Polymerizable biodegradable polymers including carbonate or dioxanone linkages
First Claim
1. A method for forming a polymeric, biocompatible coating on tissue comprising:
- a) applying to the tissue surface a polymerization initiator capable of initiating polymerization via free radical or cationic polymerization;
b) applying to the initiator-coated surface a solution of a biodegradable, polymerizable macromer with a solubility of at least one gram/liter in aqueous solutions at a temperature in the range between about 0 and 50°
C. comprising at least one water soluble region, at least one degradable region, and at least one functional group capable of being polymerized via free radical or cationic polymerization, wherein the polymerizable regions are separated from each other by at least one degradable region and wherein at least one degradable region is a carbonate or dioxanone region; and
c) polymerizing the macromer.
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Abstract
Water-soluble macromers including at least one hydrolysable linkage formed from carbonate or dioxanone groups, at least one water-soluble polymeric block, and at least one polymerizable group, and methods of preparation and use thereof are described. The macromers are preferably polymerized using free radical initiators under the influence of long wavelength ultraviolet light or visible light excitation. Biodegradation occurs at the linkages within the extension oligomers and results in fragments which are non-toxic and easily removed from the body. The macromers can be used to encapsulate cells, deliver prophylactic, therapeutic or diagnostic agents in a controlled manner, plug leaks in tissue, prevent adhesion formation after surgical procedures, temporarily protect or separate tissue surfaces, and adhere or seal tissues together.
363 Citations
23 Claims
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1. A method for forming a polymeric, biocompatible coating on tissue comprising:
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a) applying to the tissue surface a polymerization initiator capable of initiating polymerization via free radical or cationic polymerization;
b) applying to the initiator-coated surface a solution of a biodegradable, polymerizable macromer with a solubility of at least one gram/liter in aqueous solutions at a temperature in the range between about 0 and 50°
C. comprising at least one water soluble region, at least one degradable region, and at least one functional group capable of being polymerized via free radical or cationic polymerization, wherein the polymerizable regions are separated from each other by at least one degradable region and wherein at least one degradable region is a carbonate or dioxanone region; and
c) polymerizing the macromer. - View Dependent Claims (2, 3, 4, 5, 6, 7)
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8. A method for making a device for controlled release of a prophylactic, therapeutic or diagnostic agent comprising:
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a) mixing a prophylactic, therapeutic or diagnostic agent with a solution of a biodegradable, polymerizable macromer with a solubility of at least one gram/liter in aqueous solutions at a temperature between about 0 and 50°
C. comprising at least one water soluble region, at least one degradable region, and at least one functional group capable of being polymerized via free radical or cationic polymerization, wherein the polymerizable regions are separated from each other by at least one degradable region and wherein at least one degradable region is a carbonate or dioxanone region; and
b) polymerizing the macromer to incorporate the agent within the resulting polymer. - View Dependent Claims (9, 10, 11, 12, 13)
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14. A method for increasing the elasticity of a hydrophilic polymer gel comprising incorporating one or more carbonate linkages into a reactive polymer before gelation by reaction of the reactive groups, wherein the resulting polymer has a solubility in water of at least one gram/liter of an aqueous solution at a temperature in the range between about 0 and 50°
- C., is biodegradable, and wherein each reactive group is separated from each other reactive group by at least one degradable linkage.
- View Dependent Claims (15, 16)
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17. A method for improving the biodegradability of a carbonate-comprising chemically-reactive macromer, the method comprising:
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a) reacting a carbonate with a biocompatible compound which has a solubility of at least one gram/liter in aqueous solutions at a temperature in the range between about 0 and 50°
C., wherein the biocompatible compound comprises at least two hydroxyl groups to form a carbonate-comprising precursor, the reaction continuing for a sufficient time to ensure completion of the reaction and attainment of equilibrium among reacting species, and the carbonate providing a first biodegradable linkage;
b) adding to the carbonate-comprising precursor an excess of a first reagent to form a second biodegradable linkage, wherein the first reagent comprises a biodegradable moiety other than a carbonate; and
thenc) adding to the carbonate-comprising precursor a second reagent which forms at least one chemically-reactive group, thereby forming the chemically-reactive macromer, wherein the chemically reactive group of step c) is attached to the macromer via the biodegradable moiety of step b). - View Dependent Claims (18, 19, 20, 21, 22, 23)
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Specification