CN112546026A - Hollow mesoporous polydopamine-loaded liposoluble pigment nanoparticle and preparation method thereof - Google Patents
Hollow mesoporous polydopamine-loaded liposoluble pigment nanoparticle and preparation method thereof Download PDFInfo
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- CN112546026A CN112546026A CN202011617998.1A CN202011617998A CN112546026A CN 112546026 A CN112546026 A CN 112546026A CN 202011617998 A CN202011617998 A CN 202011617998A CN 112546026 A CN112546026 A CN 112546026A
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Abstract
The invention relates to the technical field of nano materials, and discloses hollow mesoporous polydopamine-loaded fat-soluble pigment nanoparticles and a preparation method thereof, wherein the nanoparticles comprise the following components in percentage by mass: 9-14: 6-11 parts of mesoporous polydopamine nanoparticles, fat-soluble pigment and polyethylene glycol modified chitosan, wherein the mesoporous polydopamine nanoparticles are used as a carrier, the fat-soluble pigment is adsorbed by physical and chemical adsorption, and the polyethylene glycol modified chitosan is wrapped on the outermost layer. The hollow mesoporous polydopamine has a higher specific surface area, a nano-pore structure and an internal hollow structure, can adsorb hydrophobic drugs, greatly improves the loading efficiency of the fat-soluble pigment, has pH sensitivity and a gating effect, responds to the pH value of a tumor part, improves the effective fat-soluble pigment concentration in a tumor cell, and delays the effective action time of the fat-soluble pigment; improve the bioavailability and in-vivo and in-vitro stability of the fat-soluble pigment and improve the tumor treatment effect.
Description
Technical Field
The invention relates to the technical field of nano materials, in particular to hollow mesoporous polydopamine-loaded fat-soluble pigment nanoparticles and a preparation method thereof.
Background
Curcumin is a polyphenol substance extracted from rhizome of Curcuma longa, Curcuma zedoaria, Curcuma aromatica, etc. belonging to the genus Curcuma of the family Zingiberaceae. Researches report that curcumin has wide pharmacological effects of resisting tumors and fibrosis, resisting oxidation, resisting inflammation, inhibiting bacteria, reducing blood fat, protecting liver and the like, has very low toxicity, and is more and more valued by experts and scholars at home and abroad. Lycopene is a carotenoid extracted from plants such as tomatoes, watermelons and the like, is a fat-soluble natural haematochrome, belongs to hydrocarbon, has strong antioxidant function, has the effects of protecting heart and cerebral vessels, enhancing immunity, resisting tumors and the like, has a prevention or treatment effect on neurodegenerative diseases and mental diseases such as Parkinson, epilepsy and depression, is basically non-toxic in a dosage range, is favored in health care value, and has become a hot spot of domestic and foreign research. Curcumin and lycopene belong to fat-soluble pigments, and the fat-soluble pigments are insoluble in water, are not easy to absorb after oral administration, have serious liver first-pass effect, and have high metabolism and clearing rate in vivo, so the bioavailability is low, the stability is poor, and the visible light is easy to decompose, so a proper drug delivery system needs to be prepared to solve the problems, improve the water solubility and the stability of the fat-soluble pigments, prevent the drugs from being hydrolyzed and oxidized to be inactivated after entering an organism, and prolong the in vivo release time of the drugs.
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 a large amount of catechol and amino functional groups on the surface, has strong adhesion 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. Hollow mesoporous polydopamine nanoparticles (HPDA) can be prepared by a hard template method, and can be loaded with drugs efficiently due to the fact that the hollow mesoporous polydopamine nanoparticles (HPDA) have a high specific surface area, a pore structure and an internal hollow structure, and also have 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 hollow mesoporous polydopamine-loaded fat-soluble pigment nanoparticles and a preparation method thereof, which can improve the bioavailability of fat-soluble pigment, improve the water solubility and stability of the fat-soluble pigment and improve the bioavailability of the fat-soluble pigment, and the drug-loaded nanoparticles are expected to achieve the aims of tumor penetration and directional slow release.
