High-yield activation of polymer surfaces for covalent attachment of molecules

Abstract

Polymer surfaces coated with organometallic layers, wherein the organometallic layers and polymer surfaces have functional groups that react to bond the organometallic layer to the polymer surface with organometallic functional groups remaining unreacted for the subsequent covalent attachment of organic overlayers. Coating methods and coated articles are also disclosed.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS [0001] The present application claims priority benefit under 35 U.S.C. §119(e) of U.S. Provisional Patent Application Nos. 60 / 775,127 filed Feb. 21, 2006 and 60 / 804,633 filed Jun. 13, 2006. The disclosures of both applications are incorporated herein by reference.BACKGROUND OF THE INVENTION [0002] The present invention relates to covalently binding organic materials to the surfaces of polymer substrates by functionalizing the surfaces with linker moieties containing transition metal complexes. In particular, the present invention relates to modifying polymer surfaces with organometallic compounds that have functional groups that react with functional groups of the polymer surface. The modified polymer surface can be further reacted with a compound, polymer or oligomer that contains functional groups that are reactive with functional groups of the organometallic compound that remain after reaction with the polymer surface. The present invention...

AI Technical Summary

Benefits of technology

[0008] In one embodiment, the present invention provides a novel approach to polymer surface modification that enables high surface density derivatization of polymers with reactive surface moieties containing acidic covalent bonds. The polymers need not contain pendant functional groups with acidic covalent bonds. For example, polymers with exposed amide functionality contain acidic N—H bonds, which can serve as sites for chemical derivatization when appropriately activated. In particular, coordination of the carbonyl group to an appropriate metallic center further acidifies the N—H bonds and facilitates derivatization. In addition, acidic C—H bonds on polymer surfaces can also serve as sites for chemical derivatization when appropriately activated. In particular, coordination of the carbonyl group to an appropriate metallic center further acidifies the C—H bonds and facilitates derivatization.

[0012] The present invention thus provides a novel type of interface that enables strong adhesion between a polymer surface and an organic coating. The coating modifies the surface of the polymer making it more hydrophilic or hydrophobic as may be desired. The modification can make the polymer surface more or less receptive to subsequently applied coatings, improving or minimizing the adhesion of the polymer to the subsequently applied coating. The polymer surface can be a polymer coating on an article made from another material, such as glass, silicon dioxide, metal, or another polymer. The polymer surface can also be the surface of a pre-cast polymer article. Examples of suitable polymers with reactive functional groups include polyamides, such as nylon, silk, and collagen, polyacrylamides, polyimides, polyurethanes, polyureas, polysulfonamides, polyesters, polysaccharides, such as haluronic acid, methylcellulose and proteoglycans, and the like, and copolymers of any of these polymers.

[0013] According to one embodiment of this aspect of the invention, the polymer is a biocompatible polymer and the polymer-coated or polymer-cast article is a medical implant or biological scaffold or porous matrix. The organic ligand can then be a protein, peptide, peptide mimetic, small molecule ligand for a cell surface receptor, or other biologically or pharmaceutically active compound having utility as a coating on a medical implant. The organic ligand can thus promote or prevent cell growth or proliferation, promote or discourage cell adhesion, prevent infection, or prevent or promote blood clotting or adhesion.

[0019] The method of the present invention thus provides high yield coatings on polymer surfaces with the adhesion properties of physical deposition methods under mild reaction conditions. In particular, the coatings of the present invention may be formed at ambient temperatures.

Problems solved by technology

Adjustment of the surface properties of polymers such as those from which preformed polymeric therapeutic devices are formed, has proven problematic because those polymers most often used as biomaterials are resistant to specific surface treatments.

To circumvent this problem, polymer scaffold materials have been prepared by blending, copolymerization, or physical treatment, but these methods can result in alteration of the bulk properties of the polymer.

Furthermore, these methods or attempts to surface modify pre-cast polymers using standard methods of organic synthesis, result only in low surface coverage by peptides that do not approach those that can be achieved on metallic substrates.

Surface modification has also proven problematic in other areas of polymer and polymer surface customization.

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