CN104208030A - Albumin-combined taxol long-circulation nano-particle freeze-dried preparation - Google Patents
Albumin-combined taxol long-circulation nano-particle freeze-dried preparation Download PDFInfo
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Abstract
The invention provides an albumin-combined taxol long-circulation nano-particle freeze-dried preparation. Compared with a conventional taxol injecting solution and conventional albumin-combined taxol long-circulation nano-particles, the albumin-combined taxol long-circulation nano-particle freeze-dried preparation can improve a targeting performance of taxol on tumor, is enhanced in effects and is reduced in toxic and side effects. The invention also provides a preparation method of the albumin-combined taxol long-circulation nano-particle freeze-dried preparation.
Description
Technical field
The present invention relates to field of medicaments, be specifically related to a kind ofly to there is tumor-targeting and there is the albumin bound type effect of nano-paclitaxel lyophilized formulations of long circulating effect.
Background technology
Paclitaxel is a kind of secondary metabolite with anti-tumor activity extracted in Chinese yew genus plants, is white, tasteless crystallization or powder, is insoluble in water, is soluble in the organic solvents such as acetone, chloroform, ether.Paclitaxel is a complicated diterpene-kind compound, have the taxane-ring containing oxygen Fourth Ring and ester side chain, chemistry is by name: 5 β, 20-epoxy-1,2 α, 4,7 β, 1 β, 13 α-hexahydroxy taxane-11-alkene-9-ketone-4,10-diacetate esters-2-benzoate-13 [(2R, 3S)]-N-benzoyl-3-phenylisoserine ester, molecular formula is C
47h
51nO
14, molecular weight: 853.906.It was found in 1963 at american cancer institute, and Monroe E.Wall and Mansukh C.Wani has been separated to this material from Pacific Ocean Ramulus et folium taxi cuspidatae (Taxus brevifolia) bark, and called after paclitaxel.Paclitaxel antitumor mechanism promotes microtubule polymerization and stable is polymerized microtubule, make division fast tumor cell be firmly fixed at mitotic stages, microtubule no longer separates, can by cells blocks in G2 and the M phase, tumor cell is copied be obstructed and dead.Clinical research shows that paclitaxel is mainly applicable to ovarian cancer and breast carcinoma, also has certain curative effect to pulmonary carcinoma, colorectal cancer, melanoma, incidence cancer, lymphoma, cerebroma.Paclitaxel is the anticarcinogen of low toxicity, efficient, wide spectrum, and being one of the most effective medicine for the treatment of refractory ovarian, in treatment breast cancer disease, occupying critical role, is also the cancer therapy drug that existing market has the call and sales volume is maximum.
Formulation for paclitaxel the most conventional clinically is at present the paclitaxel injection of Bristol-Myers Squibb company
polyoxyethylene castor oil and dehydrated alcohol is adopted to make as mixed solvent.Polyoxyethylene castor oil in prescription can cause histamine release in body, causes systemic anaphylaxis to react, and incidence rate is 39%, and wherein serious anaphylaxis incidence rate is 2%.Majority is I allergic reaction type, shows as bronchospastic dyspnea, urticaria and hypotension.Other toxic and side effects comprise bone marrow inhibition, neurotoxicity, Cardiovascular Toxicity, gastrointestinal reaction, hepatotoxicity, alopecia etc.For avoiding anaphylaxis, take dexamethasone respectively in administration before 12 hours He before 6 hours, before administration 30 ~ 60 minutes oral and cetirizines of injection diphenhydramine, and will slowly instil during injection, the time of instiling is longer.Its toxic and side effects brought to the physiology of patient and psychological impact very large.
