WO2001068091A1 - Inhibition de champignons - Google Patents

Inhibition de champignons Download PDF

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Publication number
WO2001068091A1
WO2001068091A1 PCT/AU2001/000296 AU0100296W WO0168091A1 WO 2001068091 A1 WO2001068091 A1 WO 2001068091A1 AU 0100296 W AU0100296 W AU 0100296W WO 0168091 A1 WO0168091 A1 WO 0168091A1
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WO
WIPO (PCT)
Prior art keywords
fungi
composition
compounds
furanone
compound
Prior art date
Application number
PCT/AU2001/000296
Other languages
English (en)
Inventor
Gerd Pia Carola Holmstrom
Staffan Kjelleberg
Original Assignee
Unisearch Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Unisearch Limited filed Critical Unisearch Limited
Priority to AU2001240374A priority Critical patent/AU2001240374A1/en
Publication of WO2001068091A1 publication Critical patent/WO2001068091A1/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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents

Definitions

  • the present invention relates to compositions for use in inhibiting microorganisms, particularly fungi.
  • Fungi are a major problem in hospitals, on skin, in the dental area, for heart transplants, catheters, and other biomedical implants. Fungi are also present in domestic areas including bathrooms, toilets and kitchens and can also cause a disease hazard for these sources. Fungi are also a problem in many industrial situations. Unfortunately, only a few antifungal agents are available which have broad spectrum of activity. Accordingly, there is a need for more agents that are suitable to inhibit or kill fungi in many varied situations including domestic, veterinary and medical applications. The present inventors have now made the surprising finding that some selected furanone compounds are suitable as antifungal agents for a range of fungi.
  • the present invention consists in an antifungal composition, the composition comprising an effective amount of one or more compounds selected from the group consisting of:
  • the effective amount of the one or more furanone compounds does not substantially adversely effect the survival of an animal cell when exposed to the one or more furanone compounds.
  • the compound is preferably compound 26, 27, 30, 45, 57 or mixtures thereof. More preferably, the furanone compound is compound 30.
  • the concentration of the furanone compound in use is at least 100 ng/ml.
  • a range of about 100 ng/ml to 10 ⁇ g/ml has been found to be effective when used to inhibit the growth of fungi found to be implicated in animal or human disease.
  • the present invention consists in a method of inhibiting the growth of a fungi, the method comprising exposing the fungi to an effective amount of an antifungal agent according to the first aspect of the present invention for sufficient time such that the fungi is inhibited.
  • the fungi is killed or prevented from reproducing after exposure to the agent.
  • the effective amount of the one or more furanone compounds does not substantially adversely effect the survival of an animal cell when exposed to the one or more furanone compounds.
  • the present inventors have found that the method is particularly suitable for the fungi Aurebasidium pullulans, Penicillium digitatum, Cladosporium cladosporioides, Malesssezia furfur, Candida albicans
  • the method includes in vivo and in vitro treatment of fungi.
  • the agent may be formulated as a pharmaceutical agent for human and animal use, a topical agent for human and animal use, as an agricultural fungicide or agent for post-harvest food preservation, a disinfectant, an antiseptic, a mouth wash or rinse, a soap or cleaning agent.
  • the antifungal composition of the present invention has been shown to be active against Trichophyto mentagrophytes, the causative agent of tinea, and Candida albicans, which is involved in vaginal and oral infection, the antifungal composition has particular application in the treatment of these conditions.
  • the present invention consists in a method of treating an oral or vaginal Candida albicans infection in a subject, the method comprising administering to the subject in need of such treatment the anti-fungal composition of the present invention. It is preferred that the composition is administered topically.
  • the present invention consists in a method of treating tinea in a subject, the method comprising administering to the subject in need of such treatment the anti-fungal composition of the present invention. It is preferred that the composition is administered topically.
  • the antifungal composition of the present invention has also been shown to be active against two wood rotting fungi, Perennipora tephropora and Coniophora olivacea. Accordingly, the antifungal composition has particular application as a wood preservative.
  • antifungal compounds according to the present invention may be incorporated in different formulations for various uses. Specific product applications would include toilet cleaners, floor cleaners, bathroom and kitchen cleaners, fungicides for use in agriculture, upholstery cleaners and carpet cleaners, pool cleaning agents and the like.
  • the present invention consists in use of the agent according to the first aspect of the present invention for the inhibition of fungi.
  • Figure 1 Screening of 3 different compounds against growth of Candida albicans. The used furanone concentration was 5 ⁇ g/ml.
  • Figure 2. Growth of Candida albicans with compound 57 at different concentrations.
  • the screening method was based on using TLC aluminium sheets, silica gel 60 F 254 and 0.2 ⁇ m in thickness, and an agar overlay assay.
  • One percent of a dense fungi culture was inoculated to 0.6% malt extract agar (around 52°C) and mixed well. This solution was poured on top of the TLC plates (1 ml of malt extract agar + fungi was used for 5 cm 2 of the gel) containing the different furanone compounds at various concentrations.
  • the TLC plates with an agar overlay were incubated at the bottom of petri dishes in a 25°C incubator.
  • the inhibition zone of the different fungi target strains was measured after 5 days of growth. The result showed several important features.
  • furanones strongly inhibited growth at effective concentrations comparable (1 ⁇ g) and even lower concentrations (500-100 ng for three of the tested fungi strains) than that of standard commercial antibiotics.
  • synthetic furanone compounds or mixtures of compounds were often more active than those furanones which are produced naturally by the red alga Delisea pulchra.
  • Furanone compound 30 demonstrated the strongest activity against the different fungi strains tested.
  • the screening method was based on a filter pad assay.
  • the filter pads were dipped into furanone ethanol mix and thereafter allowed to dry and sterelized by Gamma Radiation treatment.
  • the sterile filters were placed into the centre of malt-agar petri dish and plugs of selected fungi were placed onto the filter pads. The diameter of the fungal growth was measured and the values are presented in table 5 and 6.
  • C. albicans were grown in Sabouraud dextrose media and M. furfur in a slightly modified Dixons media at 37°C.
  • One percent of overnight cultures (10 ⁇ cells/ml) were inoculated to 25 ml of growth media containing furanone compounds at the concentrations 10 ⁇ g-10 ng/ml for M. furfur and 10 ⁇ g/ml, 5 ⁇ g/ml and 1 ⁇ g/ml for C. albicans.
  • the growth was measured at 610nm for 140 hrs for M. furfur and 130 hrs for C. albicans.
  • furanones against M. furfur and C. albicans are presented in Figures 2 to 4.
  • Furanone compounds 26/27, 30 and 57 were found to be the most active compounds against C. albicans at a concentration of about 5 ⁇ g/ml.
  • Growth of M. furfur was shown to be inhibited at a concentration of about 100 ng/ml by using compound 30. This concentration is very low and well below concentrations of furanone compounds that inhibited mouse fibroblasts.
  • the synthetic furanone compounds were more active compared to naturally produced furanones.
  • Trichophyton mentagrophytes was screened against compound 30 ( Figure 4) using a Biomass assay.
  • the tested concentrations of furanone compound were 10, 5 and l ⁇ g/ml.
  • the screening method was based on liquid fungal culture filtered onto 0.45 ⁇ m sterile filters.
  • the growth medium for T. mentagrophytes was Glucose yeast peptone medium.
  • Three mm plugs of fungi were inoculated into the medium containing the furanone at various concentrations and incubated at 30° C for 48 hrs.
  • Five ml aliquot's of each treatment were filtered onto the sterile filters and dried in a 70° C oven. The filters were thereafter weighed and the dry weight of the fungal samples was recorded.
  • Table 5 and 6 show the effects of various furanone compounds or mixture thereof tested on Perennipora tephropora and Coniophora olivacea. Results within the table represent the diameter size of the fungal growth (in mm). Initial diameter of the fungal culture on the filter pad is 6mm. This figure has been subtracted from the growth values shown below. As can be seen from the Tables, furanone compounds 8, 26/27 and 64 were the most active against the two different fungi.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Epidemiology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne des compositions antifongiques et des méthodes de traitement d'infections fongiques. Les compositions de l'invention contiennent des furanones comme principe actif.
PCT/AU2001/000296 2000-03-16 2001-03-16 Inhibition de champignons WO2001068091A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001240374A AU2001240374A1 (en) 2000-03-16 2001-03-16 Inhibition of fungi

