CN113546072A - Baicalein nanometer preparation and its preparing method and use - Google Patents
Baicalein nanometer preparation and its preparing method and use Download PDFInfo
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- CN113546072A CN113546072A CN202110786349.2A CN202110786349A CN113546072A CN 113546072 A CN113546072 A CN 113546072A CN 202110786349 A CN202110786349 A CN 202110786349A CN 113546072 A CN113546072 A CN 113546072A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/40—Cyclodextrins; Derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/08—Solutions
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
Abstract
The invention discloses a baicalein nanometer preparation which is prepared by loading baicalein on a chitosan-cyclodextrin graft polymer. The invention also discloses a preparation method of the baicalein nanometer preparation, which comprises the following steps: 1) preparing baicalein standard solution with anhydrous ethanol; 2) preparing a chitosan-cyclodextrin graft polymer solution; 3) adding the baicalein standard solution prepared in the step 1) into the chitosan-cyclodextrin graft polymer solution, stirring, performing rotary evaporation to remove ethanol, performing ultrasonic treatment by using an ultrasonic cell disruption instrument, centrifuging, and taking a supernatant to obtain the baicalein nanometer preparation. The invention also discloses application of the prepared baicalein nanometer preparation for eliminating staphylococcus aureus biofilm. The baicalein nanometer preparation prepared by the invention has the characteristics of being capable of destroying the biofilm structure, enhancing the permeability of the drug biofilm, improving the killing capacity of the drug to the tunica mucosa bacteria and the like.
Description
Technical Field
The invention belongs to the field of traditional Chinese medicine preparations. More specifically, the invention relates to a baicalein nanometer preparation, a preparation method and an application thereof.
Background
Staphylococcus aureus (Staphylococcus aureus), a non-motile, coagulase-positive, scleroderma, is a Gram-positive bacterium. Staphylococcus aureus infections often exhibit different clinical symptoms depending on the infected population and location. Staphylococcus aureus is mostly used as a conditioned pathogen, coexists with human skin flora and nasal mucosa flora, and is clinically manifested as inflammation such as pyogenic myositis and necrotizing pneumonia in about 40% of infected patients in hospitals. At present, the scholars at home and abroad think that the staphylococcus aureus has great pathogenicity and stress resistance because the staphylococcus aureus forms a biofilm in vivo and in vitro, and the biofilm provides a protective life style for the staphylococcus aureus, so that the drug resistance and the persistent infectivity of bacteria are increased.
Bacterial Biofilms (BBF) refer to structural colonies in the form of cells encapsulated by proteoglycan protein polymers, lipoproteins, fibrin, etc. formed by bacteria themselves, which are shaped like a membrane and can be irreversibly attached to a solid support, and the formation of Bacterial Biofilms enhances the resistance of bacteria to various factors, and can cause many persistent and chronic Bacterial infections. The staphylococcus aureus infected diseases have the phenomena of repeated infection and difficult healing, and the main reason is that staphylococcus aureus easily forms a biofilm, and after the biofilm is formed by bacteria, the bacteria have strong resistance to antibiotics and host immunity and can present clinical symptoms of chronic infection.
Common s.aureus infections were identified as effective treatments, however once biofilm formation, treatment difficulties were dramatically increased. Infection by staphylococcus aureus biofilms was reported to account for 56% of U.S. medical device infections between 2006-2007. In recent years, with the development of medical technology, indwelling medical devices have become an essential component of modern medical care, and these implanted medical devices, such as implanted artificial heart valves, catheters, joint prostheses, etc., will become important colonization sites for bacterial biofilms. Therefore, research and development of a medicinal preparation capable of effectively eliminating bacterial biofilm have important significance for clinical treatment of the biofilm diseases.