Injection paclitaxel albumin nano suspensoid (
aBI-007) be a kind of new type antineoplastic medicine of U.S. FDA approval in recent years, be used for the treatment of the metastatic breast cancer of recurrence in 6 months after the metastatic breast cancer of combined chemotherapy failure or adjuvant chemotherapy.ABI-007 is a kind of formulation for paclitaxel by human albumin stabilisation.It can be dispersed in very high paclitaxel concentration direct injection in normal saline solution, and not containing toxicity emulsifying agent, safety improves.Do not need the preconditioning in treating that Polyglucan reacts before medication, and can improve dose of paclitaxel, shorten the instillation time, in medicine effective percentage, reduction toxic and side effects, shortening administration time, comparatively paclitaxel injection improves a lot.
Overwhelming majority inside tumor angiogenic growth is irregular rapidly, inner lymphsystem is removed slow, there is tumor permeation enhancer, macromole and nano-particle is made easily to be trapped in inside tumor, be called " strengthening infiltration and retention effect " (Enhanced Permeability and Retention, EPR).Administration nano-drug administration system due to EPR effect can passive target to tumor.
After the quiet note of administration nano-drug administration system, major part is by mononuclear phagocyte system (MPS) picked-up, thus decreases the distribution at its hetero-organization and cell.If want the picked-up avoiding MPS, need to be improved administration nano-drug administration system by long circulating means.
Summary of the invention
Common white protein binding type effect of nano-paclitaxel is owing to modifying without long circulating, and passive target effect is poor.The invention provides a kind of albumin bound type paclitaxel long-circulating nanoparticles lyophilized formulations, retain the advantage of ABI-007 in preparation prescription, and on this basis, in safety range, add long circulating material, can further improve the tumor-targeting of formulation for paclitaxel, reduce toxic and side effects.
The invention discloses a kind of albumin bound type paclitaxel long-circulating nanoparticles lyophilized formulations and preparation method thereof.
In albumin bound type paclitaxel long-circulating nanoparticles lyophilized formulations, the amount of paclitaxel and the amount of adjuvant do not limit, preferred albumin bound type paclitaxel long-circulating nanoparticles lyophilized formulations contains the paclitaxel of 0.1% ~ 50% weight ratio, all the other are adjuvant, and the ratio of albumin and long circulating material is 2: 1 ~ 30: 1 weight ratio in adjuvant, preferably in adjuvant, the ratio of albumin and long circulating material is 5: 1 ~ 20: 1 weight ratio.The albumin bound type paclitaxel long-circulating nanoparticles compositions be made up of paclitaxel, albumin, long circulating material is when each component ratio is suitable and preparation method is suitable, can be free of other adjuvants, the lyophilized formulations obtained loosens, and is easily injected solvent dispersion.But in most cases; in albumin bound type paclitaxel long-circulating nanoparticles lyophilized formulations adjuvant except albumin and long circulating material; also containing based on other adjuvants improving face shaping, stability, heavy dispersibility, be selected from stabilizing agent, antioxidant, freeze drying protectant.
Albumin is selected from human serum albumin, bovine serum albumin, preferably human serum albumin.
Long circulating material is selected from polyethylene glycol fatty alcohol ether, cithrol, the phospholipid derivative of Polyethylene Glycol, the cholesterol derivative of Polyethylene Glycol, polyoxyethylene polyoxypropylene block copolymer, specifically be selected from PEG-DSPE 1500, cholesteryl succinyl polyethylene glycol 1500, poloxamer 188, polyoxyethylene sorbitan monoleate, polysorbate 60, polysorbate 20, Polyethylene Glycol (24) laurate, Polyethylene Glycol (40) laurate, Polyethylene Glycol (40) stearate, polyoxyethylene (40) Oleum Ricini, preferably from PEG-DSPE 1500, cholesteryl succinyl polyethylene glycol 1500, poloxamer 188, polyoxyethylene sorbitan monoleate.
