EP1143995A1 - Composition antipelliculaire comprenant un polypeptide fongicide - Google Patents

Composition antipelliculaire comprenant un polypeptide fongicide

Info

Publication number
EP1143995A1
EP1143995A1 EP99972925A EP99972925A EP1143995A1 EP 1143995 A1 EP1143995 A1 EP 1143995A1 EP 99972925 A EP99972925 A EP 99972925A EP 99972925 A EP99972925 A EP 99972925A EP 1143995 A1 EP1143995 A1 EP 1143995A1
Authority
EP
European Patent Office
Prior art keywords
amino acid
polypeptide
antifungal polypeptide
substituted
composition according
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP99972925A
Other languages
German (de)
English (en)
Inventor
Jesper Vind
Niels Henrik Sorensen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novozymes AS
Original Assignee
Novozymes AS
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 Novozymes AS filed Critical Novozymes AS
Publication of EP1143995A1 publication Critical patent/EP1143995A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/006—Antidandruff preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • 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
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/37—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from fungi
    • C07K14/38—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from fungi from Aspergillus
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/70—Biological properties of the composition as a whole

Definitions

  • the present invention relates to an anti -dandruff composition comprising an antifungal polypeptide, to the use of an antifungal polypeptide for the treatment or prophylaxis of dandruff, to a method for the treatment or prophylaxis of dandruff, and to the use of an antifungal polypeptide for the preparation of a composition for the treatment or prophylaxis of dandruff.
  • Dandruff results from a scalp malfunction but is not considered as being a skin disease and, accordingly, dandruff should be distinguished from the diseases that may mimic it in their early stages. Thus, although dandruff is only of cosmetic concern, a large research effort has been devoted to the field of treating this condition.
  • dandruff is mainly caused by the yeast Pi tyrosporum ovale and, consequently, substances which inhibit the growth of P. ovale might prove useful in the treatment or prophylaxis of dandruff.
  • Active substances which traditionally have been used for treating dandruff include for example various coal tar preparations, salicylic acid, selenium sulphide and zinc pyrithione.
  • the present invention relates to an anti-dandruff composition suitable for application to the hair or scalp of a human, comprising an effective amount of an antifungal polypeptide comprising the amino acid sequence shown in Fig. 1, or a variant thereof,
  • said variant being a polypeptide which
  • the present invention relates to the use of an antifungal polypeptide as defined above for the treatment or prophylaxis of dandruff.
  • the present invention relates to a method for the treatment or prophylaxis of dandruff, said method comprising contacting hair with an effective amount of an antifungal polypeptide as defined above.
  • the present invention also relates to the use of an antifungal polypeptide as defined above for the preparation of a composition for the treatment or prophylaxis of dandruff.
  • Figure 1 shows the full amino acid sequence of the antifungal polypeptide.
  • Figure 2 is a schematic representation of the microtiter plates in which the yeast P. ovale was grown, cf. Example 1.
  • the antifungal polypeptide and variants thereof In the present context, the three-letter code of the amino acids has been used in its conventional meaning. Unless indicated explicitly, the amino acids mentioned herein are L- amino acids.
  • antifungal polypeptide as used herein is intended to comprise the linear as well as the active folded structures of the polypeptide, and may, where appropriate, be used interchangeably with the term “antifungal protein” .
  • variant as used in connection with the antifungal polypeptide is intended to indicate a polypeptide which is derived from the polypeptide having the amino acid sequence shown in Fig. 1, or a naturally occurring variant.
  • the variant differs from the native antifungal polypeptide by one or more amino acid residues, which may have been added or deleted from either or both of the N-terminal or C-terminal end of the polypeptide, inserted or deleted at one or more sites within the amino acid sequence of the polypeptide, or substituted with one or more amino acid residues within, or at either or both ends of the amino acid sequence of the polypeptide.
  • the variant of the invention has one or both of the characteristic properties I) and II) mentioned above.
  • Property I i.e. the reactivity of the variant of the invention with an antibody raised against or reactive with at least one epitope of the polypeptide having the amino acid sequence shown in Fig. 1 below, may be determined using an antibody preparation produced as described under the heading " Production of antibodies against the AFPP" in the Materials and Methods section below.
  • the antibody reactivity may be determined using assays known in the art, examples of which are Western Blotting or radial immunodiffusion assay, e.g. as described by Hudson et al . , 1989.
  • the homology referred to above of the AFPP is determined as the degree of identity between two protein sequences indicating a derivation of the first sequence from the second.
  • the homology may suitably be determined by means of computer programs known in the art such as GAP provided in the GCG program package
  • Gap with the following settings for polypeptide sequence comparison: Gap creation penalty of 3.0 and Gap extension o penalty of 0.1, the mature part of a polypeptide encoded by an analogous DNA sequence of the invention exhibits a degree of identity preferably of at least about 60%, such as at least about 70%, at least about 80%, at least about 90%, at least about 95%, more preferably at least about 97%, and most s preferably at least about 99% with the mature part of the amino acid sequence shown in figure 1.
  • the AFPP comprises the amino acid sequences of figure 1; or allelic variants thereof; or fragments thereof 0 that has AFPP activity.
  • a fragment of AFPP is a polypeptide which have one or more amino acids seleted from the amino and/or carboxyl terminus of this amino acid sequence.
  • An allelic variant denotes any of two 5 or more alternative forms of a gene occupying the same chromosomal locus. Allelic variation arises naturally through mutation, and may result in polymorphism within populations. Gene mutations can be silent (no change in the encoded polypeptide) or may encode polypeptides having altered amino 0 acid sequences.
