WO2010062933A1 - Méthodes de traitement et de cicatrisation de plaie à l'aide de compositions à base de limonène - Google Patents

Méthodes de traitement et de cicatrisation de plaie à l'aide de compositions à base de limonène Download PDF

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Publication number
WO2010062933A1
WO2010062933A1 PCT/US2009/065860 US2009065860W WO2010062933A1 WO 2010062933 A1 WO2010062933 A1 WO 2010062933A1 US 2009065860 W US2009065860 W US 2009065860W WO 2010062933 A1 WO2010062933 A1 WO 2010062933A1
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Prior art keywords
limonene
wound
based composition
healing
bio
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PCT/US2009/065860
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English (en)
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Sahara Adams
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Sahara Adams
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Publication of WO2010062933A1 publication Critical patent/WO2010062933A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/01—Hydrocarbons
    • A61K31/015—Hydrocarbons carbocyclic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/31—Hydrocarbons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/006—Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses

Definitions

  • Limonene is a monocyclic monoterpene commonly found in nature, typically occurring in its D form in citrus and other plant species. In vitro analyses have revealed that D-limonene is effective in eradicating the following major gram-positive pathogens: Staphylococcus aureus, Staphylococcus epidermidis (both methicillin sensitive and resistant), Streptococcus pyogenes, Streptococcus mutans, and other beta hemolytic streptococci, Enter ococcus faec ⁇ lis, and Enter ococcus faecium (both vancomycin sensitive and resistant).
  • Staphylococcus aureus Staphylococcus epidermidis (both methicillin sensitive and resistant)
  • Streptococcus pyogenes Streptococcus mutans
  • beta hemolytic streptococci Enter ococcus faec ⁇ lis
  • Enter ococcus faecium
  • D-limonene is effective in eradicating the following gram-negative pathogens: Escherichia coli, Enterobactor cloacae, Klebsiella pneumoniae, Serratia marcescens, Pseudomonas aeruginosa, Acinetobacter baummii/haemolyticus, Paenibacillus polymyxa, and Stenotrophomonas maltophilia.
  • D-limonene is effective in eradicating various Bacillus species, such as Bacillus licheniformis, B.
  • methods for treating a wound include applying a limonene -based composition to a wound to inhibit growth of bacteria therein.
  • methods for treating a wound include applying a bio- film to a wound.
  • a limonene-based composition is included in the bio-film.
  • wound-healing compositions are disclosed herein.
  • the wound-healing compositions include a limonene-based composition and a carrier for the limonene-based composition.
  • FIGURE 1 shows the chemical structure of D-limonene.
  • the present disclosure is directed to methods for treating a wound and wound-healing compositions.
  • the methods for treating a wound and the wound-healing compositions each utilize limonene-based compositions.
  • the limonene-based compositions utilize limonene as an active ingredient for killing or inhibiting the growth of a variety of bacteria known to cause a number of infectious diseases in humans and animals.
  • the limonene-based compositions comprise D -limonene.
  • an effective amount of limonene e.g., D- limonene for inhibiting bacterial growth is placed in a limonene-based composition and is then applied to the human or animal.
  • limonene e.g., D- limonene
  • limonene-based compositions are disclosed herein.
  • the methods include applying a limonene-based composition to a wound to inhibit growth of bacteria therein.
  • the limonene-based composition comprises D- limonene.
  • the limonene-based composition is included in a spray. In other embodiments, the limonene-based composition is included in an ointment. In still other various embodiments, the limonene-based composition is included in a bio-film such as, for example, a bandage.
  • the wound treated by the limonene-based compositions is intra-oral (i.e., inside the oral cavity). In other embodiments, the wound treated by the limonene-based compositions is extra-oral (i.e., outside the oral cavity).
  • oral cavity refers to the mouth.
  • methods for treating a wound include applying a bio- film to a wound.
  • a limonene-based composition is included in the bio-film.
  • Bio-films include, for example, a bandage.