The technical scheme is as follows: the invention provides hollow mesoporous polydopamine-loaded fat-soluble pigment nanoparticles which are characterized by comprising the following components in parts by mass of 45-48: 9-14: 6-11 mesoporous polydopamine nanoparticles, a fat-soluble pigment and polyethylene glycol modified chitosan, wherein the mesoporous polydopamine nanoparticles are used as a carrier, the fat-soluble pigment is adsorbed by physical and chemical adsorption, and the polyethylene glycol modified chitosan is wrapped on the outermost layer.
Preferably, the fat-soluble pigment is curcumin or lycopene.
The invention also provides a preparation method of the hollow mesoporous polydopamine-loaded liposoluble pigment nanoparticle, which specifically comprises the following steps: (1) adding dopamine hydrochloride and Pluronic F127 into an ethanol aqueous solution, stirring uniformly at room temperature, adding silica particles, then adding TMB dropwise to form a white emulsion, then adding an ammonia aqueous solution, stirring, centrifuging, ultrasonically washing the precipitate with ethanol and water for several times, then adding the precipitate into a hydrofluoric acid aqueous solution, etching, and centrifuging to obtain hollow mesoporous polydopamine nanoparticles marked as HPDA; wherein the mass-volume ratio of the dopamine hydrochloride, Pluronic F127, silicon dioxide, TMB and ammonia water solution is 0.3-0.5 g: 1.0-1.2 g: 20-30 mg: 0.6-1.0 mL: 4.0-5.0 mL; (2) adding the hollow mesoporous polydopamine nanoparticles obtained in the step (1) and fat-soluble pigment powder into anhydrous DMSO, stirring and reacting at room temperature, centrifuging, washing with a mixed solution of DMSO and deionized water and washing with deionized water for several times to obtain fat-soluble pigment-loaded nanoparticles; the mass ratio of the hollow mesoporous polydopamine nanoparticles to the fat-soluble pigment powder is 5-8: 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 fat-soluble pigment-loaded nanoparticle 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 hollow mesoporous polydopamine fat-soluble pigment-loaded nanoparticle.
Preferably, in the step (1), the volume ratio of ethanol to water in the ethanol aqueous solution is 1: 1.
preferably, in the step (1), the mass fraction of the hydrofluoric acid aqueous solution is 3-5%.
Preferably, in the step (2), in the mixed solution of DMSO and deionized water, the volume ratio of DMSO to deionized water is 3-4: 7 to 8.
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 invention takes polydopamine as a base material, constructs a drug-loaded hollow mesoporous polydopamine nanoparticle which can improve the bioavailability of fat-soluble pigment and takes modified chitosan as a coating through the synthesis of hollow mesoporous polydopamine nanoparticles, the loading of the fat-soluble pigment and the coating of modified chitosan molecules, improves the water solubility and stability of the fat-soluble pigment and the bioavailability of the fat-soluble pigment, and is expected to achieve the aims of tumor penetration and directional slow release.
(2) The carrier hollow mesoporous polydopamine (HPDA) has a higher specific surface area, a nanometer pore structure and an internal hollow structure than mesoporous polydopamine, has strong adsorption capacity, can adsorb hydrophobic drug fat-soluble pigment on the surface and the hollow inner wall of the hollow mesoporous polydopamine, can generate pi-pi electron transition, forms carbonyl bonds (the fat-soluble pigment is curcumin) or generates a michael addition reaction (the fat-soluble pigment is lycopene) with fat-soluble pigment molecules, and can greatly improve the loading efficiency of the polydopamine on the fat-soluble pigment by combining physical adsorption and chemical adsorption.
(3) The hollow mesoporous polydopamine-loaded fat-soluble pigment nanoparticle disclosed by the invention enables the release of fat-soluble pigment to have pH responsiveness and a gating effect, can effectively respond to the pH value of a tumor part, improves the effective fat-soluble pigment concentration in a tumor cell, delays the effective action time of the fat-soluble pigment, can improve the poor taste of the fat-soluble pigment, and avoids that bitter components of some fat-soluble pigments are dissolved in the mouth.
