EGF-mimicking Peptides and Other Topics

Jan 1, 2009 | Contact Author | By: Charles Fox, Independent Consultant
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Title: EGF-mimicking Peptides and Other Topics
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This month's survey of recent patent and literature research describes money-making ideas for the personal care industry including EGF-mimicking peptides and other skin treatments, as well as hair growth and makeup concepts.

Skin and Skin Care

Germanium mineral water, sericite for skin regeneration: Hyunju Home Shopping Co., Ltd., discloses a three-step method for producing a cosmetic composition containing germanium mineral water and sericite and used for promoting skin regeneration.1 In step 1, natural sericite is pulverized to particle size of less than 10 nm and mixed with mineral water containing germanium. Step 2 is the addition of oily components, water, surfactants, humectants, lower alcohols, thickening agents, coloring materials and preservatives. In the final step, the result of steps 1 and 2 is processed into a cosmetic composition in which the germanium-containing mineral water has good skin permeability. Thus, sericite nanocapsules can be rapidly permeated into the skin and adsorb waste and harmful substances, which accelerates skin regeneration.

Skin-mimicking treatment: Evonik Goldschmidt GmbH discloses skin care compositions consisting of essentially nonionic emulsifiers and a mixture of ceramides, cholesterol, and free fatty acids, in which the mixture is able to mimic skin-identical lamellar structures.2 These compositions are liquid and pumpable at room temperature, which means that they can be incorporated easily into cosmetic formulations with no need for heating. Furthermore, the compositions allow the stable inclusion of long-chain ceramides into o/w emulsions as well as into w/o emulsions. Inclusion of short-chain ceramides that can act as dermatological regulators did not affect the lamellar lipid organization.

Claims are made for the compositions as well as their use in cosmetic and dermatological formulations. A disclosed skin care composition contained ceteareth-25, glyceryl stearate, stearyl alcohol, behenic acid, cholesterol, ceramide 1, ceramide 9, ceramide 3, ceramide 6, n-hexanoyl phytosphingosine, glycerine and two proprietary ingredients.a,b

Foaming skin cleanser: Kanebo discloses skin-cleansing compositions containing an N-long-chain acyl acidic amino acid arginine salt obtained by neutralizing an N-long-chain acyl acidic amino acid with arginine at a ratio of 10/18-10/24.3 The composition may further contain a polyhydric alcohol. Liquid or cream, the composition has excellent foaming properties and provides a smooth finish to the skin. An example of a body shampoo composition is shown in Formula 1.

Antiaging via cell activation: Narisu Cosmetic Co., Ltd., discloses antiaging cosmetics containing lipids and cell activating agents.4 Antiaging skin preparations with excellent cell regenerating activities comprise cationic lipids and at least one substance selected from the group consisting of high energy phosphate compounds, riboflavin, ubiquinone and nicotinamide adenine dinucleotide phosphate (NADP). The compositions may further contain glycyrrhizinic acid derivatives and/or tocopherol derivatives. An example is shown in Formula 2.

Irritation reduction: Unilever PLC, Unilever N.V. and Hindustan Unilever Limited disclose skin benefit compositions with a vanilloid receptor antagonist and a hydroxyl acid.5 The compositions can reduce irritation of the skin, reduce wrinkles on the skin when applied, and can be formulated to contain glycolic acid and capsazepine.

Periocular hygiene: Opocrin S.p.A. discloses emollient cleansing compositions for eyelid and periocular hygiene.6 The compositions have enhanced ocular and skin tolerability. They consist of a-bisabolol as the anti-irritant ingredient in an aqueous solution containing, as main ingredients, one or more surfactants, one or more antiseptic or bactericide agents, and one or more emollient agents.

The compositions are generally usable for daily eyelid and eyelash hygiene. However, their capacity to limit irritation and burning sensation suit them particularly well for the treatment of inflammatory and infective pathologies such as blepharitis and blepharoconjunctivitis. In particular, the product can be supplied in the form of packaged sterile gauzes or wipes premoistened with the described preparation. Thus, a hygiene wipe was premoistened with the preparation shown in Formula 3.

Obesity and cellulitis: Greentech discloses the use of ferulic acid in cosmetic or pharmaceutical compositions as lipolytic agents for the prevention or treatment of obesity and/or cellulitis by systemic or local administration.7 Ferulic acid may itself be used and/or one of its salts and/or derivatives; these ingredients can be obtained from yacon plant or caigua vine. An extract of yacon was prepared and its lipolytic activity on cultured human adipocytes was shown. The formulation of a gel containing 5.00% of above extract is disclosed.

