WO2003028762A1 - Nouvelles compositions bloquant la resistance antimicrobienne - Google Patents

Nouvelles compositions bloquant la resistance antimicrobienne Download PDF

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Publication number
WO2003028762A1
WO2003028762A1 PCT/US2001/030303 US0130303W WO03028762A1 WO 2003028762 A1 WO2003028762 A1 WO 2003028762A1 US 0130303 W US0130303 W US 0130303W WO 03028762 A1 WO03028762 A1 WO 03028762A1
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WO
WIPO (PCT)
Prior art keywords
methyl
composition
indazole
lff
triclosan
Prior art date
Application number
PCT/US2001/030303
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English (en)
Inventor
Hanuman B. Jampani
Lester A. Mitscher
Jerry L. Newman
Segagran P. Pillai
Original Assignee
Ethicon, Inc.
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Publication date
Application filed by Ethicon, Inc. filed Critical Ethicon, Inc.
Priority to PCT/US2001/030303 priority Critical patent/WO2003028762A1/fr
Publication of WO2003028762A1 publication Critical patent/WO2003028762A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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

Definitions

  • This invention is concerned with antimicrobial compositions that control or prevent resistance to antimicrobial effectiveness, more particularly to combinations of topical antimicrobial agents with agents that block development of intrinsic or acquired bacterial resistance.
  • the present invention relates to a topical antimicrobial composition
  • a topical antimicrobial composition comprising:
  • the topical antimicrobial is triclosan and the antimutagenic and/or antioxidant compound is selected from the group consisting of substituted and unsubstituted pyrithione-containing compounds; coumarins; pseudopeptides; indazoles; antioxida ts; flavanoids; isoflavanoids including isoflavenes, isoflavanes, isoflavanones and isoglabrene analogs; and mixtures thereof.
  • topical antimicrobial is intended to describe compounds used to inhibit or kill or otherwise prevent proliferation of microbes .
  • the topical antimicrobial agents are used to treat any type of surface, both mammalian and non-mammalian. In humans, these agents are widely used for treatment of the skin.
  • Suitable topical antimicrobial agents for use with this invention include nisin, bis-diguanides, chlorhexidine gluconate, chlorhexidine digluconate, chlorhexidine diacetate, chlorhexidine dihydrochloride, polyhexamethylene biguanide, benzalkonium chloride, benzethonium chloride, methylbenzethonium chloride, cetyl pyridinium chloride, triclosan, triclocarban, tribromosilane, amyltricresols, parachlorometaxylenol, phenol, silver, iodine, [nonylphenoxypoly (ethyleneoxy) ethanoliodine] poloxamer-iodine complex, undecoylium chloride, iodine complex, bisquaternary ammonium compounds, polymeric quaternary ammonium compounds, alcohols, cationic polypeptides, organometallic antiseptics, alkyl pyridinium salts,
  • a variety of simple alcohols may function in this regard, including but not limited to, ethanol, propanol, butanol, pentanol, 2-methyl-l-butanol, hexanol, 2- methyl-1-pentanol, 3-methyl-1- pentanol, 2-ethyl-l- butanol, 3 , 5 , 5-trimethyl-l-hexanol, heptanol, octanol, isooctyl alcohol, decanol, dodecanol, tridecanol, tetradecanol and the like.
  • antimutagenic compound or agent as used herein, is intended to describe compounds that lessen the extent of antimicrobial resistance. As will be shown hereinafter, not all antimutagenic agents are effective in inhibiting antimicrobial resistance when combined with topical antimicrobial agents.
  • antioxidant compound or agent is intended to describe oxygen scavenging compounds that prevent or lessen the degree of mutations in genetic material (e.g., DNA) , or prevent or lessen the degree of oxidation of poly-unsaturated fatty acids.
  • suitable antimutagenic and antioxidant agents are described both by chemical name and chemical structure. Due to the fact that chemical nomenclature for the same structure can vary and for the avoidance of doubt any discrepancy that may arise between a chemically named compound and the corresponding chemical structure shown, the chemical structure is intended to govern the description of the compound.
