CN114869843B - Preparation method of high-crosslinking euglena polysaccharide gel - Google Patents
Preparation method of high-crosslinking euglena polysaccharide gel Download PDFInfo
- Publication number
- CN114869843B CN114869843B CN202210559443.9A CN202210559443A CN114869843B CN 114869843 B CN114869843 B CN 114869843B CN 202210559443 A CN202210559443 A CN 202210559443A CN 114869843 B CN114869843 B CN 114869843B
- Authority
- CN
- China
- Prior art keywords
- euglena polysaccharide
- gel
- euglena
- crosslinking
- polysaccharide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 150000004676 glycans Chemical class 0.000 title claims abstract description 129
- 241000195620 Euglena Species 0.000 title claims abstract description 126
- 229920001282 polysaccharide Polymers 0.000 title claims abstract description 126
- 239000005017 polysaccharide Substances 0.000 title claims abstract description 126
- 238000004132 cross linking Methods 0.000 title claims abstract description 64
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 239000003513 alkali Substances 0.000 claims abstract description 68
- 238000000034 method Methods 0.000 claims abstract description 33
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000001263 FEMA 3042 Substances 0.000 claims abstract description 32
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 claims abstract description 32
- 229920002258 tannic acid Polymers 0.000 claims abstract description 32
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 claims abstract description 32
- 229940033123 tannic acid Drugs 0.000 claims abstract description 32
- 235000015523 tannic acid Nutrition 0.000 claims abstract description 32
- 239000002253 acid Substances 0.000 claims abstract description 25
- 238000004090 dissolution Methods 0.000 claims abstract description 11
- 238000001816 cooling Methods 0.000 claims abstract description 10
- 238000003756 stirring Methods 0.000 claims abstract description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 57
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 229920002498 Beta-glucan Polymers 0.000 claims description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- 238000005507 spraying Methods 0.000 claims description 9
- 239000003595 mist Substances 0.000 claims description 8
- 239000008177 pharmaceutical agent Substances 0.000 claims description 7
- 241000195493 Cryptophyta Species 0.000 claims description 4
- 229920002984 Paramylon Polymers 0.000 claims description 3
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims description 3
- 229910001863 barium hydroxide Inorganic materials 0.000 claims description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 3
- 239000000920 calcium hydroxide Substances 0.000 claims description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 3
- 230000035876 healing Effects 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 8
- 229920001503 Glucan Polymers 0.000 abstract description 6
- 241000699670 Mus sp. Species 0.000 abstract description 5
- 208000002874 Acne Vulgaris Diseases 0.000 abstract description 4
- 206010000496 acne Diseases 0.000 abstract description 4
- 230000001737 promoting effect Effects 0.000 abstract description 4
- 206010061218 Inflammation Diseases 0.000 abstract description 3
- 230000004054 inflammatory process Effects 0.000 abstract description 3
- 206010039509 Scab Diseases 0.000 abstract description 2
- 238000011161 development Methods 0.000 abstract description 2
- 230000003467 diminishing effect Effects 0.000 abstract description 2
- 239000000499 gel Substances 0.000 description 104
- 239000003814 drug Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 18
- 229940079593 drug Drugs 0.000 description 12
- 206010052428 Wound Diseases 0.000 description 11
- 208000027418 Wounds and injury Diseases 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 230000029663 wound healing Effects 0.000 description 10
- 239000004744 fabric Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000084 colloidal system Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 5
- PTHCMJGKKRQCBF-UHFFFAOYSA-N Cellulose, microcrystalline Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC)C(CO)O1 PTHCMJGKKRQCBF-UHFFFAOYSA-N 0.000 description 4
- 229920000855 Fucoidan Polymers 0.000 description 4
- 229920002978 Vinylon Polymers 0.000 description 4
- 239000000017 hydrogel Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- FYGDTMLNYKFZSV-URKRLVJHSA-N (2s,3r,4s,5s,6r)-2-[(2r,4r,5r,6s)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2r,4r,5r,6s)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1[C@@H](CO)O[C@@H](OC2[C@H](O[C@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-URKRLVJHSA-N 0.000 description 3
- 210000004207 dermis Anatomy 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000003760 magnetic stirring Methods 0.000 description 3
- 150000004804 polysaccharides Polymers 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 238000001804 debridement Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 210000000416 exudates and transudate Anatomy 0.000 description 2
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 2
- 229940114124 ferulic acid Drugs 0.000 description 2
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 2
- 235000001785 ferulic acid Nutrition 0.000 description 2
- 229920005640 poly alpha-1,3-glucan Polymers 0.000 description 2
- 230000008092 positive effect Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 230000010388 wound contraction Effects 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- 206010048038 Wound infection Diseases 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 231100000439 acute liver injury Toxicity 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000036436 anti-hiv Effects 0.000 description 1
- 230000002924 anti-infective effect Effects 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 108010025899 gelatin film Proteins 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 210000002865 immune cell Anatomy 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000000091 immunopotentiator Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000012982 microporous membrane Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000008855 peristalsis Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