Stabilizing agent is mainly attached to albumin surface, prevent albumin bound type paclitaxel long-circulating nanoparticles preparing, place, heavily dispersion time assemble, long circulating material can be played stably agent effect, and in addition, stabilizing agent can also be phospholipid.Phospholipid has a variety of.In the present invention, the phospholipid as stabilizing agent can be selected from PHOSPHATIDYL ETHANOLAMINE, Phosphatidylserine, phosphatidic acid, phosphatidyl glycerol, phosphatidylinositols, LYSOLECITHIN SUNLECITHIN A, sphingomyelins, Ovum Gallus domesticus Flavus lecithin, soybean lecithin, hydroxylated lecithin, hydrogenated phospholipid.
Antioxidant be prevent albumin bound type paclitaxel long-circulating nanoparticles preparing, place, heavily dispersion time composition be wherein oxidized.If control prescription composition, adjuvant specification, process conditions strict, oxidation also can be avoided, but usually adds the anti-oxidation of antioxidant in the formulation.Antioxidant is selected from vitamin C, vitamin C derivatives, coenzyme Q10, vitamin E, vitamin e derivative, sulfites, ethylenediaminetetraacetic acid and derivant thereof, cysteine hydrochloride.
Freeze drying protectant is the form maintaining albumin bound type paclitaxel long-circulating nanoparticles in freezing dry process, prevents nanoparticle from assembling, and when heavily disperseing, can dissolve rapidly and promoting to recover albumin bound type paclitaxel long-circulating nanoparticles aqueous suspension.Freeze drying protectant is selected from aminoacid, polysaccharide and polyhydric alcohol.Aminoacid is selected from alanine, valine, leucine, isoleucine, proline, tryptophan, phenylalanine, methionine, aspartic acid, glutamic acid, arginine, lysine, histidine.Polysaccharide is selected from trehalose, sucrose, lactose, maltose.Polyhydric alcohol selects mannitol, sorbitol, xylitol.
The preparation method of albumin bound type paclitaxel long-circulating nanoparticles lyophilized formulations adopts and is first prepared into albumin bound type paclitaxel long-circulating nanoparticles aqueous suspension, then obtains powder through lyophilization.The using method of albumin bound type paclitaxel long-circulating nanoparticles lyophilized formulations is mixed homogeneously with solvent for injection by lyophilized formulations, then inject.Injection solvent is selected from water for injection, normal saline, glucose solution, phosphate buffer, acetate buffer, preferably water for injection.
The preparation method of albumin bound type paclitaxel long-circulating nanoparticles aqueous suspension does not limit, as long as obtain corresponding albumin bound type paclitaxel long-circulating nanoparticles, and meeting lyophilization below, to prepare lyophilized formulations in good condition just passable, the optional autohemagglutination of preparation method is legal, the sedimentation method, solvent evaporation method, salting out method, high pressure homogenization method, emulsion process, the preferably white sedimentation method, high pressure homogenization method, more preferably high pressure homogenization method.These preparation methoies can with reference to relevant speciality books and document, is designed and operation completes by professional and technical personnel.
Albumin bound type paclitaxel long-circulating nanoparticles in the present invention, its particle diameter is 1 ~ 1000 nanometer, preferably 10 ~ 600 nanometers, more preferably 90 ~ 200 nanometers.
Albumin bound type paclitaxel long-circulating nanoparticles lyophilized formulations can be used for the malignancy diseases such as treatment nonsmall-cell lung cancer, cancer of pancreas, breast carcinoma, ovarian cancer.
