CN106620708A - Multifunctional drug carrier as well as preparation method and application thereof - Google Patents
Multifunctional drug carrier as well as preparation method and application thereof Download PDFInfo
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/498—Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
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- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/28—Steroids, e.g. cholesterol, bile acids or glycyrrhetinic acid
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Abstract
The invention relates to a multifunctional drug carrier as well as a preparation method and application thereof. The multifunctional drug carrier is prepared from mesoporous silicon dioxide nanoparticles and liposomes at the mass ratio of 1 to (1.5 to 2.5), wherein the liposomes comprise lecithin, cholesterol and 1,5-octadecyl-L-glutamic acid-2-histidine-hexahydrophthalic anhydride. The multifunctional drug carrier integrates three functions of realizing double carriers, promoting cell uptake and triggering drug releasing, and is not limited by cell heterogeneity; the multifunctional drug carrier has wide applicability and provides an efficient carrier platform for effective application of synergistic drugs.
Description
Technical field
The present invention relates to field of pharmaceutical chemistry technology, more particularly to a kind of multi-functional drug carriers and preparation method thereof and
Using.
Background technology
Current study show that, single medicine can not thoroughly treat tumour for oncotherapy, and this is mainly due to tumour
Cell has certain modulability, and clinic gives for a long time single medicine, causes tumour cell to produce tolerance, causes medicine to lose
Oncotherapy is gone to act on, in particularly simple chemotherapy, the determination of generally existing MDR.Drug combination can be effective
Prevent tumour cell from drug resistance occur, improve the therapeutic action of medicine.
The key means of drug combination are exactly that design medicine is combined and passs release system, and the feature of current pharmaceutical carrier is more single
One, although many carriers are provided simultaneously with triggering drug release and promote the dual-use function of cellular uptake, but can only singly carry medicine, it is impossible to
Meet the loading demand of the cooperative drug of high efficiency.And at present minority is capable of the carriers of double load medicines or lacks the work(of triggering drug release
Can, or cannot realize promoting cellular uptake.Which has limited effectively using for cooperative drug.
The content of the invention
Based on this, it is an object of the invention to provide a kind of double can carry medicine, promote cellular uptake and trigger insoluble drug release
Multi-functional drug carriers.
Specific technical scheme is as follows：
A kind of multi-functional drug carriers, including mass ratio is 1:The mesoporous silicon dioxide nano particle and liposome of 1.5-2.5,
The liposome includes lecithin, cholesterol and 1,5- octadecyl-Pidolidone -2- histidines-HHPA.
Wherein in some embodiments, the liposome includes that mass ratio is 1-1.5:3.5-4:1 1,5- octadecyls-
Pidolidone -2- histidines-HHPA：Lecithin：Cholesterol.
Wherein in some embodiments, it is 1.25 that the liposome is mass ratio:3.75:1 1,5- octadecyl-L- paddy
Propylhomoserin -2- histidines-HHPA：Lecithin：Cholesterol.
Wherein in some embodiments, the mesoporous silicon dioxide nano particle is received for the mesoporous silicon oxide of amino functional
The grain of rice, particle diameter is 80-100nm.
It is a further object of the present invention to provide the preparation method of above-mentioned multi-functional drug carriers.
Specific technical scheme is as follows：
The preparation method of above-mentioned multi-functional drug carriers, comprises the steps：
Lecithin, cholesterol and 1,5- octadecyl-Pidolidone -2- histidines-HHPA is dissolved in into organic solvent,
In 35-45 DEG C of vacuum rotating film forming, dry lipid film；
The mesoporous silicon dioxide nano particle is dispersed in water, 15- is reacted with the lipid film hydration in 35-40 DEG C
30min；
Product is collected by centrifugation, washing obtains final product the multi-functional drug carriers.
It is a further object of the present invention to provide a kind of double load medicines.
Specific technical scheme is as follows：
A kind of double load medicines, including above-mentioned multi-functional drug carriers, dewatering medicament and hydrophilic drugs.
