1mL
PBS infiltrating cells, taken pictures using confocal laser scanning microscope.As shown in figure 4, compared to free adriamycin, this hair
Adriamycin in bright composite material can significantly improve the enriching quantity of adriamycin in the cell, while in the enrichment of nuclear area
Amount also significantly improves, this is exactly the region that adriamycin plays drug effect.
Embodiment 4：The efficiency of the composite material cryptiogene expression of functional mesoporous silicon dioxide carried siRNA
By the MCF-7 cells in logarithmic phase with after 0.25% 3~5min of trypsin digestion cell, after centrifugation, use
Its mixing, adjustment viable cell concentrations are 5 × 10 by culture medium3/ mL is added in 6 orifice plates, 5%CO2, cultivate in 37 DEG C of incubator
24h.After various drug incubations are added for 24 hours, directly use RIPA lysates (containing PMSF) by cell cracking on ice, place on ice
After 30min, 4 DEG C, supernatant is drawn after 10min centrifugations by 12000rpm.Total protein is carried out with BCA kits after quantifying, and takes 1.5mL
Total protein boils 5min together with sample-loading buffer, then freezes in -80 DEG C, is used for western blot.Western blot
It is briefly as follows：Albumen loading to SDS polyacrylamide gels is subjected to electrophoretic separation albumen.Wherein resolving gel concentration 10% is dense
Contracting gum concentration 5%.Then albumen is subjected to transferring film (wet turn), transferring film condition is constant current 250mA, 2h.And then by film in TBST
Cleaning 3 times, each 5min.Then 5% skimmed milk power is added and carries out closing 1h.Film and 4 DEG C of solutions of primary antibody are educated overnight, by TBST
Cleaning 3 times, each 10min.Then film and HRP label secondary antibodies are incubated at room temperature 1h, wash paint 3 times by TBST, each 10min
Afterwards, ECL colour developings are carried out.As shown in figure 5, functional mesoporous silicon dioxide carried siRNA can make siRNA enter cancer cell,
The shortcomings that overcoming siRNA to treat.Compared to other control groups, the siRNA of nano load has better silence target gene
The effect of Bcl-2 expression；Meanwhile the expression of the GAP-associated protein GAP pro-caspase-9 of Bcl-2 expression accesses is also affected, into
One step shows that functional mesoporous silica medicine-carried system has the effect of good silence target gene.
Wherein, MSNs-SS-NCsiRNA is that mesoporous silicon oxide loads out of order siRNA, and preparation method is：It will be out of order
SiRNA (Shanghai Ji horse biology Co., Ltd) is incubated 2h with dithiothreitol (DTT) (DTT), breaks the disulfide bond formed between siRNA,
Then excessive DTT is sloughed using glucan column.The mesoporous silicon dioxide nano for the disulfide bond modification that embodiment 1 is prepared
Particle (50mg) is suspended in PBS buffer solution (pH 7.4), and the treated siRNA 48h of 2 times of equivalents are incubated at 4 DEG C,
10000 leave the heart collects for 5 minutes, obtains mesoporous silicon oxide and loads out of order siRNA.Due to the siRNA be it is out of order, cannot
To targeted silent corresponding gene, therefore do not have activity.
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, it is other it is any without departing from the spirit and principles of the present invention made by changes, modifications, substitutions, combinations, simplifications,
Equivalent substitute mode is should be, is included within the scope of the present invention.
Claims (10)
1. a kind of composite material of functional mesoporous silicon dioxide carried drug and siRNA, it is characterised in that by including following step
Rapid method is prepared：
Mesoporous silicon oxide is added in 3- mercaptopropyl trimethoxysilane solution, it is mesoporous to obtain sulfhydrylation for heating reaction, separation
Silica distributes it in 2,2-, bis- sulphur, two pyridine solution, and heating reaction obtains the meso-porous titanium dioxide of disulfide bond modification
Silicon is added into adriamycin aqueous solution, adds the siRNA of sulfhydrylation, and separation obtains functional mesoporous silicon dioxide carried
The composite material of drug and siRNA.
