CN106267230B - A kind of preparation method of the antitumor carrier of meso-porous nano of self gate of the drug of pH sensitivity - Google Patents
A kind of preparation method of the antitumor carrier of meso-porous nano of self gate of the drug of pH sensitivity Download PDFInfo
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Abstract
The invention belongs to pharmaceutical technology fields, sensitive more particularly to a kind of pH, that drug gates self, the antitumor carrier of meso-porous nano preparation method, this method comprises: ordered mesoporous silica dioxide is reacted to obtain the mesoporous silicon oxide of surface amination with the trimethoxy silane containing amino；P -carboxybenzaldehyde and amidized mesoporous silicon oxide are subjected to amidation process and obtain the mesoporous silicon oxide of surface benzaldehyde base；Broad-spectrum anti-cancer drug Doxorubicin is loaded into the mesoporous silicon oxide of benzaldehyde base under mildly acidic conditions, restore to neutrallty condition to obtain pH it is sensitive be loaded with anti-tumor drug DOX, DOX " self gate " meso-porous nano carrier.The antitumor carrier of meso-porous nano of self gate of the drug of the sensitivity of pH designed by the present invention, without complicated assistant chemical molecule as gate material, toxic side effect of the extraneous ingredients in practical tumor therapeutic procedure is advantageously reduced, the medicine-releasing performance with high efficiency and acidic cancer microenvironment sensitivity.
Description
Technical field
The invention belongs to pharmaceutical technology fields, and in particular to a kind of pH is sensitive, drug self gate, meso-porous nano is anti-
Tumour carrier
Background technique
Mesoporous silicon dioxide nano particle (MSNs) is that there is one kind high-specific surface area, macropore to hold, structure size is controllable, carries
Dose is high and has the emerging inorganic nano material of good biocompatibility.MSNs material is in drug delivery system in recent years
Application study cause extensive research, be expected to as a new generation pharmaceutical carrier.How more rationally, efficiently and delicately control
Pharmacy object is the hot and difficult issue of current research from the release in mesopore orbit.One effective drug intelligent control discharges system
It is able to guarantee that delivering drug molecule reaches target spot and can controllably discharge, therefore often requires that pharmaceutical carrier reaches lesion
Accomplish drug " zero release " before position, to reduce the toxic side effect of normal tissue.Using only blank MSNs material as medicine
Object carrier also cannot achieve intelligent control and discharge this target.Although with general inorganic nano particle, organic molecule and supermolecule
The molecular switch as " gate " such as assembly can make preferably the rate of release of drug for blocking the opening of the channel of MSNs
Adjusting.But system the problem of bringing, is equally obvious, first: these gate materials have complicated preparation process and potential
Toxic side effect.Such as inorganic nanoparticles can enter in vivo after disconnection, introduce to normal tissue and cell more bright
Aobvious heavy metal toxicity.Second: the sensitive intelligence of drug, which discharges, to be accomplished for the microenvironment of tumor locus.For example, at present
Most of sour response systems of development can only all realize the response of lower (pH<4.0) or higher (pH>11.0) pH value,
Almost without response under nearly physiological condition.Therefore, the door both with hypotoxicity but also with tumor microenvironment pH sensitive property is designed
Control switching material is of great significance for development of the mesoporous material in tumour medicine transmission system.
Summary of the invention
It is a kind of using tumor therapeutic agent itself as gate it is an object of the invention to design for above-mentioned problems faced
The mesoporous medicine-carried system of switching material.It is specific as follows: using the Metaporous silicon dioxide material of benzaldehyde functionalizing, by drug point
Sub- DOX is used as drug delivery and gate controlled switch material simultaneously, forms benzoyl by the aldehyde radical of DOX intrinsic amino and benzaldehyde
Imines covalent bond achievees the effect that DOX drug molecule " self gate (Self-gatekeeper) " (shown in Fig. 1).Moreover, by
It is broken under tumor tissues and cell weak acid environment in saccharin key, the DOX blocking effect made is eliminated, internal load
Drug molecule therefore reach the controlled release of pH responsiveness, be finally able to construct drug " self door of pH sensibility itself
Control " administration nano-drug administration system.At the same time, the mesoporous drug delivery system of drug " self gate " can neatly be applied to other tools
There are pH response medicine and mesoporous material, the alternative advantage with popularity and mesoporous material that drug molecule uses,
It has a good application prospect.