-
- 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
- A61K31/74—Synthetic polymeric materials
- A61K31/785—Polymers containing nitrogen
- A61K31/787—Polymers containing nitrogen containing heterocyclic rings having nitrogen as a ring hetero atom
- A61K31/79—Polymers of vinyl pyrrolidone
-
- 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
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Inorganic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The application discloses a preparation method of high-crosslinking euglena polysaccharide gel, which comprises the following steps: dissolving Euglena polysaccharide with alkali solution with pH > 12; adding tannic acid with the mass of 0.5-5% of that of the euglena polysaccharide into alkali liquor, and stirring for more than 1 hour at 70-90 ℃ at 100-500 revolutions per minute to crosslink the euglena polysaccharide; cooling to room temperature; transferring the Euglena polysaccharide alkali liquor onto a flat plate, and controlling the thickness of the alkali liquor between 1 and 10 millimeters in order to ensure the uniformity of the high-crosslinking Euglena polysaccharide gel; adding acid to generate gel, and obtaining the high-crosslinking euglena polysaccharide gel. Based on the alkali dissolution characteristic of the euglena polysaccharide, the application provides a set of methods for increasing the intermolecular crosslinking degree and generating uniform gel, and the gel prepared by the method has the effects of diminishing inflammation and promoting healing. The glucan gel used in the application can obviously promote the healing of wound of mice, obviously relieve the development of acne and promote the healing of acne scab.
Description
Technical Field
The application belongs to the technical field of biological medicine, and in particular relates to a preparation method of high-crosslinking euglena polysaccharide gel.
Background
The Euglena polysaccharide is beta-1, 3-glucan particles accumulated in Euglena cells, and a plurality of international journal research papers show that the Euglena polysaccharide has the functions of resisting oxidation, regulating immunity, resisting tumor, reducing blood sugar, reducing blood fat, resisting radiation, resisting bacteria and viruses, resisting aging, protecting liver and the like. The euglena polysaccharide is insoluble in water, but is easily dissolved in alkali solution such as NaOH, and the like, and is alkali-soluble polysaccharide; the polysaccharide can form a more complex tertiary structure due to the interaction of the inside of molecules and the combination of intermolecular hydrogen bonds, and has a beta-1, 3 spiral structure under the analysis of X-ray diffraction, so that a stable hard rod structure can be formed. Meanwhile, the polysaccharide is in a porous structure, does not participate in metabolism in a human body, can promote small intestine peristalsis, and discharges redundant substances in the human body such as cholesterol, heavy metals, alcohol and the like out of the body. Studies have shown that Euglena polysaccharide has uric acid reducing, antiallergic, and potential immune thornActivators and immunopotentiators, anti-HIV viruses, anti-cancer and anti-CCl 4 The induced acute liver injury has antioxidant effect.
The molecular structural formula of the beta-1, 3-glucan is as follows:
the patent search shows that most of gel medical dressings are hydrogel dressings, the main component of the gel medical dressings is polymer gel with a three-dimensional reticular structure, and the gel medical dressings have the functions of absorbing wound exudates, keeping the wound moist, debridement and accelerating wound healing, but the gel medical dressings are physical gels which can be dissolved into solution (such as CN108310452A, CN101982202A, CN106562851A, CN 203226950U) at a higher temperature; while some of the gel only changes the strength of dressing (such as CN 112472867A) or only improves the mechanical strength and elasticity of hydrogel (such as CN 101224310B), while some gel can increase the solubility of insoluble drugs and improve the bioavailability (such as CN 112336685A), but can not be suitable for general medicines, compared with the above patent, the gel prepared from the naked algal polysaccharide produced by naked algae has the effects of activating immune cells, eliminating inflammation, promoting wound healing and the like, so that the gel has excellent anti-inflammatory effect besides the functions of absorbing wound exudates, keeping the wound moist, debridement, accelerating wound healing and the like of the traditional gel; according to the size of the drug molecules, the drugs can be added before crosslinking or after gel molding, and the anti-inflammatory effects of the gel are good supplements to the drug molecules, and positive effects on the curative effects are generated. The chain length of the euglena glucan molecule reaches more than 700 glucose residues, so that the crosslinking degree and the stability of the gel are high, the crosslinking degree is greatly improved after the euglena glucan molecule is further crosslinked under the action of a crosslinking agent, the tensile strength is remarkably improved, and stable gel with solubility not influenced by temperature is formed, so that the gel has high stability in the aspects of storage, transportation and the like, and the effective period of the gel is greatly prolonged. In addition, the gel is in a gel state below pH=12, has relatively wide pH adaptability, and does not change the gel state at a certain pH unlike gel formed by agar (gel cannot be formed when the pH is below pH=5), so that the pH of the gel can be adjusted to a proper range according to the requirement of medicines, and the gel dressing has more excellent medicine adaptability.
