IP Library Granted Patent US 9,380,784
Granted Patent B2
US 9,380,784 · App. 13/055,221 · Granted Jul 5, 2016

Antimicrobial compositions and methods of use

Inventors: Charles Derby (Decatur, GA); Binghe Wang (Marietta, GA); Phang C. Tai (Atlanta, GA); Ko-Chun Ko (Atlanta, GA); Michiya Kamio (Tokyo, JP)
A01N59/00
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Quick Facts
Patent No.
US 9,380,784
App. No.
13/055,221
Granted
Jul 5, 2016
Kind
B2
Abstract

Disclosed herein are antimicrobial compositions, kits, and articles of manufacture. Further disclosed herein are methods for treating surfaces, including tissue, inter alia, wounds, with the disclosed compositions.

Claims (100)

1. An antimicrobial composition, comprising:

a) 6-amino-2-ketohexanoic acid; and

b) a source of hydrogen peroxide;

wherein the composition has a pH of from about 3 to about 8;

the concentration of 6-amino-2-ketohexanoic acid is from about 15 mM to about 30 mM in the final composition; the concentration of the hydrogen peroxide obtained from the source of hydrogen peroxide is from about 0.5 mM to about 10 mM in the final composition; and provided the concentration of the 6-amino-2-ketohexanoic acid and source of hydrogen peroxide are not the same.

2. The composition according to claim 1 , wherein the pH is from about 5 to about 7.

3. The composition according to claim 1 , wherein the pH is from about 5 to about 6.

4. The composition according to claim 1 , wherein the pH is from about 4.5 to about 5.5.

5. The composition according to claim 1 , wherein the pH is about 5.

6. The composition according to claim 1 , wherein the pH is about 6.

7. The composition according to claim 1 , wherein the concentration of 6-amino-2-ketohexanoic acid is from about 20 mM to about 30 mM in the final composition.

8. The composition according to claim 1 , wherein the concentration of 6-amino-2-ketohexanoic acid is from about 25 mM to about 30 mM in the final composition.

9. The composition according to claim 1 , wherein the concentration of hydrogen peroxide is from about 0.5 mM to about 7 mM in the final composition.

10. The composition according to claim 1 , wherein the concentration of hydrogen peroxide is from about 1 mM to about 5 mM in the final composition.

11. The composition according to claim 1 , wherein the concentration of hydrogen peroxide is from about 1 mM to about 4 mM in the final composition.

12. The composition according to claim 1 , wherein the concentration of hydrogen peroxide is from about 2 mM to about 5 mM in the final composition.

13. A composition according to claim 1 , further comprising a surfactant.

14. A composition according to claim 1 , further comprising a stabilizer.

15. A composition according to claim 1 , further comprising a buffer system.

16. A composition comprising:

A) a first component in the form of a concentrate comprising from about 0.01% by weight to about 90% by weight of 6-amino-2-ketohexanoic acid; and

B) a second component containing a source of hydrogen peroxide, comprising:

a) from about 0.01% by weight to about 30% by weight of hydrogen peroxide;

b) from about 0.01% to about 50% by weight of a stabilizing system; and

c) a carrier;

wherein when components (A) and (B) are combined the concentration of 6-amino-2-ketohexanoic acid is from about 15 mM to about 30 mM in the final composition; and

the concentration of hydrogen peroxide is from about 0.5 mM to about 10 mM in the final composition.

17. The composition according to claim 16 , wherein the concentration of 6-amino-2-ketohexanoic acid is from about 20 mM to about 30 mM in the final composition.

18. The composition according to claim 16 , wherein the concentration of 6-amino-2-ketohexanoic acid is from about 25 mM to about 30 mM in the final composition.

19. The composition according to claim 16 , wherein the concentration of hydrogen peroxide is from about 1 mM to about 5 mM in the final composition.

20. The composition according to claim 16 , wherein the concentration of hydrogen peroxide is from about 1 mM to about 4 mM in the final composition.

21. The composition according to claim 16 , wherein the concentration of hydrogen peroxide is from about 2 mM to about 5 mM in the final composition.

22. A composition comprising:

A) a first component in the form of a solid concentrate comprising from about 0.01% by weight to about 100% by weight of 6-amino-2-ketohexanoic acid and

B) a second component, comprising:

a) hydrogen peroxide;

b) a stabilizing system; and

c) a carrier;

wherein when components (A) and (B) are combined the concentration of 6-amino-2-ketohexanoic acid is from about 15 mM to about 30 mM in the final composition; and the concentration of hydrogen peroxide is from about 0.5 mM to about 10 mM in the final composition.

