CA2389922A1 - Amphiphilic networks, implantable immunoisolatory devices, and methods of preparation - Google Patents
Amphiphilic networks, implantable immunoisolatory devices, and methods of preparation Download PDFInfo
- Publication number
- CA2389922A1 CA2389922A1 CA002389922A CA2389922A CA2389922A1 CA 2389922 A1 CA2389922 A1 CA 2389922A1 CA 002389922 A CA002389922 A CA 002389922A CA 2389922 A CA2389922 A CA 2389922A CA 2389922 A1 CA2389922 A1 CA 2389922A1
- Authority
- CA
- Canada
- Prior art keywords
- network
- tubular
- amphiphilic
- individual
- hydrophobic crosslinking
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
- A61K9/0024—Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/56—Acrylamide; Methacrylamide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
- C08F255/08—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having four or more carbon atoms
- C08F255/10—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having four or more carbon atoms on to butene polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/12—Polymers provided for in subclasses C08C or C08F
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
Abstract
The present invention provides high mechanical strength amphiphilic polymer networks and implantable biological devices that are capable of encasing and , thus, immunoisolating biological material from the immunological response of a host individual. The present invention also provides methods for the formati on of the amphiphilic networks and implantable biological devices. The present invention also provides a method for the treatment of type I diabetes mellit us comprising the steps of encasing a sufficient amount of islet of Langerhans cells within said biological device, wherein said biological device is capab le of immunoisolating said encased islet cells upon implantation into an individual; implanting said biological device into a diabetic host individua l; allowing said implanted biological device to remain implanted said diabetic individual for a time sufficient to normalize the blood glucose level in sai d diabetic individual.
Claims (16)
1. An amphiphilic network comprising the reaction product of hydrophobic crosslinking agents and hydrophilic monomers, wherein the hydrophobic crosslinking agents are telechelic three-arm polyisobutylenes, having acrylate or methacrylate end caps represented by formula (I);
wherein R1 is an isobutylene polymer represented by formula (II):
wherein A is a moiety that connects R1 to the acrylate or methacrylate end caps;
wherein R2 is hydrogen or a methyl group;
wherein x is the degree of polymerization of the isobutylene; and wherein said hydrophilic monomers are derived from an acrylate selected from the group consisting of formulas (III), (IV) and (V):
wherein R3 is hydrogen or methyl, R4 is an alkylene group having from about 2 to about 4 carbon atoms, and R5 and R6 may be the same or different and each is hydrogen or an alkyl radical having 1 to about 4 carbon atoms.
wherein R1 is an isobutylene polymer represented by formula (II):
wherein A is a moiety that connects R1 to the acrylate or methacrylate end caps;
wherein R2 is hydrogen or a methyl group;
wherein x is the degree of polymerization of the isobutylene; and wherein said hydrophilic monomers are derived from an acrylate selected from the group consisting of formulas (III), (IV) and (V):
wherein R3 is hydrogen or methyl, R4 is an alkylene group having from about 2 to about 4 carbon atoms, and R5 and R6 may be the same or different and each is hydrogen or an alkyl radical having 1 to about 4 carbon atoms.
2. The amphiphilic network of claim 1, wherein A is at least one of:
and
and
3. The amphiphilic network of claim 1, wherein the M n of the hydrophobic crosslinking agent is from about 2,000 g/mol to about 15,000 g/mol.
4. The amphiphilic network of claim 1, wherein the network is further characterized by at least one of the following:
i) wherein ratio of the hydrophobic crosslinking agent to the hydrophilic monomer is from about 80:20 to about 20:80 by weight;
ii) wherein the ratio of the hydrophobic crosslinking agent to the hydrophilic monomer is from about 70:30 to about 30:70 by weight;
iii) wherein the ratio of the hydrophobic crosslinking agent to the hydrophilic monomer is from about 60:40 to about 40:60 by weight; and iv) wherein the ratio of the hydrophobic crosslinking agent to the hydrophilic monomer is from about 50:50 by weight.
i) wherein ratio of the hydrophobic crosslinking agent to the hydrophilic monomer is from about 80:20 to about 20:80 by weight;
ii) wherein the ratio of the hydrophobic crosslinking agent to the hydrophilic monomer is from about 70:30 to about 30:70 by weight;
iii) wherein the ratio of the hydrophobic crosslinking agent to the hydrophilic monomer is from about 60:40 to about 40:60 by weight; and iv) wherein the ratio of the hydrophobic crosslinking agent to the hydrophilic monomer is from about 50:50 by weight.