By contrast, the present patent application is substantially different from the patent publication.
Disclosure of Invention
The application aims to overcome the defects in the prior art and provides a preparation method of high-crosslinking euglena polysaccharide gel.
The technical scheme adopted for solving the technical problems is as follows:
a preparation method of high-crosslinking euglena polysaccharide gel comprises the following steps:
(1) Alkali dissolution: dissolving Euglena polysaccharide with alkali solution with pH > 12;
(2) Crosslinking: adding tannic acid with the mass of 0.5-5% of that of the euglena polysaccharide into alkali liquor, and stirring for more than 1 hour at 70-90 ℃ at 100-500 revolutions per minute to crosslink the euglena polysaccharide;
(3) And (3) cooling: cooling to room temperature;
(4) Paving: transferring the Euglena polysaccharide alkali liquor onto a flat plate, and controlling the thickness of the alkali liquor between 1 and 10 millimeters in order to ensure the uniformity of the high-crosslinking Euglena polysaccharide gel;
(5) Adding acid to generate gel, and obtaining the high-crosslinking euglena polysaccharide gel.
Further, the euglena polysaccharide in the step (1) is: beta-1, 3-glucan produced by naked algae, namely paramylon.
Further, the alkali liquor in the step (1) is sodium hydroxide or potassium hydroxide or calcium hydroxide or barium hydroxide with the pH value more than 12.
Further, the volume of the alkali liquor in the step (1) is more than or equal to 10 times of the volume of the euglena polysaccharide.
Further, the step (4) is to transfer the euglena polysaccharide alkali liquor to a flat disc with a film covered on the surface, wherein the film is a film with holes, and the aperture is smaller than 5 mu m.
Further, the step (5) is to spray acid mist drops on the surface of the euglena polysaccharide alkali liquor, and meanwhile, acid liquor is added between the flat plate and the film until the euglena polysaccharide alkali liquor is solidified and swelled, and the acid mist spraying is stopped.
Further, in the step (5), the acid is hydrochloric acid.
Further, the alkali liquor in the step (1) is NaOH solution with pH=12.5 and 1mol/L, and tannic acid with the mass of 1% of that of the euglena polysaccharide is added into the alkali liquor in the step (2).
Further, the step (5) is added with acid to form gel, and then the drug reagent to be embedded is further added or the drug reagent to be embedded is added after the step (1).
Further, the pharmaceutical agent to be entrapped is iodophor.
The application has the advantages and positive effects that:
1. based on the alkali dissolution characteristic of the euglena polysaccharide, the application provides a set of methods for increasing the intermolecular crosslinking degree and generating uniform gel, and the gel prepared by the method has the effects of diminishing inflammation and promoting healing. The glucan gel used in the application can obviously promote the healing of wound of mice, obviously relieve the development of acne and promote the healing of acne scab. Compared with the cellulose gel (or called cellulose hydrogel) wound dressing widely used in medical treatment at present, the gel prepared by the method has better effect on wound healing.
2. The gel prepared by the method is stable to heat, the gel characteristics are not influenced by high temperature, the gel is stable in use, easy to store and transport, and the shelf life is long.
3. The gel prepared by the method has wide pH range suitable for the gel, and the stability of the gel is not affected at any pH below pH=12. The application takes the euglena polysaccharide produced by euglena as the raw material, the pH of the dressing can be adjusted according to the optimal pH of the medicines (the optimal pH of each medicine is different, so that the medicines are generally limited in adding the dressing, but the pH of the product is only lower than 12 when the product forms gel, so that the pH of the gel can be adjusted to the required pH by adding acid liquor according to the optimal pH of the medicine which is required to be embedded), the utilization rate of the medicine is improved to the maximum, the viscosity of the dressing can be improved, the adhesiveness and the spreadability of the medicine and the skin are improved, and the residence time of the medicine is prolonged.
