WO1996040187A1 - Surface-modifying copolymers having cell adhesion properties - Google Patents
Surface-modifying copolymers having cell adhesion properties Download PDFInfo
- Publication number
- WO1996040187A1 WO1996040187A1 PCT/US1996/007500 US9607500W WO9640187A1 WO 1996040187 A1 WO1996040187 A1 WO 1996040187A1 US 9607500 W US9607500 W US 9607500W WO 9640187 A1 WO9640187 A1 WO 9640187A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- poly
- additive
- urethane
- modifying
- gly
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/78—Connective tissue peptides, e.g. collagen, elastin, laminin, fibronectin, vitronectin, cold insoluble globulin [CIG]
-
- 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
- A61L33/0076—Chemical modification of the substrate
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/745—Blood coagulation or fibrinolysis factors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/458—Block-or graft-polymers containing polysiloxane sequences containing polyurethane sequences
Definitions
- the present invention is directed to novel block copolymers which are hemocompatible surface-modifying additives for modifying polyurethane, poly (urethane urea), polystyrene or polystyrene-containing elastomer substrates.
- Cell adhesion to natural or synthetic substrates is mediated by the interaction of cell adhesion proteins which correspondingly accommodate cell surface receptors.
- Cell adhesion proteins are exemplified by fibronectin,
- RGDS is one of the sequences found in fibronectin, fibrinogen and von Willebrand factor which aids adhesion to cells.
- Fibronectin also contains RGDX-like adhesion sequences such as REDV (Arg-Glu-Asp-Val).
- Biomaterial surfaces comprising either hydrophilic (e.g., polyethylene oxide) or extremely hydrophobic (e.g.,
- polydimethylsiloxane are known in medical devices and are the subject of ongoing investigation for such cardiovascular applications, but such biomaterials are not as
- the present invention provides nonpolar
- polydimethylsiloxane blocks incorporated into a block copolymer onto which is covalently linked a particular chemical sequence for increased cell adhesion.
- the nonpolar polydimethylsiloxane blocks selectively segregate toward the air interface of the substrate polymer surface as a result of the thermodynamic driving force to minimize surface free energy.
- the cell adhesion sequence covalently linked thereto will also be pulled toward the surface of the polymer films by virtue of the fact that they are covalently bound to the polydimethylsiloxane.
- the copolymers can either be blended with substrate polymers in low amounts, coated onto substrate polymers in low amounts, or covalently attached to the substrate polymers. When placed in contact with blood, the cell adhesion amino acid sequences will rise to the surface in the hydrophilic environment, and
- endothelial tissue unique to the individual in which the device is implanted will grow over the
- biomaterial surface and blood will not coagulate on this surface. Since only the surface of the biomaterial will expose the polydimethylsiloxane-amino acid copolymers, a variety of bulk polymeric substrates may be used which have a wide range of mechanical and morphological properties.
- the copolymers of the present invention will comprise at least three blocks or segments, each with a specific function, that is, an anchor block, a surface active block and the amino acid sequence. There may be an optional short hydrophilic spacer between the hydrophobic polydimethylsiloxane surface active block and the amino acid sequence.
- the function of the anchor block will be to provide the ability to form a film so that the copolymer will not be extracted from the biomaterial surface in the presence of blood, and to provide compatibility with the bulk material. This is an important feature in view of regulatory concerns.
- the anchor block must be chemically compatible with the bulk of the biomaterial substrate.
- copolymers with polystyrene anchor blocks will be suitable for blending with or coating onto polystyrene, polystyrene containing elastomers, or polyphenylene oxide.
- Copolymers containing either polyurethane or polyurea segments would be suitable for blending with polyurethane, polyurea, or poly (urethane-urea) bulk materials.
- a short, hydrophilic, spacer such as poly (2- ethyloxazoline) or poly (ethylene oxide) can be inserted between the polydimethylsiloxane and the amino acid
- segment By the term block it is meant that there is one type of recurring unit .
- block is a generic term, the term “segment” is sometimes used in the art to represent a relatively short length of repeating units, e.g., less than about ten monomeric units, but preferably less than 3 monomeric units, typically
- Block copolymers or segmented copolymers are composed of at least two blocks, one block composed of one type of recurring unit and at least one other block composed of a different type of recurring unit.
