CN111991565A - Preparation method of deglutition-promoting peptide modified ferulic acid biodegradable nano-vesicle - Google Patents
Preparation method of deglutition-promoting peptide modified ferulic acid biodegradable nano-vesicle Download PDFInfo
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- A61K47/6915—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a colloid or an emulsion the form being a liposome the form being a liposome with polymerisable or polymerized bilayer-forming substances, e.g. polymersomes
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- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
Abstract
The invention relates to a preparation method of a deglutition-promoting peptide modified ferulic acid biodegradable nano vesicle, which comprises two steps of condensation reaction, finished product preparation and the like. The preparation method is simple in preparation process and high in production and preparation efficiency, the deglutition promoting peptide modified ferulic acid polyethylene glycol-polylactic acid-glycolic acid biodegradable nano vesicle is prepared through a maleamide reaction for the first time, and pharmacodynamic evaluation of porcine parvovirus resistance is carried out in vitro, so that the preparation method of the deglutition promoting peptide modified ferulic acid polyethylene glycol-polylactic acid-glycolic acid biodegradable nano vesicle is established, and the deglutition promoting peptide modified ferulic acid polyethylene glycol-polylactic acid-glycolic acid biodegradable nano vesicle can remarkably improve antiviral and immunity enhancing functions and improve the bioavailability.
Description
Technical Field
The invention relates to a preparation method of a deglutition-promoting peptide modified ferulic acid polyethylene glycol-polylactic acid-glycolic acid biodegradable nano vesicle, belonging to the technical field of medicines.
Background
The research and development of antiviral drugs are a big problem in the field of traditional Chinese veterinary medicine and agriculture at present, and a novel antiviral drug with small drug resistance and remarkable antiviral effect is urgently needed to be developed. The natural product has little toxic and side effect and excellent antiviral effect due to the unique chemical structure, and obtains the attention of most experts and scholars. Most of the existing antiviral drugs in the market are natural products and have a certain antiviral effect, and most of the antiviral drugs have drug resistance and strong hydrophobicity, so that the antiviral drugs from the natural products are extremely easy to resist the drug and have the defects of low bioavailability, large toxic and side effects and the like in clinical application, and therefore, the improvement of the bioavailability of the antiviral drugs becomes an urgent problem to be solved. In recent years, the nano drug delivery system has become the first choice method for solving the bioavailability, and compared with the existing method, the method has the following advantages: 1) the nano drug delivery system has low toxicity and high bioavailability; 2) the nano drug delivery system has uniform particle size and stable property; 3) the nano drug delivery system has proper drug loading and enhanced biological activity; 3) the preparation process is simple and convenient, and the cost is low; 4) the nano-drug has certain targeting positioning, good distribution in vivo and stable release of the nano-particles.
Ferulic Acid (FA) is a phenolic Acid substance widely existing in natural plants, especially has high content in cereal food raw materials such as wheat bran and rice bran, and also has high content in traditional Chinese medicinal materials such as propolis, rhizoma Ligustici Chuanxiong, resina Ferulae, radix Angelicae sinensis, semen Ziziphi Spinosae and cimicifugae rhizoma. It has pharmacological properties of antibiosis, antioxidation, anti-inflammation, radiation resistance, immunoregulation, anti-mutation, cancer prevention and the like, and has become a research hotspot of researchers. The compound has high content in cereal food raw materials, is easy to synthesize and has high yield, and has good clinical application prospect compared with animals. Early researches find that ferulic acid inhibits porcine parvovirus from inducing PK-15 cell apoptosis by eliminating free Radical (ROS) activity, but the clinical application of ferulic acid has certain limitations of drug insolubility, rapid metabolic absorption, short action time, non-centralized action range, large clinical dosage, enhanced side effect and the like. Therefore, how to develop the natural product ferulic acid and improve the bioactivity and bioavailability thereof is a problem to be solved urgently in clinical application.
After viral infection, activation of the endogenous immune response is an important physiological function of self-repair and protection of the body. Spleen-derived factor deglutition promoting peptide (Tuftsin) is an important immune active factor, enhances phagocytosis and chemotaxis of macrophage and neutrophil, promotes drift of Th1/Th2 of an organism, further enhances immune response of the organism, and further plays roles of antivirus, antibiosis and antitumor. The single Tuftsin peptide chain is short, is easy to degrade in a humoral immune process, has poor immunogenicity, and has certain limitations on clinical evaluation and application. Earlier researches find that the Tuftsin series derivatives and the combination with other medicines have wide application prospects.