4. When the method is used for preparing the high-crosslinking euglena polysaccharide gel, the addition of tannic acid greatly improves the crosslinking degree of the high-crosslinking euglena polysaccharide gel, so that the tensile strength of the high-crosslinking euglena polysaccharide gel is 11 times that of the high-crosslinking euglena polysaccharide gel, the compressive strength of the high-crosslinking euglena polysaccharide gel is 8 times that of the high-crosslinking euglena polysaccharide gel, and the toughness and the firmness of the euglena glucan gel are obviously improved.
5. When the method is used for preparing, the cooled euglena polysaccharide alkali liquor is transferred to a flat plate for paving, and the paved and crosslinked alkali liquor can be used for quickly and uniformly mixing acid liquor sprayed in a later period, so that the method is beneficial to forming crosslinked high-crosslinking euglena polysaccharide gel.
6. When the method is used for preparing the gel, the microporous membrane is padded on the bottom of the alkali liquor and the acid liquor is sprayed, so that the acid liquor can enter the alkali liquor uniformly and slowly to form the gel, and further gel caking caused by instant excessive concentration of the acid liquor is avoided.
Drawings
FIG. 1 is an external view of a gel prepared by the method of the present application;
FIG. 2 is a schematic representation of a gel made by the method of the present application;
FIG. 3 is a graph showing the solubility of Euglena polysaccharide at different concentrations of NaOH in the present application;
FIG. 4 is a graph showing the effect of tannic acid concentration on the degree of crosslinking of euglena polysaccharide in the present application;
FIG. 5 is a photograph showing the wound healing promoting effect of the highly crosslinked Euglena polysaccharide gel of the present application;
FIG. 6 is a statistical plot of wound contraction area of highly crosslinked Euglena polysaccharide gel of the present application for wound healing promotion;
FIG. 7 is a statistical plot of the healed dermis area of the highly crosslinked Euglena polysaccharide gel of the present application for wound healing promotion;
FIG. 8 is a photograph of a highly crosslinked Euglena polysaccharide gel of the present application after solidification at-20 degrees Celsius;
FIG. 9 is a process flow diagram of the preparation method of the present application;
FIG. 10 is a graph showing the results of gel preparation by four different paths of dextran according to the present application.
Detailed Description
The following describes the embodiments of the present application in detail, but the present embodiments are illustrative and not limitative, and are not intended to limit the scope of the present application.
The raw materials used in the application are conventional commercial products unless specified; the methods used in the present application are conventional in the art unless otherwise specified.
A preparation method of euglena polysaccharide high-crosslinking gel comprises the following steps:
(1) Alkali dissolution: dissolving Euglena polysaccharide with alkali solution with pH > 12;
(2) Crosslinking: adding tannic acid with the mass of 0.5-5% of that of the euglena polysaccharide into alkali liquor, and stirring for more than 1 hour at 70-90 ℃ at 100-500 revolutions per minute to crosslink the euglena polysaccharide;
(3) And (3) cooling: cooling to room temperature;
(4) Paving: transferring the Euglena polysaccharide alkali liquor onto a flat plate, and controlling the thickness of the alkali liquor between 1 and 10 millimeters in order to ensure the uniformity of the high-crosslinking Euglena polysaccharide gel;
(5) Adding acid to generate gel, and obtaining the high-crosslinking euglena polysaccharide gel. The process flow diagram can be seen in fig. 9.
Preferably, the euglena polysaccharide in the step (1) is: beta-1, 3-glucan produced by naked algae, namely paramylon.
Preferably, the alkali liquor in the step (1) is sodium hydroxide or potassium hydroxide or calcium hydroxide or barium hydroxide with the pH value more than 12.
Preferably, the volume of the alkali liquor in the step (1) is more than or equal to 10 times of the volume of the euglena polysaccharide.
Preferably, the step (4) is to transfer the euglena polysaccharide alkali liquor onto a flat disc with a film covered on the surface, wherein the film is a film with holes, and the aperture is smaller than 5 mu m.
Preferably, the step (5) is to spray acid liquor droplets on the surface of the euglena polysaccharide alkali liquor, and simultaneously add acid liquor between the flat plate and the film until the euglena polysaccharide alkali liquor is solidified and swelled.
Preferably, the acid in the step (5) is hydrochloric acid.
Preferably, the alkali liquor in the step (1) is a NaOH solution with pH=12.5 and 1mol/L, and tannic acid with the mass of 1% of that of the euglena polysaccharide is added into the alkali liquor in the step (2).
Preferably, the step (5) is further added with a pharmaceutical agent to be embedded after the acid is added to form the gel or the pharmaceutical agent to be embedded is added after the step (1).
Preferably, the pharmaceutical agent to be entrapped is iodophor.
