US5891506A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Oxidative method for attachment of glycoproteins or glycopeptides to surfaces of medical devices
Assignee: Medtronic Inc
•
Filing: 1997-12-04
•
Granted: 1999-04-06
•
Expires: 2017-12-04
Abstract
Abstract A method for making a medical device having at least one glycoprotein and/or glycopeptide immobilized on a substrate surface is provided. The method may include 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. Another method of the present invention may be employed to crosslink glycoproteins and/or glycopeptides immobilized on medical device surfaces. Additionally, one method of the present invention may be employed to crosslink glycoproteins and/or glycopeptides, thereby forming a crosslinked biomaterial or a crosslinked medical device coating.
Inventors
- 👤 James R. Keogh
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 08:13
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: 66
Claim 1
Independent Claim
156 words
A method of forming a coating on a surface of a medical device, the coating imparting improved biocompatibility characteristics to the surface, the surface being suitable for contacting tissue, blood and other bodily fluids in or temporarily removed from a living mammalian subject, the method comprising the ordered steps of: (a) combining a periodate with a biomolecule, the biomolecule comprising a 1,2 dihydroxy moiety and an amino acid residue for oxidizing 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 biomolecule on the surface, the immobilized biomolecule forming the coating.
Claim 2
Independent Claim
156 words
A method of forming a coating on a surface of a medical device, the coating imparting improved biocompatibility characteristics to the surface, the surface being suitable for contacting tissue, blood and other bodily fluids in or temporarily removed from a living mammalian subject, the method comprising the ordered steps of: (a) combining a periodate with a biomolecule, the biomolecule comprising a 1,2 dihydroxy moiety and an amino acid residue for oxidizing 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 biomolecule on the surface, the immobilized biomolecule forming the coating.
Claim 3
Dependent Claim
71 words
The method of claim 1, wherein the device is selected from the group consisting of a blood-contacting medical device, a tissue-contacting medical device, a bodily fluid-contacting medical device, an implantable medical device, an extracorporeal medical device, a blood oxygenator, a blood pump, tubing for carrying blood, an endoprosthesis medical device, a vascular graft, a stent, a pacemaker lead, a heart valve, temporary intravascular medical device, a catheter and a guide wire.
Claim 4
Dependent Claim
20 words
The method of claim 1, wherein the biomolecule is selected from the group consisting of a glycoprotein and a glycopeptide.
Claim 5
Dependent Claim
76 words
The method of claim 3, 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 6
Dependent Claim
13 words
The method of claim 3, wherein the glycoprotein is a naturally occurring glycoprotein.
Claim 7
Dependent Claim
11 words
The method of claim 3, wherein the glycoprotein is synthesized chemically.
Claim 8
Dependent Claim
73 words
The method of claim 3, wherein the glycopeptide is selected from the group consisting of an anticoagulant peptide, an antithrombotic peptide, a clotting peptide, a platelet peptide, an anti-inflammatory peptide, a defense peptide, an enzyme, a hormone, a growth factor, a neurotransmitter, a cytokine, a blood peptide, a regulatory peptide, a transport peptide, a fibrous peptide, a structural peptide, a membrane peptide, a cell attachment peptide, a toxin, an antibiotic, and a ligand.
Claim 9
Dependent Claim
13 words
The method of claim 3, wherein the glycopeptide is a naturally occurring glycopeptide.
Claim 10
Dependent Claim
11 words
The method of claim 3, wherein the glycopeptide is synthesized chemically.
Claim 11
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 12
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 13
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 Celsius.
Claim 14
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 15
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 Celsius.
Claim 16
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 17
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 18
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 Celsius.
Claim 19
Dependent Claim
16 words
The method of claim 1, wherein the oxidizing step is performed in the absence of light.
Claim 20
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 21
Dependent Claim
88 words
The method of claim 1, 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, 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 22
Independent Claim
136 words
A method of crosslinking a coating on a surface of a medical device, the coating imparting improved biocompatibility characteristics to the surface, the surface being suitable for contacting tissue, blood and other bodily fluids in or temporarily removed from a living mammalian subject, the method comprising the ordered steps of: (a) immobilizing a biomolecule on the surface, the biomolecule forming the coating and comprising a 1,2 dihydroxy moiety, an amino acid residue 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 23
Independent Claim
136 words
A method of crosslinking a coating on a surface of a medical device, the coating imparting improved biocompatibility characteristics to the surface, the surface being suitable for contacting tissue, blood and other bodily fluids in or temporarily removed from a living mammalian subject, the method comprising the ordered steps of: (a) immobilizing a biomolecule on the surface, the biomolecule forming the coating and comprising a 1,2 dihydroxy moiety, an amino acid residue 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 24
Dependent Claim
71 words
The method of claim 21, wherein the device is selected from the group consisting of a blood-contacting medical device, a tissue-contacting medical device, a bodily fluid-contacting medical device, an implantable medical device, an extracorporeal medical device, a blood oxygenator, a blood pump, tubing for carrying blood, an endoprosthesis medical device, a vascular graft, a stent, a pacemaker lead, a heart valve, temporary intravascular medical device, a catheter and a guide wire.