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AUPQ6290A AUPQ629000A0 (en) 2000-03-16 2000-03-16 Inhibition of fungi
AUPQ6290 2000-03-16

Publications (1)

Publication Number Publication Date
WO2001068091A1 true WO2001068091A1 (fr) 2001-09-20

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Family Applications (1)

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AU (1) AUPQ629000A0 (fr)
WO (1) WO2001068091A1 (fr)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002047681A1 (fr) * 2000-12-14 2002-06-20 Unisearch Limited Regulation de la virulence de bacteries
US6528472B2 (en) 2000-11-17 2003-03-04 S.C. Johnson & Son, Inc. Antimicrobial compositions containing quaternary ammonium compounds, silanes and other disinfectants with furanones
WO2008135746A2 (fr) * 2007-05-04 2008-11-13 Aquapharm Bio-Discovery Ltd Composés bioactifs naturels
US7642285B2 (en) 2005-02-04 2010-01-05 Wisconsin Alumni Research Foundation Compounds and methods for modulating communication and virulence in quorum sensing bacteria
US7825268B2 (en) 2003-12-23 2010-11-02 Henkel Ag & Co. Kgaa Alkoxylactones, alkoxylactams and alkoxythiolactams for controlling processes based on microbial interaction
US7902140B1 (en) 2003-10-21 2011-03-08 Bissell Homecare, Inc. Carpet cleaning with fungicide
US7910622B2 (en) 2007-03-19 2011-03-22 Wisconsin Alumni Research Foundation Modulation of bacterial quorum sensing with synthetic ligands
US8309117B2 (en) 2002-12-19 2012-11-13 Novartis, Ag Method for making medical devices having antimicrobial coatings thereon
US8519166B2 (en) * 2008-11-13 2013-08-27 Syracuse University System and method for controlling growth of microorganisms with brominated furanones
US8624063B2 (en) 2009-06-30 2014-01-07 Wisconsin Alumni Research Foundation Non-lactone carbocyclic and heterocyclic antagonists and agonists of bacterial quorum sensing
US10526278B2 (en) 2017-10-19 2020-01-07 Wisconsin Alumni Research Foundation Inhibitors of quorum sensing receptor LasR

