CN104922675A - Preparation method of graphene oxide composite material mediated by carboxymethyl chitosan and modified by hyaluronic acid - Google Patents
Preparation method of graphene oxide composite material mediated by carboxymethyl chitosan and modified by hyaluronic acid Download PDFInfo
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- CN104922675A CN104922675A CN201510270469.1A CN201510270469A CN104922675A CN 104922675 A CN104922675 A CN 104922675A CN 201510270469 A CN201510270469 A CN 201510270469A CN 104922675 A CN104922675 A CN 104922675A
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Abstract
The invention relates to a preparation method of a graphene oxide composite material mediated by carboxymethyl chitosan and modified by hyaluronic acid. The method comprises the following steps: (1) chemically bonding graphene oxide (GO) and carboxymethyl chitosan (CMC) in distilled water under the actions of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride(EDC HCl) and N-hydroxysuccinimide (NHS) serving as activating agents, and performing dialysis and freeze drying to synthesize GO-CMC; (2) dissolving the hyaluronic acid into the distilled water, adding the EDC.HCl and the NHS serving as the activating agents for activating; (3) preparing the GO-CMC into a water solution, gradually adding the water solution into activated hyaluronic acid (HA) dropwise, stirring, and performing dialysis and freeze drying to obtain GO-CMC-HA. The preparation method is simple in preparation process, is implemented under the experimental conditions of normal temperature and normal pressure, and is easy to operate. The prepared graphene oxide composite material for serving as a carrier of medicine has a very good use value.
Description
Technical field
The invention belongs to the field of graphene oxide composite material, particularly a kind of preparation method containing hyaluronic acid decorated graphene oxide composite material mediated by carboxymethyl chitosan.
Background technology
Since Graphene was found from 2004, be considered to, in fields such as composite, sensor, the energy, there is important application prospect because of the electricity of its excellence, optics, calorifics and mechanical performance, become the focus of nm regime research in recent years.And the research of biomedical sector is started late, but development rapidly.The application of this field is more is through chemical oxidation, ultrasonic disperse and obtained graphene oxide by graphite powder.Graphene oxide has larger specific surface area, is suitable as pharmaceutical carrier, improves carrying drug ratio.The more important thing is, its surface, containing a large amount of oxygen-content active functional groups, as hydrophilic radicals such as hydroxyl, carboxyl, carbonyl, epoxy radicals, thus has good aqueous stability and biocompatibility.But it in normal saline because the existence of electron screening effect is easily reunited, make it be hindered in the performance of the potential using value of biomedical sector.This drawback can be improved by the method for finishing, and its surperficial a large amount of functional group is for herein is provided probability.Graphene oxide composite material through functionalized modification is finally expected to the pharmaceutical carrier serving as controllable release, has good application prospect in the field such as biological medicine and diagnosis.
Carboxymethyl chitosan (Carboxymethyl chitosan, CMC) be a kind of water-solubility chitosan derivative, it is a kind of chemical industry synthetic occurred in recent years, there is many characteristics having using value, as antibacterial anti-infection, preservation, blood fat reducing and prevent and treat the pharmacological actions such as arteriosclerosis, therefore in medicine, chemical industry, environmental protection, health product, having important meaning, is also that Recent study obtains one of more chitosan derivatives.Compared with chitosan, because it is both containing weak base cation (-NH
3 +) group, again containing weak acid anion (-COO
-) group, be a kind of amphipathic electrolyte, therefore it has better biocompatibility and biodegradability, is more suitable for being applied to biomedical sector.In addition, it has flexible molecular skeleton, and the carboxyl on it and unsubstituted amino can as linking arms friendly between graphene oxide and bioactive molecule, for mediating the functional modification of Graphene.
