CN101590242A - The preparation method of chitosan or sodium alginate-modified carbon nanotube-targeted slow release carrier - Google Patents
The preparation method of chitosan or sodium alginate-modified carbon nanotube-targeted slow release carrier Download PDFInfo
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- CN101590242A CN101590242A CNA2009100543168A CN200910054316A CN101590242A CN 101590242 A CN101590242 A CN 101590242A CN A2009100543168 A CNA2009100543168 A CN A2009100543168A CN 200910054316 A CN200910054316 A CN 200910054316A CN 101590242 A CN101590242 A CN 101590242A
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Abstract
A kind of chitosan of technical field of nano material or the preparation method of sodium alginate-modified carbon nanotube-targeted slow release carrier comprise: the preparation shortening carbon nano-tube; The preparation modified carbon nano-tube; Preparation modified carbon nanotube-targeted slow release carrier and adding anthracycline anticancer drug aqueous solution, after supersound process and stir process, and through sucking filtration washing, vacuum drying under the room temperature obtains loading chitosan or sodium alginate-modified carbon nanotube-targeted slow release carrier behind the medicine.The carrying drug ratio of the present invention through calculating amycin can reach 156 ± 5%.
Description
Technical field
What the present invention relates to is a kind of preparation method of Nano medication technical field, specifically is the preparation method of a kind of chitosan or sodium alginate-modified carbon nanotube-targeted slow release carrier.
Background technology
CNT (Carbon Nanotube, be called for short CNT) be found in recent years a kind of novel carbon structure (S.Tijima, Nature 1991,354,56), be the seamless hollow carbon pipe that is curled and formed by the Graphene lamella that carbon atom forms, two ends respectively have the fullerene molecule end-blocking half, are a kind of One-dimensional Quantum materials with height delocalization pi-electron conjugated system.CNT be divided into SWCN (Single-wall Nanotube, SWCNT) and multi-walled carbon nano-tubes (Multi-wall Nanotube, MWCNT).Its preparation method mainly contains catalyse pyrolysis, arc discharge, template, chemical vapour deposition technique etc.Since CNT comes out,, become the focus of physics, chemistry, investigation of materials rapidly with its unique electronics and mechanical property and accurate one dimension tracheary element structure and potential huge applications value.
Cancer is the big persistent ailment that modern society threatens human health, and present Therapeutic Method mainly contains operation, radiation and chemotherapy, but which kind of method all can not reach the effect of radical cure fully.Targeted drug is considered as improving patients ' life quality future, realizes the handle sharp weapon that the band tumor is survived by people.The Multifucntional target carrier system of developing anti-tumor medicaments becomes the problem of assaulting fortified position of present global clinical tumor research.In recent years, the good film of striding that it is found that CNT has that the conventional medicine carrier do not possess, this makes researcher that sight is turned to and makes up and develop carbon nanotube-based anticancer targeting medicine carrier system.But because the CNT tube wall is smooth and highly polarizable, easy reunion bunchy under strong Van der Waals force effect, water-soluble hardly and various organic solvents are difficult to disperse, and therefore need carry out suitable modification to improve its water solublity to CNT.On the other hand, on CNT, realize function aspect targeting and the medicine carrying two, also need CNT is carried out functional modification.
Find through literature search prior art, Hanene Ali-Boucetta etc. are at " Chem.Commun. " (" chemical communication ") (2008,4,459) article of delivering on " Multiwalled carbonnanotube-doxorubicin supramolecular complexes for cancer therapeutics " has used polyoxypropylene block copolymers Pluronic F127 that multi-walled carbon nano-tubes is modified to improve its water solublity, in non-covalent mode amycin is adsorbed on the multi-walled carbon nano-tubes subsequently, the carbon pipe amycin complex that obtains has the bigger toxicity of purer amycin, does not have targeting but weak point is the carbon nanotube carrier of preparing.Chitosan (Chitosan, CHI) and sodium alginate (Alginate sodium ALG) is two kinds of polysaccharide that occurring in nature extensively exists, because its outstanding biocompatibility, is widely used in the research of biomedicine field recently.Utilizing these two kinds of polysaccharide that CNT is carried out non-covalent physics coats, can improve the dispersibility of CNT in water on the one hand, the amido functional group on chitosan surface can make us its further modification be realized the combination of targeting and medicine carrying function on the other hand.
