Antimicrobial coatings and methods of making and using thereof
Disclosed are antimicrobial articles and surfaces, as well as methods of making such articles and surfaces.
1. A process for rendering a polyvinyl chloride surface antimicrobial, the process comprising:
(a) flowing an aqueous solution comprising an azidation reagent and a phase transfer catalyst across the polyvinyl chloride surface to form an azide-substituted polyvinyl chloride; and
(b) contacting the azide-substituted polyvinyl chloride with an antimicrobial agent comprising an alkyne moiety under conditions effective to covalently bond the antimicrobial agent to the polyvinyl chloride surface.
2. The process of claim 1 , wherein step (a) comprises contacting the polyvinyl chloride with the azidation reagent and the phase transfer catalyst for 3 hours or less.
3. The process of claim 1 , wherein the alkyne moiety is activated by ring strain, electron withdrawing groups, or a combination thereof.
4. The process of claim 1 , wherein step (b) comprises contacting the azide-substituted polyvinyl chloride with the antimicrobial agent comprising the alkyne moiety in the presence of a Cu(I) catalyst.
5. The process of claim 1 , wherein the polyvinyl chloride surface comprises a surface of a medical article.
6. The process of claim 5 , wherein the medical article comprises tubing, and wherein the surface of the medical article comprises an interior surface of the tubing, an exterior surface of the tubing, or both an interior surface of the tubing and an exterior surface of the tubing.
7. The process of claim 1 , wherein the antimicrobial agent comprises a polycationic polymer.
8. The process of claim 7 , wherein the polycationic polymer comprises a polymer defined by Formula I below
wherein
Z represents, individually for each occurrence, S, Se, or NR 3 ;
A represents, individually for each occurrence, a heterocyclic ring comprising a cationic nitrogen center;
X represents, individually for each occurrence, an anion;
Y is absent, or represents, individually for each occurrence, a linking group;
R 1 is absent, or represents, individually for each occurrence, halogen, hydroxy, amino, cyano, azido, hydrazone, alkyl, alkenyl, alkynyl, alkoxy, aryl, heteroaryl, alkylaryl, alkylheteroaryl, cycloalkyl alkylcycloalkyl, heterocycloalkyl, alkylheterocycloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, peptidyl, polyamino, or polyalkyleneoxy;
R 2 is absent, or represents, individually for each occurrence, alkyl, alkenyl, alkynyl, alkoxy, aryl, heteroaryl, alkylaryl, alkylheteroaryl, cycloalkyl alkylcycloalkyl, heterocycloalkyl, alkylheterocycloalkyl, peptidyl, polyamino, or polyalkyleneoxy;
R 3 represents, individually for each occurrence, alkyl, alkenyl, alkynyl, alkoxy, aryl, heteroaryl, alkylaryl, alkylheteroaryl, cycloalkyl alkylcycloalkyl, heterocycloalkyl, alkylheterocycloalkyl, peptidyl, polyamino, or polyalkyleneoxy; and
n is an integer from 2 to 400,
wherein at least one of R 1 , R 2 , or R 3 comprises an alkynyl group.
9. The process of claim 8 , A is chosen from pyridine, imidazole, pyrazole, triazole, tetrazole, oxazole, isoxazole, furazan, isothioazole, and thiazole.
10. The process of claim 8 , wherein Z is S.
11. The process of claim 8 , wherein Z is NR 3 .
12. The process of claim 8 , wherein R 1 , R 2 , R 3 , or a combination thereof comprise a cationic moiety.
13. The process of claim 8 , wherein R 1 comprise an alkynyl group.
14. The process of claim 8 , wherein R 2 comprises an alkynyl group.
15. The process of claim 8 , wherein Y is chosen from one of the following:
where m is an integer from 1 to 12.
16. The process of claim 8 , wherein the polycationic polymer comprises a polymer defined by Formula IA below
wherein Z, X, Y, R 1 , R 2 , R 3 , and n are as defined above with respect to Formula I.
17. The process of claim 7 , wherein the polycationic polymer comprises a recurring unit defined by Formula V below
wherein
R 4 represents H or methyl;
L is absent or represents a linking group;
A represents, individually for each occurrence, a heterocyclic ring comprising a cationic nitrogen center;
R 5 is absent, or represents, individually for each occurrence, halogen, hydroxy, amino, cyano, azido, hydrazone, alkyl, alkenyl, alkynyl, alkoxy, aryl, heteroaryl, alkylaryl, alkylheteroaryl, cycloalkyl alkylcycloalkyl, heterocycloalkyl, alkylheterocycloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, peptidyl, polyamino, or polyalkyleneoxy; and
m is an integer from 0 to 5.
18. A process for rendering a polyvinyl chloride surface antimicrobial, the process comprising:
(a) contacting the polyvinyl chloride with an azidation reagent in the presence of a phase transfer catalyst to form an azide-substituted polyvinyl chloride; and
(b) contacting the azide-substituted polyvinyl chloride with an antimicrobial agent comprising an alkyne moiety under conditions effective to covalently bond the antimicrobial agent to the polyvinyl chloride surface;
wherein the wherein the antimicrobial agent comprises a polycationic polymer defined by Formula I below
wherein
Z represents, individually for each occurrence, S, Se, or NR 3 ;
A represents, individually for each occurrence, a heterocyclic ring comprising a cationic nitrogen center;
X represents, individually for each occurrence, an anion;
Y is absent, or represents, individually for each occurrence, a linking group;
R 1 is absent, or represents, individually for each occurrence, halogen, hydroxy, amino, cyano, azido, hydrazone, alkyl, alkenyl, alkynyl, alkoxy, aryl, heteroaryl, alkylaryl, alkylheteroaryl, cycloalkyl alkylcycloalkyl, heterocycloalkyl, alkylheterocycloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, peptidyl, polyamino, or polyalkyleneoxy;
R 2 is absent, or represents, individually for each occurrence, alkyl, alkenyl, alkynyl, alkoxy, aryl, heteroaryl, alkylaryl, alkylheteroaryl, cycloalkyl alkylcycloalkyl, heterocycloalkyl, alkylheterocycloalkyl, peptidyl, polyamino, or polyalkyleneoxy;
R 3 represents, individually for each occurrence, alkyl, alkenyl, alkynyl, alkoxy, aryl, heteroaryl, alkylaryl, alkylheteroaryl, cycloalkyl alkylcycloalkyl, heterocycloalkyl, alkylheterocycloalkyl, peptidyl, polyamino, or polyalkyleneoxy; and
n is an integer from 2 to 400,
wherein at least one of R 1 , R 2 , or R 3 comprises an alkynyl group.