Peptides that mimic EGF: Caregen Co., Ltd., discloses peptides having activities of epidermal growth factor (EGF) but of higher stability and skin penetration potency, and their use in pharmaceutical compositions and cosmetics.8 The peptides contain the amino acid sequence Cys-Met-Tyr-Ile-Glu-Linker-Arg-Gly-Asp. They possess identical functions or activities to naturally occurring human EGF and are able to promote the generation of autocrine EGF in cells. In addition, these peptides have much higher stability and skin penetration potency than naturally occurring EGF. Therefore, a composition containing the peptide exhibited excellent treatment and prevention efficacies for diseases or conditions demanding EGF activities, and could be advantageously applied to pharmaceutical compositions, quasi-drugs and cosmetics.

Fifty milligrams of the tridecapeptide NH2-Cys-Met-Tyr-Ile-Glu-Gly(4)-Arg-Gly-Asp-Gly-OH was dissolved into 500 mL of distilled water and mixed with 5 g lecithin, 0.3 mL sodium oleate, 50 mL ethanol and a small amount of oils, and its volume was adjusted with distilled water to 1 L. The resulting solution was subjected to a microfluidizer under high pressure for emulsification, thereby providing nanosomes 100 nm in size. The nanosomes were prepared to have a final concentration of approximately 50 ppm and used as ingredients for cosmetics.

Improved percutaneous drug absorption: Improvements in stability and percutaneous drug absorption are disclosed by Rohto Pharmaceutical Co., Ltd., in an external preparation for skin.9 The preparation is comprised of a phospholipid having an iodine value of 80 to 110, ethanol at 55-83%, and 15-33% water. The preparation's stability is improved by suppressing the increase in an acid value of the phospholipid.

Also disclosed is a method for suppressing the increase in an acid value of a phospholipid by employing a composition comprising a phospholipid having a high iodine value, ethanol at a high concentration, and water. An example is shown in Formula 4.

Hair and Hair Care

Fast coloration of hair fibers: A L'Oreal patent discloses a hair dyeing process using a dye of styryl or imine type in combination with a weak acid and device for implementing the process.10 The dye composition comprises at least one dye of styryl or imine type in the presence of a revealing composition containing at least one optionally substituted aromatic compound of a weak acid type. Also disclosed is a device suitable for implementing said process.

This invention makes it possible in particular to obtain a chromatic and fast coloration of keratin fibers. This coloration is visible even on dark hair without prior lightening. It also makes it possible to obtain a coloration that, under certain conditions, does not stain. Formula 5 shows an example of such a hair dye that was applied on the hair for 30 min followed by application of a composition containing 9.40% gallic acid monohydrate, a sodium hydroxide solution qs to pH 3, and water qs to 100%, then rinsed and dried.

Manageability treatment: Unilever discloses a composition containing cucurbitine that is particularly suitable for the treatment of hair that is dry, damaged or prone to manageability challenges.11 From 0.001% to 20% of the total composition is drawn from the group consisting of cucurbitine, 2-piperazine-carboxylic acid, derivatives thereof or mixtures thereof. An example is shown in Formula 6.

Hair growth: Follica Inc. and The Trustees of the University of Pennsylvania disclose methods and kits to generate new hair follicles and grow hair by using topical compositions containing an inhibitor of a small molecule epidermal growth factor receptor (EGFR).12 The EGFR inhibitor is a non-naturally occurring, nitrogen-including heterocycle of less than about 2,000 Da or a metabolite thereof.

To illustrate the effect of administration of EGFR inhibitors on disruption-induced hair follicle neogenesis, mice were subjected to incisional wounding in a 1 cm2-area of skin surface. Inhibitor AG1478 (150 µM in 10 µL vol.) was administered in test mice as a single injection to the middle of the wound near the skin surface 11 days after wounding. EGFR inhibitor administration led to generation of more and larger hair follicles compared with control mice that were wounded only. It was concluded that more and larger hair follicles can be generated when epidermal disruption-induced hair follicle neogenesis comprises or is followed by administration of EGFR inhibitors or compounds (such as Hedgehog protein and androgen antagonists) with a similar mechanism of action.

