CN102274192B - Carboxymethyl chitosan medicament-carrying microspheres and preparation method thereof - Google Patents
Carboxymethyl chitosan medicament-carrying microspheres and preparation method thereof Download PDFInfo
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Abstract
The invention discloses carboxymethyl chitosan nano medicament-carrying microspheres and a preparation method thereof. The preparation method comprises the following steps of: preparing aqueous solution of carboxymethyl chitosan, dissolving a medicament into the carboxymethyl chitosan solution, stirring the solution uniformly, adding calcium chloride solution, and performing one-time ion cross-linking pre-coating; adding surfactant into an oily component, stirring the surfactant and the oily component to obtain an oil phase mixture, adding the pre-coated mixed solution into the oil phase mixture, quickly stirring the solution to form a water-in-oil mixture, adding glutaraldehyde, performing secondary curing cross-linking reaction to obtain medicament-coated carboxymethyl chitosan microspheres, performing centrifugal separation on the two-phase mixture, cleaning the lower layer by using petroleum ether or ethanol solvent, washing with distilled water, drying, and thus obtaining the carboxymethyl chitosan nano medicament-carrying microspheres. Because the carboxymethyl chitosan with biocompatibility, safety, non-toxicity and capability of being safely metabolized in vivo is used as a coating material, the carboxymethyl chitosan nano medicament-carrying microspheres have the characteristics of small medicament-carrying granule, high medicament-carrying amount and coating rate, good sustained-release performance and capability of fully exerting the effect of the medicament.
Description
Technical field
The present invention is relevant with pharmaceutical carrier and preparation method thereof, and is more detailed, is a kind of carboxymethyl chitosan nano drug-carrying microsphere and preparation method thereof.
Background technology
Chitosan has been widely used as pharmaceutical carrier and medical auxiliary material now, mainly is that good biocompatibility has no side effect because it has the adhesiveness height.But chitosan only can be dissolved under the sour environment, thereby is not suitable for coating medicine under neutrality or alkali condition.Carboxymethyl chitosan is a kind of water-solubility chitosan derivative, comes into one's own gradually at medical domain because it also has excellent biological compatibility, avirulence and biodegradable.Adopt carboxymethyl chitosan as carrier material among the present invention, can in wideer pH scope, coat medicine, be particularly useful for biologically active, the medicine comparatively responsive to pH.
Medicine carrying microballoons is the spherical polymer microsphere with macromolecular material or the preparation of other monomers.Medicine carrying microballoons is the circulating half-life of prolong drug in human body effectively, plays target administration, the function of medicament slow release.Can reduce medicine frequency, keep stable, lasting effect.
In the pharmaceutical carrier document of existing open report, publication number is that CN1846788A discloses " a kind of preparation method of nanometer carboxymethyl chitosan particle ", and this method is utilized sodium tripolyphosphate or CaCl
2Directly prepare nanoparticle as cross-linking agent in solution, make the preparation method of nanometer carboxymethyl chitosan particle carry out under neutrallty condition, mild condition is applicable to the carrier of responsive macromole class; But simple ionic cross-linking covered effect instability is restricted the drug loading of carboxymethyl chitosan microsphere.
That publication number is that CN101215384A discloses is a kind of " once or the method for secondary cross-linking prepare chitosan micro-sphere crosslinked resin " carries out crosslinkedly with aldehydes, and be used for the parcel solid absorbent.This method mainly adopts the method that repeats to add cross-linking agent to carry out secondary cross-linking, and the revenge fastness of complex microsphere is improved.But cross-linking reaction at first is in acidity, remains on then under the alkaline environment and carries out.When if required year medicine is responsive to pH, what then can cause medicine is to lose efficacy.
