CN102397553B - Method for improving drug release in carbon nano tube drug delivery system by displacement object - Google Patents
Method for improving drug release in carbon nano tube drug delivery system by displacement object Download PDFInfo
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Abstract
The invention discloses a method for improving drug release in a carbon nano tube drug delivery system by a displacement object. Based on a mechanism of loading drugs of a carbon tube cavity, one or a plurality of displacement objects are loaded when the drugs are loaded, the displacement objects can reduce the surface tension of a solution or the acting force of the displacement objects and the carbon nano tube cavity is stronger than the acting force of the drugs and the tube cavity so as to overcome the energy barrier of the drugs released from the carbon nano tube cavity and weaken the acting force between the drugs and the tube cavity, and the purpose of promoting drug release is achieved. After adding the displacement objects promoting release, the 24-hour accumulated release degree of the drugs is increased to 70-80% with the displacement objects from 10% without the displacement objects. The method solves the problem of drug release in the carbon tube cavity, is simple and feasible, and overcomes the defect of inconvenience in operation because light, heat and other external drives are released on an organism. Because of the improvement of the drug release, a plurality of drugs can be loaded in a tube cavity loading mode, and the application of carbon nano tubes in the drug delivery system can be greatly increased.
Description
Technical field
The present invention relates to carbon nanotubes application, particularly the solution of CNT drug delivery system Chinese medicine release.
Background technology
CNT (Carbon Nanotubes, CNTs) be that the S.Iijima of Japanese NEC Corporation in 1991 finds when preparing the fullerene product with the electron microscope observation graphite acr method, it can be regarded as by the Graphene synusia is the body of seamless, the hollow of nanoscale around central shaft by the curling diameter that forms of certain helical angle, and its two ends are formed by fullerene hemisphere sealing cap.(radial dimension is nanometer scale to CNT because structure is more special, axial dimension is that seal basically at micron dimension, pipe two ends), have unique hollow structure and nanometer caliber, its internal cavities can hold high amount of drug, in a single day two ends are opened, its open end becomes controls the passage that medicine discharges, the more important thing is, CNTs can be with medicine and the environment isolation of its carrying, thereby the protection medicine is avoided the destruction of body endoenzyme etc. in the process of sending, with the medicine safe shipment in cell; Also have in addition the lot of documents report to show that CNTs can enter cell and subcellular organelle by number of ways and mechanism.Although original CNTs is dissolved in any solvent hardly, and easily assemble bunchy in solution, but utilize physics or chemical method to modify processing to its surface, change its surface group and physicochemical property, can improve the dispersibility of CNTs, and strengthen the compatibility of itself and body.Moreover, the CNTs surface is modified can also practical function, CNTs after functionalization not only keeps original specific physique, and the functional group of decorating molecule also has the activity of further reaction, and modifying for CNTs further (targeting) provides possibility.
At present the CNTs medicine-carrying method that is used for drug delivery system mainly contains three kinds: the first is that the CNTs after medicine and functionalization is connected by covalent bond, after administration, covalent bond fracture under the effect of enzyme etc. in vivo, discharge medicine performance drug effect, this method will be passed through multistep reaction, the chemical reagent that uses is many, is unfavorable for environmental protection and large production application; The second is that the CNTs after functionalization is combined by non-covalent mode with medicine, in this case, medicine can interact by π-π and be deposited in the outer wall of CNTs, but this effect has certain limitation, namely require medicine to have the conjugation aromatic rings, the large π key of delocalization is arranged, concerning a lot of medicines, can not satisfy this structural requirement; The third is that medicine is seated in the tube chamber of CNTs by certain method and means, and this method can overcome the deficiency of front two kinds of methods, and its medicine carrying process is a physical process, need not use chemical reagent; Most of drug molecule can be loaded into suitable CNTs tube chamber.Moreover, drug encapsulation after the tube chamber of CNT, due to the protective effect of tube chamber, also can make some easily degraded by enzymes or medicine that the stable pH of being subjected to affects avoid destroying; Efflux the medicine of substrate for the P-glycoprotein inhibitors, owing to being loaded on tube chamber, also can avoiding P-gp and efflux.The lot of documents report is arranged, and the driving force when medicine is loaded into carbon nanotubes lumen is capillarity, secondly due to the difference of various molecular properties, also has Van der Waals force and hydrophobic interaction power etc.Capillarity namely when the object that contains trickle gap contacts with liquid, under Infiltrating liquid along rising on the gap or infiltrate, the phenomenon that liquid descends along the gap under Infiltrating not; Its size is directly proportional to the surface tension of this liquid, is inversely proportional to capillary radius.And the moistening of the surface of solids refers to that the upper a kind of fluid in surface is by process that one other fluid replaced.During moistening liquid to the adhesive force of the surface of solids greater than its cohesiveness; When nonwetting liquid to the adhesive force of the surface of solids less than its cohesiveness.After medicine is loaded into the nanotube tube chamber, obstruction due to mouth of pipe energy barrier, and the nanometer dimension of tube chamber, the complexity of medicine and tube chamber interphase interaction, medicine discharges very difficult from tube chamber, up to the present, how the thing inside tube chamber being discharged is still a difficult problem, this has limited the application of CNTs in drug delivery greatly, is also that the application of this easy medicine-carrying method is far from the main cause of front two kinds of methods.