  • the limonene-based compositions of the present disclosure may comprise an ointment, topical spray or bio-film for intra-oral or extra-oral application to a wound.
  • wound-healing compositions include a limonene-based composition and a carrier for the limonene-based composition.
  • the limonene-based composition includes D-limonene.
  • the carrier is a bio-film such as, for example, a bandage.
  • the carrier is a liquid.
  • the carrier is a gel.
  • the limonene-based compositions may be included in a mouthwash.
  • D-limonene may be formulated in a mouthwash to be used as a rinse or a swab.
  • the limonene-based compositions may comprise a toothpaste.
  • toothpastes and mouthwashes containing limonene may be used for wound healing by killing or inhibiting the growth of common dental pathogens that are known to cause tooth decay and periodontal disease.
  • Such dental pathogens include bacteria such as, for example, Porphyromonas gingivalis, Bacteroides species, Actinobacillus action mycetemcomitons, Prevotella intermedia, Fusobacterium nucleatum, Bacteroides forsythus and other species, Campylobacter rectus, Eikenella corrodens, Peptostreptoloccus micros, Selenomonas sp., Eubacterium sp., Streptococcus intermedins, spirochetes Treponema denticola, and Treponema pallidum and syphillis.
  • the toothpastes and mouthwashes may also be useful in killing or inhibiting the growth of other pathogens that have been shown to colonize in the mouth, leading to various systemic diseases, such as, for example, bacterial endocarditis and arthritis.
  • Such toothpastes may also include base components (i.e., excipients) commonly known to those of ordinary skill in the art of toothpaste manufacture.
  • Such toothpastes may also include calcium and/or magnesium compounds to aid in strengthening the teeth.
  • Illustrative base components include, for example, (a) sorbitol, (b) water, (c) silica (e.g.
  • ZEODENT vended by Huber Corp.
  • glycerin e.g., glycerin
  • surfactants e.g., sodium lauryl sulfate or Polysorbate 20
  • binders and viscosifying agents e.g., CEKOL cellulose gum or xantham gum and
  • preservatives e.g., sodium benzoate and methyl parabens.
  • Flavoring agents, coloring agents and/or whitening agents may be optionally employed as well.
  • the limonene-based compositions of the present disclosure may comprise at least one base component (i.e., excipient) in addition to limonene.
  • the limonene is a highly purified limonene.
  • the limonene has a purity greater than about 98% by weight in some embodiments, greater than about 98.5% by weight in other embodiments, and greater than about 99% by weight in still other embodiments.
  • An illustrative purification technique for limonene is described in United States Patent 6,420,435, which is incorporated by reference herein in its entirety.
  • a concentration of limonene in the limonene-based compositions ranges from about 10% to about 40% by weight.
  • An illustrative toothpaste formulation includes the following components: about 10% to about 40% D-limonene, about 15% to about 35% sorbitol; about 15% to about 30% of a silica agent (e.g., ZEODENT 113 and/or ZEODENT 165), about 10% to about 20% water; about 5% to about 15% glycerin, about 2% to about 7% of surfactant (e.g., Polysorbate 20), about 1% to about 2% flavoring agent (e.g., sodium saccharin), about 0.5% to about 1.5% of titanium dioxide as a whitening agent, about 0.5% to about 1.5% binder (e.g., CEKOL 2000 gum), about 0.05% to about 0.15% of a preservative (e.g., sodium benzoate), about 0.25% to about 1.75% of calcium, and about 0.10% to about 1.75% of magnesium phosphate.
  • the toothpaste formulations comprise about 18% to about 22% D
  • An illustrative mouthwash formulation includes the following components: (a) about 15% to about 25% sorbitol, (b) about 10% to about 20% of polyethylene glycol, (c) about 2.5% to about 7.5% Polysorbate 20, (d) about 2.5% to about 15% D-limonene, (e) about 45% to about 65% water, (f) about 0.2% to about 0.5% sucralose, and (g) about 1.0% to 2.0% Bel wood Wintergreen.
  • Administration of the mouthwash is similar to conventional mouthwashes (i.e., about 30 ml is placed within the mouth and swished about therein for about 30 seconds prior to expectoration). The administrated dose and time within the mouth may be varied as desired.
  • pure limonene may be applied directly to a wound to promote healing thereof.
  • a small amount of limonene oil may be applied directly to the teeth or swabbed with a human or animal's mouth for the purpose of killing or inhibiting the growth bacteria therein.
  • limonene may be applied directly to an extra-oral wound.