  • An allelic variant of a polypeptide is a polypeptide encoded by an allelic variant of a gene.
  • amino acid sequences of homologous AFPP may differ from the amino acid sequence of figure 1 by an insertion or deletion of one or more amino acid residues and/or the substitution of one or more amino acid residues by different amino acid residues.
  • amino acid changes are of a minor nature, that is conservative amino acid substitutions that do not significantly affect the folding and/or activity of the protein; small deletions, typically of one to about 30 amino acids; small amino- or carboxyl-terminal extensions, such as an amino- terminal methionine residue; a small linker peptide of up to about 20-25 residues; or a small extension that facilitates purification by changing net charge or another function, such as a poly-histidine tract, an antigenic epitope or a binding domain .
  • an effective amount when used herein is intended to mean an amount of the antifungal polypeptide comprising the amino acid sequence shown in Fig. 1, or a variant thereof, which is sufficient to combat (thereby removing or at least arresting) scaling due to dandruff.
  • the polypeptide to be used according to the invention is derived from a microorganism. While it is contemplated that the antifungal polypeptide or a variant thereof may be produced by other microorganisms such as bacteria, protozoae and algae, the polypeptide is normally derived from a fungus, in particular a fungus of the genus Aspergillus .
  • the antifungal polypeptide having the amino acid sequence shown in Fig. 1 has been found in several strains of the fungal species A . - giganteus, an example of which is the A . giganteus strain deposited with the Centraallbureau voor Schimmelcultures (CBS) under the deposition number CBS 526.65.
  • CBS Centraallbureau voor Schimmelcultures
  • antifungal polypeptide, or variants thereof, suitable for the use according to the invention are expected to be derivable from other fungal species, especially other Aspergillus species such as A . pallidus , A . clavatus, A . longivesica, A . rhizopodus and A . clavatonanicus, because of the close relationship which exists between these species and A . giganteus .
  • the variant of the antifungal polypeptide may be a naturally derived variant, i.e. a polypeptide isolated from any of the fungal species listed above, or may be a synthetically produced variant constructed on the basis of the knowledge of the amino acid sequence of the antifungal polypeptide .
  • variants of the antifungal polypeptide may also be useful for the purposes of the present invention. Therefore, it is contemplated that interesting variants of the polypeptide shown in Fig. 1, which will also be useful in the treatment or prophylaxis of dandruff, may be identified on the basis of an analysis of the conformational structure and the active site of the antifungal polypeptide shown in Fig. 1 using techniques known in the art, examples of which are NMR (e.g. as described in Protein Engineering, Editors Oxender, D.L. and Fox, C.F., Alan R. Liss, Inc. New York (1987), X-ray diffraction, computer modelling etc. When one or more interesting modifications of the amino acid sequence of the antifungal polypeptide have been identified, the corresponding variants may be prepared by suitably modifying a nucleotide sequence encoding the antifungal polypeptide.
  • Asn-4 has been replaced with Pro
  • Ala-24 has been replaced with Gly
  • Lys-32 has been replaced with Arg
  • Phe-42 has been replaced with Leu
  • Tyr-50 has been replaced with His.
  • an antifungal polypeptide which comprises, and preferably consists of, the amino acid sequence shown in Fig. 1, in which Pro in position 4 has been substituted with Asn, Gly in position 24 has been substituted with Ala, Arg in position 32 has been substituted with Lys, Leu in position 42 has been substituted with Phe, and/or His in position 50 has been substituted with Tyr.
  • WO 94/01459 Another interesting variant has been disclosed in WO 94/01459.
  • the amino acid sequence disclosed in WO 94/01459 differs from the amino acid sequence shown in Fig. 1 in the following way: Pro-4 has been replaced with Asp, Gly-24 has been replaced with Ala, Arg-32 has been replaced with Val , Leu-42 has been replaced with Phe and His-50 has been replaced with Tyr.
  • an antifungal polypeptide which comprises, and preferably consists of, the amino acid sequence shown in Fig. 1, in which Pro in position 4 has been substituted with Asp, Gly in position 24 has been substituted with Ala, Arg in position 32 has been substituted with Val, Leu in position 42 has been substituted with Phe, and/or His in position 50 has been substituted with Tyr.
  • the antifungal polypeptide shown in Fig. 1, as well as variants thereof, may be prepared by methods known in the art. A detailed description of the preparation of the polypeptide shown in Fig. 1 is given in WO 94/01459
  • compositions described herein will, for the sake of simplicity, generally be referred to as “shampoo compositions" it will be understood by persons skilled in the art that the antifungal polypeptide may also be incorporated into any other composition suitable for application to the scalp or hair. Therefore, such non-shampoo compositions comprising the antifungal polypeptide are also within the scope of the present invention. Examples of such other compositions are solutions, suspensions, emulsions, gels, foams, creams, etc. Thus, while a shampoo is the presently preferred composition for applying the antifungal polypeptide of the invention, it is also contemplated that the antifungal polypeptide may be applied by other means, e.g. formulated into a hair gel or mousse, a hair tonic, a hair spray, a hair conditioner, a hair dressing, etc.
  • Shampoo compositions may be adapted to oily, dry or normal hair and may be prepared in a manner well-known to the person skilled in the art, e.g. such as described in ,x Woodruff's ingredients & formulary handbook", 1997, Miller Freeman.
  • a hair gel or mousse, a hair tonic, a hair spray, a hair conditioner, etc. may also be prepared using ingredients and methods known in the art for the preparation of such compositions adapted to be applied to the hair or scalp. It will be clear to persons skilled in the art, however, that anti-dandruff compositions according to the invention should not be produced using ingredients or methods (e.g. excessively high temperatures) that would tend to inactivate the antifungal polypeptide .
  • the active ingredient i.e. the antifungal polylpeptide comprising the amino acid sequence shown in Fig. 1, or a variant thereof, is employed in the shampoo composition in an amount which is effective for treatment or prophylaxis of dandruff .