5. The amphiphilic network of claim 1, wherein the network can absorb at least one of i) water or ii) n-heptane.
6. The amphiphilic network of claim 1, wherein the network is further characterized by at least one of the following:
i) wherein the network has a tensile strength as measured by the stress at break of at least about 0.8 Mpa; and ii) wherein the network has an elongation of at least about 250 percent.
i) wherein the network has a tensile strength as measured by the stress at break of at least about 0.8 Mpa; and ii) wherein the network has an elongation of at least about 250 percent.
7. A method of forming the amphiphilic network of claim 1 comprising:
copolymerizing and crosslinking hydrophilic monomers, wherein said hydrophilic monomers are derived from an acrylate selected from the group consisting of formulas (III), (IV) and (V):
wherein R3 is hydrogen or methyl, R4 is an alkylene group having from about 2 to about 4 carbon atoms, and R5 and R6 may be the same or different and each is hydrogen or an alkyl radical having 1 to about 4 carbon atoms;
with hydrophobic crosslinking agents, wherein the hydrophobic crosslinking agents are acrylate or methacrylate-capped three-arm star polyisobutylenes represented by formula (I):
wherein R1 is an isobutylene polymer represented by formula (II):
wherein A is a moiety that connects R1 to the acrylate or methacrylate end caps;
wherein R2 is hydrogen or a methyl group; and wherein x is the degree of polymerization of the isobutylene.
copolymerizing and crosslinking hydrophilic monomers, wherein said hydrophilic monomers are derived from an acrylate selected from the group consisting of formulas (III), (IV) and (V):
wherein R3 is hydrogen or methyl, R4 is an alkylene group having from about 2 to about 4 carbon atoms, and R5 and R6 may be the same or different and each is hydrogen or an alkyl radical having 1 to about 4 carbon atoms;
with hydrophobic crosslinking agents, wherein the hydrophobic crosslinking agents are acrylate or methacrylate-capped three-arm star polyisobutylenes represented by formula (I):
wherein R1 is an isobutylene polymer represented by formula (II):
wherein A is a moiety that connects R1 to the acrylate or methacrylate end caps;
wherein R2 is hydrogen or a methyl group; and wherein x is the degree of polymerization of the isobutylene.
8. The method of claim 7, wherein A is at least one of:
and
and
9. The method of claim 8, wherein said amphiphilic polymer network is copolymerized and simultaneously crosslinked in a horizontally-disposed and rotating cylinder.
10. An implantable biological device that is capable of encapsulating biologically active moieties, and immunoisolating said moieties from the immunological response of a host individual, said device comprising an amphiphilic network membrane of claim 1.
11. The implantable biological device of claim 10, wherein the device is an implantable tubular-shaped device.
12. The implantable biological device of claim 19, wherein the tubular-shaped device is further characterized by at least one of the following:
i) wherein said tubular-shaped device has an inner volume of less than about 5 milliliters;
ii) wherein said tubular-shaped device has an inner volume of less than about milliliter.
iii) wherein said the wall of membrane of said tubular-shaped device has thickness of about 0.001 cm to about 0.2 centimeters;
iv) wherein the length of said tubular-shaped device is from about 1 to about cm;
v) wherein the diameter of said tubular-shaped device is less than about 2 mm.
i) wherein said tubular-shaped device has an inner volume of less than about 5 milliliters;
ii) wherein said tubular-shaped device has an inner volume of less than about milliliter.
iii) wherein said the wall of membrane of said tubular-shaped device has thickness of about 0.001 cm to about 0.2 centimeters;
iv) wherein the length of said tubular-shaped device is from about 1 to about cm;
v) wherein the diameter of said tubular-shaped device is less than about 2 mm.
13. The implantable biological device of claim 10, wherein the biologically active moieties are selected form the group consisting of cells, tissues, proteins, growth factors, pharmacological agents selected from the group consisting of anti-bacterial agents, anti-viral agents and anti-fungal agents, and cytokines, and wherein the cells are pancreatic islet cells selected from porcine and bovine islet cells.
14. A method of encasing and immunoisolating biologically active moieties upon implantation into a host individual comprising:
providing the amphiphilic network of claim 1;
forming said amphiphilic network into a desired three-dimensional shape; and encasing biologically active moieties into the formed shape.
providing the amphiphilic network of claim 1;
forming said amphiphilic network into a desired three-dimensional shape; and encasing biologically active moieties into the formed shape.
