WO1991011206A1 - Alginate materials - Google Patents

Alginate materials Download PDF

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Publication number
WO1991011206A1
WO1991011206A1 PCT/GB1991/000119 GB9100119W WO9111206A1 WO 1991011206 A1 WO1991011206 A1 WO 1991011206A1 GB 9100119 W GB9100119 W GB 9100119W WO 9111206 A1 WO9111206 A1 WO 9111206A1
Authority
WO
WIPO (PCT)
Prior art keywords
alginate
cation
alginate material
cations
membrane
Prior art date
Application number
PCT/GB1991/000119
Other languages
French (fr)
Inventor
Dennis Keith Gilding
Original Assignee
Beam Tech Limited
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
Application filed by Beam Tech Limited filed Critical Beam Tech Limited
Publication of WO1991011206A1 publication Critical patent/WO1991011206A1/en

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L15/00Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42Use of materials characterised by their function or physical properties
    • A61L15/44Medicaments
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L15/00Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/22Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
    • A61L15/28Polysaccharides or their derivatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L2300/00Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/10Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing inorganic materials
    • A61L2300/102Metals or metal compounds, e.g. salts such as bicarbonates, carbonates, oxides, zeolites, silicates
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L2300/00Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/10Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing inorganic materials
    • A61L2300/102Metals or metal compounds, e.g. salts such as bicarbonates, carbonates, oxides, zeolites, silicates
    • A61L2300/104Silver, e.g. silver sulfadiazine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L2300/00Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/404Biocides, antimicrobial agents, antiseptic agents

Definitions

  • the present invention relates alginate materials which are useful particularly (but not exclusively) for wound dressings.
  • alginate materials have haemostatic and wound healing properties and may be used in various types of wound dressing * (see for example EP-A- 0 236 104 (Courtauld ⁇ ) ) .
  • alginates for wound dressings are prepared by spinning a solution of sodium alginate into a ' bath containing calcium ions (usually provided by calcium chloride) so that alginate material precipitates in the form of the insoluble calcium salt.
  • calcium ions usually provided by calcium chloride
  • the alginates are highly hydrophilic and have thus found particular use in the dressing of "highly exuding" wounds where this absorbing allows comparatively large quantities of exudate to be absorbed before the alginate material dissolves.
  • an alginate material which comprises of zinc, copper, silver, cerium, manganese, or cobalt cations and/or any cation which is an enzyme co-factor, save that the cation is not solely calcium, sodium or a mixture of these two cations.
  • Enzyme co-factors include Mg 2+ , Co 2+ , Mn + and Fe 3+ ions.
  • the cation (or mixture of abovementioned cations) provide exchangeable ions which have useful wound healing properties and the alginate serves as a base material for the delivery of these cations to the wound site.
  • the absorbency of the alginate material is an added advantage.
  • the minimum amount of the cation incorporated in the alginate material is preferably (l/2n) moles (of cation) per mole of sugar residue in the alginate.
  • the minimum amount is preferably 0.25 moles.
  • the preferred minimum amount is 0.5 moles (of cation).
  • the preferred maximum amount for the cation is (1/n) moles per mole of sugar residue in the alginate.
  • alginate materials of the invention may be used in a wide range of wound healing applications.
  • One particular application is for the treatment of leg ulcers which might contain in excess of 10 5 organisms/ml.
  • an alginate material containing copper ions may initially be applied to the ulcer and would cause the wound to flush itself.
  • a further alginate material containing zinc ions may be applied to the ulcer to promote wound healing.
  • the alginate material may be in the form of a porous membrane but is more preferably in the form of a porous fibrous material or of a particulate material of sufficiently small size for formulation into an aerosol (which may then be sprayed onto a wound) .
  • a porous fibrous material produced, for example, as described below is particulary advantageous because of the high internal surface are avoidable for ion-exchange.
  • Such a fibrous material may be produced by spinning a solution of a soluble alginate (particularly sodium or magnesium alginate) into bath containing the cations to be incorporated in the final alginate material.
  • the solution may, for example, be spun into a bath by dissolving the chloride or nitrate of zinc and/or silver in water.
  • Such fibrous materials may be supported in ' any suitable way for application to a wound site.
  • the support may, for example, comprise a porous textile dressing or a porous membrane or a porous polymeric membrane comprised of a hydrophobic polymer defining a porous (particularly microporous) structure and a hydrophilic polymer provided at the surfaces, including the internal pore surfaces, of the hydrophobic polymer.
  • a membrane is disclosed in WO-A-90/11820 (Beam Tech) .
  • Particulate alginate material for formulation into an aerosol
  • Particulate alginate material may be produced by subjecting particulate calcium alginate material to an ion exchange process with the appropriate cation(s).
  • An alginate membrane may be produced by preparing an aqueous solution of a soluble alginate material, forming the solution into the shape of a membrane, and treating the thus formed membrane precursor with a liquid containing cations which precipitate alginate material from solution as a porous membrane.
  • the precipitation bath may be aqueous or may be or include a water miscible organic solvent (e.g. DMSO, DMF).
  • a water miscible organic solvent e.g. DMSO, DMF.

