CA2451624A1 - Compositions and systems for forming crosslinked biomaterials and associated methods of preparation and use - Google Patents

Compositions and systems for forming crosslinked biomaterials and associated methods of preparation and use Download PDF

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CA2451624A1
CA2451624A1 CA002451624A CA2451624A CA2451624A1 CA 2451624 A1 CA2451624 A1 CA 2451624A1 CA 002451624 A CA002451624 A CA 002451624A CA 2451624 A CA2451624 A CA 2451624A CA 2451624 A1 CA2451624 A1 CA 2451624A1
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groups
component
group
hydrophilic polymer
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CA2451624C (en
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Olof Mikael Trollsas
Donald G. Wallace
Frank A. Delustro
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Angiodevice International GmbH
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
    • A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
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    • A—HUMAN NECESSITIES
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    • A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
    • A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
    • A61L24/046—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
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    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
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    • A61L27/34—Macromolecular materials
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    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
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    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/04—Macromolecular materials
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    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L31/16—Biologically active materials, e.g. therapeutic substances
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    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
    • C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
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    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
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    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
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    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/02—Polythioethers
    • C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
    • C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
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    • C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/003—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
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    • C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
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    • C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
    • C09J151/003—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
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    • C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
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Abstract

Crosslinkable compositions are provided that readily crosslinkin situ to provide biocompatible, nonimmunogenic crosslinked biomaterials. The compositions contain at least three biocompatible, nonimmunogenic components having reactive functional groups thereon, with the functional groups select ed so as to enable inter-reaction between the components, i.e., crosslinking. I n a preferred embodiment, a first component is polynucleophilic, a second component is polyelectrophilic, and at least one third component contains on e or more functional groups reactive with the nucleophilic moieties one the first or second component. At least one of the components is a polyfunctiona l hydrophilic polymer; the other components may also comprise hydrophilic polymers, or they may be low molecular weight, typically hydrophobic, crosslinkers. Methods for preparing and using the compositions are also provided. Exemplary uses include tissue augmentation, biologically active agent delivery, bioadhesion, and prevention of adhesions following surgery o r injury.

Claims (86)

1. A crosslinkable composition comprised of:
(a) a first crosslinkable component A having m nucleophilic groups, wherein m>=2;
(b) a second crosslinkable component B having n electrophilic groups capable of reaction with the m nucleophilic groups to form covalent bonds, wherein n >= 2 and m+n>4;and (c) a third crosslinkable component C having at least one functional group selected from (i) nucleophilic groups capable of reacting with the electrophilic groups of component B and (ii) electrophilic groups capable of reacting with the nucleophilic groups of component A, wherein the total number of functional groups on component C is represented by p, such that m + n + p > 5 wherein each of components A, B and C is biocompatible and nonimmunogenic, and at least one of components A, B and C is comprised of a hydrophilic polymer, and crosslinking of the composition results in a biocompatible, nonimmunogenic, crosslinked matrix.
2. The composition of claim 1, wherein p >= 2.
3. The composition of claim 1, wherein the m nucleophilic groups are identical.
4. The composition of claim 2, wherein the m nucleophilic groups are identical.
5. The composition of claim 1, wherein at least two of the m nucleophilic groups are different.
6. The composition of claim 1, wherein the n electrophilic groups are identical.
7. The composition of claim 4, wherein the n electrophilic groups are identical.
8. The composition of claim 1, wherein at least two of the n electrophilic groups are different.
9. The composition of claim 1, wherein the at least one functional group on component C
is nucleophilic.
10. The composition of claim 4, wherein the functional groups on component C
are nucleophilic.
11. The composition of claim 10, wherein the functional groups on component C
are the same as the m nucleophilic groups on component A.
12. The composition of claim 10, wherein at least one of the functional groups on component C is different than the m nucleophilic groups on component A.
13. The composition of claim 1, wherein the at least one functional group on component C is electrophilic.
14. The composition of claim 13, wherein the functional groups on component C
are electrophilic.
15. The composition of claim 14, wherein the functional groups on component C
are the same as the n electrophilic groups on component B.