Accompanying drawing explanation
Fig. 1. albumin bound type paclitaxel long-circulating nanoparticles lyophilized formulations photo
Fig. 2. albumin bound type paclitaxel long-circulating nanoparticles transmission electron microscope picture
Fig. 3. albumin bound type paclitaxel long-circulating nanoparticles particle size determination figure
Fig. 4. albumin bound type paclitaxel long-circulating nanoparticles Zeta potential figure
Fig. 5. the drug entities distribution of albumin bound type effect of nano-paclitaxel
Fig. 6. the drug entities distribution of albumin bound type paclitaxel long-circulating nanoparticles
Detailed description of the invention
Embodiment 1. blank albumin bound type long-circulating nanoparticles
Get 300mg human serum albumin to be dissolved in 30ml water, then add the slow stirring and dissolving of 150mg PLURONICS F87, add the jolting of 1ml chloroform, leave standstill, be separated chloroform, repeat 3 times, make albumin aqueous solution saturated by chloroform; Get chloroform 0.55ml and dehydrated alcohol 0.05ml to mix, and dropwise instill in albumin aqueous solution, stir with high speed disperser, to stir after 10 seconds interval 2 seconds, totally 2 minutes, formation colostrum; Move to high pressure homogenizer mesohigh breast even, circulate 5 times under 3000psi, obtain nano-emulsion; Nano-emulsion Rotary Evaporators is volatile organic solvent below 37 DEG C, and the suspension obtained is translucent shape, and be transferred in 5ml cillin bottle, 1ml/ props up, and separately adds the mannitol of 1ml20%, and mixing, is blank albumin bound type long-circulating nanoparticles.
Embodiment 2. albumin bound type effect of nano-paclitaxel
Get 300mg human serum albumin to be dissolved in 30ml water, add the jolting of 1ml chloroform, leave standstill, be separated chloroform, repeat 3 times, make albumin aqueous solution saturated by chloroform; Get chloroform 0.55ml and dehydrated alcohol 0.05ml to mix, dissolve 50mg paclitaxel, and dropwise instill in albumin aqueous solution, stir with high speed disperser, to stir after 10 seconds interval 2 seconds, totally 2 minutes, formation colostrum; Move to high pressure homogenizer mesohigh breast even, circulate 5 times under 3000psi, obtain nano-emulsion; Nano-emulsion Rotary Evaporators is volatile organic solvent below 37 DEG C, and the suspension obtained is translucent shape, and be transferred in 5ml cillin bottle, 1ml/ props up, and separately adds the mannitol of 1ml20%, and mixing, is albumin bound type effect of nano-paclitaxel.
Embodiment 3. albumin bound type paclitaxel long-circulating nanoparticles lyophilized formulations
Get 300mg human serum albumin to be dissolved in 30ml water, then add the slow stirring and dissolving of 150mg PLURONICS F87, add the jolting of 1ml chloroform, leave standstill, be separated chloroform, repeat 3 times, make albumin aqueous solution saturated by chloroform; Get chloroform 0.55ml and dehydrated alcohol 0.05ml to mix, dissolve 50mg paclitaxel, and dropwise instill in albumin aqueous solution, stir with high speed disperser, to stir after 10 seconds interval 2 seconds, totally 2 minutes, formation colostrum; Move to high pressure homogenizer mesohigh breast even, circulate 5 times under 3000psi, obtain nano-emulsion; Nano-emulsion Rotary Evaporators is volatile organic solvent below 37 DEG C, the suspension obtained is translucent shape, be transferred in 5ml cillin bottle, 1ml/ props up, separately add the mannitol of 1ml20%, mixing, carries out lyophilization operation with in freezer dryer, obtain loose white powder, be albumin bound type paclitaxel long-circulating nanoparticles lyophilized formulations.
The outward appearance of albumin bound type paclitaxel long-circulating nanoparticles lyophilized formulations is white (Fig. 1).Observing albumin bound type paclitaxel long-circulating nanoparticles under transmission electron microscope is uniform-spherical structure (Fig. 2), and particle diameter is 104.4nm (Fig. 3), and Zeta potential is-26.7mV (Fig. 4).This lyophilized formulations often props up and adds jolting after 2ml water for injection, can be dispersed into rapidly uniform suspension.
PLURONICS F87 is changed into PEG-DSPE 1500, cholesteryl succinyl polyethylene glycol 1500, polyoxyethylene sorbitan monoleate, other operations are consistent, and the nanoparticle obtained measures its particle diameter, all at below 150nm.
