CYCLIC ANTIMICROBIAL PEPTIDES

• US 20140303071A1
• Filed: 06/20/2014
• Published: 10/09/2014
• Est. Priority Date: 12/22/2005
• Status: Active Grant

• Current Assignee: NovaBiotics Ltd.
• Original Assignee: NovaBiotics Ltd.
• Inventors: O'NEIL, Deborah
• Granted Patent: US 9,181,303 B2
• Time in Patent Office: Days
• US Class Current: 514/2.6
• CPC Class Codes: A61K 38/00 Medicinal preparations containing peptides peptides containing beta-lactam rings A61K31/00; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, A61K31/00; ergot alkaloids of the cyclic peptide type A61K31/48; containing macromolecular compounds having statistically distributed amino acid units A61K31/74; medicinal preparations containing antigens or antibodies A61K39/00; medicinal preparations characterised by the non-active ingredients, e.g. peptides as drug carriers, A61K47/00
• CPC Class Codes: C07K 14/4723 Cationic antimicrobial peptides, e.g. defensins
• CPC Class Codes: C07K 7/64 Cyclic peptides containing only normal peptide links
• CPC Class Codes: Y02A 50/30 Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Abstract

The present invention relates to cyclic cationic peptides and their use in the treatment of microbial infections.

Claims

1. A cyclic peptide, or variant thereof, comprising amino acids according to the formula I:

((X)l(Y)m)n  

 

(I)

wherein l and m are integers from 0 to 10 such that both l and m are not 0, n is an integer from 1 to 10, and

X and Y, which may be the same or different, are an amino acid selected from the group consisting of;

arginine, lysine and ornithine.

2. The cyclic peptide of claim 1, wherein the peptide comprises from 2 to 50 amino acids.

10. A composition comprising a cyclic peptide of claim 1 and a pharmaceutically acceptable carrier, excipient or diluent.

13. A method of treating a microbial infection in a subject, comprising administering to the subject a therapeutically effective amount of a composition of claim 10.

3. A cyclic peptide comprising from 3 to 15 contiguous arginine residues.

4. The cyclic peptide of claim 3, wherein the cyclic peptide comprises from 5 to 13 contiguous arginine residues.

5. The cyclic peptide of claim 3, wherein the cyclic peptide comprises from 4 to 7 contiguous arginine residues.

11. A composition comprising a cyclic peptide of claim 3 and a pharmaceutically acceptable carrier, excipient or diluent.

14. A method of treating a microbial infection in a subject, comprising administering to the subject a therapeutically effective amount of a composition of claim 11.

15. The method of claim 14, wherein the microbial infection is a bacterial infection.

16. The method of claim 15, wherein the bacterial infection is selected from the group consisting of:

Staphylococcus spp.;

Chlamydia spp.;

Enterococcus spp.;

Streptococcus pyogenes;

Listeria spp.;

Pseudomonas spp.;

Mycobacterium spp.;

Enterobacter spp.;

Campylobacter spp.;

Salmonella spp.;

Streptococcus spp.;

Helicobacter spp.;

Neisseria spp.;

Borrelia burgdorferi;

Shigella spp.;

Escherichia coli;

Haemophilus spp.;

Francisella tularensis;

Bacillus spp.;

Clostridia spp.;

Yersinia spp.;

Treponema spp.;

Burkholderia spp.; and

Propionibacterium spp.

6. A cyclic peptide comprising 7 contiguous arginine residues.

7. The cyclic peptide of claim 6, wherein the arginine residues are D-amino acids.

8. The cyclic peptide of claim 6, wherein the arginine residues are L-amino acids.

12. A composition comprising a cyclic peptide of claim 6, and a pharmaceutically acceptable carrier, excipient or diluent.

17. A method of treating a microbial infection in a subject, comprising administering to the subject a therapeutically effective amount of a composition of claim 12.

18. The method of claim 17, wherein the microbial infection is a bacterial infection.

19. The method of claim 18, wherein the bacterial infection is selected from the group consisting of:

Staphylococcus spp.;

Chlamydia spp.;

Enterococcus spp.;

Streptococcus pyogenes;

Listeria spp.;

Pseudomonas spp.;

Mycobacterium spp.;

Enterobacter spp.;

Campylobacter spp.;

Salmonella spp.;

Streptococcus spp.;

Helicobacter spp.;

Neisseria spp.;

Borrelia burgdorferi;

Shigella spp.;

Escherichia coli;

Haemophilus spp.;

Francisella tularensis;

Bacillus spp.;

Clostridia spp.;

Yersinia spp.;

Treponema spp.;

Burkholderia spp.; and

Propionibacterium spp.

9. A cyclic peptide consisting of 7 arginine residues.