WO2014152649A1 - Implants orthopédiques à auto-stérilisation à efficacité améliorée - Google Patents

Implants orthopédiques à auto-stérilisation à efficacité améliorée Download PDF

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Publication number
WO2014152649A1
WO2014152649A1 PCT/US2014/027576 US2014027576W WO2014152649A1 WO 2014152649 A1 WO2014152649 A1 WO 2014152649A1 US 2014027576 W US2014027576 W US 2014027576W WO 2014152649 A1 WO2014152649 A1 WO 2014152649A1
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WIPO (PCT)
Prior art keywords
acid
silver
peek
sulfuric acid
metal ions
Prior art date
Application number
PCT/US2014/027576
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English (en)
Inventor
Joseph J. Crudden
Original Assignee
Difusion Technologies, Inc.
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Filing date
Publication date
Application filed by Difusion Technologies, Inc. filed Critical Difusion Technologies, Inc.
Publication of WO2014152649A1 publication Critical patent/WO2014152649A1/fr

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Classifications

    • 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
    • A61L27/18—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
    • A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
    • A61L2/23—Solid substances, e.g. granules, powders, blocks, tablets
    • A61L2/238—Metals or alloys, e.g. oligodynamic metals
    • 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
    • A61L2300/10—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing inorganic materials
    • A61L2300/102—Metals or metal compounds, e.g. salts such as bicarbonates, carbonates, oxides, zeolites, silicates
    • 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
    • A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
    • 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

