Bioadhesive composition formed using click chemistry

• US 8,034,396 B2
• Filed: 02/10/2009
• Issued: 10/11/2011
• Est. Priority Date: 04/01/2008
• Status: Active Grant

• Current Assignee: Covidien LP (Medtronic Plc)
• Original Assignee: Tyco Healthcare Group LP (Medtronic Plc)
• Inventors: Belcheva, Nadya, Kapiamba, Mbiya
• Primary Examiner(s): Yoon; Tae H
• Application Number:
  US12/368,415
• Publication Number:
  US 20090247651A1
• Time in Patent Office: 973 Days
• Field of Search: 528/319, 523/118, 606/214, 514/43, 514/93, 427/2.13, 602/12
• US Class Current: 427/2.13
• CPC Class Codes: A61L 24/043 Mixtures of macromolecular materials
• CPC Class Codes: A61P 41/00 Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution

Abstract

The present disclosure provides compositions which may be utilized as adhesives or sealants in medical and surgical applications. The compositions may, in embodiments, be formed from the cycloaddition reaction of a first component possessing at least one azide group with a second component possessing at least one alkyne group.

Claims

1. A method for adhering tissue comprising:

contacting a first component possessing at least two alkyne groups with a second component selected from the group consisting of N—

((2S,3R,4S,5S,6S)-4,5-diazido-6-(azidomethyl)-2-(benzyloxy)tetrahydro-2H-pyran-3-yl)acetamide, 4,4′

-diazido-2,2′

-stilbenedisulfonic acid disodium salt hydrate, (3R,4R,5S,6S)-4-azido-6-(azidomethyl)tetrahydro-2H-pyran-2,3,5-triol, 4,4′

-oxybis(azidobenzene), 4,4′

-sulfonylbis(azidobenzene), bis[2-(4-azidosalicylamido)ethyl]disulfide, 1,17-diazido-3,6,9,12,15-pentaoxaheptadecane, (2E,6E)-2,6-bis(4-azidobenzylidene)cyclohexanone, tetraazido-pentaerythritol ethoxylate, heptakis-6-azido-6-deoxy-beta-cyclodextrin, and combinations thereof;

catalyzing a polymerization of the first component and the second component to form a bioadhesive composition; and

adhering the bioadhesive composition to at least one tissue surface.

2. The method according to claim 1, wherein the first component comprises a core comprising a polyol having at least 2 functional groups.

3. The method according to claim 2, wherein the polyol is selected from the group consisting of polyethers, polyesters, polyether-esters, polyalkanols, and combinations thereof.

4. The method according to claim 2, wherein the polyol comprises a polyether selected from the group consisting of polyethylene glycol, polypropylene glycol, polybutylene glycol, polytetramethylene glycol, polyhexamethylene glycol, cyclodextrin-polyethylene glycols, polyacetals, and combinations thereof.

5. The method according to claim 2, wherein the polyol comprises a polyester selected from the group consisting of trimethylene carbonate, ε

-caprolactone, p-dioxanone, glycolide, lactide, 1,5-dioxepan-2-one, polybutylene adipate, polyethylene adipate, polyethylene terephthalate, and combinations thereof.

6. The method according to claim 2, wherein the polyol comprises a poly(ether-ester) block.

7. The method according to claim 1 wherein the first component has at least 2 arms.

8. The method according to claim 1, wherein the first component comprises a core comprising a polyrotaxane.

9. The method according to claim 1, wherein the first component is of a formula selected from the group consisting of

10. The method according to claim 1, wherein the polymerization of the first component and the second component is catalyzed by a copper catalyst selected from the group consisting of copper sulfate, copper iodide, and combinations thereof.

11. The method according to claim 10, wherein the copper catalyst is contacted with a buffer salt selected from the group consisting of acetates, citrates, malonates, tartarates, succinates, benzoates, ascorbates, phosphates, sulfates, nitrates, bicarbonates, carbonates, and combinations thereof.

12. The method according to claim 1, wherein the first component possesses additional functional groups selected from the group consisting of amino, alkoxy, carboxylic acids, carboxylic esters, ketones, ethers, amides, sulfones, sulfonamides, and combinations thereof.

13. The method according to claim 1, wherein the ratio of azide groups from the second component to alkyne groups from the first component is from about 1:

2.

14. The method according to claim 1, wherein the first component, optionally the second component, and optionally the catalyst, are in a solution.

15. The method according to claim 1, wherein the bioadhesive composition is formed prior to application to tissue.

16. The method according to claim 1, wherein the bioadhesive composition is formed in vivo.

17. The method according to claim 1, wherein the bioadhesive composition is of the following formula:

18. The method according to claim 1, wherein the bioadhesive composition further comprises at least one bioactive agent.

19. The method according to claim 1, further comprising contacting the bioadhesive composition with a second tissue surface.

20. The method according to claim 1, further comprising contacting the bioadhesive composition with an implant.

21. A method for adhering tissue comprising:

contacting a first component possessing at least two alkyne groups with a second component possessing at least two azide groups;

catalyzing a polymerization of the first component and the second component to form a bioadhesive composition; and

contacting the bioadhesive composition to at least one tissue surface so that the bioadhesive composition adheres to the at least one tissue surface,

wherein the first component and optionally the second component comprises a core comprising a polyol comprising a poly(ether-ester) block having at least about 2 functional groups.

22. A method for adhering tissue comprising:

contacting a first component possessing at least two alkyne groups with a second component possessing at least two azide groups;

catalyzing a polymerization of the first component and the second component to form a bioadhesive composition; and

contacting the bioadhesive composition to at least one tissue surface so that the bioadhesive composition adheres to the at least one tissue surface,

wherein the first component and optionally the second component comprises a core comprising a polyrotaxane.