- Block copolymers as defined herein may be linear, cyclic or branched (cross- linked) structures.
- the preferred block copolymers in accordance with the present invention are linear.
- the block copolymers according to the present invention are hemo-compatible surface-modifying copolymer additives having the formulas:
- A is a poly (urethane), poly (urethane-urea), or polystyrene hard block
- B is a polysiloxane hydrophobic soft-block
- C is an optional hydrophilic spacer
- D is peptide sequence selected from the group consisting of:
- X and X' are any amino acid; and each n, v, m, and p is independently an integer greater than 0 up to about 500.
- the preferred amino acid for X and X' is Gly.
- the hard block (A) need not be a poly (urethane) or poly (urethane urea), as long as it is a hard block which is thermodynamically miscible with a poly (urethane), or poly
- the hard block need not be a Polystyrene, as long as it is a hard block which is miscible with a polystyrene or polystyrene-containing base polymer.
- Copolymers containing the anchor block and the surface-active block can be made in a variety of ways.
- the anchor block is polystyrene an activated terminus polystyrene may be prepared and then reacted with a cyclic siloxane to produce a copolymer of the anchor block (polystyrene) and the surface active block (polysiloxane) .
- the copolymer can then be reacted with an amino acid sequence.
- the polystyrene polysiloxane copolymer can be end-capped with activated ethyloxazoline groups for reaction with the peptide.
- the methylene chloride-terminated polystyrene polysiloxane copolymer is treated with ethyloxazoline to make the ethyloxazoline-terminated intermediates, which after treatment with the peptide GRGD, results in the peptide-terminated copolymer.
- hydroxy functional dimethylsiloxane end-blocking reagents may be prepared whereby the molecular weight of polydimethylsiloxane oligomers can be controlled by synthetic conditions.
- polysiloxane-urethane blocked polymers may be prepared modified with appended peptide moieties (such as RGD) which are covalently linked to the polysiloxane portion of the chain via an arginine N- terminal.
- Cyclosiloxanes having functional substituents such as cyanopropyl in addition to methyl attached to the silicon atoms can be polymerized with the D 4 to prepare analogous siloxane oligomers with pendent functional groups along the oligomer backbone.
- the yield of the desired polymer is sensitive to the size of the substituent group on the silicon atoms in the siloxane system whereby the yield decreases for hydrogen, alkyl groups, and
- a polyurethane copolymer backbone with pendent benzyl butyrate substituents may be synthesized in a manner similar to the methods used for preparing block copolymers.
- Polysiloxane prepolymers may be end-capped by reaction with an excess of methylene diphenyldiisocyanate and then extended with 1, 4-butanediol.
- the benzyl esters may be removed by known methods, such as by hydrogenation. This is shown in scheme 5, below.
- the peptides containing the amino acid segments such as RGD may be prepared by known procedures such as that shown in scheme 6. h d
- amine terminus of these graft segments may be deblocked and the grafts bonded to the pendent carboxypropyl units on a block copolymer using dicyclohexyl carbodiimide as an activating agent as shown in scheme 7.
- Polyethylene oxide spacers can be added to the amine
- Scheme 9 Preparation of polyethylene oxide spacers with an amine terminus and with a carboxylic acid terminus.
- the starting material is preferrably the p-nitro-phenoxide salt.
- This oligomeric group may be appended to the carboxyl group on the siloxane portion of the copolymer by coupling the amine terminus to the PEO unit as shown in scheme 10.
- spacers may be utilized such as poly(aolkyloxazoline), polyacrylamides, polylvinylpyrrolidone).
- poly(aolkyloxazoline), polyacrylamides, polylvinylpyrrolidone) poly(aolkyloxazoline), polyacrylamides, polylvinylpyrrolidone).
- polyethylene oxide spacers or other polyalkylene oxide spacers are preferred since the binding strength to hydrogen bonding surfaces of ether oxygens is expected to be less than the binding strength of the amino bonds of the amino acid segments. Therefore, the polyethylene oxide spacers would not
- vinylacetic acid can either be coupled directly to benzylalcohol using known activating agents (e.g. dicyclohexylcarbodiimide), or it can first be converted to the corresponding acid chloride and
- this siloxane tetramer can then be equilibrated with D4 and siloxane hydroxy terminated monomers to form the hydroxy functional terminated polysiloxane oligomers with pendent protected carboxy groups.
