CN105796529A - Preparation method and applications of gambogic acid self-assembled polymer nanoparticles - Google Patents
Preparation method and applications of gambogic acid self-assembled polymer nanoparticles Download PDFInfo
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Abstract
The invention relates to a preparation method and applications of gambogic acid self-assembled polymer nanoparticles. The preparation method comprises the following steps: adding polyethylene glycol, epsilon-caprolactone, stannous octoate and methylbenzene into a three-necked bottle, and carrying out oil bath reaction at 130 DEG C for 12h under the stirring state and under the protection of N2; after the reaction, removing methylbenzene through rotary evaporation; dissolving the product by adopting dichloromethane, slowly dropwise adding the obtained solution into plenty of cold petroleum ether for precipitation, operating repeatedly, and carrying out suction filtration to obtain a polymer material; taking gambogic acid, placing gambogic acid into an eggplant-shaped bottle, adding acetonitrile for dissolving gambogic acid, adding the polymer material into the obtained solution for dissolving, removing acetonitrile through rotary evaporation, after removing of acetonitrile, a layer of medicinal film is formed on the wall of the bottle, placing the bottle into a vacuum drying oven, removing trace amount of acetonitrile, adding purified water into the bottle, carrying out hydration treatment under 65 DEG C, placing the obtained solution into an ice-water bath, carrying out ultrasound treatment for twice under the power of 315W, wherein each time of ultrasound treatment lasts for 2 min, and after the ultrasound treatment, filtering the obtained solution by a 0.45 [mu] m filter membrane. The prepared nanoparticles are high in encapsulation efficiency, high in drug loading capacity, and good in stability.
Description
Technical field
Gamlogic acid self-assembling polymers nanoparticle that the present invention relates to a kind of high encapsulation rate and its preparation method and application, belongs to doctor
Medicine chemical technology field.
Background technology
Gamlogic acid (gambogic acid, GA) is the main active of Resina garciniae, can selectively induce tumor cell and wither
Die, the most all shown the strongest antitumor action, kinds of tumor cells is had stronger inhibitory action,
And to normal hemopoietic system and immunologic function without obvious inhibition.Gamlogic acid antineoplastic mechanism may be blocks cellular week
Phase, inducing cell apoptosis, suppression angiogenesis and TfR (TfR) combine and affect the table of related gene and albumen
Reach etc. relevant.Due to gamlogic acid dissolubility in water minimum (less than 0.5 μ g/mL), plasma clearance is fast, the most widely distributed,
The bioavailability that result in gamlogic acid is the lowest, significantly limit its Clinical practice.Therefore, developing anti-tumor medicaments gamlogic acid
Novel form be one of required key issue solved of tumor research and development.
Self-assembling polymers nanoparticle, is a kind of novel nano carrier that fast development is got up in recent years.It is by amphipathic
Compound is self-assembly of after reaching critical aggregation concentration (CMC) in water, have the core of hydrophobic cores and hydrophilic shell-
Shell type structure, also known as polymer micelle.Self-assembling polymers nanoparticle had both provided a hydrophobic kernel as drug-reservoir,
Provide again a hydrophilic shell with the stability maintaining in water environment.Just because of the structure that it is special, self assembly is polymerized
Thing nanoparticle can increase medicine stability in vivo and in vitro, increases the dissolubility of hydrophobic drug, and improves the biography of drug molecule
Pass performance.As novel drug delivery system, self-assembled nanometer grain is also equipped with the character that other are tempting, such as can be modified
Realize active targeting, there is good biocompatibility, increase bioavailability etc..Owing to it has less particle diameter, therefore
It is easy to be gathered in tumor tissues by " permeate and retain " (EPR) effect, plays targeting, and it is right to alleviate simultaneously
The toxic and side effects of normal structure.
At present, in the existing preparation of gamlogic acid, it is commonly incorporated into solubilizing agent or cosolvent to solve the problem that its dissolubility is little.But
These solubilizing agents and the life-time service of cosolvent, can cause nephrotoxicity, allergy, neurotoxicity and Cardiovascular Toxicity etc. a series of
Untoward reaction.Also researcher is had to have studied the novel form of gamlogic acid, but the defects such as existence and stability is poor, drug loading is low mostly,
So the novel formulation studying a kind of gamlogic acid is extremely urgent to solve the defects such as its dissolubility is little, bioavailability is low.
Summary of the invention
The shortcoming such as the preparation stability that it is an object of the invention to overcome existing gamlogic acid is poor, envelop rate is low and drug loading is low, it is provided that
A kind of high encapsulation rate, high drug load, the preparation method and applications of stable gamlogic acid self-assembling polymers nanoparticle.