Definitions

  • Implantable medical devices are implanted into the body for various reasons, including orthopedics (e.g., hip repair and replacement, spinal procedures, knee repair and replacement, bone fracture repair, small bone surgery, and cranial surgery, which may include the placement of flaps and plates, etc.) .
  • orthopedics e.g., hip repair and replacement, spinal procedures, knee repair and replacement, bone fracture repair, small bone surgery, and cranial surgery, which may include the placement of flaps and plates, etc.
  • materials of fabrication are limited, and conventionally include metal, plastic and composites.
  • the benefits derived from these devices are often offset by infection, which can lead to sepsis and death.
  • the most common organisms causing infections are Staphylococcus epidermidis and Staphylococcus aureus.
  • Other gram-positive bacteria, gram-negative bacteria and fungal organisms also are problematic.
  • MRSA Methicillin-resistant Staphylococcus aureus
  • a type of staphylococcus bacteria that are resistant to many antibiotics.
  • MRSA infections are more difficult to treat than ordinary staph infections, and have become a serious problem.
  • Many pathogenic bacteria can form multicellular coatings, called biofilms on bioengineered implants. Biofilms can facilitate the proliferation and transmission of microorganisms by providing a stable protective environment. These biofilms, when well developed, can disseminate bacterial planktonic showers which can result in broad systemic infection.
  • Bioengineered materials act as excellent hosts for the formation of bacterial biofilms. Occasionally, (the implant itself carries the infecting organism) implants develop very tenacious biofilms seeded by infecting organisms. When this occurs, usually the implant must be removed, the patient must be treated with a prolonged course of one or more antibiotics in an effort to cure the infection, and a new implant is then re-implanted. This obviously subjects the patient to additional trauma and pain, and is extremely expensive .
  • Ceramics such as zeolite function as a cation cage, being able to be loaded with silver and other cations having antimicrobial properties.
  • Metal zeolites can be used as an antimicrobial agent, such as by being mixed with the resins used as thermoplastic materials to make the implantable devices, or as coatings to be applied to the devices; see, for example, U.S. Patent No. 6,582,715, the disclosure of which is hereby incorporated by reference.
  • the antimicrobial metal zeolites can be prepared by replacing all or part of the ion-exchangeable ions in zeolite with ammonium ions and antimicrobial metal ions. Usually not all of the ion-exchangeable ions are replaced.
  • PEEK polyetheretherketone
  • PEEK polyetheretherketone
  • antimicrobial zeolite such as silver zeolite
  • PEEK molten PEEK
  • the controlled release of cationic metal ions such as silver from molded plastics and from coated surfaces can be affected by incorporating a metal ion, or silver loaded zeolite into the plastic during compounding, or into the surface coating material during formulation.
  • a metal ion, or silver loaded zeolite into the plastic during compounding, or into the surface coating material during formulation.
  • systems can be formulated which show high efficacy against bacteria while being safe for contact with mammalian tissue.
  • PEEK spinal implants for example, can be produced by extrusion of rods of the polymer of the molten PEEK with subsequent machining of the material into the required shapes and sizes of implants for use in surgical procedures.
  • implants can be injection molded.
  • Metal zeolites can be incorporated into the molten PEEK before extrusion in order to confer osseointegrative and antimicrobial properties to the implant material.
  • the rate of release of metal ions from the surface of polymer articles such as implant materials can be enhanced by treating the polymer with certain acids and/or solvents.
  • certain acids and/or solvents include acids and/or solvents.
  • the interaction of the acids and solvents with the polymer composite may strip away microlayers of polymer or oxidized materials from around the surface of the metal zeolite particles thereby allowing for greater contact with the surrounding fluids and an enhanced rate of metal ion release.
  • the reaction of the acid or solvent with the polymer may produce moieties, which are more hydrophilic and, as such, allows for greater wetting of the composite surface with consequent higher rate of metal ion release .
  • a further added benefit of rendering the surface of the composite more hydrophilic, is that it may enhance osseocompatibility of the surface.
  • PEEK is hydrophobic and inert and does not interact well with bone.
  • a fibrous layer of tissue typically forms around the surface of plain PEEK implants, which prevents osseointegration and may facilitate future biofilm formation at the PEEK fibrous tissue interface.
  • PEEK metal zeolites in contrast to PEEK implants devoid of metal, carry significant charged particles at the surface. When acid etched to a hydrophilic state, they readily interact with osteoblasts and other proteins and cells which are crucial to osteointegration and bone healing .
  • Embodiments disclosed herein include imparting antimicrobial properties to polymers using ceramics, preferably zeolites, as a cation cage, to deliver and dose one or more antimicrobial cations.
  • ceramics preferably zeolites, as a cation cage
  • other suitable ceramic antimicrobial materials include hydroxy apatite, zirconium phosphates and other ion- exchange ceramics.
