CN112137988A - Preparation method of polylactic acid-glycolic acid copolymer-cisplatin/ginsenoside Rg3 double-drug-loading sustained-release anticancer drug - Google Patents
Preparation method of polylactic acid-glycolic acid copolymer-cisplatin/ginsenoside Rg3 double-drug-loading sustained-release anticancer drug Download PDFInfo
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Abstract
The invention discloses a preparation method of a polylactic acid-glycolic acid copolymer-cisplatin/ginsenoside Rg3 double-drug-loading slow-release anticancer drug. The novel anticancer drug with high stability, biocompatibility and good slow release effect is obtained by taking polylactic acid-glycolic acid copolymer as a substrate material and simultaneously wrapping cisplatin and 20(R) -ginsenoside Rg3 into nanoparticles in a physical coating mode. The preparation method of the polylactic acid-glycolic acid copolymer-cisplatin/ginsenoside Rg3 double-drug-loading sustained-release anticancer drug provided by the invention has the advantages that the polylactic acid-glycolic acid copolymer is used as a substrate material, and then cisplatin and 20(R) -ginsenoside Rg3 are simultaneously wrapped by a physical coating means, so that the sustained-release anticancer drug with high stability and biocompatibility is obtained, the preparation process is simple, the cost is low, and the particle size is uniform.
Description
Technical Field
The invention relates to a preparation method of a double-drug-loading slow-release anticancer drug, in particular to a preparation method of a polylactic acid-glycolic acid copolymer-cis-platinum/ginsenoside Rg3 double-drug-loading slow-release anticancer drug.
Technical Field
Cancer has become a major disease affecting human health, with increasing morbidity and mortality from year to year. Currently, cancer treatment modalities include surgery, chemotherapy, radiotherapy, photodynamic therapy, and the like. Chemotherapy is one of the most common approaches in cancer treatment, and the treatment method mainly refers to acting on cancer cells through small molecule drugs, generating cytotoxicity on the cancer cells and causing apoptosis. The chemotherapy drugs can inhibit the growth of cancer cells to a certain extent, but the drugs have the defects of poor water solubility, low biological membrane permeability, lack of molecular targeting property and the like, which brings great toxic and side effects to patients. Therefore, it is important to construct an ideal drug delivery system. If the functionalized high molecular polymer is modified on the anticancer drug with low water solubility, the water solubility and the molecular targeting performance of the polymer can be greatly enhanced, and the sustained release effect can be achieved to enhance the treatment effect. Although medical delivery systems have gained wide acceptance in medical research, most studies have been directed to establishing delivery systems for individual drugs. In order to solve the problems, a feasible scheme is formed by establishing a high-molecular double-drug combined carrier, and the novel multiple-drug combined delivery system not only solves the problems of single property, low water solubility, poor biocompatibility and the like of the drug, but also can play the effects of slow release and targeted delivery.
The traditional chemotherapy drugs comprise cisplatin, ginsenoside, adriamycin, camptothecin and the like. Among them, cisplatin, which is a derivative of inorganic platinum, is widely used in the treatment of various cancers, such as bladder cancer, ovarian cancer, lung cancer, testicular cancer, etc. In the clinical application at the present stage, the cisplatin drug has certain limitation on the curative effect due to some defects of the cisplatin drug, such as low water solubility, low target binding rate, obvious nephrotoxicity, generation of drug-resistant tumor cells and the like. Ginsenoside is an important member in the field of traditional Chinese medicine as an extract of ginseng, and has complex and extensive effects on multiple systems and organs of a human body. A large amount of pharmacological experimental data show that the ginsenoside has obvious anti-tumor effect. Taking 20(R) -ginsenoside Rg3 as an example, it can play an anti-tumor role by inhibiting tumor growth, invasion and metastasis, inducing apoptosis, inhibiting proliferation, inhibiting angiogenesis and other mechanisms.
In recent years, various drug carrier systems have emerged to better treat cancer. For example: liposomes, polymeric micelles, nanogels, dendrimers, and the like. Among all drug delivery carriers, polylactic-co-glycolic acid (PLGA) has passed FDA certification due to its characteristics of high stability, biodegradability, easy chemical modification, short in vivo blood circulation time, etc., and has formally been included in the united states pharmacopeia as a pharmaceutical adjuvant.