  • suitable antimutagenic and antioxidant compounds useful in this invention include the following compounds and analogs thereof: substituted and unsubstituted pyrithione-containing compounds; coumarins; pseudopeptides; indazoles; antioxidants; flavanoids; isoflavanoids including isoflavenes, isoflavanes, isoflavanones and isoglabrene analogs; and mixtures thereof.
  • pyrithione-containing compounds include substituted and unsubstituted pyrithione containing compounds such as monovalent or divalent metallic salts of pyrithione. Preferred are zinc, silver, and sodium salts of pyrithione.
  • Zinc Pyrithione Sodium Pyrithione examples include: 8- (2'2'-Dimet yl-l'H-pyran-7-yl) coumarin; [ (2 '2-Dimet yl-3- ⁇ - ydroxy-6-methylene) -1- ⁇ -cyclohexyl] -3 -methyl - pent-2-enyl-7-oxycoumarin; [ (2'2,6-Trimethyl-2-oxo-bicyclo)-2,2,l-heptyl]-l- ⁇ -3-methyl-pent-2- enyl-7-oxycoumarin; 7-Cyclohexylmethoxycoumarin; and Galbanic Acid.
  • Preferred coumarins are :
  • Suitable pseudopeptides include :
  • suitable indazoles include :
  • Isoniazid or 4-pyridinecarboxylic acid hydrazide l-Methyl-3-ethoxy-5-nitro-lH-Indazole; and l-Methyl-3 -ethoxy-5-amino-liT-Indazole .
  • Preferred indazoles are :
  • Isoniazid or 4-pyridinecarboxylic acid hydrazide Most preferred indazoles are :
  • Preferred isoglabrene analogs are:
  • Suitable antioxidants include trolox, reduced glutathione, butylated hydroxyanisole (BHA) , butylated hydroxytoluene (BHT) , (-) -Epigallocatechin Gallate
  • EGCG EGCG
  • GCG Gallocatechin Gallate
  • Preferred antioxidants are trolox, BHA, BHT, Gallocatechin, Gallate, Epigallocatechin, Epicatechin Gallate and Epicatechin.
  • antioxidants are reduced glutathione and Epigallocatechin Gallate.
  • the combination of topical antimicrobials and the antimutagenic and/or antioxidant compounds requires that the antimutagenic and/or antioxidant compounds be used in an effective amount.
  • the term effective amount refers to that amount of antimutagenic and/or antioxidant compound that when combined with the topical antimicrobial agent decreases the amount of antimicrobial resistant colonies present in the antimicrobial by at least 20%.
  • RC antimicrobial resistant colony
  • any effective amount of the antimutagenic and/or antiodoxidant compounds may be used and may widely vary, typical effective amounts when the compound is a pyrithione-containing compound will range from 0.1 to 25, preferably from 0.1 to 10, most preferably from 0.1 to 5 ⁇ g/ml on an individual basis.
  • Other antimutagenic and/or antioxidant compounds may be used in effective amounts ranging from 1 to 50, preferably from 1 to 25, most preferably from 1 to 10 mg/ml on an individual basis.
  • the relative ratio of topical antimicrobial to antimutagenic and/or antioxidant useful in this invention ranges generally from 1: 0.1-50, preferably from 1 : 0.1-10.0 , more preferably from 1 : 0.5-5.0, and most preferrably from 1:1, and vice versa based on weight.
  • the antimicrobial resistance blocking compositions of this invention may be used in a wide variety of applications .
  • Such applications include antimicrobial skin care products, antimicrobial wound dressings, antimicrobial therapeutic gels, anticancer compositions, antimicrobial gloves, antimicrobial skin preparations, antimicrobial drapes, antimicrobial scrubs, antimicrobial gels, antimicrobial lotions, antimicrobial contact lenses, antimicrobial artificial skin grafts, antimicrobial gene delivery systems, antimicrobial polypeptide and antimicrobial household products to name a few.
  • the antimicrobial resistance blocking compositions of this invention may be included with other skin treatment additives.
