CN106983719A - A kind of docetaxel polymer nano micelle injection, its preparation method and its application in tumor is prepared - Google Patents
A kind of docetaxel polymer nano micelle injection, its preparation method and its application in tumor is prepared Download PDFInfo
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Abstract
The invention provides a kind of docetaxel polymer nano micelle injection, its preparation method and its application in tumor is prepared.The parts by weight of docetaxel 1 are included in the preparation；The parts by weight of nano-micelle polymer 10~100.The docetaxel nanometer micella uniform particle diameter, average grain diameter is 20~200nm.Said preparation can greatly increase the water solubility of docetaxel and the stability of preparation, extend the circulation time of docetaxel in blood, reduce the toxic side effect of commercial preparation, (EPR effects) passive target is acted on to tumor locus by strengthening infiltration and delay, so as to improve the antitumor curative effect of docetaxel, and polyethylene glycol (PEG) can be overcome (for example to treat the patient for having antibody to PEG as the inapplicable situation of the polymer nano micelle class preparation of shell or multiple dosing produces the patient of anti-PEG antibody).
Description
Technical field
The invention belongs to field of pharmaceutical preparations, it is related to a kind of docetaxel polymer nano micelle injection, preparation method
And its purposes in the medicine for the treatment of tumour.
Background technology
Docetaxel (Docetaxel) is the semi-synthetic paclitaxel derivatives of the second generation, and taxol is substituted using n-butanol base
On phenyl, mechanism of drug action is to promote tubulin polymerization and suppress microtubule depolymerization effect, forms stable non-functional micro-
Tube bank, so as to destroy tumour cell mitosis, suppresses growth of tumour cell.Docetaxel is taxol to the affinity of micro-pipe
2 times, so pharmacological action and activity it is stronger than taxol.Docetaxel shows in test cell line to be higher than taxol 2- in vitro
10 times of active anticancer, to lung cancer in non-cellule type, oophoroma, prostate cancer, advanced breast cancer, liver cancer and stomach cancer etc. are controlled
Therapeutic effect.
Docetaxel and taxanes seemingly, belong to insoluble medicine in water, and poorly water-soluble (about 10~20 μM) is presently commercially available
Injection docetaxel uses solubilizer Tween-80, and is dilution with 13% ethanol.Docetaxel toxic side effect includes nerve
Toxicity, bone toxicity and neutrophil reduction etc., are stayed and mistake while the solubilizer in preparation can produce serious body fluid contracting
Quick reaction etc..In addition to solubility, multidrug resistance is also the weight that another limitation taxanes clinical drug is used
Want factor.So presently relevant delivery system research is directed to improving the solubility of docetaxel, had no toxic side effect with new
Delivery media replace present tween solubilizer, and attempt to overcome multidrug resistance and increase docetaxel in tumor locus
Distribution and concentration, and reduce distribution of the docetaxel in normal structure, reduce toxicity.
Domestic and international researcher has done many researchs for the derivative and novel formulation of docetaxel, such as macromolecule is even
Join thing (macromolecule such as HPMA, Pluronic etc.)；Liposome nano granule；With block polymer micelle etc., to increase water solubility, though
Remarkable progress is so obtained in terms of preparation, but energy industrialized production and the kind for meeting safety evaluatio are rare at present.Though at present
Right liposomal paclitaxel formulation has been listed, but liposome docetaxel product is just in clinical stage.The many west of other albumin he
Match rule agent is in clinical research, but the cost of albumin preparation is higher.Block polymer micelle, listing report.
Nano-micelle preparations recent two decades turn into study hotspot by contrast.It can improve the solubility of medicine, control medicine
Thing discharges, and can also be modified to reach active targeting in micellar surface by EPR effect passive targets to tumor locus
Effect.Current nano-micelle preparations, which are mainly, uses amphipathic nature polyalcohol, and drugloading rate is higher, and stability is good.Amphipathic
Compound is block copolymer, including hydrophilic block and lipophilic block, and the nano-micelle of formation is core-shell structure, and hydrophilic block is table
The shell in face, can be scattered in water and physiological saline, and lipophilic block then forms the core of micella, for loading hydrophobic drug.Mesh
Preceding the most frequently used hydrophilic block is polyethylene glycol (PEG), and good water solubility, toxicity is low.But existed in 25% patient's body
Anti- PEG antibody (caused by containing substantial amounts of PEG in other daily chemical products such as shampoo and some food), and repeatedly giving
Anti- PEG antibody may be produced after medicine, is birdsed of the same feather flock together the clinical practice of compound micella so as to limit PEG.Lipophilic in amphiphilic polymers
Block is generally widely used polymer (such as polylactic acid-glycolic ethylhexyldithiophosphoric acid PLGA, poly- breast in the medicine and medical material that FDA ratifies
Sour PLA etc.).