Therefore, in view of the current situation, a novel method for preparing biodegradable nanovesicles is urgently needed to meet the needs of practical use.
Disclosure of Invention
The invention aims to overcome the defects and provides a preparation method of deglutition-promoting peptide modified ferulic acid polyethylene glycol-polylactic acid-glycolic acid biodegradable nano vesicles, so as to solve the problems of low bioavailability, poor effect and the like in the prior art.
In order to realize the purpose, the invention is realized by the following technical scheme:
a preparation method of a deglutition-promoting peptide modified ferulic acid biodegradable nano vesicle comprises the following steps:
s1, performing condensation reaction, namely connecting PLGA-COOH with NH2-PEG-COOH through acid amine condensation reaction to generate PLGA-PEG-COOH, and adding the deglutition promoting peptide into the PLGA-PEG-COOH to generate PLGA-PEG-Tf;
s2, preparing a finished product, mixing ferulic acid, PLGA-PEG-Tf and chloroform, and stirring to obtain an oil phase; adding the oil phase into the low-concentration PVA solution at a constant speed of 0.01-0.1 m/s for low-temperature ultrasonic treatment, then adding the obtained solution into the high-concentration PVA solution at a constant speed of 0.01-0.1 m/s for uniformly stirring to obtain the stable oil-in-water type multiple emulsion; and (3) carrying out reduced pressure evaporation and low-temperature high-speed centrifugation on the oil-in-water multiple emulsion to collect precipitates, thus obtaining the deglutition-promoting peptide modified ferulic acid polyethylene glycol-polylactic acid-glycolic acid nano vesicle.
Further, in the step S1, the phagocytic peptide reacts with PLGA-PEG-COOH through maleic amide, and the concentration ratio of the phagocytic peptide to the PLGA-PEG-COOH is 1: 15-30.
Further, in the step S2, the concentration of ferulic acid in the oil phase is 2-15 mg/mL.
Further, in the step S2, the concentration of ferulic acid is PLGA-PEG-Tf, and is 10-100 mg/mL.
Further, in the step S2, the concentration of the low-concentration PVA is 0.1% to 0.4%.
Further, in the step S2, the concentration of the high-concentration PVA is 0.5% to 1%.
Further, in the step S2, the proportioning concentration of the oil phase and the PVA is 1: 5-15.
Further, in the step S2, any one of mechanical stirring and ultrasonic stirring is adopted during the stirring operation, the stirring speed is 10-100 rpm, and unidirectional uniform stirring is adopted.
Further, in the step S2, the working pressure at the time of reduced pressure evaporation is 0.01 to 0.05 MPa.
Further, in the step S2, when the centrifugal operation is performed at a low temperature and a high speed, the centrifugal operation temperature is 0 ℃ to 10 ℃, and the centrifugal rotation speed is not lower than 1000 rpm.
The preparation method is simple in preparation process and high in production and preparation efficiency, the deglutition promoting peptide modified ferulic acid polyethylene glycol-polylactic acid-glycolic acid biodegradable nano vesicle is prepared through a maleamide reaction for the first time, and pharmacodynamic evaluation of porcine parvovirus resistance is carried out in vitro, so that the preparation method of the deglutition promoting peptide modified ferulic acid polyethylene glycol-polylactic acid-glycolic acid biodegradable nano vesicle is established, and the deglutition promoting peptide modified ferulic acid polyethylene glycol-polylactic acid-glycolic acid biodegradable nano vesicle can remarkably improve antiviral and immunity enhancing functions and improve the bioavailability.
Drawings
FIG. 1 is a schematic flow diagram of the process of the present invention;
FIG. 2 is an electron microscope image of the swallow-promoting peptide-modified ferulic acid biodegradable nanovesicles prepared by the method;
FIG. 3 is a schematic representation of the effect of the present invention on biological lymphocyte activity;
FIG. 4 is a graph showing the proliferation rate of LPS in cooperation with lymphocytes according to the present invention;
FIG. 5 shows that the deglutition-promoting peptide modified ferulic acid biodegradable nanovesicles of the invention inhibit viral replication and apoptosis.