  • suitable additives include: skin protectants, anti-fungal compounds, surface active materials, cationic antimicrobials, natural oils, plant and marine derived bioactive and/or natural products, phospholipids, liposomes, cyclodextrins and metal oxides (e.g., zinc, copper).
  • the following bacterial strains were obtained from the American Type Culture Collection and were used in establishing antimicrobial and antibiotic sensitivity levels. Staphylococcus aureus ATCC 13709, Escherichia coli ATCC 9637, Salmonella choleraesuis ATCC 9184, Pseudomonas aeruginosa ATCC 27853, Klebsiella pne moniae ATCC 10031, and Candida albicans ATCC 10231 Escherichia coli AG100 was obtained through the courtesy of Professor Stuart Levy of Tufts University, Boston, MA.
  • Triclosan (Irgasan DP300) was obtained from CIBA Specialty Chemical Corp. To evaluate the degree of development of antimicrobial resistance, growth assays were performed using a selection of laboratory based bacteria in a 96 well ELISA plate format with varying concentrations of antiseptics and antibiotics in Oxoid Nutrient Broth No. 2 at 37°C. Readings were taken at 570 nm every 24 hours for 12 days using a Cambridge Technology, Inc., Plate Solver Ver. 4.00 and graphed as a function of growth vs. time. A second set of experiments used resistant strains of bacteria subcultured from survivors of the first experiment.
  • MIC and MBC assays were performed using various laboratory strains and multiple antibiotic resistant strains of bacteria collected from patients. The strains were grown in Oxoid Nutrient Broth No. 2 using a 96 well ELISA plate containing varying concentrations of test compounds with incubation for 15 hours at 37°C. After incubation the plates were examined using a Cambridge Technology, Inc., Plate Solver Ver. 4.00 at 570 nm. MIC-100 values were assigned from wells showing no absorbence. Following this, the media from wells showing no growth were streaked on Oxoid Nutrient Agar No. 2 plates and incubated for 15 hours at 37°C. MBC-100 values were assigned from plates showing no visible growth. Antibiograms (Kirby-Bauer) agar diffusion method for determination of zones of inhibition.
  • Sterile blank disks (6 mm in diameter) were impregnated with 5 ⁇ l on 10 ⁇ g/ml solutions of a variety of antimicrobials. Incubation was at 37°C for four days on Oxoid Nutrient No. 2 Agar plates. The plates were read on the second day for determinations of the diameter of the inhibition zones and on the fifth day for resistance development data. Resistance was measured by estimating the percentage of the zone of inhibition that was covered by resistant colonies or, in other experiments, by counting the number of individual colonies that developed in the otherwise clear zone of inhibition.
  • Escherichia coli AG100 strain was controlled for 13 days by doses of 2 ⁇ g/ml or more, but breakthrough to resistance was seen at concentrations between the MIC and MBC values in the form of perceptible growth in 9 days with 1 ⁇ g/ml and at 5 days with 0.5 and 0.25 ⁇ g/ml of triclosan.
  • Escherichia coli ATCC 9637 was controlled by doses of triclosan of 0.5 ⁇ g/ml and above but developed resistance in 5 days at 0.25 ⁇ g/ml.
  • E. coli AG 100 9 days l ⁇ g/ml 5 days 0.5 ⁇ g/ml* 5 days 0.25 ⁇ g/ml**
  • Table 1-1 Breakthrough levels to resistance by a series of laboratory microorganisms exposed to incremental doses of triclosan for 14 days, * indicates the growth did not reach the same level as control growth reached. ** indicates that growth reached the same level as the control growth reached but at the 11 th day of incubation. Generally the controls reached maximal growth levels by day 2.
  • triclosan resistant C. albicans ATCC 10231 was less resistant, showing growth in 5 days at 1 ⁇ g/ml, in 3 days at 0.5 ⁇ g/ml, and in 2 days at 0.25 ⁇ g/ml (Table 1-2) .
  • the C. albicans results suggest persistence rather than resistance.