23. An antimicrobial composition, comprising:

a) from about 4 g to about 6 g of 6-amino-2-ketohexanoic acid;

b) 5.7 mL of a 3% solution of hydrogen peroxide; and

c) citric acid/sodium citrate buffer;

wherein the composition has a pH about 5.5.

24. An antimicrobial composition, comprising:

a) one or more α-keto acids having the formula:

wherein R 1 is a nitrogen atom comprising unit chosen from:

i) —NR 3a R 3b ;

ii) —NR 4 C(═R 5 )R 6 ;

iii) —NR 7 NR 8a R 8b ;

iv) —N═R 9 ; or

v) —C(═NR 10 )R 11 ;

R 3a and R 3b are each independently chosen from:

i) hydrogen;

ii) C 1 -C 4 linear, C 3 -C 4 branched or C 3 -C 4 cyclic alkyl; or

iii) hydroxyl;

R 4 is:

i) hydrogen; or

ii) C 1 -C 4 linear, C 3 -C 4 branched or C 3 -C 4 cyclic alkyl;

R 5 is:

i) O;

ii) S; or

iii) NR 12 ; R 12 is hydrogen, hydroxyl, or C 1 -C 4 linear, C 3 -C 4 branched or C 3 -C 4 cyclic alkyl;

R 6 is:

i) hydrogen;

ii) C 1 -C 4 linear, C 3 -C 4 branched or C 3 -C 4 cyclic alkyl;

iii) C 1 -C 4 linear, C 3 -C 4 branched or C 3 -C 4 cyclic alkoxy; or

iv) —NR 13a R 13b ; R 13a and R 13b are each independently hydrogen or C 1 -C 4 linear, C 3 -C 4 branched or C 3 -C 4 cyclic alkyl;

R 7 , R 8a , and R 8b are each independently chosen from:

i) hydrogen; or

ii) C 1 -C 4 linear, C 3 -C 4 branched or C 3 -C 4 cyclic alkyl;

R 9 is:

i) NR 14 ; or

ii) CR 15a R l5b ;

R 14 , R 15a , and R 15b are each independently chosen from:

i) hydrogen; or

ii) C 1 -C 4 linear, C 3 -C 4 branched or C 3 -C 4 cyclic alkyl;

R 10 is hydrogen, hydroxyl, or C 1 -C 4 linear, C 3 -C 4 branched or C 3 -C 4 cyclic alkyl;

R 11 is chosen from:

i) NR 16 ; or

ii) CR 17a R l7b ;

R 16 is hydrogen or C 1 -C 4 linear, C 3 -C 4 branched or C 3 -C 4 cyclic alkyl;

R 17a and R 17b are each independently chosen from:

i) hydrogen; or

ii) C 1 -C 4 linear, C 3 -C 4 branched or C 3 -C 4 cyclic alkyl;

R 2a and R 2b are each independently chosen from:

i) hydrogen; or

ii) C 1 -C 4 linear, C 3 -C 4 branched or C 3 -C 4 cyclic alkyl;

the index x is an integer from 1 to 10; and

M is hydrogen or a water soluble cation; and

b) a source of hydrogen peroxide;

wherein the composition has a pH of from about 3 to about 8;

provided the concentration of the one or more α-keto acids and source of hydrogen peroxide are not the same.

25. A method for providing antimicrobial protection to a situs, comprising contacting the situs in need of protection against microorganisms with a composition according to claim 1 .

26. A method for sanitizing a situs, comprising contacting the situs with a composition according to claim 1 .

27. A method for disinfecting a situs, comprising contacting the situs with a composition according to claim 1 .

28. A method for controlling biofilms on a situs, comprising contacting the situs with a composition according to claim 1 .

29. A method according to claim 25 , wherein the situs is human or animal tissue.

30. A method according to claim 25 , wherein the situs is a hard surface.

31. A medical composition comprising a composition according to claim 1 and an effective amount of a pharmaceutically active agent.

Assignments (3)
CONFIRMATORY LICENSE Recorded Jan 11, 2017
From: GEORGIA STATE UNIVERSITY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 041329/0228 →
CONFIRMATORY LICENSE Recorded Jan 8, 2015
From: GEORGIA STATE UNIVERSITY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 034745/0145 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 25, 2013
From: DERBY, CHARLES; WANG, BINGHE; TAI, PHANG C.; KO, KO CHUN; KAMIO, MICHIYA
To: GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION, INC.
Reel/Frame 031480/0652 →
Continuity (2)
Provisional Application 61083790 · Jul 25, 2008
Related Publication 20110165261A1 · Jul 7, 2011