Contact lenses with mucin affinity
View Patent ↗A biomedical device, such as a contact lens, has a surface linked to a polymer comprising boronic acid moieties. The boronic acid monomeric units may be derived from an ethylenically unsaturated monomer containing a boronic acid moiety, such as a vinylphenyl boronic acid or a (meth)acrylamido phenyl boronic acid. The boronic acid moieties may be complexed with mucin, especially epithelial mucin.
1. An ophthalmic device comprising a surface coated with a polymer comprising boronic acid moieties and complexing with epithelial mucin.
2. The ophthalmic device of claim 1 , which is a contact lens.
3. The contact lens of claim 2 , wherein the polymer comprises monomeric units derived from an ethylenically unsaturated monomer containing a boronic acid moiety.
4. The contact lens of claim 3 , wherein the polymer comprises monomeric units derived from at least one member selected from the group consisting of: a vinylphenyl boronic acid and a methacrylamido phenyl boronic acid.
5. The contact lens of claim 4 , wherein the polymer further comprises monomeric units derived from an ethylenically unsaturated hydrophilic monomer.
6. The contact lens of claim 4 , wherein the polymer further comprises monomeric units derived from an ethylenically unsaturated monomer containing a tertiary-amine moiety.
7. The contact lens of claim 6 , wherein the ethylenically unsaturated monomer is a 2-(N,N-dimethyl)ethylamino(meth)acrylate, a 2-(N,N-dimethyl)ethylamino(meth)-acrylamide, a 2-(N,N-dimethyl)propylamino(meth)acrylate; a 3-(N,N-dimethyl)propylamino(meth)acrylamide, or a vinylbenzyl-N,N-dimethylamine.
8. The contact lens of claim 2 , wherein the polymer further comprises monomeric units derived from an ethylenically unsaturated monomer containing a moiety reactive with complementary reactive functionalities at the lens surface.
9. The contact lens of claim 8 , wherein the polymer is covalently linked to the lens surface with the moiety reactive with the complementary functionality at the lens surface.
10. The contact lens of claim 2 , wherein the polymer is a copolymer comprising: monomeric units derived from an ethylenically unsaturated monomer containing a boronic acid moiety; and monomeric units derived from an ethylenically unsaturated monomer containing a moiety reactive with complementary reactive functionalities at the lens surface.
11. The contact lens of claim 10 , wherein the polymer is a copolymer further comprising monomeric units derived from an ethylenically unsaturated monomer containing a tertiary-amine moiety.
12. The contact lens of claim 11 , wherein the polymer is a copolymer further comprising monomeric units derived from an ethylenically unsaturated hydrophilic monomer in an amount sufficient to render the copolymer water soluble.
13. The contact lens of claim 2 , wherein the polymer is covalently bound to the lens surface through primary amine or hydroxyl radicals at the lens surface.
14. The contact lens of claim 2 , wherein the polymer comprising boronic acid moieties is linked to the lens surface with an intermediate polymer reactive with both the lens surface and the polymer comprising boronic acid moieties.
15. The contact lens of claim 14 , wherein the intermediate polymer is covalently linked to the lens surface and to the polymer comprising boronic acid moieties.
16. The contact lens of claim 14 , wherein the polymer is a copolymer comprising: monomeric units derived from an ethylenically unsaturated monomer containing a boronic acid moiety; and monomeric units derived from an ethylenically unsaturated monomer containing a moiety reactive with complementary reactive functionalities of the intermediate polymer.
17. The contact lens of claim 16 , wherein the polymer is a copolymer further comprising monomeric units derived from an ethylenically unsaturated monomer containing a tertiary-amine moiety.
18. The contact lens of claim 17 , wherein the polymer is a copolymer further comprising monomeric units derived from an ethylenically unsaturated hydrophilic monomer in an amount sufficient to render the copolymer water soluble.
19. A method comprising coating a surface of an ophthalmic device with a polymer comprising boronic acid moieties, and placing the ophthalmic device in the eye, whereby epithelial mucin complexes with the polymer comprising boronic acid moieties.
20. The method of claim 19 , wherein the biomedical device is a contact lens.
21. The method of claim 20 , comprising placing the contact lens in the eye, whereby epithelial mucin complexes with the polymer comprising boronic acid moieties.
22. The method of claim 20 , wherein the polymer comprises reactive moieties that are covalently linked to complementary reactive functionalities on the lens surface.
23. The method of claim 20 , further comprising subjecting the surface of the lens to a plasma treatment that provides the complementary reactive functionalities on the lens surface.
24. The method of claim 20 , wherein an intermediate polymer is linked to the lens surface, and the polymer comprising boronic acid moieties is linked to the intermediate polymer.
25. The method of claim 24 , wherein the intermediate polymer is reactive with reactive functionality on the lens surface and reactive functionalities on the polymer comprising boronic acid moieties.
26. The method of claim 20 , further comprising subjecting the surface of the lens to a plasma treatment that provides complementary reactive functionalities on the lens surface for the intermediate polymer.
27. An ophthalmic device coated with a copolymer comprising moieties that complex with epithelial mucin, said copolymer having greater affinity to epithelial mucin than to lysozyme.
28. The ophthalmic device of claim 27 , which is a contact lens.
29. The ophthalmic device of claim 27 , which is a contact lens coated with a copolymer comprising boronic acid moieties.