At present, antibiotics are the first choice for treating diseases caused by staphylococcus aureus infection, but the excessive use of antibiotics easily causes great dependence and toxicity to human bodies, so that the treatment of related infectious diseases by using traditional Chinese medicine antibacterial agents becomes a hot topic in the scientific research community at present. Scutellaria baicalensis Georgi (Scutellaria baicalensis Georgi) is a dried root of perennial herb of Scutellaria of Labiatae, and has effects of clearing heat, eliminating dampness, clearing heat-fire, clearing heat-toxin, stopping bleeding, and preventing miscarriage. Modern researches show that the scutellaria has good treatment effect on infectious diseases, such as urinary tract infection and respiratory tract infection, the main effective components of the scutellaria are flavonoid compounds, such as baicalin, baicalein, wogonin and the like, and the scutellaria has strong antibacterial and antiviral effects. Research of Vijing and the like shows that baicalein has certain in vitro antibacterial and in vivo anti-inflammatory effects; the research of billows and the like shows that baicalein has the bacteriostatic effect; researches on ginger tea and the like show that baicalein has a remarkable antiviral effect; studies such as Zhang Chunhui etc. show that baicalein has antibacterial activity to staphylococcus aureus and Escherichia coli. Therefore, the baicalein has obvious antibacterial effect and various drug effects and is widely applied to diseases caused by bacterial infection. However, baicalein has the characteristics of strong hydrophobicity and high lipophilicity, so that the baicalein has the problems of low drug solubility, unsatisfactory treatment effect and the like. Therefore, the water solubility of the baicalein is improved, the treatment effect of the medicine is enhanced, and the medicine has important significance for the clinical application of the medicine.
Disclosure of Invention
An object of the present invention is to solve at least the above problems and to provide at least the advantages described later.
It is still another object of the present invention to provide a baicalein nano-formulation which is capable of disrupting biofilm structure, enhancing drug biofilm permeability and improving bacterial drug uptake capacity.
To achieve these objects and other advantages in accordance with the present invention, there is provided a baicalein nano-formulation prepared by loading baicalein on a chitosan-cyclodextrin graft polymer.
Preferably, the baicalein nanometer preparation has an average particle size of 420-440 nm and a Zeta potential of 40-50 mV.
The preparation method of the baicalein nanometer preparation comprises the following steps:
1) preparing baicalein standard solution with anhydrous ethanol;
2) preparing a chitosan-cyclodextrin graft polymer solution;
3) adding the baicalein standard solution prepared in the step 1) into the chitosan-cyclodextrin graft polymer solution, stirring, performing rotary evaporation to remove ethanol, performing ultrasonic treatment by using an ultrasonic cell disruption instrument, centrifuging, and taking a supernatant to obtain the baicalein nanometer preparation.
Preferably, the concentration of the baicalein standard solution is 1-5 mg/mL.
Preferably, the chitosan-cyclodextrin graft polymer is weighed and dissolved in glacial acetic acid with the volume fraction of 2% to prepare a chitosan-cyclodextrin graft polymer solution with the concentration of 5-10 mg/mL.
Preferably, in the step 3), the ultrasonic cell disruptor is used for ultrasonic treatment for 10-20 min.
Preferably, in step 3), centrifugation is carried out at 4000-.
The baicalein nanometer preparation is applied to eliminating staphylococcus aureus biofilm.
The invention at least comprises the following beneficial effects:
firstly, the baicalein nanometer preparation can obviously improve the killing effect of the medicine on bacteria in the staphylococcus aureus biofilm and enhance the effect of the medicine on eliminating the staphylococcus aureus biofilm.
Secondly, the invention takes Chitosan-cyclodextrin grafted polymer (CD-CS) as a carrier, baicalein is prepared by ultrasonic preparation of a medicine through a probe, the solubility of the medicine is increased, CS-CD is utilized to influence the permeability of cell walls, the structure of the biofilm is damaged, and the permeability of the medicine biofilm is enhanced to improve the medicine intake capability of bacteria.
Additional advantages, objects, and features of the invention will be set forth in part in the description which follows and in part will become apparent to those having ordinary skill in the art upon examination of the following or may be learned from practice of the invention.
Drawings
FIG. 1 is a particle size distribution diagram of the baicalein nano-preparation prepared by the present invention;
FIG. 2 is a diagram showing the potential distribution of the baicalein nano-preparation prepared by the present invention;
FIG. 3 is a diagram showing the elimination of Staphylococcus aureus biofilm by baicalein nano-preparations prepared according to the present invention;
FIG. 4 is a graph of the different incubation times of baicalein nano-preparations and bacteria prepared by the invention on the removal of Staphylococcus aureus biofilm;
FIG. 5 is a diagram illustrating a colony counting method for examining the killing of the nano-preparation of baicalein against tunica capsularis;
FIG. 6 is a diagram illustrating how baicalein nano-preparations kill tunica mucosa bacteria by laser confocal method.
