WO2011070529A2 - Hydrogel de dextrine pour applications biomédicales - Google Patents

Hydrogel de dextrine pour applications biomédicales Download PDF

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Publication number
WO2011070529A2
WO2011070529A2 PCT/IB2010/055695 IB2010055695W WO2011070529A2 WO 2011070529 A2 WO2011070529 A2 WO 2011070529A2 IB 2010055695 W IB2010055695 W IB 2010055695W WO 2011070529 A2 WO2011070529 A2 WO 2011070529A2
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Prior art keywords
hydrogel
dextrin
previous
hydrogels
nanogel
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PCT/IB2010/055695
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English (en)
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WO2011070529A3 (fr
Inventor
Francisco Miguel Portela Da Gama
Maria Cabral Maio Molinos
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Universidade Do Minho
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Priority to EP10809176.0A priority Critical patent/EP2509644B1/fr
Priority to US13/515,228 priority patent/US9205103B2/en
Priority to ES10809176.0T priority patent/ES2558080T3/es
Publication of WO2011070529A2 publication Critical patent/WO2011070529A2/fr
Publication of WO2011070529A3 publication Critical patent/WO2011070529A3/fr

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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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A61K31/716—Glucans
    • A61K31/721—Dextrans
    • 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
    • A61L27/14—Macromolecular materials
    • A61L27/22—Polypeptides or derivatives thereof, e.g. degradation products
    • A61L27/227—Other specific proteins or polypeptides not covered by A61L27/222, A61L27/225 or A61L27/24
    • 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
    • A61L27/22—Polypeptides or derivatives thereof, e.g. degradation products
    • A61L27/24—Collagen
    • 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
    • A61L27/36—Materials for grafts or prostheses or for coating grafts or prostheses containing ingredients of undetermined constitution or reaction products thereof, e.g. transplant tissue, natural bone, extracellular matrix
    • A61L27/38—Materials for grafts or prostheses or for coating grafts or prostheses containing ingredients of undetermined constitution or reaction products thereof, e.g. transplant tissue, natural bone, extracellular matrix containing added animal cells
    • 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
    • A61L27/40—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material
    • A61L27/44—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material having a macromolecular matrix
    • A61L27/48—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material having a macromolecular matrix with macromolecular fillers
    • 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
    • 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
    • A61L27/56—Porous materials, e.g. foams or sponges
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • 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
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/12—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by a special physical form, e.g. emulsion, microcapsules, liposomes, characterized by a special physical form, e.g. emulsions, dispersions, microcapsules
    • A61K51/1213—Semi-solid forms, gels, hydrogels, ointments, fats and waxes that are solid at room temperature
    • 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
    • A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
    • A61L2300/252—Polypeptides, proteins, e.g. glycoproteins, lipoproteins, cytokines
    • 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
    • A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
    • A61L2300/602—Type of release, e.g. controlled, sustained, slow
    • 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
    • A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
    • A61L2300/62—Encapsulated active agents, e.g. emulsified droplets
    • A61L2300/624—Nanocapsules
    • 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
    • A61L2430/00—Materials or treatment for tissue regeneration
    • A61L2430/02—Materials or treatment for tissue regeneration for reconstruction of bones; weight-bearing implants