Publication number is that CN1698900A discloses a kind of size homogeneous, the embedding rate height, and chitosan drug-loading microsphere that the pharmaceutically active conservation rate is high and preparation method thereof has adopted the method for the crosslinked and chemical crosslinking secondary cross-linking of ionic gel, has guaranteed the medicine embedding rate.By microporous membrane water is pressed in the oil phase, and secondary cross-linking.Because chitosan only is dissolved in the acid solution, for acid nonfast medicine, this method can be destroyed the effect of medicine, and, be by microporous membrane, complicated operation.
Summary of the invention
The present invention is based on the chitosan good biocompatibility, the characteristics that have no side effect, be applied in the preparation of drug carriers, but chitosan only is dissolved in the mineral acid or organic acid soln of low concentration, make its part can't stable existence in this environment to the unsettled medicine of acid, thereby can't wrap the medicine carrying thing, this deficiency at existing Preparation of Chitosan pharmaceutical carrier, the present invention uses water-soluble carboxymethyl Preparation of Chitosan pharmaceutical carrier, make macromole class medicine acid and alkali destroy, realize a kind of carboxymethyl chitosan medicament-carrying nano-microsphere that the present invention will provide and preparation method thereof with this.
To achieve these goals, composition and the content thereof of a kind of carboxymethyl chitosan medicament-carrying nano-microsphere of taking of the present invention are as follows by weight:
10～50 parts of carboxymethyl chitosans;
1～20 part of medicine;
1～10 part in calcium chloride;
10～20 parts of glutaraldehydes.
In the technical scheme of above-mentioned medicament-carrying nano-microsphere, described medicine is biologically active, to the medical of pH sensitivity; Described nanometer is less than one micron unit level.
A kind of preparation method for the carboxymethyl chitosan nano drug-carrying microsphere that the present invention takes, this method comprises the following steps:
(1) the carboxymethyl chitosan sugar aqueous solution of preparation 0.001～0.01kg/L;
(2) medicine is joined in the carboxymethyl chitosan sugar juice, stir;
(3) slowly add 0.001～0.01kg/L calcium chloride solution, in 2000～5000 rev/mins of stirrings of rotating speed, carry out first time ionomer and coat processing in advance, crosslinking time is 0.5～2h;
(4) with the volume ratio of surfactant with 1:80～180, join with the immiscible oiliness composition of water in, stir as oil mixture;
(5) the pre-mixed solution handled of coating of step (2) is joined in the oil mixture that step (4) prepares with 1:40～150, adopt boxshear apparatus to stir with 8000～20000 rev/mins of THE ADIABATIC SHEAR IN, form the water-in-oil type mixture, after the shear agitation 10～30 minutes, adding concentration is that 5～20% glutaraldehydes carry out the curing cross-linking reaction second time, obtains being coated with the carboxymethyl chitosan microsphere product of medicine;
(6) with mixture centrifugalize under 10000～20000 rev/mins centrifuge speed, lower sediment is cleaned 3～5 times with petroleum ether or alcohol solvent respectively, distilled water wash 2～4 times, vacuum drying in 20～40 ℃ makes a kind of carboxymethyl chitosan nano drug-carrying microsphere.
In above-mentioned technical scheme for carboxymethyl chitosan nano drug-carrying microsphere preparation method, described surfactant is one or several mixing in Span-80, Span-85, twen-60, twen-80 and the sorbate; Described oil mixture is one or more mixture in liquid paraffin, soybean oil, Oleum Arachidis hypogaeae semen, olive oil and the sunflower oil.
A kind of carboxymethyl chitosan medicament-carrying nano-microsphere of the present invention, compare with existing pharmaceutical carrier, according to its attribute that has, has good bio-compatible characteristic, safety non-toxic in vivo not only can safe metabolism, and can coat medicine under wideer pH scope, can not cause drug failure, be to coat best preferred material as medicine carrying at present.