  • the shampoo composition of the present invention will typically contain the antifungal polypeptide in an amount from about 10 "7 to about 10 percent by weight calculated on the total weight of the shampoo composition.
  • the amount of antifungal polypeptide is in the range from about 5x10 "6 to about 5% such as in any of the below sub-ranges: about 5xl0 "6 to about 0.5%; about 5xl0 "6 to about 0.1%; about 5xl0 "6 to about 10 "5 %; about 10 "5 to about 10 " %; about 10 "4 to about 10 ⁇ 3 %; about 10 "3 to about 0.01%; about 0.01 to about 0.1%; about 0.1% to about 1.0%; and about 1.0% to about 5.0%.
  • Shampoo compositions according to the present invention may contain one or more surfactants, which are employed principally as cleansing agent. Selection of suitable surfactants is a matter of common general knowledge for the person skilled in the art. Usually anionic surfactants are employed in shampoo compositions. Examples of such anionic surfactants are alkali metal, ammonium or hydroxyalkylamine salts of alkyl sulphates, alkyl benzene sulphonates, alkyl sulphones, ⁇ -alkenyl sulphonates, polyoxyethylenealkylphenyl sulphonates and polyoxyethylenealkylphenyl sulphates . Mixtures of surfactants may also be used.
  • a specific example of a suitable surfactant which may be included in the shampoo composition according to the invention is sodium laureth sulphate, which has the formula CH 3 (CH 2 ) 10 CH 2 (OCH 2 CH 2 ) n OS0 3 Na, wherein n represents a number having an average value of from 1 to 4.
  • Cocoyl sarcosine is the coconut oil fatty acid amide of sarcosine (N-methylglycine) and coconut fatty acid is a mixture of myristic acid, lauric acid, palmitic acid and stearic acid.
  • Suitable surfactants which may be incorporated in the shampoo composition of the present invention include sodium C 14 , C 15 and C 16 olefin sulphonates, sodium lauryl sulphate, cocamidopropylamine oxide, lauramido diethanolamine (lauramido DEA) , cocamidopropyl betaine, disodium oleamido MIPA sulfosuccinate, disodium cocamido MIPA sulfosuccinate, disodium laureth sulfosuccinate, cocoaamphocarboxy-glycinate and disodium MEA sulfosuccinate.
  • surfactants which may be incorporated in the composition of the present invention are sugar surfactants.
  • examples of surfactants in the form of sugar surfactants include (a) alkyl- and/or alkenyloligoglycosides and/or (b) fatty acid-N-alkylpolyhydroxyalkylamides .
  • the alkyl- and/or alkenyloligoglycoside (a) may have the formula (I) :
  • R 1 a C 4 _ 22 alkyl and/or alkenyl group
  • G a sugar residue with 5 or 6 carbon atoms
  • p 1-10.
  • the fatty acid-N-alkylpolyhydroxyalkylamide (b) may have the formula:
  • the weight ratio (I): (II) is preferably 1:99-99:1.
  • fatty acid-N-alkyl polyhydroxyalkyl amides are also included.
  • sugar surfactants of: saccharose esters, sorbitan esters and/or polysorbates .
  • R 2 and R 3 are independently C 12
  • sugar surfactant is a polyglycerin fatty acid ester polyoxyalkylene ether R 1 R 2 R 3 N + -CH (Y) -CH 2 -0-CH 2 -
  • Sugar surfactants can also be selected from alkyl oligoglycosides of formula (I) and carboxylic acid N- polyhydroxyalkylamides of formula (II) :
  • R 1 optionally hydroxylated C 1 _ 8 alkyl
  • G a sugar residue with 5 or 6 carbon atoms
  • p 1-10
  • R 2 CO aliphatic acyl
  • R" H, alkyl or C x _ 8 hydroxyalkyl
  • Z C 3 12 polyhydroxyalkyl containing 3-10 OH groups.
  • the shampoo composition of the present invention may also contain foaming agents such as fatty acid mono- and di- alkanolamides such as, for example, cocamide MEA (a mixture of coconut acid monoethanolamides) , cocamide DEA (a mixture of coconut acid diethanolamides) , oleamide DEA and oleamide DEA.
  • the shampoo composition of the present invention may also contain one or more viscosity enhancing agents in order to confer the shampoo a suitable "thickness" . Examples of such viscosity enhancing agents are Carbopol 1342 and cellulose derivatives such as hydroxypropyl methylcellulose, hydroxyethyl cellulose, carboxy ⁇ nethyl cellulose, and the like. Addition of small amounts (usually from 0.2 to 5.0% by weight) of NaCl may also be used in order to control the viscosity of the final shampoo composition.
  • compositions of the present invention may also include one or more preservatives such as tetrasodium EDTA (the tetrasodium salt of ethylenediamine tetraacetic acid) , quaternium-15 (1- (3 -chloroallyl) -3,5, 7-triaza-l-azonia- adamantane chloride) , Kathon CG biocide (a mixture of 5-chloro- 2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3- one) , paraben, methylparaben, benzyl alcohol, and the like.
  • preservatives such as tetrasodium EDTA (the tetrasodium salt of ethylenediamine tetraacetic acid) , quaternium-15 (1- (3 -chloroallyl) -3,5, 7-triaza-l-azonia- adamantane chloride) , Kathon CG biocid
  • compositions of the present invention may also contain other accessory agents such as perfume, colouring agents, opacifiers, conditioning agents such as polyquaternium-7 (which is the polymeric quaternary ammonium salt of acrylamide and dimethyl diallyl ammonium chloride) , pearlizing agents such as ethylene glycol distearate and ethylene glycol monostearate, antioxidants such as butylated hydroxytoluene (BHT) and butylated hydroxyanisole (BHA) , and/or pH adjusting agents such as, for example, citric acid, phosphoric acid, sodium hydroxide, and the like.
  • conditioning agents such as polyquaternium-7 (which is the polymeric quaternary ammonium salt of acrylamide and dimethyl diallyl ammonium chloride)
  • pearlizing agents such as ethylene glycol distearate and ethylene glycol monostearate
  • antioxidants such as butylated hydroxytoluene (BHT) and butylated hydroxyanisole (BHA)
  • compositions of the present may also contain one or more therapeutically active components in addition to the antifungal polypeptide.
  • therapeutically active components are piroctone (an antiseborrheic agent whose chemical name is l-hydroxy-4 -methyl -6- (2 , 4 , 4-trimethylpentyl) - 2 (1H) -pyridinone) , ketoconazole and elubiol .
  • the components of the shampoo composition are employed in conventional amounts, for example:
  • AFPP antifungal polypeptide
  • Oat (Avena sativa) protein (Microat E, Tri-K) 1.00%
  • the pH of the composition is adjusted with NaOH/citric acid.
  • the pH of the composition is adjusted with citric acid.
  • Crotein Q 0.25 Conditioning (quaternised ingredient collagen AFPP 5x10 -1.0 Antifungal polypeptide
  • the pH of the composition is adjusted to 6.0-6.5 with citric acid/NaOH.
  • Shampoo Composition XV is adjusted to 6.0-6.5 with citric acid/NaOH.
  • Coco amido propyl betaine Coco amido propyl betaine .