(4) 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 hollow mesoporous polydopamine nano-carrier is changed into positive electricity through chitosan modification, and the adhesion of the hollow mesoporous polydopamine nano-carrier to tumor cells is increased. The chitosan can be adsorbed in intestinal tract to delay discharge, so that the fat-soluble pigment 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.
(5) The hollow mesoporous polydopamine carrier constructed by the invention is safe, nontoxic, simple to prepare, single in component, capable of improving the stability of fat-soluble pigment and convenient to store.
Drawings
FIG. 1 is a particle size distribution diagram of a hollow mesoporous polydopamine carrier and hollow mesoporous polydopamine curcumin-loaded nanoparticles;
FIG. 2 is a transmission electron microscope image of a hollow mesoporous polydopamine carrier and hollow mesoporous polydopamine curcumin-loaded nanoparticles;
FIG. 3 FTIR spectra of curcumin, mesoporous polydopamine carrier and mesoporous polydopamine-loaded curcumin nanoparticles;
FIG. 4 is a nitrogen adsorption/desorption graph of hollow mesoporous polydopamine HPDA;
FIG. 5 biological safety examination of blank vector against human normal hepatocyte LO 2;
FIG. 6 is a slow release curve diagram of hollow mesoporous polydopamine curcumin-loaded nanoparticles in simulated gastric juice and intestinal juice;
FIG. 7 shows the cytotoxic effect of hollow mesoporous polydopamine nanoparticles on human colon cancer cells HCT-116;
FIG. 8 is a particle size distribution diagram of a hollow mesoporous polydopamine carrier and hollow mesoporous polydopamine-loaded lycopene nanoparticles;
FIG. 9 is a transmission electron microscope image of a hollow mesoporous polydopamine carrier and hollow mesoporous polydopamine-loaded lycopene nanoparticles;
FIG. 10 is a graph showing the photostability of lycopene, mesoporous polydopamine-loaded lycopene nanoparticles;
FIG. 11 is a slow release curve diagram of hollow mesoporous polydopamine-loaded lycopene nanoparticles in simulated gastric and intestinal fluids;
FIG. 12 shows the cytotoxic effect of hollow mesoporous polydopamine nanoparticles on hepatoma carcinoma cells HepG 2.
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 hollow mesoporous polydopamine curcumin-loaded nanoparticle PEG-CS @ HPDA @ CUR, which is implemented by the following steps:
step 1, synthesis of HPDA
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, adding 20 mg of silicon dioxide particles after uniformly stirring, and then dropwise adding 0.8 mL of TMB to form 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, adding the precipitate into 3% hydrofluoric acid water solution for etching, centrifuging, and washing by using deionized water for several times to obtain the hollow mesoporous polydopamine nanoparticles marked as HPDA.
Mixing hollow mesoporous polydopamine nanoparticles and curcumin powder according to a mass ratio of 7:1, stirring and reacting for 24 hours at room temperature, centrifuging, washing with a mixed solution of DMSO and deionized water (3: 7, v/v) once and washing with deionized water for 3 times to obtain curcumin-loaded nanoparticles marked as HPDA @ CUR;
step 3, synthesis of PEG-CS @ HPDA @ CUR
Weighing 1 g of chitosan and 0.25 g of polyethylene glycol, dissolving in 1% diluted acetic acid solution, uniformly mixing, and stirring at room temperature overnight to obtain polyethylene glycol modified chitosan solution; dissolving the curcumin-loaded nanoparticles 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 hollow mesoporous polydopamine curcumin-loaded nanoparticles PEG-CS @ HPDA @ CUR.
The prepared hollow mesoporous polydopamine curcumin-loaded nanoparticle PEG-CS @ HPDA @ CUR comprises the following components in percentage by mass: 9: 6, the hollow mesoporous polydopamine nanoparticle is used as a carrier, and the curcumin is physically and chemically adsorbed, and the polyethylene glycol modified chitosan is coated on the outermost layer.