The technical solution used in the present invention is: the preparation method of a kind of gamlogic acid self-assembling polymers nanoparticle, including walking as follows
Rapid:
1) prepared by polymeric material: join in three-necked bottle by Polyethylene Glycol, 6-caprolactone, stannous octoate and toluene, at machinery
Stirring and N2Under protection, 120-140 DEG C of oil bath reaction 10-14h；After reaction terminates, product naturally cools to
Room temperature, screws out toluene；Use dichloromethane lysate, after product all dissolves, it is instilled slowly petroleum ether
In precipitate, sucking filtration, precipitation again with dichloromethane dissolve, in being slowly dropped into petroleum ether, repetitive operation, mistake
Filter, obtains white product, vacuum drying, obtains polymeric material；
2) take gamlogic acid to be placed in eggplant-shape bottle, after adding acetonitrile dissolving, add polymeric material, again dissolve, utilize rotation
Turning evaporimeter and screw out acetonitrile, acetonitrile forms one layer of pharmaceutical film on bottle wall after screwing out, and puts in vacuum drying oven 40 DEG C
Vacuum overnight, removes trace acetonitrile, adds pure water, carries out hydration process 2-8h, then will at 60-70 DEG C
Solution is placed in ice-water bath, under 135-315W power ultrasonic 2-6 time, each 2min, ultrasonic end, mistake
0.45 μm filter membrane, obtains gamlogic acid self-assembling polymers nanoparticle.
The preparation method of above-mentioned a kind of gamlogic acid self-assembling polymers nanoparticle, described Polyethylene Glycol is selected from Polyethylene Glycol
2000, Macrogol 4000, polyethylene glycol 6000 and PEG 8000.Preferably, described Polyethylene Glycol is poly-second two
Alcohol 6000.
The preparation method of above-mentioned a kind of gamlogic acid self-assembling polymers nanoparticle, in molar ratio, 6-caprolactone: Polyethylene Glycol
=2:0.1～9:0.1.Preferably, 6-caprolactone: Polyethylene Glycol=4:0.1.
The preparation method of above-mentioned a kind of gamlogic acid self-assembling polymers nanoparticle, in mass ratio, gamlogic acid: polymeric material=1:
5～1:1.25.Preferably, gamlogic acid: polymeric material=1:1.25.
The preparation method of above-mentioned a kind of gamlogic acid self-assembling polymers nanoparticle, it is preferred that ultrasonic power is 315W.
The preparation method of above-mentioned a kind of gamlogic acid self-assembling polymers nanoparticle, it is preferred that ultrasonic 2 times, each 2min.
The gamlogic acid self-assembling polymers nanoparticle prepared according to above-mentioned method application in preparing anti-tumor medicinal preparation.
The present invention, the hydrophilic block with Polyethylene Glycol as polymer, in the catalysis of stannous octoate, causes 6-caprolactone (ε-CL) to open
Cyclopolymerization, synthesis equation is as follows:
The invention has the beneficial effects as follows: the present invention selects Polyethylene Glycol to be hydrophilic block, and polycaprolactone is hydrophobic block, both of which
Biological nontoxic, bio-compatible, synthesis has the polymer PCL-PEG-PCL of biocompatibility.Water-soluble
In liquid, polymer self assembles is " sun flower pattern " nanoparticle, is wrapped in by gamlogic acid wherein, transmits, solves its indissoluble
Sex chromosome mosaicism, extends its action time in vivo, improves bioavailability.Gamlogic acid self-assembling polymers prepared by the present invention is received
The grain of rice, has long circulating, good effect, good stability, toxicity are little, good biocompatibility, envelop rate high and drug loading is high spy
Point, envelop rate is up to 99%, and drug loading is up to 40%.
Accompanying drawing explanation
Fig. 1 is the grain size distribution of the gamlogic acid self-assembling polymers nanoparticle of embodiment 2 preparation.
Fig. 2 is the transmission electron microscope observing aspect graph of the gamlogic acid self-assembling polymers nanoparticle of embodiment 2 preparation；
In figure, a:200nm observes under the visual field；B:600nm observes under the visual field.
Fig. 3 is the nanoparticle release in vitro figure of the gamlogic acid self-assembling polymers nanoparticle of embodiment 2 preparation.
Fig. 4 is gamlogic acid and the gamlogic acid self-assembling polymers nanoparticle inhibitory action when 24h to BGC-823 cell.