Detailed Description
The present invention is further described in detail below with reference to the attached drawings so that those skilled in the art can implement the invention by referring to the description text.
It will be understood that terms such as "having," "including," and "comprising," as used herein, do not preclude the presence or addition of one or more other elements or groups thereof.
Example 1
A method for preparing baicalein nanometer preparation comprises the following steps:
1) weighing baicalein, putting into a 10mL volumetric flask, and adding absolute ethanol to a constant volume to prepare a 2mg/mL baicalein standard solution;
2) weighing 30mg of a carrier material chitosan-cyclodextrin graft polymer (CS-CD), placing the carrier material CS-CD in a beaker, adding 5mL of 2% glacial acetic acid, and stirring and dissolving the mixture on a constant-temperature stirrer at room temperature to obtain a chitosan-cyclodextrin graft polymer solution;
3) slowly dripping 2mg/mL baicalein solution into the chitosan-cyclodextrin graft polymer solution, and continuously stirring for 5 hours at room temperature; removing ethanol by rotary evaporation, and fixing the volume to 5mL by using pure water; performing ultrasonic treatment with ultrasonic cell disruptor probe for 15min (2 s ultrasonic/2 s intermittent), centrifuging the solution with low speed centrifuge at 4000r/min for 10min, and collecting the supernatant to obtain baicalein nanometer preparation.
Example 2
A method for preparing baicalein nanometer preparation comprises the following steps:
1) weighing baicalein, putting into a 10mL volumetric flask, and adding absolute ethanol to a constant volume to prepare a 1mg/mL baicalein standard solution;
2) weighing 25mg of a carrier material chitosan-cyclodextrin graft polymer (CS-CD), placing the carrier material chitosan-cyclodextrin graft polymer (CS-CD) in a beaker, adding 5mL of 2% glacial acetic acid, and stirring and dissolving the mixture on a constant-temperature stirrer at room temperature to obtain a chitosan-cyclodextrin graft polymer solution;
3) slowly dripping 1mg/mL baicalein solution into the chitosan-cyclodextrin graft polymer solution, and continuously stirring for 5 hours at room temperature; removing ethanol by rotary evaporation, and fixing the volume to 5mL by using pure water; performing ultrasonic treatment with ultrasonic cell disruptor probe for 10min (2 s ultrasonic/2 s intermittent), centrifuging the solution with low speed centrifuge at 5000r/min for 5min, and collecting the supernatant to obtain baicalein nanometer preparation.
Example 3
A method for preparing baicalein nanometer preparation comprises the following steps:
1) weighing baicalein, putting into a 10mL volumetric flask, and adding absolute ethanol to a constant volume to prepare a 5mg/mL baicalein standard solution;
2) weighing 50mg of a carrier material chitosan-cyclodextrin graft polymer (CS-CD), placing the carrier material CS-CD in a beaker, adding 5mL of 2% glacial acetic acid, and stirring and dissolving the mixture on a constant-temperature stirrer at room temperature to obtain a chitosan-cyclodextrin graft polymer solution;
3) slowly dripping 5mg/mL baicalein solution into the chitosan-cyclodextrin graft polymer solution, and continuously stirring for 5 hours at room temperature; removing ethanol by rotary evaporation, and fixing the volume to 5mL by using pure water; performing ultrasonic treatment with ultrasonic cell disruptor probe for 20min (2 s ultrasonic/2 s intermittent), centrifuging the solution with low speed centrifuge at 4500r/min for 20min, and collecting the supernatant to obtain baicalein nanometer preparation.
Example 4
The synthesis of the chitosan-cyclodextrin graft polymer used in examples 1-3 comprises the following steps:
a) adding 2.5g of cyclodextrin into 6.5mL of dimethyl sulfoxide, dissolving 3.75g of p-methylbenzenesulfonyl chloride into 6mL of dimethyl sulfoxide, dropwise adding the solution into the cyclodextrin solution, stirring the solution for 24 hours at the temperature of 45 ℃, adding 30mL of acetone, crystallizing the solution to release a white precipitate, filtering the solution, and washing the solution with precooled acetone to obtain mono-6-deoxy-6- (p-toluenesulfonyl) -beta-cyclodextrin (6-OTs-beta-CD);
b)0.25g of chitosan (the molar mass is 150KD, and the deacetylation degree is more than 90%) is dissolved in 1% by volume of acetic acid solution, the 6-OTs-beta-CD prepared in the step a) is added, the mixture is stirred for 48 hours at the temperature of 45 ℃, and then the mixture is dialyzed for 7 days in deionized water and is frozen and dried to obtain the chitosan-cyclodextrin graft polymer.
