US2006099326A1PendingUtilityA1

Method for attachment of biomolecules to medical device surfaces

Assignee: MEDTRONIC INCPriority: Apr 25, 1996Filed: Dec 7, 2005Published: May 11, 2006

Est. expiryApr 25, 2016(expired)· nominal 20-yr term from priority

Inventors:James R. Keogh Paul V. Trescony

A61L 2300/606C12N 11/14A61L 33/0029A61L 27/28A61L 27/54A61L 27/3641A61L 27/22A61L 33/0082A61L 31/08A61L 33/128A61L 27/24A61L 27/3645Y10S530/811C12N 11/02A61L 29/085Y10S530/81Y10S530/816A61L 33/0047A61L 33/12A61L 31/16A61L 31/10A61L 27/34C08L 89/00A61L 27/3625A61L 33/0011Y10S530/815A61L 33/18G01N 33/543A61K 38/43

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References

Claims

Abstract

A method for making a medical device having at least one biomolecule immobilized on a substrate surface is provided. One method of the present invention includes immobilizing a biomolecule comprising an unsubstituted amide moiety on a biomaterial surface. Another method of the present invention includes immobilizing a biomolecule on a biomaterial surface comprising an unsubstituted amide moiety. Still another method of the present invention may be employed to crosslink biomolecules comprising unsubstituted amide moieties immobilized on medical device surfaces. Additionally, one method of the present invention may be employed to crosslink biomolecules comprising unsubstituted amide moieties in solution, thereby forming a crosslinked biomaterial or a crosslinked medical device coating.

Claims

exact text as granted — not AI-modified

1 - 34 . (canceled)

35 . A method of forming a coated tissue heart valve, the coating imparting improved cell binding characteristics to the surface of the heart valve, the method comprising the steps of: (a) providing the heart valve; (b) providing a biomolecule, the biomolecule comprising an arginine, glycine and aspartic acid amino acid sequence; and (c) combining the biomolecule with the surface of the tissue heart valve to form a chemical bond, the chemical bond immobilizing the biomolecule on the surface, the immobilized biomolecule forming the coating.

36 . The method of claim 35 wherein the biomolecule is a naturally occurring biomolecule.

37 . The method of claim 35 wherein the biomolecule is a chemically synthesized biomolecule.

38 . The method of claim 35 wherein the biomolecule is a peptide.

39 . The method of claim 38 wherein the peptide is a cell attachment peptide.

40 . The method of claim 35 wherein the biomolecule is a protein.

41 . The method of claim 40 wherein the protein is a cell attachment protein.

42 . The method of claim 40 wherein the protein is fibrinogen.

43 . The method of claim 40 wherein the protein is fibronectin.

44 . The method of claim 40 wherein the protein is vitronectin.

45 . The method of claim 40 wherein the protein is collagen.

46 . The method of claim 35 wherein the heart valve is implantable in a heart.

47 . The method of claim 35 further comprising the step of combining at least one reducing agent selected from the group consisting of sodium borohydride, sodium cyanoborohydride and amine borane.

48 . The method of claim 35 further comprising the step of combining a chemical moiety of the biomolecule with a chemical moiety of the surface to form the chemical bond.

49 . The method of claim 48 wherein the chemical moiety of the biomolecule is an aldehyde moiety.

50 . The method of claim 49 wherein the aldehyde moiety is formed by combining a periodate with a 2-aminoalcohol moiety.

51 . The method of claim 50 wherein the periodate comprises at least one of a periodic acid, a sodium periodate, an alkali metal periodate, and a potassium periodate.

52 . The method of claim 49 wherein the aldehyde moiety is formed by combining a periodate with a 1,2-dihydroxy moiety.

53 . The method of claim 52 wherein the periodate comprises at least one of a periodic acid, a sodium periodate, an alkali metal periodate, and a potassium periodate.

54 . The method of claim 48 wherein the chemical moiety of the biomolecule is an epoxide moiety.

55 . The method of claim 48 wherein the chemical moiety of the biomolecule is an isocyanate moiety.

56 . The method of claim 48 wherein the chemical moiety of the biomolecule is a 1,2-dicarbonyl moiety.

57 . The method of claim 48 wherein the chemical moiety of the biomolecule is a phosphate moiety.

58 . The method of claim 48 wherein the chemical moiety of the biomolecule is a sulphate moiety.

59 . The method of claim 48 wherein the chemical moiety of the biomolecule is a carboxylate moiety.

60 . The method of claim 48 wherein the chemical moiety of the surface is a guanidino moiety.

61 . The method of claim 60 wherein the guanidino moiety is formed by combining an amine moiety with a guanidino forming agent.

62 . The method of claim 61 wherein the guanidino forming agent is selected from the group consisting of S-ethylthiouronium bromide, S-ethylthiouronium chloride, O-methylisourea, O-methylisouronium sulfate, O-methylisourea hydrogen sulfate, S-methylisothiourea, 2-methyl-1-nitroisourea, aminoiminomethanesulfonic acid, cyanamide, cyanoguanide, dicyandiamide, 3,5-dimethyl-1-guanylpyrazole nitrate and 3,5-dimethylpyrazole.

63 . The method of claim 61 further comprising the step of combining a stabilizing agent.

64 . The method of claim 63 wherein the stabilizing agent is a borate ion.

65 . The method of claim 61 wherein the amine moiety is formed by combining an unsubstituted amide moiety with an amine forming agent.