Fig. 5 is gamlogic acid and the gamlogic acid self-assembling polymers nanoparticle inhibitory action when 36h to BGC-823 cell.
Fig. 6 is gamlogic acid and the gamlogic acid self-assembling polymers nanoparticle inhibitory action when 48h to BGC-823 cell.
Fig. 7 is that rat vein is administered mean blood plasma concentration-time graph after gamlogic acid and gamlogic acid self-assembling polymers nanoparticle.
Detailed description of the invention
The preparation method of embodiment 1 gamlogic acid self-assembling polymers nanoparticle
Preparation method is as follows:
1) prepared by polymeric material: by 0.04mol polyethylene glycol 6000,0.001mol 6-caprolactone, 0.0001mol stannous octoate
Join in three-necked bottle with 5ml toluene, at mechanical agitation and N2Under protection, 130 DEG C of oil bath reaction 12h；Reaction terminates
After, product naturally cools to room temperature, screws out toluene；Use dichloromethane lysate, after product all dissolves, will
It instills slowly in the coldest petroleum ether and precipitates, sucking filtration, and precipitation is dissolved with dichloromethane again, is being slowly dropped into
In petroleum ether, repetitive operation, filter, obtain white product, 40 DEG C of vacuum drying, obtain polymeric material.
2) take 40mg gamlogic acid respectively to be placed in eggplant type bottle, after adding the dissolving of 10ml acetonitrile, add 50mg polymeric material
Material, dissolves again, utilizes Rotary Evaporators to screw out acetonitrile, forms one layer of pharmaceutical film, put into after acetonitrile back-out on bottle wall
In vacuum drying oven, 40 DEG C of vacuum are overnight, remove trace acetonitrile, add 20ml pure water, carry out at aquation at 65 DEG C
Reason 4h, is then placed in solution in ice-water bath, respectively under 45W, 135W, 225W, 315W power ultrasonic 2
Secondary, each 2min, ultrasonic end, cross 0.45 μm filter membrane, obtain gamlogic acid self-assembling polymers nanoparticle.Result is such as
Table 1.
Table 1
Under 45W and 135W ultrasonic, have substantial amounts of precipitation to produce, illustrate that the nanoparticle formed is less, most of medicine is not
It is wrapped and settles.From table 1, the nanoparticle solution that 225W power prepares, particle diameter and PDI all ratio 315W power
The nanoparticle prepared is big, it is considered to the nanoparticle that 315W power prepares disperses evenly.For envelop rate and drug loading, ultrasonic merit
When rate is 315W, envelop rate is the highest, is 99.12%, and drug loading is 41.20%.It is preferred, therefore, that ultrasonic power is 315W.
The preparation of embodiment 2 gamlogic acid self-assembling polymers nanoparticle
Method is with embodiment 1, and ultrasonic power selects 315W, simply change ultrasonic number of times be respectively 1 time, 2 times, 3 times,
4 times, 5 times, 6 times, each 2min, record the particle diameter of gamlogic acid self-assembling polymers nanoparticle, PDI, envelop rate, load
Dose such as table 2.
Table 2
From table 2, when ultrasonic time is increased 4min by 2min, envelop rate and drug loading are the highest.When continuing to increase ultrasonic
Between, envelop rate declines on the contrary.And ultrasonic time is long, polymer backbone is caused to rupture, particle failure, solution is unstable,
There are some coagulations.It is preferred, therefore, that the time is 4min.
The preparation of embodiment 3 gamlogic acid self-assembling polymers nanoparticle
Method selects 315W with embodiment 1, ultrasonic power, simply changes hydration time and is respectively 2h, 4h, 6h, 8h, surveys
Obtain the particle diameter of gamlogic acid self-assembling polymers nanoparticle, PDI, envelop rate, drug loading such as table 3.
Table 3
As seen in Table 3, hydration time is increased to 8h by 2h, and when 4h, envelop rate and drug loading reach the highest, selects
Hydration time 4h.
The preparation of embodiment 4 gamlogic acid self-assembling polymers nanoparticle
Method, with embodiment 1, simply changes rate of charge, the mass ratio of gamlogic acid and polymeric material be respectively 1:10,1:5,
1:2,1:1.25,1:1, record the particle diameter of gamlogic acid self-assembling polymers nanoparticle, PDI, envelop rate, drug loading such as following table
4。
Table 4
From table 4, medicine is increased to 1:1.25 with the ratio of material by 1:10, and envelop rate is gradually increased, in ratio 1:1.25
Time reach maximum.The amount continuing to increase medicine declines to ratio on the contrary to 1:1, envelop rate.Meanwhile, along with the increasing of amount of medicine
Add higher envelop rate.
