CN112603910A - Mesoporous polydopamine-loaded anthocyanin nanoparticle and preparation method thereof - Google Patents
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Abstract
The invention relates to the technical field of nano materials, and discloses a mesoporous polydopamine-loaded anthocyanin nanoparticle and a preparation method thereof, wherein the nanoparticle comprises the following components in percentage by mass: 5-8: 4-9 parts of mesoporous polydopamine nanoparticles, anthocyanin and polyethylene glycol modified chitosan, wherein the mesoporous polydopamine nanoparticles are used as a carrier, the anthocyanin is adsorbed through physical and chemical adsorption, and the polyethylene glycol modified chitosan is wrapped on the outermost layer. The nano-particles can maintain the high DPPH, hydroxyl free radical scavenging activity and anticancer activity of the anthocyanin and increase the stability of the anthocyanin.
Description
Technical Field
The invention relates to the technical field of nano materials, in particular to mesoporous polydopamine-loaded anthocyanin nanoparticles and a preparation method thereof.
Background
Anthocyanin is a water-soluble natural pigment widely existing in flowers, fruits and leaves of plants, belongs to a flavonoid polyphenol compound, mulberry is a medicinal and edible traditional Chinese medicinal material, the fruits of the mulberry are rich in anthocyanin compounds, and the mulberry is one of important sources of natural pigments and has health-care and pharmacological functions of resisting oxidation, reducing blood fat, resisting atherosclerosis, enhancing immunity, improving anemia, resisting tumors and the like. However, mulberry anthocyanin is unstable, and internal and external factors such as temperature, concentration, light, pH, enzymes, oxygen, ascorbic acid, sugar and its degradation products, metal ions and self structure can affect the stability of anthocyanin. Therefore, it is required to prepare a suitable drug delivery system to solve the above problems, to improve the stability of morula anthocyanins, to prevent the drugs from being inactivated by hydrolysis and oxidation after entering into the organism, and to prolong the in vivo release time thereof.
The poly-dopamine (PDA) is a main component of natural biological pigment-melanin, can be obtained by oxidation autopolymerization of dopamine, has good stability, biodegradability, biocompatibility and photothermal conversion characteristic, and is an ideal carrier material. The polydopamine has adhesiveness, and can be coated on the surfaces of various materials. Polydopamine also has pH sensitivity and can be depolymerized in the slightly acidic environment of tumors. Mesoporous polydopamine nanoparticles (MPDA) can be prepared by a template method, can be loaded with drugs efficiently due to the pore structure and the high specific surface area, and also has good photo-thermal conversion performance. The chitosan is a cationic polymer consisting of glucosamine, has good biocompatibility, low toxicity and biodegradability, has the characteristic of intestinal mucosa adhesion, and is favorable for oral absorption of medicaments as a medicament auxiliary material. The polyethylene glycol modification is carried out on chitosan, so that the adsorption effect of plasma protein on chitosan-coated mesoporous polydopamine nanoparticles can be reduced, the ingestion of macrophages on the chitosan-coated mesoporous polydopamine nanoparticles is reduced, the process that the drug-loaded nanoparticles are removed from plasma is delayed, and the passive targeting function of the chitosan mesoporous polydopamine nanoparticles is further improved through enhanced permeation and retention effects.
Disclosure of Invention
The purpose of the invention is as follows: aiming at the problems in the prior art, the invention provides a mesoporous polydopamine-loaded anthocyanin nanoparticle and a preparation method thereof, which can keep high DPPH (dipeptidyl peptidase) and hydroxyl free radical scavenging activity and anticancer activity of anthocyanin and increase the stability of anthocyanin.
The technical scheme is as follows: the invention provides a mesoporous polydopamine-loaded anthocyanin nanoparticle which is characterized by comprising the following components in a mass ratio of 60-70: 5-8: 4-9 parts of mesoporous polydopamine nanoparticles, anthocyanin and polyethylene glycol modified chitosan, wherein the mesoporous polydopamine nanoparticles are used as a carrier, the anthocyanin is adsorbed through physical and chemical adsorption, and the polyethylene glycol modified chitosan is wrapped on the outermost layer.
Preferably, the anthocyanin is mulberry anthocyanin.
