WO2009129855A1 - Photoprotective compositions containing peptides - Google Patents

Photoprotective compositions containing peptides Download PDF

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Publication number
WO2009129855A1
WO2009129855A1 PCT/EP2008/055008 EP2008055008W WO2009129855A1 WO 2009129855 A1 WO2009129855 A1 WO 2009129855A1 EP 2008055008 W EP2008055008 W EP 2008055008W WO 2009129855 A1 WO2009129855 A1 WO 2009129855A1
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WO
WIPO (PCT)
Prior art keywords
gly
tyr
phe
seq
ala
Prior art date
Application number
PCT/EP2008/055008
Other languages
French (fr)
Inventor
Igor Arturovic Petropavlov
Igor Anatolievich Pomytkin
Tamara Aleksandrovna Vitkalova
Original Assignee
United Technologies Ut Ag
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.)
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Publication date
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Priority to PCT/EP2008/055008 priority Critical patent/WO2009129855A1/en
Publication of WO2009129855A1 publication Critical patent/WO2009129855A1/en

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    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations

Definitions

  • the present invention relates to compositions containing peptides for the protection of a human skin against harmful effects of sunlight.
  • Solar radiation comprises ultraviolet (UV) light with wavelength ⁇ 400 nm.
  • UVA 320-400 nm
  • UVB 290- 320 nm
  • Sunscreen agents are commonly used as ingredients in sunscreen compositions to absorb, reflect, or scatter UV light and thus decrease the dose of UV radiation that reaches a human skin. As generally believed, the use of sunscreen agents may prevent photoaging of skin areas that are exposed to sunlight. However, sunscreen agents do not treat or prevent pathological processes which can be induced by UV light in a skin.
  • peptides of the present invention could prevent UV-induced harmful effects in a human skin. Moreover, the combination of these peptides with sunscreen agents could provide better protection against UV light than sunscreen agents taken alone.
  • the objectives of this present invention are: 1. to teach the use of certain peptide for the preparation of a composition for the protection of a human skin against harmful effects of sunlight,
  • the present invention provides the use of a peptide of the general formula (I): Tyr-Xi -Gly-Phe-X 2 -X 3 -Y wherein
  • Xi is GIy or Ala
  • X 2 is independently Leu, Met, lie, or VaI;
  • X 3 is absent or independently Ala, Asp, Asn, GIu, GIn, Pro, Arg, GIy, Lys, Thr, or Ser;
  • Y is absent or a sequence of 1 to 5 amino acid residues; for the preparation of a composition for the protection of a human skin against harmful effects of sunlight.
  • composition comprising:
  • X 2 is independently Leu, Met, lie, or VaI;
  • X 3 is absent or independently Ala, Asp, Asn, GIu, GIn, Pro,
  • Y is absent or a sequence of 1 to 5 amino acid residues; and (c) a dermatologically acceptable carrier.
  • amino acid refers to the natural amino acids, e.g. Asp, Asn, Arg, Cys, GIu, GIn, GIy, His, lie, Leu, Lys, Met, Phe, Ser, Thr, Tyr, and VaI. Such amino acids may be in L- or D-form.
  • the peptide of the general formula (I) contains amino acid residues in L-form.
  • the peptide of the general formula (I) contains alanine residue in D-form.
  • the peptide of the general formula (I) is selected from the group consisting of:
  • Tyr-Gly-Gly-Phe-lle-Asp (SEQ ID NO: 4) Tyr-L-Ala-Gly-Phe-lle-Asp (SEQ ID NO: 5)
  • Tyr-D-Ala-Gly-Phe-Met-Asp (SEQ ID NO: 9) Tyr-Gly-Gly-Phe-Val-Asp (SEQ ID NO: 10)
  • Tyr-D-Ala-Gly-Phe-Leu-Lys Tyr-D-Ala-Gly-Phe-Leu-Thr (SEQ ID NO: 52) Tyr-D-Ala-Gly-Phe-Leu-Ser (SEQ ID NO: 53) Tyr-D-Ala-Gly-Phe-Leu-Pro (SEQ ID NO: 54) Tyr-D-Ala-Gly-Phe-Leu-Glu-Gly-Ala-Gly-Pro-Gly (SEQ ID NO: 55) Tyr-Gly-Gly-Phe-Met (SEQ ID NO: 56)
  • composition of the present invention comprises a safe and effective amount of the peptide of the general formula (I), preferably at a level of from about 0.00001 to 10 %, preferably 0.0001 to 0.1 % by the weight of the entire composition.
  • the term "sunscreen agent” refers to any compound known from the art or developed in future that may absorb, reflect, or scatter UV light of 290 to 400 nm to diminish a dose of UV light that reaches a human skin.
  • UV light refers to UVA light with wavelength from 320 to 400 nm and UVB light with wavelength from 290 to 320 nm.
  • sunscreen agents include, but are not limited to, zinc oxide, titanium dioxide, silica, iron oxide, dibenzoylmethane, 4-isopropyl dibenzoylmethane, 4-tert.