Disclosure of Invention
The invention provides a preparation method of a polylactic acid-glycolic acid copolymer-cis-platinum/ginsenoside Rg3 double-drug-loading slow-release anticancer drug, and a novel anticancer drug with high stability, biocompatibility and good slow-release effect is obtained.
The invention is realized by the following technical scheme:
the invention discloses a preparation method of a polylactic acid-glycolic acid copolymer-cis-platinum/ginsenoside Rg3 double-drug-loading slow-release anticancer drug, which takes the polylactic acid-glycolic acid copolymer as a base material, and the cis-platinum and 20(R) -ginsenoside Rg3 are simultaneously wrapped into nanoparticles in a physical coating mode to obtain the novel anticancer drug with high stability, biocompatibility and good slow-release effect.
As a further improvement, the preparation method of the polylactic acid-glycolic acid copolymer-cisplatin/ginsenoside Rg3 double-drug-loading slow-release anticancer drug comprises the following specific preparation steps:
1) dissolving the polylactic acid-glycolic acid copolymer in an organic solvent by adopting a method of 'similar and compatible' to prepare 50-100mg/mL polylactic acid-glycolic acid copolymer solution;
2) respectively dissolving cisplatin and 20(R) -ginsenoside Rg3 in a solvent to prepare a 5-10mg/mL medicinal solution;
3) mixing the medicine solution with the polylactic acid-glycolic acid copolymer solution by adopting a physical coating method, ultrasonically mixing the medicine solution and the polylactic acid-glycolic acid copolymer solution for 1 to 5 minutes by using a cell crusher, and then adding the medicine solution into a proper amount of polyvinyl alcohol aqueous solution for ultrasonic emulsification for 1 to 5 minutes to obtain a mixed solution 1;
4) adding an isopropanol aqueous solution with the same amount as the polyvinyl alcohol aqueous solution into the mixed solution 1, and performing ultrasonic or stirring demulsification for 1-5 minutes to obtain a mixed solution 2;
5) stirring the obtained mixed solution 2 for 3-5 hours in a dark place to obtain suspension 3 containing fine particles;
6) and centrifuging, washing and freeze-drying the suspension 3 to obtain the polylactic acid-glycolic acid copolymer-cis-platinum/20 (R) -ginsenoside Rg3 double-drug-loading sustained-release anticancer drug.
As a further improvement, in the step 1) of the invention, the ratio of the polylactic acid-glycolic acid copolymer is 50:50, 75:25 or 80: 20.
As a further improvement, the organic solvent is N, N-dimethylformamide, dichloromethane or tetrahydrofuran.
As a further improvement, in the step 2) of the invention, the solvent is a 0.9% sodium chloride aqueous solution and dichloromethane by mass fraction, or dimethyl sulfoxide and alcohols.
As a further improvement, the step 4) of the invention adopts a demulsifier for demulsification, and the demulsifier is 2% isopropanol water solution or acetone.
As a further improvement, in the step 6) of the invention, the freeze drying needs a protective agent, and the protective agent is mannitol or glucose or poloxamer 188.
The invention has the following advantages:
1. the preparation method of the polylactic acid-glycolic acid copolymer-cisplatin/ginsenoside Rg3 double-drug-loading sustained-release anticancer drug provided by the invention has the advantages that the polylactic acid-glycolic acid copolymer is used as a substrate material, and then cisplatin and 20(R) -ginsenoside Rg3 are simultaneously wrapped by a physical coating means, so that the sustained-release anticancer drug with high stability and biocompatibility is obtained, the preparation process is simple, the cost is low, and the particle size is uniform.
2. Compared with the non-encapsulated cisplatin and 20(R) -ginsenoside Rg3, the prepared medicine has obvious slow release effect.
3. The preparation method of the double-drug-loading slow-release anticancer drug provided by the invention can also be suitable for the preparation of three or more different drugs, and meets the requirements of multiple drug combination treatment in clinical medicine.
4. The preparation method of the polylactic acid-glycolic acid copolymer-cisplatin/ginsenoside Rg3 double-drug-loading sustained-release anticancer drug solves the problems that cisplatin causes nephrotoxicity and other side effects on a human body, and 20(R) -ginsenoside Rg3 is not directionally distributed and the like.