2. the composite material of functional mesoporous silicon dioxide carried drug and siRNA according to claim 1, feature exist
In：The molar ratio of element silicon is 2 in 3- mercaptopropyl trimethoxysilanes and mesoporous silicon oxide used:1~4:1.
3. the composite material of functional mesoporous silicon dioxide carried drug and siRNA according to claim 1, feature exist
In：The molar ratio of bis- sulphur of 2,2-, two pyridine used and element sulphur in sulfhydrylation mesoporous silicon oxide is 2:1~1:1.
4. the composite material of functional mesoporous silicon dioxide carried drug and siRNA according to claim 1, feature exist
In：The molar ratio of siRNA used and element sulphur in the mesoporous silicon oxide of disulfide bond modification are 1:2~1:1.
5. the composite material of functional mesoporous silicon dioxide carried drug and siRNA according to claim 1, feature exist
In：A concentration of 0.8~1g/L of the adriamycin aqueous solution.
6. the composite material of functional mesoporous silicon dioxide carried drug and siRNA according to claim 1, feature exist
In：A concentration of 1~1.2mol/L of the 3- mercaptopropyl trimethoxysilane solution.
7. the composite material of functional mesoporous silicon dioxide carried drug and siRNA according to claim 1, feature exist
In：A concentration of 0.1~0.12mol/L of bis- sulphur of the 2,2-, two pyridine solution.
8. the composite material of functional mesoporous silicon dioxide carried drug and siRNA according to claim 1, feature exist
In：The 3- mercaptopropyl trimethoxysilane solution is 3- mercaptopropyl trimethoxysilane toluene solutions；The 2,2- bis-
Two pyridine solution of sulphur is bis- sulphur of 2,2-, two pyridine ethanol solution.
9. the composite material of functional mesoporous silicon dioxide carried drug and siRNA according to claim 1, feature exist
In：Reaction 12~for 24 hours is reacted at 80~83 DEG C in the heating.
10. according to the composite wood of claim 1~9 any one of them functional mesoporous silicon dioxide carried drug and siRNA
Expect the application in preparing anticancer drug.
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| CN105343895B (en) * | 2015-12-04 | 2019-10-15 | 福州大学 | A kind of load ursolic acid/siRNA fluorescence mesoporous silicon oxide-hyaluronic acid of dual-target and application |
| CN105350113B (en) * | 2015-12-10 | 2018-04-06 | 济南大学 | A kind of preparation method and products obtained therefrom of azotized carbon nano fiber |
| KR20210015717A (en) * | 2019-07-31 | 2021-02-10 | 주식회사 레모넥스 | Anticancer drug and preparing method for porous silica particle |
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| CN102327622A (en) * | 2011-09-08 | 2012-01-25 | 上海交通大学 | Method for loading siRNA (small interfering Ribonucleic Acid) by using mesoporous silicon dioxide nanoparticles |
| CN104013965A (en) * | 2014-05-06 | 2014-09-03 | 重庆大学 | Method for preparing meso-porous silicon nano medicine carrier with cell specificity target, reduction responsiveness and triple anticancer treatment effects |
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| US20120207795A1 (en) * | 2010-07-13 | 2012-08-16 | The Regents Of The University Of California | Cationic polymer coated mesoporous silica nanoparticles and uses thereof |
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| CN102327622A (en) * | 2011-09-08 | 2012-01-25 | 上海交通大学 | Method for loading siRNA (small interfering Ribonucleic Acid) by using mesoporous silicon dioxide nanoparticles |
| CN104225599A (en) * | 2013-06-14 | 2014-12-24 | 吉林大学 | Asymmetric magnetic mesoporous silica rod supporting chemotherapeutic and gene drugs and application thereof to tumor diagnosis and treatment |
| CN104013965A (en) * | 2014-05-06 | 2014-09-03 | 重庆大学 | Method for preparing meso-porous silicon nano medicine carrier with cell specificity target, reduction responsiveness and triple anticancer treatment effects |
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