CN116211839A - Curcumin drug-loading system and preparation method thereof - Google Patents
Curcumin drug-loading system and preparation method thereof Download PDFInfo
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Abstract
The embodiment of the invention discloses a curcumin drug-loading system and a preparation method thereof. The curcumin drug-carrying system takes a nanoscale two-dimensional-cyclodextrin-metal organic framework as a drug carrier. Compared with 3D-CD-MOF, the curcumin drug-loading system has higher drug-loading capacity and higher solubility and dissolution, can realize rapid release and dissolution of curcumin in water, improves the solubility and bioavailability of curcumin in vivo, ensures the safety and effectiveness of clinical drug application, and has great social and economic significance.
Description
Technical Field
The embodiment of the invention relates to the technical field of nano medicines, in particular to a curcumin drug delivery system and a preparation method thereof.
Background
Curcumin (Curcumin) is a natural compound, is a diketone compound extracted from rhizome of some plants in Zingiberaceae and Araceae, is a rare pigment with diketone structure in plant kingdom, and has chemical formula of C 21 H 20 O 6 . With the increasing depth of research on curcumin, it has been found that curcumin has wide pharmacological activities such as anti-inflammatory, antioxidant, lipid regulating, antiviral, anti-infective, anti-tumor, anticoagulative, anti-hepatic fibrosis, anti-atherosclerosis and the like, and has little adverse reaction. Curcumin is currently one of the most popular natural food colors in the world, and is a food additive approved for use by the world health organization and the U.S. food and drug administration, and by multiple countries. It is not only curcumin as a non-steroidal anti-inflammatory drug that attracts researchers, but because of its chemopreventive properties, curcumin has a broad preventive property against diseases. In view of the fact that the modern medical research discovers that the occurrence of a plurality of diseases of human bodies is related to the participation of free radical formation and inflammatory reaction, the antioxidant activity and the anti-inflammatory effect of curcumin have attracted extensive attention of domestic and foreign scholars. Removal ofIn addition, curcumin has great prospect in clinical practice, has definite beneficial effects on several human diseases, has no side effect and is nontoxic to patients. Thus, the compound curcumin is an excellent candidate for the treatment of certain diseases, which largely supports the research and development of curcumin as a prophylactic and disease modifying agent.
However, the characteristic of curcumin having a wide range of pharmacological actions also causes problems of insufficient drug delivery and bioavailability, malabsorption, rapid metabolism and rapid systemic clearance are the most important factors causing low levels of curcumin in blood plasma and tissues, which are major obstacles to the effectiveness thereof, and prevent the use thereof in medicine. Thus, it is a challenging task to find a suitable drug delivery system to utilize curcumin, a natural product, as an effective treatment for a specific disease.
Metal-organic frameworks (MOFs) are periodic porous materials composed of organic bridging ligands and metal connection points, and have the characteristics of wide size and pore size distribution range, controllable structure, large porosity and specific surface area, multiple functions and the like. Most of the metal-organic frameworks are currently synthesized from organic regenerative molecules and transition metal ions, the potential toxicity and non-degradability of which limit their use in the food field. Cyclodextrin (CD) is a class of cyclic pastes produced by the enzymatic hydrolysis of amylose by cyclodextrin glucosyltransferase. The synthesis method of the CD-MOFs is simple and mild, the raw materials are food-grade, the products have no toxic reagent residues, and the CD-MOFs are green and edible metal-organic frameworks. The CD-MOFs have rich pore structures, provide sufficient space for drug entrapment, and have wide application prospects in drug delivery.
Disclosure of Invention
Therefore, the embodiment of the invention provides a curcumin drug-loading system and a preparation method thereof, which aim to solve the defect of low bioavailability of curcumin in practical application.
In order to achieve the above object, the embodiment of the present invention provides the following technical solutions:
according to a first aspect of the embodiments of the present invention, the embodiments of the present invention provide a curcumin drug delivery system, which uses a nanoscale two-dimensional-cyclodextrin-metal organic framework as a drug carrier, and the preparation method of the nanoscale two-dimensional-cyclodextrin-metal organic framework includes:
adding potassium carbonate and gamma-cyclodextrin into deionized water, ultrasonically vibrating, stirring at 65-75deg.C for 10-20min, making the solution light yellow, passing through 0.8um filter membrane while it is hot, rapidly placing the obtained filtrate into 2-5deg.C water bath, stirring, slowly dripping acetone while stirring, slowly appearing white flaky crystal, stirring again after stirring, centrifuging to collect precipitate, washing with anhydrous alcohol, and drying.
