CN115368645A - Nanoparticle assembly with pH responsiveness and preparation method thereof - Google Patents
Nanoparticle assembly with pH responsiveness and preparation method thereof Download PDFInfo
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- CN115368645A CN115368645A CN202211011109.6A CN202211011109A CN115368645A CN 115368645 A CN115368645 A CN 115368645A CN 202211011109 A CN202211011109 A CN 202211011109A CN 115368645 A CN115368645 A CN 115368645A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
- C08L5/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
- C08L5/16—Cyclodextrin; Derivatives thereof
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Abstract
The invention discloses a nano particle assembly with pH responsiveness and a preparation method thereof. The preparation method comprises the steps of mixing the sugammadex sodium and the chitosan under an acidic condition, constructing a nanoparticle assembly by electrostatic interaction of the sugammadex sodium and the chitosan, depolymerizing the assembly by adjusting the pH of the solution to be alkaline, and reforming the assembly when the solution is adjusted back to be acidic, so that the preparation method has good reciprocating circulation. The invention has the advantages that: the preparation method of the assembly is simple, the environmental pollution is small, and the cost is low; the dynamic and reversible characteristics of electrostatic interaction endow the assembly with good stimulus response performance; is closer to the living body, and lays a good foundation for the application of the biological system.
Description
Technical Field
The invention belongs to the technical field of nano materials, and relates to preparation and characterization of a sugammadex and chitosan nanoparticle assembly, wherein the assembly can have certain responsiveness to pH.
Background
The nano-particles constructed by cyclodextrin and chitosan have unique structure and excellent biochemical performance, have attracted wide attention at home and abroad in recent years, and it is not difficult to find that most of the cyclodextrin/chitosan nano-carriers reported at present are constructed based on a covalent strategy, and the cyclodextrin is covalently connected to the chitosan through reaction sites of primary amine groups at C-2 position or primary alcohol groups at C-6 position of the chitosan to form a molecular carrier. The carrier has the inclusion performance and the transmission characteristic of cyclodextrin and the controlled release capacity of an assembly matrix. However, covalent strategies still have some limitations, such as complicated molecular design, often using toxic solvents, long synthesis time, high cost, difficult separation, the possibility of covalent linkage changing the reactivity of the responsive group, etc. And the shortcomings of covalent strategies are just compensated by non-covalent interactions.
Sugammadex sodium is a modified carboxylated gamma-cyclodextrin known as 6-per-deoxy-6-per (2-carboxyethyl) thio-gamma-cyclodextrin sodium salt of formula: c 72 H 104 O 48 S 8 Na 8 (ii) a Molecular weight: 2178.006 is a cyclic molecular structure composed of 8 adjacent glucose molecules, has lipophilic inner cavity and hydrophilic surface, and has 8 negative charges. The chitosan is a polysaccharide polymer with the second highest content in nature, has the good characteristics of no toxicity, good biocompatibility, biodegradability, low price and the like, and has positive charge under the acidic condition, and the positive charge is removed under the alkaline condition to show neutrality. Thus, the sugammadex sodium can form an assembly through electrostatic interaction with the chitosan with positive charge under acidic conditions, and the assembly is depolymerized under alkaline conditions because the electrostatic interaction between the sugammadex sodium and the chitosan does not exist.
Disclosure of Invention
The invention aims to provide a preparation method of a pH-responsive nanoparticle assembly, wherein the assembly is constructed by utilizing sugammadex and chitosan through electrostatic interaction and has good responsiveness to pH value.
The purpose of the invention can be realized by the following technical scheme:
a pH-responsive nanoparticle assembly is characterized in that building units are sugammadex sodium and chitosan with the deacetylation degree of 95%, and the pH-responsive nanoparticle assembly is constructed through electrostatic interaction, wherein the content of the sugammadex sodium is 14.04% -52.13%, and the content of the chitosan is 47.87% -85.96%.
Preferably, the content of the components of the sugammadex sodium and the chitosan is 52.13% and 47.87%, respectively.
A method for preparing a pH-responsive nanoparticle assembly, comprising the steps of:
1) Dissolving chitosan with deacetylation degree of 95% in hydrochloric acid solution with pH of 1, adding water to constant volume to obtain 500 μ g/mL, and adjusting pH of the solution with sodium hydroxide particles to obtain chitosan mother liquor with pH of 5.3.
2) Dissolving sugammadex sodium with distilled water with pH of 5.3 to obtain 1 × 10 -3 mol/L of sugammadex mother liquor.
3) Dripping 1mol/L hydrochloric acid solution into water to adjust the pH value of the solution to 5.3.
4) Mixing a certain amount of pH-adjusted chitosan and sulgammadex mother liquor, adding distilled water with pH equal to 5.3, and diluting to constant volume until the concentration of sulgammadex is 3 × 10 -6 mol/L, chitosan concentration of 6 u g/mL, obtained pH value of 5.3 with pH response nanoparticle assembly solution.