Summary of the invention
The present invention is directed to the prior art above shortcomings, the preparation method of a kind of chitosan or sodium alginate-modified carbon nanotube-targeted slow release carrier is provided, promptly with chitosan and sodium alginate CNT being carried out non-covalent physics coats, and the folic acid that will have the targeting sexual function is connected to the polysaccharide surface, and the CNT pharmaceutical carrier that obtains has the function of targeting and slow release concurrently.
The present invention is achieved by the following technical solutions, the present invention includes following steps:
Step (a): the oxidisability mixed acid of 1 weight portion carbon nanometer tube material and 1～100 weight portion is mixed,, successively by sucking filtration after supersound process and the stir process, be 7 with deionized water cyclic washing to pH value then, obtain shortening carbon nano-tube behind the vacuum drying;
Described carbon nanometer tube material is meant single wall or the multi-walled carbon nano-tubes for preparing by catalyse pyrolysis, arc discharge, template or chemical vapour deposition technique method;
Described oxidisability mixed acid is meant: the nitric acid of 1～5mol/L, 0.1～100% weight acid concentration sulphuric acid, 1/100～100/1 mol ratio nitric acid and vitriolic mixed solution, 1/100～100/1 mol ratio potassium permanganate and sulfuric acid mixed solution or 1/100～100/1 mol ratio H
2O
2A kind of with in the sulfuric acid mixed solution;
Described supersound process is meant the ultrasonic Treatment 1～100min that adopts 20kHz～100kHz frequency;
Described stir process is meant stirring reaction 1～50h under 0～20 ℃ environment;
Described sucking filtration is meant with ф 0.22 μ m politef microporous filter membrane and carries out sucking filtration.
Step (b): the shortening carbon nano-tube aqueous solution of gained is passed through to add sodium alginate or chitosan aqueous solution after the supersound process, and then carry out carrying out sucking filtration and washing final vacuum drying successively after supersound process and the stir process, obtain modified carbon nano-tube;
The concentration of described shortening carbon nano-tube aqueous solution is 1～100mg/mL;
The concentration of described sodium alginate or chitosan solution is 1～10mg/mL, and the volume ratio of this sodium alginate or chitosan aqueous solution and shortening carbon nano-tube aqueous solution is 1: 1～1: 10;
Step (c): modified carbon nano-tube is configured to the CNT phosphate buffer adds folic acid and polypeptide condensing agent successively through after the supersound process, and then pass through by supersound process and stir process, and through the sucking filtration washing, vacuum drying under the room temperature obtains modified carbon nanotube-targeted slow release carrier;
The concentration of described CNT phosphate buffer is 1～50mg/mL;
Described folic acid consumption is 1～50mg, and polypeptide condensing agent consumption is 1～50mg;
Step (d): modified carbon nanotube-targeted slow release carrier is configured to modified carbon nanotube-targeted slow release carrier phosphoric acid buffer liquor and after supersound process, adds the anthracycline anticancer drug aqueous solution, after supersound process and stir process, and wash through sucking filtration, vacuum drying under the room temperature obtains loading chitosan or sodium alginate-modified carbon nanotube-targeted slow release carrier behind the medicine.
The concentration of described modified carbon nanotube-targeted slow release carrier phosphoric acid buffer liquor is 1～20mg/mL;
Described anthracycline anticancer drug is meant: amycin (Doxorubicin, DOX) or epirubicin (Epirubicin, EPB).
The concentration of described anthracycline anticancer drug phosphoric acid buffer liquor is 1～100mg/mL, and the volume ratio of this anthracycline anticancer drug aqueous solution and modified carbon nanotube-targeted slow release carrier phosphoric acid buffer liquor is 1: 1～1: 10.
Preparation method provided by the invention is simple, and controllability is strong.Gained carbon nanotube carrier good water solubility, can realize slow release effect under the acid pH of anthracycline anticancer drugs such as amycin, and has a target function to cancerous cell, to the toxic action of cancerous cell much larger than pure effect of drugs, to the important directive significance that is being built with of the nano target drug-loading system that is used for treatment of cancer.