Makeup

Eyelashes and eyebrows: Black-colored composite powders and membrane-forming ingredients are components of cosmetics for eyelashes and eyebrows, according to a patent from Kosei Co., Ltd.13 The black composite powders are obtained by coating Japan Black 401 on a flaky base with interference light. Among the membrane-forming agents are rosin acid derivatives.

In one example, titanium micac and Japan Black 401 were dispersed in water. AlCl36H2O and ZnCl2 were added to the above dispersion and neutralized using 2% sodium hydroxide solution to precipitate Japan Black 401-containing hydrotalcite-type layered double hydroxide on the titanium mica. The product was heated, washed and dried to give a composite powder. An example of a water-based mascara containing the above powder is shown in Formula 7.

Cosmetic pencil cores: Cosmetic pencil cores and their manufacture are described by Mitsubishi Pencil Co., Ltd., and Shiseido Co., Ltd.14 The invention relates to a core material containing a silica porous body and sericite with an average particle size of 3.5-10 µm. More specifically, the core material further contains boron nitride. This core material used in a pencil-type cosmetic, such as pencil-type eye shadow and eyebrow, showed excellent coloring property and mechanical strength with good feeling when used.

Also described is a method for manufacturing the core material including microwave heating treatment of a mixture containing a polysiloxane and a pigment. For example, 50 g tetraethoxysilane was mixed with 50 g ethanol for 1 hr and 100 g of a 0.01 N-HCl solution was dropped therein and further mixed for 6 hr. Thirty parts of the mixture were combined with 20 g black iron oxide, 17.5 g bengala, 27.5 parts sericite (average particle size 6.5 µm) and 15 g kaolinite (average particle size 4.8 µm), extrusion-molded, dried, washed and microwave-heated to give a core brown-color core material with a diameter of 4 mm.

Eyelids and eyebrows: Faber-Castell AG discloses an aqueous cosmetic composition for coloring eyelids and eyebrows.15 The composition contains 0.1-5% polyvinyl pyrrolidone, 4-25% of an alcohol such as ethanol or propanol, 2-15% of a moisturizer, 0.1-5% polyoxyethylene-glycerin-fatty acid ester and/or polyether-modified polysiloxane and a dye, and has a viscosity of less than 50 mPas. An example is shown in Formula 8.

Interesting Compositions

Stabilizing vitamin C derivatives: Oligosaccharides can be used to improve the stability of vitamin C derivatives, according to a three-step method disclosed by Korea Institute of Industrial Technology and Cosmol Co., Ltd.16 In step 1, an aqueous solution of chitosan oligomer is mixed with vitamin C derivatives. In step 2, the pH of the mixture is adjusted to form a complex of chitosan and the vitamin C derivative; the complex is based on the chitosan's amino group combining with the hydroxyl group and carbonyl group of the vitamin C derivative. In the final step, the complex is vacuum-distilled and dried to obtain a powder. The stability of the vitamin C derivatives, which are very sensitive to light or heat, can be improved and the powder can be applied to cosmetics for skin lightening.

W/O/W emulsions: W/O/W emulsions containing alkyl polysaccharides, phospholipids and ionic surfactants are disclosed by Nikko Chemicals Co., Ltd., and Cosmo Technical Center Co., Ltd.17 Also disclosed are external compositions and cosmetics containing those emulsions.

The water phase contains a phospholipid, an ionic surfactant, and polysaccharide that contains a saturated C6-22 linear and/or branched alkyl group. The w/o emulsion is emulsified and/or dispersed in the water phase. More specifically, the w/o emulsion contains an organo-modified clay mineral, and the water phase contains an electrolyte and/or water-soluble active component. The emulsion shows improved storage stability even with a high concentration of electrolyte in the water phase. In the example shown in Formula 9, hydroxypropyl methyl cellulose was reacted with stearyl glycidyl ether to obtain a stearyl glyceryl ether-modified polysaccharide; 96 parts of Mixture 1 was mixed with 4 parts of Mixture 2 to give a w/o/w emulsion composition.

Botulinum nanoemulsions: The University of Massachusetts discloses nanoemulsions containing Botulinum toxins.18 The nanoemulsions are prepared by high pressure microfluidization and comprise a particle size distribution in the 10-300 nm range.

These nanoemulsions are useful for the cosmetic and medical treatment of muscular contracture states. For example, Botulinum toxin may relax facial muscles such that skin wrinkles become smoother and less noticeable. Further, the present invention contemplates a cosmetic formulation that may be self-administered, for example, in the privacy of one's home and without medical supervision.

