Instant underwater bio-adhesive containing catechol moieties and water-resistant cholesterol

Patent metadata

Field	Value
Publication number	US-12233182-B2
Application number	US-202217959091-A
Country	US
Kind code	B2
Filing date	Oct 3, 2022
Priority date	Oct 3, 2022
Publication date	Feb 25, 2025
Grant date	Feb 25, 2025

Abstract

A novel bio-adhesive suitable for in vivo and/or underwater medical use is disclosed. The bio-adhesive includes base polymers conjugated to hydrophobic moieties for imparting water-resistance and/or to phenolic moieties for enhancing adhesion to biological tissues. The bio-adhesive exhibits low toxicity and is highly compatible with biological tissues.

First claim

What is claimed is:

1. A bio-adhesive comprising a polyanionic polymer and a polycationic polymer functionalized with a hydrophobic moiety, wherein the functionalized polycationic polymer comprises a polycationic polymer having a hydrophobic moiety, wherein the bio-adhesive comprises:
from 15 to 60% by weight, based on a total weight of the bio-adhesive, of the functionalized polycationic polymer;
from 40 to 85% by weight, based on a total weight of the bio-adhesive, of the polyanionic polymer; or
from 15 to 60% by weight, based on a total weight of the bio-adhesive, of the functionalized polycationic polymer and from 40 to 85% by weight, based on a total weight of the bio-adhesive, of the polyanionic polymer.

2. The bio-adhesive of claim 1 , wherein the functionalized polycationic polymer comprises one or a combination of polyethyleneimine, chitosan, poly dimethyl diallyl ammonium chloride, and polyamidoamine-epichlorohydrin.

3. The bio-adhesive of claim 1 , wherein the hydrophobic moiety comprises one or a combination of a cholesterol, stearic acid, oleic acid, lecithin, sulfonate, [or] and a quaternary ammonium salt moiety.

4. The bio-adhesive of claim 1 , wherein the polyanionic polymer comprises a negatively-charged polysaccharide.

5. The bio-adhesive of claim 4 , wherein the negatively-charged polysaccharide comprises one or a combination of chondroitin sulfate, glycosaminoglycan, carrageenan, gum Arabic, alginate, xanthan, guar gum, pectin, sodium alginate, hyaluronic acid, gellan gum, and heparin.

6. The bio-adhesive of claim 1 , wherein the polyanionic polymer further comprises at least one phenolic moiety.

7. The bio-adhesive of claim 6 , wherein the phenolic moiety is selected from catechol, catechin, dopamine, levopamine, epicatechin, or a combination thereof.

8. A medical adhesive kit for adhering biological tissues comprising the bio-adhesive of claim 1 .

9. A method for preparing a bio-adhesive of claim 1 , the method comprising contacting a polycationic polymer comprising at least one hydrophobic moiety with a polyanionic polymer comprising at least one phenolic moiety to obtain the bio-adhesive.

10. The method of claim 9 , wherein the polycationic polymer comprises polyethyleneimine, chitosan, diallyl ammonium chloride, polyamidoamine-epichlorohydrin, or a combination thereof.

11. The method of claim 9 , wherein the hydrophobic moiety comprises a cholesterol, stearic acid, oleic acid, lecithin, sulfonate, or a quaternary ammonium salt moiety, or a combination thereof.

12. The method of claim 9 , wherein the polyanionic polymer comprises a negatively-charged polysaccharide comprising chondroitin sulfate, glycosaminoglycan, carrageenan, gum Arabic, alginate, xanthan, guar gum, pectin, sodium alginate, hyaluronic acid, gellan gum, heparin, or a combination thereof.

13. The method of claim 9 , wherein the phenolic moiety comprises catechol, catechin, dopamine, levopamine, epicatechin, or a combination thereof.

14. A method for adhering two surfaces, the method comprising contacting the bio-adhesive of claim 1 to a first surface to form a bio-adhesive coated surface and contacting the bio-adhesive coated surface with a second surface, wherein contacting the bio-adhesive coated surface with a second surface adheres the first and second surfaces.

15. The method of claim 14 , wherein the first and/or second surface is a surface of a biological material.

16. The method of claim 14 , wherein the first and/or second surface is a surface of a cartilage, bone, shell, claw, tooth, or nail.

17. The method of claim 14 , wherein the first surface is wet when contacted with the bio-adhesive and/or the second surface is wet when contacted with the bio-adhesive coated surface.

18. The method of claim 14 , wherein the method further comprises contacting the adhered first and second surface with water.

Assignees

• Univ City Hong Kong

Inventors

• Wang Dong-An
• Tao chao
• Jin Min

Classifications

• A61L2300/232

  Monosaccharides, disaccharides, polysaccharides, lipopolysaccharides · CPC title

• A61L24/0042

  Materials resorbable by the body · CPC title

• A61L24/06

  obtained by reactions only involving carbon-to-carbon unsaturated bonds {(A61L24/043, A61L24/046 take precedence)} · CPC title

• A61L24/08 Primary

  Polysaccharides {(A61L24/043 takes precedence)} · CPC title