5. The preparation method of the polylactic acid-glycolic acid copolymer-cisplatin/ginsenoside Rg3 double-drug-loading slow-release anticancer drug provided by the invention is based on the surface modification easiness and stability of the polylactic acid-glycolic acid copolymer, and the polylactic acid-glycolic acid copolymer-cisplatin/20 (R) -ginsenoside Rg3 double-drug-loading slow-release anticancer drug can be further prepared into a slow-release drug with a specific targeting function.
Drawings
FIG. 1 is a chromatogram of cisplatin and 20(R) -ginsenoside Rg 3;
FIG. 2 is the in vitro cumulative release profile of cisplatin (a) and 20(R) -ginsenoside Rg3 (b).
Detailed Description
The invention discloses a preparation method of a polylactic acid-glycolic acid copolymer-cis-platinum/ginsenoside Rg3 double-drug-loading slow-release anticancer drug, which takes the polylactic acid-glycolic acid copolymer as a base material, and the cis-platinum and 20(R) -ginsenoside Rg3 are simultaneously wrapped into nanoparticles in a physical coating mode to obtain the novel anticancer drug with high stability, biocompatibility and good slow-release effect. A preparation method of polylactic acid-glycolic acid copolymer-cisplatin/ginsenoside Rg3 double-drug-loading slow-release anticancer drugs comprises the following specific preparation steps:
1) dissolving the polylactic acid-glycolic acid copolymer in an organic solvent by adopting a method of 'similar and compatible' to prepare 50-100mg/mL polylactic acid-glycolic acid copolymer solution; the polylactic acid-glycolic acid copolymer is 50:50, 75:25 or 80: 20; the organic solvent is N, N-dimethylformamide, dichloromethane or tetrahydrofuran.
2) Respectively dissolving cisplatin and 20(R) -ginsenoside Rg3 in a solvent to prepare a 5-10mg/mL medicinal solution; the solvent is 0.9 percent of sodium chloride aqueous solution and dichloromethane by mass fraction, or dimethyl sulfoxide and alcohols.
3) Mixing the medicine solution with the polylactic acid-glycolic acid copolymer solution by adopting a physical coating method, ultrasonically mixing the medicine solution and the polylactic acid-glycolic acid copolymer solution for 1 to 5 minutes by using a cell crusher, and then adding the medicine solution into a proper amount of polyvinyl alcohol aqueous solution for ultrasonic emulsification for 1 to 5 minutes to obtain a mixed solution 1;
4) adding an isopropanol aqueous solution with the same amount as the polyvinyl alcohol aqueous solution into the mixed solution 1, and performing ultrasonic or stirring demulsification for 1-5 minutes to obtain a mixed solution 2; the demulsifier is a 2% isopropanol aqueous solution or acetone.
5) Stirring the obtained mixed solution 2 for 3-5 hours in a dark place to obtain suspension 3 containing fine particles;
6) and centrifuging, washing and freeze-drying the suspension 3 to obtain the polylactic acid-glycolic acid copolymer-cis-platinum/20 (R) -ginsenoside Rg3 double-drug-loading sustained-release anticancer drug. Lyophilization requires a protectant which is mannitol or glucose or poloxamer 188.
Example 1
The preparation process of the polylactic acid-glycolic acid copolymer-cisplatin/20 (R) -ginsenoside Rg3 double-drug-loading slow-release anticancer drug comprises the following steps:
dissolving 50mg of polylactic acid-glycolic acid copolymer (50:50) in 1mLN, N-dimethylformamide to obtain polylactic acid-glycolic acid copolymer solution; respectively dissolving 5mg of cisplatin and 20(R) -ginsenoside Rg3 in 1 mL0.9% sodium chloride aqueous solution and dichloromethane to obtain medicinal solutions; mixing the polylactic acid-glycolic acid copolymer solution with the medicine solution, then dropwise adding the mixture into 15mL of 1% polyvinyl alcohol aqueous solution, and then carrying out ultrasonic emulsification for 3 minutes to obtain a mixed solution 1; 15mL of 2% isopropanol aqueous solution is dropwise added into the mixed solution 1, and ultrasonic demulsification is carried out for 5 minutes to obtain a mixed solution 2; stirring the mixed solution at room temperature for 3 hours until the mixed solution is solidified into balls to obtain a suspension 3; after centrifugation, washing and freeze drying, the polylactic acid-glycolic acid copolymer-cisplatin/20 (R) -ginsenoside Rg3 nanoparticles are obtained.