Detailed Description
Example 1
As shown in fig. 1-3, a method for preparing a deglutition-promoting peptide-modified ferulic acid biodegradable nanovesicle, comprises the following steps:
s1, performing condensation reaction, namely connecting PLGA-COOH with NH2-PEG-COOH through acid amine condensation reaction to generate PLGA-PEG-COOH, and adding the deglutition promoting peptide into the PLGA-PEG-COOH to generate PLGA-PEG-Tf;
s2, preparing a finished product, mixing ferulic acid, PLGA-PEG-Tf and chloroform, and stirring to obtain an oil phase; adding the oil phase into the low-concentration PVA solution at a constant speed of 0.01 m/s for low-temperature ultrasonic treatment, then adding the obtained solution into the high-concentration PVA solution at a constant speed of 0.01 m/s for uniform stirring to obtain a stable oil-in-water type multiple emulsion; and (3) carrying out reduced pressure evaporation and low-temperature high-speed centrifugation on the oil-in-water multiple emulsion to collect precipitates, thus obtaining the deglutition-promoting peptide modified ferulic acid polyethylene glycol-polylactic acid-glycolic acid nano vesicle.
Wherein, the phagocytic peptide and PLGA-PEG-COOH are reacted by maleic amide in the step S1, and the concentration ratio is 1: 15-30.
Meanwhile, in the step S2, the concentration of ferulic acid is 2mg/mL in the oil phase; the ferulic acid concentration is PLGA-PEG-Tf concentration of 10 mg/mL.
In addition, in the step S2, the concentration of the low-concentration PVA is 0.1%; the concentration of the high-concentration PVA is 0.5 percent; the proportioning concentration of the oil phase and the PVA is 1: 5.
Preferably, in the step S2, any one of mechanical stirring and ultrasonic stirring is used during the stirring operation, the stirring speed is 10-100 rpm, and unidirectional uniform stirring is used.
Further, in the step S2, the working pressure at the time of reduced pressure evaporation was 0.01 MPa; when the centrifugal operation is carried out at a low temperature and a high speed, the centrifugal operation temperature is 0 ℃, and the centrifugal rotation speed is 1000 revolutions per minute.
Example 2
As shown in fig. 1-3, a method for preparing a deglutition-promoting peptide-modified ferulic acid biodegradable nanovesicle, comprises the following steps:
s1, performing condensation reaction, namely connecting PLGA-COOH with NH2-PEG-COOH through acid amine condensation reaction to generate PLGA-PEG-COOH, and adding the deglutition promoting peptide into the PLGA-PEG-COOH to generate PLGA-PEG-Tf;
s2, preparing a finished product, mixing ferulic acid, PLGA-PEG-Tf and chloroform, and stirring to obtain an oil phase; adding the oil phase into the low-concentration PVA solution at a constant speed of 0.1 m/s for low-temperature ultrasonic treatment, then adding the obtained solution into the high-concentration PVA solution at a constant speed of 0.1 m/s for uniform stirring to obtain a stable oil-in-water type multiple emulsion; and (3) carrying out reduced pressure evaporation and low-temperature high-speed centrifugation on the oil-in-water multiple emulsion to collect precipitates, thus obtaining the deglutition-promoting peptide modified ferulic acid polyethylene glycol-polylactic acid-glycolic acid nano vesicle.
Wherein, the phagocytic peptide and the PLGA-PEG-COOH are reacted through maleic amide in the step S1, and the concentration ratio of the phagocytic peptide to the PLGA-PEG-COOH is 1: 30.
Meanwhile, in the step S2, the concentration of ferulic acid in the oil phase is 15 mg/mL; the ferulic acid concentration is PLGA-PEG-Tf concentration of 100 mg/mL.
In addition, in the step S2, the concentration of the low-concentration PVA is 0.4%; the concentration of the high-concentration PVA is 1 percent; the proportioning concentration of the oil phase and the PVA is 1: 15.
It is important to point out that in the step S2, mechanical stirring is adopted during the stirring operation, the stirring speed is 100 rpm, and unidirectional uniform stirring is adopted; the working pressure during reduced pressure evaporation is 0.05 MPa; when the low-temperature high-speed centrifugal operation is carried out, the centrifugal operation temperature is 10 ℃, and the centrifugal rotating speed is 2000 r/min.