Abstract

An alginate material useful particularly as a wound dressing incorporates cations selected from zinc, copper, silver, cerium, manganese, cobalt, or any cation which is an enzyme cofactor, save that the cation is not solely calcium, sodium or a mixture of these two cations.

Description

ALGINATE MATERIALS
The present invention relates alginate materials which are useful particularly (but not exclusively) for wound dressings.
It is known that alginate materials have haemostatic and wound healing properties and may be used in various types of wound dressing* (see for example EP-A- 0 236 104 (Courtauldε) ) .
Conventionally, alginates for wound dressings are prepared by spinning a solution of sodium alginate into a' bath containing calcium ions (usually provided by calcium chloride) so that alginate material precipitates in the form of the insoluble calcium salt. For certain applications, it may be desirable for the alginate to have a greater degree of solubility in body fluids, in which case the calcium alginate may be treated in a bath of sodium ions so that some of the calcium is replaced by sodium to provide a more soluble form.
The alginates are highly hydrophilic and have thus found particular use in the dressing of "highly exuding" wounds where this absorbing allows comparatively large quantities of exudate to be absorbed before the alginate material dissolves.
It is a object of the present invention to provide alginate materials with improved properties for the treatment of wounds.
According to the present invention there is provide an alginate material which comprises of zinc, copper, silver, cerium, manganese, or cobalt cations and/or any cation which is an enzyme co-factor, save that the cation is not solely calcium, sodium or a mixture of these two cations. Enzyme co-factors include Mg2+, Co2+, Mn + and Fe3+ ions.
In the alginate material of the invention, the cation (or mixture of abovementioned cations) provide exchangeable ions which have useful wound healing properties and the alginate serves as a base material for the delivery of these cations to the wound site. The absorbency of the alginate material is an added advantage.
Assuming that the cation has an oxidation slate of n+ the minimum amount of the cation incorporated in the alginate material is preferably (l/2n) moles (of cation) per mole of sugar residue in the alginate. Thus, for a divalent ion (n=2) the minimum amount is preferably 0.25 moles. Similarly for a monovalent ion (n=l) the preferred minimum amount is 0.5 moles (of cation). The preferred maximum amount for the cation is (1/n) moles per mole of sugar residue in the alginate. Thus the preferred maximum for divalent cation (n=2) is 0.5 moles.
The ions shown below have the indicated properties:
Ion Wound Healing Property
Zn2+ promotes healing
Ag+ bactericidal action
Cu2+ anti-microbial, wound flushing
Ce + anti-immunosuppressant
Mn2+ enzyme (oxidase) co-factor
Co + enzyme co-factor
It will thus be appreciated that alginate materials of the invention may be used in a wide range of wound healing applications. One particular application is for the treatment of leg ulcers which might contain in excess of 105 organisms/ml. In this case, an alginate material containing copper ions may initially be applied to the ulcer and would cause the wound to flush itself. Subsequently, a further alginate material containing zinc ions may be applied to the ulcer to promote wound healing.
In order to assist delivery of the cations into the wound, it is possible to use an iontophoretic technique so as to "drive" the ions into the wound.
The alginate material may be in the form of a porous membrane but is more preferably in the form of a porous fibrous material or of a particulate material of sufficiently small size for formulation into an aerosol (which may then be sprayed onto a wound) . The use of a porous fibrous material (produced, for example, as described below) is particulary advantageous because of the high internal surface are avoidable for ion-exchange.
Such a fibrous material may be produced by spinning a solution of a soluble alginate (particularly sodium or magnesium alginate) into bath containing the cations to be incorporated in the final alginate material. The solution may, for example, be spun into a bath by dissolving the chloride or nitrate of zinc and/or silver in water.
Such fibrous materials may be supported in 'any suitable way for application to a wound site. The support may, for example, comprise a porous textile dressing or a porous membrane or a porous polymeric membrane comprised of a hydrophobic polymer defining a porous (particularly microporous) structure and a hydrophilic polymer provided at the surfaces, including the internal pore surfaces, of the hydrophobic polymer. Such a membrane is disclosed in WO-A-90/11820 (Beam Tech) .
Particulate alginate material (for formulation into an aerosol) may be produced by subjecting particulate calcium alginate material to an ion exchange process with the appropriate cation(s).
An alginate membrane may be produced by preparing an aqueous solution of a soluble alginate material, forming the solution into the shape of a membrane, and treating the thus formed membrane precursor with a liquid containing cations which precipitate alginate material from solution as a porous membrane.
The precipitation bath may be aqueous or may be or include a water miscible organic solvent (e.g. DMSO, DMF).