In order to achieve the above-mentioned object of the invention, the technical scheme adopted by the invention is as follows:
A kind of pH it is sensitive, drug self gate, the antitumor carrier of meso-porous nano preparation method, it is characterised in that:
The mesoporous silicon oxide and broad-spectrum anti-cancer drug Doxorubicin (DOX) for containing benzaldehyde using surface are respectively as meso-porous nano
Carrier and gate drug molecule；The saccharin for forming pH sensitivity by the aldehyde radical of DOX intrinsic amino and benzaldehyde is covalent
Key is able to achieve the controlled release of the pH triggering of drug molecule.
Preparation method includes the following steps:
(1) mesoporous silicon oxide is reacted to obtain the mesoporous dioxy of surface amination with the trimethoxy silane containing amino
SiClx；Trimethoxy silane containing amino is methacrylic acid -3- (trimethoxysilyl) propyl ester, relative to mesoporous two
The deal of silica, the trimethoxy silane dosage containing amino are 0.1-2 parts by weight；
(2) p -carboxybenzaldehyde and amidized mesoporous silicon oxide are subjected to amidation process and obtain surface benzaldehyde base
The mesoporous silicon oxide of change；The dosage of p -carboxybenzaldehyde is 0.1-4 parts by weight；Amidation reagent be EDC and NHS, EDC and
The mass ratio of NHS is 1:1- 1:2；Solvent is H2O and DMF, H2O and DMF volume ratio is 4:1-1:4, reaction time 12-48
Hour；
(3) broad-spectrum anti-cancer drug Doxorubicin (DOX) is loaded into mesoporous the two of benzaldehyde base under mildly acidic conditions
Silica restores to realize DOX sealing of hole to neutrallty condition, and sensitive self gate for being loaded with anti-tumor drug DOX of pH can be obtained
Meso-porous nano carrier.
The mesoporous silicon oxide of step (1) is based on ordered mesopore silicon dioxide nano material, average grain diameter 50-300
Nm, 2.4-3.5 nm of aperture, 400-1200 m of specific surface2/g.It is anti-for the wide spectrum containing amino group to gate drug molecule
Tumour medicine Doxorubicin (DOX).
The solutions of weak acidity that gate drug molecule DOX is loaded in step (3) is pH 2-6.8；Gate drug molecule
(DOX) condition of sealing of hole is to impregnate 10min-12h in the neutrality of pH 7.4-12 or alkaline solution.
A kind of pH it is sensitive, drug self gate, the antitumor carrier of meso-porous nano preparation method, it is characterised in that:
The mesoporous silicon oxide and broad-spectrum anti-cancer drug Doxorubicin (DOX) for containing benzaldehyde using surface are respectively as meso-porous nano
Carrier and gate drug molecule；
Preparation method includes the following steps:
(1) mesoporous silicon oxide is reacted to obtain the mesoporous dioxy of surface amination with the trimethoxy silane containing amino
SiClx；Trimethoxy silane containing amino is methacrylic acid -3- (trimethoxysilyl) propyl ester, relative to mesoporous two
The deal of silica, the trimethoxy silane dosage containing amino are 0.1-2 parts by weight；
(2) p -carboxybenzaldehyde and amidized mesoporous silicon oxide are subjected to amidation process and obtain surface benzaldehyde base
The mesoporous silicon oxide of change；The dosage of p -carboxybenzaldehyde is 0.1-4 parts by weight；Amidation reagent be EDC and NHS, EDC and
The mass ratio of NHS is 1:1- 1:2；Solvent is H2O and DMF, H2O and DMF volume ratio is 4:1-1:4, reaction time 12-48
Hour；
(3) mesoporous silicon oxide that will load drug molecule loading benzaldehyde base under mildly acidic conditions, restores into
Property or alkaline condition realize DOX sealing of hole, the meso-porous nano of sensitive self gate for being loaded with anti-tumor drug DOX of pH can be obtained
Carrier；The molecular weight of the loading drug molecule is not higher than 1000Da, is camptothecine, taxol, cis-platinum, bortezomib, length
Spring new alkali, Xi Tabin one or more.