Specifically, the relevant preparation and detection examples are as follows:
example 1
600g of Euglena polysaccharide was divided into 6 parts, 100g of each, 1.5L of pure water (0 mol/L NaOH, pH 6), 0.25mol/L NaOH (pH 11), 0.5mol/L NaOH (pH 11.4), 1mol/L NaOH (pH 12.5), 2mol/L NaOH (pH 13.2) and 5mol/L NaOH (pH 13.6) were added to each part, and the dissolution was promoted by magnetic stirring to give a final volume of 1.6L. As shown in FIG. 3, the solubility of the Euglena polysaccharide increased with increasing NaOH concentration, and the Euglena polysaccharide was almost completely dissolved at 1mol/L, after which the NaOH concentration was continuously increased, and the Euglena polysaccharide was completely dissolved.
Then, the euglena polysaccharide alkali liquor of 1mol/L NaOH is selected to continue the embodiment. Adding 1 gram of tannic acid (1% of the mass of the euglena polysaccharide) into alkali liquor, and stirring at 150 revolutions per minute through water bath at 75 ℃ to crosslink the euglena polysaccharide chain for 1 hour; then cooling to room temperature (23 ℃), pouring into a square plate paved with vinylon filter cloth with the aperture of 0.3 micrometers, wherein the edge of the filter cloth is about 1 cm higher than the square plate, the height of the alkali liquor surface is 0.5 cm, spraying 3mol/L hydrochloric acid mist on the alkali liquor surface by using a spray can until the alkali liquor expands and solidifies into colloid, and continuing spraying until the pH value is 7.0, thus preparing the high-crosslinking euglena polysaccharide gel with the pH value (figures 1 and 2). The use of the gel for external application to a wound of a mouse can significantly promote contraction and dermal healing at a tissue defect after the wound (fig. 5). The fifth day after topical application, compared to the non-applied control and commercial cellulose gel topical application (cellulose gel is used as a drug slow release, wound healing, tissue engineering scaffold, etc. in medicine, therefore, the application will not be described in detail), the wound shrinkage area of the topical application of the highly crosslinked Euglena polysaccharide gel is more than 1 time smaller (fig. 6), and the healing dermis area is more than 1 time of the control group and cellulose gel group (fig. 7), showing that the highly crosslinked Euglena polysaccharide gel of the application has very remarkable effect on wound healing.
The highly crosslinked fucoidan gel prepared in this example was sealed in 5 glass bottles, respectively, and then placed in a refrigerator or oven at-20 ℃, -4 ℃,4 ℃,20 ℃,60 ℃ for one month, and after the placement, the highly crosslinked fucoidan gel at-20 ℃ was frozen (fig. 8), but the highly crosslinked fucoidan gel in the apparatus at-4 ℃ to 60 ℃ was not abnormal in morphology (fig. 1 and fig. 2), indicating that the highly crosslinked fucoidan gel prepared in this example had good thermal stability and low temperature stability.
After tannic acid is crosslinked, alkali liquor is swelled and solidified into colloid when the pH is lower than 12, 3mol/L hydrochloric acid is continuously added after the pH is regulated to 7.0 until the pH reaches 2.0, the morphology of the high-crosslinked euglena polysaccharide gel is not significantly different, and a tensile force experiment also shows that the tensile resistance of the gel is not statistically significantly different.
Example 2
600g of Euglena polysaccharide is taken and divided into 6 parts, 100g of Euglena polysaccharide are added with 1.5L of 1mol/L NaOH (pH 12.5) for dissolution, and the dissolution is promoted by magnetic stirring, and the final volume is 1.6L. To 5 parts of the alkali liquor, 0.5g of tannic acid (0.5% by weight), 1g of tannic acid (1% by weight), 2g of tannic acid (2% by weight) and 5g of tannic acid (5% by weight) were added in this order. Then, each part of alkali liquor is subjected to water bath at the temperature of 75 ℃ and is stirred at 150 revolutions per minute, so that the euglena polysaccharide chains are crosslinked for 1 hour; then cooling to room temperature (23 ℃), pouring into a square plate paved with vinylon filter cloth with the aperture of 0.3 micrometers, wherein the edge of the filter cloth is about 1 cm higher than the square plate, the height of the alkali liquor surface is 0.5 cm, spraying 3mol/L hydrochloric acid mist on the alkali liquor surface by using a spray can until the alkali liquor expands and solidifies into colloid, and continuing spraying until the pH value is 7.0, thus preparing the high-crosslinking euglena polysaccharide gel with the pH value.