Wherein in some embodiments, the dewatering medicament is 1 with the mass ratio of the multi-functional drug carriers:80-
120；The hydrophilic drugs are 1-1.5 with the mass ratio of the multi-functional drug carriers:80-120.
Wherein in some embodiments, the dewatering medicament is selected from II classes and life in Biopharmaceutics Classification system (BCS)
One or more in thing Biopharmaceutical Classification system (BCS) in IV class；The hydrophilic drugs are selected from：Biopharmaceutics Classification system
(BCS) one or more in I class and Biopharmaceutics Classification system (BCS) in III class.
One or more in categorizing system BCS in I class and Biopharmaceutics Classification system BCS in III class.
It is a further object of the present invention to provide above-mentioned double preparation methods for carrying medicine.
Specific technical scheme is as follows：
Above-mentioned double preparation methods for carrying medicine, comprise the steps：
By dewatering medicament, lecithin, cholesterol and 1.5-, octadecyl-Pidolidone-histidine-HHPA is dissolved in has
Machine solvent, in 35-40 DEG C of vacuum rotating film forming, the dry lipid film that must load dewatering medicament；
Mesoporous silicon dioxide nano particle is scattered in the aqueous solution of hydrophilic drugs, 22-26h is incubated altogether, product is collected by centrifugation
Thing, washing obtains final product the mesoporous silicon dioxide nano particle for loading hydrophilic drugs；
By it is described loading hydrophilic drugs mesoporous silicon dioxide nano particle be dispersed in water, in 35-40 DEG C with the loading
The lipid film hydration reaction 15-30min of dewatering medicament；
Product is collected by centrifugation, washing obtains final product double load medicines.
Above-mentioned multi-functional drug carriers adopt the mesoporous silicon dioxide nano particle of the amino functional of positive electricity for kernel, adopt
Liposome with pH sensitivity electric charge upsets is used as shell.In neutral conditions, by Electrostatic Absorption mode by liposomal
To the mesoporous silica nanospheres surface of amino functional, multi-functional drug carriers are built.In neutral conditions, due to top layer
Double-layer of lipoid is closely coated on the mesoporous silica nanospheres surface of amino functional, and the carrier is in stable " nucleocapsid " structure
Negative electricity nanosphere, wherein double-layer of lipoid and mesoporous equal medicine-carried；And under the solutions of weak acidity of tumor tissues, the fat of carrier outer layer
Matter is double-deck to there is electric charge upset, and by negative electricity positive electricity is become, and increases the absorption with negative electricity cell membrane, reaches the mesh for promoting cellular uptake
's；Under strong acidic condition in the cell, the positive electrification of outer layer double-layer of lipoid is strengthened, the meso-porous titanium dioxide with kernel amino functional
Silicon nanosphere produces strong Coulomb repulsion, the rock-steady structure of double-layer of lipoid and carrier is destroyed, so as to trigger the release of medicine.
Above-mentioned multi-functional drug carriers integrate double loads, promote cellular uptake and triggering drug release triple functions, and do not receive
Cell is heterogeneous to be limited, and with broad applicability, the effective application for cooperative drug provides an efficient carrier platform.
Description of the drawings
Fig. 1 is the TEM photo and Cryo-TEM photos of embodiment multi-functional drug carriers；
Fig. 2 is multi-functional drug carriers electric charge upset in different pH buffer salts；
Fig. 3 is the intake of Si elements during cell is to carrier in different pH environment；
Fig. 4 is multi-functional drug carriers resonance energy transfer in different pH environment；
Fig. 5 is intake of the cell to erlotinib in carrier (left side) and DOX (right side) under different pH；
Fig. 6 is the release of erlotinib (left side) and DOX (right side) in carrier under condition of different pH.