66 . The method of claim 65 wherein the amine forming agent is selected from the group consisting of bromine, bromide, bromite, hypobromite, chlorine, chloride, chlorite, hypochlorite, lead tetraacetate, benzyltrimethylammonium tribromide, [bis(trifluoroacetoxy)iodo]benzene, hydroxy(tosyloxy)iodobenzene and iodosylbenzene.

67 . The method of claim 48 wherein the chemical moiety of the surface is a primary amine moiety.

68 . The method of claim 67 wherein the primary amine moiety is formed by combining an unsubstituted amide moiety with an amine forming agent.

69 . The method of claim 68 wherein the amine forming agent is selected from the group consisting of bromine, bromide, bromite, hypobromite, chlorine, chloride, chlorite, hypochlorite, lead tetraacetate, benzyltrimethylammonium tribromide, [bis(trifluoroacetoxy)iodo]benzene, hydroxy(tosyloxy)iodobenzene and iodosylbenzene.

70 . The method of claim 48 wherein the chemical moiety of the surface is an aldehyde moiety.

71 . The method of claim 70 wherein the aldehyde moiety is formed by combining a periodate with a 2-aminoalcohol moiety.

72 . The method of claim 71 wherein the periodate comprises at least one of a periodic acid, a sodium periodate, an alkali metal periodate, and a potassium periodate.

73 . The method of claim 70 wherein the aldehyde moiety is formed by combining a periodate with a 1,2-dihydroxy moiety.

74 . The method of claim 73 wherein the periodate comprises at least one of a periodic acid, a sodium periodate, an alkali metal periodate, and a potassium periodate.

75 . The method of claim 48 wherein the chemical moiety of the surface is an epoxide moiety.

76 . The method of claim 48 wherein the chemical moiety of the surface is an isocyanate moiety.

77 . The method of claim 48 wherein the chemical moiety of the surface is a 1,2-dicarbonyl moiety.

78 . The method of claim 48 wherein the chemical moiety of the surface is a phosphate moiety.

79 . The method of claim 48 wherein the chemical moiety of the surface is a sulphate moiety.

80 . The method of claim 48 wherein the chemical moiety of the surface is a carboxylate moiety.

81 . The method of claim 48 wherein the chemical moiety of the biomolecule is a guanidino moiety.

82 . The method of claim 81 wherein the guanidino moiety is formed by combining an amine moiety with a guanidino forming agent.

83 . The method of claim 82 wherein the guanidino forming agent is selected from the group consisting of S-ethylthiouronium bromide, S-ethylthiouronium chloride, O-methylisourea, O-methylisouronium sulfate, O-methylisourea hydrogen sulfate, S-methylisothiourea, 2-methyl-1-nitroisourea, aminoiminomethanesulfonic acid, cyanamide, cyanoguanide, dicyandiamide, 3,5-dimethyl-1-guanylpyrazole nitrate and 3,5-dimethylpyrazole.

84 . The method of claim 82 further comprising the step of combining a stabilizing agent.

85 . The method of claim 84 wherein the stabilizing agent is a borate ion.

86 . The method of claim 82 wherein the amine moiety is formed by combining an unsubstituted amide moiety with an amine forming agent.

87 . The method of claim 86 wherein the amine forming agent is selected from the group consisting of bromine, bromide, bromite, hypobromite, chlorine, chloride, chlorite, hypochlorite, lead tetraacetate, benzyltrimethylammonium tribromide, [bis(trifluoroacetoxy)iodo]benzene, hydroxy(tosyloxy)iodobenzene and iodosylbenzene.

88 . The method of claim 48 wherein the chemical moiety of the biomolecule is a primary amine moiety.

89 . The method of claim 88 wherein the primary amine moiety is formed by combining an unsubstituted amide moiety with an amine forming agent.

90 . The method of claim 89 wherein the amine forming agent is selected from the group consisting of bromine, bromide, bromite, hypobromite, chlorine, chloride, chlorite, hypochlorite, lead tetraacetate, benzyltrimethylammonium tribromide, [bis(trifluoroacetoxy)iodo]benzene, hydroxy(tosyloxy)iodobenzene and iodosylbenzene.

91 . A method of making a tissue heart valve comprising: (a) providing the heart valve; (b) providing a biomolecule, the biomolecule comprising an arginine, glycine and aspartic acid amino acid sequence; and (c) reacting a chemical moiety of the biomolecule with a chemical moiety of the tissue heart valve to form a chemical bond, the chemical bond immobilizing the biomolecule on the surface of the tissue heart valve.

92 . The method of claim 91 wherein the biomolecule is a naturally occurring biomolecule.

93 . The method of claim 91 wherein the biomolecule is a chemically synthesized biomolecule.

94 . The method of claim 91 wherein the biomolecule is a peptide.

95 . The method of claim 94 wherein the peptide is a cell attachment peptide.

96 . The method of claim 91 wherein the biomolecule is a protein.

97 . The method of claim 96 wherein the protein is a cell attachment protein.

98 . The method of claim 96 wherein the protein is fibrinogen.

98 . The method of claim 96 wherein the protein is fibronectin.

99 . The method of claim 96 wherein the protein is vitronectin.

100 . The method of claim 96 wherein the protein is collagen.

101 . The method of claim 91 wherein the heart valve is implantable in a heart.

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