Solutions of weak acidity is pH 2-6.8 in step (3)；The condition of DOX sealing of hole be pH 7.4-12 neutrality or
10min-12h is impregnated in alkaline DOX solution.
A kind of pH it is sensitive, drug self gate, the antitumor carrier of meso-porous nano, be one or more loadings
Pharmaceutical carrier that is that drug molecule carries altogether and being prepared by DOX molecule sealing of hole.
Compared with the prior art, the present invention has the following beneficial effects:
Mesoporous drug delivery system according to the present invention is not required to be gone to block duct using additional " gate ", but utilized skilful
" self gate " switching material is used as using drug itself wonderfully, advantageously reduces extraneous ingredients in practical tumor therapeutic procedure
Toxic side effect, the medicine-releasing performance with being simple and efficient property and acidic cancer microenvironment sensitivity.Moreover, this control is released
Put system has very sensitive pH responsiveness, it can be achieved that the drug of tumor microenvironment and cell interior can under physiological environment
Controlled release is put.With enlightenment, the mesoporous drug delivery system of drug " self gate " can neatly be applied to other with anti-
The small-molecule drug of tumor promotion, cancer combine control aspect equally have potential application.
Detailed description of the invention
PH sensitivity Covalently attached interaction and DOX molecule between Fig. 1 anti-tumor drug adriamycin (DOX) and benzaldehyde self
Gating principles figure；
Mesoporous silicon oxide self gate of Fig. 2 DOX molecule, being mounted with DOX molecule；
The medicine-releasing performance of mesoporous drug delivery system that Fig. 3 DOX molecule gates self, being mounted with DOX molecule；
In-vivo tumour inhibitory effect (20 self gate of Fig. 4 DOX molecule, being mounted with the mesoporous drug delivery system of DOX molecule
It).
The medicine releasability of mesoporous drug delivery system self gate of Fig. 5 DOX molecule, being mounted with 10- hydroxy-camptothecin molecule
Energy.
Specific embodiment
The present invention is further described below by embodiment.
(1) self gate, the mesoporous drug delivery system that is mounted with DOX drug molecule of DOX molecule
It weighs the dry mesoporous silicon oxide of 1 g to be scattered in 20 ml dry toluenes, (3- aminopropyl) three ethoxies is added
500 μ L of base silane (APTES) flows back 16 hours for 120 DEG C under an argon, after reaction, filtering, with ether and dichloromethane
Alkane mixed solution (1:1) washs 2 times, and vacuum drying obtains surface amination silicon ball.20 ml are added in the flask of 100 ml
Water, 5 ml DMF, p -carboxybenzaldehyde 45 mg, EDC 46 mg of 77 mg, NHS adjust pH value 5 ~ 6, activation pair with dilute hydrochloric acid
Then the carboxyl of carboxyl benzaldehyde is added 0.85 g amination silicon ball, filters after reaction overnight, is washed with water three times, then use DMF
Washing, soaked overnight, alcohol are resuspended, and vacuum drying obtains the mesoporous silicon oxide of benzaldehyde modification.It is dispersed in 200 ml
Ethyl alcohol and 1 g NH4NO3Mixed solution in, flow back 8 hours at 80 DEG C, remove template CTAB, final products filter simultaneously
And with ethanol washing, 24 h are dried in vacuo, obtain mesoporous silicon dioxide nano particle of benzaldehyde modification.
It weighs 200 mg adriamycins (DOX) to be dissolved in the deionized water of 5 ml pH 5 ~ 6, mesoporous silicon oxide is added
100 mg of nanoparticle after 24 hours, sufficiently adsorbs DOX in centrifuge tube, filtering, with deionized water quick wash and mistake
Filter.It washed once with the sodium hydroxide deionized water solution of pH=8.5, and adjust and be restored to neutrallty condition, be lyophilized, obtain DOX
Mesoporous drug delivery system that molecule gates self, being mounted with DOX drug molecule.
The projection Electronic Speculum result of nanometer system is as shown in Fig. 2, load the mesoporous silicon oxide after DOX and DOX gate
Mesopore orbit structure thickens, and surface area is by 1200m2/ g drops to 600m2/ g or so.By testing it in condition of different pH
Under DOX molecule release performance it can be found that the drug delivery system have apparent pH sensitive property (Fig. 3).Intracorporal tumour is real
It tests result to also turn out, mesoporous drug delivery system ratio that this DOX molecule gates self, being mounted with DOX drug molecule simply uses
DOX drug has apparent tumor inhibitory effect (Fig. 4).