Description of drawings
Fig. 1 a is the transmission electron microscope photo of shortening carbon nano-tube;
Fig. 1 b is the transmission electron microscope photo after folic acid targeted chitosan or sodium alginate-modified carbon nanotube carrier load amycin;
Fig. 2 is for loading folic acid targeted chitosan behind the amycin or the sodium alginate-modified medicament slow release schematic graph of CNT in different pH environment;
Fig. 3 is human uterine cancer cell process folic acid targeted chitosan or sodium alginate-modified carbon nanotube carrier (FA-CHI/ALG-SWCNTs), the survival rate sketch map behind the folic acid targeted chitosan of medicine carrying or sodium alginate-modified carbon nanotube (DOX-FA-CHI/ALG-SWCNTs) and pure amycin (DOX) the processing 1h behind continuation cultivation 24h, 48h and the 72h;
Fig. 4 enters the mechanism of action sketch map of cancerous cell for folic acid targeted chitosan or sodium alginate-modified carbon nanotube carrier.
The specific embodiment
Below embodiments of the invention are elaborated, present embodiment is being to implement under the prerequisite with the technical solution of the present invention, provided detailed embodiment and concrete operating process, but protection scope of the present invention is not limited to following embodiment.
Embodiment 1, the SWCN (SWCNTs) for preparing with the chemical vapour deposition technique method are initial raw material, after the acidified truncate, coat chitosan or sodium alginate and folic acid functionalization to the SWCN surface by non-covalent physics, and employing amycin (DOX) is a model drug, obtain the chitosan or the sodium alginate-modified SWCN adriablastina target pharmaceutical carrier of folic acid targeting, concrete steps are as follows:
Step (a): the 98%H that in the 300mL volume ratio is 3: 1
2SO
4And 65%HNO
3Add SWCN raw material 500mg in the nitration mixture, ultrasonic 24h under 0 ℃ of ice-water bath, with the politef microporous filter membrane sucking filtration in Φ 0.22 μ m aperture, and with a large amount of deionized water cyclic washings repeatedly to neutral, obtain the SWCN of truncate behind 50 ℃ of vacuum drying 24h;
Step (b): in single neck round-bottomed flask of magnetic agitation rotor is housed, SWCN aqueous solution after the truncate of adding 40mL 2mg/mL step (a) gained, behind 40kHz ultrasonic Treatment 20min, the aqueous solution that adds 80mL 2mg/mL sodium alginate, behind 40kHz ultrasonic Treatment 1h, stir 12h under the room temperature, with ф 0.22 μ m politef microporous filter membrane sucking filtration, with a large amount of deionized water cyclic washings, drying obtains sodium alginate-modified SWCN under the room temperature; Subsequently in single neck round-bottomed flask of magnetic agitation rotor is housed, add the sodium alginate-modified SWCN aqueous solution of 30mL 2mg/mL gained, behind 40kHz ultrasonic Treatment 20min, acetic acid (0.05M) aqueous solution that adds 60mL 2mg/mL chitosan, behind 40kHz ultrasonic Treatment 1h, stir 12h under the room temperature, also use a large amount of deionized water wash, obtain chitosan or sodium alginate-modified SWCN with ф 0.22 μ m politef microporous filter membrane sucking filtration;
Step (c): behind the SWCN phosphoric acid buffer liquor usefulness 40kHz ultrasonic Treatment 20min with 20mL 2mg/mL step (b) gained chitosan or sodium alginate modification, add the folic acid of 60mg and the polypeptide condensing agent (EDC) of 50mg, with 40kHz ultrasonic Treatment 20min, stir 12h under the room temperature, wash through sucking filtration, vacuum drying under the room temperature obtains the chitosan of folic acid targeting or sodium alginate-modified SWCN cancer therapy drug targeted slow release carrier;
Step (d): the phosphoric acid buffer liquor of the SWCN that the chitosan of 15mL 1mg/mL step (c) gained folic acid targeting or sodium alginate are modified with 40kHz ultrasonic Treatment 10min after, the phosphoric acid buffer liquor that adds the 15mL3mg/mL amycin, with 40kHz ultrasonic Treatment 20min, lucifuge stirs 12h under the room temperature, wash through sucking filtration, vacuum drying under the room temperature obtains loading the chitosan behind the amycin or the modification SWCN cancer therapy drug targeted slow release carrier of sodium alginate.