Hyaluronic acid is a kind of unique acid mucopolysaccharide, has another name called the acid of glass urea, demonstrates multiple important physiological function with the molecular structure of its uniqueness and physicochemical property in body, as lubricating joint, the permeability etc. regulating blood vessel wall.It is the important foundation material that skin water is tender, itself be also a kind of composition of human body, have special water retention, deal is more up to 100 times of itself weight, be the best material of the occurring in nature moisture retention that finds at present, be called as desirable nature moisturizing factor.It also has the biochemical drug of higher clinical value, is widely used in all kinds of ophthalmologic operation, as Lens implantation, corneal transplantation and resisting glaucoma operation etc.Also can be used for treatment of arthritis and accelerating wound healing in addition.Graphene oxide after hyaluronic acid decorated has good biocompatibility, is conducive to the biologic applications of material, and gained functionalized nano material can be used as drug delivery carrier.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of preparation method containing hyaluronic acid decorated graphene oxide composite material mediated by carboxymethyl chitosan, and the method is simple to operate, and reaction condition is gentle.The graphene oxide composite material that the method prepares can drug loading, for the Co ntrolled release of medicine.
A kind of preparation method containing hyaluronic acid decorated graphene oxide composite material mediated by carboxymethyl chitosan of the present invention, comprising:
(1) graphene oxide GO is dispersed in distilled water, ultrasonic, under the condition stirred, add 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide hydrochloride EDCHCl and N-hydroxy-succinamide NHS, activation 3h; Wherein, the mass ratio of GO graphene oxide and EDCHCl and NHS is 1:0.5:0.25 ~ 1:1:0.5;
(2) activation adds carboxymethyl chitosan CMC aqueous solution after terminating, and stirs 24h, dialysis, and lyophilization, obtains GO-CMC; Wherein, the mass ratio of graphene oxide and carboxymethyl chitosan is 1:1 ~ 1:2;
(3) hyaluronic acid HA is dissolved in distilled water, adds EDCHCl and NHS and activate 3h; Wherein, the mol ratio of hyaluronic acid and activator EDCHCl and NHS is 1:1:0.8;
(4) GO-CMC obtained in step (2) is dissolved in distilled water, dropwise join in the hyaluronic acid of activation in step (3), stirring reaction 24h, dialysis, lyophilization, obtains containing hyaluronic graphene oxide composite material GO-CMC-HA; Wherein, the mass ratio of GO-CMC and HA is 1:5 ~ 1:10.
In described step (1), soak time is 3h.
The time of stirring in described step (2) is 24h.
In described step (3), the time of activation is 3h.
Mixing time in described step (4) is 24h.
Dialysis in described step (2) and step (4), for adopting bag filter, is first dialyse in the buffer of 7-8 at pH, then dialyses in distilled water.
Described preparation method is carried out at normal temperatures and pressures.
To the preparation containing hyaluronic graphene oxide composite material mediated by carboxymethyl chitosan, we have done some tests: (1) SEM test result
SEM test result shows: graphene oxide still keeps its lamellar structure later through hyaluronic acid decorated, namely modifies and occurs over just surface, do not change the structure of Graphene itself.See accompanying drawing 1.
(2) NMR test result
NMR test result shows: take graphene oxide as template, CMC and HA molecule is successfully bonded on the surface of graphene oxide.See accompanying drawing 2.
(3) TGA test result
TGA test result shows: according to tail end analytic process, and choose 900 DEG C for accounting temperature, the CMC being modified at surface of graphene oxide is about 12.5%, HA and is about 5.6%.See accompanying drawing 3.
(4) Zeta potential test result
Zeta potential test result shows: graphene oxide through HA modify after, in electronegativity and current potential raise, illustrate that biocompatibility improves, and system dispersibility is better.See
table 1.
beneficial effect
(1) the present invention adopts the method for chemical bonding, and synthesis is containing hyaluronic acid decorated graphene oxide composite material, and preparation method is simple, and experiment condition is gentle;
(2) the present invention prepares graphene oxide composite material and overcomes graphene oxide exists easily reunion in normal saline defect due to electron screening effect; Carboxymethyl chitosan, as mediation, by hyaluronic modification, improves the biocompatibility of material, and tool applies the potentiality that it does the analysis of follow-up related experiment;
(3) graphene oxide composite material that the present invention prepares possesses the potentiality as pharmaceutical carrier and control delivery, is expected to improve carrying drug ratio, realizes Co ntrolled release.