The content of the invention
The purpose of the present invention is to overcome the deficiencies in the prior art to be noted there is provided a kind of docetaxel polymer nano micelle
Penetrate agent.
Amphipathic nature polyalcohol of the present invention employs poly- (2- methyl -2- oxazolines) or poly- (2- ethyl -2- oxazoles
Quinoline) as hydrophilic block to replace PEG, with PLA as lipophilic block, polymer nano micelle is used as to the load of docetaxel
Body, for a kind of clinical docetaxel polymer nano micelle injection for providing stabilization, can greatly increase the water-soluble of docetaxel
Property and preparation stability, extension docetaxel circulation time in blood, eliminate that the solubilizer poison in existing preparation is secondary to be made
With, and by EPR effect passive targets to tumor locus, so as to improve the antitumor curative effect of docetaxel, it is possible to overcome anti-
The problems such as antibody being produced after PEG antibody and multiple dosing, it is significant.
Technical scheme is as follows：
The parts by weight of docetaxel 1 are included in a kind of docetaxel polymer nano micelle injection, the preparation；Nanometre glue
The parts by weight of beam polymer 10~100.Preferably, the parts by weight of docetaxel 1 are included in the preparation；The weight of nano-micelle polymer 10
Measure part.
Described nano-micelle polymer is PEOz-PLA, i.e. PEOZ-PLA, or poly- (2-
Methyl -2- oxazolines)-PLA, i.e. PMOZ-PLA.
The PEOz PEOZ or poly- (2- methyl -2- oxazolines) the PMOZ degree of polymerization be 20~
60 units, mean molecule quantity is 1700 to 5100Da.Preferably, poly- (2- ethyl -2- oxazolines) PEOZ or poly-
(2- methyl -2- oxazolines) PMOZ degree of polymerization is 50 units, and mean molecule quantity is in 4400Da.
The degree of polymerization of the polylactic acid PLA is 30~115 units, and mean molecule quantity is 850 to 3300Da.Preferably,
The degree of polymerization of the polylactic acid PLA is 115 units, and mean molecule quantity is in 3300Da.
The average grain diameter of the docetaxel polymer nano micelle injection is 20~200nm.Preferably, it is described more western
The average grain diameter that he matches polymer nano micelle injection is 30~100nm.Most preferably, the docetaxel polymer nanocomposite
The average grain diameter of micella injection is 35nm.
The preparation method of described docetaxel polymer nano micelle injection, comprises the following steps：
1) docetaxel and nano-micelle polymer are dissolved in ethanol or acetonitrile respectively, are made into 10mg/ml storing solution, so
Docetaxel being measured according to prescription afterwards and nano-micelle polymer storing solution being mixed, vibration is mixed；
2) obtained docetaxel and nano-micelle mixed with polymers organic phase are injected into round-bottomed flask or other samples
Bottle in, in slightly heating process, decompression or normal pressure under organic solvent is slowly evaporated into it is completely dry, bottom of bottle formation medicine and
Nano-micelle polymeric material mixing film layer；
3) it is warming up to 35~50 degrees Celsius (preferably 45 degrees Celsius), adds distilled water or water for injection, slight oscillatory is extremely
Film layer is completely dissolved into settled solution；
4) settled solution is placed and is cooled to room temperature, 7000rpm is centrifuged 5 minutes, by many west of the unloaded in micella he
Match centrifugation remove, take supernatant to be freeze-dried the docetaxel polymer nano micelle injection freeze-dried powder.
