WO1999001167A1 - Process for modifiying surfaces using the reaction product of a water-insoluble polymer and a polyalklene imine - Google Patents
Process for modifiying surfaces using the reaction product of a water-insoluble polymer and a polyalklene imine Download PDFInfo
- Publication number
- WO1999001167A1 WO1999001167A1 PCT/US1997/020055 US9720055W WO9901167A1 WO 1999001167 A1 WO1999001167 A1 WO 1999001167A1 US 9720055 W US9720055 W US 9720055W WO 9901167 A1 WO9901167 A1 WO 9901167A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- biologically active
- active agent
- imine
- reaction product
- article
- Prior art date
Links
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
- A61L33/00—Antithrombogenic treatment of surgical articles, e.g. sutures, catheters, prostheses, or of articles for the manipulation or conditioning of blood; Materials for such treatment
- A61L33/0005—Use of materials characterised by their function or physical properties
- A61L33/0011—Anticoagulant, e.g. heparin, platelet aggregation inhibitor, fibrinolytic agent, other than enzymes, attached to the substrate
- A61L33/0029—Anticoagulant, e.g. heparin, platelet aggregation inhibitor, fibrinolytic agent, other than enzymes, attached to the substrate using an intermediate layer of polymer
-
- 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
- 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
- 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
-
- 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
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31909—Next to second addition polymer from unsaturated monomers
Definitions
- the invention relates to modifying the surface of an article.
- Surfaces of, e.g., medical devices must often be modified.
- the surfaces of medical devices that are in direct contact with blood or blood products e.g., blood oxygenators, blood pumps, catheters, and tubing
- biologically active agents such as heparin or derivatives thereof to make such surfaces nonthrombogenic in an effort to prevent clotting or clot formation related to surface contact with blood or blood products.
- the invention features a process for modifying the surface of an article that includes treating the surface with a solution that includes (a) an organic solvent, and (b) the reaction product of a substantially water insoluble polymer and a polyalkylene imine (e.g., polyethylene imine) to form a modified surface.
- a solution that includes (a) an organic solvent, and (b) the reaction product of a substantially water insoluble polymer and a polyalkylene imine (e.g., polyethylene imine) to form a modified surface.
- the treated surface may be reacted further with a biologically active agent.
- the biologically active agent may include negatively charged materials.
- biologically active agents include anti-thrombotic agents (e.g., a glycosaminoglycan (or a derivative thereof) such as heparin or a heparin derivative).
- suitable biologically active agents include heparin sulfate, hyaluronic acid, dermatan sulfate, chitosan, derivatives thereof, and combinations thereof.
- Preferred substantially water-insoluble polymers include functional groups such as ester groups that are capable of forming a covalent bond with the polyalkylene imine.
- Specific examples include the reaction product of an alkyl acrylate and an alkyl methacrylate (e.g., isooctyl acrylate and methyl methacrylate); the reaction product of an alkyl methacrylate, an alkylacrylate, and N-vinyl pyrrolidone (e.g., methyl methacrylate, isooctyl acrylate, and N-vinyl pyrrolidone); and the reaction product of an alkyl acrylate, an alkyl methacrylate, and a hydroxyalkyl methacrylate (e.g., isooctyl acrylate, methyl methacrylate, and hydroxypropyl methacrylate).
- the acrylate, methacrylate, and N-vinyl pyrrolidone may be provided in the form
- the invention also features an article that includes a substrate having a modified surface that includes the reaction product of a substantially water insoluble polymer and a polyalkylene imine.
- the article may further include a biologically active agent bound to the surface.
- a “biologically active agent” is a material which, when in contact with a patient's blood, plasma, or other body fluids or tissues under physiological conditions, exhibits biological activity.
- a material such as heparin is “biologically active” in the sense that it acts as an anti-coagulant in the presence of blood.
- the invention provides a simple and effective means for modifying the surface of an article, e.g., such that when in contact with a patient's blood, plasma, or other body fluids, the surface does not cause an adverse physiological reaction.
- the present invention provides a process for producing modified surfaces (e.g., the surfaces of medical devices such as filters, membranes, tubes, catheters, oxygenator, intravascular probes, blood pumps, blood gas sensing devices, and the like).
- the surface may be a polymer, ceramic, or metal surface.
- suitable polymer surfaces include polypropylene, poly (vinyl chloride), poly (methyl methacrylate), polytetrafluoroethylene, polysulfone, silicone rubber, poly (ethylene terephthalate), polycarbonate, polyethylene, polystyrene, and polyurethane.
- the surface is contacted with a priming solution that contains an organic solvent and the reaction product of a polyalkylene imine, such as polyethylene imine, and a substantially water insoluble polymer, and then dried.
- a priming solution that contains an organic solvent and the reaction product of a polyalkylene imine, such as polyethylene imine, and a substantially water insoluble polymer, and then dried.
- the resulting primed surface is capable of binding with a biologically active agent.
- the system is designed to be functional after a single coating step, the solution may be coated on the surface and dried as many times as is necessary to achieve the desired concentration of functional groups on the surface. The particular amount of coating and concentration of functional groups on the surface will depend upon the particular application for which the treated surface is intended.
- the surface may then be contacted with a biologically active agent to bind the biologically active agent to the primed surface.
- the biologically active agent may be an anti-thrombotic agent (e.g., a glycosaminoglycan (or derivative thereof) such as heparin or a heparin derivative), an anti-microbial agent, a therapeutic agent (e.g., a drug or growth factor), an enzyme, or a cell attachment protein.
- suitable biologically active agents include heparin, heparan sulfate, hyaluronic acid, dermatan sulfate, chitosan, and derivatives thereof. The agents may be used alone or in combination with each other.
- Binding may be either ionic or covalent, with covalent being preferred.
- the biologically active agent include one or more negatively charged groups.
- the biologically active agent may then be treated with a crosslinking agent, if desired.
- covalent binding it is preferred to contact the primed surface with a biologically active agent having free aldehyde groups (generated, e.g., by periodate oxidation) in the presence of a reducing agent such as sodium cyanoborohydride.
- a biologically active agent having free aldehyde groups generated, e.g., by periodate oxidation
- a reducing agent such as sodium cyanoborohydride.
- the covalent binding most likely occurs via formation of a Schiff s base initially, which is then readily reduced to a secondary amine in the presence of the sodium cyanoborohydride.
- Covalent binding may also be accomplished using a coupling agent such as a carbodiimide, rather than sodium cyanoborohydride.
- a coupling agent such as a carbodiimide, rather than sodium cyanoborohydride.
- the covalent linkage occurs between carboxylate groups on the biologically active agent and amine groups on the primed surface.
- Preferred priming solutions include between about 0.1 to about 20% solids in a solution that includes between about 50 and about 99.9% organic solvent and up to about 50% water.
- the weight to weight ratio of substantially water insoluble polymer to polyethylene imine is preferably between about 0.1 : 1 and about 10:1, more preferably about 4 : 1.
- Suitable polyalkylene imines are those having an average molecular weight of between about 300 and 1,000,000.
- a suitable polyalkylene imine is polyethylene imine having an average molecular weight of 750,000, available from the Aldrich Chemical Co., Milwaukee, Wisconsin.
- Preferred substantially water insoluble polymers are those polymers that provide functional groups capable of forming a covalent bond with the amine groups of the polyalkylene imine while not interfering with the ability of the polyalkylene imine to bind to a biologically active agent.
- the polymer preferably is soluble in those organic solvents in which the polyalkylene imine is soluble.
- Suitable substantially water insoluble polymers include substantially water insoluble acrylate polymers such as, e.g., alkyl acrylate-alkyl methacrylate copolymers (e.g., copolymers of isooctyl acrylate and methyl methacrylate), alkyl methacrylate-alkyl acrylate-N-vinyl pyrrolidone terpolymers (e.g., methyl methacrylate-isooctyl acrylate-N-vinyl pyrrolidone), and alkyl acrylate-alkyl methacrylate-hydroxyalkyl methacrylate terpolymers (e.g., isooctyl acrylate-methyl methacrylate-hydroxypropyl methacrylate).
- alkyl acrylate-alkyl methacrylate copolymers e.g., copolymers of isooctyl acrylate and methyl methacrylate
- Preferred organic solvents are those capable of dissolving both the substantially water insoluble polymer and polyalkylene imine, and rapidly evaporating after the application of the priming solution to the substrate surface.
- Suitable organic solvents include tetrahydrofuran and alkyl alcohols such as, e.g., methanol, ethanol, and isopropyl alcohol.
- Methyl methacrylate monomers, isooctyl acrylate monomers and N-vinyl pyrrolidone monomers were polymerized as described in Examples 2-8, formulation D of U.S. Patent No. 4,584, 192, to form a terpolymer.
- the terpolymer was then repeatedly washed and distilled so as to remove the acetone. Once the acetone was removed, the terpolymer was placed in isopropyl alcohol.
- the terpolymer solution and polyethylene imine were then placed in a solution of isopropyl alcohol and water.
- the resulting solution contained 4: 1 polyethylene imine/terpolymer, 2.5% solids solution in 82.5% isopropyl alcohol and 15% water.
- the solution was allowed to react for four hours at 50EC, after which it was coated on a piece of woven polyester. After evaporation of the solvent, a portion of the sample was separated and rinsed with water. It was then stained with 8-hydroxy-7-(4-sulfo-l-naphthylazo)-5-quinoline sulfonic acid (SNAZOXS), which revealed the presence of PEI.
- SNAZOXS 8-hydroxy-7-(4-sulfo-l-naphthylazo)-5-quinoline sulfonic acid
- the remaining portion of the sample was rinsed with 25% saline solution and then stained with SNAZOXS. Staining also revealed the presence of PEI, demonstrating that the PEI does not rinse off even with saline solution.
- IOA/MMA/hydroxypropyl methacrylate (HPMA) terpolymer having 50 parts IOA, 40 parts MMA and 10 parts HPMA, was dissolved in 35g of THF.
- PEI was added to the IOA/MMA/HPMA THF solution and the mixture was allowed to react for four hours at 50EC.
- the solution was coated on a piece of woven polyester. After evaporation of the solvent, the polyester sample was rinsed with a 25% saline solution. The polyester sample was then stained with SNAZOXS, which revealed the presence of PEI.
- the heparinized sample was then rinsed for five minutes in 25% saline solution to remove ionically bound heparin, leaving only covalently bound heparin.
- the sample was subjected to a thrombin inhibition assay following the procedure described in Sirvio et al., U.S. Patent No. 5,532,311 (hereby incorporated by reference). The results of the assay demonstrated that the activity of heparin on the sample surface corresponded to 0.14 micrograms/cm 2 .
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP97946507A EP1021216A1 (en) | 1997-07-01 | 1997-10-31 | Process for modifiying surfaces using the reaction product of a water-insoluble polymer and a polyalklene imine |
AU51662/98A AU5166298A (en) | 1997-07-01 | 1997-10-31 | Process for modifiying surfaces using the reaction product of a water-insoluble polymer and a polyalklene imine |
JP50860499A JP4339413B2 (en) | 1997-07-01 | 1997-10-31 | Surface modification method using reaction mixture of water-insoluble polymer and polyalkylenimine |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/886,720 US6146771A (en) | 1997-07-01 | 1997-07-01 | Process for modifying surfaces using the reaction product of a water-insoluble polymer and a polyalkylene imine |
US08/886,720 | 1997-07-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1999001167A1 true WO1999001167A1 (en) | 1999-01-14 |
Family
ID=25389614
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1997/020055 WO1999001167A1 (en) | 1997-07-01 | 1997-10-31 | Process for modifiying surfaces using the reaction product of a water-insoluble polymer and a polyalklene imine |
Country Status (5)
Country | Link |
---|---|
US (1) | US6146771A (en) |
EP (1) | EP1021216A1 (en) |
JP (1) | JP4339413B2 (en) |
AU (1) | AU5166298A (en) |
WO (1) | WO1999001167A1 (en) |
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WO2000027444A1 (en) * | 1998-11-09 | 2000-05-18 | Ecole Polytechnique Federale De Lausanne | Functionalised polymers for tissue engineering |
WO2000041739A1 (en) * | 1999-01-15 | 2000-07-20 | University Of Utah Research Foundation | Attachment of acid moiety-containing biomolecules to activated polymeric surfaces |
EP1088564A1 (en) * | 1999-09-30 | 2001-04-04 | Orbus Medical Technologies, Inc. | Intraluminal device, coating for such device, as well as a method for preparing the intraluminal device |
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US20030069601A1 (en) * | 1998-12-15 | 2003-04-10 | Closys Corporation | Clotting cascade initiating apparatus and methods of use |
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US8053078B2 (en) | 2005-04-11 | 2011-11-08 | Abbott Medical Optics Inc. | Medical devices having soft, flexible lubricious coatings |
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WO2000027444A1 (en) * | 1998-11-09 | 2000-05-18 | Ecole Polytechnique Federale De Lausanne | Functionalised polymers for tissue engineering |
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WO2001023016A1 (en) * | 1999-09-30 | 2001-04-05 | Orbus Medical Technologies Inc. | Intraluminal device, coating for such device, and method for preparing said device |
US7955612B1 (en) | 1999-09-30 | 2011-06-07 | Orbusneich Medical, Inc. | Intraluminal device, coating for such device, and method for preparing said device |
Also Published As
Publication number | Publication date |
---|---|
JP4339413B2 (en) | 2009-10-07 |
EP1021216A1 (en) | 2000-07-26 |
US6146771A (en) | 2000-11-14 |
JP2002514126A (en) | 2002-05-14 |
AU5166298A (en) | 1999-01-25 |
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