- Scheme 6 there is shown a conventional Merrifield synthesis scheme for coupling amino acids to make the peptide RGD.
- Scheme 9 there is shown the preparation of polyethylene oxide spacers having an amine terminus and a carboxylic acid terminus.
- Scheme 7 there is shown the addition of the protected peptides to the carboxy terminal pendant groups of hydroxy functional polysiloxane oligomers and then removal of the protecting groups to form, in this case, a
- polymers according to the present invention are useful for surface modification of base polymers which are poly (urethane), poly (urethane-urea) s , polystyrenes or polystyrene-containing elastomers, to allow endothelial cell adhesion thereto, thereby forming endothelial monolayers which are nonthrombogenic.
- base polymers which are poly (urethane), poly (urethane-urea) s , polystyrenes or polystyrene-containing elastomers, to allow endothelial cell adhesion thereto, thereby forming endothelial monolayers which are nonthrombogenic.
- base polymers which are poly (urethane), poly (urethane-urea) s , polystyrenes or polystyrene-containing elastomers, to allow endothelial cell adhesion thereto, thereby forming endothelial monolayers which are nonthrombogenic.
- the base polymer modified according to the present invention may be used in blood-contacting devices, such as vascular
- prostheses in the venous or arterial system heart patches, heart valves, as the outer encapsulants of implantable devices such as pacemakers, catheters or the outer sheath of catheters in contact with body fluids, temporary coverings on open wounds.
- the surface may also be utilized in
- extracorporeal devices to provide channels through which body fluids may be passed in heart, lung and kidney
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP50068797A JP2001516228A (en) | 1995-06-07 | 1996-05-22 | Cell adhesive surface modified copolymer |
DE69612267T DE69612267T2 (en) | 1995-06-07 | 1996-05-22 | SURFACE MODIFYING COPOLYMERS HAVING CELL ADHESION PROPERTIES |
CA002197000A CA2197000C (en) | 1995-06-07 | 1996-05-22 | Surface-modifying copolymers having cell adhesion properties |
AU58025/96A AU5802596A (en) | 1995-06-07 | 1996-05-22 | Surface-modifying copolymers having cell adhesion properties |
EP96914755A EP0779815B1 (en) | 1995-06-07 | 1996-05-22 | Surface-modifying copolymers having cell adhesion properties |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/487,604 | 1995-06-07 | ||
US08/487,604 US5733538A (en) | 1995-06-07 | 1995-06-07 | Surface-modifying copolymers having cell adhesion properties |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1996040187A1 true WO1996040187A1 (en) | 1996-12-19 |
Family
ID=23936420
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1996/007500 WO1996040187A1 (en) | 1995-06-07 | 1996-05-22 | Surface-modifying copolymers having cell adhesion properties |
Country Status (8)
Country | Link |
---|---|
US (1) | US5733538A (en) |
EP (1) | EP0779815B1 (en) |
JP (1) | JP2001516228A (en) |
AU (1) | AU5802596A (en) |
CA (1) | CA2197000C (en) |
DE (1) | DE69612267T2 (en) |
ES (1) | ES2155188T3 (en) |
WO (1) | WO1996040187A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6262287B1 (en) * | 1997-05-15 | 2001-07-17 | Givaudan-Roure (International) Sa | Fragrance precursor compounds |
EP1959971A2 (en) * | 2005-12-08 | 2008-08-27 | The Polymer Technology Group, Inc. | Self-assembling monomers and oligomers as surface-modifying endgroups for polymers |
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US6548263B1 (en) | 1997-05-29 | 2003-04-15 | Cellomics, Inc. | Miniaturized cell array methods and apparatus for cell-based screening |
US6136872A (en) * | 1998-11-20 | 2000-10-24 | Shell Oil Company | Freeze-dried polystyrene-polysiloxane foams |