  • butyl-4'-methoxydibenzoylmethane PARSOL 1789
  • dimethoxydibenzoylmethane 4,4'-methoxy-t- butyldibenzoylmethane
  • ethyl p-aminobenzoic acid ethyl p-aminobenzoic acid
  • octyldi methyl -p- aminobenzoic acid 2-ethylhexyl N,N-dimethyl-p-aminobenzoate
  • p- aminobenzoic acid octyl triazone
  • UVINUL T-150 dioctyl butamido triazone
  • UVASORB HEB dioctyl butamido triazone
  • cinoxate dioxybenzone, homosalate, menthylanthranilate, 2-ethylhexyl 2-cyano-3,3-diphenylacrylate
  • composition of the present invention comprises a safe and effective amount of a sunscreen agent, preferably at a level of from about
  • Two or more sunscreen agents may be used to provide a wide spectrum of protection in the UV region.
  • a combination of at least one sunscreen agent which mainly provides protection from UVA lights, and at least one sunscreen agent which mainly provide protection from UVB lights, may be used.
  • the term "dermatologically acceptable carrier” refers to one or more liquid, semi-solid, or solid diluents, which are suitable for administration to any portion of the human skin, and are compatible with the peptides of the general formula (I) of the present invention and other active or optional ingredients of the present invention.
  • examples of such carriers include, but are not limited to, distilled or deionized water, propyleneglycol, glycerol, and oil.
  • the term “harmful effects of sunlight” refers to any harmful effect in skin caused by exposure of the skin to sunlight, including sign of skin photodamage and sign of skin photoaging.
  • the term “sign of skin photodamage” refers to the skin condition, visible and/or tactile discontinuities in skin induced or caused by exposure of a skin to sunlight. Such signs include, but are not limited to erythema, also named as reddening, or sunburn.
  • the term “sign of skin photoaging” refers to the changes in appearance and/or function of human skin as a result of repeated exposure to sunlight. Such changes include, but are not limited to, wrinkles, coarseness, mottled pigmentation, sallowness, laxity, eventually premalignant, and ultimately malignant neoplasms, and other changes in the appearance and health of the skin.
  • protection includes delaying, minimizing and/or preventing signs of skin photodamage or skin photoaging induced by exposure to sunlight.
  • compositions of the present invention may comprise optional ingredients.
  • Such optional ingredients generally are used individually at levels from about 0.0005% to about 10.0%, preferably from about 0.005% to about 1.0% by weight of the composition..
  • suitable optional ingredients include, but are not limited to, depigmentation agents; humectants; antimicrobial (e.g., antibacterial) agents; anti-acne agents; anti-aging agents; anti-wrinkling agents, antiseptics; local anesthetics; wound healing promoters; deodorants and antiperspirants; skin emollients and skin moisturizers; tanning agents; skin lightening agents; antifungals; depilating agents; external analgesics; counterirhtants; anti-diaper rash agents; make-up preparations; vitamins and nutrients such as thiamin, riboflavin, niacin, pantothenates, pyridoxine, folic acid, cobalamin, biotin, choline, inositol, ascorbic acid, lipoic acid, carnitine, and etc.; amino acids and their derivatives such as alanine, arginine, asparagine, as
  • humectants include, but not limited to, water soluble liquid polyols selected from the group comprising glycerine, propylene glycol, hexylene glycol, butylene glycol, pentylene glycol, dipropylene glycol, and mixtures thereof.
  • Suitable amino acid agents include amino acids derived from the hydrolysis of various proteins as well as the salts, esters, and acyl derivatives thereof.
  • Examples of such amino acid agents nonexclusively include amphoteric amino acids such as alkylamido alkylamines, i.e.
  • stearyl acetyl glutamate capryloyl silk amino acid, caprylol collagen amino acids; capryloyl kertain amino acids; capryloyl pea amino acids; cocodimonium hydroxypropyl silk amino acids; corn gluten amino acids; cysteine; glutamic acid; glycine; hair keratin amino acids; hair amino acids such as aspartic acid, threonine, serine, glutamic acid, glycine, alanine, half-cystine, valine, methionine, isoleucine, leucine, tyrosine, phenylalanine, cysteic acid, lysine, histidine, arginine, cysteine, tryptophan, citrulline; lysine; silk amino acids, wheat amino acids; and mixtures thereof
  • suitable proteins include, but not limited to, collagen, deoxyribonuclease, iodized corn protein; keratin; milk protein; protease; serum protein; silk; sweet almond protein; wheat germ protein; wheat protein; wheat protein, alpha and beta helix of keratin proteins; hair proteins, such as intermediate filament proteins, high-sulfur proteins, ultrahigh-sulfur proteins, intermediate filament-associated proteins, high- tyrosine proteins, high-glycine tyrosine proteins, tricohyalin, arginine-rich peptides like as oligoarginines (Arg) 8 , and mixtures thereof.
  • collagen deoxyribonuclease, iodized corn protein
  • keratin milk protein
  • protease serum protein
  • silk sweet almond protein
  • wheat germ protein wheat protein
  • wheat protein wheat protein, alpha and beta helix of keratin proteins
  • hair proteins such as intermediate filament proteins, high-sulfur proteins, ultrahigh-sul
  • Suitable antiperspirants and deodorants include, but not limited to, aluminium chlorohydrates, aluminium zirconium chlorohydrates, and mixtures thereof.