The preparation of embodiment 5 gamlogic acid self-assembling polymers nanoparticle
Method, with embodiment 1, simply changes Polyethylene Glycol, record the particle diameter of gamlogic acid self-assembling polymers nanoparticle, PDI,
Envelop rate, drug loading such as table 5 below.
Table 5
The preparation method of embodiment 6 gamlogic acid self-assembling polymers nanoparticle
(1) preparation method is as follows:
1) prepared by polymeric material: by 0.04mol polyethylene glycol 6000,0.001mol 6-caprolactone, 0.0001mol stannous octoate
Join in three-necked bottle with 5ml toluene, at mechanical agitation and N2Under protection, 130 DEG C of oil bath reaction 12h；Reaction terminates
After, product naturally cools to room temperature, screws out toluene；Use dichloromethane lysate, after product all dissolves, will
It instills slowly in the coldest petroleum ether and precipitates, and filters, and precipitation is dissolved with dichloromethane again, is being slowly dropped into
In petroleum ether, repetitive operation, filter, obtain white product, 40 DEG C of vacuum drying, obtain polymeric material.
2) take 40mg gamlogic acid to be placed in eggplant type bottle, after adding the dissolving of 10ml acetonitrile, add 50mg polymeric material, again
Dissolve, utilize Rotary Evaporators to screw out acetonitrile, form one layer of pharmaceutical film on bottle wall after acetonitrile back-out, put into vacuum drying
In case, 40 DEG C of vacuum are overnight, remove trace acetonitrile, add 20ml pure water, carry out hydration process 4h, so at 65 DEG C
After solution is placed in ice-water bath, under 315W power ultrasonic 2 times, each 2min, ultrasonic end, cross 0.45 μm filter
Film, obtains gamlogic acid self-assembling polymers nanoparticle.
As it is shown in figure 1, as seen from Figure 1, nanoparticle particle diameter is that 217.7nm, PDI position 0.138 particle diameter closes in particle diameter distribution
Suitable, it is uniformly dispersed stable.
Observe nanoparticle form as in figure 2 it is shown, from Figure 2 it can be seen that nanoparticle globulate, form is homogeneous.
(2) application
The In-vitro release curves such as Fig. 3 of the gamlogic acid self-assembling polymers nanoparticle obtained, as seen from Figure 3, discharges slowly, holds
For a long time, gamlogic acid needs to diffuse out from hydrophobic core to enter back in surrounding medium.
The gamlogic acid self-assembling polymers nanoparticle obtained carries out anti tumor activity in vitro research.Research gamlogic acid and self assembly thereof gather
Compound nanoparticle all extracorporeal anti-tumor functions to human gastric cancer cells BGC-823 cell.The Carbazole alkaloid of nanoparticle when 24h
Rate is less than gamlogic acid crude drug (such as Fig. 4), but along with incubation time extends to 36h, 48h (such as Fig. 5-6), and nanoparticle thin
Born of the same parents' suppression ratio is higher than gamlogic acid crude drug.Visible, gamlogic acid self-assembled nanometer grain has preferable extracorporeal anti-tumor function, and tool
There is certain slow release effect.
The gamlogic acid self-assembling polymers nanoparticle obtained carries out rat Internal pharmacokinetics research.Give rat tail vein injection respectively
The gamlogic acid of doses and gamlogic acid self-assembling polymers nanoparticle, investigate its characteristics of pharmacokinetics, blood drug level change in time
Changing curve such as Fig. 7, contrast with gamlogic acid crude drug, gamlogic acid self-assembled nanometer grain mean residence time and half-life increase, clearly
Except rate reduces, the highest blood drug level improves, and has long circulating effect, illustrates to make gamlogic acid self-assembled nanometer grain, can change
Its metabolic process in rat body.