  • Table 1-2 Breakthrough levels to resistance by triclosan resistant bacteria when subsequently exposed to incremental doses of triclosan for 14 days . (R . figures indicate the concentration of triclosan from which these resistant colonies were cultured . )
  • the MIC-100 and MBC-100 values for triclosan against these ATCC strains and E. coli AG 100 were determined by agar dilution methods and these are listed in Table 1-3 . The difference between these values is 2- 8 fold indicating that bacteriocidal doses of triclosan can easily be reached through the use of comparatively modest concentrations, except with Pseudomonas aeruginosa. and Salmonella choleraesuis which are intrinsically highly resistant at the outset. Repetition of these measurements using strains deliberately made triclosan resistant showed that E. coli and K. pneumoniae became highly resistant, but the C. albicans strain was still sensitive to triclosan. These results are in general agreement with those in Tables 1-1 and 1-2.
  • Table 1-3 A comparison of the MIC-100 and MBC-100 values (in ⁇ g/ml ) for triclosan na ⁇ ve and triclosan resistant strains of various bacteria .
  • Table 2-1 MIC-100 and MBC-100 levels for zinc pyrithione and sodium pyrithione against a variety of microorganisms .
  • zinc chloride, zinc sulfate, zinc acetate and zinc metal powder were inactive below 128 ⁇ g/ml .
  • Table 2-2 Effect of zinc and sodium pyrithione at 10 ⁇ g/ml on the zone sizes obtained for triclosan at the same concentration and on the development of resistant colonies in the resulting zones of inhibition. Cultures were incubated for 5 days at 37°c. The number of resistant colonies that developed are listed in the parentheses. Zinc acetate, zinc chloride, zinc sulfate and zinc metal powder were ineffective in producing zones or in reducing the number of resistant colonies that developed. Interestingly, however, breakthrough to resistance could be observed when all of the cultures, except P. aeruginosa and S. choleraesuis, were incubated for a long time (14 days) with zinc pyrithione (Table 2-3).
  • P. aeruginosa ATCC 27853 Not sensitive up to 32 ⁇ g/ml
  • Triclosan-resistant E. coli and K. pneumoniae were 1000-fold less sensitive to triclosan whereas triclosan-resistant C. albicans retained its sensitivity values (Table 1-3) .
  • Table 3A shows the effect of Galbanic acid analogs on the prevention of Triclosan (IRGASAN DP300) antimicrobial resistance development in E. coli ATCC 9637. In this case, 5 ⁇ l of lOmg/ml solution was embedded for each compound on a 6mm sterile disk.
  • the diameter of the zone of inhibition was measured in mm after incubation for 5 days at 37°C.
  • the number of resistant colonies within the zone of inhibition was recorded down as RC values .
  • Table 3B shows the effect of coumarin analogs on the prevention of Triclosan (IRGASAN DP300) antimicrobial resistance development in E. coli ATCC 9637.
  • IRGASAN DP300 Triclosan
  • Table 3B shows the effect of coumarin analogs on the prevention of Triclosan (IRGASAN DP300) antimicrobial resistance development in E. coli ATCC 9637.
  • 5 ⁇ l of lOmg/ml solution was embedded for each compound on a 6mm sterile disk.
  • the diameter of the zone of inhibition was measured in mm after incubation for 5 days at 37°C.
  • the number of resistant colonies within the zone of inhibition was recorded down as RC values .
  • Galbanic Acid provided compositions that were effective to reduce antimicrobial blocking resistance by at least 20 percent.
  • This example summaries the effectiveness of Indazole analogs on the prevention of Triclosan (IRGASAN DP300) antimicrobial resistance development in E. coli ATCC 9637.
  • IRGASAN DP300 Triclosan
  • 5 ⁇ l of lOmg/ml solution was embedded for each compound on a 6 mm sterile disk.
  • the diameter of the zone of inhibition was measured in mm after incubation for 5 days at 37°C.
  • the number of resistant colonies within the zone of inhibition was recorded down as RC values .
  • Benzydamine l-Methyl-3- [ (dimethylamino) propyloxy-lff-indazole ; Isoniazid or 4-pyridinecarboxylic acid hydrazide; l-methyl-3 -ethoxy-5-nitro-lff-Indazole ; and 1 -methyl -3 -ethoxy-5 -amino- lff-indazole provided compositions that were effective to reduce antimicrobial blocking resistance by at least 20 percent .
