Sulfhydryl-Functionalized Polymeric Compositions For Medical Devices

Patent metadata

Field	Value
Publication number	US-2015265743-A1
Application number	US-201314438493-A
Country	US
Kind code	A1
Filing date	Oct 24, 2013
Priority date	Oct 24, 2012
Publication date	Sep 24, 2015
Grant date	—

Abstract

The present disclosure provides sulfhydryl-modified polymer foams, which may be used for wound dressing materials. For example, the modified materials can include free sulfhydryl group, which can serve as a linker to attach biologically active molecules. For example, sulfhydryl groups can be used to conjugate biologically active polypeptides and/or metals to foam polymers. Methods for using sulfhydryl-modified polymers, such as for wound dressings, are also provided.

First claim

What is claimed is:

1 . A functionalized material comprising a polymer copolymerized with one or more sulfhydryl containing molecules selected from the group consisting of D-penicillamine, glutathione, Cleland's agent, and a sulfhydryl-siloxane molecule.

2 . A functionalized material comprising a polymer copolymerized with a sulfhydryl-siloxane having formula (I):

wherein one or both of R 1 and R 2 forms a first covalent bond with the polymer and the other is OH, OCH 3 , O(CH 2 ) 1-4 CH 3 , or a covalent bond with the polymer;
n is 1-30; and,
R 3 is H.

3 . A functionalized material comprising a polymer copolymerized with a sulfhydryl-polyol or a sulfhydryl-polyethylene glycol (PEG).

4 . The material of claim 1 , 2 , or 3 , further comprising one or more covalently attached adapters.

5 . The material of claim 4 , wherein the adapter has the structure of formula (I):

wherein one or both of R 1 and R 2 forms a first covalent bond with the material and the other is OH, OCH 3 , O(CH 2 ) 1-4 CH 3 , or a covalent bond with the polymer;
n is 1-30; and,
R 3 is H.

6 . The material of any one of claims 1 to 5 , wherein the polymer comprises polyurethane, polyolefins, polyester, polyol, ethylene vinyl acetate, elastomer, poloxamer, silicone, polyvinyl alcohol, polystyrene, fluoro carbon polymer, polyester, or a combination thereof.

7 . The material of claim 6 , wherein the polymer comprises polyurethane.

8 . The material of any one of claims 1 to 7 , wherein the material comprises a polyurethane-based material, sheet, solid or semi-solid membrane, permeable or semi-permeable membrane, interfacial layer, bead coating, catheter or stent coating, or coating for other device.

9 . A functionalized polyurethane-based polymer material further comprising one or more adapters and crosslinkers, wherein the one or more adapters are covalently attached to the material and the one or more crosslinkers are covalently attached to the adapter.

10 . The material of any one of claims 1 to 9 , wherein the material further comprises a biologically active agent.

11 . The material of claim 10 , wherein the biologically active agent is covalently attached directly to the material, is covalently attached to the adapter on the material, or is covalently attached to the crosslinker, which is attached to the adapter on the material.

12 . The material of claim 9 or claim 11 , wherein the one or more crosslinkers are sulfhydryl-to-sulfhydryl, sulfhydryl-to-amine, sulfhydryl-to-carbohydrate, sulfhydryl-to-hydroxyl, sulfhydryl-to-metal, or sulfhydryl-to-carboxylate.

13 . The material of any one of claim 4 , 5 , 9 , 11 , or 12 , wherein the adapter and/or the crosslinker is cleavable.

14 . The material of any one of claims 10 to 13 , wherein the biologically active agent is a therapeutic agent selected from the group consisting of a peptide, polypeptide, peptide matrix, protein matrix, carbohydrate, oligonucleotide, antimicrobial, small molecule, nanoparticle, nanobot, aliphatic hydrocarbon chain, surfactants, alginate, aptamer, and a combination thereof.

15 . The material of claim 10 , wherein the biologically active agent is a metal cation in the +1, or +2 state, and present in either a salt or elemental form.