The pharmacodynamic evaluation of experimental example 1. albumin bound type paclitaxel long-circulating nanoparticles
Material: (1) commercially available paclitaxel injection; (2) according to blank albumin bound type long-circulating nanoparticles prepared by embodiment 1; (3) according to albumin bound type effect of nano-paclitaxel prepared by embodiment 2; (4) albumin bound type paclitaxel long-circulating nanoparticles lyophilized formulations is prepared according to embodiment 3, every albumin bound type paclitaxel long-circulating nanoparticles only heavily disperseed after adding water for injection 2ml.
Animal: C57BL/6 female mice 50, body weight is 22.1 ± 2.1 grams, 50 ~ 60 days ages of Mus.Raise 7 days at SPF level Animal House adaptability, in whole experimentation, each group Mus freely drinks water all on an equal basis, ingests, and breeding observing room keeps 20 ~ 24 DEG C, relative humidity 70% ~ 80%.
Method and result: the Lewis lung cancer cell getting well-grown exponential phase, becomes unicellular with 0.25% trypsin digestion and cell, after phosphate buffer washes twice, by cell count method, are 1 × 10 with normal saline adjustment cell concentration
7individual/ml, often only subcutaneous vaccination 0.1ml outside healthy C57BL/6 mice right hind.Normal raising is the success of animal inoculation tumor after 8 days.Measure tumor footpath every day, choose the tumor-bearing mice 50 that tumor major diameter is about 5.5-6.5mm, be divided into 5 groups at random.The cropping of tumor-bearing mice health different parts gives labelling, is labeled as respectively: (1) model group; (2) model+paclitaxel injection group; (3) model+blank albumin bound type long-circulating nanoparticles group; (4) model+albumin bound type effect of nano-paclitaxel group; (5) model+albumin bound type paclitaxel long-circulating nanoparticles group.
Every animal pattern tail vein injection medicine, dosage is 20mg/kg, 1 times/day, continuous tail vein injection 3 days.Model group tail vein injection saline.After medication terminates, put to death each treated animal in the 14th day.Complete separation Subcutaneous tumor tissue, weighs tumor, carries out statistical procedures, calculates the heavy tumour inhibiting rate of each group of tumor.
Heavy tumour inhibiting rate=(the average tumor weight of 1-medicine group average tumor weight/matched group) × 100% of tumor
Table 1. albumin bound type paclitaxel long-circulating nanoparticles is to the tumor killing effect of Lewis lung cancer model mice
*, p < 0.05, compares with model group
#, p < 0.05, compares with model+paclitaxel injection group
△, p < 0.05, compares with model+albumin bound type effect of nano-paclitaxel group
From tumor killing effect, albumin bound type paclitaxel long-circulating nanoparticles > albumin bound type effect of nano-paclitaxel > paclitaxel injection.The tumor-inhibiting action of albumin bound type paclitaxel long-circulating nanoparticles group is significantly better than commercially available paclitaxel injection group, common white protein binding type effect of nano-paclitaxel group.Therefore, after adding long circulating material, the antitumor drug effect of effect of nano-paclitaxel significantly improves.
The drug entities distribution of experimental example 2. albumin bound type paclitaxel long-circulating nanoparticles
Material: the albumin bound type effect of nano-paclitaxel that (1) prepares according to embodiment 2; (4) albumin bound type paclitaxel long-circulating nanoparticles lyophilized formulations is prepared according to embodiment 3, every albumin bound type paclitaxel long-circulating nanoparticles only heavily disperseed after adding water for injection 2ml.
Method and result: set up bearing mouse model with experimental example 1.Choose the tumor-bearing mice 24 that tumor major diameter is about 5.5-6.5mm, be divided into 2 groups at random.Be respectively albumin bound type effect of nano-paclitaxel group and albumin bound type paclitaxel long-circulating nanoparticles group, often organize 12.