  • the present disclosure also contemplates incorporation of small amounts of pure limonene (e.g., about 0.1 mL) within a chewing gum base. Upon chewing of the gum, the limonene is released from the gum base and dispersed within the oral cavity and onto the teeth.
  • the aforementioned limonene-based compositions may be incorporated within ointments, topical sprays, and/or bio-films for intra-oral or extra-oral application.
  • Intra-oral applications have been described hereinabove.
  • topical sprays and bio-films may be applied to a wounded area on the skin.
  • Such extra-oral application may be further promoted by rubbing for an ointment or spraying for a topical spray.
  • Bio -films may be used, for example, for treating wounded soldiers by applying a limonene-based composition to a wounded area. Such use of bio-films by wounded soldiers may advantageously lessen the incidence of battlefield related infections.
  • Example 1 In Vitro Activity of D-limonene against Various Bacteria.
  • Clinical isolates (10 5 bacteria/ml) (about 100 ⁇ l) of gram-positive pathogens (Staphylococcus aureus and epidermidis (both methicillin-sensitive and resistant) plus Enterococcus faecalis and faecium) along with a group of gram-negative pathogens (Escherichia coli, Enterobacter cloacae, Klebsiella pneumoniae and Serratia marcescens coupled with opportunistic pathogens Pseudomonas aeruginosa, Acinetobacter baummii/haemolyticus and Stenotrophomonas maltophi/a) were each inoculated into 2 ml of D-limonene, in accordance with the standard phenol-coefficient assay and other screening methodology for plant antimicrobial activity and incubated for 72 hrs.
  • a 2 ml broth media was used as a positive control.
  • the D-limonene used was purified to at least 98.5% via a distillation process with purity confirmed by HPLC. Aliquots were subsequently cultured at 24 hours, 48 hours, and 72 hours to determine the antimicrobial effect. Appropriate media was inoculated in accordance with NCCLS standards. Blood agar was used for the gram- positive organisms, while McConkey Agar was utilized for the gram-negative organisms. ATCC strains of S. aureus, E.faecalis, P. aeruginosa, and E. coli were used as controls organisms and compared to the clinical isolates of these pathogens.
  • Example 2 Preparation of a Toothpaste Comprising D-limonene.
  • a toothpaste formulation was manufactured by combining the following components:
  • Example 3 Preparation of Another Toothpaste Comprising D-limonene.
  • Another toothpaste formulation was manufactured by combining the following components:
  • Example 4 Activity of Standard Topical Anti-Bacterials, Nutriceuticals and Herbal Medications on Bacillus anthracis Strains.
  • the Steams and Ames strain of Bacillus anthracis were subjected to a battery of standard topical anti-bacterials, nutriceuticals, and herbal medications, including SILVADENE (generic silver sulfadiazine, vended by Hoescht Marion Roussel, now Par); SILVADENE with nystatin 0.025%; mafenide acetate, FURACIN (generic nitrofurazone, vended by Roberts), bacitracin with Polymyxin B (Poly B), silver nitrate, sodium hypochlorite (NaOCl), grapefruit seed extract (GSE), oleander extract with Aloe vera (Biotonics, San Antonio, Texas), and various concentrations of a new anti-infective solution called FX (Sterifx, Inc, Shreveport, Louisiana).
  • the zones of inhibition for the more lethal and pathogenic Ames strain were comparable to those of the Steams strain for the standard anti-infectives, nutraceuticals (i.e. GSE and D-limonene) and herbal products.
  • mafenide acetate and BACTROBAN were at the top of the susceptibility list, with inhibition zones of 34 mm and 35 mm, respectively.
  • the inhibitions zones of FX 4X and 12X were 35 mm and 46 mm, respectively.
  • GSE and FX product IX zones of inhibition were both 23 mm.
  • D-limonene's zone of inhibition was 21 mm.
  • SILVADENE's zone of inhibition was 18 mm, while SILVADENE with Nystatin was 14 mm.
  • the zone of inhibition for AgNO 3 was 16 mm, as was that of the Oleander Aloe vera product. Bacitracin, Polymyxin B and NaOCl were ineffective and showed no zones of inhibition.
  • the strains included ATCC strains of Paenibacillus polymyxa, Bacillus licheniformis, Bacillus subtilis, Bacillus sphaericus, Bacillus cereus and a wild Bacillus strain from a burn patient.
  • the anti-infectives tested were SILVADENE, mafenide acetate, furacin, BACTROBAN, Bacitracin plus polymyxin B, SILVADENE with Nystatin, 0.025% NaOCl, AgNO 3 , Grapefruit Seed Extract (GSE), D-limonene, Oleander extract with Aloe vera and various concentrations of a new anti- infective solution FX.
  • the sphaericus and P. polymyxa producing an inhibition zone of 22 mm.