Accompanying drawing explanation
Fig. 1 is the SEM figure of the GO-CMC-HA obtained in embodiment 1;
Fig. 2 is GO-CMC, GO-CMC-HA and CMC in embodiment 2, HA
1h-NMR collection of illustrative plates; Wherein, (a) is for CMC's
1h-NMR collection of illustrative plates, (b) is for HA's
1h-NMR collection of illustrative plates, (c) is for GO-CMC's
1h-NMR collection of illustrative plates, (d) is for GO-CMC-HA's
1h-NMR collection of illustrative plates;
Fig. 3 is the TGA collection of illustrative plates of GO, GO-CMC, GO-CMC-HA in embodiment 3.
Detailed description of the invention
Below in conjunction with specific embodiment, set forth the present invention further.Should be understood that these embodiments are only not used in for illustration of the present invention to limit the scope of the invention.In addition should be understood that those skilled in the art can make various changes or modifications the present invention, and these equivalent form of values fall within the application's appended claims limited range equally after the content of having read the present invention's instruction.
Embodiment 1
(1) add in 8mL distilled water by 20.7mg GO, ultrasonic disperse is to even.Then under magnetic agitation condition, add 15.6mg EDCHCl and 7.8mg NHS, carry out stir-activating reaction 3h.Separately 28.8mg CMC is mixed with 5mg/mL aqueous solution, under magnetic agitation condition, dropwise adds and above-mentionedly activated in GO dispersion liquid, stirring reaction 24h under room temperature state.Finally reactant liquor is transferred in bag filter (MW=100,000), by dialysis by unreacted impurity and by-product removing, first dialyses 3 times with PBS buffer, each 2L, then dialyse 6 times with ultra-pure water.Obtain GO-CMC after finally carrying out lyophilization process to sample, it is stand-by that sealing is stored in 4 DEG C of refrigerators.
(2) by 99.3mg HA (MW=6,800) be dissolved in 10mL distilled water, add 2.8mg EDCHCl and 1.4mg NHS, carry out stir-activating 3h, separately 21.4mg GO-CMC is mixed with 5mg/mL aqueous solution, under magnetic agitation condition, dropwise add in the HA aqueous solution after activation, stirring reaction 24h under room temperature condition.Finally reactant liquor is transferred in bag filter (MW=8,000-14,000), by dialysis by unreacted impurity and by-product removing, first dialyses 3 times with PBS buffer, each 2L, then dialyse 6 times with ultra-pure water.Obtain GO-CMC-HA after finally carrying out lyophilization process to sample, sealing is stored in 4 DEG C of refrigerators.
(3) scanning electron microscope sem of end product is characterized as shown in Figure 1, can find out that graphene oxide still keeps its lamellar structure later through hyaluronic acid decorated, namely modify and occur over just surface, do not change the structure of Graphene itself.
Embodiment 2
(1) add in 10mL distilled water by 49.8mg GO, ultrasonic disperse is to even.Then under magnetic agitation condition, add 31.7mg EDCHCl and 15.8mg NHS, carry out stir-activating reaction 3h.Separately 63.4mg CMC is mixed with 5mg/mL aqueous solution, under magnetic agitation condition, dropwise adds and above-mentionedly activated in GO dispersion liquid, stirring reaction 24h under room temperature state.Finally reactant liquor is transferred in bag filter (MW=100,000), by dialysis by unreacted impurity and by-product removing, first dialyses 3 times with PBS buffer, each 2L, then dialyse 6 times with ultra-pure water.Obtain GO-CMC after finally carrying out lyophilization process to sample, it is stand-by that sealing is stored in 4 DEG C of refrigerators.
(2) by 327.1mg HA (MW=6,800) be dissolved in 30mL distilled water, add 9.2mg EDCHCl and 4.4mg NHS, carry out stir-activating 3h, separately 51.2mg GO-CMC is mixed with 5mg/mL aqueous solution, under magnetic agitation condition, dropwise add in the HA aqueous solution after activation, stirring reaction 24h under room temperature condition.Finally reactant liquor is transferred in bag filter (MW=8,000-14,000), by dialysis by unreacted impurity and by-product removing, first dialyses 3 times with PBS buffer, each 2L, then dialyse 6 times with ultra-pure water.Obtain GO-CMC-HA after finally carrying out lyophilization process to sample, sealing is stored in 4 DEG C of refrigerators.
(3) each step product GO-CMC, GO-CMC-HA and CMC, HA are tested
1as shown in Figure 2, GO does not have obvious characteristic peak to H-NMR collection of illustrative plates in shown scope, after CMC modifies, in figure (c) chemical shift be the appearance of δ=4.5 ~ 5.0ppm place be amide proton peak on CMC.Further after HA modifies, occurred in figure (d) glucuronic acid relevant to HA and NAG proton peak.These results show that HA and GO-CMC successfully links together.
Embodiment 3
(1) add in 15mL distilled water by 80.3mg GO, ultrasonic disperse is to even.Then under magnetic agitation condition, add 51.2mg EDCHCl and 25.8mg NHS, carry out stir-activating reaction 3h.Separately 90mg CMC is mixed with 5mg/mL aqueous solution, under magnetic agitation condition, dropwise adds and above-mentionedly activated in GO dispersion liquid, stirring reaction 24h under room temperature state.Finally reactant liquor is transferred in bag filter (MW=100,000), by dialysis by unreacted impurity and by-product removing, first dialyses 3 times with PBS buffer, each 2L, then dialyse 6 times with ultra-pure water.Obtain GO-CMC after finally carrying out lyophilization process to sample, it is stand-by that sealing is stored in 4 DEG C of refrigerators.
(2) by 401.3mg HA (MW=6,800) be dissolved in 40mL distilled water, add 11.3mg EDCHCl and 5.4mg NHS, carry out stir-activating 3h, separately 81.2mg GO-CMC is mixed with 5mg/mL aqueous solution, under magnetic agitation condition, dropwise add in the HA aqueous solution after activation, stirring reaction 24h under room temperature condition.Finally reactant liquor is transferred in bag filter (MW=8,000-14,000), by dialysis by unreacted impurity and by-product removing, first dialyses 3 times with PBS buffer, each 2L, then dialyse 6 times with ultra-pure water.Obtain GO-CMC-HA after finally carrying out lyophilization process to sample, sealing is stored in 4 DEG C of refrigerators.
(3) to the thermogravimetic analysis (TGA) TGA collection of illustrative plates of each step product GO, GO-CMC, GO-CMC-HA test as shown in Figure 3, choose 900 DEG C for accounting temperature, the CMC being modified at graphenic surface is about 12.5%, HA and is about 5.6%.
Embodiment 4
(1) add in 10mL distilled water by 21.2mg GO, ultrasonic disperse is to even.Then under magnetic agitation condition, add 16.2mg EDCHCl and 8.3mg NHS, carry out stir-activating reaction 3h.Separately 30.8mg CMC is mixed with 5mg/mL aqueous solution, under magnetic agitation condition, dropwise adds and above-mentionedly activated in GO dispersion liquid, stirring reaction 24h under room temperature state.Finally reactant liquor is transferred in bag filter (MW=100,000), by dialysis by unreacted impurity and by-product removing, first dialyses 3 times with PBS buffer, each 2L, then dialyse 6 times with ultra-pure water.Obtain GO-CMC after finally carrying out lyophilization process to sample, it is stand-by that sealing is stored in 4 DEG C of refrigerators.