  • antidandruff shampoo compositions wherein the antifungal polypeptide of the present invention may be incorporated and optionally substituted with the antidandruff substance present in the composition are disclosed in the following: WO 99/13830 disclosing shampoo compositions comprising: a) an effective amount of a triazole, b) a detersive surfactant, and c) a carrier;
  • WO 99/39683 disclosing shampoo compositions comprising: a) from about 7% to about 30% by weight of a detersive surfactant selected from the group consisting of anionic surfactant, amphoteric surfactant, and a mixture thereof, b) from about 0.1 % to about 10 % by weight of an antimicrobial agent, c) from about 0.5 % to about 10% by weight of a suspending agent, d) from about 0.01 % to about 1.0 % by weight of a cationic guar polymer having a charge density of from about 0.1 to about 3 meq/mg, e) a cool-feeling agent selected from the group consisting of borneol , camphor, cineol, methane, glycosil-mono- mentyl-oacetate, menthol, 3-1-menthoxypropane, peppermint, speamint, and mixtures thereof, and f) from about 40% to about 92% by weight of water, wherein at least about 50%
  • WO 97/39096 disclosing a shampoo composition
  • a shampoo composition comprising an antimicrobial compound selected from certain 1-hydroxy- 6- substituted pyridine-2 -one and 2-thione compounds, and a shampoo surfactant, in which the pH of the hair treatment composition is adjusted to at least 7 ;
  • WO 97/26854 disclosing a shampoo composition
  • a detersive surfactant selected from the group consisting of anionic surfactant, amphoteric surfactant, zwitterionic surfactant, and compositions thereof, b) from about 0.1% to about 10% by weight of an antimicrobial agent, c) from about 0.5% to about 10% by weight of a suspending agent, d) from about 0.01% to about 1.0% by weight of a cationic guar polymer having a charge density of from about 0.01 meq/mg to about 3 meq/mg, and e) from about 40% to about 92% be weight of water, wherein at least 50% be weight of the cationic guar polymer is in coacervate form, said coacervate comprising detersive surfactant and cationic uar polymer;
  • WO 97/47275 disclosing an anti-dandruff agent containing clotrimazol as the active agent, especially rinse-off products like shampoos, medicated shampoos or rinses;
  • an anti-dandruff shampoo composition comprising: a) from about 5% to about 29.5% by weight of anionic surfactant selected from the group consisting of alkyl sulfates and alkyl ehtoxylated sulfates, acids thereof, and mixtures thereof, b) from about 0.5% to about 5% by weight of N-acylamino acid anionic surfactant and salts thereof, c) from about 0.1% to about 10% by weight of particulate anti-dandruff agent, d) from about 0.5% to about 10% by weight of crystalline suspending agent for said anti -dandruff active, e) from about 40% to about 89% by weight of water, wherein the total detersive surfactant concentration in said composition is from about 10% to about 30%, the weight ratio of components b) : component a) is at least about 1:20, and said composition is substantially free of betaine surfactants and alkanol amide foam boosters;
  • WO 95/17880 disclosing a shampoo composition
  • a) from about 5% to about 40% by weight surfactant system comprising: (i) from 80% to about 99% by weight of the surfactant system, anionic surfactants which are alkyl ethoxylated sulfates and alkyl sulfates in a ratio between about 1:1 and 1:0, and (ii) from about 1% to 20% by weight of the surfactant system, polyhydroxy fatty acid amide surfactants, b) from about 0.05% to about 25% by weight functional materials, and c) from about 35% to about 95% by weight water; and
  • WO 92/14440 disclosing anti-dandruff shampoos comprising a surfactant, platelet zinc pyridinethione active of specific particle size, a suspending agent, water, and a synergizer for the active.
  • WO 98/00498 disclosing a composition
  • a surfactant system containing a diaionic or alkoxylated diaionic surfactant having a structural skeleton of at least five carbon atoms to which two anionic substituent groups spaced at least three atoms apart are attached, wherein one anionic substituent group is a sulfate group or an alkoxy-linked sulfate group and the other anionic substituent is selected from sulfate and sulfonate optionally alkoxy-linked, in combination with one or more other co-surfactants;
  • WO 97/14405 disclosing a shampoo compositions comprising from about 5% to about 50% by weight of a detersive surfactant, from about 0.05% to about 10% by weight of a silicone hair conditioning agent, from about 0.1% to about 10% by weight of a suspending agent, from about 0.025% to about 1.5% by weight of selected polyalkylene glycols, preferably polyethylene glycols having from about 1,500 to about 25,000 degrees of ethoxylation, and water, and optionally one or more additional materials known for use in shampoo or conditioning compositions ;
  • WO 97/25965 disclosing a shampoo composition
  • a sensitive surfactant mixture comprising a) from about 10 to about 60 percent by weight of the mixture of at least ne strong anionic surfactant, b) from about 10 to about 40 percent by weight of at least one amphoteric surfactant and c) from about 10 to about 60 percent by weight of the mixture of at least one alkyl saccharide nonionic surfactant;
  • WO 97/14406 disclosing a shampoo composition
  • a detersive anionic surfactant other than anionic amino acid derivative surfactants, a stabilizing surfactant selected from the group consisting on anionic amino acid derivative surfactants, amphoteric surfactants, cationic surfactants, and mixtures thereof, a fatty compound selected from the group consisting of fatty alcohols, fatty acids, fatty alcohol derivatives, fatty acid derivatives, and mixtures thereof, a hair conditioning agent selected from the group consisting of nonvolatile dispersed silicone conditioning gents, and mixtures thereof, and water;
  • WO 98/04233 disclosing shampoo compositions comprising an alkoxylated polyalkyleneamine and one or more detersive surfactant
  • air conditioning shampoo composition comprising by weight from about 0.01% o about 10% of alkoxylated polyalkyeneamine, from about 0.01% to about 20% of a cationic surfactant conditioning agent, from about 5% to about 50% of a detersive surfactant and from about 20% to about 90% water;
  • WO 98/04238 disclosing a shampoo composition comprising a quaternary polyalkoxylated polyalkyleneamme and a detersive surfactant, in further embodiment, a conditioning shampoo composition comprising from about by weight 0.01% to about 10% of a quaternary polyalkoxylated polyalkyleneamme, from about 0.01% to about 20% of a cationic surfactant conditioning agent, from about 5% of a detersive surfactant, and from about 20% to about 90% of water;