Example 3
As shown in fig. 1-3, a method for preparing a deglutition-promoting peptide-modified ferulic acid biodegradable nanovesicle, comprises the following steps:
s1, performing condensation reaction, namely connecting PLGA-COOH with NH2-PEG-COOH through acid amine condensation reaction to generate PLGA-PEG-COOH, and adding the deglutition promoting peptide into the PLGA-PEG-COOH to generate PLGA-PEG-Tf;
s2, preparing a finished product, mixing ferulic acid, PLGA-PEG-Tf and chloroform, and stirring to obtain an oil phase; adding the oil phase into the low-concentration PVA solution at a constant speed of 0.05 m/s for low-temperature ultrasonic treatment, then adding the obtained solution into the high-concentration PVA solution at a constant speed of 0.06 m/s for uniform stirring to obtain a stable oil-in-water type multiple emulsion; and (3) carrying out reduced pressure evaporation and low-temperature high-speed centrifugation on the oil-in-water multiple emulsion to collect precipitates, thus obtaining the deglutition-promoting peptide modified ferulic acid polyethylene glycol-polylactic acid-glycolic acid nano vesicle.
Wherein, the phagocytic peptide and the PLGA-PEG-COOH are reacted through maleic amide in the step S1, and the concentration ratio is 1: 20.
Meanwhile, in the step S2, the concentration of ferulic acid in the oil phase is 7 mg/mL; the ferulic acid concentration is that the PLGA-PEG-Tf concentration is 55 mg/mL.
In addition, in the step S2, the concentration of the low-concentration PVA is 0.3%; the concentration of the high-concentration PVA is 0.6 percent; the proportioning concentration of the oil phase and the PVA is 1: 8.
Further, in the step S2, ultrasonic stirring is adopted during stirring operation, the stirring speed is 40 rpm, unidirectional uniform stirring is adopted, and the operating pressure during reduced pressure evaporation is 0.03 MPa; when the centrifugal operation is carried out at low temperature and high speed, the centrifugal operation temperature is 5 ℃, and the centrifugal rotating speed is not 3000 r/min.
Example 4
As shown in fig. 1-3, a method for preparing a deglutition-promoting peptide-modified ferulic acid biodegradable nanovesicle, comprises the following steps:
s1, performing condensation reaction, namely connecting PLGA-COOH with NH2-PEG-COOH through acid amine condensation reaction to generate PLGA-PEG-COOH, and adding the deglutition promoting peptide into the PLGA-PEG-COOH to generate PLGA-PEG-Tf;
s2, preparing a finished product, mixing ferulic acid, PLGA-PEG-Tf and chloroform, and stirring to obtain an oil phase; adding the oil phase into the low-concentration PVA solution at a constant speed of 0.02 m/s for low-temperature ultrasonic treatment, then adding the obtained solution into the high-concentration PVA solution at a constant speed of 0.06 m/s for uniform stirring to obtain a stable oil-in-water type multiple emulsion; and (3) carrying out reduced pressure evaporation and low-temperature high-speed centrifugation on the oil-in-water multiple emulsion to collect precipitates, thus obtaining the deglutition-promoting peptide modified ferulic acid polyethylene glycol-polylactic acid-glycolic acid nano vesicle.
Wherein, the phagocytic peptide and the PLGA-PEG-COOH are reacted through maleic amide in the step S1, and the concentration ratio of the phagocytic peptide to the PLGA-PEG-COOH is 1: 27.
Meanwhile, in the step S2, the concentration of ferulic acid in the oil phase is 9 mg/mL; the ferulic acid concentration is that the PLGA-PEG-Tf concentration is 75 mg/mL.
In addition, in the step S2, the concentration of the low-concentration PVA is 0.2%; the concentration of the high-concentration PVA is 0.8 percent; in addition, the mixing concentration of the oil phase and the PVA is 1: 11.
Further, in the step S2, mechanical stirring is adopted during stirring operation, the stirring speed is 80 rpm, and unidirectional uniform stirring is adopted; the working pressure during reduced pressure evaporation is 0.04 MPa; when the centrifugal operation is carried out at low temperature and high speed, the centrifugal operation temperature is 3 ℃, and the centrifugal rotating speed is not lower than 3500 rpm.
The preparation method is simple in preparation process and high in production and preparation efficiency, the deglutition promoting peptide modified ferulic acid polyethylene glycol-polylactic acid-glycolic acid biodegradable nano vesicle is prepared through a maleamide reaction for the first time, and pharmacodynamic evaluation of porcine parvovirus resistance is carried out in vitro, so that the preparation method of the deglutition promoting peptide modified ferulic acid polyethylene glycol-polylactic acid-glycolic acid biodegradable nano vesicle is established, and the deglutition promoting peptide modified ferulic acid polyethylene glycol-polylactic acid-glycolic acid biodegradable nano vesicle can remarkably improve antiviral and immunity enhancing functions and improve the bioavailability.