Definitions

  • Dextrin-based microspheres were used for encapsulation of the photosensitizer porphyrin, which aggregates in aqueous solutions, allowing its administration in the monomeric form, in photodynamic therapy (Luz et al . , 2008) .
  • Colin Brown (2010) developed also a dextrin formulation capable of preventing or reducing the incidence on postoperative adhesions (US2010/0240607A1) .
  • the present invention relates to the production of hydrogels made of dextrin and adipic acid dihydrazide, which can be injectable, with application as 1) scaffold for tissue regeneration; 2) as a carrier of bioactive microspheres, e.g. bioactive osteogenic granular compounds for bone regeneration adjuvancy; 3) cell encapsulation; 4) vehicle for bioactive molecules (namely proteins or polysaccharides, e.g. collagen) which promote cell adhesion and proliferation, and 5) self assembled nanogels (e.g. made of dextrin) associated drug delivery systems.
  • bioactive microspheres e.g. bioactive osteogenic granular compounds for bone regeneration adjuvancy
  • cell encapsulation e.g. cell encapsulation
  • vehicle for bioactive molecules namely proteins or polysaccharides, e.g. collagen
  • self assembled nanogels e.g. made of dextrin
  • a reticulating agent such as adipic acid dihydrazide
  • pH in the range 5,0-7,5 a reticulating agent
  • concentration between 3-40%, preferably between 3-10% on a molar basis relative to the glucose residues.
  • Figure 5 Compression curve showing typical behavior for a oDex DO 35% with 4% ADH hydrogel.
  • Figure 10 Morphologic evaluation of 3T3 cells in direct contact with dextrin hydrogels (DO 35%) , TCPS cell culture plates (control), agarose gel (negative control) and latex rubber (positive control). lOx magnification. Dark shadows on the left side show part of hydrogel or latex disc.
  • the quantification of aldehyde groups i.e. oxidation degree (DO)
  • DO oxidation degree
  • tBC trinitrobenzenosulfonic acid
  • Carbazates are well known to react with aldehydes to form stable carbazones in a similar manner to hydrazone formation, making it possible to determine the aldehyde content of dextrin by 1 H NMR spectroscopy analysis.
  • the degree of oxidation of oDex can be easily controlled by the relative quantity of sodium periodate used, enabling free aldehyde reactive groups to create covalent linkages with reticulating molecules (e.g. ADH) , as well as with cellular adhesion binding peptides (e.g GRGDY) or even with specific drugs for controlled delivery systems .
  • reticulating molecules e.g. ADH
  • GRGDY cellular adhesion binding peptides
  • hydrogels constitutes a matter of paramount importance on the perspective of its pharmaceutical or biomedical application.
  • a material is considered biocompatible when it verifies a complex and vast set of conditions (ISO 10993, 1992), including the absence of cytotoxicity and non-stimulation of an exacerbated inflammatory response.
  • hydrogels present good biocompatibility.
  • the determination of the materials cytotoxic potential may be qualitative and/or quantitative (ISO 10993-5, 1992).
  • Qualitative evaluation is based on microscopic observation of cells, aiming to conclude about general morphology, vacuolization, cellular adhesion and membrane lysis. Quantitative evaluation in turn is based on death indexes, growth, inhibition and cellular proliferation, or colony formation.
  • Example 4 provides the in vitro biocompatibility studies of oDex hydrogels, being applied both the evaluation methods mentioned above.
  • Dextrin-based hydrogels provided by the present invention are non-toxic. Cells adhere and proliferate along its interface, allowing the navaltion of a good tissue-hydrogel interaction in vivo .
  • proteins e.g., collagen and fibronectin
  • proteins possess peptidic sequences (e.g., RGD) , promoting a more efficient cellular adhesion, which may be necessary to enhance the viability and proliferation of cells incorporated on the hydrogel, to foment tissue regeneration mechanisms, for instance, through growth factors delivery.
  • polysaccharides such as chitosan or hyaluronic acid, among others, allow the variation of the hydrogels surface charge, making it positive or negative, respectively. Additionally, the selection of the molecular weight of the polysaccharides used (degradable for the mentioned cases) enables the modulation of the hydrogels mechanical properties and degradation profiles.
  • Nanogel particles can act as a drug reservoir from which release can be triggered by a stimulus (to which they are sensitive), or simply released in a diffusion- controlled manner. Simultaneous diffusion of molecules of different nature can be obtained from the same platform, by adding two (or more) different populations of nanogels loaded with different drugs in the same hydrogel matrix, where the release rate of each solute is controlled via the interaction between the hydrogel and the nanogels.
  • the major advantage relies on the improvement of the kinetic release profile of the drug, as the hydrogel phase provides an additional diffusion barrier moderating or eliminating the initial burst release typical observed in hydrogel or nanogel drug delivery systems.
  • Figure 5 presents a typical compression curve obtained for oDex hydrogels, from which the compressive modulus was determined, using equation 2:
  • Injectable hydrogels should be able to prosecute its polymerization process in situ, meaning the interstitial fluids and/or blood should not interfere with it, for instance by influence of the media pH . Also, the intrinsic conditions necessary for the hydrogel's formation must not be harmful to the surrounding tissues. Hence, the pH influence on the density of intermolecular bonds was evaluated by measuring the compressive modulus of various oDex hydrogels prepared in four different solvents: dd water (c.a pH 5.77), 0.1M phosphate buffer (pH 6.0), PBS (pH 7.4) and cDMEM (c.a pH 7.5), respectively. Results are shown in Figure 7.
  • the cell cytotoxicity was evaluated for un-crosslinked macromonomer solutions, crosslinked hydrogels and hydrogel degradation extracts using Live and Dead® and MTT assays, as described below.
  • fibroblasts adhesion to oDex hydrogels was also evaluated, by MTT assay.
  • oDEx hydrogels were formed at the bottom of the wells of a 96 well polystyrene culture plate. After 2h of polymerization, the oDex hydrogels were washed with PBS and three times with cDMEM. Then, 3T3 fibroblasts cells were added (3xl0 3 cells/well) to each well. The culture medium was refreshed every 2 days. For the control assays, cells were grown directly in the bottom of the wells. After 48h, hydrogels were carefully washed three times with PBS, to remove floating cells, and the cell layer was detached before conducting the MTT assay.
  • This Example also shows the studies on the release profile of dextrin nanogels imbebed in oDex/ADH hydrogels ( Figure 13).
  • Dextrin nanogels are produced according to Example 6, and have a similar degradation profile to oDex/ADH hydrogels.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
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  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Transplantation (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Dermatology (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Dispersion Chemistry (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Zoology (AREA)
  • Cell Biology (AREA)
  • Materials Engineering (AREA)
  • Botany (AREA)
  • Composite Materials (AREA)
  • Biophysics (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Organic Chemistry (AREA)
  • Rheumatology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Materials For Medical Uses (AREA)
  • Medicinal Preparation (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Polymers & Plastics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne une formulation d'hydrogel de dextrine oxydée réticulée avec du dihydrazide d'acide adipique, qui peut incorporer des polysaccharides, des protéines, des nanogels, des matériaux granulaires, des molécules bioactives et des cellules pour une régénération tissulaire et une administration de médicament contrôlée. La présente invention concerne un hydrogel injectable, hautement biocompatible et biodégradable, qui est destiné à des applications de régénération tissulaire et sert simultanément de véhicule pour, notamment, des nanogels, des matériaux granulaires et des cellules, et de système d'administration de médicament contrôlée, notamment de molécules hydrophobes et de protéines thérapeutiques.
PCT/IB2010/055695 2009-12-10 2010-12-09 Hydrogel de dextrine pour applications biomédicales WO2011070529A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP10809176.0A EP2509644B1 (fr) 2009-12-10 2010-12-09 Hydrogel de dextrine pour applications biomédicales
US13/515,228 US9205103B2 (en) 2009-12-10 2010-12-09 Dextrin hydrogel for biomedical applications
ES10809176.0T ES2558080T3 (es) 2009-12-10 2010-12-09 Hidrogel de dextrina para aplicaciones biomédicas