16. The composition of claim 14, wherein at least one functional group on component C is different than the n electrophilic groups on component B.
17. The composition of claim 1, wherein component A has the structural formula (I), component B has the structural formula (II), and component C has the structural formula (III) (I) R1(-[Q1]q-X)m (II) R2(-[Q2]r-Y)n (III) R3(-[Q3]s-Fn)P
wherein:
R1, R2 and R3 are independently selected from the group consisting of C2 to hydrocarbyl, heteroatom-containing C2 to C14 hydrocarbyl, hydrophilic polymers, and hydrophobic polymers, providing that at least one of R1, R2 and R3 is a hydrophilic polymer;
X represents one of the m nucleophilic groups of component A;
Y represents one of the n electrophilic groups of component B;

Fn represents a functional group on component C;
Q1, Q2 and Q3 are linking groups;
q, r and s are independently zero or 1; and m, n and p are as defined previously.
18. The composition of claim 17, wherein at least one of R1, R2 and R3 is a synthetic hydrophilic polymer.
19. The composition of claim 17, wherein:
(a) R1 is a first synthetic hydrophilic polymer;
(b) R2 is selected from the group consisting of (i) a second synthetic hydrophilic polymer that may or may not be the same as R1 and (ii) C2 to C14 hydrocarbyl groups containing zero to 2 heteroatoms selected from N, O and S; and (c) R3 is selected from the group consisting of (i) a third synthetic hydrophilic polymer that may or may not be the same as R1 or R2 and (ii) C2 to C14 hydrocarbyl groups containing zero to 2 heteroatoms selected from N, O, S and combinations thereof.
20. The composition of claim 18, wherein the synthetic hydrophilic polymer is of a linear, branched, dendrimeric, hyperbranched, or star polymer.
21. The composition of claim 19, wherein the synthetic hydrophilic polymer is selected from the group consisting of: polyalkylene oxides; polyglycerols;
poly(oxyalkylene)-substituted polyols; polyacrylic acid and analogs thereof; polymaleic acid;
polyacrylamides; poly(olefinic alcohol)s; poly(N-vinyl lactams); polyoxazolines; polyvinylamines; and copolymers thereof.
22. The composition of claim 21, wherein the synthetic hydrophilic polymers is a polyalkylene oxide or polyglycerol.
23. The composition of 22, wherein the synthetic hydrophilic polymer is a polyalkylene oxide is selected from the group consisting of polyethylene glycol and polyethylene oxide)-polypropylene oxide) copolymers.
24. The composition of claim 23, wherein the polyalkylene oxide is polyethylene glycol.
25. The composition of claim 21, wherein the synthetic hydrophilic polymer is a poly(oxyalkylene)-substituted diol or polyol.
26. The composition of claim 25, wherein the synthetic hydrophilic polymer is selected from the group consisting of mono-poly(oxyalkylene)-substituted propylene glycol, di-(polyoxyalkylene)-substituted propylene glycol, mono-poly(oxyalkylene)-substituted trimethylene glycol, di-(polyoxyalkylene)-substituted trimethylene glycol, mono-poly(oxyalkylene)-substituted glycerol, di-(polyoxyalkylene)-substituted glycerol, and tri-(polyoxyalkylene)-substituted glycerol.
27. The composition of claim 21, wherein the synthetic hydrophilic polymer is selected from the group consisting of poly(acrylic acid) and analogs and copolymers thereof.
28. The composition of claim 27, wherein the synthetic hydrophilic polymer is selected from the group consisting of poly(acrylic acid), poly(methacrylic acid), poly(hydroxyethylmethacrylate), poly(hydroxyethylacrylate), poly(methylalkylsulfoxide acrylates), poly(methylalkylsulfoxide methacrylates), and copolymers thereof.
29. The composition of claim 21, wherein the synthetic hydrophilic polymer is polymaleic acid.
30. The composition of claim 21, wherein the synthetic hydrophilic polymer is a polyacrylamide.
31. The composition of claim 30, wherein the synthetic hydrophilic polymer is selected from the group consisting of polyacrylamide, poly(methacrylamide), poly(dimethylacrylamide), poly(N-isopropylacrylamide), and copolymers thereof.