The prepared 6 parts of gel are subjected to crosslinking degree analysis, the relative value of the tensile force when the gel film is subjected to tensile fracture is adopted to represent the crosslinking degree of the high crosslinking euglena polysaccharide gel, as shown in fig. 4, the result shows that the crosslinking degree of the high crosslinking euglena polysaccharide gel formed when tannic acid is 1 percent is maximum, the high crosslinking euglena polysaccharide gel formed at the moment has the strongest tensile resistance, a sample without tannic acid is added, after alkali dissolution, the hydrogel can be formed by adding acid liquor, but the gel is in an amorphous liquid state, the tensile resistance is extremely low, and the tensile force which can be born by the high crosslinking euglena polysaccharide gel prepared by adding 1 percent tannic acid is improved by more than 70 times compared with a control sample without tannic acid, so that the necessity of increasing the tensile force of the gel by using the crosslinking agent in the application is demonstrated. With the increase of the addition amount of tannic acid, the crosslinking degree of the high crosslinking euglena polysaccharide gel is not obviously improved, and the crosslinking degree has a descending trend, but the statistical analysis shows that the crosslinking degree is not obviously different.
Example 3
600g of Euglena polysaccharide is taken and divided into 6 parts, 100g of Euglena polysaccharide are added with 1.5L of 1mol/L NaOH (pH 12.5) for dissolution, and the dissolution is promoted by magnetic stirring, and the final volume is 1.6L. To 5 parts of the alkali liquor, 0.5g of tannic acid (0.5% by weight), 1g of tannic acid (1% by weight), 2g of tannic acid (2% by weight) and 5g of tannic acid (5% by weight) were added in this order. Then, each part of alkali liquor is subjected to water bath at the temperature of 75 ℃ and is stirred at 150 revolutions per minute, so that the euglena polysaccharide chains are crosslinked for 1 hour; then cooling to room temperature (23 ℃), pouring into a square plate paved with vinylon filter cloth with the aperture of 0.3 micrometers, wherein the edge of the filter cloth is about 1 cm higher than the square plate, the height of the alkali liquor surface is 0.5 cm, spraying 3mol/L hydrochloric acid mist on the alkali liquor surface by using a spray can until the alkali liquor expands and solidifies into colloid, and continuing spraying until the pH value is 7.0, thus preparing the high-crosslinking euglena polysaccharide gel with the pH value.
Taking 100ml of high-crosslinking euglena polysaccharide gel prepared by 1g tannic acid (1%wt), 2g tannic acid (2%wt) and 5g tannic acid (5%wt) in the embodiment, weighing and placing the high-crosslinking euglena polysaccharide gel into a vacuum drying oven, adding 10ml of medical iodophor solution into the high-crosslinking euglena polysaccharide gel, vacuumizing, and absorbing the iodophor solution into the high-crosslinking euglena polysaccharide gel about 10 minutes along with evaporation of water to obtain the high-crosslinking euglena polysaccharide iodophor gel. The three gels were used to conduct the mouse wound healing experiments in example 1. The results show that the high-crosslinking euglena polysaccharide gel has no difference between the wound contraction area and the healing dermis area and has obvious effect on preventing wound infection in the early stage, and each experimental group of 10 mice, a non-drug control group, a cellulose gel group and a high-crosslinking euglena polysaccharide gel group are all found that 2 to 3 mice are infected by bacteria on the next day after wound formation and are removed from the experiment. However, none of the 10 mice in the highly crosslinked Euglena polysaccharide iodophor gel group had a bacterial infection. The application shows that the application range and the efficiency of the high-crosslinking euglena polysaccharide gel can be widened after the high-crosslinking euglena polysaccharide gel is added with the medicine, namely the high-crosslinking euglena polysaccharide gel and the iodophor have a synergistic effect. There was no statistically significant difference in anti-infective ability between the three groups of gels (table 1).