Claim 25
Dependent Claim
20 words
The method of claim 21, wherein the biomolecule is selected from the group consisting of a glycoprotein and a glycopeptide.
Claim 26
Dependent Claim
76 words
The method of claim 23, 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 27
Dependent Claim
13 words
The method of claim 23, wherein the glycoprotein is a naturally occurring glycoprotein.
Claim 28
Dependent Claim
11 words
The method of claim 23, wherein the glycoprotein is synthesized chemically.
Claim 29
Dependent Claim
73 words
The method of claim 23, wherein the glycopeptide is selected from the group consisting of an anticoagulant peptide, an antithrombotic peptide, a clotting peptide, a platelet peptide, an anti-inflammatory peptide, a defense peptide, an enzyme, a hormone, a growth factor, a neurotransmitter, a cytokine, a blood peptide, a regulatory peptide, a transport peptide, a fibrous peptide, a structural peptide, a membrane peptide, a cell attachment peptide, a toxin, an antibiotic, and a ligand.
Claim 30
Dependent Claim
13 words
The method of claim 23, wherein the glycopeptide is a naturally occurring glycopeptide.
Claim 31
Dependent Claim
11 words
The method of claim 23, wherein the glycopeptide is synthesized chemically.
Claim 32
Dependent Claim
23 words
The method of claim 21, wherein the periodate comprises at least one of periodic acid, sodium periodate, alkali metal periodates, and potassium periodate.
Claim 33
Dependent Claim
21 words
The method of claim 21, wherein the reducing agent comprises at least one of sodium borohydride, sodium cyanoborohydride, and amine borane.
Claim 34
Dependent Claim
31 words
The method of claim 21, 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 35
Dependent Claim
34 words
The method of claim 21, wherein the periodate is combined with the 1,2 dihydroxy moiety and the amine moiety in an aqueous solution having a temperature between about 0 and about 50 degrees Celsius.
Claim 36
Dependent Claim
31 words
The method of claim 21, 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 37
Dependent Claim
30 words
The method of claim 21, wherein the reducing agent is combined with the imine moiety in an aqueous solution having a temperature between about 0 and about 50 degrees Celsius.
Claim 38
Dependent Claim
16 words
The method of claim 21, wherein the oxidizing step is performed in the absence of light.
Claim 39
Dependent Claim
31 words
The method of claim 21, 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 40
Dependent Claim
84 words
The method of claim 21, 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, 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 41
Independent Claim
124 words
A method of forming an insoluble crosslinked biomaterial for use in a medical device, the biomaterial being suitable for contacting tissue, blood and other bodily fluids in or temporarily removed from a living mammalian subject, the method comprising the ordered steps of: (a) combining a periodate with at least two different cross-linking biomolecules, each biomolecule comprising a 1,2 dihydroxy moiety, an amino acid residue, and an amine moiety, the periodate oxidizing the 1,2 dihydroxy moiety to form an aldehyde moiety; (b) allowing the aldehyde moiety of one biomolecule to combine with the amine moiety of another biomolecule to form an imine moiety; and (c) reacting the imine moiety with a reducing agent to form a secondary amine and thereby forming an insoluble crosslinked biomaterial.
Claim 42
Independent Claim
124 words
A method of forming an insoluble crosslinked biomaterial for use in a medical device, the biomaterial being suitable for contacting tissue, blood and other bodily fluids in or temporarily removed from a living mammalian subject, the method comprising the ordered steps of: (a) combining a periodate with at least two different cross-linking biomolecules, each biomolecule comprising a 1,2 dihydroxy moiety, an amino acid residue, and an amine moiety, the periodate oxidizing the 1,2 dihydroxy moiety to form an aldehyde moiety; (b) allowing the aldehyde moiety of one biomolecule to combine with the amine moiety of another biomolecule to form an imine moiety; and (c) reacting the imine moiety with a reducing agent to form a secondary amine and thereby forming an insoluble crosslinked biomaterial.
Claim 43
Dependent Claim
62 words
The method of claim 39, wherein the medical device is selected from the group consisting of a blood-contacting medical device, a tissue-contacting medical device, a bodily fluid-contacting medical device, an implantable medical device, an endoprosthesis medical device, a cell seeding medical device, a cell binding medical device, a cell separating medical device, a vascular graft, a heart valve, and a tissue glue.
Claim 44
Dependent Claim
36 words
The method of claim 39, comprising the further step of forming the crosslinked biomaterial into at least one shape selected from the group consisting of a tube, a rod, a membrane, a balloon and a bag.
Claim 45
Dependent Claim
28 words
The method of claim 39, wherein at least one of the at least two different biomolecules is selected from the group consisting of a glycoprotein and a glycopeptide.