Specific embodiment
For the ease of understanding the present invention, the present invention is described more fully below with reference to relevant drawings.But, this
Invention can be realized in many different forms, however it is not limited to embodiment described herein.On the contrary, providing these enforcements
The purpose of example is to make the understanding to the disclosure more thorough comprehensive.
Unless otherwise defined, all of technology used herein and scientific terminology and the technical field for belonging to the present invention
The implication that technical staff is generally understood that is identical.The term for being used in the description of the invention herein is intended merely to description tool
The purpose of the embodiment of body, it is not intended that of the invention in limiting.Term as used herein "and/or" includes one or more phases
The arbitrary and all of combination of the Listed Items of pass.
Embodiment 1
A kind of multi-functional drug carriers of the present embodiment, including mass ratio is 1:2 mesoporous silicon dioxide nano particle (Amino
functionalized mesoporous silica nanoparticle,MSN-NH2, 80-100nm) and liposome, it is described
It is 1.25 that liposome is mass ratio:3.75:1 1,5- octadecyls-Pidolidone -2- histidines-HHPA (1,5-
Dioctadecyl-L-glutamyl-2-histidyl-hexahydrobenzoic acid, HHG2C18)：Soybean lecithin
(Soy Phosphatidylcholine,SPC)：Cholesterol (Cholesterol, Chol).
The mesoporous silicon dioxide nano particle is the mesoporous silicon dioxide nano particle of amino functional, and particle diameter is 80-
100nm。
The preparation method of above-mentioned multi-functional drug carriers, comprises the steps：
It is 3.75 by 120mg mass ratioes:1:1.25 lecithin, cholesterol and 1,5- octadecyls-Pidolidone -2- groups
Propylhomoserin-HHPA is dissolved in 5ml chloroforms, moves into eggplant type bottle, in 40 DEG C of vacuum rotating film forming, is vacuum dried 4h, obtains lipid film
(pH sensitivity electric charge upset lipid films)；
Mesoporous silicon dioxide nano particle described in 60mg is scattered in 5ml pure water, in 37 DEG C with the lipid film hydration
Reaction 15-30min；
Product is collected by centrifugation, pure water washing repeatedly, is collected precipitation and obtains final product the multi-functional drug carriers.
Above-mentioned multi-functional drug carriers performance test data：
(1) medicine is double carries performance
Shown in multi-functional drug carriers Electronic Speculum Fig. 1, carrier is in " nucleocapsid " nanospheres, and kernel is MSN-NH2, as one
Plant drug loading point；Shell is double-layer of lipoid, is another drug loading point, for loading hydrophobic drug.
(2) electric charge upset, promotes cellular uptake performance
Carrier pH sensitivity electric charge turn over function is as shown in Figure 2.During pH 7.4, surface potential is in negative electricity, about -38mV；pH
When 6.5, surface potential is turned into positive electricity, about 4.5mv；Under the conditions of higher acidity (pH 4.5/5.5), surface potential is just electrochemical
Strengthen (22mv).It is the HHG in carrier to occur the reason for electric charge overturns2C18Hydrolyze, in neutral environment, HHG2C18In negative
Electricity, in the sour environments of pH 6.5, due to HHG2C18The protonation of middle histidine and carboxyl so that carrier is in positive electricity, when in pH
When in 5.5 acid higher environment, in addition to protonated amino, HHPA group come off so that carrier electropositive more
By force, when pH continues to be down to 4.5, current potential is essentially the same with during pH 5.5, and this is probably due to HHG2C18Middle protonated amino and six
Coming off for hydrogen phthalic anhydride group reaches saturation state.
Fig. 3 shows that electric charge upset promotes cellular uptake, and the intake of the composition Si elements of carrier is estimated with cell.
Under the acid conditions of pH 6.5, because carrier occurs electric charge upset, positive electricity is become by negative electricity, therefore be easier to be inhaled with negative electricity cell membrane
Attached, so as to promote cellular uptake, result shows in figure, and cellular uptake amount under the neutrallty conditions of pH 7.4 than showing under the conditions of pH 6.5
Work increases.