As shown in Figure 1, be the construction features of SWCN and chitosan or sodium alginate-modified SWCN targeting vector.As Fig. 1 a SWCN structural pipe wall clearly as can be seen, shown in Fig. 1 b, because the covering and the shielding of amycin, chitosan or sodium alginate adsorption layer can not be known the tube wall of seeing the carbon pipe.Simultaneously can reach (156 ± 5%) to the carrying drug ratio of amycin through measuring and calculating chitosan or sodium alginate-modified SWCN targeting vector.
As shown in Figure 2, be the drug release characteristics under different pH value after chitosan or the sodium alginate SWCN targeting vector load cancer therapy drug.Amycin presents the characteristics that constantly slowly discharge in time to amycin after 5.5 when pH reduces to combining of carbon pipe is comparatively stable in the neutral environment of pH7.4.
As shown in Figure 3, for chitosan or sodium alginate-modified SWCN folic acid anti-cancer medicament carrier (FA-CHI/ALG-SWCNTs) itself do not have obvious cytotoxicity, the growth that (DOX-FA-CHI/ALG-SWCNTs) can more significant inhibition human uterus cancerous cell than pure amycin after its carrier band cancer therapy drug.
As shown in Figure 4, enter the mechanism of action sketch map of cancerous cell for chitosan or sodium alginate-modified SWCN folic acid anti-cancer medicament carrier.
Embodiment 2, the SWCN (SWCNTs) for preparing with the chemical vapour deposition technique method are initial raw material, after the acidified truncate, coat chitosan or sodium alginate and folic acid functionalization to the SWCN surface by non-covalent physics, and employing epirubicin (EPB) is a model drug, obtain the chitosan or the sodium alginate-modified SWCN adriablastina target pharmaceutical carrier of folic acid targeting, concrete steps are as follows:
Step (a): the 98%H that in the 300mL volume ratio is 3: 1
2SO
4And 65%HNO
3Add SWCN raw material 500mg in the nitration mixture, ultrasonic 24h under 0 ℃ of ice-water bath, with the politef microporous filter membrane sucking filtration in Φ 0.22 μ m aperture, and with a large amount of deionized water cyclic washings repeatedly to neutral, obtain the SWCN of truncate behind 50 ℃ of vacuum drying 24h;
Step (b): in single neck round-bottomed flask of magnetic agitation rotor is housed, SWCN aqueous solution after the truncate of adding 40mL 2mg/mL step (a) gained, behind 40kHz ultrasonic Treatment 20min, the aqueous solution that adds 80mL 2mg/mL sodium alginate, behind 40kHz ultrasonic Treatment 1h, stir 12h under the room temperature, with ф 0.22 μ m politef microporous filter membrane sucking filtration, with a large amount of deionized water cyclic washings, drying obtains sodium alginate-modified SWCN under the room temperature; Subsequently in single neck round-bottomed flask of magnetic agitation rotor is housed, add the sodium alginate-modified SWCN aqueous solution of 30mL 2mg/mL gained, behind 40kHz ultrasonic Treatment 20min, acetic acid (0.05M) aqueous solution that adds 60mL 2mg/mL chitosan, behind 40kHz ultrasonic Treatment 1h, stir 12h under the room temperature, also use a large amount of deionized water wash, obtain chitosan or sodium alginate-modified SWCN with ф 0.22 μ m politef microporous filter membrane sucking filtration;
Step (c): behind the SWCN phosphoric acid buffer liquor usefulness 40kHz ultrasonic Treatment 20min with 20mL 2mg/mL step (b) gained chitosan or sodium alginate modification, add the folic acid of 60mg and the polypeptide condensing agent (EDC) of 50mg, with 40kHz ultrasonic Treatment 20min, stir 12h under the room temperature, wash through sucking filtration, vacuum drying under the room temperature obtains the chitosan of folic acid targeting or sodium alginate-modified SWCN cancer therapy drug targeted slow release carrier;
Step (d): the phosphoric acid buffer liquor of the SWCN that the chitosan of 15mL 1mg/mL step (c) gained folic acid targeting or sodium alginate are modified with 40kHz ultrasonic Treatment 10min after, the phosphoric acid buffer liquor that adds the 15mL3mg/mL epirubicin, with 40kHz ultrasonic Treatment 20min, lucifuge stirs 12h under the room temperature, wash through sucking filtration, vacuum drying under the room temperature obtains the chitosan behind the load table amycin or the modification SWCN cancer therapy drug targeted slow release carrier of sodium alginate.
