Compositions comprising bioadhesives and methods of making the same

Patent metadata

Field	Value
Publication number	US-9642933-B2
Application number	US-201313753683-A
Country	US
Kind code	B2
Filing date	Jan 30, 2013
Priority date	Jan 30, 2012
Publication date	May 9, 2017
Grant date	May 9, 2017

Abstract

In one aspect, compositions are described herein. In some embodiments, a composition comprises a polymer or oligomer formed from one or more polycarboxylic acids, one or more alcohols, and one or more catechol-containing species. In another aspect, methods of making a composition are described herein. In some embodiments, a method of making a composition comprises providing a polycarboxylic acid; providing an alcohol; combining the polycarboxylic acid with the alcohol; adding a catechol-containing species to the combination of the polycarboxylic acid and the alcohol; and forming a polymer or oligomer from the polycarboxylic acid, the alcohol, and the catechol-containing species. In some embodiments, the catechol-containing species comprises an amine moiety, a carboxylic acid moiety, or a hydroxyl moiety that is not part of the catechol group.

First claim

That which is claimed is:

1. A composition comprising:
a polymer or oligomer that is the polymerization or oligomerization product of one or more monomers of Formula (A), one or more monomers of Formula (B) or (B′), and one or more monomers of Formula (C):

wherein
R 1 , R 2 , and R 3
are independently —H, —CH 3 , or —CH 2 CH 3 ;

R 4 is —H, —OH, —OCH 3 , —OCH 2 CH 3 , —CH 3 , or —CH 2 CH 3 ;
R 5 is —H, —CH 3 , or —CH 2 CH 3 ;
R 6 , R 7 , R 8 , and R 9
are independently —H, —CH 2 (CH 2 ) x NH 2 , —CH 2 (CHR 10 )NH 2 , or —CH 2 (CH 2 ) x COOH;

R 10 is —COOH or —(CH 2 ) y COOH;
n and m
are independently integers ranging from 1 to 20;

x is an integer ranging from 0 to 20; and
y is an integer ranging from 1 to 20;

wherein the polymer or oligomer is crosslinked to form a polymer network, wherein at least one crosslink in the crosslinked polymer or oligomer comprises two catechol moieties directly and covalently coupled to each other.

2. The composition of claim 1 , wherein a monomer of Formula (C) comprises dopamine or L-DOPA.

3. The composition of claim 1 further comprising a particulate material mixed with the polymer or oligomer.

4. The composition of claim 1 further comprising a drug mixed with the polymer or oligomer.

5. The composition of claim 4 , wherein the polymer or oligomer is in nanoparticulate form.

6. The composition of claim 1 , wherein the polymer or oligomer is bonded to a surface.

7. A method of making a composition of claim 1 comprising:
providing a polycarboxylic acid of one or more monomers of Formula (A):

providing an alcohol of one or more monomers of Formula (B) or (B′):

combining the polycarboxylic acid with the alcohol;
adding a catechol-containing species to the combination of the polycarboxylic acid and the alcohol, the catechol-containing species of one or more monomers of Formula (C):

wherein
R 1 , R 2 , and R 3
are independently —H, —CH 3 , or —CH 2 CH 3 ;

R 4 is —H, —OH, —OCH 3 , —OCH 2 CH 3 , —CH 3 , or —CH 2 CH 3 ;
R 5 is —H, —CH 3 , or —CH 2 CH 3 ;
R 6 , R 7 , R 8 , and R 9
are independently —H, —CH 2 (CH 2 ) x NH 2 , —CH 2 (CHR 10 )NH 2 , or —CH 2 (CH 2 ) x COOH;

R 10 is —COOH or —(CH 2 ) y COOH;
n and m
are independently integers ranging from 1 to 20;

x is an integer ranging from 0 to 20; and
y is an integer ranging from 1 to 20; and

forming a polymer or oligomer from the polycarboxylic acid, the alcohol, and the catechol-containing species,
wherein the polymer or oligomer is crosslinked to form a polymer network, wherein at least one crosslink in the crosslinked polymer or oligomer comprises two catechol moieties directly and covalently coupled to each other.