  • Suitable counterirritants include, but not limited to, camphor, menthol, methyl salicylate, peppermint and clove oils, ichtammol, and mixtures thereof.
  • Suitable anti-aging agents include, but are not limited to, retinoids; vitamins such as vitamin C, vitamin B, and derivatives thereof; antioxidants including acid such as glycolic acid, citric acid, lactic acid, malic acid, mandelic acid, ascorbic acid, alpha-hydroxybutyhc acid, alpha- hydroxyisobutyric acid, alpha-hydroxyisocaproic acid, atrrolactic acid, alpha-hydroxyisovalehc acid, ethyl pyruvate, galacturonic acid, glucopehtonic acid, glucopheptono 1 ,4-lactone, gluconic acid, gluconolactone, glucuronic acid, glucurronolactone, glycolic acid, isopropyl pyruvate, methyl pyruvate, mucic acid, pyruvia acid, saccharic acid, saccaric acid 1 ,4-lactone, tartaric acid, and tartronic acid; succinic acid or
  • depigmentation agents include, but are not limited to, hydroquinone and it derivatives; vitamins such as niacin, vitamin C and its derivatives; extracts such as chamomile and green tea, and mixtures thereof.
  • Examples of skin lightening agents include, but not limited to, hydroquinone, catechol and its derivatives, ascorbic acid and its derivatives, and mixtures thereof.
  • compositions of the invention are prepared by well-known procedures. Such procedures include, but are not limited to, mixing the peptides of the present invention with other ingredients of the composition in conventional manner.
  • Guidance for the preparation of dermatological compositions of the invention can be found in " Remington: The science and practice of pharmacy” 20th ed. Mack Publishing, Easton PA, 2000 ISBN 0-912734-04-3 and " Encyclopaedia of Pharmaceutical Technology", edited by Swarbrick, J. & J. C. Boylan, Marcel Dekker, Inc., New York, 1988 ISBN 0-8247-2800-9 or a newer edition.
  • illustrative additives to dermatological compositions include, but is not limited to: ointment bases, solvents, buffering agents, pH-adjusting agents, preservatives, humectants, chelating agents, antioxidants, stabilizers, emulsifying agents, suspending agents, gel-forming agents, perfumes, and skin protective agents.
  • compositions of the present invention can be formulated in a variety of forms including, but are not limited to, lotions, gels, creams, sprays, and solutions.
  • compositions of the present invention are usually formulated to have a pH from about 4.5 to 9.5, more preferably from about 5 to about 7.5.
  • Peptides of the present invention may be prepared using solid- phase synthesis (SPPS).
  • SPPS solid- phase synthesis
  • protected amino acids in organic solvents can be added one at a time to resin-bound peptide chain, resulting in the assembly of a target peptide having a specific sequence in fully protected resin-bound form.
  • the product peptide can then be released by deprotection and cleavage from the resin support.
  • the synthesis may use manual or automatic techniques.
  • the present invention provides a method for the protection of a human skin against harmful effects of sunlight comprising administering to a subject in need thereof an effective amount of a composition which comprises a peptide of the general formula (I):
  • Xi is GIy or Ala
  • X 2 is independently Leu, Met, lie, or VaI;
  • X 3 is absent or independently Ala, Asp, Asn, GIu, GIn, Pro,
  • Y is absent or a sequence of 1 to 5 amino acid residues.
  • the composition which comprises a peptide of the formula (I) is applied onto the skin area before the exposure to sunlight in an amount from about 0.001 to 1 mg per 100 cm 2 of the skin surface, and is preferably left on the skin area for an entire period of the sunlight exposure.
  • the composition which comprises a peptide of the formula (I) is applied onto the skin area after the exposure to sunlight in an amount from about 0.001 to 1 mg per 100 cm 2 of the skin surface, and is preferably left on the skin area for at least 1 min.
  • This example demonstrates the preparation of the peptide of the present invention.
  • the peptides having an amino acid sequences of SEQ ID NO: 1 through 57 are prepared by solid-phase peptide synthesis (SPPS) technique using Applied Biosystems 430APeptide Synthesizer following the instructions provided in the instruction manual supplying by the manufacturer.
  • SPPS solid-phase peptide synthesis
  • This example demonstrates the sunscreen composition of the invention in form of a solution.
  • Peptide selected from the group consisting of SEQ ID NO: 1
  • the solution preparation The peptide is mixed with above-mentioned ingredients in the conventional manner to prepare the solution for skin protection against sunlight exposure.
  • the method of skin protection against harmful effects of a sunlight exposure with the use of the solution 1 g of above-mentioned solution is topically applied to the skin area before the exposure to sunlight, and is preferably left on the skin area for an entire period of the sunlight exposure.
  • Example 3 demonstrates the composition of the invention for the treatment of a sign of skin photoaging or skin photodamage in form of a gel. Ingredient Content
  • Peptide selected from the group consisting of SEQ ID NO: 1
  • the gel preparation The peptide is mixed with above-mentioned ingredients in the conventional manner to prepare the gel for the treatment of a sign of skin photoaging or skin photodamage caused by exposure to sunlight.