Testing particle size and potential measurements of a baicalein Nanodiulation
The particle size and the potential of 1mL of the baicalein nanometer preparation prepared in the example 1 are measured in a Malvern particle size and potential sample cell, and the result shows that the average particle size of the baicalein nanometer preparation is 420-440 nm, and the Zeta potential is 40-50 mV. The particle size distribution of baicalein nanometer preparation is shown in figure 1, and the potential diagram is shown in figure 2.
Testing the influence of two baicalein nanometer preparations with different concentrations on the elimination condition of biological capsule
Selecting single staphylococcus aureus colony, inoculating the single staphylococcus aureus colony in a TSB liquid culture medium, incubating at a constant temperature of 37 ℃, and diluting the bacterial liquid in the logarithmic phase to 1x106cfu/mL, adding 100 mu L of diluted bacterial liquid into each hole of a 96 sterile microporous plate, and culturing for 24h at constant temperature; the bacterial solution was aspirated, 100. mu.L of the baicalein nanopreparation prepared in example 1 at 10-fold minimum inhibitory concentration (MIC, concentration of 12.5. mu.g/mL), 6-fold MIC, 4-fold MIC and 2-fold MIC was added to the well, incubation was carried out at a constant temperature of 37 ℃ for 12 hours, OD was measured at 595nm by a crystal violet staining method using a microplate reader, and the ability of the baicalein nanopreparation at different concentrations to eliminate Staphylococcus aureus biofilms was examined, the results being shown in FIG. 3. The baicalein nanometer preparation has significant difference compared with baicalein solution group and negative control group, and the baicalein nanometer preparation significantly improves the elimination effect of the medicine on staphylococcus aureus biofilm
Experiment shows the influence of three different incubation times on the elimination of the biofilm by the baicalein nanometer preparation
Selecting Staphylococcus aureus, inoculating into TSB liquid culture medium, incubating at 37 deg.C, and diluting the bacteria liquid of logarithmic phase to 1x106cfu/mL, adding 100 mu L of diluted bacterial liquid into each hole of a 96 sterile microporous plate, and culturing for 24h at constant temperature; the bacterial solution was aspirated, 100 μ L of baicalein nanopreparation (prepared in example 1) with 6 times MIC concentration was added to the wells, incubation was carried out at constant temperature of 37 ℃ for 3h, 6h, and 12h, OD at 595nm was determined by crystal violet staining, and the ability of different incubation times to eliminate staphylococcus aureus biofilm in baicalein nanopreparation was determined, the results are shown in fig. 4. Compared with a blank bacterial solution, the baicalein nanometer preparation has an obvious effect of eliminating a staphylococcus aureus biofilm within 3 hours, has an obvious effect compared with a baicalein solution group, and has a tiny change of the eliminating effect along with the prolonging of the acting time.
Test four colony counting method for investigating the inhibiting condition of baicalein nano preparation on biological tunica capsulata
Selecting single staphylococcus aureus colony, inoculating the single staphylococcus aureus colony in a TSB liquid culture medium, incubating at a constant temperature of 37 ℃, and diluting the bacterial liquid in the logarithmic phase to 1x106cfu/mL, dilute the bacterial liquid to 1x106cfu/mL, adding 100 mu L of diluted bacterial liquid into each hole of a 96 sterile microporous plate, and incubating for 24h at constant temperature; the bacterial solution was aspirated, baicalein nanopreparation (75 μ g/mL) (prepared in example 1) was added, incubation was performed at constant temperature for 3h, and a bulk drug control group and a negative control group were set simultaneously. Removing the solution, adding a certain volume of sterile normal saline, carefully scraping the biofilm, filling into a 5mL volumetric flask, fixing the volume with the sterile normal saline, transferring into an EP tube, and performing ultrasonic treatment for 1.5min by using an ultrasonic disruptor in a sterile environment. Diluting the ultrasonic bacterial suspension with sterile physiological saline by equivalent incremental method, and diluting the preparation group, baicalein control group and bacterial liquid control group by 104、106、108And (4) doubling. Pouring 3mL of the diluted bacterial suspension into 45mL of meat extract protein agar culture medium which is melted and cooled to 45 ℃, uniformly rotating and uniformly shaking, quickly pouring into a plate, sealing a sealing film after cooling and solidification, culturing for 24h at constant temperature, counting the number of colonies of each group of reagents by naked eyes, and calculating the result as shown in FIG. 5. The colony number of the blank bacteria liquid group is far higher than that of the preparation group and the raw material medicine group; the colony number between the baicalein nanometer preparation and the baicalein solution group is relatively reduced by 55 times; the colony number of the baicalein nanometer preparation group and the baicalein solution group have significant differences (P is less than 0.01) compared with the blank bacterial liquid group.