In the technical process of preparation, the inventive method can coat its medicine under benign environment, and preparation technology is simple, cycle is short, can fully guarantee the realization of contained medication amount, especially the activity of sensitive kinds macromole active medicine is not destroyed, and it is little to have a particle diameter at the medicine carrying granule by secondary cross-linking preparation, the drug loading height, the clad ratio height, sustained release performance is good, has prolonged the medicine half-life in vivo, can give full play to the effect of medicine, energy needed is lower than institute's energy requirements such as solvent evaporated methods.Medicine comprises general small-molecule drug, and biologically active, to the polypeptide protein class medicine of pH sensitivity, and a kind of as in apigenin, Quercetin, L-tryptophan and the pGenesil-1 plasmid.
Description of drawings
Fig. 1 is carboxymethyl chitosan Nano microsphere SEM picture.
Fig. 2 is carboxymethyl chitosan nano drug-carrying thing L-tryptophan microsphere SEM picture.
Fig. 3 is the ultraviolet-visible spectrogram of carboxymethyl chitosan Nano microsphere and carboxymethyl chitosan nano drug-carrying thing L-tryptophan microsphere.
Among the figure: a curve is the ultraviolet-visible spectrogram of carboxymethyl chitosan Nano microsphere, and the b curve is the ultraviolet-visible spectrogram of carboxymethyl chitosan nano drug-carrying thing L-tryptophan microsphere.
The specific embodiment
Implement a kind of carboxymethyl chitosan medicament-carrying nano-microsphere that the present invention proposes, the technical scheme of taking is as matrix material with carboxymethyl chitosan, in solution, adopt ionomer, and then shear to form the little drop of Water-In-Oil with the shear agitation instrument, the method of carrying out chemical secondary cross-linking coats, and purpose is to improve the covered effect of medicine.
In the present invention, theoretically, described medicine refers to medical, namely referring to influence organism physiology, biochemistry and pathological process, chemical substance in order to prevention, diagnosis, treatment disease and family planning comprises general small-molecule drug, and biologically active, to the polypeptide protein class medicine of pH sensitivity, as medicals such as apigenin, Quercetin, L-tryptophan, pGenesil-1 plasmids; In experiment of the present invention, only apigenin, Quercetin, L-tryptophan and pGenesil-1 plasmid have been carried out coating experiment, by that analogy, the present invention can coat the medical that is similar to apigenin, Quercetin, L-tryptophan and pGenesil-1 plasmid, can obtain described effect too; Its described nanometer refers to the organizational level less than a micron.
In implementation process of the present invention, described surfactant is one or several mixing of adopting in Span-80, Span-85, twen-60, twen-80 and the sorbate; Described oil mixture is one or more mixture that adopt in liquid paraffin, soybean oil, Oleum Arachidis hypogaeae semen, olive oil and the sunflower oil.
Concrete embodiment further describes as follows:
Embodiment 1
At first, getting the composition of carboxymethyl chitosan medicament-carrying nano-microsphere and the weight portion of content thereof is 50 parts of carboxymethyl chitosans; 20 parts of L-tryptophans; 2 parts in calcium chloride; 15 parts of glutaraldehydes.The employing effects of ion is crosslinked, the method coating medicine of chemical crosslinking in the composite micro-emulsion liquid, and medicine can be water-soluble, also can be insoluble, this method not only is confined to the medicine of solubility.
Secondly, the 5g carboxymethyl chitosan is joined in the 100ml water, stir with 2000 rev/mins rotating speeds, be made into the carboxymethyl chitosan sugar juice of 5wt%.Add the 2gL-tryptophan, 3000 rev/mins were stirred 10 minutes.1% of adding 20mL calcium chloride solution under lasting the stirring.Getting 5mLSpan-80 joins in the 600mL liquid paraffin, carry out shear agitation with boxshear apparatus with 10000 rev/mins, get after the calcium chloride cross-linking reaction reactant liquor by volume the ratio of 1:60 join 600mL and added in the liquid paraffin of Span-80, shear agitation forms the water-in-oil type mixture.The glutaraldehyde solution 10mL of adding 15% carries out the second step curing cross-linking reaction.React after 15 minutes, stop to stir, reactant liquor is carried out centrifugalize with 15000 rev/mins.Take off layer precipitation, clean with petroleum ether, centrifugalize so repeats 3 times.With precipitate washed with de-ionized water 2 times.Make a kind of carboxymethyl chitosan nano drug-carrying microsphere.