Improve the release of carbon pipe Chinese medicine, mainly contain at present following several approach: 1) external trigger, as: electric field, magnetic field, machinery, light, heat, but these means are not easy realization, and it is very inconvenient using especially in vivo; 2) improve the essential nature of pipe: as increasing hole number on pipe, reducing the space multistory steric hindrance of modification group on tube wall etc.Concerning single-walled pipe, can destroy its structural pipe wall by chemical modification, be figuratively speaking to burrow on tube wall, can make drug release like this; For multi-walled pipes, general various modifying and decorating (except the tube chamber filling) can only carry out modifying destruction to outermost one deck or the mouth of pipe of its pipe, the change of this structure does not reach tube chamber, although this modification meeting is due to the character of modification group and sterically hindered etc. make mouth of pipe energy barrier that certain variation be arranged, some and carbon pipe tube chamber are interacted strong medicine, and this variation can't make it discharge from tube chamber.
The present invention solves medicine and discharge principle---the capillarity that is based on CNTs tube chamber medicine carrying from the CNTs tube chamber.After medicine enters tube chamber, luminal surface is had an adhesive force, if can by certain method change medicine to the adhesive force of luminal surface to a certain degree, can make its release.By being written into simultaneously another kind of material, make the effect of itself and CNTs tube chamber be better than drug molecule as (1), weakened the effect between medicine and wall of the lumen, so just the medicine displacement can be gone out tube chamber, thereby improve the release of medicine.(2) (with) or being written into simultaneously a kind of material, this substance produces enough large driving force such as osmotic pressure etc., and this power can overcome active force between medicine and tube chamber and mouth of pipe energy barrier to the obstruction of drug release.Due to the improvement of drug release, utilize the carbon nanotubes lumen drug loading to be used widely.
Summary of the invention
The present invention realizes that the technical scheme of each purpose comprises following several step:
1. the carboxylated modification of original CNT:
Get CNT (three kinds of calibers) appropriate, add 0.1～2 times of amount H
2SO
4/ HNO
3Mixed liquor, water-bath (room temperature～50 ℃) are after ultrasonic 12～36 hours, and to neutrality, 50-80 ℃ of vacuum drying collected black powder, namely gets carboxylic carbon nano-tube (CNT-COOH) with deionized water wash.
2. carboxylic carbon nano-tube medicine carrying:
It is appropriate that precision takes CNT-COOH, puts in cillin bottle; Preparation finite concentration verapamil aqueous solution and hydroxy camptothecin alcoholic solution, precision pipettes this solution and adds respectively in above-mentioned cillin bottle and weighed weight, ultrasonic 5 minutes rearmounted room temperatures (25～30 ℃) constant temperature jolting 24 hours, through 0.1 μ m membrane filtration, get subsequent filtrate and measure the content of its Chinese medicine in accordance with the law, by calculating the drug loading of CNT; Collecting filtering residue vacuum decompression drying is the CNT drug-loading system.Result shows that the drug loading of CNT-COOH of internal diameter 2～5nm is the highest.
