WO2014180600A1 - Utilisation de climbazole - Google Patents

Utilisation de climbazole Download PDF

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Publication number
WO2014180600A1
WO2014180600A1 PCT/EP2014/056082 EP2014056082W WO2014180600A1 WO 2014180600 A1 WO2014180600 A1 WO 2014180600A1 EP 2014056082 W EP2014056082 W EP 2014056082W WO 2014180600 A1 WO2014180600 A1 WO 2014180600A1
Authority
WO
WIPO (PCT)
Prior art keywords
climbazole
skin barrier
alkyl
composition
epidermal
Prior art date
Application number
PCT/EP2014/056082
Other languages
English (en)
Inventor
David Andrew Ross Jones
Fei-Ling LIM
Alison Elizabeth MOORE
Jennifer Elizabeth Pople
Duncan Charles Stuart Talbot
Original Assignee
Unilever Plc
Unilever N.V.
Conopco, Inc., D/B/A Unilever
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 Unilever Plc, Unilever N.V., Conopco, Inc., D/B/A Unilever filed Critical Unilever Plc
Publication of WO2014180600A1 publication Critical patent/WO2014180600A1/fr

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
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles

Definitions

  • the invention relates to the use of climbazole to provide an epidermal skin barrier benefit.
  • Climbazole is known as an anti-fungal agent and as such is used as an ingredient in anti- dandruff shampoos.
  • EP 2 628 479 discloses cosmetic, non-therapeutic use of climbazole for influencing the natural production of components of the extracellular matrix in the dermis, e.g. collagen, elastin, and glycosaminoglycan.
  • EP 2 633 887 discloses a cosmetic composition
  • a cosmetic composition comprising climbazole, tocopherol, glycyrrhizic acid and hyaluronic acid.
  • the cosmetic, non-therapeutic use of the composition is disclosed for the reduction of wrinkles and fine lines or for the treatment of the signs of tired and sagging skin and to improve skin hydration.
  • the epidermal skin barrier is the natural protection layer of the body.
  • the epidermal skin barrier forms an effective two-way protection barrier from the environment, preventing unwanted invasion of chemicals from outside, and preventing unregulated loss of water and nutrients from inside. We have found that climbazole can provide benefits to the epidermal skin barrier.
  • the invention thus provides in a first aspect the cosmetic use of climbazole to provide an epidermal skin barrier benefit.
  • a second aspect of the invention relates to a cosmetic method for provision of an epidermal skin barrier benefit, comprising applying to the skin a composition comprising climbazole.
  • the epidermal skin barrier benefit is selected from:
  • the epidermal skin barrier benefit is a scalp skin barrier benefit.
  • the climbazole is used in a personal care formulation comprising climbazole at a level of from 0.1 to 5 wt.%, more preferably from 0.1 to 2.5 wt.%.
  • the personal care formulation is a hair and/or scalp treatment composition. More preferably the hair and/or scalp treatment composition is a shampoo, conditioner or a leave-on composition.
  • Climbazole is an anti-fungal agent, used in anti-dandruff formulations. It is believed to act as an anti-fungal against Malessezia which is associated with dandruff symptoms.
  • Climbazole has the following chemical structure:
  • the epidermal skin barrier benefit of climbazole was ascertained by microarray analysis.
  • Human keratinocyte skin cells were treated with various doses of climbazole for a certain amount of time.
  • Cellular mRNA (transcriptome) was extracted, and microarray analysis performed. This analysis highlights activity of 20,000 genes and illustrates changes in transcriptome due to climbazole treatment. Analysis of the changes due to the effects of the climbazole was carried out to find gene expression changes due to treatment by climbazole.
  • a group of genes that showed a large transcriptome change was a group relating to epidermal differentiation. These genes encode proteins which then have biological functions.
  • the specific epidermal differentiation genes that were positively affected by treatment with climbazole are associated with the skin and specifically the skin barrier. Upregulation of these genes thus positively benefits the epidermal skin barrier, and specifically strengthening the skin barrier and/or repair of the skin barrier.