Tail vein injection is administered once, and dosage is 20mg/kg, respectively at 0.5,1,1.5,2h tail venous blood sampling 80 μ l is in the plastic centrifuge tube of heparin sodium process.Each time point puts to death 3 animals, dissects immediately, gets liver, kidney, tumor, claims tissue wet, the weight normal saline such as to add and carries out homogenate, with the centrifugal 10min of 8000rpm, gets the supernatant Taxol Power by HPLC content set up.After albumin bound type effect of nano-paclitaxel group intravenously administrable, remove rapidly in blood, mainly be distributed in the abundant hepatic tissue of macrophage, after administration 0.5h, in liver, concentration reaches 75.11 μ g/g, slightly low at the drug level of kidney and tumor locus, be respectively 18.99 μ g/g and 19.98 μ g/g.Based on EPR effect, medicine has certain accumulation (Fig. 5) in tumor.Albumin bound type paclitaxel long-circulating nanoparticles group is after tail intravenously administrable, same time point compares with albumin bound type effect of nano-paclitaxel group, distribution in tumor tissues is obviously increased, after administration 0.5h, in tumor tissues, concentration reaches 28.77 μ g/g, in liver, concentration is down to 64.61 μ g/g by 75.11 original μ g/g, illustrates that adding of long circulating material improves the distribution of paclitaxel in tumor, has played cancer target effect (Fig. 6).
Claims (10)
1. an albumin bound type paclitaxel long-circulating nanoparticles lyophilized formulations.
2. albumin bound type paclitaxel long-circulating nanoparticles lyophilized formulations as claimed in claim 1, the paclitaxel containing 0.1% ~ 50% weight ratio, all the other are adjuvant, and in adjuvant, the ratio of albumin and long circulating material is 2: 1 ~ 30: 1 weight ratio.
3. albumin bound type paclitaxel long-circulating nanoparticles lyophilized formulations as claimed in claim 2, wherein in adjuvant except albumin and long circulating material, also containing other adjuvants, be selected from stabilizing agent, antioxidant, freeze drying protectant.
4. albumin bound type paclitaxel long-circulating nanoparticles lyophilized formulations as claimed in claim 2, albumin is selected from human serum albumin, bovine serum albumin.
5. albumin bound type paclitaxel long-circulating nanoparticles lyophilized formulations as claimed in claim 2, long circulating material is selected from polyethylene glycol fatty alcohol ether, cithrol, the phospholipid derivative of Polyethylene Glycol, the cholesterol derivative of Polyethylene Glycol, polyoxyethylene polyoxypropylene block copolymer.
6. albumin bound type paclitaxel long-circulating nanoparticles lyophilized formulations as claimed in claim 3, stabilizing agent is phospholipid, and is selected from PHOSPHATIDYL ETHANOLAMINE, Phosphatidylserine, phosphatidic acid, phosphatidyl glycerol, phosphatidylinositols, LYSOLECITHIN SUNLECITHIN A, sphingomyelins, Ovum Gallus domesticus Flavus lecithin, soybean lecithin, hydroxylated lecithin, hydrogenated phospholipid.
7. albumin bound type paclitaxel long-circulating nanoparticles lyophilized formulations as claimed in claim 3, freeze drying protectant is selected from aminoacid, polysaccharide and polyhydric alcohol.
8. albumin bound type paclitaxel long-circulating nanoparticles lyophilized formulations as claimed in claim 1, its preparation method adopts and is first prepared into albumin bound type paclitaxel long-circulating nanoparticles aqueous suspension, then obtains powder through lyophilization.
9. albumin bound type paclitaxel long-circulating nanoparticles lyophilized formulations as claimed in claim 8, wherein the preparation method of albumin bound type paclitaxel long-circulating nanoparticles aqueous suspension is selected from polymerization, the sedimentation method, solvent evaporation method, salting out method, high pressure homogenization method, emulsion process, preferred autoprecipitation method, high pressure homogenization method.
10. albumin bound type paclitaxel long-circulating nanoparticles lyophilized formulations as claimed in claim 1, its particle diameter is 1 ~ 1000 nanometer.
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