  • the method of treatment of skin a sign of skin photoaging or skin photodamage with the use of the solution 1 g of above-mentioned solution is topically applied to the skin area of a subject in need thereof before the exposure to sunlight, and is preferably left on the skin area for an entire period of the sunlight exposure.

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Abstract

The present invention relates to the use of peptides of the general formula (I): Tyr-X1-GIy-PhIe-X2-X3-Y wherein X1 is GIy or Ala; X2 is Leu, Met, lle, or VaI; X3 is absent or Ala, Asp, Asn, GIu, GIn, Pro, Arg, GIy, Lys, Thr, or Ser; Y is absent or a sequence of 1 to 5 amino acid residues; in compositions for the protection of a human skin against harmful effects of sunlight.

Description

PHOTOPROTECTIVE COMPOSITIONS CONTAINING PEPTIDES
Field of the Invention
[0001] The present invention relates to compositions containing peptides for the protection of a human skin against harmful effects of sunlight.
Background of the invention [0002] Solar radiation comprises ultraviolet (UV) light with wavelength < 400 nm. The components of UV light, UVA (320-400 nm) and UVB (290- 320 nm), are believed to be an underlying cause of photoaging of a human skin. Physiology, Biochemistry, and Molecular Biology of the Skin, 2nd Ed., ed. by L. A. Goldsmith (New York: Oxford Univ. Press, 1991 ).
[0003] Sunscreen agents are commonly used as ingredients in sunscreen compositions to absorb, reflect, or scatter UV light and thus decrease the dose of UV radiation that reaches a human skin. As generally believed, the use of sunscreen agents may prevent photoaging of skin areas that are exposed to sunlight. However, sunscreen agents do not treat or prevent pathological processes which can be induced by UV light in a skin.
[0004] It was found that peptides of the present invention could prevent UV-induced harmful effects in a human skin. Moreover, the combination of these peptides with sunscreen agents could provide better protection against UV light than sunscreen agents taken alone.
[0005] The objectives of this present invention are: 1. to teach the use of certain peptide for the preparation of a composition for the protection of a human skin against harmful effects of sunlight,
2. To provide a special composition for the protection of a human skin against harmful effects of sunlight,
3. To teach a method for the protection of a human skin against harmful effects of sunlight by administering a special composition.
These objectives are achieved by the use of a peptide according to claim 1 , by the composition according to claim 4 and by the method according to claim 13.
Detailed Description of the Invention
[0006] The present invention provides the use of a peptide of the general formula (I): Tyr-Xi -Gly-Phe-X2-X3-Y wherein
Xi is GIy or Ala;
X2 is independently Leu, Met, lie, or VaI; X3 is absent or independently Ala, Asp, Asn, GIu, GIn, Pro, Arg, GIy, Lys, Thr, or Ser;
Y is absent or a sequence of 1 to 5 amino acid residues; for the preparation of a composition for the protection of a human skin against harmful effects of sunlight.
[0007] Further, the present invention provides a composition comprising:
(a) a sunscreen agent;
(b) a peptide of the general formula (I):
Tyr-Xi -Gly-Phe-X2-X3-Y wherein Xi is GIy or Ala;
X2 is independently Leu, Met, lie, or VaI;
X3 is absent or independently Ala, Asp, Asn, GIu, GIn, Pro,
Arg, GIy, Lys, Thr, or Ser; Y is absent or a sequence of 1 to 5 amino acid residues; and (c) a dermatologically acceptable carrier.
[0008] As used herein, the term "amino acid" refers to the natural amino acids, e.g. Asp, Asn, Arg, Cys, GIu, GIn, GIy, His, lie, Leu, Lys, Met, Phe, Ser, Thr, Tyr, and VaI. Such amino acids may be in L- or D-form.
[0009] In the preferred embodiments of the present invention, the peptide of the general formula (I) contains amino acid residues in L-form.
[0010] In some of the preferred embodiments of the present invention, the peptide of the general formula (I) contains alanine residue in D-form.
