US20200230288A1 - Hydrogel using, as substrate, hyaluronic acid derivative modified with gallol group and use thereof - Google Patents

Hydrogel using, as substrate, hyaluronic acid derivative modified with gallol group and use thereof Download PDF

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Publication number
US20200230288A1
US20200230288A1 US16/483,146 US201816483146A US2020230288A1 US 20200230288 A1 US20200230288 A1 US 20200230288A1 US 201816483146 A US201816483146 A US 201816483146A US 2020230288 A1 US2020230288 A1 US 2020230288A1
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hyaluronic acid
hydrogel
group
crosslinking
present
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Seung Woo Cho
Jung-Seung Lee
Jung Ho Cho
Jong-seung LEE
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Amtixbio Co Ltd
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Amtixbio Co Ltd
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Assigned to AMTIXBIO CO., LTD. reassignment AMTIXBIO CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CHO, JUNG HO, CHO, SEUNG WOO, LEE, JONG-SEUNG, LEE, JUNG-SEUNG
Publication of US20200230288A1 publication Critical patent/US20200230288A1/en
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
    • C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
    • C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • A61K38/18—Growth factors; Growth regulators
    • A61K38/1808—Epidermal growth factor [EGF] urogastrone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • A61K38/18—Growth factors; Growth regulators
    • A61K38/1891—Angiogenesic factors; Angiogenin
    • 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
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/14—Macromolecular materials
    • A61L27/20—Polysaccharides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/52—Hydrogels or hydrocolloids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/54—Biologically active materials, e.g. therapeutic substances
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
    • C08J3/075—Macromolecular gels
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
    • C08L5/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/412—Tissue-regenerating or healing or proliferative agents
    • A61L2300/414—Growth factors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2400/00—Materials characterised by their function or physical properties
    • A61L2400/06—Flowable or injectable implant compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2400/00—Materials characterised by their function or physical properties
    • A61L2400/18—Modification of implant surfaces in order to improve biocompatibility, cell growth, fixation of biomolecules, e.g. plasma treatment
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2430/00—Materials or treatment for tissue regeneration
    • A61L2430/34—Materials or treatment for tissue regeneration for soft tissue reconstruction
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2305/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2301/00 or C08J2303/00
    • C08J2305/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00—Applications
    • C08L2203/02—Applications for biomedical use

