# US 10,500,317 B2 · Antibacterial coatings that inhibit biofilm formation on implants > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,500,317 B2 - Document ID: US10500317B2 - Status: Granted - Kind: B2 - Application number: 15/815,522 - Filed: 2017-11-16 - Published: 2018-03-22 - Granted: 2019-12-10 - Earliest claimed: 2011-10-06 - Assignees: Massachusetts Institute of Technology; The Trustees of the University of Pennsylvania - Applicants: Massachusetts Institute of Technology - Inventors: Thomas P. Schaer; Suzanne Stewart; Alexander M. Klibanov - Web page: https://patentgrep.com/patent/US10500317B2 ## CPC - A61L 31/16: Biologically active materials, e.g. therapeutic substances {(A61L31/047 takes precedence)} - A01N 33/12: Quaternary ammonium compounds - A61F 2/02: Prostheses implantable into the body - A61F 2/14: Eye parts, e.g. lenses or corneal implants; Artificial eyes - A61L 27/34: Macromolecular materials - A61L 27/50: Materials characterised by their function or physical properties {, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials} - A61L 27/54: Biologically active materials, e.g. therapeutic substances {(A61L27/227 takes precedence)} - A61L 29/085: {Macromolecular materials} - A61L 29/16: Biologically active materials, e.g. therapeutic substances {(A61L29/048 takes precedence)} - A61L 31/10: Macromolecular materials - A61L 2300/404: Biocides, antimicrobial agents, antiseptic agents - A61L 2300/606: Coatings - A61L 2420/02: Methods for coating medical devices - A61L 2430/14: for ear reconstruction or ear implants, e.g. implantable hearing aids - A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K) - A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS - A61F: FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS (dental prosthetics A61C) ## Abstract Orthopedic and dental implants coated with an antibacterial coating and methods of making and using, are described herein. The implant can be coated with a hydrophobic, polycationic antibacterial polymer. The polymer can be covalently or non-covalently associated with the surface; however, in particular embodiments, the polymer is non-covalently associated with the surface. As shown in the examples below, clinical observations, digital radiography, and a battery of well-accepted ex vivo analytical methods show that the presence of a hydrophobic polycationic polymer coating, such as N,N-dodecyl,methyl-PEI coating on the surface of a metal implant, was effective in eliminating the clinical signs of infection in vivo in a large animal infection model. Moreover, the coated plates supported bone healing, and in fact decreased healing times, even in the presence of significant bacterial contamination compared to a control. ## Claims ### Claim 1 An ophthalmic implant comprising a coating on one or more surfaces of the implant, wherein the coating comprises an antimicrobial hydrophobic polycationic polymer selected from the group consisting of poly (4-vinyl-N-alkylpyridine), N,N-dialkylated branched polyethylene imine, and N,N-dialkylated linear polyethylene imine polymers. ### Claim 2 (depends on 1) The implant of claim 1, wherein the implant comprises synthetic or natural, cross-linked or non-crosslinked, polymeric materials. ### Claim 3 (depends on 2) The implant of claim 2, wherein the implant comprises a non-degradable polymeric material. ### Claim 4 (depends on 3) The implant of claim 3, wherein the polymeric material is selected from the group consisting of polypropylene (PP), polyethylene (PE), polyacetylene, cross-linked or non-crosslinked polystyrene, poly(vinyl chloride) (PVC), polyolefin copolymers, poly(methyl methacrylate), polyphenylene, polyacrylonitrile, and blends or copolymers thereof. ### Claim 5 (depends on 2) The implant of claim 2, wherein the implant comprises a biodegradable polymeric material. ### Claim 6 (depends on 5) The implant of claim 5, wherein the implant comprises a polymeric material selected from the group consisting of collagen, cellulosic polymers, polysaccharides, poly(glycolic acid), poly(L-lactic acid) (PLLA), poly(lactide-co-glycolide) (PLGA), a polydioxanone (PDA), or racemic poly(lactic acid), polyurethane (PU), polycarbonates, polyetherketone (PEEK), polyesters, and polyamides. ### Claim 7 (depends on 1) The implant of claim 1, wherein the implant is a prosthesis. ### Claim 8 (depends on 1) The implant claim 1 wherein said hydrophobic polycation is a N-alkylated branched or linear polyethylenimine (PEI). ### Claim 9 (depends on 1) The implant of claim 1 wherein the N,N-dialkylated branched polyethylene imine or N,N-dialkylated linear polyethylene imine is N,N-dodecyl,methyl-PEI or N,N-hexyl,methyl-PEI. ### Claim 10 (depends on 1) The implant of claim 1, wherein the weight average molecular weight of the N,N-dialkylated branched polyethylene imine or N,N-dialkylated linear polyethylene imine polymer is at least 20,000 g/mol. ### Claim 11 (depends on 1) The implant of claim 1, wherein the thickness of the polymer coating is between about 1 nm and about 1 cm. ### Claim 12 (depends on 1) The implant of claim 1, wherein the polymer coating is non-covalently associated with one or more outer surfaces of the implant. ### Claim 13 (depends on 1) The implant of claim 1, wherein the polymer coating is covalently associated with one or more outer surfaces of the implant. ### Claim 14 (depends on 1) A method of preventing infection comprising implanting the implant of claim 1. ### Claim 15 (depends on 14) The method of claim 14, wherein the coating is applied to the implant immediately prior to implantation. ### Claim 16 (depends on 1) A method of treating tissue in the presence of an infection, the method comprising implanting the implant of claim 1. ### Claim 17 (depends on 16) The method of claim 16, wherein the coating is applied to the implant immediately prior to implantation. ### Claim 18 (depends on 1) The implant of claim 1 wherein the poly (4-vinyl-N-alkylpyridine) has the formula: wherein, R for each occurrence is independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, acyl, aryl, carboxylate, alkoxycarbonyl, aryloxycarbonyl, carboxamido, alkylamino, acylamino, alkoxyl, acyloxy, hydroxyalkyl, alkoxyalkyl, aminoalkyl, (alkylamino)alkyl, thio, alkylthio, thioalkyl, (alkylthio)alkyl, carbamoyl, urea, thiourea, sulfonyl, sulfonate, sulfonamido, sulfonylamino, and sulfonyloxy; R′ is selected from the group consisting of an alkyl, an alkylidene tethered to the surface, and an acyl tethered to the surface; Z− is independently selected from the group consisting of Cl, Br, or I; and n is an integer less than or equal to about 1500. ### Claim 19 (depends on 18) The implant of claim 18, wherein R′ is selected from the group consisting of a C4-C12 alkyl, C6-C12 alkyl, and C6-C10 alkyl. ### Claim 20 (depends on 1) The implant of claim 1, wherein the weight average molecular weight of weight of the poly(4-vinyl-N-alkylpyridine) polymer is at least 50,000 g/mol.