In above-mentioned experimentation, under 10.0KV, amplify 3000 times by JSM-6700F type field emission scanning electron microscope (FESEM) and observe nanometer carboxymethyl chitosan microsphere and nanometer carboxymethyl chitosan medicine carrying thing L-tryptophan microsphere pattern down, do not add under the condition of L-tryptophan, can make nanometer carboxymethyl chitosan microsphere, its pattern as shown in Figure 1, microsphere diameter is about 30nm; Under the condition of adding medicine L-tryptophan, can make the microsphere of nanoscale carboxymethyl chitosan medicine carrying thing L-tryptophan, its pattern as shown in Figure 2, diameter is about 80nm.Two kinds of microspheres are compared, and the mean diameter of the microsphere of nanoscale carboxymethyl chitosan medicine carrying thing L-tryptophan is greater than nanometer carboxymethyl chitosan microsphere, and microsphere surface does not have significant difference.Use drug loading and the envelop rate of JH756MC ultraviolet-uisible spectrophotometer research medicine carrying chitosan microball, in the ultraviolet light range of 280-400nm, both are carried out ultraviolet spectral analysis, its result as shown in Figure 3, wherein nanoscale carboxymethyl chitosan microsphere does not have obvious absorption peaks in the 280-400nm scope; And absworption peak appears in nanoscale carboxymethyl chitosan medicine carrying thing L-tryptophan microsphere at the 298nm place, and this characteristic peak is the characteristic absorption peak of L-tryptophan.Hence one can see that, is loaded with medicine L-tryptophan in the microsphere.And go out to measure its ultraviolet absorptivity at the maximum absorption wavelength of L-tryptophan and 298nm, according to following formula:
Drug loading=(microspheres quality that the drug quality ÷ in the microsphere takes by weighing) * 100%
Entrapment efficiency=(theoretical content of the drug quality ÷ medicine in the microsphere) * 100%
It is 7.5% that calculating can get carrying drug ratio, and envelop rate is 15.0%.
Therefore, in the technical process of preparation, the inventive method can coat its medicine under benign environment, and preparation technology is simple, cycle is short, can fully guarantee the realization of contained medication amount, and especially the activity of sensitive kinds macromole active medicine is not destroyed, and it is little to have a particle diameter at the medicine carrying granule by secondary cross-linking preparation, the drug loading height, the clad ratio height, sustained release performance is good, prolong the medicine half-life in vivo, can give full play to the effect of medicine.
Embodiment 2
The 1g carboxymethyl chitosan is joined in the 100mL water, stir with 1000 rev/mins rotating speeds, be made into the carboxymethyl chitosan sugar juice of 1wt%.Add the 0.2g Quercetin, 2000 rev/mins were stirred 10 minutes.1% of adding 5mL calcium chloride solution under lasting the stirring.Getting 2mLSpan-85 joins in the 200mL liquid paraffin, carry out shear agitation with boxshear apparatus with 8000 rev/mins, get after the calcium chloride cross-linking reaction reactant liquor 10mL by volume the ratio of 1:20 join 200mL and added in the liquid paraffin of Span-85, shear agitation forms the water-in-oil type mixture.The glutaraldehyde solution 5mL of adding 10% carries out the second step curing cross-linking reaction.React after 10 minutes, stop to stir, reactant liquor is carried out centrifugalize with 10000 rev/mins.Take off layer precipitation, clean with petroleum ether, centrifugalize so repeats 3 times.With precipitate washed with de-ionized water 2 times.Obtain a kind of carboxymethyl chitosan nano drug-carrying microsphere.