Embodiment 2:
a preparation method of mesoporous polydopamine curcumin-loaded nanoparticles is specifically implemented according to the following steps:
step 1, synthesis of HPDA
Adding 0.5 g of dopamine hydrochloride and 1.2 g of Pluronic F127 into a mixed solution of ethanol water (1: 1, v/v), stirring at room temperature, adding 25 mg of silicon dioxide particles after uniformly stirring, then dropwise adding 1.0 mL of TMB to form a white emulsion, adding 4.0 mL of ammonia water solution, stirring at 50 ℃ for 30 min, centrifuging, ultrasonically washing the precipitate for 5 times by using ethanol and water, adding the precipitate into 4% hydrofluoric acid water solution for etching, centrifuging, and washing with deionized water for several times to obtain the hollow mesoporous polydopamine nanoparticles, wherein the mark is HPDA.
Mixing hollow mesoporous polydopamine nanoparticles and curcumin powder according to a mass ratio of 8: 1, stirring and reacting for 12 hours at room temperature, centrifuging, washing once with a mixed solution of DMSO and deionized water (4: 7, v/v) and washing 5 times with deionized water to obtain curcumin-loaded nanoparticles marked as HPDA @ CUR;
step 3, synthesis of PEG-CS @ HPDA @ CUR
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 curcumin-loaded nanoparticles 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 hollow mesoporous polydopamine curcumin-loaded nanoparticles PEG-CS @ HPDA @ CUR.
The prepared hollow mesoporous polydopamine curcumin-loaded nanoparticle PEG-CS @ HPDA @ CUR comprises the following components in percentage by mass: 10: 7, the hollow mesoporous polydopamine nanoparticle is used as a carrier, and the curcumin is physically and chemically adsorbed, and the polyethylene glycol modified chitosan is coated on the outermost layer.
Embodiment 3:
a preparation method of hollow mesoporous polydopamine curcumin-loaded nanoparticles is implemented according to the following steps:
step 1, synthesis of HPDA
Adding 0.3 g of dopamine hydrochloride and 0.5 g of Pluronic F127 into a mixed solution of ethanol water (1: 1, v/v), stirring at room temperature, adding 30 mg of silica particles after uniformly stirring, then dropwise adding 0.8 mL of TMB to form a white emulsion, adding 3 mL of ammonia water solution, stirring for 30 min at 40 ℃, centrifuging, ultrasonically washing the precipitate for 5 times by using ethanol and water, then adding the precipitate into 5% hydrofluoric acid water solution for etching, and washing for several times by using deionized water after centrifuging to obtain the hollow mesoporous polydopamine nanoparticles, wherein the hollow mesoporous polydopamine nanoparticles are marked as HPDA.
Adding the mesoporous polydopamine nanoparticles and curcumin powder into anhydrous DMSO according to the mass ratio of 9:1, stirring and reacting for 24 hours at room temperature, centrifuging, washing with a mixed solution of DMSO and deionized water (4: 9, v/v) once and washing with deionized water for 5 times to obtain curcumin-loaded nanoparticles, wherein the label of the curcumin-loaded nanoparticles is HPDA @ CUR;
step 3, synthesis of PEG-CS @ HPDA @ CUR
Weighing 1 g of chitosan and 0.2 g of polyethylene glycol, dissolving in 1% diluted acetic acid solution, uniformly mixing, and stirring at room temperature overnight to obtain polyethylene glycol modified chitosan solution; dissolving the curcumin-loaded nanoparticles 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 hollow mesoporous polydopamine curcumin-loaded nanoparticles PEG-CS @ HPDA @ CUR.
The prepared hollow mesoporous polydopamine curcumin-loaded nanoparticle PEG-CS @ HPDA @ CUR comprises the following components in percentage by mass: 9: 8, the hollow mesoporous polydopamine nanoparticle is used as a carrier, and the curcumin is physically and chemically adsorbed, and the polyethylene glycol modified chitosan is coated on the outermost layer.