  • 5-Methoxy-6- [ (2-hyroxymethyl-5-mesyloxy) -2-phenyloxy] aceto-2,2- dimethylbenzo-lff-benzopyran; and 2-hydroxy-4-mesyloxybenzylacohol provided compositions that were effective to reduce antimicrobial blocking resistance by at least 20 percent.

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Abstract

L'invention concerne des compositions antimicrobiennes qui régulent ou empêchent la résistance à l'efficacité antimicrobienne, en particulier à des combinaisons d'agents antimicrobiens topiques avec des agents antimutagènes et antioxydants qui bloquent la résistance bactérienne intrinsèque ou acquise.
PCT/US2001/030303 2001-09-28 2001-09-28 Nouvelles compositions bloquant la resistance antimicrobienne WO2003028762A1 (fr)

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2402880A (en) * 2003-06-20 2004-12-22 Johnson & Johnson Medical Ltd Antimicrobial silver complexes
WO2004112805A1 (fr) * 2003-06-20 2004-12-29 Johnson & Johnson Medical Limited Antimicrobien a l'argent
EP1938841A2 (fr) * 2006-12-20 2008-07-02 National Institute of Immunology Composition synergétique pour moduler l'activité d'analogues de substrat pour des enzymes dépendantes du NAD+, NADP+, NADH+ ou NADPH et procédé correspondant
US7939488B2 (en) 2008-08-26 2011-05-10 The Clorox Company Natural disinfecting cleaners
US8252841B2 (en) 2007-10-19 2012-08-28 The Board Of Regents Of The University Of Texas System Methods of inhibiting bacterial virulence and compounds relating thereto
CN103142990A (zh) * 2013-03-14 2013-06-12 山东信得科技股份有限公司 一种治疗畜禽细菌性疾病的药物及其制备方法
WO2014014490A1 (fr) * 2012-07-18 2014-01-23 Bedoukian Research, Inc. Agents antimicrobiens
WO2014170683A1 (fr) * 2013-04-17 2014-10-23 Blueberry Therapeutics Limited Compositions et procédés pour lutter contre des bactéries résistantes à un antibactérien
WO2016133479A1 (fr) * 2015-02-19 2016-08-25 Yeditepe Universitesi Formulation de revêtement pour la stérilisation de semences et de surfaces
WO2017074285A1 (fr) * 2015-10-26 2017-05-04 Yeditepe Universitesi Matériau de revêtement de surface antimicrobien
JP2020530853A (ja) * 2017-08-14 2020-10-29 プソマーゲン， インコーポレイテッドＰｓｏｍａｇｅｎ， Ｉｎｃ． トリメチルアミン及び／又はトリメチルアミン−ｎ−オキシドに関連する標的薬

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JPS61238719A (ja) * 1985-04-17 1986-10-24 Shiseido Co Ltd 頭髪化粧料
JPS61263910A (ja) * 1985-05-20 1986-11-21 Shiseido Co Ltd 頭髪化粧料
EP0680745A2 (fr) * 1994-05-05 1995-11-08 L'oreal Utilisation de composés antifongiques et de composés antibactériens halogénés pour diminuer la chute des cheveux
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EP0843002A2 (fr) * 1996-11-15 1998-05-20 Kao Corporation Composition détergente
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JPS61238719A (ja) * 1985-04-17 1986-10-24 Shiseido Co Ltd 頭髪化粧料
JPS61263910A (ja) * 1985-05-20 1986-11-21 Shiseido Co Ltd 頭髪化粧料
EP0680745A2 (fr) * 1994-05-05 1995-11-08 L'oreal Utilisation de composés antifongiques et de composés antibactériens halogénés pour diminuer la chute des cheveux
WO1998002137A1 (fr) * 1996-07-12 1998-01-22 Indústria e Comércio de Cosméticos Natura Ltda. Composition sous forme de gel regulateur de la seborrhee epidermique