The composition of the carboxymethyl chitosan medicament-carrying nano-microsphere that said method is prepared and the weight portion of content thereof are 50 parts of carboxymethyl chitosans; 10 parts of Quercetins; 3 parts in calcium chloride; 25 parts of glutaraldehydes.This method and spray drying method, utilize method such as microporous membrane to compare, do not need specific apparatus or device flow process, used instrument is common, simple to operate, on the basis that guarantees drug loading and microsphere diameter, simplified operation, reduce energy consumption, thereby reduced the cost of product.
Embodiment 3
The 10g carboxymethyl chitosan is joined in the 100mL water, stir with 3000 rev/mins rotating speeds, be made into the carboxymethyl chitosan sugar juice of 10wt%.Add the 3g apigenin, 5000 rev/mins were stirred 15 minutes.1% of adding 20mL calcium chloride solution under lasting the stirring.Getting 5mLtwen-80 joins in the 800mL Oleum Arachidis hypogaeae semen, carry out shear agitation with boxshear apparatus with 20000 rev/mins, get after the calcium chloride cross-linking reaction reactant liquor 10mL by volume the ratio of 1:80 join 800mL and added in the Oleum Arachidis hypogaeae semen of twen-80, shear agitation forms the water-in-oil type mixture.The glutaraldehyde solution 20mL of adding 20% carries out the second step curing cross-linking reaction.React after 30 minutes, stop to stir, reactant liquor is carried out centrifugalize with 20000 rev/mins.Take off layer precipitation, clean with petroleum ether, centrifugalize so repeats 3 times.With precipitate washed with de-ionized water 2 times.Obtain a kind of carboxymethyl chitosan nano drug-carrying microsphere.
The composition of the carboxymethyl chitosan medicament-carrying nano-microsphere that said method is prepared and the weight portion of content thereof are 50 parts of carboxymethyl chitosans; 15 parts of apigenins; 1 part in calcium chloride; 20 parts of glutaraldehydes.
Embodiment 4
The 4g carboxymethyl chitosan is joined in the 100mL water, stir with 1500 rev/mins rotating speeds, be made into the carboxymethyl chitosan sugar juice of 4wt%.Add the 1.5gpGenesil-1 plasmid, 1500 rev/mins were stirred 10 minutes.1% of adding 10mL calcium chloride solution under lasting the stirring.Getting 3mLtwen-60 joins in the 400mL soybean oil, carry out shear agitation with boxshear apparatus with 12000 rev/mins, get after the calcium chloride cross-linking reaction reactant liquor 10mL by volume the ratio of 1:40 join 400mL and added in the soybean oil of twen-60, shear agitation forms the water-in-oil type mixture.The glutaraldehyde solution 10mL of adding 10% carries out the second step curing cross-linking reaction.React after 20 minutes, stop to stir, reactant liquor is carried out centrifugalize with 18000 rev/mins.Take off layer precipitation, clean with petroleum ether, centrifugalize so repeats 3 times.With precipitate washed with de-ionized water 2 times.Obtain a kind of carboxymethyl chitosan nano drug-carrying microsphere.
The composition of the carboxymethyl chitosan medicament-carrying nano-microsphere that said method is prepared and the weight portion of content thereof are 50 parts of carboxymethyl chitosans; 18 parts of pGenesil-1 plasmids; 2 parts in calcium chloride; 13 parts of glutaraldehydes.
