CN102335575B - Microcapsules of a kind of layer assembly and preparation method thereof - Google Patents
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Abstract
The present invention relates to a kind of bio-compatibility microcapsules and preparation method thereof, particularly relate to a kind of based on Schiff 's base key layer assembly bio-compatibility microcapsules and preparation method thereof, it is characterized in that wall components used is bio-compatible and biodegradable polysaccharide and derivative thereof, define Schiff 's base key between wall components, do not use extra poisonous crosslinking agent.The microcapsules prepared than ever mutually, the microcapsules that the present invention obtains have both good stability, bio-compatible, and biodegradable is nontoxic, the permeability of autofluorescence and pH response, and without the need to using crosslinking agent.
Description
Technical field
The object of this invention is to provide a kind of method based on Schiff 's base key layer assembly bio-compatibility microcapsules.
Background technology
Microcapsules are the materials with geometry in particular of space in capsule and its space outerpace being kept apart and being formed by film forming matter, and its shape, based on spherical, also can be ellipse, square or rectangular, polygon and various irregularly shaped.The inside of microcapsules can be fill, and also can be hollow.The cyst wall of microcapsules is made up of macromolecular material that is natural or that synthesize or inorganic material usually, and the thickness of cyst wall is generally between a few nanometer is to several microns.Capsule interior or exterior space is isolated by the cyst wall of microcapsules, if be wrapped in capsule by material, physical chemistry, the biology performance of material itself then can not be affected, and plays a protective role again simultaneously, be isolated from the outside to wrapped material.The obstruct that cyst wall possesses and osmotic adjustment performance, can reduce or regulate and control the rate of release of embedding substance, thus play the effect of slowly-releasing and Co ntrolled release.Therefore, due to all functions that microcapsules possess, make scientists according to the needs be wrapped in the difference of physical property or practical application, use or develop different cyst materials and preparation method.The preparation method of traditional microcapsules can be divided into chemical method, physical method and physico-chemical process principle.Chemical method refers to prepares capsule structure by the mode of the chemical reaction such as interfacial polymerization, in-situ polymerization; And spray-on process, pot bag method and air suspension film forming method etc. all belong to the scope of Physical; Physicochemical method mainly comprises coacervation, dry bath method and oil-phase separating method etc.
No matter microcapsules prepared by said method, be the microcapsules of nucleocapsid structure or hollow, all accurately cannot control, cause the yardstick of microcapsules and wall thickness to there is larger polydispersity in the size and wall thickness etc. of microcapsules.Laminated assembling technology combines with template and prepares that microcapsules can form the form of capsule, size, cyst wall, wall thickness, structure, transparent performance and function of surface regulate and control.This method has the advantages such as wide material sources, method of operating are simple, with low cost, is huge breakthroughs to the Synthesis and applications of microcapsules.
The film forming motive force of the classical laminated assembling technology electrostatic force mainly between polyelectrolyte molecules or charge species.The multiple material with electric charge, as synthesis and natural polyelectrolyte, nanoparticle, protein, enzyme, phosphatide, dyestuff, metal ion and surfactant etc., all can be assembled in hollow microcapsule, thus prepare the microcapsules with multiple performance and function.But the composition of cyst wall is no longer confined to charge species, so the driving force of assembling also extends to the non-electrostatic effects such as hydrogen bond action, hydrophobic effect, covalent cross-linking effect or DNA hybridism from electrostatic interaction.Because the intensity of covalent bond is more much bigger than the intensity of electrostatic force, hydrogen bond etc., the microcapsules therefore formed by covalent effect have unique advantage in stability, and this is also that it is widely used in the reason of assembling microcapsules in recent years.Prepared the method for microcapsules by covalent bond, mostly adopt chemical cross-linking agent technically, as glutaraldehyde, polyepoxide, carbodiimides etc.Gao Changyou etc. mediate the assembling of PAH (PAH) at manganese carbonate particle surface by glutaraldehyde, obtain the PAH one pack system microcapsules of glutaraldehyde cross-linking.But well-known, above-mentioned crosslinking agent is mostly poisonous, and easy stripping also enters in human body, thus harm is greatly produced to human body.