Test five Live & Dead kit for observing penetration and sterilization of preparation to biological capsule
Selecting single staphylococcus aureus colony, inoculating the single staphylococcus aureus colony in a TSB liquid culture medium, incubating at a constant temperature of 37 ℃, and diluting the bacterial liquid in the logarithmic phase to 1x106cfu/mL, adding 500 mu L of diluted bacterial liquid into a sterile glass culture dish, and culturing for 24h at constant temperature; the bacterial solution was aspirated, 500. mu.L of baicalein nanopreparation (prepared in example 1) (75. mu.g/mL) was added, incubation was performed at constant temperature for 3h, and a bulk drug control group was set. The solution was removed, rinsed 3 times with purified water, and 500. mu.L of the diluted staining solution was added to a sterile environment in a dark placeIn a glass-bottom culture dish, tinfoil is wrapped, after incubation for 15min in the dark, the lethal condition of the baicalein nano-preparation on staphylococcus aureus is observed by using an LSCM (laser confocal scanning microscope), and the result is shown in fig. 6. 6-a is a baicalein raw material drug comparison group, 6-b is a baicalein nano preparation group, the lethality of the raw material drug comparison group is only 8.77%, the lethality of the baicalein nano preparation group is as high as 66.55%, and the lethal effect of the baicalein nano preparation group on tunica capsularis in the staphylococcus aureus biofilm is obviously stronger than that of the baicalein solution group of the raw material drug.
While embodiments of the invention have been described above, it is not limited to the applications set forth in the description and the embodiments, which are fully applicable in various fields of endeavor to which the invention pertains, and further modifications may readily be made by those skilled in the art, it being understood that the invention is not limited to the details shown and described herein without departing from the general concept defined by the appended claims and their equivalents.
Claims (8)
1. The baicalein nanometer preparation is characterized in that the baicalein nanometer preparation is prepared by loading baicalein on a chitosan-cyclodextrin graft polymer.
2. The baicalein nano-preparation according to claim 1, wherein the average particle diameter of the baicalein nano-preparation is 420 to 440nm, and the Zeta potential is 40 to 50 mV.
3. The method for preparing a baicalein nano-formulation as claimed in claim 1 or 2, comprising the steps of:
1) preparing baicalein standard solution with anhydrous ethanol;
2) preparing a chitosan-cyclodextrin graft polymer solution;
3) adding the baicalein standard solution prepared in the step 1) into the chitosan-cyclodextrin graft polymer solution, stirring, performing rotary evaporation to remove ethanol, performing ultrasonic treatment by using an ultrasonic cell disruption instrument, centrifuging, and taking a supernatant to obtain the baicalein nanometer preparation.
4. The method for preparing a baicalein nano-formulation according to claim 3, wherein the concentration of the baicalein standard solution is 1-5 mg/mL.
5. The method for preparing baicalein nanometer preparation according to claim 3, wherein the chitosan-cyclodextrin graft polymer is weighed and dissolved in glacial acetic acid with a volume fraction of 2% to prepare a chitosan-cyclodextrin graft polymer solution with a concentration of 5-10 mg/mL.
6. The method for preparing a baicalein nano-formulation according to claim 3, wherein in the step 3), the ultrasonic treatment is performed for 10-20min by using an ultrasonic cell disruptor.
7. The method for preparing baicalein nano-preparation according to claim 3, wherein in step 3), centrifugation is carried out at 4000-.
8. Use of the nano-formulation of baicalein according to any one of claims 1-2 or 4-7 for the elimination of staphylococcus aureus biofilms.
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Application publication date: 20211026 |