The invention also provides a preparation method of the mesoporous polydopamine-loaded anthocyanin nanoparticle, which specifically comprises the following steps: (1) adding dopamine hydrochloride and Pluronic F127 into an ethanol water solution, stirring at room temperature, then dropwise adding TMB to form a white emulsion, then adding an ammonia water solution, stirring, centrifuging, ultrasonically washing precipitates with ethanol and water for several times, and centrifuging to obtain mesoporous polydopamine nanoparticles which are marked as MPDA; wherein the mass-volume ratio of the dopamine hydrochloride, Pluronic F127, TMB and the ammonia water solution is 0.2-0.5 g: 0.8-1.2 g: 0.8-1.0 mL: 4.0-5.0 mL; (2) adding the mesoporous polydopamine nanoparticles obtained in the step (1) and anthocyanin powder into deionized water, stirring at room temperature for reaction, centrifuging, and washing with the deionized water for several times to obtain anthocyanin-loaded nanoparticles, wherein the label of the anthocyanin-loaded nanoparticles is MPDA @ MAS; the mass ratio of the mesoporous polydopamine nanoparticles to the anthocyanin powder is 12-14: 1; (3) weighing a certain amount of chitosan and polyethylene glycol, dissolving in dilute acetic acid solution, uniformly mixing, and stirring at room temperature overnight to obtain polyethylene glycol modified chitosan solution; (4) and (3) dissolving the anthocyanin-loaded nanoparticles obtained in the step (2) in an acetic acid aqueous solution, dropwise adding the polyethylene glycol modified chitosan solution obtained in the step (3), stirring at room temperature, centrifuging, and freeze-drying to obtain the mesoporous polydopamine anthocyanin-loaded nanoparticles PEG-CS @ MPDA @ MAS.
Preferably, in the step (1), the volume ratio of ethanol to water in the ethanol aqueous solution is 1: 1.
preferably, in the step (3), the mass ratio of chitosan to polyethylene glycol is 1:0.2 to 0.3.
Preferably, in the step (3), the mass fraction of the dilute acetic acid aqueous solution is 1-2%.
Preferably, in the step (4), the mass fraction of the acetic acid aqueous solution is 0.5-1%.
Preferably, in the step (4), the freeze drying temperature is-40 to-70 ℃, and the freeze drying time is 12 to 24 hours.
Has the advantages that: compared with the prior art, the invention has the following beneficial effects:
(1) the drug-loaded mesoporous polydopamine nanoparticle which can improve the stability of mulberry anthocyanin and is coated with modified chitosan is constructed by taking polydopamine as a base material, synthesizing mesoporous polydopamine nanoparticles, loading anthocyanin and coating modified chitosan molecules.
(2) The carrier Mesoporous Polydopamine (MPDA) has a high specific surface area and a nano-pore structure, has strong adsorption capacity, and can greatly improve the loading efficiency of mulberry anthocyanin through ionic bonding and pi-pi accumulation between anthocyanidins so as to solve the problem that the anthocyanidins are easy to oxidize and need large-amount administration.
(3) The modified chitosan can be absorbed and utilized by human body, has good biocompatibility and biodegradability, chitosan oligosaccharide generated in the degradation process is not accumulated in the body, almost has no immunogenicity, and simultaneously has good water solubility, the surface electrical property of the mesoporous polydopamine nano-carrier is changed into positive electricity through chitosan modification, and the adhesion of the mesoporous polydopamine nano-carrier to tumor cells is increased. The chitosan can be adsorbed in intestinal tract to delay discharge, so that the anthocyanin absorbed by human body is more, the bioavailability is improved, and the chitosan coated on the surface can improve the storage stability of the granule.
(4) The mesoporous polydopamine-loaded mulberry anthocyanin nanoparticles can slowly degrade an outer chitosan layer and a polydopamine layer in intestinal juice due to the existence of the outer chitosan, can delay the erosion of gastric acid to nanoparticles in the digestive process of the stomach, can be slowly released in small intestinal juice, and can control the transfer process of anthocyanin in the gastrointestinal tract.
(5) The mesoporous polydopamine carrier constructed by the invention is safe, non-toxic, simple to prepare, single in component, capable of improving the stability of anthocyanin and convenient to store.