16 . The material of claim 15 , wherein the metal is copper, zinc, sodium, lithium, potassium, calcium, magnesium, iron, cadmium, gold, or silver.

17 . A functionalized foam comprising the material of any one of claims 1 to 3 or 6 to 8 .

18 . The foam of claim 17 , further comprising one or more covalently attached adapters.

19 . The foam of claim 18 , wherein the adapter has the structure of formula (I):

wherein one or both of R 1 and R 2 forms a first covalent bond with the foam and the other is OH, OCH 3 , O(CH 2 ) 1-4 CH 3 , or a covalent bond with the foam;
n is 1-30; and,
R 3 is H.

20 . A functionalized polyurethane-based polymer foam further comprising one or more adapters and crosslinkers, wherein the one or more adapters are covalently attached to the foam and the one or more crosslinkers are covalently attached to the adapter.

21 . The foam of any one of claims 17 to 20 , wherein the foam further comprises a biologically active agent.

22 . The foam of claim 21 , wherein the biologically active agent is covalently attached directly to the foam, is covalently attached to the adapter on the foam, or is covalently attached to the crosslinker, which is attached to the adapter on the foam.

23 . The foam of claim 20 or claim 22 , wherein the one or more crosslinkers are sulfhydryl-to-sulfhydryl, sulfhydryl-to-amine, sulfhydryl-to-carbohydrate, sulfhydryl-to-hydroxyl, sulfhydryl-to-metal, or sulfhydryl-to-carboxylate.

24 . The foam of any one of claim 18 to 20 , 22 , or 23 , wherein the adapter and/or the crosslinker is cleavable.

25 . The foam of any one of claims 21 to 24 , wherein the biologically active agent wherein the biologically active agent is a therapeutic agent selected from the group consisting of a peptide, polypeptide, peptide matrix, protein matrix, carbohydrate, oligonucleotide, antimicrobial, small molecule, nanoparticle, nanobot, aliphatic hydrocarbon chain, surfactants, alginate, aptamer, and a combination thereof.

26 . The foam of claim 21 , wherein the biologically active agent is a metal cation in the +1, or +2 state, and present in either a salt or elemental form.

27 . The foam of claim 26 , wherein the metal is copper, zinc, sodium, lithium, potassium, calcium, magnesium, iron, cadmium, gold, or silver.

28 . The foam of any one of claims 17 to 27 , wherein the foam is a reticulated open-celled foam.

29 . A method of producing a functionalized foam from the material of claim 17 , wherein the method comprises copolymerizing a polyol, a diisocyanate, and a molecule containing a sulfhydryl group to form a functionalized foam.

30 . The method of claim 29 , further comprising covalently attaching one or more adapters to the foam.

31 . The method of claim 30 , wherein the adapter has the structure according to:

wherein one or both of R 1 and R 2 forms a first covalent bond with the foam and the other is OH, OCH 3 , O(CH 2 ) 1-4 CH 3 , or a covalent bond with the foam;
n is 1-30; and,
R 3 is H.

32 . The method of any one of claims 29 to 31 , wherein the method further comprises covalently attaching a biologically active agent directly to the foam or covalently attaching a biologically active agent through an adapter on the foam.

33 . A method of producing a functionalized foam from the material of claim 20 , wherein the method comprises copolymerizing a polyol and a diisocyanate to form a functionalized foam, covalently attaching an adapter to the foam, and c

Assignees

• Kci Licensing Inc

Inventors

• Hanson Douglas Philip
• Courage James

Classifications

• C08G18/837

  by silicon containing compounds · CPC title

• A61N1/0468

  Specially adapted for promoting wound healing · CPC title

• C08J2205/06

  Flexible foams · CPC title

• A61L26/0085

  Porous materials, e.g. foams or sponges · CPC title

• A61L15/425

  Porous materials, e.g. foams or sponges · CPC title