Crosslinkable polysaccharides, polycations and lipids useful for encapsulation and drug release
First Claim
1. A modified biocompatible material having the formula:
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space="preserve" listing-type="equation">A--Xwherein;
a) A is a biocompatible starting material selected from a polysaccharide, polycation, or lipid;
b) X is a moiety containing a carbon--carbon double bond or triple bond capable of undergoing free radical polymerization;
c) A and X are linked covalently through linkages selected from ester, ether, thioether, disulfide, amide, secondary amines, tertiary amines, direct C--C linkages, sulfate esters, sulfonate esters, phosphate esters, urethanes, or carbonates;
d) said modified biocompatible material forms covalent crosslinks when subjected to biocompatible, free radical polymerization producing conditions in aqueous media consisting essentially of water and solutes, or consisting essentially of water, solutes, and a biocompatible oil; and
e) A--X is produced in aqueous media consisting essentially of water and solutes.
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Accused Products
Abstract
The present invention relates to a new form of biocompatible materials (e.g., lipids, polycations, polysaccharides) which are capable of undergoing free radical polymerization, e.g., by using certain sources of light; methods of modifying certain synthetic and naturally occurring biocompatible materials to make polymerizable microcapsules containing biological material coated with said polymerizable materials, composites of said polymerizable materials, methods of making microcapsules and encapsulating biological materials therein, and apparatus for making microcapsules containing biological cells (particularly islets of Langerhans) coated with polymerizable alginate or with a composite thereof (e.g., alginate and PEG). The present invention also relates to drug delivery systems relating to the foregoing, as well as bioadhesives and wound dressings made utilizing the foregoing technology.
114 Citations
29 Claims
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1. A modified biocompatible material having the formula:
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space="preserve" listing-type="equation">A--Xwherein; a) A is a biocompatible starting material selected from a polysaccharide, polycation, or lipid; b) X is a moiety containing a carbon--carbon double bond or triple bond capable of undergoing free radical polymerization; c) A and X are linked covalently through linkages selected from ester, ether, thioether, disulfide, amide, secondary amines, tertiary amines, direct C--C linkages, sulfate esters, sulfonate esters, phosphate esters, urethanes, or carbonates; d) said modified biocompatible material forms covalent crosslinks when subjected to biocompatible, free radical polymerization producing conditions in aqueous media consisting essentially of water and solutes, or consisting essentially of water, solutes, and a biocompatible oil; and e) A--X is produced in aqueous media consisting essentially of water and solutes. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16)
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14. A modified biocompatible material according to claim 13 wherein A is a polysaccharide selected from alginate, high M-content alginate, polymannuronic acid, polymannuronate, hyaluronic acid, chitosan, chitin, cellulose, starch, glycogen, guar gum, locust bean gum, dextran, levan, inulin, cyclodextran, agarose, xanthan gum, carageenan, heparin, pectin, gellan gum, or scleroglucan.
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15. A modified biocompatible material according to claim 14 wherein said polysaccharide is sulfonated.
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16. A crosslinked biocompatible material produced by subjecting said modified biocompatible material of claim 13 to ionic crosslinking and/or free radical polymerization conditions.
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17. A method for the free radical polymerization of biocompatible starting materials characterized by having a reactive functionality thereon, wherein said biocompatible starting materials are selected from polysaccharides, polycations, or lipids, said method comprising:
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chemically modifying said biocompatible starting material in aqueous media consisting essentially of water and solutes with a reactive species capable of free radical polymerization, thereby creating a modified biocompatible material capable of forming covalent crosslinks; and contacting said modified biocompatible material with a free radical initiating system under biocompatible, free radical producing conditions in aqueous media consisting essentially of water and solutes, or consisting essentially of water, solutes, and a biocompatible oil. - View Dependent Claims (18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28)
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29. A modified biocompatible material having the formula:
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space="preserve" listing-type="equation">A--Xwherein; a) A is selected from phosphatidylethanolamine, phosphatidylserine, phosphatidylinositol, phosphatidylglycerol or dilaurylphosphatidic acid; b) X is a moiety containing a carbon--carbon double bond or triple bond capable of undergoing free radical polymerization; c) A and X are linked covalently through linkages selected from ester, ether, thioether, disulfide, amide, secondary amines, tertiary amines, direct C--C linkages, sulfate esters, sulfonate esters, phosphate esters, urethanes, or carbonates; and d) said modified biocompatible material forms covalent crosslinks when subjected to biocompatible, free radical polymerization producing conditions in aqueous media consisting essentially of water and solutes, or consisting essentially of water, solutes, and a biocompatible oil.
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Specification