[0011] In the preferred embodiments of the present invention, the peptide of the general formula (I) is selected from the group consisting of:
Tyr-Gly-Gly-Phe-Leu-Asp (SEQ ID NO: 1 )
Tyr-L-Ala-Gly-Phe-Leu-Asp (SEQ ID NO: 2)
Tyr-D-Ala-Gly-Phe-Leu-Asp (SEQ ID NO: 3)
Tyr-Gly-Gly-Phe-lle-Asp (SEQ ID NO: 4) Tyr-L-Ala-Gly-Phe-lle-Asp (SEQ ID NO: 5)
Tyr-D-Ala-Gly-Phe-lle-Asp (SEQ ID NO: 6)
Tyr-Gly-Gly-Phe-Met-Asp (SEQ ID NO: 7)
Tyr-L-Ala-Gly-Phe-Met-Asp (SEQ ID NO: 8)
Tyr-D-Ala-Gly-Phe-Met-Asp (SEQ ID NO: 9) Tyr-Gly-Gly-Phe-Val-Asp (SEQ ID NO: 10)
Tyr-L-Ala-Gly-Phe-Val-Asp (SEQ ID NO: 11 )
Tyr-D-Ala-Gly-Phe-Val-Asp (SEQ ID NO: 12)
Tyr-Gly-Gly-Phe-Leu-Asn (SEQ ID NO: 13)
Tyr-L-Ala-Gly-Phe-Leu-Asn (SEQ ID NO: 14) Tyr-D-Ala-Gly-Phe-Leu-Asn (SEQ ID NO: 15)
Tyr-Gly-Gly-Phe-lle-Asn (SEQ ID NO: 16)
Tyr-L-Ala-Gly-Phe-lle-Asn (SEQ ID NO: 17)
Tyr-D-Ala-Gly-Phe-lle-Asn (SEQ ID NO: 18) Tyr-Gly-Gly-Phe-Met-Asn (SEQ ID NO: 19)
Tyr-L-Ala-Gly-Phe-Met-Asn (SEQ ID NO: 20)
Tyr-D-Ala-Gly-Phe-Met-Asn (SEQ ID NO: 21)
Tyr-Gly-Gly-Phe-Val-Asn (SEQ ID NO: 22) Tyr-L-Ala-Gly-Phe-Val-Asn (SEQ ID NO: 23)
Tyr-D-Ala-Gly-Phe-Val-Asn (SEQ ID NO: 24)
Tyr-Gly-Gly-Phe-Leu-Glu (SEQ ID NO: 25)
Tyr-Ala-Gly-Phe-Leu-Glu (SEQ ID NO: 26)
Tyr-D-Ala-Gly-Phe-Leu-Glu (SEQ ID NO: 27) Tyr-Gly-Gly-Phe-lle-Glu (SEQ ID NO: 28)
Tyr-L-Ala-Gly-Phe-lle-Glu (SEQ ID NO: 29)
Tyr-D-Ala-Gly-Phe-lle-Glu (SEQ ID NO: 30)
Tyr-Gly-Gly-Phe-Met-Glu (SEQ ID NO: 31)
Tyr-L-Ala-Gly-Phe-Met-Glu (SEQ ID NO: 32) Tyr-D-Ala-Gly-Phe-Met-Glu (SEQ ID NO: 33)
Tyr-Gly-Gly-Phe-Val-Glu (SEQ ID NO: 34)
Tyr-L-Ala-Gly-Phe-Val-Glu (SEQ ID NO: 35)
Tyr-D-Ala-Gly-Phe-Val-Glu (SEQ ID NO: 36)
Tyr-Gly-Gly-Phe-Leu-Gln (SEQ ID NO: 37) Tyr-Ala-Gly-Phe-Leu-Gln (SEQ ID NO: 38)
Tyr-D-Ala-Gly-Phe-Leu-Gln (SEQ ID NO: 39)
Tyr-Gly-Gly-Phe-lle-Gln (SEQ ID NO: 40)
Tyr-L-Ala-Gly-Phe-lle-Gln (SEQ ID NO: 41)
Tyr-D-Ala-Gly-Phe-lle-Gln (SEQ ID NO: 42) Tyr-Gly-Gly-Phe-Met-Gln (SEQ ID NO: 43)
Tyr-L-Ala-Gly-Phe-Met-Gln (SEQ ID NO: 44)
Tyr-D-Ala-Gly-Phe-Met-Gln (SEQ ID NO: 45)
Tyr-Gly-Gly-Phe-Val-Gln (SEQ ID NO: 46)
Tyr-L-Ala-Gly-Phe-Val-Gln (SEQ ID NO: 47) Tyr-D-Ala-Gly-Phe-Val-Gln (SEQ ID NO: 48)
Tyr-D-Ala-Gly-Phe-Leu-Arg (SEQ ID NO: 49)
Tyr-D-Ala-Gly-Phe-Leu-Gly (SEQ ID NO: 50)
Tyr-D-Ala-Gly-Phe-Leu-Lys (SEQ ID NO: 51) Tyr-D-Ala-Gly-Phe-Leu-Thr (SEQ ID NO: 52) Tyr-D-Ala-Gly-Phe-Leu-Ser (SEQ ID NO: 53) Tyr-D-Ala-Gly-Phe-Leu-Pro (SEQ ID NO: 54) Tyr-D-Ala-Gly-Phe-Leu-Glu-Gly-Ala-Gly-Pro-Gly (SEQ ID NO: 55) Tyr-Gly-Gly-Phe-Met (SEQ ID NO: 56)
Tyr-Gly-Gly-Phe-Leu (SEQ ID NO: 57)
[0012] The composition of the present invention comprises a safe and effective amount of the peptide of the general formula (I), preferably at a level of from about 0.00001 to 10 %, preferably 0.0001 to 0.1 % by the weight of the entire composition.
[0013] As used herein, the term "sunscreen agent" refers to any compound known from the art or developed in future that may absorb, reflect, or scatter UV light of 290 to 400 nm to diminish a dose of UV light that reaches a human skin.
[0014] As used herein, the term "UV light" refers to UVA light with wavelength from 320 to 400 nm and UVB light with wavelength from 290 to 320 nm.