A Botulinum nanoemulsion formulation was prepared containing soybean oil, Polysorbate 80 and a commercial Botulinum toxin productd. Muscle relaxant effects of the formulation were studied in mice.

Reproduction of all or part of this article is strictly prohibited.

References

1. KR 2008 1,076, Method for producing cosmetic composition containing germanium mineral water and sericite and used for promoting skin regeneration, Hyunju Home Shopping Co Ltd, South Korea (Jan 3, 2008)
2. WO 2008 43,386, Skin care compositions containing mixtures of ceramides and cholesterol and free fatty acids, Evonik Goldschmidt GmbH, Germany (Apr 17, 2008)
3. JP 2008 94,724, Skin-cleansing compositions containing N-long-chain acyl acidic amino acid arginine salts, Kanebo Home Products Sales Co Ltd, Japan (Apr 24, 2008)
4. JP 2008 94,813, Antiaging cosmetics containing lipids and cell activating agents, Narisu Cosmetic Co Ltd, Japan (Apr 24, 2008)
5. WO 2008 46,788, Skin benefit compositions with a vanilloid receptor antagonist, Unilever PLC, Unilever NV, Hindustan Unilever Limited, UK (Apr 24, 2008)
6. WO 2008 47,394, Cleansing emollient compositions for eyelid and periocular hygiene comprising surfactants, antiseptic or bactericide agents and alpha-bisabolol, with enhanced ocular and skin tolerability, Opocrin SpA, Italy (Apr 24, 2008)
7. FR 2,907,338, Use of ferulic acid in the cosmetic and/or pharmaceutical compositions as lipolytic agents, Greentech, France (Apr 25, 2008)
8. WO 2008 44,846 , Peptides having activities of epidermal growth factor but of higher stability and skin penetration potency, and their uses in pharmaceutical compositions and cosmetics, Caregen Co Ltd, South Korea (Apr 17, 2008)
9. WO 2008 47,680, External preparation for skin containing phospholipids and ethanol for the improvement of stability and percutaneous drug absorption, Rohto Pharmaceutical Co Ltd, Japan (Apr 24, 2008)
10. WO 2008 43,967, Dyeing process using a dye of styryl or imine type in combination with a weak acid and device for implementing the process, L’Oréal, France (Apr 17, 2008)
11. WO 2008 46,753, Hair treatment composition comprising cucurbitine, Unilever PLC, Unilever NV, Hindustan Unilever Limited, UK (Apr 24, 2008)
12. WO 2008 42,216, Methods, kits, and compositions comprising small molecule EGFR inhibitor for topical administration, for generating new hair follicles and growing hair, Follica Inc, The Trustees of the University of Pennsylvania, USA (Apr 10, 2008)
13. JP 2008 88,068, Cosmetics for eyelashes and eyebrows comprising black colored composite powders and membrane-forming ingredients, Kosei Co Ltd, Japan (Apr 17, 2008)
14. JP 2008 94,773, Cosmetics pencil cores, and manufacture thereof, Mitsubishi Pencil Co Ltd, Shiseido Co Ltd, Japan (Apr 24, 2008)
15. EP 1,913,928, Cosmetic composition for coloring eyelids and eyebrows, Faber-Castell AG, Germany (Apr 23, 2008)
16. KR 2008 6,242, Method for stabilizing vitamin C derivatives with oligosaccharides, Korea Institute of Industrial Technology, Cosmol Co Ltd, South Korea (Jan 16, 2008)
17. JP 2008 88,104, W/O/W emulsions containing alkyl polysaccharides, phospholipids, and ionic surfactants, and external compositions and cosmetics containing the same, Nikko Chemicals Co Ltd, Cosmo Technical Center Co Ltd, Japan (Apr 17, 2008)
18. WO 2008 45,107, Botulinum nanoemulsions, University of Massachusetts, USA (Apr 17, 2008)

 

 

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Footnotes

aOxynex LM (INCI: (Tocopherol (and) Lecithin (and) Ascorbyl Palmitate (and) Glyceryl Stearate (and) Glyceryl Oleate (and) Citric Acid) is a product of Merck, Darmstadt, Germany.

bEuxyl K300 (INCI: Phenoxyethanol (and) Methylparaben (and) Butylparaben (and) Ethylparaben (and) Propylparaben (and) Isobutylparaben) is a product and trademark of schülke inc., Norderstedt,Germany.

cFlamenco Sparkle Red 420 (INCI: Titanium mica) is a product of Kosei Co., Ltd.

 dBotox is a product and trademark of Allergan, Inc., Irvine, Calif., USA.