The particle size distribution of the hollow mesoporous polydopamine carrier and the hollow mesoporous polydopamine curcumin-loaded nanoparticle in the embodiments 1 to 3 was analyzed by a malvern laser particle sizer. The hollow mesoporous polydopamine carrier and the hollow mesoporous polydopamine curcumin-loaded nanoparticle are dispersed in water, and the particle size distribution is measured, as shown in figure 1, the hydrodynamic diameter sizes are respectively 140 +/-10 nm and 150 +/-10 nm.
The shapes of the hollow mesoporous polydopamine carrier and the hollow mesoporous polydopamine curcumin-loaded nanoparticle in the embodiments 1 to 3 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. 2a, and the prepared HPDA has a narrow particle size distribution range, uniform particle size and an obvious pore structure on the surface. As shown in fig. 2b, it can be seen that the hollow mesoporous polydopamine curcumin-loaded nanoparticle has a uniform particle size and a spherical shape, and the regularly distributed channels become fuzzy due to adsorption of curcumin on the surface and modification of chitosan.
Infrared spectrometry adopts potassium bromide (KBr) tabletting method, and appropriate amount of mesoporous polydopamine carrier, curcumin-loaded nanoparticles and potassium bromide are weighed according to the weight ratio of 1: 50 proportion mixing, and performing infrared scanning in the range of 500-4000 cm < -1 >. As shown in figure 3, peaks (1591, 2918 cm < -1 >) related to chitosan and main peaks (1281, 1510, 2931 cm < -1 >) of curcumin are shown on the FTIR spectrum of the curcumin-loaded nanoparticles. These results confirm that chitosan and curcumin have been bound to mesoporous polydopamine carriers.
HPDA nitrogen adsorption/desorption curve determination: taking an oven-dried 80 mg HPDA sample, instrumentally determining a nitrogen adsorption/desorption curve, as shown in fig. 4, the specific surface area of the prepared HPDA nanoparticles calculated by the BJH method was 48.4940 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. 5, 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.
The release conditions of the hollow mesoporous polydopamine curcumin-loaded nanoparticle in the embodiments 1 to 3 in simulated gastric fluid and simulated intestinal fluid are examined by a dialysis bag method. Placing 1 mL of hollow mesoporous polydopamine curcumin-loaded nanoparticle suspension in 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. 6, and it can be seen from the figure that the drug release rate of the hollow mesoporous polydopamine curcumin-loaded 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 complete. The hollow mesoporous polydopamine curcumin-loaded nanoparticle is slowly released from the beginning of an experiment and is gradually stable along with the lapse of time, so that the hollow mesoporous polydopamine curcumin-loaded nanoparticle has an obvious effect on curcumin controlled release.
The toxic effect of free curcumin, PEG-CS @ HPDA @ CUR on human colon cancer cells HCT-116 was examined by MTT assay. The results are shown in fig. 7, where curcumin showed significant dose-dependent inhibition of human colon cancer cells HCT-116 at two pH conditions. This enhanced anti-tumor effect of curcumin upon carrier loading is likely due to the excellent anti-proliferative activity of chelated curcumin and the synergistic anti-tumor effect of curcumin and the surface-modified chitosan coating.
Embodiment 4:
the embodiment provides a preparation method of hollow mesoporous polydopamine-loaded lycopene nanoparticles PEG-CS @ HPDA @ LYC, which is implemented by the following steps:
step 1, synthesis of HPDA
Adding 0.5 g of dopamine hydrochloride and 1.1 g of Pluronic F127 into a mixed solution of ethanol water (1: 1, v/v), stirring at room temperature, adding 25 mg of silicon dioxide particles after uniformly stirring, and then dropwise adding 0.8 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, adding the precipitate into 4% hydrofluoric acid water solution for etching, centrifuging, and washing by using deionized water for several times to obtain the hollow mesoporous polydopamine nanoparticles marked as HPDA.