Claim 46
Dependent Claim
76 words
The method of claim 42, 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 47
Dependent Claim
13 words
The method of claim 42, wherein the glycoprotein is a naturally occurring glycoprotein.
Claim 48
Dependent Claim
11 words
The method of claim 42, wherein the glycoprotein is synthesized chemically.
Claim 49
Dependent Claim
73 words
The method of claim 42, wherein the glycopeptide is selected from the group consisting of an anticoagulant peptide, an antithrombotic peptide, a clotting peptide, a platelet peptide, an anti-inflammatory peptide, a defense peptide, an enzyme, a hormone, a growth factor, a neurotransmitter, a cytokine, a blood peptide, a regulatory peptide, a transport peptide, a fibrous peptide, a structural peptide, a membrane peptide, a cell attachment peptide, a toxin, an antibiotic, and a ligand.
Claim 50
Dependent Claim
13 words
The method of claim 42, wherein the glycopeptide is a naturally occurring glycopeptide.
Claim 51
Dependent Claim
11 words
The method of claim 42, wherein the glycopeptide is synthesized chemically.
Claim 52
Dependent Claim
23 words
The method of claim 39, wherein the periodate comprises at least one of periodic acid, sodium periodate, alkali metal periodates, and potassium periodate.
Claim 53
Dependent Claim
31 words
The method of claim 39, 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 54
Dependent Claim
34 words
The method of claim 39, wherein the periodate is combined with the 1,2 dihydroxy moiety and the amine moiety in an aqueous solution having a temperature between about 0 and about 50 degrees Celsius.
Claim 55
Dependent Claim
16 words
The method of claim 39, wherein the oxidizing step is performed in the absence of light.
Claim 56
Dependent Claim
21 words
The method of claim 39, wherein the reducing agent comprises at least one of sodium borohydride, sodium cyanoborohydride, and amine borane.
Claim 57
Dependent Claim
31 words
The method of claim 39, 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 58
Dependent Claim
30 words
The method of claim 39, wherein the reducing agent is combined with the imine moiety in an aqueous solution having a temperature between about 0 and about 50 degrees Celsius.
Claim 59
Dependent Claim
17 words
The method of claim 39, further comprising the step of combining the crosslinked biomaterial with a bioagent.
Claim 60
Dependent Claim
68 words
The method of claim 56, wherein the biomolecule is selected from the group consisting of an anticoagulant, an antithrombotic, an anti-inflammatory, an antibody, an immunoglobulin, an enzyme, a hormone, a growth factor, a neurotransmitter, a cytokine, a globular protein, a structural protein, a membrane protein, a cell attachment protein, a structural peptide, a membrane peptide, a cell attachment peptide, a proteoglycan, a toxin, an antibiotic, and a ligand.
Claim 61
Dependent Claim
51 words
The method of claim 39, wherein the crosslinked biomaterial is employed as a coating on a surface of the medical device, the coating imparting improved biocompatibility characteristics to the surface, the surface being suitable for contacting tissue, blood and other bodily fluids in or temporarily removed from a living mammalian subject.
Claim 62
Dependent Claim
71 words
The method of claim 58, wherein the device is selected from the group consisting of a blood-contacting medical device, a tissue-contacting medical device, a bodily fluid-contacting medical device, an implantable medical device, an extracorporeal medical device, a blood oxygenator, a blood pump, tubing for carrying blood, an endoprosthesis medical device, a vascular graft, a stent, a pacemaker lead, a heart valve, temporary intravascular medical device, a catheter and a guide wire.
Claim 63
Dependent Claim
31 words
The method of claim 58, 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 64
Dependent Claim
88 words
The method of claim 58, 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, 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 65
Dependent Claim
16 words
The method of claim 58, comprising the further step of combining the coating with a bioagent.
Claim 66
Dependent Claim
68 words
The method of claim 62, wherein the bioagent is selected from the group consisting of an anticoagulant, an antithrombotic, an anti-inflammatory, an antibody, an immunoglobulin, an enzyme, a hormone, a growth factor, a neurotransmitter, a cytokine, a globular protein, a structural protein, a membrane protein, a cell attachment protein, a structural peptide, a membrane peptide, a cell attachment peptide, a proteoglycan, a toxin, an antibiotic, and a ligand.
References Cited (Backward Citations)
US3826678A
Cited
US4613665A
Cited
US4521564A
Cited
US4600652A
Cited
US4642242A
Cited
US5104976A
Cited
US5057313A
Cited
US4720512A
Cited
US4786556A
Cited
US5274119A
Cited
US5053048A
Cited
US5521290A
Cited
US5258501A
Cited
US5077372A
Cited
US5032666A
Cited
US5362852A
Cited
US5344455A
Cited
US5532352A
Cited
US5614487A
Cited
US5443953A
Cited
US5795560A
Cited
US5677276A
Cited
US5672638A
Cited
US5728420A
Cited
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