Antimicrobial AZO compounds and uses thereof
View Patent ↗Antimicrobial azo compounds include azobenzene monomers having a phenyl ring comprising a hydroxyl substituent group. The azobenzene monomers can be reacted with a polymeric material to form an antimicrobial coating that prevents growth of persistent biofilms. In some implementations, the azobenzene monomers can be used to coat the surface of a dental resin-based composite to prevent the formation secondary caries. In some implementations, the azobenzene coating can be used to disperse microbial biofilms through a photofluidization process (rapid photoisomerization) in addition to biochemically preventing formation of the microbial biofilm.
1 . A polymeric composition comprising:
a polymer chain in a dental resin-based composite; and
an azobenzene pendant group attached to the polymer chain, wherein the azobenzene pendant group includes a N═N double bond group and a phenyl ring having a hydroxyl substituent group, and wherein the azobenzene pendent group is attached via a linking group to the polymer chain at a ring carbon atom ortho to the N═N double bond group.
2 . The polymeric composition of claim 1 , wherein the azobenzene pendant group has the following structure:
wherein:
x is an integer from 1 to 10;
L is a linking group that links the structure to the polymer chain in a dental resin-based composite; and
R2, R3, R4, R5, R6, R7, R8, R9, and R10 are independently selected from H, methyl, and hydroxyl, and wherein at least one of R2, R3, R4, R5, R6, R7, R8, R9, or R10 is hydroxyl.
3 . The polymeric composition of claim 2 , wherein L is a (meth)acrylate linking group.
4 . The polymeric composition of claim 2 , wherein x is 1.
5 . The polymeric composition of claim 2 , wherein at least one of R7, R8, or R9 is hydroxyl.
6 . The polymeric composition of claim 2 , wherein x is 1; L is a (meth)acrylate linking group; and at least one of R7, R8, or R9 is hydroxyl.
7 . The polymeric composition of claim 2 , wherein x is 1; L is a (meth)acrylate linking group; and at least one of R6 is hydroxyl.
8 . The polymeric composition of claim 1 , wherein the azobenzene pendant group has the following structure:
9 . A method of making the polymeric composition of claim 1 , comprising reacting an azobenzene monomer with the polymer chain in the dental resin-based composite to form the polymeric composition comprising the azobenzene pendant group attached to the polymer chain, wherein the azobenzene monomer includes a N═N double bond group and a phenyl ring having a hydroxyl substituent group.
10 . The method of claim 9 , wherein the azobenzene pendant group has the following structure:
wherein:
x is an integer from 1 to 10;
L is a linking group that links the structure to the polymer chain in a dental resin-based composite; and
R2, R3, R4, R5, R6, R7, R8, R9, and R10 are independently selected from H, methyl, and hydroxyl, and wherein at least one of R2, R3, R4, R5, R6, R7, R8, R9, or R10 is hydroxyl.
11 . The method of claim 10 , wherein L is a (meth)acrylate linking group.
12 . The method of claim 10 , wherein x is 1.
13 . The method of claim 10 , wherein at least one of R7, R8, or R9 is hydroxyl.
14 . The method of claim 10 , wherein x is 1, L is a (meth)acrylate linking group, and at least one of R7, R8, or R9 is hydroxyl.
15 . The method of claim 10 , wherein x is 1, L is a (meth)acrylate linking group; and at least R6 is hydroxyl.
16 . The method of claim 9 , wherein the azobenzene pendant group has the following structure: