CA2386765A1 - Nitric oxide-modified linear poly(ethylenimine) fibers and uses therefor - Google Patents

Nitric oxide-modified linear poly(ethylenimine) fibers and uses therefor Download PDF

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Publication number
CA2386765A1
CA2386765A1 CA002386765A CA2386765A CA2386765A1 CA 2386765 A1 CA2386765 A1 CA 2386765A1 CA 002386765 A CA002386765 A CA 002386765A CA 2386765 A CA2386765 A CA 2386765A CA 2386765 A1 CA2386765 A1 CA 2386765A1
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Prior art keywords
nanofiber
ethylenimine
linear poly
medical device
diazeniumdiolate
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CA002386765A
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French (fr)
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CA2386765C (en
Inventor
Daniel Smith
Darrell Reneker
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University of Akron
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Classifications

    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/96—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from other synthetic polymers
    • 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
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
    • A61L15/26—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds; 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
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/44—Medicaments
    • 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
    • A61L17/00—Materials for surgical sutures or for ligaturing blood vessels ; Materials for prostheses or catheters
    • A61L17/14—Post-treatment to improve physical properties
    • A61L17/145—Coating
    • 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
    • A61L27/28—Materials for coating prostheses
    • A61L27/34—Macromolecular 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
    • A61L27/54—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
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/08—Materials for coatings
    • A61L29/085—Macromolecular 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
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/14—Materials characterised by their function or physical properties, e.g. lubricating compositions
    • A61L29/16—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
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/08—Materials for coatings
    • A61L31/10—Macromolecular 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
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L31/16—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
    • 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
    • A61L2300/114—Nitric oxide, i.e. NO
    • 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
    • A61L2300/606—Coatings
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S623/00—Prosthesis, i.e. artificial body members, parts thereof, or aids and accessories therefor
    • Y10S623/924—Material characteristic
    • Y10S623/926—Synthetic
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S977/00—Nanotechnology
    • Y10S977/84—Manufacture, treatment, or detection of nanostructure
    • Y10S977/89—Deposition of materials, e.g. coating, cvd, or ald
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
    • Y10T428/2991—Coated
    • Y10T428/2998—Coated including synthetic resin or polymer

Abstract

A novel coating for medical devices provides nitric oxide delivery using nanofibers of linear poly(ethylenimine)diazeniumdiolate. Linear poly(ethylenimine)diazeniumdiolate releases nitric oxide (NO) in a controlle d manner to tissues and organs to aid the healing process and to prevent injur y to tissues at risk of injury. Electrospun nanofibers of linear poly(ethylenimine)diazeniumdiolate deliver therapeutic levels of NO to the tissues surrounding a medical device while minimizing the alteration of the properties of the device. A nanofiber coating, because of the small size and large surface area per unit mass of the nanofibers, provides a much larger surface area per unit mass while minimizing changes in other properties of t he device.

Claims (9)