Drawings
FIG. 1 is a particle size distribution diagram of mesoporous polydopamine carrier and mesoporous polydopamine-carrying mulberry anthocyanin nanoparticles;
FIG. 2 is a transmission electron microscope image of mesoporous polydopamine carrier and mesoporous polydopamine-loaded mulberry anthocyanin nanoparticles;
FIG. 3 is a nitrogen adsorption/desorption graph of mesoporous polydopamine MPDA;
FIG. 4 biological safety examination of blank vector against human normal hepatocyte LO 2;
fig. 5 is a slow release curve chart of mesoporous polydopamine-loaded mulberry anthocyanin nanoparticles in simulated gastric juice and intestinal juice.
FIG. 6 shows the antioxidant effect of mesoporous polydopamine-loaded mulberry anthocyanin nanoparticles;
FIG. 7 is a study on the stability of mesoporous polydopamine-loaded mulberry anthocyanin nanoparticles;
FIG. 8 shows the cytotoxicity effect of mesoporous polydopamine nanoparticles on human lung cancer cell A549.
Detailed Description
The present invention will be described in detail with reference to the accompanying drawings.
Embodiment 1:
the embodiment provides a preparation method of mesoporous polydopamine-loaded mulberry anthocyanin nanoparticles PEG-CS @ MPDA @ MAS, which is implemented by the following steps:
Adding 0.3 g of dopamine hydrochloride and 0.8 g of Pluronic F127 into a mixed solution of ethanol water (1: 1, v/v), stirring at room temperature, and then dropwise adding 1.0 mL of TMB to form a white emulsion; adding 4.0 mL of ammonia water solution, stirring for 30 min at 50 ℃, centrifuging, ultrasonically washing the precipitate for 3 times by using ethanol and water, and centrifuging to obtain mesoporous polydopamine nanoparticles marked as MPDA;
Mixing mesoporous polydopamine nanoparticles and mulberry anthocyanin powder according to a mass ratio of 12: adding the mixture into deionized water according to the proportion of 1, stirring and reacting for 24 h at room temperature, centrifuging, and washing with the deionized water for 3 times to obtain mulberry anthocyanin-loaded nanoparticles marked as MPDA @ MAS;
Weighing 1 g of chitosan and 0.25 g of polyethylene glycol, dissolving in 1.5% diluted acetic acid solution, uniformly mixing, and stirring at room temperature overnight to obtain polyethylene glycol modified chitosan solution; dissolving the mulberry anthocyanin-loaded nanoparticle in 100 mL of 0.5% acetic acid water, dropwise adding 20 mL of polyethylene glycol modified chitosan solution, stirring at room temperature, centrifuging, and freeze-drying at-40 ℃ for 24 h to obtain the mesoporous polydopamine mulberry anthocyanin-loaded nanoparticle PEG-CS @ MPDA @ MAS.
The prepared mesoporous polydopamine mulberry anthocyanin-loaded nanoparticle PEG-CS @ MPDA @ MAS comprises the following components in percentage by MASs of 60: 5: 4, the mesoporous polydopamine nanoparticle, the mulberry anthocyanin and the polyethylene glycol modified chitosan are used as a carrier, and the mulberry anthocyanin is physically and chemically adsorbed, and the polyethylene glycol modified chitosan is wrapped on the outermost layer.
Embodiment 2:
a preparation method of mesoporous polydopamine-loaded mulberry anthocyanin nanoparticles is specifically implemented according to the following steps:
Adding 0.3 g of dopamine hydrochloride and 1.0 g of Pluronic F127 into a mixed solution of ethanol water (1: 1, v/v), stirring at room temperature, then dropwise adding 1.0 mL of TMB to form a white emulsion, adding 4.5 mL of ammonia water solution, stirring for 40 min at 50 ℃, centrifuging, ultrasonically washing the precipitate for 5 times by using ethanol and water, and centrifuging to obtain mesoporous polydopamine nanoparticles marked as MPDA;
Mixing mesoporous polydopamine nanoparticles and mulberry anthocyanin powder according to a mass ratio of 13: adding the mixture into deionized water according to the proportion of 1, stirring and reacting for 12 h at room temperature, centrifuging, and washing with the deionized water for 3 times to obtain mulberry anthocyanin-loaded nanoparticles marked as MPDA @ MAS;
Weighing 1 g of chitosan and 0.2 g of polyethylene glycol, dissolving in 2% diluted acetic acid solution, uniformly mixing, and stirring at room temperature overnight to obtain polyethylene glycol modified chitosan solution; dissolving the mulberry anthocyanin-loaded nanoparticle in 100 mL of 0.5% acetic acid water, dropwise adding 20 mL of polyethylene glycol modified chitosan solution, stirring at room temperature, centrifuging, and freeze-drying at-60 ℃ for 16 h to obtain the mesoporous polydopamine mulberry anthocyanin-loaded nanoparticle PEG-CS @ MPDA @ MAS.