  • WO 98/04239 disclosing a shampoo composition
  • a shampoo composition comprising: a) from about 0.1% to about 10% by weight of short chain alkyl sulfate surfactant having a carbon chain length of 10 carbon atoms or less, b) from about 0.1% to about 10% be weight of ethoxylated alcohol and c) from about 1% to about 60% by weight of auxiliary surfactant selected from anionic surfactant other than he short chain alkyl sulfate of a) , nonionic surfactant other than the ethoxylated alcohol of b) , amphoteric and cationic surfactants and mixtures thereof, d) water;
  • WO 98/18433 disclosing shampoo compositions comprising from about 5% to about 50% by weight of a surfactant selected from the group consisting of anionic surfactants, zwitterionic or amphoteric surfactants having an attached group that is anionic at the pH of the composition, and combinations thereof, from about 0.025% to about 3% by weight of an organic cationic polymer having a cationic charge density of from about 0.2 meq/mg to about 7 meq/mg and a molecular weight of from about 5,000 to about 10 million, from about 0.1% to about 10% by weight of a water-insoluble hair styling polymer, from about 0.1% to about 10% by weight of a water- insoluble volatile solvent, and from about 0.05% to about 5% by weight of selected cationic materials for use as spreading agents for the styling polymer, and from about 22% to about 94.3% by weight water;
  • a surfactant selected from the group consisting of anionic surfactants, zwitterionic or amphoteric surfactants
  • WO 98/04241 disclosing shampoo compositions comprising: a) from about 1% to about 60% by weight of surfactant selected from anionic surfactant, nonionic, amphoteric and cationic surfactants and mixtures thereof, b) from about 0.001% to about 10% by weight of liquid polyol carboxylic acid ester containing at least four acid ester groups wherein the polyol moiety is selected from sugars and sugar alcohols containing from about 4 to about 12 hydroxyl groups, and wherein each carboxylic acid moiety has from abut 8 to about 22 carbon groups, and wherein the liquid polyol carboxylic acid ester has a complete melting point of less than about 30 °C, c) from about 0.001% to about 4% by weight of nonionic polyethylene glycol polymers having the general formula: -H (OCH2CH2) nOH wherein n is an average value of ethoxylation in the range of from about 1,000 to about 25,000, and d) water;
  • surfactant selected from
  • WO 98/18435 disclosing shampoo compositions containing a surfactant component in a shampoo with a particulate insoluble, dispersed, non- ionic conditioning agent having a particle size range of less than about 0.15 microns, crystalline agent and a deposition polymer;
  • WO 98/50007 disclosing shampoo compositions comprising a) from about 5% to about 50% by weight of a surfactant component selected from the group consisting of a combination of an anionic surfactant and an amphoteric surfactant, and a combination of an anionic surfactant and a zwitterionic surfactant, b) from about 0.025% to about 3% by weight of a cationic deposition polymer having a cationic charge density of from bout 0.2 meq/g to about 2 meq/g and which is selected from the group consisting of cationic cellulose polymers, cationic guar gum derivatives, and mixtures thereof, c) from about 0.5% to about 10% by weight of an organic cationic hair styling polymer having a cationic charge density of greater than about 2 meq/g to less than about 4.75 meq/g, and d) from about 27% to about 94.5% by weight water.
  • a surfactant component selected from the group consisting of a combination of an ani
  • styling shampoo compositions containing a combination of Polyquaternium-16 as the cationic styling polymer, Polyquaternium-10 as a cationic deposition polymer, and a surfactant matrix comprising a combination of ammonium laureth sulfate and cocoamidopropyl betaine;
  • WO 99/38475 disclosing shampoo compositions comprising from about 5% to about 50% by weight of a surfactant selected from the group consisting of anionic surfactants, zwitterionic or amphoteric surfactants having attached group that is anionic at the pH of the composition, and combinations thereof, from about 0.025% to about 3% by weight of an organic cationic polymer having a cationic charge density of from about 0.2 meq/mg to about 7 meq/mg and a molecular weight of from about 5,000 to about 10 million, from about 0.1% to about 10% by weight of a water-insoluble volatile solvent, and from about 0.005% to about 2.0% by weight a crystalline hydroxyl -containing stabilizing agent, and from about 26.5% to about 94.9% by weight water; WO 99/38476 disclosing shampoo compositions comprising from about 5% to about 50% by weight of a surfactant selected from the group consisting of anionic surfactants, zwitterionic or amphoteric surfactants, and combinations
  • WO 97/35546 disclosing shampoo compositions comprising an anionic detersive surfactant component, an anionic, cationic, hair conditioningpolymer, and from about 0.01% to about 1.0% by weight of a water insoluble, synthetic ester having a viscosity of from about 1 to about 300 centipoise, and which conforms to either of formulaes (I) and (II) wherein Rl is an alkyl, alkenyl, hydroxyalkyl or hydrox alkenyl group, having from 7 to 9 carbon atoms, n is a positive integer having a value of from 2 to 4, R2 is an alkyl, alkenyl, hydroxyalkyl or hydroxyalkenyl group, having from 8 to 10 carbon atoms, and y is an alkyl, alkenyl, hydroxy or carboxy substituted alkyl or alkenyl, having from about 2 to about 20 carbon atoms, and an organic, water insoluble conditioning oil having a viscosity of from about
  • WO 99/24004 disclosing a shampoo composition comprising by weight: a) from about 0.05% to about 50% of a polyhydrophilic anionic surfactant, b) from about 0.05% to about 20% of a cationic conditioning agent selected from the group consisting of cationic surfactants, cationic polymers, and mixtures thereof. C) from about 0.01% to about 20% of a silicone compound, and d) an aqueous carrier;
  • WO 98/50011 disclosing shampoo compositions comprising a) from about 5% to about 50% by weight of a surfactant component having an anionic moiety at the pH of the composition, b) from about 0.025% to about 3% by weight of cationic deposition polymer, c) from about 0.1% to about 10% by weight of a malodor-producing hair styling polymer, d) from about 0.0075% to about 2.5% by weight of an odor masking base, and e) from about 25% to about 94.5% by weight water.