(2) self gate, the mesoporous drug delivery system that is mounted with 10-hydroxycamptothecine drug molecule of DOX molecule
It weighs the dry mesoporous silicon oxide of 1 g to be scattered in 20 ml dry toluenes, (3- aminopropyl) three ethoxies is added
500 μ L of base silane (APTES) flows back 16 hours for 120 DEG C under an argon, after reaction, filtering, with ether and dichloromethane
Alkane mixed solution (1:1) washs 2 times, and vacuum drying obtains surface amination silicon ball.20 ml are added in the flask of 100 ml
Water, 5 ml DMF, p -carboxybenzaldehyde 45 mg, EDC 46 mg of 77 mg, NHS adjust pH value 5 ~ 6, activation pair with dilute hydrochloric acid
Then the carboxyl of carboxyl benzaldehyde is added 0.85 g amination silicon ball, filters after reaction overnight, is washed with water three times, then use DMF
Washing, soaked overnight, alcohol are resuspended, and vacuum drying obtains the mesoporous silicon oxide of benzaldehyde modification.It is dispersed in 200 ml
Ethyl alcohol and 1 g NH4NO3Mixed solution in, flow back 8 hours at 80 DEG C, remove template CTAB, final products filter simultaneously
And with ethanol washing, 24 h are dried in vacuo, obtain mesoporous silicon dioxide nano particle of benzaldehyde modification.
It weighs 200 mg 10-hydroxycamptothecines to be dissolved in 5 ml DMSO, mesoporous silicon dioxide nano particle 100 is added
Mg adjusts pH value to after 6.0,24 hours, sufficiently adsorbs in centrifuge tube, filters, with deionized water quick wash and filtering.
With the DOX aqueous solution of pH=8.5, deionized water be washed once, freeze-drying, obtain DOX molecule self gate, be mounted with 10- hydroxyl
The mesoporous drug delivery system of base camptothecin molecule.By testing its 10-hydroxycamptothecine molecule release property under condition of different pH
It can be it can be found that the drug delivery system has apparent pH sensitive property (Fig. 5).
The above is only a preferred embodiment of the present invention, it should be pointed out that: for the ordinary skill people of the art
For member, without departing from the principle of the present invention, the replacement of several improvement and equivalent form can also be made, these improvement
The technical solution obtained with equivalent replacement also should belong to protection scope of the present invention.
Claims (7)
1. a kind of pH it is sensitive, drug self gate, the antitumor carrier of meso-porous nano preparation method, it is characterised in that: adopt
The mesoporous silicon oxide and broad-spectrum anti-cancer drug Doxorubicin (DOX) for containing benzaldehyde with surface are carried respectively as meso-porous nano
Body and gate drug molecule；
Preparation method includes the following steps:
(1) mesoporous silicon oxide is reacted to obtain the meso-porous titanium dioxide of surface amination with the trimethoxy silane containing amino
Silicon；Trimethoxy silane containing amino is methacrylic acid -3- (trimethoxysilyl) propyl ester, relative to mesoporous dioxy
The deal of SiClx, the trimethoxy silane dosage containing amino are 0.1-2 parts by weight；
(2) p -carboxybenzaldehyde and amidized mesoporous silicon oxide are subjected to amidation process and obtain surface benzaldehyde base
Mesoporous silicon oxide；The dosage of p -carboxybenzaldehyde is 0.1-4 parts by weight；Amidation reagent is EDC's and NHS, EDC and NHS
Mass ratio is 1:1- 1:2；Solvent is H2O and DMF, H2O and DMF volume ratio is 4:1-1:4, and the reaction time is 12-48 hours；
(3) broad-spectrum anti-cancer drug Doxorubicin (DOX) is loaded into the meso-porous titanium dioxide of benzaldehyde base under mildly acidic conditions
Silicon restores to realize DOX sealing of hole to neutral or alkaline condition, self door for being loaded with anti-tumor drug DOX of pH sensitivity can be obtained
The meso-porous nano carrier of control.