The prepared mesoporous polydopamine mulberry anthocyanin-loaded nanoparticle PEG-CS @ MPDA @ MAS comprises the following components in percentage by MASs of 65: 7: 6, the mesoporous polydopamine nanoparticle, the mulberry anthocyanin and the polyethylene glycol modified chitosan are used as carriers, the mulberry anthocyanin is physically and chemically adsorbed, and the polyethylene glycol modified chitosan is wrapped on the outermost layer.
Embodiment 3:
a preparation method of mesoporous polydopamine-loaded mulberry anthocyanin nanoparticles is specifically implemented according to the following steps:
Adding 0.4 g of dopamine hydrochloride and 1.0 g of Pluronic F127 into a mixed solution of ethanol water (1: 1, v/v), stirring at room temperature, then dropwise adding 0.8 mL of TMB to form a white emulsion, adding 5 mL of ammonia water solution, stirring for 40 min at 40 ℃, carrying out centrifugation, ultrasonically washing the precipitate for 5 times by using ethanol and water, and centrifuging to obtain mesoporous polydopamine nanoparticles, wherein the mark is MPDA;
Adding mesoporous polydopamine nanoparticles and mulberry anthocyanin powder into deionized water according to the MASs ratio of 14:1, stirring and reacting for 24 hours at room temperature, centrifuging, and washing with the deionized water for 3 times to obtain mulberry anthocyanin-loaded nanoparticles, wherein the label is MPDA @ MAS;
Weighing 1 g of chitosan and 0.3 g of polyethylene glycol, dissolving in 2% diluted acetic acid solution, uniformly mixing, and stirring at room temperature overnight to obtain polyethylene glycol modified chitosan solution; dissolving the mulberry anthocyanin-loaded nanoparticle in 100 mL of 0.5% acetic acid water, dropwise adding 20 mL of polyethylene glycol modified chitosan solution, stirring at room temperature, centrifuging, and freeze-drying at-70 ℃ for 12 h to obtain the mesoporous polydopamine mulberry anthocyanin-loaded nanoparticle PEG-CS @ MPDA @ MAS.
The prepared mesoporous polydopamine mulberry anthocyanin-loaded nanoparticle PEG-CS @ MPDA @ MAS comprises the following components in percentage by MASs of 70: 8: 7, the mesoporous polydopamine nanoparticle, the mulberry anthocyanin and the polyethylene glycol modified chitosan are used as carriers, the mulberry anthocyanin is physically and chemically adsorbed, and the polyethylene glycol modified chitosan is wrapped on the outermost layer.
And (3) analyzing the particle size distribution of the mesoporous polydopamine carrier and the mesoporous polydopamine-carried mulberry anthocyanin nanoparticles by using a Malvern laser particle size analyzer. The mesoporous polydopamine carrier and the mesoporous polydopamine mulberry anthocyanin-loaded nanoparticle are dispersed in water, and the particle size distribution is measured, as shown in figure 1, the hydrodynamic diameter sizes are respectively 120 +/-10 nm and 130 +/-10 nm.
The shapes of the mesoporous polydopamine carrier and the mesoporous polydopamine-loaded mulberry anthocyanin nanoparticles are observed by a Transmission Electron Microscope (TEM): and (3) dropwise adding 10 mu L of the solution on a surface carbon coating copper net, and naturally air-drying at room temperature. And under the condition of 200KV voltage, the appearance, the particle size and the dispersion condition of the nano particles are observed by a transmission electron microscope. The transmission electron microscope picture of the carrier is shown in fig. 2 (a), and the prepared MPDA has a narrow particle size distribution range, uniform particle size and an obvious pore structure on the surface. As shown in fig. 2 (b), it can be seen that the mesoporous polydopamine-loaded mulberry anthocyanin nanoparticles have uniform particle size and spherical shape, and the regularly distributed pore channels become fuzzy due to adsorption of mulberry anthocyanin on the surface and modification of chitosan.