TABLE 1 infection and healing data for different wound treatments (day five)
Example 4
Four commercially available beta-glucans were selected: euglena polysaccharide, yeast beta glucan, oat polysaccharide, beta-1, 3/alpha-1, 3-glucan; and then respectively placing the obtained products into four solutions with different pH values (pH values of 12.5, 12, 10 and 6), and the results show that the euglena polysaccharide is only dissolved in alkaline solution with the pH value of 12.5, and the yeast beta glucan, the oat polysaccharide and the beta-1, 3/alpha-1, 3-glucan are all soluble in the four solutions. Then the beta-glucan added with different solutions is divided into two parts, tannic acid or ferulic acid with the mass of 1% of the glucan is respectively added, the solutions are further divided into four parts, four water baths with the temperature are prepared, one part of the four parts added with tannic acid or ferulic acid is respectively put into one water bath for 1 hour, each part is divided into 4 parts, the parts are cooled to room temperature (23 ℃), the parts are respectively poured into square plates paved with vinylon filter cloth with the aperture of 0.3 micrometers, the edge of the filter cloth is higher than the square plates by about 1 cm, the heights of the solution surfaces are respectively 0.8mm, 1mm, 10mm and 11mm, then 3mol/L of hydrochloric acid mist is sprayed into each part to the solution surface by using a watering can until the solution expands to form colloid, the colloid is continuously sprayed to the pH value of 7.0, the result shows that only naked algal polysaccharide is dissolved by alkali solution with the pH value of 12.5, the tannic acid with the mass of 1% is paved into the liquid surface of 1mm or 10mm after the naked algal polysaccharide is crosslinked by 70 degrees, the liquid surface of the liquid surface is paved with the 6 mm, the liquid surface is respectively, the liquid surface of the liquid surface is sprayed with the liquid surface of the glue is not crosslinked until the liquid gel is 2 is similar to the pH 2 after the liquid is sprayed with the other gel is formed, and the liquid has the pH 2. It shows that gel with high crosslinking degree can be formed only by adding tannic acid and acid liquor at specific temperature and alkali liquor thickness when the Euglena polysaccharide is dissolved at pH 12.5. The example shows that the high cross-linked Euglena polysaccharide gel of the present application can not be prepared without any step or under other conditions, as shown in FIG. 10, only the preparation steps shown by the solid lines can obtain the high cross-linked Euglena polysaccharide gel, which has a synergistic effect between Euglena polysaccharide, alkali solution, tannic acid, cross-linking temperature and alkali solution thickness.
Although embodiments of the present application have been disclosed for illustrative purposes, those skilled in the art will appreciate that: various substitutions, changes and modifications are possible without departing from the spirit and scope of the application and the appended claims, and therefore the scope of the application is not limited to the disclosure of the embodiments.
Claims (10)
1. A preparation method of high-crosslinking euglena polysaccharide gel is characterized by comprising the following steps: the method comprises the following steps:
(1) Alkali dissolution: dissolving Euglena polysaccharide with alkali solution with pH > 12;
(2) Crosslinking: adding tannic acid with the mass of 0.5-5% of that of the euglena polysaccharide into alkali liquor, and stirring for more than 1 hour at 70-90 ℃ at 100-500 revolutions per minute to crosslink the euglena polysaccharide;
(3) And (3) cooling: cooling to room temperature;
(4) Paving: transferring the Euglena polysaccharide alkali liquor onto a flat plate, wherein the thickness of the alkali liquor is controlled between 1 and 10 millimeters in order to ensure the uniformity of the Euglena polysaccharide gel;
(5) Adding acid to generate gel to obtain the Euglena polysaccharide gel.
2. The method for preparing the high crosslinking euglena polysaccharide gel according to claim 1, wherein the method comprises the following steps: the euglena polysaccharide in the step (1) is as follows: beta-1, 3-glucan produced by naked algae, namely paramylon.
3. The method for preparing the high crosslinking euglena polysaccharide gel according to claim 1, wherein the method comprises the following steps: the alkali liquor in the step (1) is sodium hydroxide or potassium hydroxide or calcium hydroxide or barium hydroxide with the pH value more than 12.
4. The method for preparing the high crosslinking euglena polysaccharide gel according to claim 1, wherein the method comprises the following steps: the volume of the alkali liquor in the step (1) is more than or equal to 10 times of the volume of the euglena polysaccharide.
5. The method for preparing the high crosslinking euglena polysaccharide gel according to claim 1, wherein the method comprises the following steps: and (4) transferring the euglena polysaccharide alkali liquor to a flat plate with a film covered on the surface, wherein the film is a film with holes, and the aperture is smaller than 5 mu m.
6. The method for preparing the high crosslinking euglena polysaccharide gel according to claim 1, wherein the method comprises the following steps: and (5) spraying acid mist drops on the surface of the euglena polysaccharide alkali liquor, and simultaneously adding acid liquor between the flat plate and the film until the euglena polysaccharide alkali liquor is solidified and swelled, and stopping spraying acid mist.
7. The method for preparing the high crosslinking euglena polysaccharide gel according to claim 1, wherein the method comprises the following steps: the acid in the step (5) is hydrochloric acid.
8. The method for preparing the high crosslinking euglena polysaccharide gel according to claim 1, wherein the method comprises the following steps: the alkali liquor in the step (1) is NaOH solution with pH=12.5 and 1mol/L, and tannic acid with the mass of 1% of that of the euglena polysaccharide is added into the alkali liquor in the step (2).
9. The method for preparing a highly crosslinked Euglena polysaccharide gel according to any one of claims 1 to 8, characterized in that: and (3) adding acid to form gel in the step (5), and then further adding a pharmaceutical agent to be embedded or adding the pharmaceutical agent to be embedded after the step (1).