Further, the molar ratio of the potassium carbonate to the gamma-cyclodextrin is 1:6-10; the mass volume ratio of the gamma-cyclodextrin to the deionized water is 1:35-45; the volume ratio of the addition amount of the acetone to the filtrate is 1-2:10.
Further, the rotation speed of the first stirring is 400-600rpm min -1 The time is 10-20min; the rotation speed of the second stirring is 3500-4500rpm min -1 The time is 5-15min.
Further, the preparation method of the nanoscale two-dimensional-cyclodextrin-metal organic framework further comprises the following steps:
dispersing the dried solid in ethanol solution of glacial acetic acid, centrifuging, collecting precipitate, washing with absolute ethanol, and drying.
Further, the preparation method of the ethanol solution of glacial acetic acid comprises the following steps: dissolving 1-5mL of glacial acetic acid in 50mL of absolute ethanol; the mass volume ratio of the solid to the ethanol solution of glacial acetic acid is 1:15-20.
According to a second aspect of the embodiments of the present invention, there is provided a method for preparing a curcumin delivery system as defined in any one of the above, comprising:
ultrasonically dissolving curcumin in absolute ethyl alcohol to obtain curcumin solution;
and adding a drug carrier into the curcumin solution for inclusion, centrifuging, pouring out supernatant, washing with absolute ethyl alcohol, and freeze-drying to obtain the curcumin drug carrying system.
Further, the concentration of the curcumin solution is 1.0-4.0 mg.mL -1 。
Further, the molar ratio of the curcumin to the drug carrier is 0.5-2.
Further, the inclusion time is 1-4h.
The embodiment of the invention has the following advantages:
compared with 3D-MOF, the curcumin drug-loading system has higher drug-loading capacity and higher solubility and dissolution, can realize rapid release and dissolution of curcumin in water, improves the solubility and bioavailability of curcumin in vivo, ensures the safety and effectiveness of clinical drug application, and has great social and economic significance.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below. It will be apparent to those of ordinary skill in the art that the drawings in the following description are exemplary only and that other implementations can be obtained from the extensions of the drawings provided without inventive effort.
FIG. 1 is an SEM micrograph of a 2D-CD-MOF according to an embodiment of the present invention;
FIG. 2 is an SEM micrograph of a 3D-CD-MOF according to an embodiment of the present invention;
FIG. 3 is an AFM image of a 2D-CD-MOF provided by an embodiment of the present invention;
FIG. 4 is a FTIR spectrum of Cur, cur/γ -CD, cur/2D-CD-MOF and Cur/3D-CD-MOF provided by an embodiment of the present invention;
FIG. 5 is a graph showing Cur1mg.ml at different concentrations -1 (A)、2.0mg·ml -1 (B) And 3.0 mg.ml -1 (C) Next, 4.0 mg/ml -1 (D) The amount of gamma-CD, 2D-CD-MOF and 3D-CD-MOF loading Cur, the effect of immersion time on gamma-CD, 2D-CD-MOF and 3D-CD-MOF loadings (E);
FIG. 6 is a graph showing comparison of the dissolution rates of Cur/gamma-CD, cur/2D-CD-MOF and Cur/3D-CD-MOF provided by the embodiment of the invention.
Detailed Description
Other advantages and advantages of the present invention will become apparent to those skilled in the art from the following detailed description, which, by way of illustration, is to be read in connection with certain specific embodiments, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
EXAMPLE 1 preparation of pharmaceutical Carriers
(1) Synthesis of nanoscale two-dimensional-cyclodextrin-metal organic frameworks (2D-CD-MOFs)
0.4300g of potassium carbonate and 1.0200g of gamma-cyclodextrin (molar ratio 1:8) are dissolved in 40mL of deionized water, and after 30min of ultrasound, the solution is placed in a 70 ℃ water bath for reaction for 15min, and the solution is light yellow. After completion of the reaction, the mixture was filtered through a 0.8 μm filter while hot, and the filtrate was then rapidly transferred to a conical flask, and stirred with a magnetic stirrer (500 rpm min in a water bath at 3 ℃ C.) -1 ) Stirring for 15min, slowly dripping 8mL of acetone into the conical flask during stirring, and stirring at 4000rpm min -1 Centrifuging at a rotating speed of (1) for 10min, pouring out supernatant, collecting flaky crystals, preparing an acidified ethanol solution by glacial acetic acid and absolute ethanol according to a volume ratio of 1:25, dispersing the obtained flaky crystals in the acidified ethanol solution, centrifuging, washing 3 times by absolute ethanol, and drying in a vacuum drying oven at 50 ℃ for 2h to obtain the 2D-CD-MOF of white neutral powder.