  • FX 5X and Fx 1OX inhibited all Bacillus strains tested with an average inhibition zone size of 32 mm and 49 mm, respectively.
  • the Oleander extract produced an inhibition zone size of 18 mm, and D-limonene produced an inhibition zone of 21 mm.
  • the inhibition zone Of AgNO 3 was 16 mm.
  • Example 6 Antibacterial Activity of Toothpaste Formulations. 0.25 to 0.50 grams of each of three different toothpaste formulations (labeled C, D, and P) were applied to clinical isolates (10 5 bacteria/ml) of gram-positive pathogens Staphylococcus aureus and Enter ococcus faecalis and faecium as well as gram-negative pathogens Escherichia coli and Pseudomonas aeruginosa in accordance with the standard phenol-coefficient assay and other screening methodology for plant antimicrobial activity and incubated for 72 hrs. A 2 ml broth media was used as a positive control.
  • Formulation C comprised the toothpaste formulation described herein in Example 2.
  • Formulation D comprised at least 98% pure D- limonene (20%) and the remaining ingredients for Formulation C except for the calcium and magnesium (the remaining 0.5% being made up as water).
  • Formulation P was a placebo formulation, comprising: (a) 31.175% sorbitol; (b) 25.0% ZEODENT 113; (c) 17.44% water; (d) 12.5% glycerin natural kosher; (e) 6.25% Polysorbate 20; (f) 3.38% ZEODENT 165; (g) 1.25% flavoring 484; (h) 1.25% titanium dioxide; (i) 1.25% CEKOL 2000; (J) 0.313% sodium saccharin; and (k) 0.125% sodium benzoate.
  • Results of the assay at 24 hours are shown in Table 3. At 24 hours, each of the limone-containing toothpastes showed zones of inhibition for each of the pathogens tested, whereas the placebo showed no effect.
  • Example 7 Preparation of a Mouthwash Formulation Containing D-
  • a mouthwash formulation was manufactured by combining the following components: sorbitol 20.0%
  • PEG 61UltraPEG 300 15.0% polysorbate 20 5.0%
  • Example 8 3-Week Clinical Study of Limone-Containing Toothpastes in Treating Periodontal Disease.
  • a 3 week, double blind, clinical study was conducted to compare the effects of the toothpaste formulation described in Example 2 with a placebo dentifrice (i.e. without D-limonene or any other active ingredients) in treating periodontal disease.
  • Male and female adult subjects with a baseline Quigley-Hein Plaque Index scores of 1.5 or greater were entered into the study.
  • Each subject received a scale and root plane (S/RP) and a through periodontal screening upon entering the study.
  • the periodontal probing pocket depth (PD), bleeding on probing (BOP), plaque accumulation (PI), and gingival status (GI) were all measured at baseline and at 3 weeks. No professional detanl hygiene was delivered during the study period.
  • Assays for periodontal pathogens were also collected from the buccal and lingual surfaces of the first four molars. Specifically, assays for actinobacillus actinomycetemcomtuns , bacteroides forsythus, bacteroides gingivalis, bacterdides intermedins, streptococcus mutatis, porphyromonas gingivolis and provetella intermedia were conducted. Each of these bacteria are common periodontal pathogens
  • D-limonene additive in a fluoride-containing dentifrice exhibited distinctive plaque inhibitor effects and decreased bleeding on probing in chronic periodontal patients.
  • Example 9 6-Month Clinical Study of Limone-Containing Toothpastes in Treating Periodontal Disease.
  • a six month, double-blind clinical study was entered by 100 male and female adult subjects previously treated for chronic periodontis in order to assess the efficacy of a dentifrice containing D-limonene on supragingival plaque formation and chronic periodontal disease, compared to a placebo dentifrice.
  • plaque accumulated (PlI) and gingival status (GI) were assessed.
  • Probing Pocket Depth (PD) and Bleeding on Probing (BOP) were measured at baseline and week 28 using a Florida Probe. No professional dental hygiene was administered during the study period.
  • Table 4 summarizes the changes observed in PlI, GI, PD and BOP over the 28 week study period. Statistically insignificant changes are marked with an 'X'. There was no change to slight decreases in mean plaque score between baseline and week 28. There was also no change to slight decreases in mean gingival scores between baseline and week 28. PD and BOP did show some statistically significant reductions during the study period. Table 4: Gingival Assay Results for a Limonene-Containing Toothpaste Over a 28
  • PLAQ ACCUM (PlI) X X X X X GINGIVITIS STATUS (GI) X X X X PROBING POCKET DEPTH (PD) X X BLEEDING ON PROBING (BOP) X X