  • the climbazole is preferably used in a personal care formulation to deliver the epidermal skin barrier benefit.
  • the personal care composition of the invention may be in any form but is preferably suitable for topical application to the skin either as a leave-on or rinse-off composition.
  • the personal care formulation is a hair and/or scalp treatment composition.
  • the hair and/or scalp treatment composition is a shampoo, conditioner or a leave-on composition.
  • the personal care composition comprises a cationic deposition polymer.
  • Suitable cationic deposition polymers may be a homopolymer or be formed from two or more types of monomers.
  • the weight-average molecular weight of the polymer will generally be between 5 000 and 10 000 000 unified atomic mass units, typically at least 10 000 and preferably from 100 000 to 2 000 000.
  • the polymer will have cationic nitrogen containing groups such as quaternary ammonium or protonated amino groups, or a mixture thereof.
  • the cationic deposition polymer is cationic polysaccharide.
  • Such cationic polysaccharide includes for example, cationic celluloses and hydroxyethylcellulose, cationic starches and hydroxyalkyl starches, cationic polymer based on guar gum.
  • the cationic deposition polymer is (or comprises) cationic polygalactomannan, especially guar or cassia derived polygalactomannan modified with hydroxypropyl trimonium chloride.
  • cationic guar polymer includes Jaguar® C-14S, Jaguar® C-13S, Jaguar® C-17, Jaguar® C-500, Jaguar® C-162, Jaguar® Excel.
  • compositions contain from 0.01 % to 2% wt. of the composition cationic deposition polymer, more preferably from 0.05 to 0.5% wt. and most preferably from 0.08 to 0.25% by weight of the composition.
  • the personal care composition comprises cleansing surfactant.
  • anionic cleansing surfactants are the alkyl sulphates, alkyl ether sulphates, alkaryl sulphonates, alkanoyl isethionates, alkyl succinates, alkyl
  • alkyl ether sulphosuccinates alkyl ether sulphosuccinates, N-alkyl sarcosinates, alkyl phosphates, alkyl ether phosphates, and alkyl ether carboxylic acids and salts thereof, especially their sodium, magnesium, ammonium and mono-, di- and triethanolamine salts.
  • the alkyl and acyl groups generally contain from 8 to 18, preferably from 10 to 16 carbon atoms and may be unsaturated.
  • the alkyl ether sulphates, alkyl ether sulphosuccinates, alkyl ether phosphates and alkyl ether carboxylic acids and salts thereof may contain from 1 to 20 ethylene oxide or propylene oxide units per molecule.
  • Typical anionic cleansing surfactants for use in compositions include sodium oleyl succinate, ammonium lauryl sulphosuccinate, sodium lauryl sulphate, sodium lauryl ether sulphate, sodium lauryl ether sulphosuccinate, ammonium lauryl sulphate, ammonium lauryl ether sulphate, sodium dodecylbenzene sulphonate, triethanolamine
  • alkyl sulfates and alkyl ether sulfates. These materials have the respective formulae R 2 OS0 3 M and R-iO (C 2 H 4 0) x S0 3 M, wherein R 2 is alkyl or alkenyl of from 8 to 18 carbon atoms, x is an integer having a value of from about 1 to about 10, and M is a cation such as ammonium, alkanolamines, such as
  • R 2 has 12 to 14 carbon atoms, in a linear rather than branched chain.
  • the level of alkyl ether sulphate is from 0.5 wt% to 25 wt% of the total composition, more preferably from 3 wt% to 18 wt%, most preferably from 6 wt% to 15 wt% of the total composition.
  • the total amount of anionic cleansing surfactant generally ranges from 0.5 wt% to 45 wt%, more preferably from 1 .5 wt% to 20 wt%.
  • compositions of the invention may contain non-ionic surfactant. Most preferably non- ionic surfactants are present in the range 0 to 5 wt%.
  • Nonionic surfactants that can be included in compositions of the invention include condensation products of aliphatic (C 8 - C 18 ) primary or secondary linear or branched chain alcohols or phenols with alkylene oxides, usually ethylene oxide and generally having from 6 to 30 ethylene oxide groups.
