Chitosan-derivative compounds and methods of controlling microbial populations

• US 9,029,351 B2
• Filed: 01/13/2014
• Issued: 05/12/2015
• Est. Priority Date: 06/02/2006
• Status: Active Grant

• Current Assignee: Synedgen, Inc.
• Original Assignee: Synedgen, Inc.
• Inventors: Baker, Shenda M., Wiesmann, William P.
• Primary Examiner(s): Bland, Layla
• Application Number:
  US14/153,699
• Publication Number:
  US 20140301955A1
• Time in Patent Office: 484 Days
• Field of Search: None
• US Class Current: 514/55
• CPC Class Codes: A61K 31/722 Chitin, chitosan
• CPC Class Codes: A61K 8/736 Chitin; Chitosan; Derivatives thereof
• CPC Class Codes: A61L 2/232 layered or coated
• CPC Class Codes: A61L 2/235 cellular, porous or foamed
• CPC Class Codes: A61L 2202/23 Containers, e.g. vials, bottles, syringes, mail
• CPC Class Codes: A61L 2202/24 Medical instruments, e.g. endoscopes, catheters, sharps
• CPC Class Codes: A61P 1/04 for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
• CPC Class Codes: A61P 17/02 for treating wounds, ulcers, burns, scars, keloids, or the like
• CPC Class Codes: A61P 31/00 Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
• CPC Class Codes: A61P 31/04 Antibacterial agents
• CPC Class Codes: A61P 31/12 Antivirals
• CPC Class Codes: A61Q 11/00 Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
• CPC Class Codes: A61Q 17/005 Antimicrobial preparations
• CPC Class Codes: C08B 37/003 Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
• CPC Class Codes: C08L 5/08 Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
• 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 is directed to chitosan-derivative compounds and structures, methods of making chitosan-derivative compounds and methods for controlling, inhibiting and enhancing microbial populations in a variety of environments. The present invention is also directed to the control, inhibition and enhancement of microbial populations in animals, particularly humans. The microbial populations include bacteria, viruses and other pathogens where control of microbial populations are a necessity. The chitosan-derivative compounds of the present invention include chitosan-arginine compounds, related chitosan-L/D unnatural amino acid compounds, chitosan-acid amine compounds, chitosan-L/D natural amino acid derivative compounds, co-derivatives of the chitosan-derivative compounds, salts of the chitosan derivative compounds, and chitosan-guanidine compounds.

Claims

1. An oral care method for controlling microbial activity in an individual comprising administering functionalized chitosan-arginine compounds that are soluble at physiologic pH, in a therapeutically effective amount and in a therapeutically effective excipient, wherein the compounds are between 2% and 50% functionalized;

are substantially free of compounds having a molecular weight of less than 5000 Da, and wherein the compounds are substantially free of polyarginine polymers.

2. The method as recited in claim 1, wherein said pH is between 6.8 and 7.4.

3. The method as recited in claim 1, wherein said chitosan-arginine is at least 6% but no more than 30% functionalized.

4. The method as recited in claim 3, wherein said method comprises preventing biofilm formation.

5. The method as recited in claim 1, wherein said method comprises inhibiting planktonic growth of Gram-negative bacteria.

6. The method as recited in claim 5 wherein said Gram-negative bacteria are selected from the group consisting of Escherichia coli, Pseudomonas aeruginosa, Pseudomonas fluorescens, Acinetobacter baumannii, Kelbsiella pneumoniae, Shigella Flexneri, Salmonella typhi and Proteus mirabilis.

7. The method as recited in claim 1, wherein said method comprises inhibiting planktonic growth of Gram-positive bacteria.

8. The method as recited in claim 7, wherein said Gram-positive bacteria are selected from the group consisting of Bacillus subtilis, Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus mutans and Streptococcus pyogens.

9. The method as recited in claim 1, further comprising controlling microbial populations in animals.

10. The method as recited in claim 1, further comprising controlling microbial populations in humans.

11. An oral care method for controlling microbial populations comprising administering a purified preparation comprising a chitosan-derivative compound of the following formula:

12. The method as recited in claim 11, wherein the compound comprises the following a molecular weight between 25,000 and 350,000 Da, solubility at pH between 6.8 and 7.4, wherein said q is at least 0.20 and said functionalization is between 6% and 30%.

13. The method as recited in claim 11, wherein said method comprises preventing biofilm formation.