MPDA nitrogen adsorption/desorption curve determination: taking an oven-dried 80 mg MPDA sample, instrumentally determining a nitrogen adsorption/desorption curve, as shown in fig. 3, the specific surface area of the prepared MPDA nanoparticles calculated by the BJH method was 68.7328 m/g.
The growth inhibition of the blank vector on human normal hepatocytes LO2 was examined by the MTT method. The cell viability of the human normal liver cell LO2 under different concentration conditions is examined under two pH conditions by using relative cell viability as an examination index by adding 200 muL/hole blank carrier solution and 200 muL/hole culture solution into an experimental group and 200 muL/hole culture solution into a control group by using the human normal liver cell LO 2. As shown in FIG. 4, when the concentration of the hollow nano-particles reaches 1000. mu.g/mL, the survival rate of the human normal hepatocyte LO2 cells is also above 80%, which indicates that the carrier material has good biocompatibility within the concentration of 0.98-1000. mu.g/mL.
A dialysis bag method is adopted to investigate the release condition of the mesoporous polydopamine-loaded anthocyanin nanoparticles in simulated gastric juice and simulated intestinal juice. Putting 1 mL of mesoporous polydopamine-loaded anthocyanin nanoparticle suspension into a dialysis bag, wherein release media are simulated artificial gastric juice and artificial intestinal juice, oscillating at constant temperature of 37 ℃, sampling at different time points, and drawing an accumulated drug release curve. The experimental result is shown in fig. 5, and it can be seen from fig. 5 that the release rate of the mesoporous polydopamine-supported anthocyanin nanoparticle in simulated gastric fluid is higher than that in simulated intestinal fluid, the cumulative release rate is greater than 80%, and the release is relatively complete. The mesoporous polydopamine-loaded anthocyanin nanoparticles are slowly released from the beginning of an experiment and are gradually stable along with the lapse of time, so that the mesoporous polydopamine-loaded anthocyanin nanoparticles have an obvious effect on the aspect of anthocyanin controlled release.
And (3) determining the oxidation resistance of the mulberry anthocyanin by adopting a DPPH method. Respectively sucking 2 mL mesoporous polydopamine-loaded mulberry anthocyanin nanoparticle suspension and 2 mL LDPPH solution test tubes, mixing and shaking uniformly, placing for 30 min in a dark environment, measuring the absorbance, and taking Vc solution as a positive control. As shown in FIG. 6, the DPPH radical scavenging ability of each sample is gradually enhanced with the gradual increase of the sample concentration, the increase trend of the scavenging rate becomes gentle when the addition amount is in the range of 5-20. mu.g/mL concentration, and the scavenging rate tends to be stable without increasing when the concentration reaches a certain level. And in the range of the tested concentration, the clearance rates of the anthocyanin-loaded nanoparticles and the free anthocyanin are higher than that of a positive control Vc. Therefore, the anthocyanin-loaded nanoparticle has stronger DPPH free radical elimination activity.
Thermal stability study: a certain amount of mesoporous polydopamine-loaded mulberry anthocyanin nanoparticle suspension is placed in a water bath at 50 ℃ and is subjected to an experiment in the dark, and compared with an unloaded mulberry anthocyanin solution, the content is respectively measured by an ultraviolet spectrophotometer method on the 0 th day, the 1 st day, the 2 nd day, the 3 rd day, the 4 th day and the 5 th day. As shown in fig. 7, the residual rate of the mesoporous poly dopamine-loaded morula anthocyanins is higher than that of the unloaded morula anthocyanins.
The toxicity effect of free anthocyanin and PEG-CS @ MPDA @ MAS on human lung cancer cell A549 cancer cell is examined through MTT test. The results are shown in fig. 8, and the anthocyanins showed significant dose-dependent inhibition of human lung cancer cell a549 under two pH conditions. This enhanced anti-tumor effect of anthocyanins upon carrier loading may be due to the excellent anti-proliferative activity of the chelated anthocyanins and the synergistic anti-tumor effect of anthocyanins and the surface modified chitosan coating.