(3) Coulomb repulsion promotes Release Performance
Electrostatic row of Fig. 4 tables in bright pH 5.5 and pH 4.5, between the positive electrification double-layer of lipoid of carrier and kernel MSN-NH2
Scold stable " nucleocapsid " structure of disturbance carrier, may advantageously facilitate entrapped drug release.
Embodiment 2
A kind of double load medicines, including multi-functional drug carriers, the dewatering medicament (Erlotinib that embodiment 1 is prepared
) and hydrophilic drugs (ADMh DOX) erlotinib.
Above-mentioned double preparation methods for carrying medicine, comprise the steps：
It is 3.75 by 120mg mass ratioes:1:1.25 lecithin, cholesterol, 1.5- octadecyls-Pidolidone -2- groups
Propylhomoserin-HHPA and 1mg erlotinib are dissolved in 5mL chloroforms, eggplant-shape bottle are moved into, in 40 DEG C of vacuum rotating film forming, vacuum
4h is dried, the lipid film (pH sensitivity electric charge upset lipid films) of erlotinib must be loaded；
60mg mesoporous silicon dioxide nano particles are scattered in the aqueous solution of DOX, 24h is incubated altogether, product is collected by centrifugation, washed
Wash and obtain final product the mesoporous silicon dioxide nano particle for loading DOX；
The mesoporous silicon dioxide nano particle of the loading DOX is dispersed in water, with 37 DEG C with the loading erlotinib
Lipid film hydration reaction 15-30min；
Product is collected by centrifugation, pure water washing for several times, is collected precipitation and obtains final product double multifunctional medicals for carrying erlotinib and DOX
Thing delivery system.
Above-mentioned double performance datas for carrying medicine：
(1) double load performances
With dewatering medicament Erlotinib (erlotinib) and hydrophilic drugs ADMh (DOX) as medicine, encapsulate respectively
Into carrier outer layer double-layer of lipoid and kernel MSN-NH2, double load medicament purposes are reached.
(2) electric charge upset promotes cellular uptake performance
Carrier produces electric charge upset under the solutions of weak acidity of pH 6.5 and promotes cellular uptake experimental result as shown in Figure 5.
The solutions of weak acidity of pH 6.5 exists, and due to the upset of carrier surface electric charge, promotes cellular uptake, so intake ratio of the cell to medicine
The intake of the neutrallty conditions of pH 7.4 is big.
(3) Coulomb repulsion promotes to contain medicine-releasing performance
Coulomb repulsion between carrier outer layer double-layer of lipoid and kernel MSN-NH2 promotes the experimental result of drug release as shown in Figure 6.
As we know from the figure under pH 5.5 and the strong acidic conditions of pH 4.5, because repulsive force strong between double-layer of lipoid and MSN-NH2 breaks
Bad carrier stabilization result, so as to increase the burst size of medicine.Under the neutrallty conditions of pH 7.4, because carrier is in firm nucleocapsid knot
Really, thus limited reduction medicine release.
Each technical characteristic of embodiment described above can be combined arbitrarily, to make description succinct, not to above-mentioned reality
Apply all possible combination of each technical characteristic in example to be all described, as long as however, the combination of these technical characteristics is not deposited
In contradiction, the scope of this specification record is all considered to be.
Embodiment described above only expresses the several embodiments of the present invention, and its description is more concrete and detailed, but and
Can not therefore be construed as limiting the scope of the patent.It should be pointed out that for one of ordinary skill in the art comes
Say, without departing from the inventive concept of the premise, some deformations and improvement can also be made, these belong to the protection of the present invention
Scope.Therefore, the protection domain of patent of the present invention should be defined by claims.
Claims (9)
1. a kind of multi-functional drug carriers, it is characterised in that including mass ratio be 1:The mesoporous silicon dioxide nano particle of 1.5-2.5
And liposome, the liposome include lecithin, cholesterol and 1,5- octadecyl-Pidolidone -2- histidines-hexahydrobenzene
Acid anhydride.