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU708962B2 (en) * 1995-03-23 1999-08-19 Unisearch Limited Methods for microbial regulation
WO1999053915A1 (fr) * 1998-04-17 1999-10-28 Unisearch Limited Inhibition des bacteries gram positives
WO1999054323A1 (fr) * 1998-04-16 1999-10-28 Unisearch Limited Production de furanones

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU708962B2 (en) * 1995-03-23 1999-08-19 Unisearch Limited Methods for microbial regulation
WO1999054323A1 (fr) * 1998-04-16 1999-10-28 Unisearch Limited Production de furanones
WO1999053915A1 (fr) * 1998-04-17 1999-10-28 Unisearch Limited Inhibition des bacteries gram positives

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
DE NYS ET AL.: "Broad spectrum --- assays", BIOFOULING, vol. 8, no. 4, 1995, pages 259 - 271 *
FENICAL ET AL.: "Antibiotics and ... (florideophyceae)", PROC. INT. SEAWEED SYMP., vol. DATE 1977, 9, ISSUE DATE 1979, pages 387 - 400 *
HIYOSHIZO KOTSUKI ET AL.: "Efficient ... becherelides analogs", CHEMISTRY LETTERS, no. 7, 1983, pages 1007 - 1008 *
KJELLEBERG ET AL.: "Extracellular ... strain S14", J. BACTERIOL., vol. 180, no. 2, 1998, pages 201 - 209 *
MANEFIELD ET AL.: "Evidence that ... protein", MICROBIOLOGY, vol. 145, no. 2, 1999, READING, U.K., pages 283 - 291 *

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6528472B2 (en) 2000-11-17 2003-03-04 S.C. Johnson & Son, Inc. Antimicrobial compositions containing quaternary ammonium compounds, silanes and other disinfectants with furanones
WO2002047681A1 (fr) * 2000-12-14 2002-06-20 Unisearch Limited Regulation de la virulence de bacteries
US8637071B2 (en) 2002-12-19 2014-01-28 Novartis Ag Method for making medical devices having antimicrobial coatings thereon
US8309117B2 (en) 2002-12-19 2012-11-13 Novartis, Ag Method for making medical devices having antimicrobial coatings thereon
US7902140B1 (en) 2003-10-21 2011-03-08 Bissell Homecare, Inc. Carpet cleaning with fungicide
US7825268B2 (en) 2003-12-23 2010-11-02 Henkel Ag & Co. Kgaa Alkoxylactones, alkoxylactams and alkoxythiolactams for controlling processes based on microbial interaction
US7642285B2 (en) 2005-02-04 2010-01-05 Wisconsin Alumni Research Foundation Compounds and methods for modulating communication and virulence in quorum sensing bacteria
US8269024B2 (en) 2005-02-04 2012-09-18 Wisconsin Alumni Research Foundation Compounds and methods for modulating communication and virulence in quorum sensing bacteria
US9796694B2 (en) 2007-03-19 2017-10-24 Wisconsin Alumni Research Foundation Modulation of bacterial quorum sensing with synthetic ligands
US8815943B2 (en) 2007-03-19 2014-08-26 Wisconsin Alumni Research Foundation Modulation of bacterial quorum sensing with synthetic ligands
US7910622B2 (en) 2007-03-19 2011-03-22 Wisconsin Alumni Research Foundation Modulation of bacterial quorum sensing with synthetic ligands
WO2008135746A3 (fr) * 2007-05-04 2010-01-28 Aquapharm Bio-Discovery Ltd Composés bioactifs naturels
JP2010526047A (ja) * 2007-05-04 2010-07-29 アクアファーム・バイオ−ディスカバリー・リミテッド 天然生理活性化合物
WO2008135746A2 (fr) * 2007-05-04 2008-11-13 Aquapharm Bio-Discovery Ltd Composés bioactifs naturels
US8519166B2 (en) * 2008-11-13 2013-08-27 Syracuse University System and method for controlling growth of microorganisms with brominated furanones
US8624063B2 (en) 2009-06-30 2014-01-07 Wisconsin Alumni Research Foundation Non-lactone carbocyclic and heterocyclic antagonists and agonists of bacterial quorum sensing
US9758472B2 (en) 2009-06-30 2017-09-12 Wisconsin Alumni Research Foundation Non-lactone carbocyclic and heterocyclic antagonists and agonists of bacterial quorum sensing
US10807943B2 (en) 2009-06-30 2020-10-20 Wisconsin Alumni Research Foundation Non-lactone carbocyclic modulators of bacterial quorum sensing
US10526278B2 (en) 2017-10-19 2020-01-07 Wisconsin Alumni Research Foundation Inhibitors of quorum sensing receptor LasR

Also Published As

Publication number Publication date
AUPQ629000A0 (en) 2000-04-15

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