8. The method of claim 7 further comprising adding a particulate material to the polymer or oligomer.

9. The method of claim 7 further comprising adding a drug to the polymer or oligomer.

10. The method of claim 7 further comprising forming nanoparticles of the polymer network.

11. A method of adhering biological tissue comprising:
disposing the composition of claim 1 between a first portion of biological tissue and
a second portion of biological tissue.

12. The method of claim 11 further comprising contacting the first portion of biological tissue with the second portion of biological tissue.

13. A method of treating disease comprising disposing the composition of claim 4 in a biological compartment.

14. The method of claim 13 further comprising releasing the drug of the composition into the biological compartment.

15. A method of promoting biological tissue growth comprising:
providing a scaffold comprising the composition of claim 3 ; and
disposing the scaffold in a tissue growth medium.

16. The composition of claim 3 , wherein the particulate material is selected from the group consisting of hydroxyapatite, tricalcium phosphate, biphasic calcium phosphate, bioglass, ceramic, magnesium powder, magnesium alloy, and decellularized bone tissue particles.

17. A composition comprising:
a polymer or oligomer bonded to a surface of an inorganic material, wherein the polymer or oligomer is the polymerization or oligomerization product of one or more monomers of Formula (A), one or more monomers of Formula (B) or (B′), and one or more monomers of Formula (C):

wherein
R 1 , R 2 , and R 3
are independently —H, —CH 3 , or —CH 2 CH 3 ;

R 4 is —H, —OH, —OCH 3 , —OCH 2 CH 3 , —CH 3 , or —CH 2 CH 3 ;
R 5 is —H, —CH 3 , or CH 2 CH 3 ;
R 6 , R 7 , R 8 , and R 9
are independently —H, —CH 2 (CH 2 ) x NH 2 , —CH 2 (CHR 10 )NH 2 , or —CH 2 (CH 2 ) x COOH;

R 10 is —COOH or —(CH 2 ) y COOH;
n and m
are independently integers ranging from 1 to 20;

x is an integer ranging from 0 to 20; and
y is an integer ranging from 1 to 20;

wherein the polymer or oligomer is crosslinked to form a polymer network,
wherein at least one crosslink in the crosslinked polymer or oligomer comprises two catechol moieties directly and covalently coupled to each other, and
wherein the polymer or oligomer is bonded to the surface of the inorganic material.

18. The composition of claim 17 , wherein a monomer of Formula (C) comprises dopamine or L-DOPA.

19. The composition of claim 17 , wherein the polymer or oligomer is crosslinked to form a polymer network.

20. The composition of claim 19 , wherein the polymer or oligomer is crosslinked through one or more catechol moieties.

21. The composition of claim 17 , further comprising a particulate material mixed with the polymer or oligomer.

22. The composition of claim 21 , wherein the particulate material is selected from the group consisting of hydroxyapatite, tricalcium phosphate, biphasic calcium phosphate, bioglass, ceramic, magnesium powder, magnesium alloy, and decellularized bone tissue particles.

23. The composition of claim 17 , further comprising a drug mixed with the polymer or oligomer.

24. The composition of claim 17 , wherein the inorganic material is a mineral or oxide material.

Assignees

• Univ Texas
• Univ Texas

Inventors

• Yang Jian
• Mehdizadeh Mohammadreza

Classifications

• A61L27/58

  Materials at least partially resorbable by the body · CPC title

• A61L24/0042

  Materials resorbable by the body · CPC title

• A61L2400/12

  Nanosized materials, e.g. nanofibres, nanoparticles, nanowires, nanotubes; Nanostructured surfaces · CPC title

• C08G63/668

  derived from polycarboxylic acids and polyhydroxy compounds · CPC title

• A61L24/0031

  Hydrogels or hydrocolloids · CPC title