US5728420A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Oxidative method for attachment of glycoproteins to surfaces of medical devices
Assignee: Medtronic Inc
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Filing: 1996-08-09
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Granted: 1998-03-17
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Expires: 2016-08-09
Abstract
Abstract A method for making a medical device having a glycoprotein immobilized on a substrate surface is provided. The method includes oxidizing 1,2 dihydroxy moieties with a periodate to form an aldehyde-functional material; combining the aldehyde-functional material with an amino-functional material to bond the two materials together through an imine moiety; and reacting the imine moiety with a reducing agent to form a secondary amine.
Inventors
- 👤 James R. Keogh
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 12:44
CPC Classifications
A; A61; A61L; A61L31/00; A61L31/08; A61L31/10; A61L27/00; A61L27/28; A61L27/34; A61L29/00; A61L29/08; A61L29/085; A61L33/00; A61L33/0005; A61L33/0011; A61L33/0029
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
129 words
A method of forming a coating on a surface of a medical device, the coating imparting biocompatibility characteristics to the surface, the method comprising the ordered steps of: (a) combining a periodate with a glycoprotein, the glycoprotein comprising a 1,2 dihydroxy moiety, to oxidize the 1,2 dihydroxy moiety to form an aldehyde-functional material; (b) providing the medical device, the device having a suitable biomaterial forming the surface, an amine moiety being disposed on the surface; (c) combining the aldehyde-functional material with the amine moiety to bond the aldehyde-functional material to the amine moiety and thereby form an imine moiety; and (d) reacting the imine moiety with a reducing agent to form an amine linkage, the amine linkage immobilizing the glycoprotein on the surface, the immobilized glycoprotein forming the coating.
Claim 2
Independent Claim
129 words
A method of forming a coating on a surface of a medical device, the coating imparting biocompatibility characteristics to the surface, the method comprising the ordered steps of: (a) combining a periodate with a glycoprotein, the glycoprotein comprising a 1,2 dihydroxy moiety, to oxidize the 1,2 dihydroxy moiety to form an aldehyde-functional material; (b) providing the medical device, the device having a suitable biomaterial forming the surface, an amine moiety being disposed on the surface; (c) combining the aldehyde-functional material with the amine moiety to bond the aldehyde-functional material to the amine moiety and thereby form an imine moiety; and (d) reacting the imine moiety with a reducing agent to form an amine linkage, the amine linkage immobilizing the glycoprotein on the surface, the immobilized glycoprotein forming the coating.
Claim 3
Dependent Claim
46 words
The method of claim 1 wherein the device is selected from the group consisting of an implantable medical device, a blood oxygenator, a blood pump, tubing for carrying blood, a vascular graft, a stent, a pacemaker lead, a heart valve, a catheter and a guide wire.
Claim 4
Dependent Claim
76 words
The method of claim 1 wherein the glycoprotein is selected from the group consisting of an anticoagulant protein, an antithrombotic protein, a clotting protein, a platelet protein, an anti-inflammatory protein, an antibody, an immunoglobulin, a defense protein, an enzyme, a hormone, a growth factor, a globular protein, a blood protein, a regulatory protein, a transport protein, a fibrous protein, a structural protein, a membrane protein, a cell attachment protein, a proteoglycan, a toxin and a ligand.
Claim 5
Dependent Claim
13 words
The method of claim 1 wherein the glycoprotein is a naturally occurring glycoprotein.
Claim 6
Dependent Claim
31 words
The method of claim 1 wherein at least a portion of the surface forms at least one of a tube, a rod, a membrane, a balloon, a bag and a sheet.
Claim 7
Dependent Claim
92 words
The method of claim 5 wherein the surface comprises at least one of a biocompatible material selected from the group consisting of metal, titanium, titanium alloys, tin-nickel alloys, shape memory alloys, aluminum oxide, platinum, platinum alloys, stainless steel, MP35N stainless steel, elgiloy, stellite, pyrolytic carbon, silver carbon, glassy carbon, polymer, polyamide, polycarbonate, polyether, polyester, polyolefin, polyethylene, polypropylene, polystyrene, polyurethane, polyvinyl chloride, polyvinylpyrrolidone, silicone elastomer, fluoropolymer, polyacrylate, polyisoprene, polytetrafluoroethylene, rubber, ceramic, hydroxapatite, human protein, human tissue, animal protein, animal tissue, bone, skin, teeth, collagen, laminin, elastin, fibrin, wood, cellulose, compressed carbon and glass.
Claim 8
Dependent Claim
23 words
The method of claim 1 wherein the periodate comprises at least one of periodic acid, sodium periodate, alkali metal periodates and potassium periodate.
Claim 9
Dependent Claim
21 words
The method of claim 1 wherein the reducing agent comprises at least one of sodium borohydride, sodium cyanoborohydride and amine borane.
Claim 10
Dependent Claim
28 words
The method of claim 1 wherein the periodate is combined with the 1,2 dihydroxy moiety in an aqueous solution having a pH between about 4 and about 9.
Claim 11
Dependent Claim
30 words
The method of claim 1 wherein the periodate is combined with the 1,2 dihydroxy moiety in an aqueous solution having a temperature between about 0 and about 50 degrees Celisius.
Claim 12
Dependent Claim
28 words
The method of claim 1 wherein the aldehyde-functional material and the amine-functional material are combined in an aqueous solution having a pH between about 6 and about 10.
Claim 13
Dependent Claim
30 words
The method of claim 1 wherein the aldehyde-functional material and the amine-functional material are combined in an aqueous solution having a temperature between about 0 and about 50 degrees Celisius.
Claim 14
Dependent Claim
28 words
The method of claim 1 wherein the reducing agent is combined with the imine moiety in an aqueous solution having a pH between about 6 and about 10.