  • the odor masking base comprises (by weight of the base) from about 15% to about 75% by weight of an ionone perfume having a boiling point of more than about 250 °C, from about 5% to about 65% by weight of a musk having a boiling point of more than about 250 °C, and from about 20% to about 80% by weight of a highly volatile perfume having a boiling point of less than about 250 °C .
  • shampoo compositions further comprising a malodor producing liquid carrier to solubilize or disperse the malodor- producing polymer in the composition;
  • WO 99/13828 disclosing shampoo compositions comprising: a) an effective amount of an optical brightener, b) an anionic detersive surfactant, c) an amphoteric detersive surfactant, d) a non-ionic detersive surfactant, and e) a carrier, wherein the composition has a pH of no higher than about 7;
  • WO 99/13829 disclosing shampoo compositions comprising: a) an effective amount of an optical brightener, b) a detersive surfactant, c) an effective amount of a polyvalent cation, and d) a carrier;
  • WO 93/18737 disclosing shampoo compositions comprising alkyl ethoxylated sulfate surfactant, a specific type of imidazolinium-type amphoteric surfactant, a crystalline suspending agent that is preferably solubilized and recrystallized in the premix composition, and a relatively low amount of water.
  • the preferred composition comprises alkyl ehtoxylated sulfate surfactant, imidazoline-type amphoteric aurfactant, betaine surfactant, a recrystallized suspending agent, and water; and
  • WO 97/35549 disclosing shampoo compositions comprising a specific surfactant component comprising and ethoxylated alkyl sulfate surfactant having from about 1 to about 8 moles of ethoxylation and an amphoteric surfactant in a shampoo with insoluble, dispersed conditioning agent, a low viscosity organic conditioning oil and a select soluble cellulosic cationic organic polymer hair conditioning agent.
  • Fig. 1 The production and subsequent purification of the antifungal polypeptide (AFPP) shown in Fig. 1 was carried out as described in WO 94/01459.
  • the antifungal polypeptide was prepared as follows:
  • A. giganteus strains The A . giganteus strain deposited with the Centraalbureau voor Schimmelculturen (CBS) under the accession number CBS 526.65 was used for the experiments.
  • Cultivation of an A. giganteus strain producing the AFPP Cultivation on agar slants was carried out using an agar medium prepared from 39 g of Potato Dextrose Agar (from Difco) and distilled water up to 1000 ml. The agar slants were inoculated with the A . giganteus strain and grown for one week at 26°C.
  • the fermentation broth obtained as described above was subjected to centrifugation, the mycelium was suspended in Tris- buffered saline at pH 7 and then subjected to a second centrifugation.
  • the supematants from the two centrifugations were combined and subjected to sterile filtration.
  • the pH of the resulting supernatant preparation was adjusted to between 6.5 and 9 and the supernatant preparation was applied to a cation exchange resin (S Sepharose Fast Flow) which prior to application was equilibrated with a phosphate buffer at pH 6.5.
  • Elution of active fractions from this resin was accomplished by the application of a buffer with a high ionic strength such as a buffer comprising 20 mM phosphate, 1.5 mM NaCl, pH 6.5. If necessary, the procedure was repeated after dilution with or dialysis against a buffer with ionic strength below or near that of 10 mM phosphate at pH 6.0. Elution from this second step was, if necessary, carried out as a gradient elution. The purity of the active fractions was assessed by HPLC .
  • a buffer with a high ionic strength such as a buffer comprising 20 mM phosphate, 1.5 mM NaCl, pH 6.5. If necessary, the procedure was repeated after dilution with or dialysis against a buffer with ionic strength below or near that of 10 mM phosphate at pH 6.0. Elution from this second step was, if necessary, carried out as a gradient elution. The purity of the active fractions was assessed by HPLC .
  • the combined active fractions were subjected to sterile filtration on a 0.22 ⁇ m filter (Millipore) prior to testing of the antifungal properties against P . ovale .
  • the purified AFPP was S-carboxymethylated using the method described by Nakaya et al . 1990 and de-salted using reverse phase HPLC.
  • the S-carboxymethylated AFPP was subjected to N- terminal amino acid sequence determination on an Applied Bio- systems 473A sequencer operated in accordance with the manufacturer's instructions.
  • the extinction coefficient of the AFPP was estimated from the amino acid sequence shown in Fig. 1 using the formula
  • the AFPP produced and purified as described above was diluted to a concentration of 25-250 ⁇ g/ml in phosphate-buffered saline, pH 6.5-8. Rabbits were immunised with the purified polypeptide in Freund's complete adjuvant by use of an immunisation scheme essentially according to the standard procedures described by Hudson et al . , 1989. Serum may be collected and tested for polyspecific antibodies against the AFPP in a single radial immunodiffusion assay or a western blot assay using the purified AFPP obtained as described above as an antigen. The assays may be carried out in accordance with standard procedures, e.g. as described by Hudson et al . , 1989. The antibodies may be purified by standard methods such as standard immunoadsorbent techniques using the purified AFPP immobilised to a carrier, e.g. as described by Hudson et al . , 1989.
  • Reactivity of a variant of the AFPP with an antibody or an antibody-containing serum obtained as described above may be determined in single radial immunodiffusion or western blotting performed essentially as described by Hudson et al . , 1989.
  • P. ovale was grown in microtiter plates in a medium recommended by American Type Culture Collection at 37°C.
  • the medium contains 30 g Sabouraud's glucose broth, 5 g yeast extract and 2 ml olive oil pr. litre.
  • a standard solution comprising the AFPP was prepared by dissolving the AFPP in 10 mM phosphate buffer, pH 7.5.
  • each microtiter plate contained 4 identical lanes, each lane having:
  • the phosphate buffer was included in order to ensure identical experimental conditions compared to the wells inoculated with P. ovale) .
  • the present example clearly shows that the AFPP impedes the growth of the yeast
  • Pi tyrosporum ovale The fact that even a very low concentration of AFPP (for example about 5 mg/litre) inhibits the growth of P. ovale renders the AFPP suitable for use in the treatment or prophylaxis of dandruff.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Mycology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Immunology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Cosmetics (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Peptides Or Proteins (AREA)