Example 2
And (3) chromatographic separation:
cisplatin:
the instrument comprises the following steps: high performance liquid chromatography (Ultimate 3000, Thermo Fisher Scientific), UV detector, Welch welchrom C18 chromatography column
Mobile phase: methanol-water (70:30, V: V)
Detection wavelength: 254nm
Column temperature: 30 deg.C
Flow rate: 1mL/min
Sample introduction amount: 20 μ L
Pre-column derivatization:
1) 0.5g of sodium diethyldithiocarbamate is dissolved in 0.1mol/L NaOH solution to prepare a sodium diethyldithiocarbamate solution with the mass fraction of 5% (fresh preparation is needed each time).
2) 500. mu.L of cisplatin solution of known concentration and 50. mu.L of 5% sodium diethyldithiocarbamate solution were mixed in a water bath at 37 ℃ for 30min in the absence of light.
20(R) -ginsenoside Rg 3:
the instrument comprises the following steps: high performance liquid chromatography (Ultimate 3000, Thermo Fisher Scientific), UV detector, Welch welchrom C18 chromatography column
Mobile phase: acetonitrile-water (45:55, V: V)
Detection wavelength: 203nm
Column temperature: 30 deg.C
Flow rate: 1mL/min
Sample introduction amount: 20 μ L
FIG. 1 shows the chromatograms of cisplatin and 20(R) -ginsenoside Rg3, with detection signals appearing at 16.52 minutes and 21.37 minutes, respectively.
Example 3
And (3) testing the slow release effect:
accurately weighing 10mg of cisplatin, 20(R) -ginsenoside Rg3 and polylactic acid-glycolic acid copolymer-cisplatin/20 (R) -ginsenoside Rg3 nanoparticles, dispersing in corresponding solvents, taking out a certain amount of solution at intervals under a dark condition, and replacing fresh and equivalent solvents. Performing pre-column derivatization and direct sample injection according to the method, and calculating the release amount of cisplatin and 20(R) -ginsenoside Rg 3. As shown in figure 2, compared with cisplatin and 20(R) -ginsenoside Rg3 directly dispersed in a solvent, the sustained-release effect of the nanoparticles coated with the polylactic acid-glycolic acid copolymer is obvious. At 48h and 24h, the release amounts of cisplatin and 20(R) -ginsenoside Rg3 respectively reach peak 85.07% and peak 78.18%, and the good slow release performance of the slow release microsphere is embodied.
The embodiments described above are intended to facilitate one of ordinary skill in the art in understanding and using the present invention. The present invention is not limited to the embodiments described herein, and those skilled in the art should, in light of the present disclosure, make modifications and alterations to the present invention without departing from the scope of the present invention.
Claims (7)
1. A preparation method of a polylactic acid-glycolic acid copolymer-cis-platinum/ginsenoside Rg3 double-drug-loading slow-release anticancer drug comprises the steps of taking the polylactic acid-glycolic acid copolymer as a substrate material, and simultaneously wrapping cis-platinum and 20(R) -ginsenoside Rg3 into nanoparticles in a physical coating mode to obtain the novel anticancer drug with high stability, biocompatibility and good slow-release effect.