AUPQ100699A0 (en) | 1999-06-17 | 1999-07-08 | Northern Sydney Area Health Service | An assist device for the failing heart |
US6403063B1 (en) | 1999-07-26 | 2002-06-11 | Kenneth I. Sawyer | Method of treating nail fungus |
KR100312178B1 (en) * | 1999-10-06 | 2001-11-03 | 서경배 | the new amino acid silicon polymers, the method for producing them, the amino acid silicon polymer-suface treated cosmetic particles, and the cosmetic composition including the above particles |
US6942873B2 (en) | 2000-09-25 | 2005-09-13 | The Board Of Trustees Of The University Of Illinois | Microfabrication of membranes containing projections and grooves for growing cells |
AUPR333301A0 (en) * | 2001-02-23 | 2001-03-22 | Northern Sydney Area Health Service | Determining the volume of a normal heart and its pathological and treated variants by using dimension sensors |
US6783709B2 (en) * | 2002-07-10 | 2004-08-31 | The Regents Of The University Of California | Self-healing organosiloxane materials containing reversible and energy-dispersive crosslinking domains |
ATE374049T1 (en) * | 2002-08-13 | 2007-10-15 | Medtronic Inc | SYSTEM FOR DELIVERING ACTIVE INGREDIENTS WITH A HYDROPHOBIC CELLULOSE DERIVATIVE |
ATE459380T1 (en) * | 2002-08-13 | 2010-03-15 | Medtronic Inc | DOSAGE SYSTEMS OF ACTIVE INGREDIENTS WITH POLY(ETHYLENE-CO(METH)ACRYLATES, MEDICAL DEVICE AND METHOD |
WO2004014453A1 (en) * | 2002-08-13 | 2004-02-19 | Medtronic, Inc | Medical device exhibiting improved adhesion between polymeric coating and substrate |
EP1536846A1 (en) * | 2002-08-13 | 2005-06-08 | Medtronic, Inc. | Active agent delivery system including a polyurethane, medical device, and method |
AU2003258209A1 (en) * | 2002-08-13 | 2004-02-25 | Medtronic, Inc. | Active agent delivery systems, medical devices, and methods |
WO2004014448A1 (en) * | 2002-08-13 | 2004-02-19 | Medtronic, Inc. | Active agent delivery system including a hydrophilic polymer, medical device, and method |
GB0222522D0 (en) | 2002-09-27 | 2002-11-06 | Controlled Therapeutics Sct | Water-swellable polymers |
EP1684820A2 (en) * | 2003-08-13 | 2006-08-02 | Medtronic, Inc. | Active agent delivery systems including a miscible polymer blend, medical devices, and methods |
US20050095218A1 (en) * | 2003-10-29 | 2005-05-05 | The Procter & Gamble Company | Personal care composition containing a detersive surfactant, an antidandruff component, and ketoamide surfactants |
US8791073B2 (en) * | 2004-05-14 | 2014-07-29 | William Marsh Rice University | Peptide-modified polyurethane compositions and associated methods |
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US8084275B2 (en) * | 2005-02-08 | 2011-12-27 | Fujifilm Corporation | Magnetic composite body, production method thereof, method for removing substance with mannose on its surface, and method for concentrating substance with mannose on its surface |
JP2007040978A (en) * | 2005-06-30 | 2007-02-15 | Fujifilm Corp | Method for separating objective element using magnetic nanoparticles |
GB0613333D0 (en) | 2006-07-05 | 2006-08-16 | Controlled Therapeutics Sct | Hydrophilic polyurethane compositions |
GB0613638D0 (en) | 2006-07-08 | 2006-08-16 | Controlled Therapeutics Sct | Polyurethane elastomers |
GB0620685D0 (en) * | 2006-10-18 | 2006-11-29 | Controlled Therapeutics Sct | Bioresorbable polymers |
JP5062820B2 (en) * | 2007-03-23 | 2012-10-31 | 株式会社Adeka | Cyclic siloxane compound and positive resist composition using the same |
WO2013151755A1 (en) | 2012-04-04 | 2013-10-10 | University Of Washington Through Its Center For Commercialization | Systems and method for engineering muscle tissue |
EP2913067A4 (en) * | 2012-10-26 | 2016-06-01 | Jms Co Ltd | Artificial blood vessel, and method for producing artificial blood vessel |