15. A method for treating Type I diabetes in a diabetic host individual comprising:
providing the amphiphilic network of claim 1;
forming said amphiphilic network into an elongated tubular device;
encasing a sufficient amount of islet of pancreatic cells within said tubular device, wherein said tubular device is capable of immunoisolating said encased islet cells upon implantation into an individual;
implanting said tubular device into the diabetic host individual; and allowing said implanted tubular device to remain implanted the diabetic individual for a time sufficient to normalize the blood glucose level in the diabetic individual.
providing the amphiphilic network of claim 1;
forming said amphiphilic network into an elongated tubular device;
encasing a sufficient amount of islet of pancreatic cells within said tubular device, wherein said tubular device is capable of immunoisolating said encased islet cells upon implantation into an individual;
implanting said tubular device into the diabetic host individual; and allowing said implanted tubular device to remain implanted the diabetic individual for a time sufficient to normalize the blood glucose level in the diabetic individual.
16. The method of claim 30, wherein the islet cells are selected from porcine and bovine pancreatic islet cells.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/433,660 US6365171B1 (en) | 1999-11-04 | 1999-11-04 | Amphiphilic networks, implantable immunoisolatory devices and methods of preparation |
| US09/433,660 | 1999-11-04 | ||
| PCT/US2000/028122 WO2001032730A1 (en) | 1999-11-04 | 2000-10-11 | Amphiphilic networks, implantable immunoisolatory devices, and methods of preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2389922A1 true CA2389922A1 (en) | 2001-05-10 |
| CA2389922C CA2389922C (en) | 2010-03-09 |
Family
ID=23721046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002389922A Expired - Fee Related CA2389922C (en) | 1999-11-04 | 2000-10-11 | Amphiphilic networks, implantable immunoisolatory devices, and methods of preparation |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6365171B1 (en) |
| EP (1) | EP1252210A1 (en) |
| AU (1) | AU7878600A (en) |
| CA (1) | CA2389922C (en) |
| WO (1) | WO2001032730A1 (en) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9617976D0 (en) * | 1996-08-28 | 1996-10-09 | British Tech Group | Method of and apparatus for nuclear quadrupole resonance testing a sample |
| US20020099438A1 (en) | 1998-04-15 | 2002-07-25 | Furst Joseph G. | Irradiated stent coating |
| US20030040790A1 (en) * | 1998-04-15 | 2003-02-27 | Furst Joseph G. | Stent coating |
| US7967855B2 (en) * | 1998-07-27 | 2011-06-28 | Icon Interventional Systems, Inc. | Coated medical device |
| US8070796B2 (en) | 1998-07-27 | 2011-12-06 | Icon Interventional Systems, Inc. | Thrombosis inhibiting graft |
| WO2001088025A1 (en) * | 2000-05-16 | 2001-11-22 | Biocure, Inc. | Membranes formed from amphiphilic copolymers |
| FR2826454B1 (en) * | 2001-06-26 | 2003-10-17 | Bio Merieux | ANALYSIS CARDS |
| US8740973B2 (en) * | 2001-10-26 | 2014-06-03 | Icon Medical Corp. | Polymer biodegradable medical device |
| US6727322B2 (en) * | 2002-04-01 | 2004-04-27 | The University Of Akron | Amphiphilic networks, implantable immunoisolatory devices, and methods of preparation |
| US8016881B2 (en) * | 2002-07-31 | 2011-09-13 | Icon Interventional Systems, Inc. | Sutures and surgical staples for anastamoses, wound closures, and surgical closures |
| ATE356838T1 (en) * | 2002-08-09 | 2007-04-15 | Ottawa Health Research Inst | BIOSYNTHETIC MATRIX AND THEIR USE |
| US7211108B2 (en) * | 2004-01-23 | 2007-05-01 | Icon Medical Corp. | Vascular grafts with amphiphilic block copolymer coatings |
| US7540995B2 (en) | 2005-03-03 | 2009-06-02 | Icon Medical Corp. | Process for forming an improved metal alloy stent |
| WO2006110197A2 (en) * | 2005-03-03 | 2006-10-19 | Icon Medical Corp. | Polymer biodegradable medical device |