Formula 1. Body Shampoo

Formula 1. Body shampoo3
Lauroyl glutamic acid l-arginine salt  25.00% w/w
Lauryl betaine 8.00
Glycerin  20.00 
Coconut fatty acid methyltaurine sodium salt   3.00
Glycol distearate  3.00
Aloe barbadensis leaf extract   0.10 
Tetrasodium EDTA  0.10
Fragrance (parfum) 0.20
Water (aqua  qs to 100.00

 

Formula 2. Antiaging lotion

Formula 2. Antiaging lotion4
Hydrogenated lecithin  5.00% w/w
Polysorbate 20 3.00
Ethanol 10.00 
Fructose-6-phosphate  5.00
Xanthan gum 0.10
Fragrance (parfum  qs
Preservative qs
Antioxidants qs
Water (aqua  qs to 100.00

 

Formula 3. Hygienic wipe

Chlorhexidine digluconate 0.180%w/w
Trideceth-10 1.000
Polysorbate-20 0.800
Propylene glycol 0.600
Bisabolol 0.200
Methylparaben 0.065
Sorensen phosphate buffer, pH = 7.00, 33.33 mM, isotonized with mannitol qs to100.000

 

Formula 4. Vehicle for improving percutaneous absorption

Formula 4. Vehicle for improving percutaneous absorption9

 

Phospholipids 2.00% w/w
Ethanol 55.00
Water (aqua) 33.90
Indomethacin 1.00
Benzyl alcohol 4.00
l-Menthol 3.00
Diisopropanolamine  0.50
Citric acid 0.50
Sodium thiosulfate 0.10
 

100.00

 

Formula 5. Hair dye

 

Oxazololindole carboxylic acid derivative 0.07% w/w
Benzyl alcohol 5.00
Ethanol 25.20
Monoethanolamine 2.00
Ammonium thioglycolate 3.34
Hydroxyethyl cellulose 1.50
Water (aqua)

 qs to 100.00

 

 

Formula 6. Hair treatment composition

Formula 6. Hair treatment composition11

 

Sodium laureth sulfate 12.00% w/w
Cocoylamidopropyldimethylglycine 2.00
Silicone emulsion 2.00
Guar hydroxypropyltrimethylammonium chloride 0.30
Preservative  0.35
Fragrance (parfum) 0.42
Citric acid

 0.17

Cucurbitine 1.00
Water (aqua)

qs to 100.00

 

 

 

Formula 7. Mascara

Formula 7. Mascara13

 

Japan Black 401 (containing hydrotalcite-type layered double hydroxide on the titanium mica) 5.00% w/w
Hydroxypropyl cellulose 4.00
Dipropylene glycol 2.00
Ethanol 40.50
Polyvinyl alcohol 0.50
Nylon fiber 5.00
Phospholipids

0.10

Phenoxyethanol 0.50
Barium sulfate

1.00

Silylated silica 2.50
Water (aqua)

qs to 100.00

 

Formula 8. Eyelid, eyebrow makeup

Formula 8. Eyelid, eyebrow makeup8

 

Water (aqua  64.50% w/w
PEG-30 glyceryl stearate (Tagat S, Evonik-Goldschmidt) 1.00
PEG/PPG-14/4-dimethicone (Abil B8851, Evonik-Degussa) 1.00
PVP 0.50
Propylene glycol 10.00
Ethanol 8.00
CI 77266

15.00

  100.00

 

Formula 9. W/O/W emulsion

Formula 9. W/O/W emulsion17

 

Mixture 1.  
Modified Polysaccharide 20.00% w/w
Hydrogenated soybean lecithin (Lecinol S-10, Nikkol) 20.00
Stearoyl N-methylacyltaurine sodium salt (SMT, Nikkol) 1.00
Glycerin 54.00
Paraffinum liquidum (mineral) oil  5.00
  100.00

 

Mixture 2. W/O emulsion  

Cyclopentasiloxane/PEG-10 dimethicone/disteardimonium hectorite (Nikkomulse WO, Nikkol)

4.00
Squalane 12.00
Isocetyl myristate 10.00
Glycerin 5.00
Butylene glycol 6.00
Sodium chloride  2.00
Preservative  qs
Water (aqua) 61.00

 

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