3. the impact of displacement object on the release of CNT delivery system Chinese medicine
Get a certain amount of CNT-COOH, evacuation is 0.5～1 hour while stirring, then add medicine and displacement object mixed solution or the molten mixture of (or not adding displacement object), evacuation is no less than 3 hours to continue to stir also after continuing evacuation and be stirred to solvent to volatilize again, product is fast with certain solvent wash and be settled to certain volume, calculate the content of this solution Chinese medicine, filter residue and drying is got and is carried out in right amount the release investigation in accordance with the law.
4. vitro release investigation method
Get displacement object and without the CNT drug-loading system of displacement object, adopt the first method in dissolution method (2010 editions two appendix XD of Chinese Pharmacopoeia), take the degassed deionized water of 150mL as dissolution medium, rotating speed is 75rpm, operation, got respectively liquid 1mL, 0.22 μ m filtering with microporous membrane at 1,2,4,6,8,12,24 hour in accordance with the law, high performance liquid chromatography is surveyed the content of subsequent filtrate Chinese medicine in accordance with the law, and in time replenishes dissolution medium 1mL of the same race in process container.
Description of drawings
Fig. 1 is the envelop rate figure that in embodiment 1, different tube diameters CNT-COOH carries verapamil
Fig. 2 is the envelop rate figure that in embodiment 2, different tube diameters CNT-COOH carries hydroxy camptothecin
Fig. 3 carries the drug release curve chart of verapamil delivery system without the CNT-COOH of displacement object in embodiment 3
Fig. 4 is that in embodiment 4, poloxamer F68 is the drug release curve chart that the CNT-COOH of displacement object carries the verapamil delivery system
Fig. 5 is that in embodiment 5, PEG4000 is the drug release curve chart (n=3) that the CNT-COOH of displacement object carries the verapamil delivery system
Fig. 6 is that in embodiment 6, lactose is the drug release curve chart (n=3) that the CNT-COOH of displacement object carries the verapamil delivery system
The specific embodiment
The present invention is described further below in conjunction with embodiment, rather than limit the scope of the invention.
Embodiment 1:CNT-COOH carries the preparation of water soluble drug verapamil hydrochloride delivery system
Get original MWCNT 100mg, add 40mL H
2SO
4/ HNO
3(V/V=3/1) mixed liquor, ultrasonic 24 hours of water-bath (30～40 ℃) is with the dilution of 120mL deionized water, the standing liquid of crossing, sucking filtration, filtering residue with deionized water dialyse be neutrality to liquid after, water bath method is collected black powder, namely gets carboxylic carbon nano-tube (CNT-COOH).Investigated the dissolution of CNT-COOH in different solvents, result shows, CNT-COOH dissolution in water and DMF, DMSO, 50% ethanol, 75% ethanol, 95% ethanol is good.The method of process acid base titration records wherein, and the content of carboxyl is 1.5mmol/g.Precision takes CNT-COOH 10mg, puts in cillin bottle; Prepare the verapamil aqueous solution of 100 μ g/mL, precision pipettes this solution 10.0mL, add in above-mentioned cillin bottle, sealing, ultrasonic 5 minutes rearmounted constant temperature (25 ± 2 ℃) jolting 24 hours, through 0.15 μ m membrane filtration, get the content that subsequent filtrate is measured its Chinese medicine in accordance with the law, by calculating the drug loading of CNT; Collecting filtering residue vacuum decompression drying is the CNT drug-loading system.
Embodiment 2:CNT-COOH carries the preparation of fat-soluble medicine hydroxy camptothecin delivery system
Get original MWCNT 100mg, add 40mLH
2SO
4/ HNO
3(V/V=3/1) mixed liquor, ultrasonic 24 hours of water-bath (30～40 ℃) is with the dilution of 120mL deionized water, the standing liquid of crossing, sucking filtration, filtering residue with deionized water dialyse be neutrality to liquid after, water bath method is collected black powder, namely gets carboxylic carbon nano-tube (CNT-COOH).Precision takes CNT-COOH 10mg, puts in cillin bottle; Prepare the hydroxy camptothecin alcoholic solution of 50 μ g/mL, precision pipettes this solution 10.0mL, add in above-mentioned cillin bottle, sealing, ultrasonic 5 minutes rearmounted constant temperature (25 ± 2 ℃) jolting 24 hours, through 0.1 μ m membrane filtration, get the content that subsequent filtrate is measured its Chinese medicine in accordance with the law, by calculating the drug loading of CNT; Collecting filtering residue vacuum decompression drying is the CNT drug-loading system.