The prepared assembly has responsiveness to pH, and when the pH of the solution is adjusted to be alkaline to depolymerize the assembly and the solution is adjusted to be acidic again, the assembly is reformed and has good reciprocating cyclicity.
The nanoparticle assembly constructed by utilizing sugammadex sodium and chitosan through electrostatic interaction has the following beneficial effects:
(1) The complex chemical synthesis and the complex purification in the preparation process can be effectively simplified, and the method has less pollution to the environment and low cost.
(2) The dynamic and reversible characteristics of electrostatic interaction endow the assembly with good stimulus response performance, not only can realize effective release of load molecules, but also shows good targeting selectivity.
(3) Is closer to the living body, and lays a good foundation for the application of the biological system.
Drawings
FIG. 1 is a graph of the critical aggregation concentration of sugammadex sodium at a concentration of immobilized chitosan of 20 μ g/mL;
FIG. 2 shows the concentration of sodium biosulfate at 3X 10 -6 At mol/L, a critical aggregation concentration graph of chitosan;
FIG. 3 is a dynamic light scattering diagram of the nanoparticle assembly;
FIG. 4 is a scanning electron microscope image of the nanoparticle assembly;
FIG. 5 is a transmission electron microscope image of the nanoparticle assembly;
FIG. 6 is a graph of the transmittance of the nanoparticle assembly as a function of pH at 400 nm;
FIG. 7 is a graph of the transmittance of the nanoparticle assembly at 400nm adjusted with pH;
FIG. 8 is a scanning electron micrograph of the nanoparticle assembly at a pH of 10.18;
FIG. 9 is a transmission electron micrograph of the nanoparticle assembly at pH 10.13.
Detailed Description
The invention is further described below with reference to the accompanying drawings.
A pH-responsive nanoparticle assembly is characterized in that building units are sugammadex sodium and chitosan with the deacetylation degree of 95%, and the pH-responsive nanoparticle assembly is constructed through electrostatic interaction, wherein the content of the sugammadex sodium is 14.04% -52.13%, and the content of the chitosan is 47.87% -85.96%.
The preparation method comprises the following steps:
1) Firstly, 0.025g of chitosan with the deacetylation degree of 95% is dissolved in 3mL of hydrochloric acid with the pH value of 1, the volume is determined by distilled water to be 500 mu g/mL, and then the pH value of the solution is adjusted by adding sodium hydroxide, so that the chitosan mother liquor with the pH value of 5.3 is finally obtained. At the same time, the sugammadex sodium with molecular weight of 2177.97 is dissolved by distilled water with pH of 5.3 to be prepared into the concentration of 1 × 10 -3 mol/L of sugammadex mother liquor. Wherein the distilled water with pH of 5.3 is prepared by adding appropriate amount of hydrochloric acid dropwiseAnd distilled water.
2) mu.L of chitosan and 30. Mu.L of sugammadex mother liquor were mixed, and 9.850mL of distilled water at pH 5.3 were added to obtain 10mLpH 5.3 assembly solution.
FIG. 1 is a graph showing UV transmittance at 400nm of a solution measured at a concentration of immobilized chitosan of 20. Mu.g/mL and increasing concentrations of sugammadex sodium. It was observed that the UV transmission curve shows an inflection point at a solubility of 0.001mM for sugammadex sodium, i.e. a Critical Aggregation Concentration (CAC) of 0.001mM for sugammadex sodium.
FIG. 2 shows the concentration of sodium biosulfate at 3X 10 -6 And (3) gradually increasing the concentration of the chitosan, and determining an ultraviolet transmission curve chart of the solution at 400 nm. It was observed that the solution permeation rate was lowest when the chitosan concentration reached 6. Mu.g/mL, from which it can be seen that the sodium sugammadex-chitosan nanoparticle assemblies reached the most in the solution at a chitosan concentration of 6. Mu.g/mL.
The particle size and morphology of the nanoparticle assembly are as follows: the characterization is carried out by dynamic light scattering, a scanning electron microscope and a transmission electron microscope respectively.
Fig. 3 is a graph of dynamic light scattering of pH-responsive nanoparticle assemblies of sugammadex sodium and chitosan, showing that the average particle size of the assemblies is 196nm.
Fig. 4 is a scanning electron microscope image of the pH-responsive nanoparticle assembly of sugammadex sodium and chitosan.
Fig. 5 is a transmission electron microscope image of pH-responsive nanoparticle assemblies of sugammadex sodium and chitosan.
Response of the nanoparticle assembly to pH: the prepared assembly has responsiveness to pH, and when the pH of the solution is alkaline, the assembly is depolymerized; when the pH value of the solution is adjusted to be acidic again, the assembly is formed again, and the good reciprocating property is achieved.
Figure 6 is a graph of system transmittance versus pH at 400nm wavelength for pH-responsive nanoparticle assemblies of sugammadex sodium and chitosan. As can be seen, the transmittance of the solution was the lowest at pH 5.3, and the transmittance increased with increasing pH. The explanation for this phenomenon is that the assembly gradually disaggregates; when the pH of the system is gradually adjusted from alkaline to acidic, the permeability has a tendency to decrease, which means that the assembly is regenerated again in the process of changing the pH of the solution from alkaline to acidic.