  • Suitable cations include silver, copper, zinc, mercury, tin, lead, gold, bismuth, cadmium, chromium and thallium ions, and combinations thereof, with silver, zinc and/or copper being preferred.
  • Either natural zeolites or synthetic zeolites can be used to make the zeolites used in the embodiments disclosed herein.
  • Zerolite is an aluminosilicate having a three dimensional skeletal structure that is represented by the formula: ⁇ 2 / ⁇ ⁇ AI 2 O 3 ⁇ YS1O 2 ⁇ Z3 ⁇ 40 wherein M represents an ion- exchangeable ion, generally a monovalent or divalent metal ion, n represents the atomic valency of the (metal) ion, X and Y represent coefficients of metal oxide and silica respectively, and Z represents the number of water of crystallization.
  • Examples of such zeolites include A-type zeolites, X-type zeolites, Y-type zeolites, T-type zeolites, high-silica zeolites, sodalite, and others.
  • silicate materials such as metal doped phosphate glass, bioactive glass such as 45S5 and BG can be processed to deliver a suitable dose of antimicrobial cations .
  • the polymer containing the antimicrobial metal ions is contacted with a strong acid or a suitable solvent, such as by immersion, dipping, spraying, etc. After contacting with the acid for a sufficient amount of time, the article can be washed and further processed in a conventional manner.
  • Suitable polymers include thermoplastic resins, especially polyaryletherketones such as polyetheretherketone (PEEK) and polyetherketoneketone (PEKK) .
  • Suitable acids include sulfuric acid, nitric acid, mixtures thereof, glacial acetic acid, citric acid solution, and phosphoric acid, particularly in combination with nitric and sulfuric acid.
  • the acid is concentrated sulfuric acid, e.g., an aqueous solution containing at least 90% sulfuric acid, more preferably at least 95% sulfuric acid, even more preferably at least 98% sulfuric acid.
  • the acid is nitric acid, such as 70% nitric acid, or fuming nitric acid (>86% nitric acid) .
  • Sulfuric acid actually gradually dissolves the surface of the PEEK and, given time, may dissolve the whole material coupon.
  • a clear liquid resin solution appears on the surface of the coupon, when the coupon is removed from the acid and immersed in water it condenses to a solid white surface layer.
  • Concentrated nitric acid can, under certain conditions, nitrate parts of the PEEK polymer.
  • PEEK metal zeolite composites were immersed in concentrated nitric acid, no apparent visual change took place.
  • the rate of release of metal ions was found to be significantly increased. The degree of increase in rate was found to be dependent on acid concentration, agitation rate and time of exposure to acid .
  • the metal-containing polymer is contacted with a suitable organic solvent. Suitable organic solvents include those having some degree of polarity and boiling points ranging from about 175°C to about 380°C, especially above about 240°C to about 300°C.
  • Suitable solvents include benzophenone, - chloronaphthalene, diphenylsulfone, 2-phenylphenol, p- methoxyphenol , 2-methoxynaphthalene, ethyl-r- hydroxybenzoate, N-cyclohexyl-2 -pyrrolidone, pentafluorophenol , dimethylphthalate, and phenylbenzoate .
  • the polymer can be contacted, such as by immersion or soaking, with a cleaning agent such as propanol or acetone to remove any oily residues from the cutting procedure, prior to contacting the polymer with the acid or organic solvent.
  • a cleaning agent such as propanol or acetone
  • Samples of PEEK rod of 25mm diameter, compounded with 8% silver zeolite which contained about 20% (w/w) silver were sliced into fine discs of about 2 sq. inch surface area. Samples were immersed in acids to determine if the silver release rates would be affected. Sample 1 was immersed in 98 "6 sulfuric acid for about 3 minutes. The sample, which was initially chocolate colored, turned white to light grey when rinsed in water.
  • Sample 2 was immersed in 98 "6 sulfuric acid for about 3 minutes and a small amount of water was added to the concentrated acid. The solution became hot and the sample changed color as before to a whitish color.
  • Sample 3 was immersed in fuming nitric acid for about 5 minutes. This sample retained its chocolate color after rinsing and no changes in appearance were visible after treatment .
  • sample 4 was a sample of the PEEK/ silver zeolite composite which was not acid etched.
  • the 715 four hour actual eluted silver shown in the last entry above would be about 942 ppb (rather than 715 ppb) , so the concentration is not actually decreasing.
  • the data presented is the actual measured concentration in the petri dish. The data show that propanol is a more effective cleaning solution than acetone in this case, and there is a three to four-fold enhancement of silver release rate at one hour due to nitric acid etching. At 30 minutes etching the enhancement of release rate is nearly 9 fold after 4 hours.
  • Samples (two for each etch time) of 25 mm diameter PEEK/silver composite disks were placed in Nalgene bottles of 250 ml capacity with sealing caps, and 50 ml of 70% nitric acid added to each.
  • the bottles were placed on a Labline thermal rocker and allowed to roll back and forth on the rocker at a rate of 30 cycles per minute for the allotted time. This procedure causes consistent strong agitation while keeping the acid enclosed.
  • the acid was poured from the bottle and purified water immediately added.
  • the rinse water was changed several times until all traces of acid were removed from the sample.
  • the individual samples were placed in petri dishes and 50 ml of sodium nitrate solution added.
  • the samples were placed in petri dishes and 50 ml of sodium nitrate solution (0.8-1%) was added.
  • the petri dishes were rocked on a Labline rocker at 30 cycles per minute .