Preferably, described preparation process 4) in, protective agent is added during freeze-drying, described freeze drying protectant is selected from sweet
Reveal any of alcohol, sucrose, lactose, trehalose, maltose and glucose or its mixture, the use of described freeze drying protectant
Measure as 5-20 grams/100 milliliters docetaxel polymer nano micelles.Docetaxel polymer can be increased by adding freeze drying protectant
The stability of micella injection, extends its term of validity.
Application of the described docetaxel polymer nano micelle injection in tumor is prepared, the tumour
For lung cancer in non-cellule type, breast cancer, oophoroma, prostate cancer, liver cancer or stomach cancer.
The present invention has the following technical effect that：
The preparation method for the docetaxel polymer nano micelle that the present invention is provided is simple, it is easy to operate, reproducible, can
Realize industrial-scale production.
The invention provides a kind of docetaxel polymer nano micelle injection, in treatment tumour, there is anti-PEG to resist
The purposes in the patient of PEG antibody is produced after the patient of body and multiple dosing, wherein it is preferred to, the tumour is non-small thin
Born of the same parents' property lung cancer, breast cancer, oophoroma, prostate cancer, liver cancer and stomach cancer etc..
Compared to existing injection docetaxel, the docetaxel polymer nano micelle that the present invention is provided has following excellent
Gesture：
1. described in polymeric material good biocompatibility, it is safe, will not produce and be made in existing preparation using Tween-80
Allergic reaction that solubilizer is brought, body fluid contracting such as stay at the toxic side effect.
2. the present invention contains docetaxel in polymer nano micelle, the water-soluble of docetaxel and stably is improved
Property, extend its term of validity.
3. the docetaxel polymer nano micelle particle diameter that the present invention is provided is smaller, tumor vessel can be effectively penetrated, is passed through
EPR effects are gathered in tumor locus, realize that passive target is acted on, so as to improve the therapeutic effect of medicine.
4. the docetaxel polymer nano micelle injection that the present invention is provided can greatly prolong docetaxel in blood
Circulation time, improve docetaxel Tissue distribution and characteristics of pharmacokinetics, greatly improve the antitumor curative effect of docetaxel, drop
Its low toxicity.
5. employed in the amphipathic nature polyalcohol that the docetaxel polymer nano micelle injection that the present invention is provided is related to
Poly- (2- methyl -2- oxazolines) or PEOz as hydrophilic block to replace PEG, its hydrophily and PEG phases
When, and have similar " stealth " effect with PEG, as the shell of micella, the kernel and contained medicine of micella can be both protected,
It can prevent again by the phagocytosis of mononuclear macrophage.
6. the docetaxel polymer nano micelle injection that the present invention is provided can overcome polyethylene glycol (PEG) as shell
The inapplicable situation of polymer nano micelle class preparation (for example treat the patient for having antibody to PEG or multiple dosing produced
The patient of anti-PEG antibody).
7. the preparation method for the docetaxel polymer nano micelle injection that the present invention is provided is easy using preparation method
Easy, extensively, product quality is stable, is easy to implement industrialized production for material source.And compared in clinical research
The pharmaceutical carrier (i.e. albumin) used in albumin injection docetaxel, cost is significantly reduced.
Brief description of the drawings
Fig. 1 is the docetaxel polymer nano micelle scanning electron microscope (SEM) photograph for preparing in the embodiment of the present invention.
Fig. 2 is the docetaxel polymer nano micelle injection freeze-dried powder redisperse liquid prepared in the embodiment of the present invention
Grain size distribution.
Fig. 3 is the docetaxel polymer nano micelle injection freeze-dried powder redisperse liquid for preparing in the embodiment of the present invention
Outer releasing curve diagram.
Fig. 4 is maximum resistance in nude mice for the docetaxel polymer nano micelle injection prepared in the embodiment of the present invention
By dose Zn-MT D (50mg/kg).
Fig. 5 is according to the docetaxel polymer nano micelle injection freeze-dried powder redisperse prepared in the embodiment of the present invention
Drug effect figure of the liquid in mouse tumor model.
Embodiment
With reference to embodiment, the present invention is further described, but the embodiment be not meant to be subject to the present invention it is any
Limitation.