In addition, existing microcapsule wall material, is normally made up of macromolecular material that is natural or synthesis.But, these materials can not be biodegradable mostly, to human body and bad environmental, adopt biosynthesis or biologically-derived macromolecular material (as sodium alginate, poly-D-lysine, DNA, collagen, gelatin, shitosan, glucan, heparin and derivative thereof etc.) then can obtain biocompatible microcapsules.
For these reasons, the present invention proposes a kind of without the need to additionally adding crosslinking agent, preparation is stable, the method for bio-compatible, biodegradable microcapsules.
Summary of the invention
The present invention prepares on the basis of microcapsules utilizing laminated assembling technology and template to combine in the past, based on the microcapsules of Schiff 's base key assembling bio-compatible.
The invention provides a kind of method based on Schiff 's base key layer assembly bio-compatibility microcapsules, comprise the following steps:
A template particles is distributed in the solution containing component 2 and adsorbs by (), remove the component 2 of not adsorbing;
(b) by step a) in the particle that obtains be distributed to containing component 1 solution again in adsorb, remove unreacted component 1;
C () repeats step a and the b of at least 2 times, component 1 or 2 can be identical with the last time, also can be different from the last time, the optional step comprising removing template particles.
According to the method for the embodiment of the present invention, wherein, described component 1 or 2 is sugar or sugared derivative.
According to the method for the embodiment of the present invention, wherein, the derivative that the part or all of hydroxyl that described component 1 is sugar is oxidized and obtain.
According to the method for the embodiment of the present invention, wherein, described component 2 is shitosan.
According to the method for the embodiment of the present invention, wherein, the described sugar for being oxidized is starch, cellulose, glucan.
According to the method for the embodiment of the present invention, wherein, described sugar is by sodium periodate oxidation.
According to the method for the embodiment of the present invention, wherein, described template particles can be manganese carbonate, calcium carbonate, cadmium carbonate, silica, polystyrene colloid particle, melamino-formaldehyde colloidal particle etc., or medicine crystal.
According to the method for the embodiment of the present invention, wherein, described template particles can be ellipse, square, rectangle, polygon and various irregularly shaped.
The microcapsules tool that method according to the present invention obtains has the following advantages,
(1) good stability: dissolved soon after being soaked in 0.1M hydrochloric acid and 0.1M sodium hydroxide solution by the alginate/chitosan microcapsules of electrostatic assembly, and assembled by Schiff 's base key (CHI/ADA) 5 microcapsules in 0.1M hydrochloric acid and 0.1M sodium hydroxide solution, soak 24 hours after still keep original pattern, prove the good stability of the microcapsules that the present invention is based on the assembling of Schiff 's base key
(2) bio-compatible, biodegradable: wall components is the derivative of polysaccharide or polysaccharide, is bio-compatible and biodegradable material,
(3) can autofluorescence: owing to defining Schiff 's base key between wall components, thus can autofluorescence,
(4) there is the permeability of pH response: define Schiff 's base key between wall components, Schiff 's base key is unstable under acidic condition, easily degrades,
(5) extra poisonous crosslinking agent is not used: do not use glutaraldehyde, the crosslinking agent that carbodiimides etc. are poisonous,
Accompanying drawing explanation
Reaction equation in Fig. 1 (CHI/ADA) 5 microcapsules preparation process between wall components.
Fig. 2 microcapsules preparation process schematic diagram.
Fig. 3 is the scanning electron microscopy of natural drying (CHI/ADA) 5 microcapsules.
Fig. 4 is the transmission electron microscopy figure of natural drying (CHI/ADA) 5 microcapsules, obviously can see capsule classical fold in the dry state, indicate its hollow structure.
Fig. 5 is (CHI/ADA) 5 laser co-focusing micrograph of microcapsules.
Fig. 6 is (CHI/ADA) 5 infiltrative laser co-focusing micrograph of glucan (20kDa) of marking FITC of microcapsules in the system of different acidity.Can obviously see, be the glucan of the FITC mark of 20kDa for molecular weight, (pH=5) can permeate in acid condition; And cannot permeate under neutral (pH=7) and alkalescence (pH=9) condition.