1. A medical device comprising at least one nanofiber of a polymeric linear poly(ethylenimine) diazeniumdiolate, said at least one nanofiber forming a coating layer on the device
2. The device of claim 1, wherein said at least one nanofiber is insoluble ~n aqueous solutions.
3. The device of claim 2, wherein the medical device is a vascular graft, a stent, a catheter, a wound dressing, or surgical thread.
4. The device of claim 2, wherein the at least one linear polyethylenimine diazeniumdiolate nanofiber has a diameter of between about 100 near meters and about 5 microns
5 The device of claim 2, wherein the at least one linear polyethylenimine diazeniumdiolate nanofiber has a diameter of between about 100 nanometers and about 1 micron.
6. The device of claim 5, wherein the at least one linear polyethylenimine diazeniumdiolate nanofiber has a diameter of between about 100 nanometers and about 400 nanometers.
7 The device of claim 1, wherein the at least one nanofiber is formed by electrospinning.
8 The device of claim 1, wherein the medical device is a vascular gr~ft, a stent, a catheter, a wound dressing, or surgical thread.
9. A method of making a medical device, comprising the steps of:
(a) providing a solution of linear poly(ethylenimine) in an organic solvent and an untreated medical device;
(b) subjecting the linear poly(ethylenimine) solution to an electric field such that at least one nanofiber is produced;
(c) depositing the at least one nanofiber onto a medical device such that a nanofiber coated medical device is produced The method of claim 9, comprising the additional step of exposing the linear poly(ethylenimine) to nitric oxide such that a linear poly(ethylenimine) diazeniumdiolate is produced, wherein said additional step takes place prior to the step of subjecting the linear poly(ethylenimine) to an electric field 11. The method of claim 10, additionally comprising the step of crosslinking the at least one nanofiber of linear poly(ethylenimine) diazeniumdiolate of the nanot ber coated medical device 12. The method of claim 11, wherein the step of crosslinking comprises treating the at least one nanofiber of linear poly(ethylenimine) diazemumdiolate with 1, butanediol diglycidyl ether is tetrahydofuran solvent and curing the at least one nanofiber by heating to about 80°C for at least about 30 minutes.
13. The method of claim 9, additionally comprising the step of crosslinking the at least one nanofiber of linear poly(ethylenimine) of the nanofiber coated medical device.
14. The method of claim 13, additionally comprising the step of treating the crosslinked at least one nanofiber of linear poly(ethylenimine) with nitric oxi~e to create crosslinked nanofibers of linear poly(ethylenimine) diazeniumdiolate 15. The method of claim 9, whereon the linear poly(ethylenimine) solution subjected to an electric field additionally comprises a crosslinking agent, and further comprising the step of curing the resulting at least one nanofiber of the nanofiber c~ated medical device, such that the at least one nanofiber is crosslinked.

16. The method of claim 15, further comprising the step of treating the at least one crosslinked linear poly(ethylenimine) nanofibers with nitric oxide such that a ~ least one linear poly(ethylenimine) diazeniumdiolate nanofiber is produced 17 The method of claim 9, additionally comprising the step of treating the a~
least one linear poly(ethylenimine) nanofiber of the nanofiber coated medical device with nitric oxide such that at least one linear poly(ethylenimine) diazeniumdiolate nanofiber is produced.
18. The method of claim 17, additionally comprising the step of crosslinking he at least one linear poly(ethylenimine) diazemiumdiolate nanofiber 19 A method of using a medical device comprising the steps of:
a) providing a medical device which is coated with at least one nanofiber of linear poly(ethylenimine) diazeniumdiolate;
b) using the medical device in the medical treatment of a mammal.
20. The method of claim l9, wherein the medical device is selected from the group consisting of a vascular graft, a stent, a catheter, a wound dressing, and surgical thread.
21. The method of claim 19, wherein the at least one nanofiber of linear poly(ethylenimine) diazeniumdiolate is crosslinked.
CA2386765A 1999-10-08 2000-10-06 Nitric oxide-modified linear poly(ethylenimine) fibers and uses therefor Expired - Fee Related CA2386765C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US15867399P 1999-10-08 1999-10-08
US60/158,673 1999-10-08
US09/571,444 US6737447B1 (en) 1999-10-08 2000-05-16 Nitric oxide-modified linear poly(ethylenimine) fibers and uses thereof
US09/571,444 2000-05-16
PCT/US2000/027769 WO2001026702A2 (en) 1999-10-08 2000-10-06 Nitric oxide-modified linear poly(ethylenimine) fibers and uses therefor

Publications (2)

Publication Number Publication Date
CA2386765A1 true CA2386765A1 (en) 2001-04-19
CA2386765C CA2386765C (en) 2011-12-20

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CA2386765A Expired - Fee Related CA2386765C (en) 1999-10-08 2000-10-06 Nitric oxide-modified linear poly(ethylenimine) fibers and uses therefor

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US (2) US6737447B1 (en)
EP (1) EP1220694B1 (en)
AT (1) ATE237372T1 (en)
AU (1) AU8000600A (en)
CA (1) CA2386765C (en)
DE (1) DE60002227T2 (en)
DK (1) DK1220694T3 (en)
WO (1) WO2001026702A2 (en)

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