Claims (1)
1. carboxymethyl chitosan nano drug-carrying microsphere, the composition of its described carboxymethyl chitosan nano drug-carrying microsphere and content thereof are as follows by weight:
10～50 parts of carboxymethyl chitosans;
1～20 part of medicine;
1～10 part in calcium chloride;
10～20 parts of glutaraldehydes;
Wherein, described nanometer is less than one micron unit level; Described medicine is a kind of in apigenin, Quercetin, L-tryptophan and the pGenesil-1 plasmid; The preparation method of described carboxymethyl chitosan nano drug-carrying microsphere is to follow these steps to carry out:
(1) the carboxymethyl chitosan sugar aqueous solution of preparation 0.001～0.01kg/L;
(2) medicine is joined in the carboxymethyl chitosan sugar juice, stir;
(3) slowly add 0.001～0.01kg/L calcium chloride solution, in 2000～5000 rev/mins of stirrings of rotating speed, carry out first time ionomer and coat processing in advance, crosslinking time is 0.5～2h;
(4) with the volume ratio of surfactant with 1:80～180, join with the immiscible oiliness composition of water in, stir as oil mixture;
(5) the pre-mixed solution handled of coating of step (3) is joined in the oil mixture that step (4) prepares with 1:40～150, adopt boxshear apparatus to stir with 8000～20000 rev/mins of THE ADIABATIC SHEAR IN, form the water-in-oil type mixture, after the shear agitation 10～30 minutes, adding concentration is that 5～20% glutaraldehydes carry out the curing cross-linking reaction second time, obtains being coated with the carboxymethyl chitosan Nano microsphere product of medicine;
(6) with mixture centrifugalize under 10000～20000 rev/mins centrifuge speed, lower sediment is cleaned 3～5 times with petroleum ether or alcohol solvent respectively, distilled water wash 2～4 times, vacuum drying in 20～40 ℃ makes a kind of carboxymethyl chitosan nano drug-carrying microsphere;
Wherein, described surfactant is one or several mixing in Span-80, Span-85, tween-60, tween-80 and the sorbate; Described oiliness composition is one or more mixture in liquid paraffin, soybean oil, Oleum Arachidis hypogaeae semen, olive oil and the sunflower oil.
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| CN103386134B (en) * | 2013-07-22 | 2015-05-20 | 沈阳化工大学 | Preparation method for chitosan drug-carrying microspheres by ionic cross-linking method |
| CN103585113B (en) * | 2013-11-23 | 2015-04-22 | 太原理工大学 | Apigenin polylactic acid sustained release microsphere and preparation method thereof |
| CN104353131B (en) * | 2014-08-29 | 2016-09-28 | 石家庄亿生堂医用品有限公司 | A kind of Crosslinked Carboxymethyl Chitosan Resin and preparation method thereof |
| CN107216496B (en) * | 2017-06-14 | 2020-11-06 | 北京大学口腔医学院 | Amino-content-controllable chitosan material and preparation method thereof |
| CN108935921A (en) * | 2018-06-08 | 2018-12-07 | 河南蜀正园食品有限公司 | Nourishing soybean albumen powder, preparation method and its preparing the application in nutraceutical |
| CN110776922B (en) * | 2019-11-04 | 2021-03-16 | 南通大学 | Preparation method of biological control carboxymethyl chitosan soil remediation agent |
| CN111743880B (en) * | 2020-06-05 | 2022-03-08 | 浙江大学医学院附属第一医院 | Oral nano-microsphere preparation of monoclonal antibody medicines and preparation method thereof |
| CN115969897B (en) * | 2022-12-20 | 2024-06-21 | 杭州赫贝科技有限公司 | Application of rosemary extract in medicament for treating viral hepatitis |
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| CN101297654B (en) * | 2008-06-27 | 2010-12-29 | 太原理工大学 | Preparation of silver-loaded silica-chitosan compound anti-bacteria agent |
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| CN1351868A (en) * | 2001-11-15 | 2002-06-05 | 中国人民解放军第二军医大学 | Implanted slow-releasing antiseptic preparation and its preparing method |
| CN1846788A (en) * | 2006-02-16 | 2006-10-18 | 武汉理工大学 | Prepn process of nanometer carboxymethyl chitosan particle as medicine carrier |
| CN101530395A (en) * | 2009-02-25 | 2009-09-16 | 赵亮 | Method for preparing LTB-carboxymethyl chitosan influenza vaccine intranasal immunization microspheres |
| CN101716145A (en) * | 2009-12-09 | 2010-06-02 | 暨南大学 | Modified chitosan targeted medicament carrying nano microsphere and preparation method thereof |
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