Claims

1. An alginate material which incorporates cations selected from zinc, copper, silver, cerium, manganese, cobalt, or any cation which is an enzyme cofactor, save that the cation is not solely calcium, sodium or a mixture of these two cations.
2. A material as claimed in claim 1 including an enzyme cofactor selected from Mg2+, Co2+, Mn2+, and Fe3+.
3. An alginate material as claimed in claim 1 or 2 wherein the alginate material is in the form of a fibre, a membrane, a film, or in the form of particles.
4. An alginate material as claimed in claim 3 wherein the alginate material comprises particles in the form of an aerosol.
5. A wound dressing comprising an alginate material as claimed in any one of claims 1 to 3.
6. A wound dressing as claimed in claim 4 wherein the alginate material is associated with a porous membrane comprised of a hydrophobic polymer defining the porous structure and a hydrophilic polymer provided at the surfaces, including the internal pore surfaces, of the hydrophobic polymer.
7. A method of producing an alginate material as claimed in claim 1 comprising providing a solution of a soluble alginate (preferably sodium or magnesium alginate) in a precipitation bath which contains at least one of said cations.
8. A method as claimed in claim 6 wherein said soluble alginate is spun into the bath to produce a fibre.
9. A method as claimed in claim 6 wherein said solution of the soluble alginate material is formed into the shape of a membrane and introduced into the precipitation bath.
10. A material as claimed in any one of claims 1 to 4 wherein the cation has an oxidation state of n+ and the amount of the cation present in the alginate material is at least (l/2n) moles per mole of sugar residue.
PCT/GB1991/000119 1990-01-26 1991-01-28 Alginate materials WO1991011206A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9001878.9 1990-01-26
GB909001878A GB9001878D0 (en) 1990-01-26 1990-01-26 Alginate materials

Publications (1)

Publication Number Publication Date
WO1991011206A1 true WO1991011206A1 (en) 1991-08-08

Family

ID=10669992

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1991/000119 WO1991011206A1 (en) 1990-01-26 1991-01-28 Alginate materials

Country Status (3)

Country Link
AU (1) AU7227991A (en)
GB (1) GB9001878D0 (en)
WO (1) WO1991011206A1 (en)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4204012A1 (en) * 1992-02-12 1993-08-19 Ulrich Prof Dr Zimmermann MITOGEN-FREE SUBSTANCE, THEIR PRODUCTION AND USE
WO1994000164A1 (en) * 1992-06-29 1994-01-06 C. V. Laboratories Limited Sustained release alginate fibre and process for the preparation thereof
WO1995004078A1 (en) * 1993-07-30 1995-02-09 University College London Cell adhesion protein complexes with copper
EP1153620A2 (en) * 2000-05-12 2001-11-14 Johnson & Johnson Medical Ltd. Solid compositions exhibiting selective binding to dissolved iron
US6372248B1 (en) * 1994-10-28 2002-04-16 Innovative Technologies Limited Dehydrated hydrogels
EP1252901A1 (en) * 2001-04-25 2002-10-30 Les Laboratoires Brothier Powdered wound dressing and method for producing the same
GB2392913A (en) * 2002-09-11 2004-03-17 Johnson & Johnson Medical Ltd Complex of an anionic polysaccharide with silver
WO2004024197A1 (en) 2002-09-11 2004-03-25 Johnson & Johnson Medical Limited Wound dressing materials comprising complexes of anionic polysaccharides with silver
WO2004084961A1 (en) * 2003-03-28 2004-10-07 Coloplast A/S A wound dressing
US6861570B1 (en) 1997-09-22 2005-03-01 A. Bart Flick Multilayer conductive appliance having wound healing and analgesic properties
EP1882482A2 (en) 2001-09-12 2008-01-30 ConvaTec Limited Antibacterial wound dressing
US7385101B2 (en) 2001-12-20 2008-06-10 Noble Fiber Technologies, Llc Antibiotic textile materials suitable for wound dressings and wound dressings incorporating the same
WO2009097672A2 (en) * 2008-02-08 2009-08-13 Luiz Eduardo Da Cruz Pharmaceutical composition, dressing and method for treating skin lesion, intermediate composition and process for preparing said dressing, and use of cerium salt associated with a collagen matrix
US8124826B2 (en) 2003-11-18 2012-02-28 Systagenix Wound Management (Us), Inc. Antioxidant and antimicrobial wound dressing materials
US8507652B2 (en) 2008-02-08 2013-08-13 Luis Eduardo da Cruz Pharmaceutical composition, dressing and method for treating skin lesion, intermediate composition and process for preparing said dressing, and use of cerium salt associated with a collagen matrix
US8728513B2 (en) 2000-09-21 2014-05-20 Convatec Technologies Inc. Silver containing wound dressing
EP1942851B1 (en) 2005-11-02 2016-11-23 BSN medical GmbH Absorptive element to be mounted on human or animal skin surfaces
WO2018214007A1 (en) 2017-05-23 2018-11-29 惠州华阳医疗器械有限公司 Antibacterial wound dressing and preparation method and application thereof
US11061033B2 (en) 2016-04-05 2021-07-13 University of Pittsburgh—of the Commonwealth System of Higher Education Assay for detection of bladder or prostate cancer