Embodiment 3: the preparation of carrying the verapamil hydrochloride delivery system without the CNT-COOH of displacement object
Precision takes CNT-COOH 89.6mg and puts in reaction bulb, and evacuation is 1 hour while stirring; With verapamil hydrochloride 86.3mg, add a small amount of deionized water and make into the solution shape, get A liquid, A liquid is added in the CNT-COOH reaction bulb that evacuation processes, continues to keep vacuum also to stir 2 hours, then after being heated to solvent under the vacuum stirring state and volatilizing, product is fast with washing with alcohol and be settled to 50mL, calculate the content of this solution Chinese medicine, filter residue and drying, the CNT-COOH that namely gets without displacement object carries verapamil hydrochloride delivery system 123.71mg.
Embodiment 4: the CNT-COOH take poloxamer F68 as displacement object carries the preparation of verapamil hydrochloride delivery system
Precision takes CNT-COOH 99.3mg and puts in reaction bulb, and evacuation is 1 hour while stirring; To add verapamil hydrochloride 99.6mg after poloxamer F680.4g melting, add a small amount of deionized water and make into the solution shape, get A liquid, A liquid is added in the CNT-COOH reaction bulb that evacuation has been processed, continue keep vacuum and stirred 2 hours, then after being heated to solvent under the vacuum stirring state and volatilizing, product is fast with washing with alcohol and be settled to 50mL, calculate the content of this solution Chinese medicine, filter residue and drying, the CNT-COOH that namely is able to poloxamer F68 and is displacement object carries verapamil hydrochloride delivery system 242.1mg.
Embodiment 5: the CNT-COOH take PEG4000 as displacement object carries the preparation of verapamil hydrochloride delivery system
Precision takes CNT-COOH 100mg and puts in reaction bulb, and evacuation is 1 hour while stirring; Verapamil hydrochloride 100mg will be added after the PEG40000.4g melting, add a small amount of deionized water and make into the solution shape, get A liquid, A liquid is added in the CNT-COOH reaction bulb that evacuation has been processed, continue keep vacuum and stirred 2 hours, then after being heated to solvent under the vacuum stirring state and volatilizing, product is fast with deionized water wash and be settled to 50mL, calculate the content of this solution Chinese medicine, filter residue and drying, the CNT-COOH that namely is able to PEG4000 and is displacement object carries verapamil hydrochloride delivery system 236.6mg.
Embodiment 6: the CNT-COOH take lactose as displacement object carries the preparation of verapamil hydrochloride delivery system
Precision takes CNT-COOH 100.2mg and puts in reaction bulb, and evacuation is 1 hour while stirring; The 5g lactose is mixed with saturated solution, add verapamil hydrochloride 99.9mg, add a small amount of deionized water and make into the solution shape, get A liquid, A liquid is added in the CNT-COOH reaction bulb that evacuation has been processed, continue keep vacuum and stirred 2 hours, then after being heated to solvent under the vacuum stirring state and volatilizing, product is fast with deionized water wash and be settled to 50mL, calculate the content of this solution Chinese medicine, filter residue and drying, the CNT-COOH that namely is able to lactose and is displacement object carries verapamil hydrochloride delivery system 1.1476g.
Embodiment 7: the CNT-COOH take alkyl polyglucoside as displacement object carries the preparation of verapamil hydrochloride delivery system
Precision takes CNT-COOH 100mg and puts in reaction bulb, and evacuation is 1 hour while stirring; With alkyl polyglucoside 0.4g and verapamil hydrochloride 100mg, add a small amount of deionized water and make into the solution shape, get A liquid, A liquid is added in the CNT-COOH reaction bulb that evacuation processes, continues to keep vacuum also to stir 2 hours, then after being heated to solvent under the vacuum stirring state and volatilizing, product is fast with deionized water wash and be settled to 50mL, calculate the content of this solution Chinese medicine, filter residue and drying, the CNT-COOH that namely is able to alkyl polyglucoside and is displacement object carries the verapamil hydrochloride delivery system.