Fig. 7 soaks (CHI/ADA) after 24 hours 5 laser co-focusing micrograph of microcapsules in 0.1M hydrochloric acid (A) and 0.1M NaOH (B) solution.Dissolve soon after being soaked in 0.1M hydrochloric acid and 0.1M sodium hydroxide solution by the alginate/chitosan microcapsules of electrostatic assembly, and assembled by Schiff 's base key (CHI/ADA) 5 microcapsules in 0.1M hydrochloric acid and 0.1M sodium hydroxide solution, soak 24 hours after still keep original pattern, prove the good stability of the microcapsules that the present invention is based on the assembling of Schiff 's base key.
Detailed description of the invention
Embodiment 1
(1) preparation has the oxidized sodium alginate (alginate dialdehyde, ADA) of two aldehyde structures
With distilled water, 5g sodium alginate is mixed with the solution that concentration is 2.5wt%, adds 5.4g sodium metaperiodate wherein, after lucifuge reaction 24h, add proper amount of glycol cessation reaction.Make product Precipitation with 200mL absolute ethyl alcohol after solution mixes with 10g sodium chloride, suction filtration also uses deionized water dissolution precipitation, and again separate out with ethanol, suction filtration, repeats this step 3 time, product is loaded surface plate, and 40 DEG C of vacuum drying 24h, can obtain ADA.
(2) based on the bio-compatibility microcapsules of Schiff 's base key assembling
First, by manganese carbonate particle dispersion to the 1mg/mL shitosan (chitosan containing 0.5M sodium chloride, CHI) in solution, after vibration absorption 30min, centrifugation, after abundant washing, be distributed in the 1mg/mL ADA solution containing 0.5M sodium chloride again and adsorb 30min, on the aldehyde radical on ADA and particle surface, the amino of CHI reacts, thus, ADA has received particle surface by the reaction between CHI, washs 3 times.Again this particle dispersion is adsorbed 30min in the 1mg/mL CHI solution containing 0.5M sodium chloride, the amino of same CHI can react with excessive aldehyde radical in particle surface ADA, thus CHI is fixed on particle surface, washs 3 times.So complete an assembling cycle, repeat successively, until the required number of plies.Then, by the disodium EDTA solution of the manganese carbonate particle dispersion to 0.1M that are coated with multi-layer C HI/ADA, can dissolve until obtain hollow microcapsule in batches, deposit with for subsequent use for 4 DEG C.
Wherein, the pH sensitiveness of microcapsules is the glucans of the FITC mark taking molecular weight as 20kDa is fluorescent probe molecule, utilizes FV1000 confocal system (Olympus, Japan) to characterize.In experiment, the microcapsule suspensions of preparation is distributed in the cushioning liquid of different pH, then the glucan (Mw ~ 20kDa) that the capsule suspension liquid be under different acidity marks with equivalent FITC is mixed, after 15min, use laser confocal microscope to observe rapidly.In general, if capsule and outside fluorescence intensity basic simlarity, just think that this capsule can permeate this dyestuff; If the inner chamber fluorescence intensity of capsule is starkly lower than outside, then think that this capsule is impermeable to this dyestuff.
Embodiment 2
(1) preparation has the oxycellulose (dialdehyde cellulose, DAC) of two aldehyde structures
With distilled water, 5g cellulose is mixed with the solution that concentration is 2.5wt%, adds 5.4g sodium metaperiodate wherein, after lucifuge reaction 24h, add proper amount of glycol cessation reaction.Make product Precipitation with 200mL absolute ethyl alcohol after solution mixes with 10g sodium chloride, suction filtration also uses deionized water dissolution precipitation, and again separate out with ethanol, suction filtration, repeats this step 3 time, product is loaded surface plate, and 40 DEG C of vacuum drying 24h, can obtain DAC.
