Conjugated polyelectrolytes and methods of using the same

Patent metadata

Field	Value
Publication number	US-9750250-B2
Application number	US-201615018179-A
Country	US
Kind code	B2
Filing date	Feb 8, 2016
Priority date	Jan 14, 2015
Publication date	Sep 5, 2017
Grant date	Sep 5, 2017

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 —R 1 —Y—R 2 —Z—. At each occurrence, R 1 is independently chosen from 1,4-bonded phenylene substituted by —X—R 3 —R 4 j times and 2,5-bonded thiophene substituted by —X—R 3 —R 4 j times. At each occurrence, Y is independently chosen from a bond and —C≡C—. At each occurrence, R 2 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, R 3 , and R 4 are as defined herein.

First claim

What is claimed is:

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, R 1 has the structure:

at each occurrence, X is a bond, —O—, —NH—, or —S—,
at each occurrence, R 3 is a (C 1 -C 20 )hydrocarbylene interrupted by 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9 heteroatoms,
at each occurrence, R 5 is independently chosen from a substituted or unsubstituted (C 1 -C 10 )hydrocarbyl,
at each occurrence, Y is independently chosen from a bond and —C≡C—,
at each occurrence, R 2 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—.

2. 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.

3. 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-R T , -L-R L —R T , -L-C≡C—R T , -L-C≡C—R L —R T , and -L-R L —C≡C—R L —R T , -L-C≡C—R L —C≡C—R L —R T , wherein
at each occurrence, R T is independently chosen from —H, —Br, —(C 1 -C 10 )alkyl, —C(O)—OH, —C(O)—O((C 1 -C 10 )alkyl), —(C 1 -C 10 )alkylene-N((C 1 -C 10 )alkyl) 3 + X − , —O—(C 1 -C 10 )alkylene-N((C 1 -C 10 )alkyl) 3 + X − , wherein X − is a counterion,
at each occurrence, R L 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, —(C 1 -C 10 )alkylene-, and —O—(C 1 -C 10 )alkylene-.

4. The antimicrobial substrate of claim 1 , wherein
at each occurrence, X is —O—,
at each occurrence, R 3 is a (C 2 -C 4 )akylene,
at each occurrence, Y is —C≡C—,
at each occurrence, R 2 is a bond, and
at each occurrence, Z is a bond.

5. The antimicrobial substrate of claim 1 , wherein
at each occurrence, X is —O—,
at each occurrence, R 3 is a (C 1 -C 10 )alkylene interrupted by 0, 1, 2, 3, or 4 oxygen atoms,
at each occurrence, R 5 is independently chosen from a (C 1 -C 5 )alkyl,
at each occurrence, Y is —C≡C—,
at each occurrence, R 2 is a bond, and
at each occurrence, Z is a bond.

6. The antimicrobial substrate of claim 1 , wherein
at each occurrence, X is —O—,
at each occurrence, R 3 is a (C 2 -C 4 )alkylene,
at each occurrence, Y is —C≡C—,
at each occurrence, R 2 is independently chosen from a 1,4-substituted phenylene and a 2,5-substituted thiophenylene, and
at each occurrence, Z is a —C≡C—.

7. The antimicrobial substrate of claim 1 , wherein
at each occurrence, X is —O—,
at each occurrence, R 3 is a (C 1 -C 10 )alkylene interrupted 0, 1, 3, or 4 oxygen atoms,
at each occurrence, R 5 is independently (C 1 -C 5 )alkyl,
at each occurrence, Y is —C≡C—,
at each occurrence, R 2 is a phenylene, and
at each occurrence, Z is a —C≡C—.

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

9. 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.

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, R 1 is independently chosen from:

at each occurrence, X is —O—, —NH—, or —S—,
at each occurrence, R 3 is a (C 1 -C 20 )hydrocarbylene interrupted by 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9 heteroatoms,
at each occurrence, R 4 is independently chosen from —H, —R 5 , -(1,4-substituted 1,4-diazabicyclo[2.2.2]octane-1,4-diium)-R 5 , 3-R 5 -substituted imidazolium, pyridinium, —SO 3 − , —CO 2 H, —CO 2 − , —N + (R 5 ) 3 , and —N(R 5 ) 2 ,
at each occurrence, R 5 is independently chosen from a substituted or unsubstituted (C 1 -C 10 )hydrocarbyl,
at each occurrence, Y is independently chosen from a bond and —C≡C—,
at each occurrence, R 2 is a bond, and
at each occurrence, Z is a bond.

11. 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.

12. The antimicrobial substrate of claim 10 , wherein the conjugated polyelectrolyte comprises terminal groups independently chosen from —H, -L-H, -L-C≡CH, -L-R T , -L-R L —R T , -L-C≡C—R T , -L-C≡C—R L —R T , and -L-R L —C≡C—R L —R T , -L-C≡C—R L —C≡C—R L —R T , wherein
at each occurrence, R T is independently chosen from —H, —Br, —(C 1 -C 10 )alkyl, —C(O)—OH, —C(O)—O((C 1 -C 10 )alkyl), —(C 1 -C 10 )alkylene-N((C 1 -C 10 )alkyl) 3 + X − , —O—(C 10 -C 10 )alkylene-N((C 1 -C 10 )alkyl) 3 + X − , wherein X − is a counterion,
at each occurrence, R L 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, —(C 1 -C 10 )alkylene-, and —O—(C 1 -C 10 )alkylene-.

13. The antimicrobial substrate of claim 10 , wherein:
R 1 has the structure:

at each occurrence, R 3 is independently chosen from a (C 1 -C 10 )alkylene,
at each occurrence, R 4 is independently chosen from -(1,4-substituted 1,4-diazabicyclo[2.2.2]octane-1,4-diium)-R 5 , 3-R 5 -substituted-imidazolium, pyridinium,

Assignees

• Whitten David G
• Pappas Harry Craig
• Hill Eric H
• Schanze Kirk S
• Parthasarathy Anand
• Huang Yun
• Corbitt Thomas S
• Stc Unm
• Univ Florida

Inventors

• Whitten David G
• Pappas Harry Craig
• Hill Eric H
• Schanze Kirk S
• Parthasarathy Anand
• Huang Yun
• Corbitt Thomas S

Classifications

• C07D409/06

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• C07D233/64

  with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine · CPC title

• H01B1/122 Primary

  Ionic conductors · CPC title

• C08L65/00

  Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C08L7/00 - C08L57/00, C08L61/00 take precedence); Compositions of derivatives of such polymers · CPC title

• C08G61/126

  with a five-membered ring containing one sulfur atom in the ring · CPC title