32. The composition of claim 21, wherein the synthetic hydrophilic polymer is a poly(olefinic alcohol).
33. The composition of claim 32, wherein the poly(olefinic alcohol) is polyvinyl alcohol or a copolymer thereof.
34. The composition of claim 21, wherein the synthetic hydrophilic polymer is a poly(N-vinyl lactam).
35. The composition of claim 34, wherein the poly(N-vinyl lactam) is selected from the group consisting of polyvinyl pyrrolidone), polyvinyl caprolactam), and copolymers thereof.
36. The composition of claim 19, wherein at least one of R2 and R3 is C2 to hydrocarbyl containing zero to 2 heteroatoms selected from N, O and S.
37. The composition of claim 36, wherein at least one of R2 and R3 is C2 to hydrocarbyl.
38. The composition of claim 19, wherein r, s and t are zero.
39. The composition of claim 19, wherein at least one of r, s and t is 1.
40. The composition of claim 19, wherein one or more of Q1, Q2 and Q3 contains at least one biodegradable linkage.
41. The composition of claim 40, wherein the biodegradable linkage is a hydrolyzable linkage.
42. The composition of claim 40, wherein the biodegradable linkage is an enzymatically cleavable linkage.
43. The composition of claim 41, wherein the biodegradable linkage is an enzymatically hydrolyzable linkage.
44. The composition of claim 1, wherein the nucleophilic groups on component A
and any nucleophilic groups on component C are selected from the group consisting of -NH2, -NHR4, -N(R4)2, -SH, -OH, -COOH, -C6H4-OH, -PH2, -PHR5, -P(R5)2, -NH-NH2, -CO-NH-NH2, and -C5H4N, wherein R4 and R5 are C1-C12 hydrocarbyl.
45. The composition of claim 44, wherein the nucleophilic groups are selected from -NH2 and -NHR4 where R4 is lower hydrocarbyl.
46. The composition of claim 45, wherein the electrophilic groups on component B and any electrophilic groups on component C are amino-reactive groups.
47. The composition of claim 46, wherein the amino-reactive groups contain an electrophilically reactive carbonyl group susceptible to nucleophilic attack by a primary or secondary amine.
48. The composition of claim 47, wherein the amino-reactive groups are carboxylic acid esters.
49. The composition of claim 47, wherein the amino-reactive groups are carboxylic acids or aldehydes.
50. The composition of claim 46, wherein the amino-reactive groups are selected from the group consisting of succinimidyl ester, sulfosuccinimidyl ester, maleimido, epoxy, isocyanato, thioisocyanato, and ethenesulfonyl.
51. The composition of claim 44, wherein the nucleophilic groups are sulfhydryl groups.
52. The composition of claim 51, wherein the electrophilic groups on component B and any electrophilic groups on component C are sulfhydryl-reactive groups.
53. The composition of claim 52, wherein the sulfhydryl-reactive groups are selected so as to form a thioester, thioether, or disulfide linkage upon reaction with the sulfhydryl groups.
54. The composition of claim 52, wherein the sulfhydryl-reactive groups contain an electrophilically reactive carbonyl group susceptible to nucleophilic attack by sulfhydryl group.
55. The composition of claim 54, wherein the sulfhydryl-reactive groups are carboxylic acid esters.
56. The composition of claim 54, wherein the amino-reactive groups are carboxylic acids or aldehydes.
57. The composition of claim 52, wherein the sulfhydryl-reactive groups have the structure -S-S-Ar where Ar is a substituted or unsubstituted nitrogen-containing heteroaromatic moiety or a non-heterocyclic aromatic group substituted with an electron-withdrawing moiety.
58. The composition of claim 52, wherein the sulfhydryl-reactive groups are selected from the group consisting of succinimidyl ester, sulfosuccinimidyl ester, maleimido, epoxy, and ethenesulfonyl.
59. The composition of claim 1, further including at least one additional crosslinkable component D having at least one functional group selected from nucleophilic groups and electrophilic groups, and the total number of functional groups on component D
is represented by q, such that q >= 1.