Definitions

  • the present invention relates to a hydrogel based on a hyaluronic acid derivative modified with a gallol group, and a use thereof.
  • Hyaluronic acid is a bio-derived polymer which has little side effects when applied to the living body, and is hydrophilic due to a chemical structure of the sugar contained therein.
  • hyaluronic acid is known to have a physical buffering effect and a lubricating effect on friction in the joints, and to be involved in flexibility of the skin.
  • hyaluronic acid has protection characteristics against bacterial invasion from the outside and is biodegraded by hyaluronidase in a living body when transplanted into the living body.
  • Hyaluronic acid is utilized as an important material for drug delivery systems by causing the hyaluronic acid to be bound to various drugs.
  • hyaluronic acid since approval by the US Food and Drug Administration, hyaluronic acid has been extensively utilized as a medical biomaterial, a material of a scaffold for tissue engineering, and a polymer for drug delivery.
  • hyaluronic acid is abundantly present in several different layers of the skin, and has complex functions such as a function to supply moisture, a function to assist with tissue of extracellular matrix, a function to act as a filling material, and a function to be involved in tissue regeneration mechanism.
  • amounts of hyaluronic acid, collagen, elastin, and other matrix polymers present in the skin decrease.
  • a filler composition containing hyaluronic acid as a main component is widely used.
  • 5,356,883 discloses a synthesis example for a hyaluronic acid derivative gel whose carboxyl group has been modified with O-acylurea or N-acylurea using various carbodiimides.
  • hyaluronic acid crosslinked products prepared by the methods in these patents have low stability against a hyaluronic acid-degrading enzyme and a high content of unreacted chemicals, which may cause bio-toxicity.
  • it is not easy to control crosslinking or physical properties of these products depending on an intended use.
  • it is still required to develop a technique capable of easily controlling physical properties of a hyaluronic acid hydrogel while maintaining excellent biocompatibility thereof.
  • the present inventors have continually made efforts to develop a technique capable of improving functionality of hyaluronic acid which is a biocompatible material.
  • the present inventors have developed a hydrogel platform technique based on hyaluronic acid modified with a pyrogallol group, and have completed the present invention on the basis of this technique.
  • an object of the present invention is to provide a hyaluronic acid derivative prepared by modifying hyaluronic acid with a pyrogallol group and a method for preparing the same.
  • Another object of the present invention is to provide a method for preparing a hyaluronic acid derivative hydrogel, comprising a step of crosslinking the hyaluronic acid derivatives.
  • Yet another object of the present invention is to provide a hyaluronic acid derivative hydrogel having a structure in which the hyaluronic acid derivatives are crosslinked.
  • Still yet another object of the present invention is to provide a drug delivery carrier or drug delivery system (DDS) using the hyaluronic acid derivative hydrogel.
  • DDS drug delivery carrier or drug delivery system
  • Still yet another object of the present invention is to provide a medical material such as a scaffold for tissue engineering, using the hyaluronic acid derivative hydrogel.
  • Still yet another object of the present invention is to provide a wound dressing or adhesion barrier based on the hyaluronic acid derivative.
  • Still yet another object of the present invention is to provide a filler composition comprising the hyaluronic acid derivative hydrogel.
  • Still yet another object of the present invention is to provide a method for improving skin wrinkles, comprising a step of injecting the filler composition into or under the skin of an individual.
  • R 1 is a hydroxyl group
  • crosslinking in the crosslinking step, crosslinking may be carried out by adding an oxidizing agent or a pH adjusting agent, in which the oxidizing agent may be sodium periodate, hydrogen peroxide, horseradish peroxidase, or tyrosinase, and the pH adjusting agent may be sodium hydroxide, lithium hydroxide, potassium hydroxide, rubidium hydroxide, cesium hydroxide, magnesium hydroxide, calcium hydroxide, strontium hydroxide, or barium hydroxide.
  • the oxidizing agent may be sodium periodate, hydrogen peroxide, horseradish peroxidase, or tyrosinase
  • the pH adjusting agent may be sodium hydroxide, lithium hydroxide, potassium hydroxide, rubidium hydroxide, cesium hydroxide, magnesium hydroxide, calcium hydroxide, strontium hydroxide, or barium hydroxide.
  • the carrier includes, but is not limited to, an antibody, an antibody fragment, a protein, a peptide, a polypeptide, a small molecule chemical compound, DNA and/or RNA, siRNA, a gene, and stem cells including adult stem cells, mesenchymal stem cells, or induced pluripotent stem cells (iPSCs).
  • the carrier for delivery of a bioactive substance provides sustained release of the bioactive substance in vivo and ex vivo.
  • the disaccharide repeating unit of hyaluronic acid may be represented by the following Formula 4, and may be 1 to 1,000, but is not limited thereto.
  • the biological crosslinking includes crosslinking utilizing a binding force between heparin and growth factor, crosslinking using complementary bonding of DNA or the like, and the like.
  • the physical crosslinking includes crosslinking by hydrogen bonding, crosslinking by hydrophobic interaction, crosslinking utilizing electrostatic interaction, or the like.
  • crosslinking may be performed by adding an oxidizing agent or a pH adjusting agent.
  • a hyaluronic acid hydrogel prepared by crosslinking hyaluronic acid derivatives, each of which is represented by the above Formula 1, in which crosslinking represented by the above Formula 2 is formed between the hyaluronic acid derivatives; and a drug delivery carrier, a drug delivery system, or a scaffold for tissue engineering, comprising the hyaluronic acid hydrogel.
  • hydrogel formation and changes in elastic modulus over time were compared depending on crosslinking methods; and elasticity, adhesive strength, swelling, and degradation patterns depending on the crosslinking method and the degree of substitution of 5′-hydroxydopamine were respectively compared and analyzed.
  • the storage modulus (G′) was measured to be higher at a certain level than the loss modulus (G′′), which made it possible to identify that the hydrogels were stably formed ( FIG. 8( a ) ); and it was found that the hydrogel exhibits further improved rigidity and elastic force as hyaluronic acid has an increased molecular weight and has a higher concentration ( FIG. 8( b ) ).
  • each of the hydrogels was bridged between respective plates of a rheological instrument (Bohlin Advanced Rheometer, Malvern Instruments, Worcestershire, UK) and force applied to the instrument was measured while increasing spacing between the plates.
  • cytotoxicity and biocompatibility of the hyaluronic acid hydrogel of Preparation Example 2 were evaluated.
  • human adipose-derived stem cells hADSCs
  • LIVE/DEAD viability/cytotoxicity kit Invitrogen, Carlsbad, Calif., USA
  • the hADSCs were obtained from ATCC (ATCC, Manassas, Va. USA) and were cultured in the Mesenchymal Stem Cell Basal Medium (ATCC) supplemented with Growth Kit-low serum (ATCC) and 1% penicillin/streptomycin (Invitrogen).
  • a drug delivery preparation in the form of microparticles having a nano- or micro-unit diameter was prepared and efficacy thereof was identified.
  • an oil/water emulsion method was used to induce formation of an emulsion of the hyaluronic acid derivative solution (HA-PG) of Preparation Example 2, and an oxidizing agent (NaIO 4 ) was added to the solution.
  • HA-PG solution was mixed with a protein (bovine serum albumin, BSA), and the mixture was made into an emulsion form.
  • BSA bovine serum albumin
  • HA-PG microparticles into which VEGFs were applied to facilitate therapeutic angiogenesis in peripheral vascular diseases.
  • Intramuscular injection of VEGFs contained in HA-PG microparticles showed a remarkably improved therapeutic effect in a limb ischemic mouse model prepared by resection and ligation of femoral artery.
  • Mice (balb/c, 6-week-old female) were obtained from OrientBio Inc. After 4 weeks of injection, there was no leg cut or tissue necrosis in the group treated with the VEGF-containing HA-PG microparticles.
  • the HA-PG solutions of the present invention (200K, 1M) exhibited a remarkably low force value.
  • the HA-PG solution of the present invention can be easily injected regardless of extrusion force for injection, that is, an injection needle size.
  • the HA-PG solution of Preparation Example 1 was freeze-dried to prepare a filler composition in a powder form. Thereafter, the filler composition in a powder form was dissolved in PBS (pH 7) to be resolubilized, and then subcutaneously injected into mice to observe whether a hydrogel was formed.
  • PBS pH 7
  • FIG. 36 it was possible to identify that the filler composition of the present invention, which has been resolubilized in a freeze-dried powder state, is crosslinked by oxidizing power in the body to form a hydrogel as before.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Dermatology (AREA)
  • Dispersion Chemistry (AREA)
  • Transplantation (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Molecular Biology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Biochemistry (AREA)
  • Materials Engineering (AREA)
  • Biomedical Technology (AREA)
  • Inorganic Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Zoology (AREA)
  • Immunology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Vascular Medicine (AREA)
  • Materials For Medical Uses (AREA)
  • Medicinal Preparation (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Cosmetics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US16/483,146 2017-02-02 2018-02-02 Hydrogel using, as substrate, hyaluronic acid derivative modified with gallol group and use thereof Abandoned US20200230288A1 (en)