(2) Synthesis of nanoscale three-dimensional-cyclodextrin-metal organic frameworks (3D-CD-MOFs)
Adding 1.6200g of gamma-cyclodextrin and 8mol equivalent of 0.5600g of potassium hydroxide into 50mL of deionized water, dissolving by ultrasonic treatment for 30min, filtering by a 0.45um filter membrane, collecting filtrate in a 100mL beaker, adding 5mL of methanol, placing the beaker containing the mixed solution in a sealed container containing a large amount of methanolAnd putting the container into a preheated water bath kettle with the temperature of 50 ℃ to start steam diffusion. After vapor diffusion for 6-8 h, at this time, a small amount of white solid is precipitated (mainly micron-sized 3D-CD-MOF), the micron-sized 3D-CD-MOF is removed by filtration while hot, the obtained filtrate (vapor diffusion solution) is transferred to another beaker, and 50mL of the filtrate (vapor diffusion solution) is added dropwise at a concentration of 8 mg.mL -1 Cetyl trimethylammonium bromide (CTAB) in methanol; incubating the obtained mixed solution in a constant temperature incubator at 37 ℃ for overnight, centrifuging to collect precipitate, thoroughly washing the precipitate with isopropanol (i-PrOH) for three times to enable CTAB attached to 3D-CD-MOF to be separated more thoroughly, preparing acidified ethanol solution by glacial acetic acid and absolute ethanol according to a volume ratio of 1:25, dispersing the obtained solid phase in the acidified ethanol solution, centrifuging, washing with absolute ethanol for 3 times, and drying in a vacuum drying oven at 50 ℃ for 2 hours to obtain white neutral powder 3D-CD-MOF.
Test example 1
Characterization of 2D-CD-MOF and 3D-CD-MOF
1. PH value
The pH values of the 2D-CD-MOF and 3D-CD-MOF of example 1 were measured using a pH meter, and the results showed that: the pH of both the 2D-CD-MOF and 3D-CD-MOF was around 7.0.
2. Scanning Electron Microscope (SEM)
SEM observations of 2D-CD-MOF and 3D-CD-MOF of example 1 were made.
The method comprises the following steps: dissolving a small amount of 2D-CD-MOF sample powder in acetone, performing ultrasonic dispersion for 10min, and then dripping the dispersed solution on a silicon wafer; the 3D-CD-MOF is dispersed in absolute ethyl alcohol by the same method, then is dripped on a silicon wafer, the dripped silicon wafer is fixed on a metal stub, and a thin gold film is coated before observation under proper magnification. On the basis of the SEM image obtained, a size measurement was performed.
As shown in fig. 1 and 2, sem results show successful synthesis of nanoscale 3D-CD-MOFs, with an average size of about 500 nm; the synthesis of the flaky 2D-CD-MOF is successful, and the average width is about 1 um.
2. Atomic Force Microscope (AFM)
A small amount of 2D-CD-MOF sample was taken, dispersed with acetone, and then was added dropwise to a silicon wafer, the thickness thereof was measured by AFM, and the AFM image was processed by nanoscopeenalysis, as shown in FIG. 3, and the result showed that the average thickness of 2D-CD-MOF was 1.82nm, reaching the nanoscale level.
Test example 2 optimization of the method for preparing curcumin delivery System
Different curcumin drug-carrying systems (Cur/gamma-CD inclusion compound, cur/2D-CD-MOF inclusion compound and Cur/3D-CD-MOF inclusion compound) are prepared by adopting an immersion method. And the optimal drug loading conditions are selected from three factors: concentration of curcumin solution, molar ratio of curcumin to drug carrier (γ -CD, 2D-CD-MOF and 3D-CD-MOF), and different inclusion times.