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
PT104879A PT104879B (pt) 2009-12-10 2009-12-10 Hidrogel de dextrino para aplicações biomédicas
PT104879 2009-12-10

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WO2011070529A2 true WO2011070529A2 (fr) 2011-06-16
WO2011070529A3 WO2011070529A3 (fr) 2011-11-10

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US (1) US9205103B2 (fr)
EP (1) EP2509644B1 (fr)
ES (1) ES2558080T3 (fr)
PT (1) PT104879B (fr)
WO (1) WO2011070529A2 (fr)

Cited By (4)

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US20140105960A1 (en) * 2012-10-12 2014-04-17 Children's Medical Center Corporation Hydrogels for tissue regeneration
EP2894172A1 (fr) * 2013-12-11 2015-07-15 Rohm and Haas Company Compositions aqueuses de polyaldéhydes produits par l'oxydation de polysaccharides et leurs produits thermodurcis
EP3011952A1 (fr) * 2014-10-24 2016-04-27 Centre National De La Recherche Scientifique -Cnrs- Hydrogels de libération de glucose temporisée et applications associées
WO2017001808A1 (fr) * 2015-07-02 2017-01-05 Universite De Lille 1, Sciences Et Technologies Procédé de fabrication d'hydrogel à base de chitosan et de polyélectrolytes chargés négativement et matériau poreux alvéolaire issu dudit hydrogel

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CN105399968B (zh) * 2015-12-14 2018-03-16 中国海洋大学 一种己二酸二酰肼交联羧甲基壳聚糖微球的制备方法
CN111253629B (zh) * 2020-03-17 2021-06-15 江苏地韵医疗科技有限公司 一种凝胶、其成套原料及应用
CN111804247A (zh) * 2020-07-21 2020-10-23 重庆盾之王安防设备技术研究院有限公司 一种纤维素纳米晶弹性多孔材料的制备方法及其应用
CN113198049B (zh) * 2021-04-13 2022-05-27 广州贝奥吉因生物科技股份有限公司 一种心肌修复水凝胶及其制备方法
CN113336536B (zh) * 2021-05-31 2022-11-15 大连理工大学 一种无机非金属纳米颗粒组装的水凝胶材料及其在增材制造技术中的应用

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