Antimicrobial guanidinium and thiouronium functionalized polymers
Antimicrobial cationic polycarbonates and polyurethanes have been prepared comprising one or more pendent guanidinium and/or isothiouronium groups. Additionally, antimicrobial particles were prepared having a silica core linked to surface groups comprising a guanidinium and/or isothiouronium group. The cationic polymers and cationic particles can be potent antimicrobial agents against Gram-negative microbes, Gram-positive microbes, and/or fungi.
1. An antimicrobial cationic polymer, comprising a cationic subunit of formula (A-1):
wherein
atoms 1-6 are backbone atoms of the cationic polymer,
m is 1 or 2,
n is 0 or 1, wherein when m is 2, n is 0,
each R′ is an independent monovalent radical selected from the group consisting of hydrogen and alkyl groups comprising 1 to 6 carbons,
R″ is a monovalent radical selected from the group consisting of hydrogen and alkyl groups comprising 1 to 6 carbons, and
each Q″ is an independent group comprising an isothiouronium group.
2. The cationic polymer of claim 1 , wherein the cationic polymer is selected from the group consisting of polycarbonates and polyurethanes.
3. The cationic polymer of claim 1 , wherein the cationic polymer is capable of killing a Gram-positive bacterium, a Gram-negative bacterium, and/or a fungus.
4. The cationic polymer of claim 1 , wherein m is 1 and n is 1.
5. The cationic polymer of claim 1 , wherein the cationic subunit has a structure according to formula (A-2):
wherein
atoms 1-6 are backbone atoms of the cationic polymer,
L′ is a divalent hydrocarbon radical comprising 2 to 30 carbons,
Q′ is *—S—*,
each R′ is an independent monovalent radical selected from the group consisting of hydrogen and alkyl groups comprising 1 to 6 carbons,
R″ is a monovalent radical selected from the group consisting of hydrogen and alkyl groups comprising 1 to 6 carbons,
X′ is a negative-charged counterion, and
Y′ is *—O—* or *—N(H)—*.
6. The cationic polymer of claim 5 , wherein L′ is selected from the group consisting of 1,2-ethylene, 1,3-propylene, 1,4-butylene, 1,5-pentylene, 1,4-cyclohexylene, and 1,4-phenylene.
7. The cationic polymer of claim 5 , wherein Y′ is *—O—*.
8. The cationic polymer of claim 5 , wherein Y′ is *—N(H)—*.
9. The cationic polymer of claim 5 , wherein R″ is methyl or ethyl.
10. The cationic polymer of claim 5 , wherein X′ is a negative-charged counterion selected from the group consisting of chloride, bromide, iodide, acetate, benzoate, trifluoroacetate, hydrogen carbonate, methansulfonate, hydrogen sulfate, and dihydrogen phosphate.
11. The cationic polymer of claim 1 , wherein the cationic polymer has a structure in accordance with formula (B-1):
Z′—P′—Z″ (B-1),
wherein
Z′ is a monovalent first end group comprising 1 to 40 carbons,
Z″ is a monovalent second end group selected from the group consisting of hydrogen and groups comprising 1 to 40 carbons, and
P′ is a polymer chain comprising the cationic subunit of formula (A-1).
12. The cationic polymer of claim 11 , wherein P′ is a polycarbonate.
13. The cationic polymer of claim 11 , wherein P′ is a polyurethane.
14. The cationic polymer of claim 1 , wherein the cationic polymer has a structure in accordance with formula (B-2):
Z b —P b —C′—P b —Z b (B-2),
wherein
each P b is an independent polymer chain comprising the cationic subunit,
C′ is a divalent linking group (core group) comprising 2 to 25 carbons, wherein C′ comprises two heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur, wherein the heteroatoms are covalently linked to respective polymer chains P b , and
each Z b is an independent monovalent end group selected from the group consisting of hydrogen and groups comprising 1 to 40 carbons.
15. A method of killing a microbe, comprising contacting the microbe with the cationic polymer of claim 1 .
16. An antimicrobial composition comprising the cationic polymer of claim 1 and at least one other chemical component bound by non-covalent interactions.
17. The antimicrobial composition of claim 16 , wherein the antimicrobial composition is an aqueous mixture.
18. The antimicrobial composition of claim 16 , wherein said at least one other component is a drug.
19. The antimicrobial composition of claim 16 , wherein said at least one other chemical component is a gene.
20. The antimicrobial composition of claim 16 , wherein said at least one other component is an amphiphilic block copolymer and the antimicrobial composition is a hydrogel in water.
21. The antimicrobial composition of claim 16 , wherein the antimicrobial composition is a nanoparticle in water.
22. The antimicrobial composition of claim 21 , wherein the nanoparticle has an average circular cross sectional diameter between 10 nm and 500 nm.
23. The antimicrobial composition of claim 16 , wherein the antimicrobial composition is selected from the group consisting of soaps, shampoos, skin lotions, skin creams, cosmetics, mouthwashes, wound care agents, deodorants, surface cleaning agents, and laundry detergents.