The method comprises the following steps: dissolving curcumin into absolute ethyl alcohol by ultrasonic, and respectively preparing four concentrations of curcumin solutions, wherein the four concentrations are respectively as follows: 1.0, 2.0, 3.0, 4.0 mg.multidot.mL -1 The molar ratio of curcumin to gamma-CD, 3D-CD-MOF and 2D-CD-MOF was 2:1, 1:1 and 1:2, respectively, and the inclusion time of stirring with a 500rpm magnetic stirrer was 1, 2, 3 and 4 hours, respectively, at room temperature. Centrifuging the clathrate under different conditions at high rotation speed (the centrifugal rotation speed is 12000rpm, the centrifugal temperature is 15 ℃, and the centrifugal time is 15 min), pouring out supernatant to obtain Cur/gamma-CD precipitate, cur/2D-CD-MOF precipitate and Cur/3D-CD-MOF precipitate under different drug carrying conditions, washing the precipitate with absolute ethyl alcohol at least twice, and removing curcumin which is not included on the surface and is positioned in gamma-CD, 2D-CD-MOF and 3D-CD-MOF cavities; and drying for 4 hours by using a freeze dryer under negative pressure to obtain Cur/gamma-CD inclusion compound, cur/2D-CD-MOF inclusion compound and Cur/3D-CD-MOF inclusion compound under different drug loading conditions.
1. Synchrotron radiation Fourier transform infrared Spectrometry (SR-FTIR)
The measurement results of the infrared spectrum (SR-FTIR) are shown in FIG. 4. The spectral patterns of Cur/gamma-CD inclusion compounds, cur/2D-CD-MOF inclusion compounds and Cur/3D-CD-MOF inclusion compounds contained peak segments similar and close to those of curcumin, which indicated that Cur was successfully loaded on gamma-CD, 2D-CD-MOF and 3D-CD-MOF.
2. Inclusion compound content
The results of drug loading for different drug loading concentrations, different inclusion times, different molar ratios, and different drug carriers are shown in figure 5. The best drug loading results were found to show that: the concentration of the curcumin solution is 3mg/ml, the inclusion time is 3h, the molar ratio of gamma-CD, 3D-CD-MOF and 2D-CD-MOF to Cur is 1:2, the optimal drug loading condition is adopted, and the highest drug loading rates are 4.74%, 10.03% and 11.27% respectively.
The results show that: the concentration of the curcumin solution, the inclusion time and the material ratio can influence the content of the curcumin in the inclusion compound, the concentration is too low, the reaction time is too short, the material cannot fully include the curcumin, but the concentration is too high, the reaction time is too long, and the material can wrap more curcumin, but the drug loading rate cannot be improved; moreover, the experimental result shows that the synthesized nano-scale sheet material 2D-CD-MOF is more than curcumin included by the raw materials gamma-CD and the three-dimensional 3D-CD-MOF, the shape of the material has a certain influence on the drug loading result, the sheet material has higher drug loading rate than the three-dimensional material, and the 2D-CD-MOFs are more suitable as carriers of curcumin than the raw materials gamma-CD and 3D-CD-MOFs in the aspect of drug loading.
3. Cur and determination of solubility of a series of inclusion compounds
Respectively dissolving excessive Cur and related inclusion compound thereof in 20ml of water at room temperature, continuously stirring for 72h, and measuring the solubility of Cur to be 1.05+/-0.02 ug/ml under the external of a ultraviolet spectrophotometer; the solubility of Cur in Cur/gamma-CD, cur/3D-CD-MOF and Cur/2D-CD-MOF is 0.43+/-0.05 mg/mL, 1.24+/-0.10 mg/mL and 1.56+/-0.06 mg/mL. From the results, it was found that inclusion of Cur in 2D-CD-MOF or 3D-CD-MOF, respectively, can increase the solubility of Cur, and the solubility of Cur/2D-CD-MOF is more excellent than inclusion in gamma-CD.
4. Cur and determination of dissolution of a series of inclusion compounds
The Cur, cur/γ -CD, cur/3D-CD-MOF and Cur/2D-CD-MOF inclusion compounds were put into a dissolution tester to which PBS having pH=7.4 had been added at room temperature, and were sampled at a rotation speed of 100rpm for dissolution measurement at 3min,5min,10min,15min,20min,30min,45min and 60min, respectively.
The results show that: the Cur is almost free from dissolution in 60min, the result of the dissolution rate of a series of inclusion compounds of the Cur is shown in figure 6, the dissolution rates of the Cur can be improved to different degrees by the 2D-CD-MOF, the 3D-CD-MOF and the gamma-CD, the quick release effect of the 2D-CD-MOF is more obvious, and the dissolution rate in 3min can reach 88.45%.
Conclusion:
1. the 2D-CD-MOF is an ultrathin two-dimensional novel nanoscale material, has high porosity, high specific surface area, high solubility and rich active sites, is nontoxic and edible, can be applied to a curcumin carrier, and improves the indissolvable property of curcumin.