Mixing hollow mesoporous polydopamine nanoparticles and lycopene powder according to a mass ratio of 8: 1, stirring and reacting for 24 hours at room temperature, centrifuging, washing with a mixed solution of DMSO and deionized water (4: 7, v/v) once and washing with deionized water for 3 times to obtain lycopene-loaded nanoparticles, which are marked as HPDA @ LYC;
step 3, synthesis of PEG-CS @ HPDA @ LYC
Weighing 1 g of chitosan and 0.2 g of polyethylene glycol, dissolving in 1% diluted acetic acid solution, uniformly mixing, and stirring at room temperature overnight to obtain polyethylene glycol modified chitosan solution; dissolving the lycopene-loaded nanoparticles 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 hollow mesoporous polydopamine-loaded lycopene nanoparticle PEG-CS @ HPDA @ LYC.
The prepared hollow mesoporous polydopamine-loaded lycopene nanoparticle PEG-CS @ HPDA @ LYC comprises the following components in percentage by mass: 9: 8, the hollow mesoporous polydopamine nanoparticle is used as a carrier, and the lycopene is physically and chemically adsorbed by the hollow mesoporous polydopamine nanoparticle, and the polyethylene glycol modified chitosan is coated on the outermost layer.
Embodiment 5:
a preparation method of mesoporous polydopamine-loaded lycopene nanoparticles is implemented according to the following steps:
step 1, synthesis of HPDA
Adding 0.5 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, adding 25 mg of silicon dioxide particles after uniformly stirring, then dropwise adding 1.0 mL of TMB to form a white emulsion, adding 4.0 mL of ammonia water solution, stirring at 50 ℃ for 30 min, centrifuging, ultrasonically washing the precipitate for 5 times by using ethanol and water, adding the precipitate into a 3% hydrofluoric acid aqueous solution for etching, centrifuging, and washing with deionized water for several times to obtain the hollow mesoporous polydopamine nanoparticles, wherein the mark is HPDA.
Mixing hollow mesoporous polydopamine nanoparticles and lycopene powder according to a mass ratio of 8: adding the mixture of 1 into anhydrous DMSO, stirring at room temperature for 12 h, centrifuging, washing with mixed solution of DMSO and deionized water (3: 8, v/v) for one time and with deionized water for 5 times to obtain lycopene-loaded nanoparticles labeled as HPDA @ LYC;
step 3, synthesis of PEG-CS @ HPDA @ LYC
Weighing 1 g of chitosan and 0.25 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 lycopene-loaded nanoparticles 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 hollow mesoporous polydopamine-loaded lycopene nanoparticle PEG-CS @ HPDA @ LYC.
The prepared hollow mesoporous polydopamine-loaded lycopene nanoparticle PEG-CS @ HPDA @ LYC comprises the following components in percentage by mass: 10: 9, the hollow mesoporous polydopamine nanoparticle, the lycopene and the polyethylene glycol modified chitosan are used as carriers, and the lycopene is physically and chemically adsorbed by the hollow mesoporous polydopamine nanoparticle, and the polyethylene glycol modified chitosan is coated on the outermost layer.
Embodiment 6:
a preparation method of hollow mesoporous polydopamine-loaded lycopene nanoparticles is implemented according to the following steps:
step 1, synthesis of HPDA
Adding 0.3 g of dopamine hydrochloride and 1.2 g of Pluronic F127 into a mixed solution of ethanol water (1: 1, v/v), stirring at room temperature, adding 30 mg of silica particles after uniformly stirring, then dropwise adding 1.0 mL of TMB to form a white emulsion, adding 3 mL of ammonia water solution, stirring for 30 min at 40 ℃, centrifuging, ultrasonically washing the precipitate for 5 times by using ethanol and water, then adding the precipitate into 5% hydrofluoric acid water solution for etching, and washing for several times by using deionized water after centrifuging to obtain the hollow mesoporous polydopamine nanoparticles, wherein the label is HPDA.