  • Alkyl ethoxylates are particularly preferred. Most preferred are alkyl ethoxylates having the formula R-(OCH 2 CH2)nOI-l, where R is an alkyl chain of C12 to C15, and n is 5 to 9.
  • nonionic surfactants include mono- or di-alkyl alkanolamides. Examples include coco mono- or di-ethanolamide and coco mono-isopropanolamide.
  • APG alkyl polyglycosides
  • APG is one which comprises an alkyl group connected (optionally via a bridging group) to a block of one or more glycosyl groups.
  • Suitable alkyl polyglycosides for use in the invention are commercially available and include for example those materials identified as: Oramix NS10 ex Seppic; Plantaren 1200 and Plantaren 2000 ex Henkel.
  • sugar-derived nonionic surfactants which can be included in compositions of the invention include the C 10 -C 18 N-alkyl (C r C 6 ) polyhydroxy fatty acid amides, such as the C-I2-C-I8 N-methyl glucamides, as described for example in WO 92/06154 and US
  • N-alkoxy polyhydroxy fatty acid amides such as C 10 -C 18 N-(3- methoxypropyl) glucamide.
  • Amphoteric or zwitterionic surfactant can be included in an amount ranging from 0.5 wt% to about 8 wt%, more preferably from 1 wt% to 4 wt% of the total composition.
  • amphoteric or zwitterionic surfactants include alkyl amine oxides, alkyl betaines, alkyl amidopropyl betaines, alkyl sulphobetaines (sultaines), alkyl glycinates, alkyl carboxyglycinates, alkyl amphoacetates, alkyl amphopropionates,
  • Typical amphoteric and zwitterionic surfactants for use in shampoos of the invention include lauryl amine oxide, cocodimethyl sulphopropyl betaine, lauryl betaine, cocamidopropyl betaine and sodium cocoamphoacetate.
  • a particularly preferred amphoteric or zwitterionic surfactant is cocamidopropyl betaine.
  • amphoteric or zwitterionic surfactants may also be suitable.
  • Preferred mixtures are those of cocamidopropyl betaine with further amphoteric or zwitterionic surfactants as described above.
  • a preferred further amphoteric or zwitterionic surfactant is sodium cocoamphoacetate.
  • KGM-GoldTM medium Longza
  • BD Falcon T175cm 2 tissue culture flask
  • the cells were cultured following the manufacturer's instructions until approx 70% confluent.
  • the cells were then sub-cultured into 12 well tissue culture plates (BD Falcon) in KGM-Gold MediumTM with 70 ⁇ calcium, but without hydrocortisone and GA-100 antibiotic /antimycotic supplements, and incubated for 24hrs before the treatments were applied.
  • RNA samples from the cells were prepared using an RNAeasyTM micro kit (Qiagen Ltd) following the manufacturer's instructions. The medium was removed from the cells, and the cells were then washed briefly with phosphate buffered saline (DPBS) (Gibco Life Technologies Ltd) at room temperature. The cells were then lysed in buffer RLT before the sample was applied to a QiashredderTM spin column (Qiagen Ltd). The lysate was used to extract RNA following the protocol provided, final elution was made into 14 ⁇ of RNase-free water and the samples stored at -80°C until further analysis. The quantity and quality of RNA extracted from the 24 samples was analysed using the Agilent 2100 BioanalyzerTM (Agilent Technologies Ltd).
  • RNA and the appropriate amount of Agilent One-Color RNA Spike-In RNA was labelled with reagents supplied in the Quick Amp Labeling Kit, one- color according to manufacturer's instructions as follows: Primers were annealed to template by mixing 1.2 ⁇ T7 Promoter Primer, RNA and spike-in control in a volume of
  • RNaseOut (0.5 ⁇ ) were then added to make up the cDNA synthesis reaction (20 ⁇ ), which was incubated for 2h at 40 °C. After 15 min denaturation at 65°C, the reaction was made up to 60 ⁇ with the addition of Cyanine 3-CTP (to 0.3mM), Transcription Buffer (to 1 X), DTT (to 10mM), NTP (8 ⁇ ), PEG (to 4%), RNaseOUT (0.5 ⁇ ), Inorganic Phosphatase (0.6 ⁇ ), and T7 RNA Polymerase ( ⁇ . ⁇ ) and incubated for 2h at 40 °C to synthesise the fluorescent labelled cRNA.
  • the labelled cRNA was purified with the RNeasy Mini Kit (Qiagen Ltd) according to manufacturer's protocol, and quantified according to Agilent's protocol.