2. multi-functional drug carriers according to claim 1, it is characterised in that the liposome includes that mass ratio is 1-
1.5:3.5-4:1 1,5- octadecyls-Pidolidone -2- histidines-HHPA：Lecithin：Cholesterol.
3. multi-functional drug carriers according to claim 1, it is characterised in that it is 1.25 that the liposome is mass ratio:
3.75:1 1,5- octadecyls-Pidolidone -2- histidines-HHPA：Lecithin：Cholesterol.
4. multi-functional drug carriers according to any one of claim 1-3, it is characterised in that the mesoporous silicon oxide is received
The grain of rice is the mesoporous silicon dioxide nano particle of amino functional, and particle diameter is 80-100nm.
5. the preparation method of the multi-functional drug carriers described in any one of claim 1-4, it is characterised in that including following step
Suddenly：
Lecithin, cholesterol and 1,5- octadecyl-Pidolidone -2- histidines-HHPA is dissolved in into organic solvent, in
35-45 DEG C of vacuum rotating film forming, dry lipid film；
The mesoporous silicon dioxide nano particle is dispersed in water, 15-30min is reacted with the lipid film hydration in 35-40 DEG C；
Product is collected by centrifugation, washing obtains final product the multi-functional drug carriers.
6. it is a kind of double to carry medicine, it is characterised in that including multi-functional drug carriers described in any one of claim 1-4, hydrophobic
Medicine and hydrophilic drugs.
7. according to claim 6 pair carries medicine, it is characterised in that the dewatering medicament and the multi-functional drug carriers
Mass ratio be 1:80-120；The hydrophilic drugs are 1-1.5 with the mass ratio of the multi-functional drug carriers:80-120.
8. according to claim 6 pair carries medicine, it is characterised in that the dewatering medicament is selected from Biopharmaceutics Classification system
One or more in system in II classes and Biopharmaceutics Classification system in IV class；The hydrophilic drugs are selected from：Biopharmacy
One or more in categorizing system in I class and Biopharmaceutics Classification system in III class.
9. the preparation method of the double load medicines described in any one of claim 6-8, it is characterised in that comprise the steps：
Dewatering medicament, lecithin, cholesterol and 1.5- octadecyl-Pidolidone-histidine-HHPA is dissolved in organic molten
Agent, in 35-40 DEG C of vacuum rotating film forming, the dry lipid film that must load dewatering medicament；
Mesoporous silicon dioxide nano particle is scattered in the aqueous solution of hydrophilic drugs, 22-26h is incubated altogether, product is collected by centrifugation, washed
Wash and obtain final product the mesoporous silicon dioxide nano particle for loading hydrophilic drugs；
The mesoporous silicon dioxide nano particle of the loading hydrophilic drugs is dispersed in water, loads hydrophobic with described in 35-40 DEG C
The lipid film hydration reaction 15-30min of medicine；
Product is collected by centrifugation, washing obtains final product double load medicines.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113230412A (en) * | 2021-05-11 | 2021-08-10 | 中南大学 | Mesoporous silica-lipid composite nano material and preparation method and application thereof |
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| CN102603866A (en) * | 2012-03-15 | 2012-07-25 | 中国药科大学 | Oligopeptide-based pH-sensitive amphoteric ion and application thereof in medicament |
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| CN103687588A (en) * | 2011-05-16 | 2014-03-26 | 丹麦科技大学 | Charge triggering of self-organized nanoparticles |
| CN102603866A (en) * | 2012-03-15 | 2012-07-25 | 中国药科大学 | Oligopeptide-based pH-sensitive amphoteric ion and application thereof in medicament |
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| CN113230412A (en) * | 2021-05-11 | 2021-08-10 | 中南大学 | Mesoporous silica-lipid composite nano material and preparation method and application thereof |
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Application publication date: 20170510 |