Adding the mesoporous polydopamine nanoparticles and lycopene powder into anhydrous DMSO according to a mass ratio of 7:1, stirring and reacting for 24 hours at room temperature, centrifuging, washing with a mixed solution of DMSO and deionized water (4: 9, v/v) once and washing with deionized water for 5 times to obtain lycopene-loaded nanoparticles, wherein the lycopene-loaded nanoparticles are marked as HPDA @ LYC;
step 3, synthesis of PEG-CS @ HPDA @ LYC
Weighing 1 g of chitosan and 0.25 g of polyethylene glycol, dissolving in 1% diluted acetic acid solution, uniformly mixing, and stirring at room temperature overnight to obtain polyethylene glycol modified chitosan solution; dissolving the lycopene-loaded nanoparticles 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 hollow mesoporous polydopamine-loaded lycopene nanoparticle PEG-CS @ HPDA @ LYC.
The prepared hollow mesoporous polydopamine-loaded lycopene nanoparticle PEG-CS @ HPDA @ LYC comprises the following components in percentage by mass: 11: 9, the hollow mesoporous polydopamine nanoparticle, the lycopene and the polyethylene glycol modified chitosan are used as carriers, and the lycopene is physically and chemically adsorbed by the hollow mesoporous polydopamine nanoparticle, and the polyethylene glycol modified chitosan is coated on the outermost layer.
The particle size distribution of the hollow mesoporous polydopamine carrier and the hollow mesoporous polydopamine-loaded lycopene nanoparticle in the embodiments 4 to 6 was analyzed by a malvern laser particle sizer. The hollow mesoporous polydopamine carrier and the hollow mesoporous polydopamine-loaded lycopene nanoparticle are dispersed in water, and the particle size distribution is measured, as shown in fig. 8, the hydrodynamic diameter sizes are 140 +/-10 nm and 163 +/-10 nm respectively.
The shapes of the hollow mesoporous polydopamine carrier and the hollow mesoporous polydopamine-loaded lycopene nanoparticle in the embodiments 4 to 6 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. 9a, and the prepared HPDA has a narrow particle size distribution range, uniform particle size and an obvious pore structure on the surface. As shown in fig. 9b, it can be seen that the hollow mesoporous polydopamine-loaded lycopene nanoparticle has a uniform particle size and a spherical shape, and the regularly distributed pores become fuzzy due to the adsorption of lycopene on the surface and the modification of chitosan.
Placing a certain amount of lycopene-loaded nanoparticles and lycopene powder in an indoor scattered light environment, paving, carrying out full light irradiation to enable light energy to be in contact with each surface of lycopene, weighing a certain amount of powder at 0 h, 2 h, 4 h, 6 h, 8 h, 10 h and 12 h respectively at 25 ℃, adding 10 mL of DMSO for full dissolution, carrying out ultrasonic treatment for 10 min, repeating 3 times to obtain an average value, and measuring the content respectively by using an ultraviolet spectrophotometer method. As shown in figure 10, the stability of the lycopene is obviously improved by preparing the nano capsule, and the content of the lycopene is improved to about 97.98 percent from 83.75 percent before original non-adsorption embedding after 12 hours.
The release conditions of the hollow mesoporous polydopamine-loaded lycopene nanoparticles in the embodiments 4 to 6 in simulated gastric fluid and simulated intestinal fluid are examined by a dialysis bag method. Placing 1 mL of hollow mesoporous polydopamine-loaded lycopene nanoparticle suspension in 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. 11, and it can be seen from the figure that the drug release rate of the hollow mesoporous polydopamine-loaded lycopene 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. And the hollow mesoporous polydopamine-loaded lycopene nanoparticle is slowly released from the beginning of the experiment and is gradually stable along with the lapse of time, which shows that the hollow mesoporous polydopamine-loaded lycopene nanoparticle has obvious effect on the controlled release of lycopene.