Abstract

La présente invention concerne, d'une part une composition antipelliculaire comprenant un polypeptide fongicide, et d'autre part l'utilisation d'un polypeptide fongicide pour le traitement ou la prophylaxie des pellicules. L'invention concerne également le traitement et la prophylaxie des pellicules et l'utilisation d'un polypeptide fongicide pour la préparation d'une composition destinée au traitement ou à la prophylaxie des pellicules. En l'occurrence, il s'est avéré que le polypeptide fongicide présentant la séquence d'acides aminés (figure 1) de l'invention empêche effectivement la croissance de la levure P. ovale, même à faibles concentrations.
EP99972925A 1998-11-30 1999-11-26 Composition antipelliculaire comprenant un polypeptide fongicide Withdrawn EP1143995A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DKPA199801579 1998-11-30
DK157998 1998-11-30
PCT/DK1999/000659 WO2000032220A1 (fr) 1998-11-30 1999-11-26 Composition antipelliculaire comprenant un polypeptide fongicide

Publications (1)

Publication Number Publication Date
EP1143995A1 true EP1143995A1 (fr) 2001-10-17

Family

ID=8106255

Family Applications (1)

Application Number Title Priority Date Filing Date
EP99972925A Withdrawn EP1143995A1 (fr) 1998-11-30 1999-11-26 Composition antipelliculaire comprenant un polypeptide fongicide

Country Status (6)

