# US 9,750,250 B2 · Conjugated polyelectrolytes and methods of using the same

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- Number: US 9,750,250 B2
- Document ID: US9750250B2
- Status: Granted
- Kind: B2
- Application number: 15/018,179
- Filed: 2016-02-08
- Published: 2016-08-04
- Granted: 2017-09-05
- Earliest claimed: 2015-01-14
- Assignees: Stc.Unm; University of Florida Research Foundation, Inc.
- Applicants: David G. Whitten; Harry Craig Pappas; Eric H. Hill; Kirk S. Schanze; Anand Parthasarathy; Yun Huang; Thomas S. Corbitt
- Inventors: David G. Whitten; Harry Craig Pappas; Eric H. Hill; Kirk S. Schanze; Anand Parthasarathy; Yun Huang; Thomas S. Corbitt
- Web page: https://patentgrep.com/patent/US9750250B2

## CPC

- A01N 43/50: 1,3-Diazoles; Hydrogenated 1,3-diazoles
- A01N 33/08: containing oxygen or sulfur
- A01N 33/12: Quaternary ammonium compounds
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A61L 15/24: Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof {(A61L15/225 takes precedence)}
- A61L 15/46: Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
- C07D 233/64: with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- C07D 409/06: linked by a carbon chain containing only aliphatic carbon atoms
- A61L 2300/404: Biocides, antimicrobial agents, antiseptic agents
- A61L 2420/02: Methods for coating medical devices
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Various embodiments disclosed relate to conjugated polyelectrolytes and methods of using the same. Various embodiments provide a conjugated polyelectrolyte including a subunit having the structure —R1—Y—R2—Z—. At each occurrence, R1 is independently chosen from 1,4-bonded phenylene substituted by —X—R3—R4 j times and 2,5-bonded thiophene substituted by —X—R3—R4 j times. At each occurrence, Y is independently chosen from a bond and —C≡C—. At each occurrence, R2 is independently chosen from a bond, a substituted or unsubstituted phenylene, thiophenylene, azulenylene, heptalenylene, biphenylene, indacenylene, fluorenylene, phenanthrenylene, triphenylenylene, pyrenylene, naphthacenylene, chrysenylene, biphenylenylene, anthracenylene, and naphthylene. At each occurrence, Z is independently chosen from a bond and —C≡C—. The variables j, R3, and R4 are as defined herein.

## Claims

### Claim 1

An antimicrobial substrate, the antimicrobial substrate comprising:
a substrate; and
a conjugated polyelectrolyte comprising a subunit having the following structure:
wherein
at each occurrence, R1has the structure:
at each occurrence, X is a bond, —O—, —NH—, or —S—,
at each occurrence, R3 is a (C1-C20)hydrocarbylene interrupted by 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9 heteroatoms,
at each occurrence, R5 is independently chosen from a substituted or unsubstituted (C1-C10)hydrocarbyl,
at each occurrence, Y is independently chosen from a bond and —C≡C—,
at each occurrence, R2 is independently chosen from a bond, a substituted or unsubstituted phenylene, thiophenylene, azulenylene, heptalenylene, biphenylene, indacenylene, fluorenylene, phenanthrenylene, triphenylenylene, pyrenylene, naphthacenylene, chrysenylene, biphenylenylene, anthracenylene, and naphthylene, and
at each occurrence, Z is independently chosen from a bond and —C≡C—.

### Claim 2 (depends on 1)

The antimicrobial substrate of claim 1, wherein in the substrate is chosen from a wipe, a tissue, a bandage, a medical device, surgical instrument, warfighter machinery, a sponge, a textile, a diaper, a counter-top, a food preparation surface, a wound dressing, a dressing for surgical incisions, a keyboard surface, a packing for wounds, a packing for surgical incisions, a nasal packing, and a feminine care product.