2. The drug carrying systems Cur/gamma-CD, cur/2D-CD-MOF and Cur/3D-CD-MOF are prepared by adopting an immersion method, and the optimal drug carrying conditions are screened out by optimizing the concentration of Cur solution, the molar ratio of Cur to gamma-CD, 2D-CD-MOF and 3D-CD-MOF and inclusion time. The results show that: the inclusion time is 3h, and the drug loading concentration is highest when the molar ratio of the 2D-CD-MOF to the Cur is 1:2. The result shows that the inclusion time is too long, and the result of drug loading of the material cannot be improved due to too high curcumin concentration. Moreover, the drug loading rate of the Cur/2D-CD-MOF is higher than that of the Cur/3D-CD-MOF and Cur/gamma-CD, which proves that the flaky 2D-CD-MOF can improve the bioavailability of insoluble drugs more than the stereoscopic 3D-CD-MOF.
3. Compared with Cur/3D-CD-MOF and Cur/gamma-CD, the Cur/2D-CD-MOF has faster dissolution rate and higher solubility, which indicates that the flaky 2D-CD-MOF can improve the bioavailability of insoluble drugs more than the stereoscopic 3D-CD-MOF.
4. The invention successfully prepares the CD-MOFs raw material, successfully improves the solubility of curcumin in water by constructing a nano-scale two-dimensional CD-MOF drug-carrying system, and simultaneously proves that 2D-CD-MOF has larger advantages than 3D-CD-MOF, and the result shows that the shape of the material has a certain influence on the physical properties of the carried drugs.
While the invention has been described in detail in the foregoing general description and specific examples, it will be apparent to those skilled in the art that modifications and improvements can be made thereto. Accordingly, such modifications or improvements may be made without departing from the spirit of the invention and are intended to be within the scope of the invention as claimed.
Claims (9)
1. The curcumin drug-carrying system is characterized in that a nanoscale two-dimensional-cyclodextrin-metal organic framework is used as a drug carrier, and the preparation method of the nanoscale two-dimensional-cyclodextrin-metal organic framework is as follows:
adding potassium carbonate and gamma-cyclodextrin into deionized water, ultrasonically vibrating, stirring at 65-75deg.C for 10-20min, making the solution light yellow, passing through 0.8um filter membrane while it is hot, rapidly placing the obtained filtrate into 2-5deg.C water bath, stirring, slowly dripping acetone while stirring, slowly appearing white flaky crystal, stirring again after stirring, centrifuging to collect precipitate, washing with anhydrous alcohol, and drying.
2. The curcumin delivery system according to claim 1, wherein,
the molar ratio of the potassium carbonate to the gamma-cyclodextrin is 1:6-10;
the mass volume ratio of the gamma-cyclodextrin to the deionized water is 1:35-45;
the volume ratio of the addition amount of the acetone to the filtrate is 1-2:10.
3. The curcumin delivery system according to claim 1, wherein,
the rotation speed of the first stirring is 400-600rpm min -1 The time is 10-20min;
the rotation speed of the second stirring is 3500-4500rpm min -1 The time is 5-15min.
4. The curcumin delivery system according to claim 1, wherein the preparation method of the nanoscale two-dimensional-cyclodextrin-metal organic framework further comprises:
dispersing the dried solid in ethanol solution of glacial acetic acid, centrifuging, collecting precipitate, washing with absolute ethanol, and drying.
5. The curcumin delivery system according to claim 4, wherein,
the preparation method of the ethanol solution of glacial acetic acid comprises the following steps: dissolving 1-5mL of glacial acetic acid in 50mL of absolute ethanol; the mass volume ratio of the solid to the ethanol solution of glacial acetic acid is 1:15-20.
6. A method of preparing a curcumin delivery system according to any one of claims 1-5, comprising:
ultrasonically dissolving curcumin in absolute ethyl alcohol to obtain curcumin solution;
and adding a drug carrier into the curcumin solution for inclusion, centrifuging, pouring out supernatant, washing with absolute ethyl alcohol, and freeze-drying to obtain the curcumin drug carrying system.
7. The method for preparing a curcumin delivery system according to claim 6, wherein,
the concentration of the curcumin solution is 1.0-4.0mg.mL -1 。
8. The method for preparing a curcumin delivery system according to claim 6, wherein,
the molar ratio of the curcumin to the drug carrier is 0.5-2.
9. The method for preparing a curcumin delivery system according to claim 6, wherein,
the inclusion time is 1-4h.
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