Embodiment 1
In the present invention, the preparation of docetaxel polymer nano micelle comprises the following steps：
1) weigh docetaxel 10mg and add 1ml anhydrous hexanol ultrasonic dissolutions；Weigh PMOZ-PLA polymer 100mg additions
10ml absolute ethyl alcohol ultrasonic dissolutions；By docetaxel and PMOZ-PLA mixed with polymers.The PMOZ degree of polymerization is 50 units, is put down
Average molecular weight is in 4400Da.The degree of polymerization of polylactic acid PLA is 115 units, and mean molecule quantity is in 3300Da.
2) mixed liquor is added into 50 milliliters of round-bottomed flasks, depressurizes and slowly solvent volatilizees, and vacuumize under 40 degrees Celsius
To remove dissolvent residual, film layer (medicine+PMOZ-PLA polymer) is formed in round-bottomed flask bottom.
3) in the case of 45 degrees Celsius, 10 milliliters of distilled water is added, it is molten that slight oscillatory to film layer is completely dissolved into clarification
Liquid；
4) settled solution is placed and is cooled to room temperature, 7000rpm is centrifuged 5 minutes, by many west of the unloaded in micella he
Match centrifugation remove, take supernatant to be freeze-dried the docetaxel polymer nano micelle injection freeze-dried powder.
Docetaxel polymer nano micelle freeze-dried powder made from Example carries out the measure of envelop rate.
Chromatographic condition：Chromatographic column Nucleosil C18 (4.6mm X 250mm, 5 μm)；Mobile phase is acetonitrile-water=55:
45；Flow velocity 1ml/min；Detection wavelength 227nm；The μ 1 of sample size 20.
Docetaxel polymer nano micelle freeze-dried powder made from Example, adds distilled water redisperse into about 1 milli
Gram every milliliter of docetaxel concentration, takes 20 microlitres of dispersion liquid, adds 180 microlitres of acetonitriles, and vibration fully dissolving is then centrifuged for,
The μ 1 of supernatant 20 is taken in HPLC sample introductions.Standard docetaxel storing solution separately is taken, it is 10,20,50,100, and 200 to be made into concentration
Mcg/ml acetonitrile standard liquid, takes 20 μ 1 in HPLC sample introductions, curvilinear regression is carried out to gained peak area under each concentration respectively
Standard curve.By the docetaxel drug concentration in standard curve and nano-micelle freeze-dried powder redisperse liquid, calculate many
The envelop rate of Xi Tasai polymer nano micelles is 91.5%.
Docetaxel polymer nano micelle freeze-dried powder made from Example, adds distilled water redisperse into about 0.1
The docetaxel concentration of every milliliter of milligram, the docetaxel polymer nano micelle freeze-dried powder that a drop dilutes 500 times again is divided again
Dispersion liquid is dropped on copper mesh/carbon film, is placed 5 minutes, is removed unnecessary dispersion liquid, is added 1% uranyl acetate of stain 10 seconds, in
LEO EM910 transmission electron microscopes detect the form of nano-micelle under 80kV (see Fig. 1).Electronic Speculum result shows that nano-micelle is homogeneous
Spherical structure, particle diameter about 30nm.By 0.1 milligram of every milliliter of docetaxel polymer nano micelle freeze-dried powder redisperse liquid in horse
The particle diameter of micella is determined in your literary nanometer particle size instrument, the average grain diameter of acquisition is in 35nm, and decentralization is PDI=0.12 (see Fig. 2).
Precision pipettes the redisperse liquid 0.1ml of the docetaxel polymer nano micelle freeze-dried powder prepared in embodiment, puts
Enter in dialysis apparatus (molecular cut off is 3500), be put into beaker, dissolution medium is 1OOml PBSs；Temperature is set
For 37 degrees Celsius, horizontal slowly vibrating is sampled in 0.5, after 1,2,4,6,8,12 hours, measured respectively in dialysis apparatus with HPLC
The concentration for not discharging drug concentration docetaxel, calculate medicine accumulative release rate and the time make tablets in vitro curve, see
Fig. 3.
