Hydrophobic derivatives of natural biodegradable polysaccharides and uses thereof
Low molecular weight hydrophobic derivatives of non-cyclic α(1→4)glucopyranose polymers and non-reducing polysaccharides are described. The derivates can be used to form matrices in various forms, including body members of implantable articles, coatings, and consumer items, which have desirable properties.
1 . A hydrophobic derivative of a natural biodegradable polysaccharide comprising:
a non-cyclic poly-α(1→4)glucopyranose backbone; and
a plurality of groups pendent from the poly-α(1→4)glucopyranose backbone, the groups comprising a hydrocarbon segment comprising two or more carbon atoms;
wherein the hydrophobic derivative has a molecular weight of 100,000 Da or less.
2 . The hydrophobic derivative of claim 1 having a molecular weight 50,000 Da or less.
3 . The hydrophobic derivative of claim 2 wherein the hydrophobic derivative has a molecular weight of 25,000 Da or less.
4 . The hydrophobic derivative of claim 3 wherein the hydrophobic derivative has a molecular weight in the range of 2000 Da to 20,000 Da.
5 . The hydrophobic derivative of claim 4 wherein the hydrophobic derivative has a molecular weight in the range of 4000 Da to 10,000 Da.
6 . The hydrophobic derivative of claim 1 wherein the hydrocarbon segment is selected from the group consisting of linear, branched, and cyclic C 2 -C 18 groups.
7 . The hydrophobic derivative of claim 6 wherein the hydrocarbon segment is selected from the group consisting of linear, branched, and cyclic C 4 -C 10 groups.
8 . The hydrophobic derivative of claim 7 wherein the plurality of groups pendent from the poly-α(1→4)glucopyranose backbone provide a degree of substitution in the range of 2-3.
9 . The hydrophobic derivative of claim 7 wherein the hydrocarbon segment is selected from the group consisting of linear, branched, and cyclic C 5 -C 7 groups.
10 . The hydrophobic derivative of claim 7 wherein the hydrocarbon segment is selected from the group consisting of branched C 4 -C 8 alkyl groups.
11 . The hydrophobic derivative of claim 10 wherein the plurality of groups pendent from the poly-α(1→4)glucopyranose backbone provide a degree of substitution in the range of 0.5-1.5.
12 . The hydrophobic derivative of claim 7 wherein the hydrocarbon segment is an aromatic C 6 group.
13 . The hydrophobic derivative of claim 1 wherein the groups pendent from the poly-α(1→4)glucopyranose backbone are coupled to the backbone via hydrolyzable covalent bonds.
14 . The hydrophobic derivative of claim 1 wherein the groups pendent from the poly-α(1 →4)glucopyranose backbone are coupled to the backbone via hydrolyzable ester bonds.
15 . A hydrophobic derivative of a natural biodegradable polysaccharide comprising:
a non-cyclic poly-α(1→4)glucopyranose backbone; and
a plurality of groups pendent from the poly-α(1→4)glucopyranose backbone,
wherein the hydrophobic derivative has a molecular weight of 100,000 Da or less and a Tg of 35° C. or greater.
16 . The hydrophobic derivative of claim 15 having a Tg in the range of 40° C. to 65° C.
17 . A hydrophobic derivative of a natural biodegradable polysaccharide comprising:
a hydrophilic portion comprising a non-cyclic poly-α(1→4)glucopyranose backbone; and
a hydrophobic portion comprising a plurality of groups pendent from the poly-α(1→4)glucopyranose backbone,
wherein the weight ratio between the hydrophilic portion and the hydrophobic portion in the range of 5:1 to 1:1.25, and wherein the hydrophobic derivative has a molecular weight of 100,000 Da or less.
18 . The hydrophobic derivative of claim 17 wherein the weight ratio between the hydrophilic portion and the hydrophobic portion in the range of 2:1 to 1:1.25
19 . The hydrophobic derivative of claim 18 wherein the weight ratio between the hydrophilic portion and the hydrophobic portion in the range of 1:0.75 to 1:1.25
20 . The hydrophobic derivative of claim 19 wherein the weight ratio between the hydrophilic portion and the hydrophobic portion in the range of 1:1 to 1:1.25
21 . A hydrophobic derivative of a natural biodegradable polysaccharide comprising:
a non-cyclic poly-α(1→4)glucopyranose backbone; and
a plurality of groups pendent from the poly-α(1→4)glucopyranose backbone, the groups comprising a hydrocarbon segment, wherein at least a portion of the groups comprise a bioactive agent that is cleavable from the poly-α(1→4)glucopyranose backbone,
wherein the hydrophobic derivative has a molecular weight of 100,000 Da or less.
22 . The hydrophobic derivative of claim 21 wherein the bioactive agent is an anti-inflammatory agent.
23 . The hydrophobic derivative of claim 21 wherein the bioactive agent is an antiproliferative.
24 . The hydrophobic derivative of claim 21 wherein the bioactive agent is a steroid.
25 . The hydrophobic derivative of claim 21 wherein the bioactive agent comprises a carboxylate group.
26 . A hydrophobic derivative of a natural biodegradable polysaccharide comprising:
a polymeric backbone comprising non-reducing disaccharides; and
a plurality of groups pendent from the polymeric backbone,
wherein the hydrophobic derivative has a molecular weight of 100,000 Da or less.
27 . The hydrophobic derivative of claim 26 wherein the polymeric backbone is selected from the group consisting of polytrehalose, polysucrose, and polyalditol.