10. The method for preparing the highly crosslinked Euglena polysaccharide gel according to claim 9, wherein: the pharmaceutical agent to be embedded is iodophor.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210559443.9A CN114869843B (en) | 2022-05-23 | 2022-05-23 | Preparation method of high-crosslinking euglena polysaccharide gel |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210559443.9A CN114869843B (en) | 2022-05-23 | 2022-05-23 | Preparation method of high-crosslinking euglena polysaccharide gel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114869843A CN114869843A (en) | 2022-08-09 |
| CN114869843B true CN114869843B (en) | 2023-11-03 |
Family
ID=82676847
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210559443.9A Active CN114869843B (en) | 2022-05-23 | 2022-05-23 | Preparation method of high-crosslinking euglena polysaccharide gel |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114869843B (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07228601A (en) * | 1994-02-16 | 1995-08-29 | Otsuka Pharmaceut Co Ltd | Water-soluble beta-1,3-glucan derivative and antiviral agent containing the derivative |
| CN110448722A (en) * | 2019-08-20 | 2019-11-15 | 武汉大学 | A kind of injectable is containing the temperature sensitive composite antibacterial hydrogel material of tannic acid and its preparation and application |
| CN113679880A (en) * | 2021-08-25 | 2021-11-23 | 西北大学 | Gymnodinium polysaccharide hydrogel dressing as well as preparation method and application thereof |
-
2022
- 2022-05-23 CN CN202210559443.9A patent/CN114869843B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07228601A (en) * | 1994-02-16 | 1995-08-29 | Otsuka Pharmaceut Co Ltd | Water-soluble beta-1,3-glucan derivative and antiviral agent containing the derivative |
| CN110448722A (en) * | 2019-08-20 | 2019-11-15 | 武汉大学 | A kind of injectable is containing the temperature sensitive composite antibacterial hydrogel material of tannic acid and its preparation and application |
| CN113679880A (en) * | 2021-08-25 | 2021-11-23 | 西北大学 | Gymnodinium polysaccharide hydrogel dressing as well as preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN114869843A (en) | 2022-08-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DK168297B1 (en) | Process for producing low molecular weight heparin from normal heparin | |
| CN111632075B (en) | Exosome preparation for promoting skin wound healing and preparation method thereof | |
| CN107261200B (en) | Chitosan-nano-laponite composite gel wound dressing and preparation method thereof | |
| CN113069591A (en) | Chitosan-calcium polyglutamate biological dressing and preparation method thereof | |
| CN103083712A (en) | Stem cells or other bioactive substances doped surgical dressing | |
| CN113230449A (en) | Glucose and enzyme double-response dressing for treating chronic wound surface of diabetes and preparation method thereof | |
| KR20010016051A (en) | Layered air-gap sheet of chitosan and process therefor | |
| CN109700998B (en) | Compound skin injury regeneration repairing agent and preparation method thereof | |
| CN114869843B (en) | Preparation method of high-crosslinking euglena polysaccharide gel | |
| CN107049930B (en) | Wound healing promoting gel and preparation method thereof | |
| CN113350567A (en) | Biocompatible polymer dressing based on collagen | |
| CN109224124B (en) | Liquid dressing for stopping bleeding and promoting healing | |
| Ren et al. | Improving the antibacterial property of chitosan hydrogel wound dressing with licorice polysaccharide | |
| CN112023110B (en) | Active antibacterial dressing based on bamboo fungus egg extract | |
| CN115501246A (en) | Composition and preparation method and application thereof | |
| CN108451897A (en) | A kind of Propranolol Hydrochloride-polyvinyl alcohol cellular aqueogel and its preparation method and application | |
| CN104971345B (en) | Emodin gelatin microsphere and nano-silver composite gel preparation for treating burns and scalds | |
| CN108498851A (en) | A kind of hydrogel material and preparation method thereof | |
| CN1411805A (en) | Biological medicine film and its preparation method | |
| CN112121146B (en) | A topical gel for treating skin wound, and its preparation method | |
| CN113244268A (en) | Bacteriostatic gel containing sulfated polysaccharide-nano silver complex and application thereof | |
| CN113350568A (en) | Biocompatible polymer dressing based on gelatin | |
| CN106562953A (en) | Application of hydroxysafflor yellow A in preparing medicine for treating diabetic foot ulceration, medicine and medicine preparation method | |
| CN108404193B (en) | Bletilla striata hemostatic bandage product and preparation method thereof | |
| CN110101899A (en) | A kind of medical use hydrocolloid dressing and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |