CA2299687A1 - Temperature-controlled ph-dependant formation of ionic polysaccharide gels - Google Patents

Temperature-controlled ph-dependant formation of ionic polysaccharide gels Download PDF

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Publication number
CA2299687A1
CA2299687A1 CA002299687A CA2299687A CA2299687A1 CA 2299687 A1 CA2299687 A1 CA 2299687A1 CA 002299687 A CA002299687 A CA 002299687A CA 2299687 A CA2299687 A CA 2299687A CA 2299687 A1 CA2299687 A1 CA 2299687A1
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CA
Canada
Prior art keywords
chitosan
temperature
phosphate
organo
dependant
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.)
Granted
Application number
CA002299687A
Other languages
French (fr)
Other versions
CA2299687C (en
Inventor
Abdellatif Chenite
Cyril Chaput
Christele Combes
Fayrouz Jalal
Amine Selmani
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Smith and Nephew Orthopaedics AG
Original Assignee
Individual
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from CA002212300A external-priority patent/CA2212300A1/en
Application filed by Individual filed Critical Individual
Priority to CA002299687A priority Critical patent/CA2299687C/en
Publication of CA2299687A1 publication Critical patent/CA2299687A1/en
Application granted granted Critical
Publication of CA2299687C publication Critical patent/CA2299687C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • A61K9/0024—Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue
    • 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
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Dermatology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Transplantation (AREA)
  • Dispersion Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Inorganic Chemistry (AREA)
  • Materials For Medical Uses (AREA)
  • Medicinal Preparation (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

The present invention relates to a temperature-controlled pH-dependant formation of ionic polysaccharide gels, such as chitosan/organo-phosphate aqueous systems, and methods of preparation thereof. While chitosan aqueous solutions are pH-dependant gelating systems, the addition of a mono-phosphate dibasic salt of polyol or sugar to chitosan aqueous solutions leads to further temperature-controlled pH-dependant gelation. Solid organo-phosphate salts (120 % w/v) are added and dissolved at low temperature (10 ~C) within 0.5 to 4.0 % w/v chitosan in aqueous acidic solutions. Aqueous chitosan/organo-phosphate solutions are initially stored at low temperatures (4 ~C), then endothermally gelated within the temperature range of 30 to 60 ~C. Chitosan/organo-phosphate solutions rapidly turn into gels at the desired gelation temperature. Gelation can be ex vivo within any receivers or molds, or in situ in animals or humans (in vivo) so as to fill a tissue defect or cavity.
CA002299687A 1997-08-04 1998-04-06 Temperature-controlled ph-dependant formation of ionic polysaccharide gels Expired - Lifetime CA2299687C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA002299687A CA2299687C (en) 1997-08-04 1998-04-06 Temperature-controlled ph-dependant formation of ionic polysaccharide gels

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CA002212300A CA2212300A1 (en) 1997-08-04 1997-08-04 In vitro or in vivo gelfying chitosan and therapeutic uses thereof
CA2,212,300 1997-08-04
PCT/CA1998/000326 WO1999007416A1 (en) 1997-08-04 1998-04-06 TEMPERATURE-CONTROLLED pH-DEPENDANT FORMATION OF IONIC POLYSACCHARIDE GELS
CA002299687A CA2299687C (en) 1997-08-04 1998-04-06 Temperature-controlled ph-dependant formation of ionic polysaccharide gels

Publications (2)

Publication Number Publication Date
CA2299687A1 true CA2299687A1 (en) 1999-02-18
CA2299687C CA2299687C (en) 2009-10-27

Family

ID=31888797

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002299687A Expired - Lifetime CA2299687C (en) 1997-08-04 1998-04-06 Temperature-controlled ph-dependant formation of ionic polysaccharide gels

Country Status (1)

Country Link
CA (1) CA2299687C (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012024785A1 (en) * 2010-08-27 2012-03-01 Oligo Medic Inc. Highly biocompatible dual thermogelling chitosan/glucosamine salt compositions
US8506972B2 (en) 2010-08-27 2013-08-13 Oligo Medic Inc Highly biocompatible dual thermogelling chitosan/glucosamine salt compositions
US9512192B2 (en) 2008-03-27 2016-12-06 Purdue Research Foundation Collagen-binding synthetic peptidoglycans, preparation, and methods of use
US9872887B2 (en) 2013-03-15 2018-01-23 Purdue Research Foundation Extracellular matrix-binding synthetic peptidoglycans
CN109957115A (en) * 2017-12-25 2019-07-02 成都昕才医药科技有限公司 A kind of temperature-sensitive hydrogel
US10772931B2 (en) 2014-04-25 2020-09-15 Purdue Research Foundation Collagen binding synthetic peptidoglycans for treatment of endothelial dysfunction
CN114874039A (en) * 2022-05-18 2022-08-09 普洱学院 Organic fertilizer for coffee pericarp and preparation method thereof
CN114948760A (en) * 2022-05-24 2022-08-30 上海家化联合股份有限公司 Polysaccharide-based gel containing salicylic acid and application thereof
US11529424B2 (en) 2017-07-07 2022-12-20 Symic Holdings, Inc. Synthetic bioconjugates

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102006036B1 (en) 2011-05-24 2019-07-31 시믹 아이피, 엘엘씨 Hyaluronic acid-binding synthetic peptidoglycans, preparation, and methods of use

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9512192B2 (en) 2008-03-27 2016-12-06 Purdue Research Foundation Collagen-binding synthetic peptidoglycans, preparation, and methods of use
US10689425B2 (en) 2008-03-27 2020-06-23 Purdue Research Foundation Collagen-binding synthetic peptidoglycans, preparation, and methods of use
EA024569B1 (en) * 2010-08-27 2016-09-30 Олиго Медик Инк. Highly biocompatible dual thermogelling chitosan/glucosamine salt compositions
US8784850B2 (en) 2010-08-27 2014-07-22 Oligo Médic Inc. Highly biocompatible dual thermogelling chitosan/glucosamine salt composition
AU2011293055B2 (en) * 2010-08-27 2016-01-07 Oligo Medic Inc. Highly biocompatible dual thermogelling chitosan/glucosamine salt compositions
CN103189435B (en) * 2010-08-27 2016-02-17 奥利高医疗公司 The dual Thermogelling chitosan/glucosamine salt composition of high degree of biocompatibility
WO2012024785A1 (en) * 2010-08-27 2012-03-01 Oligo Medic Inc. Highly biocompatible dual thermogelling chitosan/glucosamine salt compositions
US8506972B2 (en) 2010-08-27 2013-08-13 Oligo Medic Inc Highly biocompatible dual thermogelling chitosan/glucosamine salt compositions
CN103189435A (en) * 2010-08-27 2013-07-03 奥利高医疗公司 Highly biocompatible dual thermogelling chitosan/glucosamine salt compositions
US9872887B2 (en) 2013-03-15 2018-01-23 Purdue Research Foundation Extracellular matrix-binding synthetic peptidoglycans
US10772931B2 (en) 2014-04-25 2020-09-15 Purdue Research Foundation Collagen binding synthetic peptidoglycans for treatment of endothelial dysfunction
US11529424B2 (en) 2017-07-07 2022-12-20 Symic Holdings, Inc. Synthetic bioconjugates
CN109957115A (en) * 2017-12-25 2019-07-02 成都昕才医药科技有限公司 A kind of temperature-sensitive hydrogel
CN114874039A (en) * 2022-05-18 2022-08-09 普洱学院 Organic fertilizer for coffee pericarp and preparation method thereof
CN114948760A (en) * 2022-05-24 2022-08-30 上海家化联合股份有限公司 Polysaccharide-based gel containing salicylic acid and application thereof

Also Published As

Publication number Publication date
CA2299687C (en) 2009-10-27

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Effective date: 20180406