The foregoing shows and describes the general principles and broad features of the present invention and advantages thereof. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are described in the specification and illustrated only to illustrate the principle of the present invention, but that various changes and modifications may be made therein without departing from the spirit and scope of the present invention, which fall within the scope of the invention as claimed. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (10)
1. A preparation method of a deglutition-promoting peptide modified ferulic acid biodegradable nano vesicle is characterized by comprising the following steps: the preparation method of the deglutition-promoting peptide modified ferulic acid biodegradable nano vesicle comprises the following steps:
s1, performing condensation reaction, namely connecting PLGA-COOH and NH2-PEG-COOH through acid amine condensation reaction to generate PLGA-PEG-COOH, and adding tuftsin (Tf) into the PLGA-PEG-COOH to generate PLGA-PEG-Tf;
s2, preparing a finished product, mixing ferulic acid, PLGA-PEG-Tf and chloroform, and stirring to obtain an oil phase; adding the oil phase into the low-concentration PVA solution at a constant speed of 0.01-0.1 m/s for low-temperature ultrasonic treatment, then adding the obtained solution into the high-concentration PVA solution at a constant speed of 0.01-0.1 m/s for uniformly stirring to obtain the stable oil-in-water type multiple emulsion; and (3) carrying out reduced pressure evaporation and low-temperature high-speed centrifugation on the oil-in-water multiple emulsion to collect precipitates, thus obtaining the deglutition-promoting peptide modified ferulic acid polyethylene glycol-polylactic acid-glycolic acid nano vesicle.
2. The method for preparing the deglutition-promoting peptide modified ferulic acid biodegradable nanovesicles according to claim 1, wherein the method comprises the following steps: in the step S1, the phagocytic peptide reacts with PLGA-PEG-COOH through maleic amide, and the concentration ratio of the phagocytic peptide to the PLGA-PEG-COOH is 1: 15-30.
3. The method for preparing the deglutition-promoting peptide modified ferulic acid biodegradable nanovesicles according to claim 1, wherein the method comprises the following steps: in the step S2, the concentration of ferulic acid in the oil phase is 2-15 mg/mL.
4. The method for preparing the deglutition-promoting peptide modified ferulic acid biodegradable nanovesicles according to claim 1, wherein the method comprises the following steps: in the step S2, the ferulic acid concentration is PLGA-PEG-Tf concentration of 10-100 mg/mL in the oil phase.
5. The method for preparing the deglutition-promoting peptide modified ferulic acid biodegradable nanovesicles according to claim 1, wherein the method comprises the following steps: in the step S2, the concentration of the low-concentration PVA is 0.1% -0.4%.
6. The method for preparing the deglutition-promoting peptide modified ferulic acid biodegradable nanovesicles according to claim 1, wherein the method comprises the following steps: in the step S2, the concentration of the high-concentration PVA is 0.5-1%.
7. The method for preparing the deglutition-promoting peptide modified ferulic acid biodegradable nanovesicles according to claim 1, wherein the method comprises the following steps: in the step S2, the proportioning concentration of the oil phase and the PVA is 1: 5-15.
8. The method for preparing the deglutition-promoting peptide modified ferulic acid biodegradable nanovesicles according to claim 1, wherein the method comprises the following steps: in the step S2, any one of mechanical stirring and ultrasonic stirring is used during the stirring operation, the stirring speed is 10-100 rpm, and unidirectional uniform stirring is used.
9. The method for preparing the deglutition-promoting peptide modified ferulic acid biodegradable nanovesicles according to claim 1, wherein the method comprises the following steps: in the step S2, the working pressure at the time of reduced pressure evaporation is 0.01 to 0.05 MPa.
10. The method for preparing the deglutition-promoting peptide modified ferulic acid biodegradable nanovesicles according to claim 1, wherein the method comprises the following steps: in the step S2, when the centrifugal operation is carried out at low temperature and high speed, the centrifugal operation temperature is 0-10 ℃, and the centrifugal rotation speed is not lower than 1000 revolutions per minute.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115463096A (en) * | 2022-08-19 | 2022-12-13 | 安徽中龙神力生物科技有限公司 | Cephalosporin synergistic sustained-release preparation and preparation method thereof |
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