Immobilization of dyes and antimicrobial agents on a medical device

A method of coating a surface, comprising:

• cleaning a porous surface of a medical device made from a polymer;
• treating the surface with a strong acid to provide a plurality of functional groups on the surface;
• reacting the functional groups with a linking agent to form attachment sites, the linking agent selected from the group consisting of poly(N-succinimidyl acrylate) (PNSA) and polymers with an aldehyde functional group;
• and
• attaching a solvatochromic dye, an antimicrobial agent, or an alkyl-amino containing compound selected from the group consisting of peptides, proteins, Factor VIII or other anti-clotting Factor, polysaccharides, polymyxins, hyaluronic acid, heparin, chitosan, and derivatives of each of these, to the attachment sites.

A polymeric medical device, comprising:

• a housing of the polymeric medical device;
• a porous polymer surface atop the medical device;
• a plurality of attachment sites on the porous upper polymer surface;
• optionally, a plurality of functional groups attached to the attachment sites;
• and
• at least one of:
• i. a solvatochromic dye or a derivative of the solvatochromic dye;
• and ii. an antimicrobial compound, attached to the attachment sites or to the functional groups, wherein the porous polymeric surface is configured to reversibly change from a first appearance to a second appearance when the surface is swabbed with a disinfecting solution.

A medical device, comprising:

• a medical device having a porous surface made from a polymer;
• a plurality of attachment sites on the surface of the medical device;
• optionally, a plurality of functional groups attached to the attachment sites;
• and
• an antimicrobial compound, attached to the attachment sites or to the functional groups, wherein the antimicrobial compound is configured to be cidal to, or to resist growth of, microorganisms on the surface of the device.

A medical device, comprising:

• a medical device having a porous surface made from a polymer;
• a plurality of attachment sites on the surface of the medical device;
• optionally, a plurality of functional groups attached to the attachment sites;
• and
• an alkyl-amino containing compound selected from the group consisting of peptides, proteins, Factor VIII or other anti-clotting Factor, polysaccharides, polymyxins, hyaluronic acid, heparin, condroitin sulfate, chitosan, and derivatives of each of these, to the attachment sites.

A process for making a dye, comprising:

• reacting a t-butyl-oxycarbonyl (BOC) amino aliphatic alcohol with a sulfonyl halide to yield a BOC-amino-aliphatic-sulfonate;
• reacting the BOC-amino-aliphatic-sulfonate with 4-picoline to form a pyridinium sulfonate;
• and
• reacting the pyridinium sulfonate with a substituted salicylaldehyde compound to form a compound with a merocyanine dye functionality, wherein the merocyanine dye has the general structure of
• wherein R′=t-butyl-oxycarbonyl, n=1, 2, or 3, X=bromide, chloride, fluoride, iodide, alkoxy, nitrate, and mixtures thereof and are both in meta positions, and wherein the O− is in an ortho or para position.

A process for making a dye, the process comprising:

• forming a BOC-amino-aliphatic-sulfonate from a primary alcohol and a sulfonyl halide;
• reacting the BOC-amino-aliphatic-sulfonate with 4-picoline to form a pyridium sulfonate;
• reacting the pyridinium sulfonate with a substituted salicylaldehye to form a phenolate with a monomerocyanine functionality;
• and
• dissolving the phenolate in an acid to form a first salt.