INHIBITION OF BIOFILM FORMATION BY 1,2,3,4,6-PENTA-O-GALLOYL-D-GLUCOPYRANOSE

• US 20120321566A1
• Filed: 09/19/2011
• Published: 12/20/2012
• Est. Priority Date: 06/17/2011
• Status: Active Grant

• Current Assignee: Chang GUNG University
• Original Assignee: Chang GUNG University
• Inventors: Chang, Fang-Rong, Liu, Shih-Tung, Lin, Mei-Hui, Hua, Mu-Yi, Yang, Hung-Wei
• Granted Patent: US 9,181,290 B2
• Time in Patent Office: Days
• US Class Current: 424/48
• CPC Class Codes: A01N 43/16 with oxygen as the ring hetero atom
• CPC Class Codes: A61K 31/7032 attached to a polyol, i.e. compounds having two or more free or esterified hydroxy groups, including the hydroxy group involved in the glycosidic linkage, e.g. monoglucosyldiacylglycerides, lactobionic acid, gangliosides
• CPC Class Codes: A61K 8/60 Sugars; Derivatives thereof
• CPC Class Codes: A61K 9/0014 Skin, i.e. galenical aspects of topical compositions non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00
• CPC Class Codes: A61K 9/0056 Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
• CPC Class Codes: A61K 9/0058 Chewing gums non-medicinal aspects, preparing chewing gum A23G4/00; chewing gum for care of the teeth or oral cavity, e.g. with breath freshener A61Q11/00
• CPC Class Codes: A61K 9/006 Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays
• CPC Class Codes: A61P 17/02 for treating wounds, ulcers, burns, scars, keloids, or the like
• 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: C07H 13/08 having the esterifying carboxyl radicals directly attached to carbocyclic rings
• 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

Disclosed herein are an anti-biofilm composition and a method to inhibit or prevent cell adhesion and/or biofilm formation by a microorganism, in which use of 1,2,3,4,6-penta-O-galloyl-D-glucopyranose (PGG) is involved therein.

Claims

1. A method to prevent or inhibit cell adhesion and/or biofilm formation by a microorganism, comprising applying to a site in need of such treatment a composition containing 1,2,3,4,6-penta-O-galloyl-D-glucopyranose (PGG).

2. The method of claim 1, wherein the PGG is an α

-anomer of PGG, a β

-anomer of PGG, an analogue of PGG, or a mixture thereof.

3. The method of claim 1, wherein applying the composition to said site results in a coating or thin film or layer formed on said site so that formation of a biofilm on said site is prevented or inhibited.

4. The method of claim 1, wherein the composition further comprises a film-forming material that contributes to the formation of a coating or a thin film or layer on said site after application of the composition.

5. The method of claim 4, wherein the film-forming material is selected from the group consisting of polyaniline, poly(acrylic acid), polypyrrole, poly(ethylene glycol), poly N-methylaniline, chitosan, alginate, pectimic acid, dextran, collagen, polyvinyl, polyethylene, polyurethane, polypropylene, silicone, polymethacrylic acid, polymaleic acid, poly-(maleic acid monoester), poly(ethylene glycol), polyaspartic acid, polyglutamic acid, polycarboxylic acid anhydrides, polyamines, polyethylene imine, polyvinylamine, polylysine, poly-(dialkylaminoethyl methacrylate), poly-(dialkylaminomethyl styrene), poly-(vinylpyridine), poly-(2-methacryloxyethyl trialkyl ammonium ion), poly-(vinylbenzyl trialkyl ammonium ions), poly-(N,N-alkylpyridinium ion), poly-(dialkyloctamethylene ammonium ion), polysulfonates, poly-(vinyl sulfonate), poly-(styrene sulfonate), collodion, nylon, rubber, plastic, polyesters, Dacron™

(polyethylene tetraphthalate), Teflon™

(polytetrafluoroethylene), latex, elastomers and Dacron (sealed with gelatin, collagen or albumin), cyanoacrylates, methacrylates, homopolymer of lactide, homopolymer of glycolide (PGA), copolymer of PLA and PGA, and combinations thereof.

6. The method of claim 1, wherein the composition further comprises an antimicrobial agent selected from the group consisting of iodoacetamide, N-acetylcysteine, N-phenyl maleimide, triclosan, rifampicin, cefamandole nafate, ciprofloxacin, oxacillin, clarithromycin, cefazolin, azithromycin, tobramycin, polymyxin, linezolid, colistin, gentamycin, vancomycin, daptomycin, tigecycline, nitrofurazone, bismuth ethanedithiol, chitosan, Epigallocatechin gallate, sodium usnate, 5-fluorouracil, detergents, chelating agents, silver compounds, bacteriophage, antimicrobial enzymes, sugar alcohols, maleimides, cadexomer iodine, methylene blue, gentian violet, medium chain dextrans, and mixtures thereof.