### Claim 3 (depends on 1)

The antimicrobial substrate of claim 1, wherein the conjugated polyelectrolyte comprises terminal groups independently chosen from —H, -L-H, -L-C≡CH, -L-C≡CH, -L-RT, -L-RL—RT, -L-C≡C—RT, -L-C≡C—RL—RT, and -L-RL—C≡C—RL—RT, -L-C≡C—RL—C≡C—RL—RT, wherein
at each occurrence, RT is independently chosen from —H, —Br, —(C1-C10)alkyl, —C(O)—OH, —C(O)—O((C1-C10)alkyl), —(C1-C10)alkylene-N((C1-C10)alkyl)3+X−, —O—(C1-C10)alkylene-N((C1-C10)alkyl)3+X−, wherein X− is a counterion,
at each occurrence, RL is independently chosen from a substituted or unsubstituted phenylene, thiophenylene, azulenylene, heptalenylene, biphenylene, indacenylene, fluorenylene, phenanthrenylene, triphenylenylene, pyrenylene, naphthacenylene, chrysenylene, biphenylenylene, anthracenylene, naphthylene, and -(1,4-substituted 1,4-diazabicyclo[2.2.2]octane-1,4-diium)-, and
at each occurrence, L is independently chosen from a bond, —(C1-C10)alkylene-, and —O—(C1-C10)alkylene-.

### Claim 4 (depends on 1)

The antimicrobial substrate of claim 1, wherein
at each occurrence, X is —O—,
at each occurrence, R3 is a (C2-C4)akylene,
at each occurrence, Y is —C≡C—,
at each occurrence, R2 is a bond, and
at each occurrence, Z is a bond.

### Claim 5 (depends on 1)

The antimicrobial substrate of claim 1, wherein
at each occurrence, X is —O—,
at each occurrence, R3 is a (C1-C10)alkylene interrupted by 0, 1, 2, 3, or 4 oxygen atoms,
at each occurrence, R5 is independently chosen from a (C1-C5)alkyl,
at each occurrence, Y is —C≡C—,
at each occurrence, R2 is a bond, and
at each occurrence, Z is a bond.

### Claim 6 (depends on 1)

The antimicrobial substrate of claim 1, wherein
at each occurrence, X is —O—,
at each occurrence, R3 is a (C2-C4)alkylene,
at each occurrence, Y is —C≡C—,
at each occurrence, R2 is independently chosen from a 1,4-substituted phenylene and a 2,5-substituted thiophenylene, and
at each occurrence, Z is a —C≡C—.

### Claim 7 (depends on 1)

The antimicrobial substrate of claim 1, wherein
at each occurrence, X is —O—,
at each occurrence, R3 is a (C1-C10)alkylene interrupted 0, 1, 3, or 4 oxygen atoms,
at each occurrence, R5 is independently (C1-C5)alkyl,
at each occurrence, Y is —C≡C—,
at each occurrence, R2 is a phenylene, and
at each occurrence, Z is a —C≡C—.

### Claim 8 (depends on 1)

The antimicrobial substrate of claim 1, wherein the conjugated polyelectrolyte is non-leachably bound to the substrate.

### Claim 9 (depends on 1)

The antimicrobial substrate of claim 1, wherein the antimicrobial substrate exhibits antimicrobial properties comprising prevention of growth of at least one of Gram-positive Staphylococcus aureus, Gram-negative Pseudomonas aeruginosa, and Escherichia coli, wherein the antimicrobial properties of the antimicrobial substrate exceed the antimicrobial properties of a corresponding substrate without the antimicrobial compound.

### Claim 10

An antimicrobial substrate, the antimicrobial substrate comprising:
a substrate; and
a conjugated polyelectrolyte comprising a subunit having the following structure:
wherein
at each occurrence, R1 is independently chosen from:
at each occurrence, X is —O—, —NH—, or —S—,
at each occurrence, R3 is a (C1-C20)hydrocarbylene interrupted by 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9 heteroatoms,
at each occurrence, R4 is independently chosen from —H, —R5, -(1,4-substituted 1,4-diazabicyclo[2.2.2]octane-1,4-diium)-R5, 3-R5-substituted imidazolium, pyridinium, —SO3−, —CO2H, —CO2−, —N+(R5)3, and —N(R5)2,
at each occurrence, R5 is independently chosen from a substituted or unsubstituted (C1-C10)hydrocarbyl,
at each occurrence, Y is independently chosen from a bond and —C≡C—,
at each occurrence, R2 is a bond, and
at each occurrence, Z is a bond.