FIG. 7 is a graph showing the transmittance of the nanoparticle assembly at 400nm adjusted with pH, and it can be seen that the solution of the assembly has a low transmittance under acidic conditions, and a high transmittance under alkaline conditions, meaning that the assembly is depolymerized under alkaline conditions, and the transmittance decreases again when the solution is adjusted to acidic conditions, and the assembly has good pH cycling performance.
FIG. 8 is a scanning electron micrograph of the nanoparticle assembly at pH 10.18, from which it is apparent that the nanoparticles have substantially completely depolymerized when the pH of the solution is adjusted to alkaline.
Fig. 9 is a transmission electron microscope image of the nanoparticle assembly at a pH of 10.13, from which it can be seen that the nanoparticles are depolymerized when the pH of the solution is adjusted to alkaline, and it can be seen that the nanoparticles constructed by the present invention have pH responsiveness, corresponding to the scanning electron microscope experiment.
Claims (3)
1. A nano particle assembly with pH responsiveness is characterized in that a building unit is formed by electrostatic interaction of sugammadex sodium and chitosan with the deacetylation degree of 95%, the content of the sugammadex sodium is 14.04% -52.13%, and the content of the chitosan component is 47.87% -85.96%.
2. The nanoparticle assembly of claim 1, wherein the sugammadex sodium and the chitosan comprise 52.13% and 47.87% respectively.
3. A method for preparing the pH-responsive nanoparticle assembly of claim 1, comprising the steps of:
1) Dissolving 25mg of chitosan with the deacetylation degree of 95% in 4mL of hydrochloric acid solution with the pH value of 1, adding water to fix the volume to 50mL to prepare 500 microgram/mL, and adjusting the pH value of the solution by using a certain amount of sodium hydroxide particles to obtain a chitosan mother solution with the pH value of 5.3;
2) Dissolving 6.53mg sugammadex sodium in 3mL of distilled water with pH of 5.3 to obtain 1 × 10 -3 mol/L of sugammadex mother liquor;
3) Dripping 1mol/L hydrochloric acid solution into water to adjust the pH value of the solution to 5.3;
4) Mixing a certain amount of chitosan and the mother liquor of sugammadex sodium, adding distilled water with pH equal to 5.3 to reach volume concentration of sugammadex sodium of 3 × 10 -6 mol/L, chitosan concentration of 6 u g/mL, obtained pH value of 5.3 with pH response nanoparticle assembly solution.
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Citations (6)
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| CN104738815A (en) * | 2015-02-11 | 2015-07-01 | 浙江中烟工业有限责任公司 | Nano cyclodextrin composite additive reducing phenol in cigarette smoke and preparation method and application thereof |
| CN104815332A (en) * | 2015-05-15 | 2015-08-05 | 南开大学 | pH-responsive binary supramolecular nanoparticles, and preparation method and application thereof |
| CN108014344A (en) * | 2017-12-06 | 2018-05-11 | 华中科技大学 | PH and the chitosan nano pharmaceutical carrier and preparation method of temperature-responsive and application |
| CN108379590A (en) * | 2018-05-03 | 2018-08-10 | 青岛大学 | A kind of preparation method of internal self assembly target medicine carrier |
| CN109908367A (en) * | 2019-04-30 | 2019-06-21 | 南开大学 | Application of the supramolecular nanoparticles that sulfanilic acid-beta-cyclodextrin mediates in terms of the control release of insulin |
| CN111715192A (en) * | 2020-06-30 | 2020-09-29 | 李金妹 | Magnetic beta-cyclodextrin grafted chitosan adsorption material and preparation method thereof |
-
2022
- 2022-08-23 CN CN202211011109.6A patent/CN115368645A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104738815A (en) * | 2015-02-11 | 2015-07-01 | 浙江中烟工业有限责任公司 | Nano cyclodextrin composite additive reducing phenol in cigarette smoke and preparation method and application thereof |
| CN104815332A (en) * | 2015-05-15 | 2015-08-05 | 南开大学 | pH-responsive binary supramolecular nanoparticles, and preparation method and application thereof |
| CN108014344A (en) * | 2017-12-06 | 2018-05-11 | 华中科技大学 | PH and the chitosan nano pharmaceutical carrier and preparation method of temperature-responsive and application |
| CN108379590A (en) * | 2018-05-03 | 2018-08-10 | 青岛大学 | A kind of preparation method of internal self assembly target medicine carrier |
| CN109908367A (en) * | 2019-04-30 | 2019-06-21 | 南开大学 | Application of the supramolecular nanoparticles that sulfanilic acid-beta-cyclodextrin mediates in terms of the control release of insulin |
| CN111715192A (en) * | 2020-06-30 | 2020-09-29 | 李金妹 | Magnetic beta-cyclodextrin grafted chitosan adsorption material and preparation method thereof |
Non-Patent Citations (1)
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