(2) by 122.9mg HA (MW=6,800) be dissolved in 15mL distilled water, add 3.5mg EDCHCl and 1.7mg NHS, carry out stir-activating 3h, separately 23.6mg GO-CMC is mixed with 5mg/mL aqueous solution, under magnetic agitation condition, dropwise add in the HA aqueous solution after activation, stirring reaction 24h under room temperature condition.Finally reactant liquor is transferred in bag filter (MW=8,000-14,000), by dialysis by unreacted impurity and by-product removing, first dialyses 3 times with PBS buffer, each 2L, then dialyse 6 times with ultra-pure water.Obtain GO-CMC-HA after finally carrying out lyophilization process to sample, sealing is stored in 4 DEG C of refrigerators.
(3) Zeta potential of GO, GO-CMC, GO-CMC-HA is as shown in table 1.Graphene oxide is electronegativity, illustrate that itself there is certain biocompatibility, after CMC modifies, because CMC surface exists unsubstituted amino, current potential is caused slightly to raise, then after HA modifies, current potential falls after rise, illustrate and modify successfully, and end-product is electronegativity, possess certain biocompatibility.
The Zeta potential of GO, GO-CMC, GO-CMC-HA in table 1 embodiment 4
| Materials | GO | GO-CMC | GO-HA |
| Zeta(mv) | -42.5±1.4 | -36.9±0.6 | -41.5±9.6 |
Claims (6)
1. the preparation method containing hyaluronic acid decorated graphene oxide composite material mediated by carboxymethyl chitosan, comprising:
(1) graphene oxide GO is dispersed in distilled water, ultrasonic, under the condition stirred, add 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide hydrochloride EDCHCl and N-hydroxy-succinamide NHS, activation 3h; Wherein, the mass ratio of GO graphene oxide and EDCHCl and NHS is 1:0.5:0.25 ~ 1:1:0.5;
(2) activation adds carboxymethyl chitosan CMC aqueous solution after terminating, and stirs 24h, dialysis, and lyophilization, obtains GO-CMC; Wherein, the mass ratio of graphene oxide and carboxymethyl chitosan is 1:1 ~ 1:2;
(3) hyaluronic acid HA is dissolved in distilled water, adds EDCHCl and NHS and activate 3h; Wherein, the mol ratio of hyaluronic acid and activator EDCHCl and NHS is 1:1:0.8;
(4) GO-CMC obtained in step (2) is dissolved in distilled water, dropwise join in the hyaluronic acid of activation in step (3), stirring reaction 24h, dialysis, lyophilization, obtains containing hyaluronic graphene oxide composite material GO-CMC-HA; Wherein, the mass ratio of GO-CMC and HA is 1:5 ~ 1:10.
2. a kind of preparation method containing hyaluronic acid decorated graphene oxide composite material mediated by carboxymethyl chitosan according to claim 1, it is characterized in that, in described step (1), soak time is 3h.
3. a kind of preparation method containing hyaluronic acid decorated graphene oxide composite material mediated by carboxymethyl chitosan according to claim 1, it is characterized in that, the time of stirring in described step (2) is 24h.
4. a kind of preparation method containing hyaluronic acid decorated graphene oxide composite material mediated by carboxymethyl chitosan according to claim 1, it is characterized in that, in described step (3), the time of activation is 3h.
5. a kind of preparation method containing hyaluronic acid decorated graphene oxide composite material mediated by carboxymethyl chitosan according to claim 1, it is characterized in that, the mixing time in described step (4) is 24h.
6. a kind of preparation method containing hyaluronic acid decorated graphene oxide composite material mediated by carboxymethyl chitosan according to claim 1, it is characterized in that, dialysis in described step (2) and step (4) is for adopting bag filter, first is dialyse in the buffer of 7-8 at pH, then dialyses in distilled water.
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| CN105381501A (en) * | 2015-12-15 | 2016-03-09 | 日照天一生物医疗科技有限公司 | Degradable biological composite haemostasis membrane and preparation method thereof |
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| CN113603895A (en) * | 2021-08-16 | 2021-11-05 | 南京工业大学 | Preparation method of chitosan-graphene oxide hybrid material |
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Application publication date: 20150923 |