2. The preparation method of polylactic acid-glycolic acid copolymer-cisplatin/ginsenoside Rg3 double drug-loaded slow-release anticancer drug according to claim 1, which comprises the following specific preparation steps:
1) dissolving the polylactic acid-glycolic acid copolymer in an organic solvent by adopting a method of 'similar and compatible' to prepare 50-100mg/mL polylactic acid-glycolic acid copolymer solution;
2) respectively dissolving cisplatin and 20(R) -ginsenoside Rg3 in a solvent to prepare a 5-10mg/mL medicinal solution;
3) mixing the medicine solution with the polylactic acid-glycolic acid copolymer solution by adopting a physical coating method, ultrasonically mixing the medicine solution and the polylactic acid-glycolic acid copolymer solution for 1 to 5 minutes by using a cell crusher, and then adding the medicine solution into a proper amount of polyvinyl alcohol aqueous solution for ultrasonic emulsification for 1 to 5 minutes to obtain a mixed solution 1;
4) adding an isopropanol aqueous solution with the same amount as the polyvinyl alcohol aqueous solution into the mixed solution 1, and performing ultrasonic or stirring demulsification for 1-5 minutes to obtain a mixed solution 2;
5) stirring the obtained mixed solution 2 for 3-5 hours in a dark place to obtain suspension 3 containing fine particles;
6) and centrifuging, washing and freeze-drying the suspension 3 to obtain the polylactic acid-glycolic acid copolymer-cis-platinum/20 (R) -ginsenoside Rg3 double-drug-loading sustained-release anticancer drug.
3. The preparation method of the polylactic acid-glycolic acid copolymer-cisplatin/ginsenoside Rg3 double drug-loaded slow-release anticancer drug according to claim 2, wherein in the step 1), the polylactic acid-glycolic acid copolymer is 50:50, 75:25 or 80: 20.
4. The preparation method of the polylactic acid-glycolic acid copolymer-cisplatin/ginsenoside Rg3 double drug-loaded slow-release anticancer drug according to claim 2, wherein the organic solvent is N, N-dimethylformamide, dichloromethane or tetrahydrofuran.
5. The preparation method of polylactic acid-glycolic acid copolymer-cisplatin/ginsenoside Rg3 double drug-loaded sustained-release anticancer drug according to claim 2, wherein in the step 2), the solvent is 0.9% by mass of sodium chloride aqueous solution and dichloromethane, or dimethyl sulfoxide and alcohol.
6. The method for preparing the polylactic acid-glycolic acid copolymer-cisplatin/ginsenoside Rg3 double drug-loaded sustained-release anticancer drug according to claim 2, 3, 4 or 5, characterized in that a demulsifier is adopted in the step 4), and the demulsifier is 2% isopropanol water solution or acetone.
7. The preparation method of the polylactic acid-glycolic acid copolymer-cisplatin/ginsenoside Rg3 double drug-loaded slow-release anticancer drug according to claim 6, wherein in the step 6), the freeze drying needs a protective agent, and the protective agent is mannitol or glucose or poloxamer 188.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114632072A (en) * | 2022-04-07 | 2022-06-17 | 陕西巨子生物技术有限公司 | Preparation and application of ginsenoside Rg5 lipid nanoparticle sustained release preparation |
| CN115948494A (en) * | 2022-09-12 | 2023-04-11 | 昆明理工大学 | Method for synthesizing oleanane type saponin by using panax notoginseng cells |
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| CN101732345A (en) * | 2008-11-20 | 2010-06-16 | 中国人民解放军第二军医大学 | Cisplatin spinal tumor slow-release implant and preparation method thereof |
| CN106361724A (en) * | 2015-07-24 | 2017-02-01 | 富力 | 20(R)-ginsenoside Rg3 slow release nanometer microsphere composition, and preparation method thereof |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101732345A (en) * | 2008-11-20 | 2010-06-16 | 中国人民解放军第二军医大学 | Cisplatin spinal tumor slow-release implant and preparation method thereof |
| CN106361724A (en) * | 2015-07-24 | 2017-02-01 | 富力 | 20(R)-ginsenoside Rg3 slow release nanometer microsphere composition, and preparation method thereof |
Non-Patent Citations (1)
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| CN114632072A (en) * | 2022-04-07 | 2022-06-17 | 陕西巨子生物技术有限公司 | Preparation and application of ginsenoside Rg5 lipid nanoparticle sustained release preparation |
| CN114632072B (en) * | 2022-04-07 | 2023-08-18 | 陕西巨子生物技术有限公司 | Preparation and application of ginsenoside Rg5 lipid nanoparticle sustained release preparation |
| CN115948494A (en) * | 2022-09-12 | 2023-04-11 | 昆明理工大学 | Method for synthesizing oleanane type saponin by using panax notoginseng cells |
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Application publication date: 20201229 |