Claims (9)
1. the preparation method of a gamlogic acid self-assembling polymers nanoparticle, it is characterised in that preparation method is as follows:
1) prepared by polymeric material: join in three-necked bottle by Polyethylene Glycol, 6-caprolactone, stannous octoate and toluene, in stirring
And N2Under protection, 120-140 DEG C of oil bath reaction 10-14h；After reaction terminates, product naturally cools to room
Temperature, screws out toluene；Use dichloromethane lysate, after product all dissolves, be slowly dropped in petroleum ether
Row precipitation, sucking filtration, precipitation is dissolved with dichloromethane again, in being slowly dropped into petroleum ether, repetitive operation, filter,
Obtain white product, vacuum drying, obtain polymeric material；
2) take gamlogic acid to be placed in eggplant-shape bottle, after adding acetonitrile dissolving, add polymeric material, again dissolve, utilize rotation
Turning evaporimeter and screw out acetonitrile, acetonitrile forms one layer of pharmaceutical film on bottle wall after screwing out, and puts in vacuum drying oven 40 DEG C
Vacuum overnight, removes trace acetonitrile, adds pure water, carries out hydration process 2-8h, then will at 60-70 DEG C
Solution is placed in ice-water bath, under 135-315W power ultrasonic 2-6 time, each 2min, ultrasonic end, mistake
0.45 μm filter membrane, obtains gamlogic acid self-assembling polymers nanoparticle.
The preparation method of a kind of gamlogic acid self-assembling polymers nanoparticle the most according to claim 1, it is characterised in that: described
Polyethylene Glycol selected from Macrogol 2000, Macrogol 4000, polyethylene glycol 6000 and PEG 8000.
The preparation method of a kind of gamlogic acid self-assembling polymers nanoparticle the most according to claim 1, it is characterised in that: massage
That ratio, 6-caprolactone: Polyethylene Glycol=2:0.1～9:0.1.
The preparation method of a kind of gamlogic acid self-assembling polymers nanoparticle the most according to claim 3, it is characterised in that: massage
That ratio, 6-caprolactone: Polyethylene Glycol=4:0.1.
The preparation method of a kind of gamlogic acid self-assembling polymers nanoparticle the most according to claim 1, it is characterised in that: by matter
Amount ratio, gamlogic acid: polymeric material=1:5～1:1.25.
The preparation method of a kind of gamlogic acid self-assembling polymers nanoparticle the most according to claim 5, it is characterised in that: by matter
Amount ratio, gamlogic acid: polymeric material=1:1.25.
The preparation method of a kind of gamlogic acid self-assembling polymers nanoparticle the most according to claim 1, it is characterised in that: ultrasonic
Power is 315W.
The preparation method of a kind of gamlogic acid self-assembling polymers nanoparticle the most according to claim 1, it is characterised in that: ultrasonic
2 times, each 2min.
9. the gamlogic acid self-assembling polymers nanoparticle prepared according to the arbitrary described method of claim 1-8 is preparing antitumor drug
Application in preparation.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108478804A (en) * | 2018-05-08 | 2018-09-04 | 辽宁大学 | A kind of polyacrylic acid-S-S- block copolymer drugs and preparation method thereof |
| CN114767620A (en) * | 2022-03-16 | 2022-07-22 | 四川省医学科学院·四川省人民医院 | Multistage response injectable hydrogel loaded with gambogic acid and application thereof |
| CN116172961A (en) * | 2023-02-17 | 2023-05-30 | 中国中医科学院中药研究所 | Gambogic acid dimer self-assembled nanoparticle and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100453077C (en) * | 2007-03-12 | 2009-01-21 | 中国药科大学 | Injectable micelle prepn containing garcinolic acid and its prepn process |
| CN101229130B (en) * | 2008-02-03 | 2011-07-27 | 西北农林科技大学 | Isomorellic acid polylactic acid nano particle preparation and preparing method thereof |
| CN103142469A (en) * | 2013-03-15 | 2013-06-12 | 中国药科大学 | Application of using amphiphilic N-long-chain alkyl-N-arginine chitosan as solubilizing and absorption prompting carrier of gambogic acid |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108478804A (en) * | 2018-05-08 | 2018-09-04 | 辽宁大学 | A kind of polyacrylic acid-S-S- block copolymer drugs and preparation method thereof |
| CN114767620A (en) * | 2022-03-16 | 2022-07-22 | 四川省医学科学院·四川省人民医院 | Multistage response injectable hydrogel loaded with gambogic acid and application thereof |
| CN114767620B (en) * | 2022-03-16 | 2023-06-27 | 四川省医学科学院·四川省人民医院 | Gambogic acid-loaded multistage response injectable hydrogel and application thereof |
| CN116172961A (en) * | 2023-02-17 | 2023-05-30 | 中国中医科学院中药研究所 | Gambogic acid dimer self-assembled nanoparticle and preparation method and application thereof |
| CN116172961B (en) * | 2023-02-17 | 2023-08-25 | 中国中医科学院中药研究所 | Gambogic acid dimer self-assembled nanoparticle and preparation method and application thereof |
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