  • the labelled cRNA was then hybridised to the Agilent SurePrint G3 Human Gene Expression 8x60K v2 Microarray slides using reagents from the Agilent Hi-RPM Gene Expression Hybridization Kit according to manufacturer's protocol: 600ng of the labelled cRNA was used for hybridisation. Hybridisation was performed for 17 hr at 65 °C with 10 rpm rotation. Slides were then washed for 1 min at 22 °C in Wash Solution 1 , followed by 1 min in Wash Solution 2 that was pre-warmed to 37 °C, 10s in acetonitrile (Fisher), and 30s in Agilent Stabilisation and Drying Solution. Slides were scanned with the Agilent Technologies Microarray Scanner G2505C US84700251 . Data was extracted from scanned microarray images using the Agilent Feature Extraction Software (v10.7.3.1 ).
  • the PCA plot included herein is a 2D representation of the 3D image generated by the Qlcore analysis. An explanation of the usefulness of this analysis technique is described in Kalocsai P., and Shams S., Journal of Laboratory Automation October 1999, vol. 4 no. 5, 58-61 .
  • the PCA plot suggested that the microarray data generated were of high quality and there was clear evidence that the climbazole treatment had affected the transcription of genes in the keratinocytes. The data showed indicated that the higher the dose and longer the treatment time, the greater the degree of change.
  • FDR ⁇ 0.05 Benjamini Hochberg MTC
  • genes encode proteins that relate to epidermal differentiation, specifically proteins relating to skin barrier strengthening, and/or barrier repair, so upregulation of these genes by treatment with climbazole indicates beneficial effects in skin barrier strengthening and/or skin barrier repair.
  • the cornified envelope is the protective barrier of stratified squamous epithelia, and is synthesised at the late stages of keratinocyte differentiation.
  • the cornified envelope is insoluble and approximately 15nm thick. Assembly starts with the formation of a scaffold consisting of involucrin and envoplakin, subsequently other reinforcing proteins are added, such as cystatin, elafin, loricrin and small proline-rich proteins (SPRRs). These proteins serve as an attachment platform for the addition of specific lipids.
  • SRRs small proline-rich proteins
  • LCE proteins are cornified envelope precursors that have protein cross-linking function.
  • the LCE gene cluster is part of the epidermal differentiation complex present on human chromosome 1 q21 . With eighteen members, the LCE gene family is divided into six groups, LCE1 to LCE6, based on similarities of amino acid sequence, genomic organisation, and patterns of expression. Investigators have used qPCR to demonstrate that human LCE1 and LCE2 genes are primarily expressed in skin.
  • LCE genes of groups 1 , 2, 5, and 6 were significantly downregulated after tape stripping, whereas the LCE3 genes were significantly upregulated (Bergboer 201 1 ).
  • pro-inflammatory cytokines associated with psoriasis e.g. TNF-a, IL-1 a and IL-6
  • LCE3 members function as barrier repair proteins whose expression is driven by pro-inflammatory cytokines, whereas other LCE proteins have a constitutive role in barrier function of normal skin.
  • SPRRs Human small proline-rich proteins consist of a multi-gene family clustered within the epidermal differentiation complex on human chromosome 1 q21. SPRRs have a specialised role and function as cross bridging agents reinforcing the cornified envelope. Biochemical evidence has suggested that the characteristics of the cornified envelope related to toughness, strength and flexibility, exhibited by different stratified squamous epithelia, are dictated by the SPRR proteins (Cabral A et al., Structural organization and regulation of the small proline-rich family of cornified envelope precursors suggest a role in adaptive barrier function; J Biol Chem., 2001 Jun; 276(22):19231 -7).
  • Corneodesmosin, and additional cornified envelope protein was also upregulated by climbazole treatment of keratinocytes.
  • CDSN Corneodesmosin
  • these proteins have a function for epidermal skin barrier benefits, especially skin barrier repair, and skin barrier strengthening.