### Claim 11 (depends on 10)

The antimicrobial substrate of claim 10, wherein in the substrate is chosen from a wipe, a tissue, a bandage, a medical device, surgical instrument, warfighter machinery, a sponge, a textile, a diaper, a counter-top, a food preparation surface, a wound dressing, a dressing for surgical incisions, a keyboard surface, a packing for wounds, a packing for surgical incisions, a nasal packing, and a feminine care product.

### Claim 12 (depends on 10)

The antimicrobial substrate of claim 10, wherein the conjugated polyelectrolyte comprises terminal groups independently chosen from —H, -L-H, -L-C≡CH, -L-RT, -L-RL—RT, -L-C≡C—RT, -L-C≡C—RL—RT, and -L-RL—C≡C—RL—RT, -L-C≡C—RL—C≡C—RL—RT, wherein
at each occurrence, RTis independently chosen from —H, —Br, —(C1-C10)alkyl, —C(O)—OH, —C(O)—O((C1-C10)alkyl), —(C1-C10)alkylene-N((C1-C10)alkyl)3+X−, —O—(C10-C10)alkylene-N((C1-C10)alkyl)3+X−, wherein X− is a counterion,
at each occurrence, RL is independently chosen from a substituted or unsubstituted phenylene, thiophenylene, azulenylene, heptalenylene, biphenylene, indacenylene, fluorenylene, phenanthrenylene, triphenylenylene, pyrenylene, naphthacenylene, chrysenylene, biphenylenylene, anthracenylene, naphthylene, and -(1,4-substituted 1,4-diazabicyclo[2.2.2]octane-1,4-diium)-, and
at each occurrence, L is independently chosen from a bond, —(C1-C10)alkylene-, and —O—(C1-C10)alkylene-.

### Claim 13 (depends on 10)

The antimicrobial substrate of claim 10, wherein:
R1 has the structure:
at each occurrence, R3 is independently chosen from a (C1-C10)alkylene,
at each occurrence, R4 is independently chosen from -(1,4-substituted 1,4-diazabicyclo[2.2.2]octane-1,4-diium)-R5, 3-R5-substituted-imidazolium, pyridinium, and —N+(R5)3,
at each occurrence, R5 is independently chosen from (C1-C10)alkyl, and
at each occurrence, Y is a bond.

### Claim 14 (depends on 10)

The antimicrobial substrate of claim 10, wherein:
R1 has the structure:
at each occurrence, R3 is independently chosen from a (C1-C20)hydrocarbylene interrupted by 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9 heteroatoms,
at each occurrence, R5 is independently chosen born a substituted or unsubstituted (C1-C10)hydrocarbyl, and
at each occurrence, Y is a bond.

### Claim 15 (depends on 14)

The antimicrobial substrate of claim 14, wherein:
at each occurrence, R3 is a (C1-C10)alkylene interrupted by 0, 1, 2, 3, or 4 oxygen atoms,
at each occurrence, R5 is independently chosen from a (C1-C5)alkyl, and
at each occurrence, Y is a bond.

### Claim 16 (depends on 10)

The antimicrobial substrate of claim 10, wherein
at each occurrence, X is —O—,
at each occurrence, R3 is a (C2-C4)alkylene,
at each occurrence, Y is —C≡C—, and
at each occurrence, —R4 is chosen from —N+(CH3)3, —N(CH3)2, —SO3−,

### Claim 17 (depends on 10)

The antimicrobial substrate of claim 10, wherein
at each occurrence, R1 has the structure:

### Claim 18 (depends on 10)

The antimicrobial substrate of claim 10, wherein
at each occurrence, R1 has the structure:

### Claim 19 (depends on 10)

The antimicrobial substrate of claim 10, wherein the conjugated polyelectrolyte is non-leachably bound to the substrate.

### Claim 20 (depends on 10)

The antimicrobial substrate of claim 10, wherein the antimicrobial substrate exhibits antimicrobial properties comprising prevention of growth of at least one of Gram-positive Staphylococcus aureus, Gram-negative Pseudomonas aeruginosa, and Escherichia coli, wherein the antimicrobial properties of the antimicrobial substrate exceed the antimicrobial properties of a corresponding substrate without the antimicrobial compound.