7. The method of claim 1, wherein said site is an industrial environment, a residential environment, a household environment, a medical environment, an aquatic environment, a laboratory, or a workplace.

8. The method of claim 1, wherein the site is a surface made of a material selected from the group consisting of metals or metal alloys, glass, ceramic, glaze ceramic, porcelain, wood, chrome, plastics, fibers, rubbers, or combinations thereof.

9. The method of claim 1, wherein the site is a hydrophobic surface made of polystyrene, polycarbonate, polyethylene, polypropylene, polyester, polyurethane, polyvinyl chloride, silicon rubber, latex rubber, nylon, Teflon, polytetrafluorocarbons, polymethylmethacrylate, acrylic co-polymer, cellophane, Dacron, polysulfon, or combinations thereof.

10. The method of claim 1, wherein the site is a hydrophilic surface made of glass, ceramics, hydroxyapatite, hydrogel, stainless steel, titanium alloys, nickel alloy, platinum-Iridium, Co—

Cr alloy, or combinations thereof.

11. The method of claim 1, wherein the site is the inner and/or outer surface of a medical device.

12. The method of claim 1, wherein the microorganism is a Gram-positive or Gram-positive bacterial pathogen.

13. The method of claim 1, wherein the microorganism is a bacterial strain of Staphylococcus sp., Enterococcus sp., Acinetobacter baumannii, Streptococcus sp., Pseudomonas sp., Escherichia coli, Helicobacter sp., Chlamydia sp., Clostridia sp., Haemophilus sp., Shigella sp., Bacillus sp., Neisseria sp., Mycobacterium sp., Francisella fularensis;

Klebsiella sp., Yersinia sp., Propionibacterium sp., Burkholderia sp., Treponema sp., Enterobacter sp., Borrelia burgdorferi, Proteus mirabilis, Providentia sturtii, Serratia marcescens, Fusobacterium nucleatum, Aggregatibacter cictinontycetemcomitans, Salmonella sp.;

Listeria sp., Campylobacter sp., Bacteriodes sp., Prevotella sp., Corynebacterium sp., Porphyromonas sp., and Peptostreptococcus sp.

14. The method of claim 13, wherein the bacterial strain is a strain of Staphylococcus sp. selected form the group consisting of Staphylococcus aureus, Staphylococcus epidermidis, Staphylococcus epitkonidis, Staphylococcus agalactiae, Staphylococcus saprophyticus, Staphylococcus haemolyticus, Staphylococcus warneri, Staphylococcus hominis, Staphylococcus simulans, Staphylococcus lugdunensis, Staphylococcus schleiferi, Staphylococcus capitis, Staphylococcus caprae, Staphylococcus pasteuri, Staphylococcus cohnii, Staphylococcus xylosus, Staphylococcus saccharolyticu, and combinations thereof.

15. The method of claim 14, wherein the bacterial strain is a strain of S. aureus.

16. The method of claim 15, wherein the bacterial strain is a clinical strain of S. aureus that is sensitive to methicillin.

17. A method to prevent or inhibit the formation of a biofilm on at least a surface of a medical device, comprising treating the medical device with a composition containing 1,2,3,4,6-penta-O-galloyl-D-glucopyranose (PGG).

18. The method of claim 17, wherein the PGG is an α

-anomer of PGG, a β

-anomer of PGG, an analogue of PGG, or a mixture thereof.

19. The method of claim 17, wherein the medical device is one of the following:

devices used in invasive surgical, therapeutic or diagnostic procedures;

implantable medical devices;

artificial hearts;

artificial kidneys;

orthopedic pins, plates and implants;

catheters;

urological, biliary or endotracheal tubes;

peripherally insertable central venous catheters;

dialysis catheters;

long term tunneled central venous catheters;

peripheral venous catheters;

short term central venous catheters;

arterial catheters;

pulmonary catheters;

Swan-Ganz catheters;

urinary catheters;

peritoneal catheters;

long term urinary devices;

tissue bonding urinary devices;

artificial urinary sphincters;

urinary dilators;

ventricular or arterio-venous shunts;

breast implants;

penile prostheses;

vascular grafting prostheses;

heart valves;

artificial joints;

artificial larynxes;

otological implants;

vascular catheter ports;

wound drain tubes;

hydrocephalus shunts;

pacemakers; and

implantable defibrillators.

20. A method for treating a wound, comprising applying to the wound a composition containing 1,2,3,4,6-penta-O-galloyl-D-glucopyranose (PGG).

21. The method of claim 20, wherein the PGG is an α

-anomer of PGG, a β

-anomer of PGG, an analogue of PGG, or a mixture thereof.

22. The method of claim 20, wherein the composition is manufactured as a wound care ointment, gel, lotion or spray.

23. A method for treating a wound, comprising applying to the wound a wound care device containing 1,2,3,4,6-penta-O-galloyl-D-glucopyranose (PGG).