(2) based on the bio-compatibility microcapsules of Schiff 's base key assembling
First, by polystyrene colloid particle dispersion to the 1mg/mL shitosan (chitosan containing 0.5M sodium chloride, CHI) in solution, after vibration absorption 6h, centrifugation, after abundant washing, be distributed in the 1mg/mL DAC solution containing 0.5M sodium chloride again and adsorb 6h, on the aldehyde radical on DAC and particle surface, the amino of CHI reacts, thus, DAC has received particle surface by the reaction between CHI, washs 3 times.Again this particle dispersion is adsorbed 6h in the 1mg/mL CHI solution containing 0.5M sodium chloride, the amino of same CHI can react with excessive aldehyde radical in particle surface DAC, thus CHI is fixed on particle surface, washs 3 times.So complete an assembling cycle, repeat successively, until the required number of plies.Then, by the disodium EDTA solution of the manganese carbonate particle dispersion to 0.1M that are coated with multi-layer C HI/DAC, can dissolve until obtain hollow microcapsule in batches, deposit with for subsequent use for 4 DEG C.
Embodiment 3
(1) preparation has the oxidized starch (dialdehyde starch, DAS) of two aldehyde structures
With distilled water, 5g starch is mixed with the solution that concentration is 2.5wt%, adds 5.4g sodium metaperiodate wherein, after lucifuge reaction 24h, add proper amount of glycol cessation reaction.Make product Precipitation with 200mL absolute ethyl alcohol after solution mixes with 10g sodium chloride, suction filtration also uses deionized water dissolution precipitation, and again separate out with ethanol, suction filtration, repeats this step 3 time, product is loaded surface plate, and 40 DEG C of vacuum drying 24h, can obtain DAS.
(2) based on the bio-compatibility microcapsules of Schiff 's base key assembling
First, calcium carbonate particle is distributed to the 5mg/mL shitosan (chitosan containing 0.5M sodium chloride, CHI) in solution, after vibration absorption 30min, centrifugation, after abundant washing, be distributed in the 5mg/mL DAS solution containing 0.5M sodium chloride again and adsorb 30min, on the aldehyde radical on DAS and particle surface, the amino of CHI reacts, thus, DAS has received particle surface by the reaction between CHI, washs 3 times.Again this particle dispersion is adsorbed 30min in the 5mg/mLCHI solution containing 0.5M sodium chloride, the amino of same CHI can react with excessive aldehyde radical in particle surface DAS, thus CHI is fixed on particle surface, washs 3 times.So complete an assembling cycle, repeat successively, until the required number of plies.Then, by the disodium EDTA solution of the manganese carbonate particle dispersion to 0.1M that are coated with multi-layer C HI/DAS, can dissolve until obtain hollow microcapsule in batches, deposit with for subsequent use for 4 DEG C.
Embodiment 4
(1) preparation has the DHA (Dialdehyde Hyaluronic Acid, DHA) of two aldehyde structures
With distilled water, 5g hyaluronic acid is mixed with the solution that concentration is 2.5wt%, adds 5.4g sodium metaperiodate wherein, after lucifuge reaction 12h, add proper amount of glycol cessation reaction.Make product Precipitation with 200mL absolute ethyl alcohol after solution mixes with 10g sodium chloride, suction filtration also uses deionized water dissolution precipitation, and again separate out with ethanol, suction filtration, repeats this step 3 time, product is loaded surface plate, and 40 DEG C of vacuum drying 24h, can obtain DHA.
(2) based on the bio-compatibility microcapsules of Schiff 's base key assembling
First, by cadmium carbonate particle dispersion to the 3mg/mL shitosan (chitosan containing 0.5M sodium chloride, CHI) in solution, after vibration absorption 12h, centrifugation, after abundant washing, be distributed in the 3mg/mL DHA solution containing 0.5M sodium chloride again and adsorb 12h, on the aldehyde radical on DHA and particle surface, the amino of CHI reacts, thus, DHA has received particle surface by the reaction between CHI, washs 3 times.Again this particle dispersion is adsorbed 12h in the 3mg/mLCHI solution containing 0.5M sodium chloride, the amino of same CHI can react with excessive aldehyde radical in particle surface DHA, thus CHI is fixed on particle surface, washs 3 times.So complete an assembling cycle, repeat successively, until the required number of plies.Then, by the disodium EDTA solution of the manganese carbonate particle dispersion to 0.1M that are coated with multi-layer C HI/DHA, can dissolve until obtain hollow microcapsule in batches, deposit with for subsequent use for 4 DEG C.