[0015] A wide variety of conventional sunscreen agents are suitable for use herein. Such agents include, but are not limited to, zinc oxide, titanium dioxide, silica, iron oxide, dibenzoylmethane, 4-isopropyl dibenzoylmethane, 4-tert. butyl-4'-methoxydibenzoylmethane (PARSOL 1789), dimethoxydibenzoylmethane, 4,4'-methoxy-t- butyldibenzoylmethane, ethyl p-aminobenzoic acid, octyldi methyl -p- aminobenzoic acid, 2-ethylhexyl N,N-dimethyl-p-aminobenzoate, p- aminobenzoic acid, octyl triazone (UVINUL T-150), dioctyl butamido triazone (UVASORB HEB), cinoxate, dioxybenzone, homosalate, menthylanthranilate, 2-ethylhexyl 2-cyano-3,3-diphenylacrylate
(octocrylene, PARSOL 340), ethyl 2-cyano-3,3-diphenylacrylate, octyl methoxycinnamate, octyl salicylate, homomenthyl salicylate, TEA salicylate, trolamine salicylate, oxybenzone, padimate O, phenylbenzimidazole sulfonic acid, sulisobenzone, octyl methoxycinnamate (PARSOL MCX), ethoxyethyl methoxycinnamate, diethanolamine methoxycinnamate (PARSOL Hydro), isoamyl methoxycinnamate, octyl methoxycinnamate, 2-ethylhexyl-p- methoxycinnamate (commercially available as PARSOL MCX), drometrizole trisiloxane, 4-methyl benzylidene camphor (PARSOL 5000), 3-benzylidene camphor, 3-(4-methylbenzylidene) camphor, camphor benzalkonium methosulfate, polyacrylamidomethyl benzylidene camphor, sulfo benzylidene camphor, sulphomethyl benzylidene camphor, therephthalidene dicamphor sulfonic acid, hydroxy methylphenyl benzotriazole, methylene bis-benzotriazoyltetramethylbutylphenol, 2- hydroxy-4-methoxybenzo-phenone, 2-phenylbenzimidazole-5-sulfonic acid, 2-phenyl benzimidazole sulfonic acid, or any derivatives, or any combinations thereof. Other useful sunscreen agents include those disclosed in Segarin, et al, at Chapter VIII, pages 189 et seq., of Cosmetics Science and Technology (1972).
[0016] The composition of the present invention comprises a safe and effective amount of a sunscreen agent, preferably at a level of from about
0.5% to about 40%, more preferably from about 1 % to about 20% by weight of the entire composition. Two or more sunscreen agents may be used to provide a wide spectrum of protection in the UV region. For example, a combination of at least one sunscreen agent which mainly provides protection from UVA lights, and at least one sunscreen agent which mainly provide protection from UVB lights, may be used.
[0017] As used herein, the term "dermatologically acceptable carrier" refers to one or more liquid, semi-solid, or solid diluents, which are suitable for administration to any portion of the human skin, and are compatible with the peptides of the general formula (I) of the present invention and other active or optional ingredients of the present invention. Examples of such carriers include, but are not limited to, distilled or deionized water, propyleneglycol, glycerol, and oil.
[0018] As used herein, the term "harmful effects of sunlight" refers to any harmful effect in skin caused by exposure of the skin to sunlight, including sign of skin photodamage and sign of skin photoaging. As used herein, the term "sign of skin photodamage" refers to the skin condition, visible and/or tactile discontinuities in skin induced or caused by exposure of a skin to sunlight. Such signs include, but are not limited to erythema, also named as reddening, or sunburn. As used herein, the term "sign of skin photoaging" refers to the changes in appearance and/or function of human skin as a result of repeated exposure to sunlight. Such changes include, but are not limited to, wrinkles, coarseness, mottled pigmentation, sallowness, laxity, eventually premalignant, and ultimately malignant neoplasms, and other changes in the appearance and health of the skin.
[0019] The term "protection" includes delaying, minimizing and/or preventing signs of skin photodamage or skin photoaging induced by exposure to sunlight.
[0020] The compositions of the present invention may comprise optional ingredients. Such optional ingredients generally are used individually at levels from about 0.0005% to about 10.0%, preferably from about 0.005% to about 1.0% by weight of the composition..
[0021] Examples of suitable optional ingredients include, but are not limited to, depigmentation agents; humectants; antimicrobial (e.g., antibacterial) agents; anti-acne agents; anti-aging agents; anti-wrinkling agents, antiseptics; local anesthetics; wound healing promoters; deodorants and antiperspirants; skin emollients and skin moisturizers; tanning agents; skin lightening agents; antifungals; depilating agents; external analgesics; counterirhtants; anti-diaper rash agents; make-up preparations; vitamins and nutrients such as thiamin, riboflavin, niacin, pantothenates, pyridoxine, folic acid, cobalamin, biotin, choline, inositol, ascorbic acid, lipoic acid, carnitine, and etc.; amino acids and their derivatives such as alanine, arginine, asparagine, aspartic acid, carnitine, citrulline, cysteine, dimethylglycine, gamma-aminobutyric acid, glutamic acid, glutamine, glutathione, glycine, histidine, isoleucine, leucine, lysine, methionine, ornithine, phenylalanine, proline, serine, taurine, threonine, tryptophan, tyrosine, valine; minerals such as boron, calcium, chromium, cobalt, copper, fluoride, germanium, iodine, iron, lithium, magnesium, manganese, molybdenum, phosphorus, potassium, selenium, silicon, sodium, sulfur, vanadium, zinc; herbal extracts; retinoids; bioflavonoids; anti-oxidants; skin conditioners; hair lighteners; chelating agents; cell turnover enhancers; coloring agents; and mixtures thereof.