Abstract

La présente invention concerne l'utilisation cosmétique de climbazole pour produire un effet bénéfique de barrière cutanée et un procédé cosmétique permettant de produire un effet bénéfique de barrière cutanée par application sur la peau d'une composition comprenant du climbazole.
PCT/EP2014/056082 2013-05-07 2014-03-26 Utilisation de climbazole WO2014180600A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP13166751.1 2013-05-07
EP13166751 2013-05-07

Publications (1)

Publication Number Publication Date
WO2014180600A1 true WO2014180600A1 (fr) 2014-11-13

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021197908A1 (fr) * 2020-03-31 2021-10-07 Unilever Ip Holdings B.V. Procédé de traitement du cuir chevelu

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0747042A1 (fr) * 1995-06-06 1996-12-11 Unilever Plc Compositions contenant des dérivés azoiques pour application topique sur la peau
EP0803248A2 (fr) * 1996-04-25 1997-10-29 Unilever Plc Compositions pour les soins de la peau contenant rétinol ou rétinyl ester
US5834409A (en) * 1995-03-31 1998-11-10 Colgate-Palmolive Company Scalp care products containing anti itching/anti irritant agents
FR2872037A1 (fr) * 2004-06-25 2005-12-30 Usines Chimiques D Ivry La Bat Nouvelle utilisation cosmetique ou dermatologique de l'acide pyroglutamique
FR2902996A1 (fr) * 2006-07-03 2008-01-04 Oreal Compositions cosmetiques associant un derive c-glycoside et un derive n-acylaminoamide
US20080268077A1 (en) * 2004-10-14 2008-10-30 Symrise Gmbh & Co. Kg Process for Strengthening the Barrier Function of Undamaged Skin

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5834409A (en) * 1995-03-31 1998-11-10 Colgate-Palmolive Company Scalp care products containing anti itching/anti irritant agents
EP0747042A1 (fr) * 1995-06-06 1996-12-11 Unilever Plc Compositions contenant des dérivés azoiques pour application topique sur la peau
EP0803248A2 (fr) * 1996-04-25 1997-10-29 Unilever Plc Compositions pour les soins de la peau contenant rétinol ou rétinyl ester
FR2872037A1 (fr) * 2004-06-25 2005-12-30 Usines Chimiques D Ivry La Bat Nouvelle utilisation cosmetique ou dermatologique de l'acide pyroglutamique
US20080268077A1 (en) * 2004-10-14 2008-10-30 Symrise Gmbh & Co. Kg Process for Strengthening the Barrier Function of Undamaged Skin
FR2902996A1 (fr) * 2006-07-03 2008-01-04 Oreal Compositions cosmetiques associant un derive c-glycoside et un derive n-acylaminoamide

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021197908A1 (fr) * 2020-03-31 2021-10-07 Unilever Ip Holdings B.V. Procédé de traitement du cuir chevelu
CN115335029A (zh) * 2020-03-31 2022-11-11 联合利华知识产权控股有限公司 处理头皮的方法

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