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Abstract

La présente invention concerne, dans plusieurs modes de réalisation, des compositions destinées à cicatriser une plaie et des méthodes de traitement de plaie. Les compositions de cicatrisation de plaie contiennent une composition à base de limonène et un support pour la composition à base de limonène. Les méthodes de traitement de plaie comprennent l'application d'une composition à base de limonène sur une plaie pour y inhiber la croissance de bactéries. Dans certains modes de réalisation, les méthodes comprennent l'application d'un biofilm sur la plaie, la composition à base de limonène étant contenue dans le biofilm.
PCT/US2009/065860 2008-11-26 2009-11-25 Méthodes de traitement et de cicatrisation de plaie à l'aide de compositions à base de limonène WO2010062933A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3051370A1 (fr) * 2016-05-18 2017-11-24 Mathieu Angelidis Composition pour le traitement d'une lesion cutanee
US20200338016A1 (en) * 2019-04-26 2020-10-29 Mark Edward Fenzl Combination broad-spectrum antibiotic preparations for drug-resistant pathogens

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3023144A (en) * 1959-08-17 1962-02-27 Mar Tay Inc Biocidal compositions for topical application
US20040076590A1 (en) * 2002-07-08 2004-04-22 Wilkins Joe S. Antibacterial toothpaste and mouthwash formulations
US20070275021A1 (en) * 1999-12-07 2007-11-29 Schott Ag New cosmetic, personal care, cleaning agent, and nutritional supplement compositions and methods of making and using same

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3023144A (en) * 1959-08-17 1962-02-27 Mar Tay Inc Biocidal compositions for topical application
US20070275021A1 (en) * 1999-12-07 2007-11-29 Schott Ag New cosmetic, personal care, cleaning agent, and nutritional supplement compositions and methods of making and using same
US20040076590A1 (en) * 2002-07-08 2004-04-22 Wilkins Joe S. Antibacterial toothpaste and mouthwash formulations

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3051370A1 (fr) * 2016-05-18 2017-11-24 Mathieu Angelidis Composition pour le traitement d'une lesion cutanee
US20200338016A1 (en) * 2019-04-26 2020-10-29 Mark Edward Fenzl Combination broad-spectrum antibiotic preparations for drug-resistant pathogens

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