The toxic effect of free lycopene, PEG-CS @ HPDA @ LYC on human liver cancer cells HepG2 was examined by MTT assay. The results are shown in fig. 12, lycopene shows significant dose-dependent inhibition on human liver cancer cell HepG2 under two pH conditions. This enhanced anti-tumor effect of lycopene upon carrier loading may be due to the excellent anti-proliferative activity of the chelated lycopene and the synergistic anti-tumor effect of lycopene 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 (10)
1. The hollow mesoporous polydopamine-loaded fat-soluble pigment nanoparticle is characterized by comprising the following components in parts by mass of 45-48: 9-14: 6-11 parts of mesoporous polydopamine nanoparticles, a fat-soluble pigment and polyethylene glycol modified chitosan, wherein the mesoporous polydopamine nanoparticles are used as carriers, the fat-soluble pigment is adsorbed by physical and chemical adsorption, and the polyethylene glycol modified chitosan is wrapped on the outermost layer.
2. The hollow mesoporous polydopamine-loaded lipid soluble pigment nanoparticle according to claim 1, wherein the lipid soluble pigment is curcumin or lycopene.
3. A preparation method of hollow mesoporous polydopamine-loaded fat-soluble pigment nanoparticles is characterized by comprising the following steps:
(1) adding dopamine hydrochloride and Pluronic F127 into an ethanol aqueous solution, stirring uniformly at room temperature, adding silica particles, then adding TMB dropwise to form a white emulsion, then adding an ammonia aqueous solution, stirring, centrifuging, ultrasonically washing the precipitate with ethanol and water for several times, then adding the precipitate into a hydrofluoric acid aqueous solution, etching, and centrifuging to obtain hollow mesoporous polydopamine nanoparticles marked as HPDA;
wherein the mass-volume ratio of the dopamine hydrochloride, Pluronic F127, silicon dioxide, TMB and ammonia water solution is 0.3-0.5 g: 1.0-1.2 g: 20-30 mg: 0.6-1.0 mL: 4.0-5.0 mL;
(2) adding the hollow mesoporous polydopamine nanoparticles obtained in the step (1) and fat-soluble pigment powder into anhydrous DMSO, stirring and reacting at room temperature, centrifuging, washing with a mixed solution of DMSO and deionized water and washing with deionized water for several times to obtain fat-soluble pigment-loaded nanoparticles;
the mass ratio of the hollow mesoporous polydopamine nanoparticles to the fat-soluble pigment powder is 5-8: 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 fat-soluble pigment-loaded nanoparticle 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 hollow mesoporous polydopamine fat-soluble pigment-loaded nanoparticle.
4. The method for preparing hollow mesoporous polydopamine-loaded liposoluble pigment nanoparticles according to 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 hollow mesoporous polydopamine-loaded liposoluble pigment nanoparticle as claimed in claim 3, wherein in the step (1), the mass fraction of the hydrofluoric acid aqueous solution is 3-5%.
6. The preparation method of the hollow mesoporous polydopamine-loaded liposoluble pigment nanoparticle as claimed in claim 3, wherein in the step (2), in the mixed solution of DMSO and deionized water, the volume ratio of DMSO to deionized water is 3-4: 7 to 8.
7. The preparation method of the hollow mesoporous polydopamine-loaded liposoluble pigment 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.
8. The preparation method of the hollow mesoporous polydopamine-loaded liposoluble pigment nanoparticle as claimed in claim 7, wherein in the step (3), the mass fraction of the dilute acetic acid aqueous solution is 1-2%.
9. The preparation method of the hollow mesoporous polydopamine-loaded liposoluble pigment nanoparticle as claimed in claim 4, wherein in the step (4), the mass fraction of the acetic acid aqueous solution is 0.5-1%.
10. The preparation method of the hollow mesoporous polydopamine-loaded liposoluble pigment nanoparticle as claimed in any one of claims 3 to 9, 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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Application publication date: 20210326 Assignee: Zibo Hefeng Seed Technology Co.,Ltd. Assignor: HUAIYIN INSTITUTE OF TECHNOLOGY Contract record no.: X2023990000959 Denomination of invention: Hollow mesoporous polydopamine loaded lipid soluble pigment nanoparticles and their preparation method Granted publication date: 20220823 License type: Common License Record date: 20231205 |