Embodiment 5
(1) preparation has the DHP (Dialdehyde Heparin, DHP) of two aldehyde structures
With distilled water, 5g heparin is mixed with the solution that concentration is 3wt%, adds 5.5g sodium metaperiodate wherein, after lucifuge reaction 16h, add proper amount of glycol cessation reaction.Make product Precipitation with 200mL absolute ethyl alcohol after solution mixes with 15g sodium chloride, suction filtration also uses deionized water dissolution precipitation, and again separate out with ethanol, suction filtration, repeats this step 3 time, product is loaded surface plate, and 40 DEG C of vacuum drying 24h, can obtain DHP.
(2) based on the bio-compatibility microcapsules of Schiff 's base key assembling
First, silicon dioxide granule is distributed to the 2mg/mL shitosan (chitosan containing 0.5M sodium chloride, CHI) in solution, after vibration absorption 4h, centrifugation, after abundant washing, be distributed in the 2mg/mL DHP solution containing 0.5M sodium chloride again and adsorb 4h, on the aldehyde radical on DHP and particle surface, the amino of CHI reacts, thus, DHP has received particle surface by the reaction between CHI, washs 3 times.Again this particle dispersion is adsorbed 4h in the 2mg/mL CHI solution containing 0.5M sodium chloride, the amino of same CHI can react with excessive aldehyde radical in particle surface DHP, thus CHI is fixed on particle surface, washs 3 times.So complete an assembling cycle, repeat successively, until the required number of plies.Then, by the disodium EDTA solution of the manganese carbonate particle dispersion to 0.1M that are coated with multi-layer C HI/DHP, can dissolve until obtain hollow microcapsule in batches, deposit with for subsequent use for 4 DEG C.
Claims (8)
1. microcapsules, it is characterized in that, comprise the macromolecule layer of alternating layers assembling, component 1 contains multiple amino containing multiple aldehyde radical, component 2, in layer assembly process, component 1 is the combination of one or more many aldehyde compounds, component 2 is combinations of one or more multiamino compounds, the alternatively stacked described layer containing multiple aldehyde radical is identical or different, the alternatively stacked described layer containing multiple amino is identical or different, and defines multiple Schiff 's base key between described multiple aldehyde radical of described component 1 and described multiple amino of described component 2; Described microcapsules are optionally containing core, and described core is polymer template particle; At surface of microcapsule optionally by biological targeting molecular modification; The preparation method of described microcapsules, comprises the following steps:
A template particles is distributed in the solution containing component 2 and adsorbs by (), remove the component 2 of not adsorbing;
(b) by step a) in the particle that obtains be distributed to containing component 1 solution again in adsorb, remove unreacted component 1;
C () repeats step a and the b of at least 2 times, component 1 or 2 is identical with the last time, or different from the last time, the optional step comprising removing template particles; Wherein, in layer assembly process, between described multiple aldehyde radical of described component 1 and described multiple amino of described component 2, define multiple Schiff 's base key.
2. microcapsules as claimed in claim 1, is characterized in that component 1 or 2 is sugar or sugared derivative.
3. microcapsules as claimed in claim 2, is characterized in that the derivative that part or all of hydroxyl that component 1 is sugar is oxidized and obtain.
4. microcapsules as claimed in claim 1, described component 2 is shitosan.
5. microcapsules as claimed in claim 3, the sugar wherein for being oxidized is starch, cellulose or glucan.
6. microcapsules as claimed in claim 5, wherein said sugar is by sodium periodate oxidation.
7. the microcapsules according to any one of claim 1-6, wherein microcapsules are the microcapsules of pH sensitive.
8. the microcapsules according to any one of claim 1-6 are as the purposes of pharmaceutical carrier.
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