Methods and systems for coating a medical device
An antimicrobial coating system and method are described. In some embodiments, a system may include a composition. The composition may include one or more bridged polycyclic compounds. At least one of the bridged polycyclic compounds may include at least two cyclic groups, and at least two of the cyclic groups may include quaternary ammonium moieties. In some embodiments, a method may include applying an antimicrobial coating to an oral surface, a surface of a construction substrate, a surface of a marine substrate, a surface of a medical device, or a surface of a personal care device. The protective coating may be antimicrobial. A protective coating may include antimicrobial bridged polycyclic compounds. Bridged polycyclic compounds may include quaternary ammonium compounds. Bridged polycyclic compounds based coating systems may impart self-cleaning properties to a surface (e.g., a tooth surface).
1. A medical device coated with a coating, the coating comprising:
a chemical composition, wherein at least a portion of the chemical composition forms an antimicrobial coating over at least a portion of a surface of a medical device, wherein the chemical composition comprises at least one bridged polycyclic compounds, wherein at least one of the bridged polycyclic compounds comprises a structure:
wherein each R 1 is independently N, N + H, or N + R 3 ;
wherein each R 2 is independently an alkyl group, a substituted alkyl group, or an alkene;
wherein each R 3 is independently an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, a heterocycle group, a substituted heterocycle group, an alkene, a benzyl group, a hydrogen, or a hydrophilic group;
wherein each R 4 is independently an aryl group or a substituted aryl group, wherein when R 4 is an aryl group the aryl group is a phenyl, a naphthyl, a biphenyl, a diphenylmethyl, or a benzophenone, wherein when R 4 is a substituted aryl group the substituted aryl group is a phenyl having at least one substituent, a naphthyl having at least one substituent, a biphenyl having at least one substituent, a diphenylmethyl having at least one substituent, or a benzophenone having at least one substituent, wherein when R 4 is an aryl group at least two moieties forming the aryl group of R 4 are independently coupled to the adjacent nitrogen of the —NR 3 —R 2 — moiety or the —N + R 3 2 —R 2 — moiety of the respective structure of the bridged polycyclic compound, or when R 4 is a substituted aryl group the substituted aryl group has at least one substituent and at least two moieties forming one or more of the aryl groups of the substituted aryl group are independently coupled to the adjacent nitrogen of the —NR 3 —R 2 — moiety or the —N + R 3 2 —R 2 — moiety;
wherein Z comprises at least one bridge, wherein at least one of the bridges is —R 2 —N + R 3 2 —R 4 —N + R 3 2 —R 2 —,—R 2 —NR 3 —R 4 —N + R 3 2—R 2 —,—R 2 —NR 3 —R 4 —NR 3 —R 2 —, or R 2 —N ═R 4 ═N—R 2 —, and wherein each bridge independently couples R 1 to R 1 ; and
wherein X comprises at least one negatively charged counter ion.
2. The medical device of claim 1 , wherein the medical device comprises at least a portion of a catheter.
3. The medical device of claim 1 , wherein the medical device comprises at least a portion of a contact lens.
4. The medical device of claim 1 , wherein the medical device comprises at least a portion of a feeding tube.
5. The medical device of claim 1 , wherein the medical device comprises at least a portion of a dental device or at least a portion of a dental fixture.
6. A chemical composition comprising at least one bridged polycyclic compound, wherein the bridged polycyclic compound comprises a structure:
wherein each R 1 is independently N, N + R 3 , or N + H;
wherein each R 2 is independently an alkyl group, a substituted alkyl group, or an alkene;
wherein each R 3 is independently an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, a heterocycle group, a substituted heterocycle group, an alkene, a benzyl group, or a hydrophilic group, and wherein at least one R 3 comprises an acyclic guanidinium covalently bound directly to the N of the —NR 3 —R 2 — moiety or the —N + R 3 2—R 2 — moiety;
wherein each R 4 is independently an aryl group or a substituted aryl group, wherein when R 4 is an aryl group the aryl group is a phenyl, a naphthyl, a biphenyl, a diphenylmethyl, or a benzophenone, wherein when R 4 is a substituted aryl group the substituted aryl group is a phenyl having at least one substituent, a naphthyl having at least one substituent, a biphenyl having at least one substituent, a diphenylmethyl having at least one substituent, or a benzophenone having at least one substituent, wherein when R 4 is an aryl group at least two moieties forming the aryl group of R 4 are independently coupled to the adjacent nitrogen of the —NR 3 —R 2 — moiety or the —N + R 3 2 —R 2 — moiety of the respective structure of the bridged polycyclic compound, or when R 4 is a substituted aryl group the substituted aryl group has at least one substituent and at least two moieties forming one or more of the aryl groups of the substituted aryl group are independently coupled to the adjacent nitrogen of the —NR 3 —R 2 — moiety or the —N + R 3 2 —R 2 — moiety;
wherein Z comprises at least one bridge, wherein at least one of the bridges is —R 2 —N + R 3 2 —R 4 —N + R 3 2 —R 2 —,—R 2 —NR 3 —R 4 —N + R 3 2 —R 2 —,—R 2 —NR 3 —R 4 —NR 3 —R 2 —, or R 2 N═R 4 ═N—R 2 —, and wherein each bridge independently couples R 1 to R 1 ; and
wherein X comprises at least one negatively charged counter ion.
7. The chemical composition of claim 6 , wherein at least one of the bridged polycyclic compounds comprises at least four quaternary ammonium moieties.
8. The chemical composition of claim 6 , wherein at least one of the bridged polycyclic compounds has a structure (I):
9. The chemical composition of claim 6 , wherein at least one of the bridged polycyclic compounds has a minimum inhibitory concentration of less than 0.1 mg/mL.
10. The chemical composition of claim 6 , wherein at least one X comprises one or more elements with antimicrobial activity or antiinflammatory activity.
11. The chemical composition of claim 6 , wherein the composition further comprises a metal oxide coated bridged polycyclic compound.
12. The chemical composition of claim 6 , wherein at least one R 3 comprises an amide moiety.
13. The chemical composition of claim 6 , wherein at least one of the bridged polycyclic compounds has a structure:
14. The chemical composition of claim 6 , wherein R 4 is a substituted aryl group.
15. The chemical composition of claim 6 , wherein at least one R 3 is a substituted aryl group.
16. The chemical composition of claim 6 , wherein at least one R 3 comprises a substituted aryl group, wherein at least one of the substituted aryl group's substituents comprises a guanidinium group.
17. The chemical composition of claim 6 , wherein each R 3 is independently an alkyl-aryl group, a substituted alkyl-aryl group, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, a heterocycle group, a substituted heterocycle group, an alkene, or a hydrophilic group, and wherein at least one alkyl group comprises a C5-C7 alkyl group.
18. The chemical composition of claim 6 , wherein at least one R 3 is a hydrophilic group.
19. The medical device of claim 1 , wherein when R 4 is a phenyl having at least one substituent the phenyl having at least one substituent is
20. The chemical composition of claim 6 , wherein when R 4 is a phenyl having at least one substituent the phenyl having at least one substituent is
21. The medical device of claim 1 , wherein when R 3 is a hydrophilic group the hydrophilic group is an ether, a polyethylene glycol, or a polyethyleneimine group.
22. The chemical composition of claim 6 , wherein when R 3 is a hydrophilic group the hydrophilic group is an ether, a polyethylene glycol, or a polyethyleneimine group.