Country Link
EP (1) EP1143995A1 (fr)
JP (1) JP2002531413A (fr)
CN (1) CN1329500A (fr)
AU (1) AU1376000A (fr)
CA (1) CA2352749A1 (fr)
WO (1) WO2000032220A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016144918A1 (fr) 2015-03-06 2016-09-15 Atea Pharmaceuticals, Inc. Nucléotides de purine β-d-2'-désoxy-2'α-fluoro-2'-β-c-substitués-2-modifiés-n6-substitués pour le traitement du virus de l'hépatite c
WO2018013937A1 (fr) 2016-07-14 2018-01-18 Atea Pharmaceuticals, Inc. Nucléotides de purine beta-d-2'-deoxy-2'-alpha-fluoro-2'-beta-c-substitué-4'-fluoro-n6-substitué-6-amino-2-substitué pour le traitement de l'infection par le virus de l'hépatite c
WO2018048937A1 (fr) 2016-09-07 2018-03-15 Atea Pharmaceuticals, Inc. Nucléotides de purine substitués en position 2'-n 6 pour le traitement du virus à arn

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2002341503A1 (en) * 2001-05-04 2002-11-18 Novozymes A/S Antimicrobial polypeptide from aspergillus niger
WO2005034895A1 (fr) * 2003-10-10 2005-04-21 Frenchtop Natural Care Products B.V. Composition pour le lavage des cheveux et du corps
JP4745914B2 (ja) * 2005-12-01 2011-08-10 花王株式会社 毛髪洗浄剤
US8765688B2 (en) 2007-12-21 2014-07-01 Basf Se Anti-dandruff compositions containing peptides
FR2954137B1 (fr) * 2009-12-17 2012-04-20 Oreal Utilisation de peptides comme agents antipelliculaires
BR112014019897A8 (pt) 2012-02-14 2017-07-11 Univ Georgia Espiro[2.4]heptanos para tratamento de infecções por flaviviridae
FR2998785B1 (fr) * 2012-12-05 2014-11-28 Fauvert Composition de nettoyage et de soin des cheveux et/ou du cuir chevelu.

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK91192D0 (da) * 1992-07-10 1992-07-10 Novo Nordisk As Protein
WO1997022624A2 (fr) * 1995-12-16 1997-06-26 Beiersdorf Ag Preparations cosmetiques renfermant des proteines de vertebres, a effet antibacterien, antimycosique et antiviral

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0032220A1 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016144918A1 (fr) 2015-03-06 2016-09-15 Atea Pharmaceuticals, Inc. Nucléotides de purine β-d-2'-désoxy-2'α-fluoro-2'-β-c-substitués-2-modifiés-n6-substitués pour le traitement du virus de l'hépatite c
WO2018013937A1 (fr) 2016-07-14 2018-01-18 Atea Pharmaceuticals, Inc. Nucléotides de purine beta-d-2'-deoxy-2'-alpha-fluoro-2'-beta-c-substitué-4'-fluoro-n6-substitué-6-amino-2-substitué pour le traitement de l'infection par le virus de l'hépatite c
WO2018048937A1 (fr) 2016-09-07 2018-03-15 Atea Pharmaceuticals, Inc. Nucléotides de purine substitués en position 2'-n 6 pour le traitement du virus à arn
EP3865136A1 (fr) 2016-09-07 2021-08-18 ATEA Pharmaceuticals, Inc. Nucléotides de purine substitués en position 2'-n 6 pour le traitement du virus corona
EP4088725A1 (fr) 2016-09-07 2022-11-16 ATEA Pharmaceuticals, Inc. Nucléotides de purine substitués en position 2'-n6 pour le traitement du picornaviridae

Also Published As

Publication number Publication date
JP2002531413A (ja) 2002-09-24
CA2352749A1 (fr) 2000-06-08
CN1329500A (zh) 2002-01-02
AU1376000A (en) 2000-06-19
WO2000032220A1 (fr) 2000-06-08

Similar Documents

Publication Publication Date Title
DE69433280T2 (de) Rekombinantes stratum corneum chymotypisches enzym ( scce)
AU652027B2 (en) Pourable lustrous concentrate
US4140759A (en) Protein shampoo
US4233192A (en) Detergent compositions
JP3721423B2 (ja) 化粧品製剤
DE102005029704A1 (de) Verwendung von Hydrophobin-Polypeptiden sowie Konjugaten aus Hydrophobin-Polypeptiden mit Wirk-oder Effektstoffen und ihre Herstellung sowie deren Einsatz in der Kosmetik
JP3721424B2 (ja) 化粧品製剤
US20030086953A1 (en) Use of amphoteric surfactants in cosmetic compositions to precipitate cationic polymers on dilution
AU5478598A (en) A modified enzyme for skin care
DE69533359T2 (de) Veränderte menschliche c3-proteine
WO2000032220A1 (fr) Composition antipelliculaire comprenant un polypeptide fongicide
WO2006097432A2 (fr) Utilisation de polypeptides liant la keratine et fabrication
CA2077991C (fr) Produits de beaute et medicaments contenant des extensines et leur methode de preparation
DE69834174T2 (de) Epidermales protein aus der hornhautschicht und seine verwendung
EP0542309B1 (fr) Composition pour les soins des cheveux contenant des anticorps
DE60019309T2 (de) Abgabesystem für ein mittel gegen schuppen
JPH03294298A (ja) 植物タンパクポリペプチドのアシル化物またはその塩
KR20190048768A (ko) 케라틴 펩타이드를 유효성분으로 포함하는 모발 및 두피용 화장료 조성물
WO2024093910A1 (fr) Désinfectant pour les mains à base d'antiviraux et son utilisation
NZ267155A (en) Recombinant stratum corneum chymotryptic enzyme (scce)

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20010702

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE

AX Request for extension of the european patent

Free format text: AL;LT;LV;MK;RO;SI

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20030603