[0022] Examples of suitable humectants include, but not limited to, water soluble liquid polyols selected from the group comprising glycerine, propylene glycol, hexylene glycol, butylene glycol, pentylene glycol, dipropylene glycol, and mixtures thereof.
[0023] Suitable amino acid agents include amino acids derived from the hydrolysis of various proteins as well as the salts, esters, and acyl derivatives thereof. Examples of such amino acid agents nonexclusively include amphoteric amino acids such as alkylamido alkylamines, i.e. stearyl acetyl glutamate, capryloyl silk amino acid, caprylol collagen amino acids; capryloyl kertain amino acids; capryloyl pea amino acids; cocodimonium hydroxypropyl silk amino acids; corn gluten amino acids; cysteine; glutamic acid; glycine; hair keratin amino acids; hair amino acids such as aspartic acid, threonine, serine, glutamic acid, glycine, alanine, half-cystine, valine, methionine, isoleucine, leucine, tyrosine, phenylalanine, cysteic acid, lysine, histidine, arginine, cysteine, tryptophan, citrulline; lysine; silk amino acids, wheat amino acids; and mixtures thereof
[0024] Examples of suitable proteins include, but not limited to, collagen, deoxyribonuclease, iodized corn protein; keratin; milk protein; protease; serum protein; silk; sweet almond protein; wheat germ protein; wheat protein; wheat protein, alpha and beta helix of keratin proteins; hair proteins, such as intermediate filament proteins, high-sulfur proteins, ultrahigh-sulfur proteins, intermediate filament-associated proteins, high- tyrosine proteins, high-glycine tyrosine proteins, tricohyalin, arginine-rich peptides like as oligoarginines (Arg)8, and mixtures thereof.
[0025] Examples of suitable antiperspirants and deodorants include, but not limited to, aluminium chlorohydrates, aluminium zirconium chlorohydrates, and mixtures thereof.
[0026] Examples of suitable counterirritants include, but not limited to, camphor, menthol, methyl salicylate, peppermint and clove oils, ichtammol, and mixtures thereof.
[0027] Examples of suitable anti-aging agents include, but are not limited to, retinoids; vitamins such as vitamin C, vitamin B, and derivatives thereof; antioxidants including acid such as glycolic acid, citric acid, lactic acid, malic acid, mandelic acid, ascorbic acid, alpha-hydroxybutyhc acid, alpha- hydroxyisobutyric acid, alpha-hydroxyisocaproic acid, atrrolactic acid, alpha-hydroxyisovalehc acid, ethyl pyruvate, galacturonic acid, glucopehtonic acid, glucopheptono 1 ,4-lactone, gluconic acid, gluconolactone, glucuronic acid, glucurronolactone, glycolic acid, isopropyl pyruvate, methyl pyruvate, mucic acid, pyruvia acid, saccharic acid, saccaric acid 1 ,4-lactone, tartaric acid, and tartronic acid; succinic acid or salts thereof; acids such as beta-hydroxybutyric acid, beta-phenyl-lactic acid, beta-phenylpyruvic acid; botanical extracts such as green tea, soy, milk thistle, algae, aloe, angelica, bitter orange, coffee, goldthread, grapefruit, hoellen, honeysuckle, Job's tears, lithospermum, mulberry, peony, puerarua, rice, safflower, and mixtures thereof.
[0028] Examples of suitable depigmentation agents include, but are not limited to, hydroquinone and it derivatives; vitamins such as niacin, vitamin C and its derivatives; extracts such as chamomile and green tea, and mixtures thereof.
[0029] Examples of skin lightening agents include, but not limited to, hydroquinone, catechol and its derivatives, ascorbic acid and its derivatives, and mixtures thereof.
[0030] The compositions of the invention are prepared by well-known procedures. Such procedures include, but are not limited to, mixing the peptides of the present invention with other ingredients of the composition in conventional manner. Guidance for the preparation of dermatological compositions of the invention can be found in " Remington: The science and practice of pharmacy" 20th ed. Mack Publishing, Easton PA, 2000 ISBN 0-912734-04-3 and " Encyclopaedia of Pharmaceutical Technology", edited by Swarbrick, J. & J. C. Boylan, Marcel Dekker, Inc., New York, 1988 ISBN 0-8247-2800-9 or a newer edition. As well known to the skilled person, illustrative additives to dermatological compositions include, but is not limited to: ointment bases, solvents, buffering agents, pH-adjusting agents, preservatives, humectants, chelating agents, antioxidants, stabilizers, emulsifying agents, suspending agents, gel-forming agents, perfumes, and skin protective agents.
