DOPA-functionalized, branched, poly(aklylene oxide) adhesives
The invention describes DOPA functionalized, branched, polyalkylene oxide materials that are useful as adhesives.
1. A composition comprising the formula:
CA-[Z-PA-(L) a -(DHPD) b -(AA) c -PG] n (II)
wherein
CA is carbon;
each Z, independently, is a C1 to a C6 linear or branched, substituted or unsubstituted alkyl group or a bond;
each PA, independently, is a substantially poly(alkylene oxide) polyether;
each L, independently, optionally, is a linker or is a linking group selected from amide, ester, urea, carbonate or urethane linking groups;
each DHPD, independently, is a multihydroxy phenyl derivative;
each AA, independently, optionally, is an amino acid moiety,
each PG, independently, is an optional protecting group, and if the protecting group is absent, each PG is replaced by a hydrogen atom;
“a” has a value of 0 when L is a linking group or a value of 1 when L is a linker;
“b” has a value of one or more;
“c” has a value in the range of from 0 to about 20; and
“n” has a value of 4.
2. The composition of claim 1 , wherein each Z is a methylene.
3. The composition of claim 1 , wherein each PA is a polyethylene glycol polyether.
4. The composition of claim 1 , wherein the molecular weight of each of PA is between about 1,250 and about 12,500 daltons.
5. The composition of claim 1 , wherein each DHPD is dopamine, 3,4-dihydroxyphenyl alanine, 2-phenyl ethanol or 3,4-dihydroxyhydrocinnamic acid.
6. The composition of claim 5 , wherein “c” is zero.
7. The composition of claim 1 , wherein PG is a hydrogen atom.
8. The composition of claim 1 , wherein “a” is zero.
9. The composition of claim 1 , wherein “b” is 1, 2, 3 or 4.
10. The composition of claim 1 , wherein the li nking group is an amide, urea or urethane.
11. The composition of claim 5 , wherein “c” is 1, 2, 3 or 4.
12. The composition of claim 11 , wherein AA is lysine.
13. The composition of claim 11 , wherein PG is a hydrogen atom.
14. The composition of claim 11 , wherein “a” is zero.
15. The composition of claim 11 , wherein “b” is 1, 2, 3 or 4.
16. The composition of claim 11 , wherein the linking group is an amide, ester or urethane.
17. The composition of claim 5 , wherein “a” is 1 and each L is an alkylene dicarboxylic acid moiety.
18. The composition of claim 17 , wherein the alkylene dicarboxylic acid moiety is succinic acid.
19. The composition of claim 17 , wherein PG is a hydrogen atom.
20. The composition of claim 17 , wherein “b” is 1, 2, 3 or 4.
21. The composition of claim 1 , wherein the DHPD has at least 2 hydroxyl groups.
22. The composition of claim 1 , wherein the DHPD has 2 hydroxyl groups.
23. A method to adhere biological tissues together, comprising the step of administering to the tissue a sufficient amount of an adhesive material as claimed in claim 1 , such that the biological tissues remain adhered to each other.
24. A method of crosslinking the material as recited in claim 1 by reacting said hydroxyphenyl groups with an oxidant to yield hydroxyphenyl free radical species, such that the free radical species react to yield a crosslinkage comprising multiple hydroxyphenyl species.
25. The method of claim 24 , wherein the oxidant is a periodate.
26. The method of claim 24 , wherein the oxidant is NaIO 3 , FeCl 3 , H 2 O 2 , oxygen, an inorganic base, an organic base or an oxidase.
27. A cross linked macromolecular hydrogel comprising the formula:
CA-[Z-PA-(L) a -(DHPD) b -(AA) c -PG] n (II)
wherein
CA is a central atom that is carbon;
each Z, independently, is a C1 to a C6 linear or branched, substituted or unsubstituted alkyl group or a bond;
each PA, independently, is a substantially poly(alkylene oxide) polyether;
each L, independently, optionally, is a linker or is a linking group selected from amide, ester, urea, carbonate or urethane linking groups;
each DHPD, independently is a multihydroxy phenyl derivative;
each AA independently, optionally, is an amino acid moiety,
each PG, independently, is an optional protecting group, and if the protecting group is absent, each PG is replaced by a hydrogen atom;
“a” has a value of 0 when L is a linking group or a value of 1 when L is a linker;
“b” has a value of one or more;
“c” has a value in the range of from 0 to about 20; and
“n” has a value of 4, wherein at least one linkage is formed between two DHPD groups attached respectively to adjacent molecules.
28. A composition comprising the formula:
CA-[Z-PA-(L) a -(DHPD) b -(AA) c -PG] n (I)
wherein
CA is a central atom selected from carbon, oxygen, sulfur, nitrogen, or a secondary amine;
each Z, independently is a C1 to a C6 linear or branched, substituted or unsubstituted alkyl group or a bond;
each PA, independently, is a substantially poly(alkylene oxide) polyether;
each L, independently, optionally, is a linker or is a linking group selected from amide, ester, urea, carbonate or urethane linking groups;
each DHPD, independently, is a multihydroxy phenyl derivative;
each AA, independently, optionally, is an amino acid moiety,
each PG, independently, is an optional protecting group, and if the protecting group is absent, each PG is replaced by a hydrogen atom;
“a” has a value of 0 when L is a linking group or a value of 1 when L is a linker;
“b” has a value of one or more;
“c” has a value in the range of from 0 to about 20; and
“n” has a value from 3 to 15.
29. A cross linked macromolecular hydrogel comprising the formula:
CA-[Z-PA-(L) a -(DHPD) b -(AA) c -PG] n (I)
wherein
CA is a central atom selected from carbon, oxygen, sulfur, nitrogen, or a secondary amine;
each Z, independently is a C1 to a C6 linear or branched, substituted or unsubstituted alkyl group or a bond;
each PA, independently, is a substantially poly(alkylene oxide) polyether;
each L, independently, optionally, is a linker or is a linking group selected from amide, ester, urea, carbonate or urethane linking groups;
each DHPD, independently, is a multihydroxy phenyl derivative;
each AA, independently, optionally, is an amino acid moiety,
each PG, independently, is an optional protecting group, and if the protecting group is absent, each PG is replaced by a hydrogen atom;
“a” has a value of 0 when L is a linking group or a value of 1 when L is a linker;
“b” has a value of one or more;
“c” has a value in the range of from 0 to about 20; and
“n” has a value from 3 to 15, wherein at least one linkage is formed between two DHPD groups attached respectively to adjacent molecules.