The modification SWCN carrier of chitosan behind the load table amycin that embodiment 2 obtains or sodium alginate has better water solubility, and carrying drug ratio also can reach 144 ± 6%.
Embodiment 3, the multi-walled carbon nano-tubes (MWCNTs) for preparing with the chemical vapour deposition technique method are initial raw material, after the acidified truncate, coat chitosan or sodium alginate and folic acid functionalization to the multi-wall carbon nano-tube tube-surface by non-covalent physics, and employing amycin (DOX) is a model drug, obtain the chitosan or the sodium alginate-modified multi-walled carbon nano-tubes adriablastina target pharmaceutical carrier of folic acid targeting, concrete steps are as follows:
Step (a): the 98%H that in the 300mL volume ratio is 3: 1
2SO
4And 65%HNO
3Add multi-walled carbon nano-tubes raw material 500mg in the nitration mixture, ultrasonic 24h under 0 ℃ of ice-water bath, with the politef microporous filter membrane sucking filtration in Φ 0.22 μ m aperture, and with a large amount of deionized water cyclic washings repeatedly to neutral, obtain the multi-walled carbon nano-tubes of truncate behind 50 ℃ of vacuum drying 24h;
Step (b): in single neck round-bottomed flask of magnetic agitation rotor is housed, multi-walled carbon nano-tubes aqueous solution after the truncate of adding 40mL 2mg/mL step (a) gained, behind 40kHz ultrasonic Treatment 20min, the aqueous solution that adds 80mL 2mg/mL sodium alginate, behind 40kHz ultrasonic Treatment 1h, stir 12h under the room temperature, with ф 0.22 μ m politef microporous filter membrane sucking filtration, with a large amount of deionized water cyclic washings, drying obtains sodium alginate-modified multi-walled carbon nano-tubes under the room temperature; Subsequently in single neck round-bottomed flask of magnetic agitation rotor is housed, add the sodium alginate-modified multi-walled carbon nano-tubes aqueous solution of 30mL 2mg/mL gained, behind 40kHz ultrasonic Treatment 20min, acetic acid (0.05M) aqueous solution that adds 60mL 2mg/mL chitosan, behind 40kHz ultrasonic Treatment 1h, stir 12h under the room temperature, also use a large amount of deionized water wash, obtain chitosan or sodium alginate-modified multi-walled carbon nano-tubes with ф 0.22 μ m politef microporous filter membrane sucking filtration;
Step (c): behind the multi-walled carbon nano-tubes phosphoric acid buffer liquor usefulness 40kHz ultrasonic Treatment 20min with 20mL 2mg/mL step (b) gained chitosan or sodium alginate modification, add the folic acid of 60mg and the polypeptide condensing agent (EDC) of 50mg, with 40kHz ultrasonic Treatment 20min, stir 12h under the room temperature, wash through sucking filtration, vacuum drying under the room temperature obtains the chitosan of folic acid targeting or sodium alginate-modified multi-walled carbon nano-tubes cancer therapy drug targeted slow release carrier;
Step (d): the phosphoric acid buffer liquor of the multi-walled carbon nano-tubes that the chitosan of 15mL 1mg/mL step (c) gained folic acid targeting or sodium alginate are modified with 40kHz ultrasonic Treatment 10min after, the phosphoric acid buffer liquor that adds the 15mL3mg/mL epirubicin, with 40kHz ultrasonic Treatment 20min, lucifuge stirs 12h under the room temperature, wash through sucking filtration, vacuum drying under the room temperature obtains the chitosan behind the load table amycin or the modification multi-walled carbon nano-tubes cancer therapy drug targeted slow release carrier of sodium alginate.