Applications Claiming Priority (5)

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KR20170014855 2017-02-02
KR10-2017-0014856 2017-02-02
KR10-2017-0014855 2017-02-02
KR20170014856 2017-02-02
PCT/KR2018/001473 WO2018143736A1 (fr) 2017-02-02 2018-02-02 Hydrogel utilisant en tant que substrat un derivé d'acide hyaluronique modifié par un groupe gallol, et utilisation associée

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US17/842,493 Division US20230147416A1 (en) 2017-02-02 2022-06-16 Hyaluronic acid derivative and use thereof
US17/842,475 Division US20220313866A1 (en) 2017-02-02 2022-06-16 Hyaluronic acid derivative and use thereof

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US17/842,493 Pending US20230147416A1 (en) 2017-02-02 2022-06-16 Hyaluronic acid derivative and use thereof
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US (3) US20200230288A1 (fr)
EP (1) EP3578573A4 (fr)
JP (1) JP6997470B2 (fr)
KR (1) KR102099981B1 (fr)
CN (1) CN110603268B (fr)
AU (1) AU2018216540B2 (fr)
BR (2) BR112019015891A2 (fr)
CA (1) CA3052135C (fr)
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CN113244437A (zh) * 2021-06-15 2021-08-13 福州大学 一种仿生多功能复合海绵敷料的制备方法与应用
CN113698539A (zh) * 2021-09-22 2021-11-26 四川大学 氧气调控力学性能的生物封闭材料及其制备方法
CN114632192A (zh) * 2022-03-23 2022-06-17 东莞市人民医院 锶-酚螯合物自组装涂层材料、其制备方法及应用
CN116270423A (zh) * 2023-01-12 2023-06-23 南方医科大学珠江医院 一种装载甲氨蝶呤的透明质酸水凝胶及其制备方法和应用
CN116462863A (zh) * 2023-06-15 2023-07-21 首都医科大学附属北京口腔医院 一种含载Mg2+单宁酸微粒子的没食子酸接枝壳聚糖水凝胶及制备方法和应用

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KR102308721B1 (ko) * 2019-03-14 2021-10-06 주식회사 세라트젠 세로토닌 수식 히알루론산을 포함하는 하이드로젤 및 이의 용도
IT201900006038A1 (it) * 2019-04-18 2020-10-18 Fidia Farm Spa Composizioni farmaceutiche comprendenti statine e derivati dell’acido ialuronico
US20220280442A1 (en) * 2019-07-09 2022-09-08 Cellartgen Inc. Bio-inspired tissue-adhesive hydrogel patch and uses thereof
WO2021162529A1 (fr) * 2020-02-14 2021-08-19 연세대학교 산학협력단 Hydrogel de sulfate de chondroïtine fonctionnalisé par un dérivé de phénol et son utilisation
WO2022045230A1 (fr) * 2020-08-27 2022-03-03 京セラ株式会社 Polymère biocompatible, composition biocompatible, sol ou gel, et composition injectable
KR102602244B1 (ko) * 2021-01-20 2023-11-16 주식회사 세라트젠 페놀 유도체가 수식된 탈세포화된 조직 유래 세포외기질 및 이의 용도
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