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US4789601A (en) * | 1987-05-04 | 1988-12-06 | Banes Albert J | Biocompatible polyorganosiloxane composition for cell culture apparatus |
US5324591A (en) * | 1987-03-06 | 1994-06-28 | Geo-Centers, Inc. | Deep ultraviolet photolithographically defined ultra-thin films for selective cell adhesion and outgrowth and method of manufacturing the same and devices containing the same |
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US5369012A (en) * | 1992-03-26 | 1994-11-29 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Method of making a membrane having hydrophilic and hydrophobic surfaces for adhering cells or antibodies by using atomic oxygen or hydroxyl radicals |
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US4689383A (en) * | 1986-03-18 | 1987-08-25 | Thoratec Laboratories Corp. | Hydroxyl-functional disiloxanes and polysiloxane oligomers |
US4822741A (en) * | 1987-05-04 | 1989-04-18 | Banes Albert J | Biocompatible polyorganosiloxane composition for cell culture apparatus |
US4839280A (en) * | 1987-05-04 | 1989-06-13 | Banes Albert J | Apparatus for applying stress to cell cultures |
-
1995
- 1995-06-07 US US08/487,604 patent/US5733538A/en not_active Expired - Lifetime
-
1996
- 1996-05-22 WO PCT/US1996/007500 patent/WO1996040187A1/en active IP Right Grant
- 1996-05-22 ES ES96914755T patent/ES2155188T3/en not_active Expired - Lifetime
- 1996-05-22 EP EP96914755A patent/EP0779815B1/en not_active Expired - Lifetime
- 1996-05-22 AU AU58025/96A patent/AU5802596A/en not_active Abandoned
- 1996-05-22 CA CA002197000A patent/CA2197000C/en not_active Expired - Fee Related
- 1996-05-22 JP JP50068797A patent/JP2001516228A/en active Pending
- 1996-05-22 DE DE69612267T patent/DE69612267T2/en not_active Expired - Lifetime
Patent Citations (4)
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US5324591A (en) * | 1987-03-06 | 1994-06-28 | Geo-Centers, Inc. | Deep ultraviolet photolithographically defined ultra-thin films for selective cell adhesion and outgrowth and method of manufacturing the same and devices containing the same |
US4789601A (en) * | 1987-05-04 | 1988-12-06 | Banes Albert J | Biocompatible polyorganosiloxane composition for cell culture apparatus |
US5330911A (en) * | 1989-09-28 | 1994-07-19 | Board Of Regents, The University Of Texas System | Surfaces having desirable cell adhesive effects |
US5369012A (en) * | 1992-03-26 | 1994-11-29 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Method of making a membrane having hydrophilic and hydrophobic surfaces for adhering cells or antibodies by using atomic oxygen or hydroxyl radicals |
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Title |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6262287B1 (en) * | 1997-05-15 | 2001-07-17 | Givaudan-Roure (International) Sa | Fragrance precursor compounds |
EP1959971A2 (en) * | 2005-12-08 | 2008-08-27 | The Polymer Technology Group, Inc. | Self-assembling monomers and oligomers as surface-modifying endgroups for polymers |
EP1959971A4 (en) * | 2005-12-08 | 2010-01-20 | Polymer Technology Group Inc | Self-assembling monomers and oligomers as surface-modifying endgroups for polymers |
EP2213293A3 (en) * | 2005-12-08 | 2011-09-28 | The Polymer Technology Group Incorporated | Self-assembling monomers and oligomers as surface-modifying endgroups for polymers |
Also Published As
Publication number | Publication date |
---|---|
EP0779815B1 (en) | 2001-03-28 |
ES2155188T3 (en) | 2001-05-01 |
CA2197000A1 (en) | 1996-12-19 |
CA2197000C (en) | 2003-10-21 |
JP2001516228A (en) | 2001-09-25 |
US5733538A (en) | 1998-03-31 |
DE69612267D1 (en) | 2001-05-03 |
EP0779815A4 (en) | 1998-06-03 |
DE69612267T2 (en) | 2001-07-05 |
EP0779815A1 (en) | 1997-06-25 |
AU5802596A (en) | 1996-12-30 |
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