60. The composition of claim 48, wherein q >= 2.
61. A crosslinkable composition comprising a plurality of biocompatible, non-immunogenic reactive compounds each comprised of a molecular core having at least one functional group attached thereto through a direct covalent bond or through a linking group, wherein under reaction-enabling conditions each reactive compound is capable of substantially immediate covalent reaction with at least one other of the plurality of reactive compounds by virtue of the at least one functional group, and further wherein:
each molecular core is selected from the group consisting of synthetic hydrophilic polymers, naturally occurring hydrophilic polymers, hydrophobic polymers, and hydrocarbyl groups containing zero to 2 heteroatoms selected from N, O, S and combinations thereof;
at least one of the molecular cores is a synthetic hydrophilic polymer; and at least two of the molecular cores contain at least two functional groups.
62. A crosslinkable composition comprising a plurality of biocompatible, non-immunogenic reactive compounds each comprised of a molecular core having at least two functional groups covalently attached thereto, wherein under reaction-enabling conditions each reactive compound is capable of substantially immediate covalent reaction with at least one other of the plurality of reactive compounds by virtue of the at least two functional groups, and further wherein:
each molecular core is selected from the group consisting of synthetic hydrophilic polymers and C2-C14 hydrocarbyl groups containing zero to 2 heteroatoms selected from N, O and combinations thereof; and at least one of the molecular cores is a synthetic hydrophilic polymer.
63. A crosslinkable composition comprising a plurality of biocompatible, non-immunogenic reactive compounds each comprised of: a molecular core selected from the group consisting of synthetic hydrophilic polymers and C2-C14 hydrocarbyl groups containing zero to 2 heteroatoms selected from N, O, S and combinations thereof, with the proviso that at least one of the reactive compounds has a molecular core composed of a synthetic hydrophilic polymer; at least two functional groups attached to each molecular core through a direct covalent bond or through a linking group, wherein the functional groups of at least one of the reactive compounds are hydroxyl or sulfhydryl groups and the functional groups of at least one other of the reactive compounds are electrophilic groups capable of undergoing reaction with the hydroxyl or sulfhydryl groups to form covalent bonds, such that upon admixture of the composition with an aqueous base, a biocompatible, non-immunogenic crosslinked material is formed.
64. A crosslinkable composition comprising at least three biocompatible, non-immunogenic reactive compounds, wherein a first of said reactive compounds is comprised of a synthetic hydrophilic polymer having at least two functional groups attached thereto, a second of said reactive compounds is comprised of a C2-C14 hydrocarbyl group containing zero to 2 heteroatoms selected from N, O, S and combinations thereof, with at least two functional groups attached thereto, and a third of said reactive compounds is comprised of a naturally occurring hydrophilic polymer with at least two functional groups attached thereto, wherein the functional groups of at least one of the reactive compounds are hydroxyl or sulfhydryl groups and the functional groups of at least one other of the reactive compounds are electrophilic groups capable of undergoing reaction with the hydroxyl or sulfhydryl groups to form a covalent bond, such that upon admixture of the composition with an aqueous base, a biocompatible, non-immunogenic crosslinked material is formed.
65. A crosslinkable composition comprising at least three biocompatible, non-immunogenic compounds each capable of reacting with at least one other of said compounds upon admixture of the composition with an aqueous medium to form a covalently crosslinked material, wherein: a first compound comprises a synthetic hydrophilic polymer having at least two primary amino groups attached thereto; a second compound comprises a synthetic hydrophilic polymer having at least two amine-reactive electrophilic groups attached thereto; and a third compound comprises a C2-C14 hydrocarbyl group containing zero to 2 heteroatoms selected from N, O, S and combinations thereof, and substituted with at least one functional group capable of undergoing reaction with the primary amino groups or the amine-reactive electrophilic groups.
66. A crosslinkable composition comprising at least three biocompatible, non-immunogenic compounds each capable of reacting with at least one other of said compounds upon admixture of the composition with an aqueous medium to form a covalently crosslinked material, wherein: a first compound comprises a synthetic hydrophilic polymer having at least two sulfhydryl groups attached thereto; a second compound comprises a synthetic hydrophilic polymer having at least two sulfhydryl-reactive electrophilic groups attached thereto;
and a third compound comprises a C2-C14 hydrocarbyl group containing zero to 2 heteroatoms selected from N, O and combinations thereof, and substituted with at least one functional group capable of undergoing reaction with the sulfhydryl groups or the sulfhydryl-reactive groups.