24. The method of claim 23, wherein the PGG is an α

-anomer of PGG, a β

-anomer of PGG, an analogue of PGG, or a mixture thereof.

25. The method of claim 23, wherein the wound care device is selected from the group consisting of non-resorbable gauze/sponge dressing, hydrophilic wound dressing, occlusive wound dressing, hydrogel wound dressing, burn dressing, and spray-applicators for wound healing.

26. A method to treat or prevent an oral infection, comprising applying to an oral cavity an oral health product containing 1,2,3,4,6-penta-O-galloyl-D-glucopyranose (PGG).

27. The method of claim 26, wherein the PGG is an α

-anomer of PGG, a β

-anomer of PGG, an analogue of PGG, or a mixture thereof.

28. The method of claim 26, wherein the oral health product is manufactured in a form selected from films, tapes, gels, microspheres, lozenges, chewing gums, dentrifices, and mouthwash.

29. An anti-biofilm composition, comprising 1,2,3,4,6-penta-O-galloyl-D-glucopyranose (PGG).

30. The composition of claim 29, wherein the PGG is an α

-anomer of PGG, a β

-anomer of PGG, an analogue of PGG, or a mixture thereof.

31. The composition of claim 29, wherein the composition forms an anti-biofilm coating or thin film or layer on a site treated therewith.

32. The composition of claim 29, further comprising a film-forming material that contributes to the formation of a coating or a thin film or layer on a site treated with the composition.

33. The composition of claim 29, wherein the film-forming material is selected from the group consisting of polyaniline, poly(acrylic acid), polypyrrole, poly(ethylene glycol), poly N-methylaniline, chitosan, alginate, pectimic acid, dextran, collagen, polyvinyl, polyethylene, polyurethane, polypropylene, silicone, polymethacrylic acid, polymaleic acid, poly-(maleic acid monoester), poly(ethylene glycol), polyaspartic acid, polyglutamic acid, polycarboxylic acid anhydrides, polyamines, polyethylene imine, polyvinylamine, polylysine, poly-(dialkylaminoethyl methacrylate), poly-(dialkylaminomethyl styrene), poly-(vinylpyridine), poly-(2-methacryloxyethyl trialkyl ammonium ion), poly-(vinylbenzyl trialkyl ammonium ions), poly-(N,N-alkylpyridinium ion), poly-(dialkyloctamethylene ammonium ion), polysulfonates, poly-(vinyl sulfonate), poly-(styrene sulfonate), collodion, nylon, rubber, plastic, polyesters, Dacron™

(polyethylene tetraphthalate), Teflon™

(polytetrafluoroethylene), latex, elastomers and Dacron (sealed with gelatin, collagen or albumin), cyanoacrylates, methacrylates, homopolymer of lactide, homopolymer of glycolide (PGA), copolymer of PLA and PGA, and combinations thereof.

34. The composition of claim 29, further comprising an antimicrobial agent selected from the group consisting of iodoacetamide, N-acetylcysteine, N-phenyl maleimide, triclosan, rifampicin, cefamandole nafate, ciprofloxacin, oxacillin, clarithromycin, cefazolin, azithromycin, tobramycin, polymyxin, linezolid, colistin, gentamycin, vancomycin, daptomycin, tigecycline, nitrofurazone, bismuth ethanedithiol, chitosan, Epigallocatechin gallate, sodium usnate, 5-fluorouracil, detergents, chelating agents, silver compounds, bacteriophage, antimicrobial enzymes, sugar alcohols, maleimides, cadexomer iodine, methylene blue, gentian violet, medium chain dextrans, and mixtures thereof.

35. A composition for treating a wound, comprising 1,2,3,4,6-penta-O-galloyl-D-glucopyranose (PGG).

36. The composition of claim 35, wherein the PGG is an α

-anomer of PGG, a β

-anomer of PGG, an analogue of PGG, or a mixture thereof.

37. The composition of claim 35, which is manufactured as a wound care ointment, gel, lotion or spray.

38. A wound care device containing 1,2,3,4,6-penta-O-galloyl-D-glucopyranose (PGG).

39. The wound care device of claim 38, wherein the PGG is an α

-anomer of PGG, a β

-anomer of PGG, an analogue of PGG, or a mixture thereof.

40. The wound care device of claim 38, which is selected from the group consisting of non-resorbable gauze/sponge dressing, hydrophilic wound dressing, occlusive wound dressing, hydrogel wound dressing, burn dressing, and spray-applicators for wound healing.

41. An oral health product, comprising 1,2,3,4,6-penta-O-galloyl-D-glucopyranose (PGG).

42. The oral health product of claim 41, wherein the PGG is an α

-anomer of PGG, a β

-anomer of PGG, an analogue of PGG, or a mixture thereof.

43. The oral health product of claim 41, which is manufactured in a form selected from films, tapes, gels, microspheres, lozenges, chewing gums, dentrifices, and mouthwash.