2. a kind of pH according to claim 1 it is sensitive, drug self gate, the antitumor carrier of meso-porous nano preparation
Method, which is characterized in that the mesoporous silicon oxide of step (1) is based on ordered mesopore silicon dioxide nano material, average grain diameter
50-300 nm, 2.4-3.5 nm of aperture, 400-1200 m of specific surface2/g。
3. a kind of pH according to claim 1 it is sensitive, drug self gate, the antitumor carrier of meso-porous nano preparation
Method, which is characterized in that gate drug molecule is the broad-spectrum anti-cancer drug Doxorubicin (DOX) containing amino group.
4. a kind of pH according to claim 1 it is sensitive, drug self gate, the antitumor carrier of meso-porous nano preparation
Method, which is characterized in that the solutions of weak acidity that gate drug molecule DOX is loaded in step (3) is pH 2-6.8；Gate drug
The condition of molecule DOX sealing of hole is to impregnate 10min-12h in the neutrality of pH 7.4-12 or alkaline solution.
5. a kind of pH it is sensitive, drug self gate, the antitumor carrier of meso-porous nano preparation method, it is characterised in that: adopt
The mesoporous silicon oxide and broad-spectrum anti-cancer drug Doxorubicin (DOX) for containing benzaldehyde with surface are carried respectively as meso-porous nano
Body and gate drug molecule；
Preparation method includes the following steps:
(1) mesoporous silicon oxide is reacted to obtain the meso-porous titanium dioxide of surface amination with the trimethoxy silane containing amino
Silicon；Trimethoxy silane containing amino is methacrylic acid -3- (trimethoxysilyl) propyl ester, relative to mesoporous dioxy
The deal of SiClx, the trimethoxy silane dosage containing amino are 0.1-2 parts by weight；
(2) p -carboxybenzaldehyde and amidized mesoporous silicon oxide are subjected to amidation process and obtain surface benzaldehyde base
Mesoporous silicon oxide；The dosage of p -carboxybenzaldehyde is 0.1-4 parts by weight；Amidation reagent is EDC's and NHS, EDC and NHS
Mass ratio is 1:1- 1:2；Solvent is H2O and DMF, H2O and DMF volume ratio is 4:1-1:4, and the reaction time is 12-48 hours；
(3) drug molecule will be loaded under mildly acidic conditions, and Jie of benzaldehyde base is loaded by molecule diffusion and electrostatic interaction
Hole silica restores to realize DOX sealing of hole to neutrallty condition, can be obtained pH it is sensitive be loaded with anti-tumor drug DOX self
The meso-porous nano carrier of gate；The molecular weight of the described loading drug molecule is not higher than 1000Da, is camptothecine, taxol, suitable
Platinum, bortezomib, vincristine, Xi Tabin one or more.
6. a kind of pH according to claim 5 it is sensitive, drug self gate, the antitumor carrier of meso-porous nano preparation
Method, which is characterized in that solutions of weak acidity is pH 2-6.8 in step (3)；The condition of DOX sealing of hole is in pH 7.4-12
Alkaline DOX solution in impregnate 10min-12h.
7. a kind of pH it is sensitive, drug self gate, the antitumor carrier of meso-porous nano, be one kind described in claim 5 or
It is a variety of to load pharmaceutical carrier that is that drug molecule carries altogether and being prepared by DOX molecule sealing of hole.
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| CN109602518B (en) * | 2017-09-30 | 2020-10-09 | 厦门大学 | Fluid-gated artificial blood vessel |
| CN108743951B (en) * | 2018-06-06 | 2021-06-11 | 江苏师范大学 | Preparation method of pH-responsive degradable hollow mesoporous organic silicon nanoparticles |
| CN112083162A (en) * | 2019-07-16 | 2020-12-15 | 何金星 | Diagnostic preparation for determining immunity level |
| CN111068057A (en) * | 2019-12-31 | 2020-04-28 | 广东药科大学 | PH/redox dual-response magnetic nano drug-loaded system and construction method thereof |
| CN111562389A (en) * | 2020-05-19 | 2020-08-21 | 重庆宏道拓土科技有限公司 | Composite material for forming docking station of glucometer and preparation method and application thereof |
| CN111973752A (en) * | 2020-09-03 | 2020-11-24 | 中山大学·深圳 | Urotropine-loaded mesoporous nano silicon spheres and preparation method thereof |
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