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB629419A (en) * 1946-12-05 1949-09-20 Johnson & Johnson Great Britai Improvements in and relating to surgical dressings
GB976301A (en) * 1960-10-27 1964-11-25 Calmic Ltd Preparation and use of alginates
GB1255155A (en) * 1968-10-30 1971-12-01 Wallace Cameron & Company Ltd Improvements in or relating to preformed surgical or medical dressings
GB1328088A (en) * 1969-09-27 1973-08-30 Wallace Cameron Co Ltd Solubilized alginic materials
EP0243069A2 (en) * 1986-04-17 1987-10-28 JOHNSON & JOHNSON MEDICAL, INC. Adhesive wound dressing

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB629419A (en) * 1946-12-05 1949-09-20 Johnson & Johnson Great Britai Improvements in and relating to surgical dressings
GB976301A (en) * 1960-10-27 1964-11-25 Calmic Ltd Preparation and use of alginates
GB1255155A (en) * 1968-10-30 1971-12-01 Wallace Cameron & Company Ltd Improvements in or relating to preformed surgical or medical dressings
GB1328088A (en) * 1969-09-27 1973-08-30 Wallace Cameron Co Ltd Solubilized alginic materials
EP0243069A2 (en) * 1986-04-17 1987-10-28 JOHNSON & JOHNSON MEDICAL, INC. Adhesive wound dressing

