Photoactivatable crosslinker

Patent metadata

Field	Value
Publication number	US-9487663-B2
Application number	US-201414541768-A
Country	US
Kind code	B2
Filing date	Nov 14, 2014
Priority date	Mar 30, 2010
Publication date	Nov 8, 2016
Grant date	Nov 8, 2016

Abstract

Described herein is a degradable linking agent of formula Photo 1 -LG-Photo 2 , wherein Photo 1 and Photo 2 independently represent at least one photoreactive group and LG represents a linking group comprising one or more silicon atoms or one or more phosphorous atoms. The degradable linking agent includes a covalent linkage between at least one photoreactive group and the linking group, wherein the covalent linkage between at least one photoreactive group and the linking group is interrupted by at least one heteroatom. A method for coating a support surface with the degradable linking agent, coated support surfaces and medical devices are also described.

First claim

What is claimed is:

1. A method of coating a support surface with a degradable linking agent in order to provide the support surface with one or more latent reactive groups, the method comprising:
a) providing the support surface;
b) applying to the support surface the degradable linking agent,
wherein the degradable linking agent comprises a formula selected from:

wherein Photo 1 and Photo 2 , independently, represent a photoreactive group; n is an integer between 1 and 10; and R 1 -R 4 are independently cyclic, linear or branched, saturated or unsaturated, aromatic or heteroaromatic, a photoreactive group, hydroxyl or salt thereof, or a combination thereof;

wherein Photo 1 and Photo 2 , independently, represent one or more photoreactive groups; and R 1 and R 2 are independently a photoreactive group, hydroxyl or salt thereof, or a combination thereof;

wherein Photo 1 and Photo 2 , independently, represent one or more photoreactive groups and R is hydroxyl or a salt thereof, or a combination thereof;

and

wherein Photo 1 and Photo 2 , independently, represent a photoreactive group, Y represents a linker that is null, an amine, an ether, linear or branched C 1 -C 10 alkyl, or a combination thereof; and R 1 and R 2 are independently a photoreactive group, hydroxyl or salt thereof, cyclic, linear or branched hydrocarbon, saturated or unsaturated, aromatic or heteroaromatic, or a combination thereof; and
c) illuminating the degradable linking agent upon the support surface under conditions suitable to activate a first photoreactive group to attach the degradable linking agent to the support surface, wherein a second photoreactive species remains unbound to the support surface and is able to revert to a latent reactive state.

2. A support surface bearing a coating comprising a polymer layer attached to the support surface by a degradable linking agent,
wherein the degradable linking agent comprises a formula selected from:

wherein Photo 1 and Photo 2 , independently, represent a photoreactive group; n is an integer between 1 and 10; and R 1 -R 4 are independently cyclic, linear or branched, saturated or unsaturated, aromatic or heteroaromatic, a photoreactive group, hydroxyl or salt thereof, or a combination thereof;

wherein Photo 1 and Photo 2 , independently, represent one or more photoreactive groups; and R 1 and R 2 are independently a photoreactive group, hydroxyl or salt thereof, or a combination thereof;

wherein Photo 1 and Photo 2 , independently, represent one or more photoreactive groups and R is hydroxyl or a salt thereof, or a combination thereof;

and

wherein Photo 1 and Photo 2 , independently, represent a photoreactive group, Y represents a linker that is null, an amine, an ether, linear or branched C 1 -C 10 alkyl, or a combination thereof; and R 1 and R 2 are independently a photoreactive group, hydroxyl or salt thereof, cyclic, linear or branched hydrocarbon, saturated or unsaturated, aromatic or heteroaromatic, or a combination thereof; and
wherein a first photoreactive group of the degradable linking agent, when activated in the presence of the support surface, is able to attach the degradable linking agent to the support surface, and a second photoreactive group of the degradable linking agent, when activated in the presence of a coating agent, is able to attach the coating to the support surface.

3. A coated medical device comprising: a medical device and a polymeric coating, wherein the coating is attached to the medical device by a degradable linking agent,
wherein the degradable linking agent comprises a formula selected from:

wherein Photo 1 and Photo 2 , independently, represent a photoreactive group; n is an integer between 1 and 10; and R 1 -R 4 are independently cyclic, linear or branched, saturated or unsaturated, aromatic or heteroaromatic, a photoreactive group, hydroxyl or salt thereof, or a combination thereof;

wherein Photo 1 and Photo 2 , independently, represent one or more photoreactive groups; and R 1 and R 2 are independently a photoreactive group, hydroxyl or salt thereof, or a combination thereof;

wherein Photo 1 and Photo 2 , independently, represent one or more photoreactive groups and R is hydroxyl or a salt thereof, or a combination thereof;

and

wherein Photo 1 and Photo 2 , independently, represent a photoreactive group, Y represents a linker that is null, an amine, an ether, linear or branched C 1 -C 10 alkyl, or a combination thereof; and R 1 and R 2 are independently a photoreactive group, hydroxyl or salt thereof, cyclic, linear or branched hydrocarbon, saturated or unsaturated, aromatic or heteroaromatic, or a combination thereof.

4. The method of coating a support surface of claim 1 , wherein the hydroxyl or salt thereof comprises a sodium salt, a potassium salt, a lithium salt, or a combination thereof.

5. The support surface of claim 2 , wherein the hydroxyl or salt thereof comprises a sodium salt, a potassium salt, a lithium salt, or a combination thereof.

6. The coated medical device of claim 3 , wherein the hydroxyl or salt thereof comprises a sodium salt, a potassium salt, a lithium salt, or a combination thereof.

7. The method of coating a support surface of claim 1 , wherein one or more photoreactive groups comprise an aryl ketone.

8. The support surface of claim 2 , wherein one or more photoreactive groups comprise an aryl ketone.

9. The coated medical device of claim 3 , wherein one or more photoreactive groups comprise an aryl ketone.

10. The method of coating a support surface of claim 1 , wherein one or more photoreactive groups comprise benzophenone.

11. The support surface of claim 2 , wherein one or more photoreactive groups comprise benzophenone.

12. The coated medical device of claim 3 , wherein one or more photoreactive groups comprise benzophenone.

Assignees

• Surmodics Inc

Inventors

• Kurdyumov Aleksey V
• Swan Dale G

Classifications

• A61L27/34

  Macromolecular materials · CPC title

• C08F2/48

  by ultraviolet or visible light · CPC title

• C07F9/12

  with hydroxyaryl compounds · CPC title

• A61L31/10

  Macromolecular materials · CPC title

• A61L2400/18

  Modification of implant surfaces in order to improve biocompatibility, cell growth, fixation of biomolecules, e.g. plasma treatment · CPC title