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Transplantation (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Molecular Biology (AREA)
  • Dental Preparations (AREA)

Abstract

L'invention concerne des procédés pour conférer des propriétés antimicrobiennes à des polymères à l'aide de céramiques, de préférence de zéolites, comme cage cationique, pour administrer et doser un ou plusieurs cations antimicrobiens. Un polymère contenant des ions métalliques antimicrobiens est mis en contact avec un acide fort ou un solvant approprié, tel que par immersion, trempage, pulvérisation, etc. Après la mise en contact avec l'acide pendant une quantité suffisante de temps, l'article peut être lavé et encore traité d'une manière classique. Les polymères appropriés comprennent les résines thermoplastiques, notamment les polyaryléthercétones telles que la polyétheréthercétone (PEEK) et la polyéthercétonecétone (PEKK). Les acides appropriés comprennent l'acide sulfurique, l'acide nitrique, leurs mélanges, l'acide acétique glacial, une solution d'acide citrique, et l'acide phosphorique, en particulier en combinaison avec l'acide nitrique et l'acide sulfurique.
PCT/US2014/027576 2013-03-15 2014-03-14 Implants orthopédiques à auto-stérilisation à efficacité améliorée WO2014152649A1 (fr)

Applications Claiming Priority (2)

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US201361791360P 2013-03-15 2013-03-15
US61/791,360 2013-03-15

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9107765B2 (en) 2010-05-07 2015-08-18 Difusion Technologies, Inc. Medical implants with increased hydrophilicity
US9132576B2 (en) 2009-12-11 2015-09-15 Difusion Technologies, Inc. Method of manufacturing antimicrobial implants of polyetheretherketone
US9492584B2 (en) 2009-11-25 2016-11-15 Difusion Technologies, Inc. Post-charging of zeolite doped plastics with antimicrobial metal ions
CN111116964A (zh) * 2019-12-17 2020-05-08 上海交通大学医学院附属仁济医院 生物功能化表面改性的聚醚醚酮材料及其制备方法与应用
WO2024002804A1 (fr) * 2022-06-29 2024-01-04 Gehr-Kunststoff-Extrusionsgesellschaft mbH Substrat thermoplastique antibactérien

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030031687A1 (en) * 2001-01-04 2003-02-13 Byotrol Llc Anti-microbial composition
US20050170070A1 (en) * 2001-01-30 2005-08-04 Isotis S.A. Method for applying a bioactive coating on a medical device
US20100215643A1 (en) * 2009-02-25 2010-08-26 Orthobond Corp. Anti-infective functionalized surfaces and methods of making same
US20120315340A1 (en) * 2009-11-25 2012-12-13 Difusion Technologies, Inc. Post-Charging Of Zeolite Doped Plastics With Antimicrobial Metal Ions

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030031687A1 (en) * 2001-01-04 2003-02-13 Byotrol Llc Anti-microbial composition
US20050170070A1 (en) * 2001-01-30 2005-08-04 Isotis S.A. Method for applying a bioactive coating on a medical device
US20100215643A1 (en) * 2009-02-25 2010-08-26 Orthobond Corp. Anti-infective functionalized surfaces and methods of making same
US20120315340A1 (en) * 2009-11-25 2012-12-13 Difusion Technologies, Inc. Post-Charging Of Zeolite Doped Plastics With Antimicrobial Metal Ions

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9492584B2 (en) 2009-11-25 2016-11-15 Difusion Technologies, Inc. Post-charging of zeolite doped plastics with antimicrobial metal ions
US9132576B2 (en) 2009-12-11 2015-09-15 Difusion Technologies, Inc. Method of manufacturing antimicrobial implants of polyetheretherketone
US9107765B2 (en) 2010-05-07 2015-08-18 Difusion Technologies, Inc. Medical implants with increased hydrophilicity
US9375321B2 (en) 2010-05-07 2016-06-28 Difusion Technologies, Inc. Medical implants with increased hydrophilicity
CN111116964A (zh) * 2019-12-17 2020-05-08 上海交通大学医学院附属仁济医院 生物功能化表面改性的聚醚醚酮材料及其制备方法与应用
WO2024002804A1 (fr) * 2022-06-29 2024-01-04 Gehr-Kunststoff-Extrusionsgesellschaft mbH Substrat thermoplastique antibactérien

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