67. A crosslinked composition prepared by admixing the composition of claim 1 with an aqueous solution, with the proviso that if the nucleophilic groups on component A or the functional groups on component C are hydroxyl or thiol groups, the aqueous solution contains a base.
68. The composition of claim 67, wherein the base is a non-nucleophilic base.
69. The composition of claim 67, further including a therapeutically effective amount of a biologically active agent.
70. The composition of claim 69, wherein the biologically active agent is selected from the group consisting of: enzymes, receptor antagonists, receptor agonists, hormones, growth factors, autogeneous bone marrow, antibiotics, antimicrobial agents, antibodies, cells and genes.
71. The composition of claim 70, wherein the biologically active agent is a growth factor or a derivative, analog or fragment thereof.
72. The composition of claim 70, wherein the biologically active agent is a cell.
73. The composition of claim 70, wherein the biologically active agent is a gene.
74. A crosslinkable system comprised of (a) a first crosslinkable component A having m nucleophilic groups, wherein m >= 2;
(b) a second crosslinkable component B having n electrophilic groups capable of reaction with the m nucleophilic groups to form covalent bonds, wherein n >= 2 and m + n > 4; and (c) at least one additional crosslinkable component C having at least one functional group selected from (i) nucleophilic groups capable of reacting with the electrophilic groups of component B and (ii) electrophilic groups capable of reacting with the nucleophilic groups of component A, wherein the total number of functional groups on component C is represented by p, such that m + n + p > 5, wherein each crosslinkable component is biocompatible, nonimmunogenic, and physically segregated from each other crosslinkable component, and at least one of the crosslinkable components A, B and C is comprised of a hydrophilic polymer, and crosslinking of the composition results in a biocompatible, nonimmunogenic, crosslinked matrix.
75. The crosslinkable system of claim 74, wherein component A is contained in a sterile aqueous medium.
76. A method for effecting the nonsurgical attachment of a first surface to a second surface, comprising the steps of:
providing the crosslinkable system of claim 74;
admixing the crosslinkable components in a sterile aqueous medium to provide a mixture and initiate crosslinking, and, immediately thereafter, applying the mixture to the first surface; and contacting the first surface with a second surface to effect adhesion therebetween.
77. The method of claim 76, wherein one of the first and second surfaces is a native tissue surface and the other of the first and second surfaces is selected from a non-native tissue surface and the surface of a synthetic implant.
78. The method of claim 76, wherein the first and second surfaces are native tissue surfaces.
79. A method for effecting the augmentation of tissue within the body of a mammalian subject, comprising the steps of:
providing the crosslinkable system of claim 74;
administering the components of the crosslinkable system to a tissue site in need of augmentation; and allowing the components to crosslink in situ to provide tissue augmentation.
80. The method of claim 79, wherein the components of the crosslinkable system are admixed prior to administration to the tissue site.
81. The method of claim 79, wherein the components are separately administered to the tissue site.
82. The method of claim 79, wherein the tissue is soft tissue.
83. The method of claim 79, wherein the tissue is hard tissue.
84. A method for preventing the formation of adhesions following surgery or injury, comprising the steps of:
providing the crosslinkable system of claim 74;
admixing the crosslinkable components in a sterile aqueous medium to provide a mixture and initiate crosslinking, and, immediately thereafter, applying the mixture to a tissue comprising, surrounding, or adjacent to a wound before substantial crosslinking has occurred; and allowing the components to crosslink in situ.
85. The method of claim 84, further comprising effecting surgical closure of the wound.
86. A crosslinkable composition comprised of (a) at least one first component composed of branched polyglycerol containing two or more nucleophilic groups; and (b) at least one second component functionalized to contain two or more electrophilic groups capable of reaction with the nucleophilic groups to form covalent bonds, wherein upon admixture of the components in an aqueous medium, the composition crosslinks to provide a biocompatible, non-immunogenic, crosslinked material.
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