Cited By (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4204012A1 (en) * 1992-02-12 1993-08-19 Ulrich Prof Dr Zimmermann MITOGEN-FREE SUBSTANCE, THEIR PRODUCTION AND USE
WO1994000164A1 (en) * 1992-06-29 1994-01-06 C. V. Laboratories Limited Sustained release alginate fibre and process for the preparation thereof
US5690955A (en) * 1992-06-29 1997-11-25 E. R. Squibb & Sons, Inc. Sustained release alginate fibre and process for the preparation thereof
WO1995004078A1 (en) * 1993-07-30 1995-02-09 University College London Cell adhesion protein complexes with copper
US5798116A (en) * 1993-07-30 1998-08-25 University College London Stabilized materials comprised of copper ion-containing fibronectin mats
US6372248B1 (en) * 1994-10-28 2002-04-16 Innovative Technologies Limited Dehydrated hydrogels
US6861570B1 (en) 1997-09-22 2005-03-01 A. Bart Flick Multilayer conductive appliance having wound healing and analgesic properties
EP1153620A3 (en) * 2000-05-12 2003-05-28 Johnson & Johnson Medical Ltd. Solid compositions exhibiting selective binding to dissolved iron
EP1153620A2 (en) * 2000-05-12 2001-11-14 Johnson & Johnson Medical Ltd. Solid compositions exhibiting selective binding to dissolved iron
US10391197B2 (en) 2000-09-21 2019-08-27 Convatec Technologies Inc. Silver containing wound dressing
US8728513B2 (en) 2000-09-21 2014-05-20 Convatec Technologies Inc. Silver containing wound dressing
US10010647B2 (en) 2000-09-21 2018-07-03 Convatec Technologies Inc. Silver containing wound dressing
US9066989B2 (en) 2000-09-21 2015-06-30 Convatec Technologies Inc. Silver containing wound dressing
US9345805B2 (en) 2000-09-21 2016-05-24 Convatec Technologies Inc. Silver containing wound dressing
EP1252901A1 (en) * 2001-04-25 2002-10-30 Les Laboratoires Brothier Powdered wound dressing and method for producing the same
EP1882482A2 (en) 2001-09-12 2008-01-30 ConvaTec Limited Antibacterial wound dressing
US10342890B2 (en) 2001-09-12 2019-07-09 Convatec Limited Antibacterial wound dressing
US8828424B2 (en) 2001-09-12 2014-09-09 Convatec Limited Antibacterial wound dressing
US7385101B2 (en) 2001-12-20 2008-06-10 Noble Fiber Technologies, Llc Antibiotic textile materials suitable for wound dressings and wound dressings incorporating the same
GB2392913B (en) * 2002-09-11 2007-04-04 Johnson & Johnson Medical Ltd Wound dressings comprising complexes of oxidised celluloses with silver
US8461410B2 (en) 2002-09-11 2013-06-11 Ethicon, Inc. Wound dressing materials comprising complexes of anionic polysaccharides with silver
WO2004024197A1 (en) 2002-09-11 2004-03-25 Johnson & Johnson Medical Limited Wound dressing materials comprising complexes of anionic polysaccharides with silver
GB2392913A (en) * 2002-09-11 2004-03-17 Johnson & Johnson Medical Ltd Complex of an anionic polysaccharide with silver
WO2004084961A1 (en) * 2003-03-28 2004-10-07 Coloplast A/S A wound dressing
US8124826B2 (en) 2003-11-18 2012-02-28 Systagenix Wound Management (Us), Inc. Antioxidant and antimicrobial wound dressing materials
US10143771B2 (en) 2003-11-18 2018-12-04 Kci Usa, Inc. Antioxidant and antimicrobial wound dressing materials
EP2359784B1 (en) 2005-11-02 2017-09-27 BSN medical GmbH Absorption body for attachment to human or animal skin surfaces
EP1942851B1 (en) 2005-11-02 2016-11-23 BSN medical GmbH Absorptive element to be mounted on human or animal skin surfaces
US10166147B2 (en) 2005-11-02 2019-01-01 Bsn Medical Gmbh Absorbent article for application to human or animal skin surfaces
US10327955B2 (en) 2005-11-02 2019-06-25 Bsn Medical Gmbh Absorbent article for application to human or animal skin surfaces
US8507652B2 (en) 2008-02-08 2013-08-13 Luis Eduardo da Cruz Pharmaceutical composition, dressing and method for treating skin lesion, intermediate composition and process for preparing said dressing, and use of cerium salt associated with a collagen matrix
JP2011511013A (en) * 2008-02-08 2011-04-07 エデュアルド ダ クルス,ルイス Pharmaceutical compositions, dressings and methods for treating skin lesions, intermediate compositions and processes for preparing the dressings, and use of cerium salts in combination with a collagen matrix
WO2009097672A3 (en) * 2008-02-08 2010-05-20 Luiz Eduardo Da Cruz Pharmaceutical composition, dressing and method for treating skin lesion, intermediate composition and process for preparing said dressing, and use of cerium salt associated with a collagen matrix
WO2009097672A2 (en) * 2008-02-08 2009-08-13 Luiz Eduardo Da Cruz Pharmaceutical composition, dressing and method for treating skin lesion, intermediate composition and process for preparing said dressing, and use of cerium salt associated with a collagen matrix
US11061033B2 (en) 2016-04-05 2021-07-13 University of Pittsburgh—of the Commonwealth System of Higher Education Assay for detection of bladder or prostate cancer
WO2018214007A1 (en) 2017-05-23 2018-11-29 惠州华阳医疗器械有限公司 Antibacterial wound dressing and preparation method and application thereof
US11129847B2 (en) 2017-05-23 2021-09-28 Huizhou Foryou Medical Devices Co., Ltd. Antibacterial wound dressing, method for preparing the same, and use thereof

Also Published As

Publication number Publication date
GB9001878D0 (en) 1990-03-28
AU7227991A (en) 1991-08-21

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