Embodiment 8: carry the preparation of verapamil hydrochloride delivery system as the CNT-COOH of displacement object take poloxamer and PEG4000 mixture
Precision takes CNT-COOH 100mg and puts in reaction bulb, and evacuation is 1 hour while stirring; with a certain proportion of poloxamer and PEG4000 mixture (W/W) 0.4g and verapamil hydrochloride 100mg, heat and add a small amount of deionized water and make into the solution shape, get A liquid, A liquid is added in the CNT-COOH reaction bulb that evacuation has been processed, continue heating, evacuation and be stirred to solvent and volatilize after continue again to stir and evacuation 3 hours, product is fast with deionized water wash and be settled to 50mL, calculate the content of this solution Chinese medicine, filter residue and drying, the CNT-COOH that namely is able to poloxamer and PEG4000 mixture and is displacement object carries the verapamil hydrochloride delivery system.
Claims (5)
1. preparation method that the CNT-COOH take poloxamer F68 as displacement object carries the verapamil hydrochloride delivery system, its concrete steps are:
(1) get multi-walled carbon nano-tubes (MWCNT) 100mg, add 40mL H
2SO
4/ HNO
3Mixed liquor, wherein H
2SO
4With HNO
3Volume ratio be ultrasonic 24 hours of 3/1,30～40 ℃ of water-baths, with the dilution of 120mL deionized water, hold over night, sucking filtration, filtering residue with deionized water dialyse be neutrality to liquid after, water bath method is collected black powder, namely gets carboxylic carbon nano-tube (CNT-COOH);
(2) precision takes CNT-COOH 99.3mg and puts in reaction bulb, and evacuation is 1 hour while stirring; To add verapamil hydrochloride 99.6mg after poloxamer F68 0.4g melting, add a small amount of deionized water and make into the solution shape, get A liquid, A liquid is added in the CNT-COOH reaction bulb that evacuation has been processed, continue keep vacuum and stirred 2 hours, then after being heated to solvent under the vacuum stirring state and volatilizing, product is fast with washing with alcohol and be settled to 50mL, calculate the content of this solution Chinese medicine, filter residue and drying, the CNT-COOH that namely is able to poloxamer F68 and is displacement object carries verapamil hydrochloride delivery system 242.1mg.
2. preparation method that the CNT-COOH take PEG4000 as displacement object carries the verapamil hydrochloride delivery system, its concrete steps are:
(1) get multi-walled carbon nano-tubes (MWCNT) 100mg, add 40mL H
2SO
4/ HNO
3Mixed liquor, wherein H
2SO
4With HNO
3Volume ratio be ultrasonic 24 hours of 3/1,30～40 ℃ of water-baths, with the dilution of 120mL deionized water, hold over night, sucking filtration, filtering residue with deionized water dialyse be neutrality to liquid after, water bath method is collected black powder, namely gets carboxylic carbon nano-tube (CNT-COOH);
(2) precision takes CNT-COOH 100mg and puts in reaction bulb, and evacuation is 1 hour while stirring; To add verapamil hydrochloride 100mg after PEG4000 0.4g melting, add a small amount of deionized water and make into the solution shape, get A liquid, A liquid is added in the CNT-COOH reaction bulb that evacuation has been processed, continue keep vacuum and stirred 2 hours, then after being heated to solvent under the vacuum stirring state and volatilizing, product is fast with deionized water wash and be settled to 50mL, calculate the content of this solution Chinese medicine, filter residue and drying, the CNT-COOH that namely is able to PEG4000 and is displacement object carries verapamil hydrochloride delivery system 236.6mg.
3. preparation method that the CNT-COOH take lactose as displacement object carries the verapamil hydrochloride delivery system, its concrete steps are:
(1) get multi-walled carbon nano-tubes (MWCNT) 100mg, add 40mL H
2SO
4/ HNO
3Mixed liquor, wherein H
2SO
4With HNO
3Volume ratio be ultrasonic 24 hours of 3/1,30～40 ℃ of water-baths, with the dilution of 120mL deionized water, hold over night, sucking filtration, filtering residue with deionized water dialyse be neutrality to liquid after, water bath method is collected black powder, namely gets carboxylic carbon nano-tube (CNT-COOH);
(2) precision takes CNT-COOH100.2mg and puts in reaction bulb, and evacuation is 1 hour while stirring; The 5g lactose is mixed with saturated solution, add verapamil hydrochloride 99.9mg, add a small amount of deionized water and make into the solution shape, get A liquid, A liquid is added in the CNT-COOH reaction bulb that evacuation has been processed, continue keep vacuum and stirred 2 hours, then after being heated to solvent under the vacuum stirring state and volatilizing, product is fast with deionized water wash and be settled to 50mL, calculate the content of this solution Chinese medicine, filter residue and drying, the CNT-COOH that namely is able to lactose and is displacement object carries verapamil hydrochloride delivery system 1.1476g.