6-8 weeks Female nude mice is taken, 5-8x10 subcutaneously or at mammary fat pad is injected in mouse6Individual oophoroma A2780 is thin
Born of the same parents' (cell is scattered in 50% culture medium and 50% matrigel) or breast cancer MDA-MB-435 cells.Work as gross tumor volume
At about 200 cubic millimeters, mouse is assigned randomly in each treatment group to end of line intravenous injection administration of going forward side by side, dosage regimen is every
Inject once within four days, altogether four administrations.Treatment group includes physiological saline blank control group, docetaxel polymer nano micelle
With commercially available docetaxel injection.With the major diameter (a) and minor axis (b) of each nude mouse tumor of kind of calliper, by (a x b2)/2 are public
Formula calculates gross tumor volume.
As seen from Figure 4, the docetaxel polymer nano micelle prepared in the embodiment of the present invention in nude mice most
Big tolerance dose MTD is 50mg/kg, is 2.5 times of docetaxel commercial preparation (MTD is 20mg/kg).
As seen from Figure 5, the docetaxel polymer nano prepared in docetaxel commercial preparation and the embodiment of the present invention
Rice glue beam has good inhibiting effect to the tumour in nude mice MDA-MB-435 breast cancer models, two groups of preparation gross tumor volumes with
Control group is compared to significantly reducing, and the polymer nano micelle group with dosage compared with commercial preparation group has more preferable tumor killing effect (P
<0.05)。
Claims (8)
1. a kind of docetaxel polymer nano micelle injection, it is characterised in that：The weight of docetaxel 1 is included in the preparation
Part；The parts by weight of nano-micelle polymer 10~100；Described nano-micelle polymer is PEOz-poly- breast
Acid, i.e. PEOZ-PLA, or poly- (2- methyl -2- oxazolines)-PLA, i.e. PMOZ-PLA.
2. docetaxel polymer nano micelle injection according to claim 1, it is characterised in that：Poly- (the 2- second
Base -2- oxazolines) PEOZ or poly- (2- methyl -2- oxazolines) the PMOZ degree of polymerization is 20~60 units, mean molecule quantity
1700 to 5100Da.
3. docetaxel polymer nano micelle injection according to claim 1, it is characterised in that：The PLA
The PLA degree of polymerization is 30~115 units, and mean molecule quantity is 850 to 3300Da.
4. docetaxel polymer nano micelle injection according to claim 1, it is characterised in that：The docetaxel
The average grain diameter of polymer nano micelle injection is 20~200nm.
5. docetaxel polymer nano micelle injection according to claim 4, it is characterised in that：The docetaxel
The average grain diameter of polymer nano micelle injection is 30~100nm.
6. the preparation method of the docetaxel polymer nano micelle injection as any one of claim 1-5, it is special
Levy and be：The preparation method comprises the following steps：
1) docetaxel and nano-micelle polymer are dissolved in ethanol or acetonitrile respectively, are made into 10mg/ml storing solution, then press
Docetaxel and the mixing of nano-micelle polymer storing solution are measured according to prescription, vibration is mixed；
2) obtained docetaxel and nano-micelle mixed with polymers organic phase are injected into round-bottomed flask or other sample bottles,
In slightly heating process, organic solvent is slowly evaporated under decompression or normal pressure it is completely dry, in bottom of bottle formation medicine and nanometer
Micellar copolymerization thing material mixing film layer；
3) 35~50 degrees Celsius are warming up to, distilled water or water for injection is added, slight oscillatory to film layer is completely dissolved into clear
Clear solution；
4) settled solution is placed and is cooled to room temperature, 7000rpm is centrifuged 5 minutes, by docetaxel of the unloaded in micella from
The heart precipitation remove, take supernatant to be freeze-dried the docetaxel polymer nano micelle injection freeze-dried powder.
7. the preparation method of docetaxel polymer nano micelle injection according to claim 6, it is characterised in that：Institute
The preparation process 4 stated) in, protective agent is added during freeze-drying, described freeze drying protectant is selected from mannitol, sucrose, lactose, sea
Any of algae sugar, maltose and glucose or its mixture, the consumption of described freeze drying protectant is 5-20 grams/100 millis
Rise docetaxel polymer nano micelle.
8. the docetaxel polymer nano micelle injection as any one of claim 1-5 is preparing treatment tumour medicine
Application in thing, it is characterised in that：The tumour be lung cancer in non-cellule type, breast cancer, oophoroma, prostate cancer, liver cancer or
Stomach cancer.
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