The above embodiments are merely illustrative of the technical concepts and features of the present invention, and the purpose of the embodiments is to enable those skilled in the art to understand the contents of the present invention and implement the present invention, and not to limit the protection scope of the present invention. All equivalent changes and modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.
Claims (8)
1. The mesoporous polydopamine-loaded anthocyanin nanoparticle is characterized by comprising the following components in percentage by mass of 60-70: 5-8: 4-9 parts of mesoporous polydopamine nanoparticles, anthocyanin and polyethylene glycol modified chitosan, wherein the mesoporous polydopamine nanoparticles are used as a carrier, the anthocyanin is adsorbed through physical and chemical adsorption, and the polyethylene glycol modified chitosan is wrapped on the outermost layer.
2. The mesoporous polydopamine-loaded anthocyanin nanoparticle as claimed in claim 1, wherein the anthocyanin is mulberry anthocyanin.
3. A preparation method of mesoporous polydopamine-loaded anthocyanin nanoparticles is characterized by comprising the following steps:
(1) adding dopamine hydrochloride and Pluronic F127 into an ethanol water solution, stirring at room temperature, then dropwise adding TMB to form a white emulsion, then adding an ammonia water solution, stirring, centrifuging, ultrasonically washing precipitates with ethanol and water for several times, and centrifuging to obtain mesoporous polydopamine nanoparticles which are marked as MPDA;
wherein the mass-volume ratio of the dopamine hydrochloride, Pluronic F127, TMB and the ammonia water solution is 0.2-0.5 g: 0.8-1.2 g: 0.8-1.0 mL: 4.0-5.0 mL;
(2) adding the mesoporous polydopamine nanoparticles obtained in the step (1) and anthocyanin powder into deionized water, stirring at room temperature for reaction, centrifuging, and washing with the deionized water for several times to obtain anthocyanin-loaded nanoparticles, wherein the label of the anthocyanin-loaded nanoparticles is MPDA @ MAS;
the mass ratio of the mesoporous polydopamine nanoparticles to the anthocyanin powder is 12-14: 1;
(3) weighing a certain amount of chitosan and polyethylene glycol, dissolving in dilute acetic acid solution, uniformly mixing, and stirring at room temperature overnight to obtain polyethylene glycol modified chitosan solution;
(4) and (3) dissolving the anthocyanin-loaded nanoparticles obtained in the step (2) in an acetic acid aqueous solution, dropwise adding the polyethylene glycol modified chitosan solution obtained in the step (3), stirring at room temperature, centrifuging, and freeze-drying to obtain the mesoporous polydopamine anthocyanin-loaded nanoparticles PEG-CS @ MPDA @ MAS.
4. The preparation method of the mesoporous polydopamine-supported anthocyanin nanoparticle as claimed in claim 3, wherein in the step (1), the volume ratio of ethanol to water in the ethanol aqueous solution is 1: 1.
5. the preparation method of the mesoporous polydopamine-supported anthocyanin nanoparticle as claimed in claim 3, wherein in the step (3), the mass ratio of chitosan to polyethylene glycol is 1: 0.2-0.3.
6. The preparation method of the mesoporous polydopamine-supported anthocyanin nanoparticle as claimed in claim 5, wherein in the step (3), the mass fraction of the dilute acetic acid aqueous solution is 1-2%.
7. The preparation method of the mesoporous polydopamine-supported anthocyanin nanoparticle as claimed in claim 3, wherein in the step (4), the mass fraction of the acetic acid aqueous solution is 0.5-1%.
8. The preparation method of the mesoporous polydopamine anthocyanin-loaded nanoparticle as claimed in any one of claims 3 to 7, wherein in the step (4), the freeze-drying temperature is-40 to-70 ℃, and the freeze-drying time is 12 to 24 hours.
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| CN113925834A (en) * | 2021-10-26 | 2022-01-14 | 深圳市第二人民医院(深圳市转化医学研究院) | Polydopamine-lactoferrin drug carrier and application thereof |
| CN114522181A (en) * | 2022-01-25 | 2022-05-24 | 中山大学 | Amino acid modified mesoporous polydopamine nanoparticle and preparation method and application thereof |
| CN115109348A (en) * | 2022-08-17 | 2022-09-27 | 曾荣华 | Yellowing-resistant breathable plastic track and preparation method thereof |
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| CN112603910B (en) | 2022-03-22 |
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