4. preparation method that the CNT-COOH take alkyl polyglucoside as displacement object carries the verapamil hydrochloride delivery system, its concrete steps are:
(1) get multi-walled carbon nano-tubes (MWCNT) 100mg, add 40mL H
2SO
4/ HNO
3Mixed liquor, wherein H
2SO
4With HNO
3Volume ratio be ultrasonic 24 hours of 3/1,30～40 ℃ of water-baths, with the dilution of 120mL deionized water, hold over night, sucking filtration, filtering residue with deionized water dialyse be neutrality to liquid after, water bath method is collected black powder, namely gets carboxylic carbon nano-tube (CNT-COOH);
(2) precision takes CNT-COOH 100mg and puts in reaction bulb, and evacuation is 1 hour while stirring; With alkyl polyglucoside 0.4g and verapamil hydrochloride 100mg, add a small amount of deionized water and make into the solution shape, get A liquid, A liquid is added in the CNT-COOH reaction bulb that evacuation processes, continues to keep vacuum also to stir 2 hours, then after being heated to solvent under the vacuum stirring state and volatilizing, product is fast with deionized water wash and be settled to 50mL, calculate the content of this solution Chinese medicine, filter residue and drying, the CNT-COOH that namely is able to alkyl polyglucoside and is displacement object carries the verapamil hydrochloride delivery system.
5. one kind carries the preparation method of verapamil hydrochloride delivery system take poloxamer and PEG4000 mixture as the CNT-COOH of displacement object, and its concrete steps are:
(1) get multi-walled carbon nano-tubes (MWCNT) 100mg, add 40mL H
2SO
4/ HNO
3Mixed liquor, wherein H
2SO
4With HNO
3Volume ratio be ultrasonic 24 hours of 3/1,30～40 ℃ of water-baths, with the dilution of 120mL deionized water, hold over night, sucking filtration, filtering residue with deionized water dialyse be neutrality to liquid after, water bath method is collected black powder, namely gets carboxylic carbon nano-tube (CNT-COOH);
(2) precision takes CNT-COOH 100mg and puts in reaction bulb, and evacuation is 1 hour while stirring; Poloxamer and PEG4000 mixture 0.4g and verapamil hydrochloride 100mg with the constant weight ratio, heat and add a small amount of deionized water and make into the solution shape, get A liquid, A liquid is added in the CNT-COOH reaction bulb that evacuation has been processed, continue again stirring and evacuation 3 hours after continuing heating, evacuation and be stirred to solvent to volatilize, product is fast with deionized water wash and be settled to 50mL, calculate the content of this solution Chinese medicine, filter residue and drying, the CNT-COOH that namely is able to poloxamer and PEG4000 mixture and is displacement object carries the verapamil hydrochloride delivery system.
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| CN101157437A (en) * | 2007-10-23 | 2008-04-09 | 浙江大学 | Method for preparing carbon nano-tube/CdS nano flower composite material |
| CN101177262A (en) * | 2007-11-08 | 2008-05-14 | 浙江大学 | Method for preparing water-soluble and high-biocompatibility carbon nano tube |
| CN102205238A (en) * | 2011-04-11 | 2011-10-05 | 东华大学 | Method for preparing MWCNTs/ZnO (multi-wall carbon nano tubes/zinc oxide) nanometer composite material |
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| CN101177262A (en) * | 2007-11-08 | 2008-05-14 | 浙江大学 | Method for preparing water-soluble and high-biocompatibility carbon nano tube |
| CN102205238A (en) * | 2011-04-11 | 2011-10-05 | 东华大学 | Method for preparing MWCNTs/ZnO (multi-wall carbon nano tubes/zinc oxide) nanometer composite material |
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