Antioxidant-based poly(anhydride-esters)

Patent metadata

Field	Value
Publication number	US-9862672-B2
Application number	US-201414894166-A
Country	US
Kind code	B2
Filing date	May 29, 2014
Priority date	May 29, 2013
Publication date	Jan 9, 2018
Grant date	Jan 9, 2018

Abstract

Certain embodiments of the invention provide antioxidant-based diacids and polymers comprising glycol groups as described herein, and methods of use thereof. In certain embodiments the polymers described herein are formulated as microspheres or hydrogels. Described herein is the chemical incorporation of antioxidants, e.g., coumaric acid, ferulic acid, and sinapic acid, into a polymer backbone for use, e.g., in applications for localized release and rapid delivery. As provided, the chemical composition of the linker molecules used (of which hold together two bioactives via ester linkages) may be used to vary the hydrophilicity of the polymer. The bioactive release rate may also be altered for a tunable release delivery system, allowing for increased bioactive release compared to other linkers previously utilized.

First claim

What is claimed is:

1. A polymer selected from:

wherein R 1 is OCH 3 and R 2 is H; R 1 is OCH 3 and R 2 is OCH 3 ; or R 1 is H and R 2 is H;
wherein y is 4 or more;
and wherein n is 2 or more.

2. The polymer of claim 1 , wherein R 1 is OCH 3 and R 2 is H.

3. The polymer of claim 1 , wherein R 1 is OCH 3 and R 2 is OCH 3 .

4. The polymer of claim 1 , wherein R 1 is H and R 2 is H.

5. A microsphere comprising the polymer as described in claim 1 .

6. A diacid selected from:

wherein R 1 is OCH 3 and R 2 is H; R 1 is OCH 3 and R 2 is OCH 3 ; or R 1 is H and R 2 is H; and
wherein y is 4 or more.

7. A pharmaceutical composition comprising the polymer as described in claim 1 and a pharmaceutically acceptable carrier.

8. A cosmetic comprising the polymer as described in claim 1 .

9. A sunscreen comprising the polymer as described in claim 1 .

10. A method of reducing oxidative stress in a cell of a mammal, preventing photodamage in skin of a mammal, and/or treating a disorder associated with oxidative stress in a mammal, comprising administering the polymer as described in claim 1 to the mammal.

11. The method of claim 10 , wherein the polymer is administered topically.

12. A hydrogel comprising a blend comprising (a) the polymer as described in claim 1 and (b) a hydrophilic polymer.

13. The hydrogel of claim 12 , wherein the hydrophilic polymer is selected from the group consisting of poly(N-vinyl-2-pyrrolidone), poly(vinyl alcohol), and poly(ethylene oxide).

14. The hydrogel of claim 13 , wherein the hydrophilic polymer is poly(N-vinyl-2-pyrrolidone).

15. The hydrogel of claim 12 , wherein the polymer as described in claim 1 is physically crosslinked with the hydrophilic polymer through hydrophobic interactions.

16. A method of making a hydrogel comprising blending and solvent casting (a) the polymer as described in claim 1 and (b) a hydrophilic polymer, under conditions that provide a hydrogel.

17. The method of claim 16 , further comprising crosslinking (a) the polymer as described in claim 1 with (b) the hydrophilic polymer, wherein the crosslinking is by ultraviolet radiation, gamma radiation, or a crosslinking agent.

18. A method for promoting wound healing in a mammal, comprising contacting the hydrogel as described in claim 12 with a wound of the mammal.

19. A method of therapeutically treating the skin of a mammal, comprising contacting the hydrogel as described in claim 12 with the skin of the mammal.

Assignees

• Univ Rutgers

Inventors

• Uhrich Kathryn
• Morano Michelle

Classifications

• A61K8/025

  Explicitly spheroidal or spherical shape · CPC title

• A61K8/37

  Esters of carboxylic acids · CPC title

• A61Q17/04

  Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations · CPC title

• C07C69/734 Primary

  Ethers · CPC title

• C08G63/06 Primary

  derived from hydroxycarboxylic acids · CPC title