| US9107899B2 (en) | 2005-03-03 | 2015-08-18 | Icon Medical Corporation | Metal alloys for medical devices |
| US20060264914A1 (en) * | 2005-03-03 | 2006-11-23 | Icon Medical Corp. | Metal alloys for medical devices |
| US20060201601A1 (en) * | 2005-03-03 | 2006-09-14 | Icon Interventional Systems, Inc. | Flexible markers |
| US7488444B2 (en) * | 2005-03-03 | 2009-02-10 | Icon Medical Corp. | Metal alloys for medical devices |
| US8323333B2 (en) * | 2005-03-03 | 2012-12-04 | Icon Medical Corp. | Fragile structure protective coating |
| DE102005021093A1 (en) * | 2005-05-06 | 2006-11-09 | Basf Ag | Process for the preparation of polyisobutyl-substituted cyclohexanols |
| US7715922B1 (en) | 2005-11-16 | 2010-05-11 | Pacesetter, Inc. | Polyethylene oxide and polyisobutylene copolymers and their usage on medical devices |
| US7553546B1 (en) | 2005-11-16 | 2009-06-30 | Pacesetter, Inc. | Polyethylene oxide and silicone copolymers and their usage on medical devices |
| US7708774B1 (en) | 2005-11-16 | 2010-05-04 | Pacesetter, Inc. | Polyethylene oxide and silicone copolymers and their usage on medical devices |
| WO2008008291A2 (en) * | 2006-07-13 | 2008-01-17 | Icon Medical Corp. | Stent |
| EP2056759B1 (en) * | 2006-08-29 | 2015-01-14 | The University of Akron | Implantable devices for producing insulin |
| KR20140066800A (en) | 2006-11-30 | 2014-06-02 | 더 유니버시티 오브 아크론 | Polyisobutylenes, and process for making same |
| WO2008127730A1 (en) * | 2007-04-12 | 2008-10-23 | The University Of Akron | Injectible cyanoacrylate-functionalized polyisobutylenes |
| US8398916B2 (en) | 2010-03-04 | 2013-03-19 | Icon Medical Corp. | Method for forming a tubular medical device |
| WO2015199816A1 (en) | 2014-06-24 | 2015-12-30 | Icon Medical Corp. | Improved metal alloys for medical devices |
| US11766506B2 (en) | 2016-03-04 | 2023-09-26 | Mirus Llc | Stent device for spinal fusion |
| US11198831B2 (en) | 2019-01-31 | 2021-12-14 | Kvi Llc | Lubricant for a device |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4085168A (en) | 1971-02-22 | 1978-04-18 | Cpc International Inc. | Chemically joined, phase separated self-cured hydrophilic thermoplastic graft copolymers and their preparation |
| US4486572A (en) | 1983-07-06 | 1984-12-04 | University Of Akron | Synthesis of amphiphilic block copolymers and networks |
| US5158881A (en) | 1987-11-17 | 1992-10-27 | Brown University Research Foundation | Method and system for encapsulating cells in a tubular extrudate in separate cell compartments |
| US5073381A (en) | 1988-08-15 | 1991-12-17 | University Of Akron | Amphiphilic networks |
| US4942204A (en) | 1988-08-15 | 1990-07-17 | The University Of Akron | Amphiphilic networks |
| AU651654B2 (en) | 1992-01-14 | 1994-07-28 | Endo Pharmaceuticals Solutions Inc. | Manufacture of water-swellable hydrophilic articles and drug delivery devices |
| EP0585368B1 (en) | 1991-04-25 | 1997-08-06 | Brown University Research Foundation | Implantable biocompatible immunoisolatory vehicle for delivery of selected therapeutic products |
| US5807944A (en) | 1996-06-27 | 1998-09-15 | Ciba Vision Corporation | Amphiphilic, segmented copolymer of controlled morphology and ophthalmic devices including contact lenses made therefrom |
-
1999
- 1999-11-04 US US09/433,660 patent/US6365171B1/en not_active Expired - Lifetime
-
2000
- 2000-10-11 CA CA002389922A patent/CA2389922C/en not_active Expired - Fee Related
- 2000-10-11 WO PCT/US2000/028122 patent/WO2001032730A1/en not_active Application Discontinuation
- 2000-10-11 AU AU78786/00A patent/AU7878600A/en not_active Abandoned
- 2000-10-11 EP EP00968945A patent/EP1252210A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CA2389922C (en) | 2010-03-09 |
| US6365171B1 (en) | 2002-04-02 |
| EP1252210A1 (en) | 2002-10-30 |
| WO2001032730A1 (en) | 2001-05-10 |
| AU7878600A (en) | 2001-05-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20151013 |