Claim 15
Dependent Claim
30 words
The method of claim 1 wherein the reducing agent is combined with the imine moiety in an aqueous solution having a temperature between about 0 and about 50 degrees Celisius.
Claim 16
Independent Claim
110 words
A method of crosslinking a coating on a surface of a medical device, the coating imparting biocompatibility characteristics to the surface, the method comprising the ordered steps of: (a) immobilizing a glycoprotein on the surface, the glycoprotein forming the coating and comprising a 1,2 dihydroxy moiety and an amine moiety; (b) applying a periodate to the coating to oxidize the 1,2 dihydroxy moiety to form an aldehyde moiety; (c) allowing the aldehyde moiety to combine with the amine moiety to form an imine moiety; and (d) reacting the imine moiety with a reducing agent to form a secondary amine and thereby cause at least portions of the coating to crosslink.
Claim 17
Independent Claim
110 words
A method of crosslinking a coating on a surface of a medical device, the coating imparting biocompatibility characteristics to the surface, the method comprising the ordered steps of: (a) immobilizing a glycoprotein on the surface, the glycoprotein forming the coating and comprising a 1,2 dihydroxy moiety and an amine moiety; (b) applying a periodate to the coating to oxidize the 1,2 dihydroxy moiety to form an aldehyde moiety; (c) allowing the aldehyde moiety to combine with the amine moiety to form an imine moiety; and (d) reacting the imine moiety with a reducing agent to form a secondary amine and thereby cause at least portions of the coating to crosslink.
Claim 18
Dependent Claim
60 words
The method of claim 15 wherein the device is selected from the group consisting of an implantable medical device, a blood oxygenator, a blood pump, tubing for carrying blood, a vascular graft, a stent, a pacemaker lead, a heart valve, a catheter and a guide wire. material comprising a 1,2 dihydroxy moiety and a primary amine moiety comprises a glycoprotein.
Claim 19
Dependent Claim
76 words
The method of claim 15 wherein the glycoprotein is selected from the group consisting of an anticoagulant protein, an antithrombotic protein, a clotting protein, a platelet protein, an anti-inflammatory protein, an antibody, an immunoglobulin, a defense protein, an enzyme, a hormone, a growth factor, a globular protein, a blood protein, a regulatory protein, a transport protein, a fibrous protein, a structural protein, a membrane protein, a cell attachment protein, a proteoglycan, a toxin and a ligand.
Claim 20
Dependent Claim
13 words
The method of claim 15 wherein the glycoprotein is a naturally occurring glycoprotein.
Claim 21
Dependent Claim
23 words
The method of claim 15 wherein the periodate comprises at least one of periodic acid, sodium periodate, alkali metal periodates and potassium periodate.
Claim 22
Dependent Claim
21 words
The method of claim 15 wherein the reducing agent comprises at least one of sodium borohydride, sodium cyanoborohydride and amine borane.
Claim 23
Dependent Claim
31 words
The method of claim 15 wherein the periodate is combined with 1,2 dihydroxy moiety and the amine moiety in an aqueous solution having a pH between about 4 and about 9.
Claim 24
Dependent Claim
35 words
The method of claim 15 wherein the periodate is combined with the 1,2 dihydroxy moiety and a primary amine moiety in an aqueous solution having a temperature between about 0 and about 50 degrees Celisius.
Claim 25
Dependent Claim
31 words
The method of claim 15 wherein the reducing agent is combined with the material comprising an imine moiety in an aqueous solution having a pH between about 6 and about 10.
Claim 26
Dependent Claim
30 words
The method of claim 15 wherein the reducing agent is combined with the imine moiety in an aqueous solution having a temperature between about 0 and about 50 degrees Celisius.
Claim 27
Dependent Claim
16 words
The method of claim 1 wherein the oxidizing step is performed in the absence of light.
Claim 28
Dependent Claim
16 words
The method of claim 15 wherein the oxidizing step is performed in the absence of light.
Claim 29
Dependent Claim
31 words
The method of claim 15 wherein at least a portion of the surface forms at least one of a tube, a rod, a membrane, a balloon, a bag and a sheet.
Claim 30
Dependent Claim
88 words
The method of claim 15 wherein the surface comprises a biocompatible material selected from the group consisting of metal, titanium, titanium alloys, tin-nickel alloys, shape memory alloys, aluminum oxide, platinum, platinum alloys, stainless steel, MP35N stainless steel, elgiloy, stellite, pyrolytic carbon, silver carbon, glassy carbon, polymer, polyamide, polycarbonate, polyether, polyester, polyolefin, polyethylene, polypropylene, polystyrene, polyurethane, polyvinyl chloride, polyvinylpyrrolidone, silicone elastomer, fluoropolymer, polyacrylate, polyisoprene, polytetrafluoroethylene, rubber, ceramic, hydroxapatite, human protein, human tissue, animal protein, animal tissue, bone, skin, teeth, collagen, laminin, elastin, fibrin, wood, cellulose, compressed carbon and glass.
References Cited (Backward Citations)
US3826678A
Cited
US4308254A
Cited
US4613665A
Cited
US4663163A
Cited
US5059654A
Cited
US4521564A
Cited
US4600652A
Cited
US4642242A
Cited
US4786556A
Cited
US4720512A
Cited
US5053048A
Cited
US5258501A
Cited
US5032666A
Cited
US5077372A
Cited
US5362852A
Cited
US5344455A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 2001-03-16 | 2001-09-15 | 2002-03-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2005-03-16 | 2005-09-15 | 2006-03-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2009-03-16 | 2009-09-15 | 2010-03-17 | $7700.00 | Window Closed / Lapsed |