The modification multi-walled carbon nano-tubes cancer therapy drug targeted slow release carrier of chitosan behind the load table amycin that embodiment 3 obtains or sodium alginate has better water solubility, and carrying drug ratio is big slightly than the SWCN carrier, can reach 172 ± 5%.
Claims (10)
1, the preparation method of a kind of chitosan or sodium alginate-modified carbon nanotube-targeted slow release carrier is characterized in that, may further comprise the steps:
Step (a): the oxidisability mixed acid of 1 weight portion carbon nanometer tube material and 1～100 weight portion is mixed,, successively by sucking filtration after supersound process and the stir process, be 7 with deionized water cyclic washing to pH value then, obtain shortening carbon nano-tube behind the vacuum drying;
Step (b): the shortening carbon nano-tube aqueous solution of gained is passed through to add sodium alginate or chitosan aqueous solution after the supersound process, and then carry out carrying out sucking filtration and washing final vacuum drying successively after supersound process and the stir process, obtain modified carbon nano-tube;
Step (c): modified carbon nano-tube is configured to the CNT phosphate buffer adds folic acid and polypeptide condensing agent successively through after the supersound process, and then pass through by supersound process and stir process, and through the sucking filtration washing, vacuum drying under the room temperature obtains modified carbon nanotube-targeted slow release carrier;
Step (d): modified carbon nanotube-targeted slow release carrier is configured to modified carbon nanotube-targeted slow release carrier phosphoric acid buffer liquor and after supersound process, adds the anthracycline anticancer drug aqueous solution, after supersound process and stir process, and wash through sucking filtration, vacuum drying under the room temperature obtains loading chitosan or sodium alginate-modified carbon nanotube-targeted slow release carrier behind the medicine.
2, the preparation method of chitosan according to claim 1 or sodium alginate-modified carbon nanotube-targeted slow release carrier, it is characterized in that described carbon nanometer tube material is meant single wall or the multi-walled carbon nano-tubes for preparing by catalyse pyrolysis, arc discharge, template or chemical vapour deposition technique method.
3, the preparation method of chitosan according to claim 1 or sodium alginate-modified carbon nanotube-targeted slow release carrier, it is characterized in that described oxidisability mixed acid is meant: the nitric acid of 1～5mol/L, 0.1～100% weight acid concentration sulphuric acid, 1/100～100/1 mol ratio nitric acid and vitriolic mixed solution, 1/100～100/1 mol ratio potassium permanganate and sulfuric acid mixed solution or 1/100～100/1 mol ratio H
20
2A kind of with in the sulfuric acid mixed solution.
4, the preparation method of chitosan according to claim 1 or sodium alginate-modified carbon nanotube-targeted slow release carrier is characterized in that, described supersound process is meant the ultrasonic Treatment 1～100min that adopts 20kHz～100kHz frequency.
5, the preparation method of chitosan according to claim 1 or sodium alginate-modified carbon nanotube-targeted slow release carrier is characterized in that, described stir process is meant stirring reaction 1～50h under 0～20 ℃ environment.
6, the preparation method of chitosan according to claim 1 or sodium alginate-modified carbon nanotube-targeted slow release carrier is characterized in that, described sucking filtration is meant with φ 0.22 μ m politef microporous filter membrane and carries out sucking filtration.
7, the preparation method of chitosan according to claim 1 or sodium alginate-modified carbon nanotube-targeted slow release carrier is characterized in that, the concentration of described shortening carbon nano-tube aqueous solution is 1～100mg/mL.
8, the preparation method of chitosan according to claim 1 or sodium alginate-modified carbon nanotube-targeted slow release carrier, it is characterized in that, the concentration of described sodium alginate or chitosan solution is 1～10mg/mL, and the volume ratio of this sodium alginate or chitosan aqueous solution and shortening carbon nano-tube aqueous solution is 1: 1～1: 10.
9, the preparation method of chitosan according to claim 1 or sodium alginate-modified carbon nanotube-targeted slow release carrier is characterized in that, the concentration of described CNT phosphate buffer is 1～50mg/mL.
10, the preparation method of chitosan according to claim 1 or sodium alginate-modified carbon nanotube-targeted slow release carrier is characterized in that, the concentration of described modified carbon nanotube-targeted slow release carrier phosphoric acid buffer liquor is 1～20mg/mL.
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