Antimicrobial polymeric surfaces

• US 7,151,139 B2
• Filed: 04/16/2002
• Issued: 12/19/2006
• Est. Priority Date: 04/23/2001
• Status: Expired due to Fees

• Current Assignee: Massachusetts Institute of Technology, Trustees of Tufts College
• Original Assignee: Massachusetts Institute of Technology, Trustees of Tufts College
• Inventors: Tiller, Joerg C., Liao, Chun-Jen, Lewis, Kim, Klibanov, Alexander M.
• Primary Examiner(s): Mulcahy, Peter D.
• Application Number:
  US10/123,860
• Publication Number:
  US 20030091641A1
• Time in Patent Office: 1,708 Days
• Field of Search: 427/2.11, 427/2.12, 427/2.24, 427/2.25, 427/2.28, 428/448, 525/165, 525/182, 525/186, 525/203, 525/421, 525/445
• US Class Current: 525/165
• CPC Class Codes: A01N 2300/00 Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
• CPC Class Codes: A01N 25/10 Macromolecular compounds
• CPC Class Codes: A01N 25/34 Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: A61L 27/50 Materials characterised by their function or physical properties , e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
• CPC Class Codes: C08L 33/14 of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen

Abstract

Bactericidal compositions are disclosed that comprise a polymeric compound immobilized on a material. Medical devices are also disclosed which comprise such a bactericidal composition. Methods are disclosed for covalently derivatizing the surfaces of common materials with an antibacterial polycation, e.g., poly(vinyl-N-pyridinium bromide); the first step of the methods involves coating the surface with a nanolayer of silica. Various commercial synthetic polymers derivatized in this manner are bactericidal, i.e., they kill on contact up to 99% of deposited Gram-positive and Gram-negative bacteria, whether deposited through air or water.

Claims

1. A composition comprising a material and a compound immobilized to the surface of the material by a covalent bond, wherein the surface comprises silicon oxide and the immobilized compound is a water-soluble lipophilic polycation polymer comprising poly(N-alkylvinylpyridinium halide).

2. A composition comprising a surface and a compound covalently bonded to the surface, wherein the surface comprises silicon oxide and the compound is represented by formula I:

3. The composition of claim 2 wherein the tether is represented by Formula 1a:

4. The composition of claim 3 wherein the tether is a —

C₄H₈—

group.

5. The composition of claim 2, wherein the compound covalently bonded to the surface has a weight average molecule weight of at least 60,000 g/mol.

6. The composition of claim 2, wherein the compound covalently bonded to the surface has a weight average molecule weight in the range of 150,000 g/mol.

7. The composition of claim 2, wherein the compound covalently bonded to the surface is poly(4-vinyl-N-alkylpyridinium bromide).

8. The composition of claim 6, wherein the compound covalently bonded to the surface is poly(4-vinyl-N-hexylpyridinium bromide).

9. The composition of claim 2 wherein the surface further comprises low density polyethylene (LDPE), high density polyethylene (HDPE), polypropylene (PP), or poly(ethylene terephthalate) (PET).

10. The composition of claim 2, wherein the surface is the surface of a medical device.

11. The composition of claim 10, wherein the medical device is selected from the group consisting of pins, screws, plates, ventriculoatrial shunts, ventriculoperitoneal shunts, dialysis shunts, heart valves, pacemakers, infusion pumps, vascular grafting prostheses, stents, sutures, surgical meshes, replacement prostheses, breast implants, tissue expanders, contact lenses, stoma appliances, artificial larynx, endotracheal tubes, tracheal tubes, gastrostomy tubes, biliary drainage tubes, biliary steals, catheters, bandages, adhesive tapes, and clear plastic adherent sheets.

12. A composition comprising a surface and a compound covalently bonded to the surface, wherein the surface comprises silicon oxide and the compound is represented by formula I:

13. The composition of claim 12, wherein R′

is alkyl.

14. The composition of claim 12, wherein the compound covalently bonded to the surface has a weight average molecule weight of at least 60,000 g/mol.

15. The composition of claim 12, wherein the compound covalently bonded to the surface has a weight average molecule weight in the range of 150,000 g/mol.

16. The composition of claim 12, wherein the compound covalently bonded to the surface is poly(4-vinyl-N-alkylpyridinium bromide).

17. The composition of claim 12, wherein the compound covalently bonded to the surface is poly(4-vinyl-N-hexylpyridinium bromide).

18. The composition of claim 12 wherein the surface further comprises low density polyethylene (LDPE), high density polyethylene (HDPB), polypropylene (PP), or poly(ethylene terephthalate) (PET).

19. The composition of claim 12, wherein the surface is the surface of a medical device.

20. The composition of claim 19, wherein the medical device is selected from the group consisting of pins, screws, plates, ventriculoatrial shunts, ventriculoperitoneal shunts, dialysis shunts, heart valves, pacemakers, infusion pumps, vascular grafting prostheses, stents, sutures, surgical meshes, replacement prostheses, breast implants, tissue expanders, contact lenses, stoma appliances, artificial larynx, endotracheal tubes, tracheal tubes, gastrostomy tubes, biliary drainage tubes, biliary stents, catheters, bandages, adhesive tapes, and clear plastic adherent sheets.