EP0843002A2 (fr) * 1996-11-15 1998-05-20 Kao Corporation Composition détergente
WO1999027792A1 (fr) * 1997-11-27 1999-06-10 Novapharm Research (Australia) Pty. Ltd. Produit biocide ameliore et etoffe biocide a base de ce produit

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DATABASE WPI Week 198701, Derwent World Patents Index; AN 1987-003711, XP002199663, SHISEIDO: "Safe hair cosmetic for dandruff prevention-containing the extract of luffa cylindrica and e.g. zinc pyrithione, chlorhexidine gluconate etc." *
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Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2402880A (en) * 2003-06-20 2004-12-22 Johnson & Johnson Medical Ltd Antimicrobial silver complexes
WO2004112805A1 (fr) * 2003-06-20 2004-12-29 Johnson & Johnson Medical Limited Antimicrobien a l'argent
GB2402880B (en) * 2003-06-20 2008-01-23 Johnson & Johnson Medical Ltd Antimicrobial compositions comprising silver
EP1938841A2 (fr) * 2006-12-20 2008-07-02 National Institute of Immunology Composition synergétique pour moduler l'activité d'analogues de substrat pour des enzymes dépendantes du NAD+, NADP+, NADH+ ou NADPH et procédé correspondant
EP1938841A3 (fr) * 2006-12-20 2008-10-08 National Institute of Immunology Composition synergétique pour moduler l'activité d'analogues de substrat pour des enzymes dépendantes du NAD+, NADP+, NADH+ ou NADPH et procédé correspondant
US8252841B2 (en) 2007-10-19 2012-08-28 The Board Of Regents Of The University Of Texas System Methods of inhibiting bacterial virulence and compounds relating thereto
US7939488B2 (en) 2008-08-26 2011-05-10 The Clorox Company Natural disinfecting cleaners
JP2015526418A (ja) * 2012-07-18 2015-09-10 ベドウキアン リサーチ， インコーポレイテッド 抗微生物剤
WO2014014490A1 (fr) * 2012-07-18 2014-01-23 Bedoukian Research, Inc. Agents antimicrobiens
CN103142990A (zh) * 2013-03-14 2013-06-12 山东信得科技股份有限公司 一种治疗畜禽细菌性疾病的药物及其制备方法
JP2018076338A (ja) * 2013-04-17 2018-05-17 ブルーベリー セラピューティクス リミテッド 抗菌薬耐性菌に対処するための組成物及び方法
CN105377250A (zh) * 2013-04-17 2016-03-02 蓝莓疗法有限公司 用于对抗抗菌剂抗性细菌的组合物和方法
US20160089393A1 (en) * 2013-04-17 2016-03-31 Blueberry Therapeutics Limited Composition and methods for combating antibacterial resistant bacteria
WO2014170683A1 (fr) * 2013-04-17 2014-10-23 Blueberry Therapeutics Limited Compositions et procédés pour lutter contre des bactéries résistantes à un antibactérien
WO2016133479A1 (fr) * 2015-02-19 2016-08-25 Yeditepe Universitesi Formulation de revêtement pour la stérilisation de semences et de surfaces
US20170135339A1 (en) * 2015-02-19 2017-05-18 Yeditepe Universitesi Coating formulation for seed and surface sterilization
JP2017537872A (ja) * 2015-02-19 2017-12-21 イェディテペ・ウニヴェルシテシＹｅｄｉｔｅｐｅ Ｕｎｉｖｅｒｓｉｔｅｓｉ 種子および表面滅菌のためのコーティング製剤
WO2017074285A1 (fr) * 2015-10-26 2017-05-04 Yeditepe Universitesi Matériau de revêtement de surface antimicrobien
US20190075791A1 (en) * 2015-10-26 2019-03-14 Yeditepe Universitesi Antimicrobial surface coating material
US11154056B2 (en) 2015-10-26 2021-10-26 Yeditepe Universitesi Antimicrobial surface coating material
JP2020530853A (ja) * 2017-08-14 2020-10-29 プソマーゲン， インコーポレイテッドＰｓｏｍａｇｅｎ， Ｉｎｃ． トリメチルアミン及び／又はトリメチルアミン−ｎ−オキシドに関連する標的薬

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