[0031] The compositions of the present invention can be formulated in a variety of forms including, but are not limited to, lotions, gels, creams, sprays, and solutions.
[0032] The compositions of the present invention are usually formulated to have a pH from about 4.5 to 9.5, more preferably from about 5 to about 7.5.
[0033] Peptides of the present invention may be prepared using solid- phase synthesis (SPPS). In preferred embodiments of the present invention, according to SPPS technique, protected amino acids in organic solvents can be added one at a time to resin-bound peptide chain, resulting in the assembly of a target peptide having a specific sequence in fully protected resin-bound form. The product peptide can then be released by deprotection and cleavage from the resin support. The synthesis may use manual or automatic techniques.
[0034] Further, the present invention provides a method for the protection of a human skin against harmful effects of sunlight comprising administering to a subject in need thereof an effective amount of a composition which comprises a peptide of the general formula (I):
Tyr-Xi -Gly-Phe-X2-X3-Y wherein
Xi is GIy or Ala;
X2 is independently Leu, Met, lie, or VaI; X3 is absent or independently Ala, Asp, Asn, GIu, GIn, Pro,
Arg, GIy, Lys, Thr, or Ser; Y is absent or a sequence of 1 to 5 amino acid residues.
[0035] In the preferred embodiments of the present invention, the composition which comprises a peptide of the formula (I) is applied onto the skin area before the exposure to sunlight in an amount from about 0.001 to 1 mg per 100 cm2 of the skin surface, and is preferably left on the skin area for an entire period of the sunlight exposure.
[0036] In other preferred embodiments of the present invention, the composition which comprises a peptide of the formula (I) is applied onto the skin area after the exposure to sunlight in an amount from about 0.001 to 1 mg per 100 cm2 of the skin surface, and is preferably left on the skin area for at least 1 min.
[0037] The following examples are presented to demonstrate the invention. The examples are illustrative only and are not intended to limit the scope of the invention in any way. Example 1.
[0038] This example demonstrates the preparation of the peptide of the present invention. The peptides having an amino acid sequences of SEQ ID NO: 1 through 57 are prepared by solid-phase peptide synthesis (SPPS) technique using Applied Biosystems 430APeptide Synthesizer following the instructions provided in the instruction manual supplying by the manufacturer.
Example 2
[0039] This example demonstrates the sunscreen composition of the invention in form of a solution.
Ingredient Content
PARSOL 1789 170 mg
Peptide selected from the group consisting of SEQ
ID NO: 1 through 57 1 mg
Phosphate buffer qs to pH 5.5
Deionized water to 10.0 ml
The solution preparation: The peptide is mixed with above-mentioned ingredients in the conventional manner to prepare the solution for skin protection against sunlight exposure.
The method of skin protection against harmful effects of a sunlight exposure with the use of the solution: 1 g of above-mentioned solution is topically applied to the skin area before the exposure to sunlight, and is preferably left on the skin area for an entire period of the sunlight exposure.
Example 3 [0040] This example demonstrates the composition of the invention for the treatment of a sign of skin photoaging or skin photodamage in form of a gel. Ingredient Content
Peptide selected from the group consisting of SEQ
ID NO: 1 through 57 1 mg
Phosphate buffer qs to pH 5.5
Ethylcellulose 60 mg
Deionized water to 10.0 ml
The gel preparation: The peptide is mixed with above-mentioned ingredients in the conventional manner to prepare the gel for the treatment of a sign of skin photoaging or skin photodamage caused by exposure to sunlight.
The method of treatment of skin a sign of skin photoaging or skin photodamage with the use of the solution: 1 g of above-mentioned solution is topically applied to the skin area of a subject in need thereof before the exposure to sunlight, and is preferably left on the skin area for an entire period of the sunlight exposure.

Claims

Patent Claims
1. Use of a peptide of the general formula (I):
Tyr-Xi -Gly-Phe-X2-X3-Y wherein
Xi is GIy or Ala;
X2 is independently Leu, Met, lie, or VaI; X3 is absent or independently Ala, Asp, Asn, GIu, GIn, Pro, Arg, GIy, Lys, Thr, or Ser; Y is absent or a sequence of 1 to 5 amino acid residues; for the preparation of a composition for the protection of a human skin against harmful effects of sunlight.
2. The use of claim 1 , wherein the peptide is selected from the group consisting of
Tyr-Gly-Gly-Phe-Leu-Asp (SEQ ID NO: 1 )
Tyr-L-Ala-Gly-Phe-Leu-Asp (SEQ ID NO: 2)
Tyr-D-Ala-Gly-Phe-Leu-Asp (SEQ ID NO: 3)
Tyr-Gly-Gly-Phe-lle-Asp (SEQ ID NO: 4) Tyr-L-Ala-Gly-Phe-lle-Asp (SEQ ID NO: 5)
Tyr-D-Ala-Gly-Phe-lle-Asp (SEQ ID NO: 6)
Tyr-Gly-Gly-Phe-Met-Asp (SEQ ID NO: 7)
Tyr-L-Ala-Gly-Phe-Met-Asp (SEQ ID NO: 8)
Tyr-D-Ala-Gly-Phe-Met-Asp (SEQ ID NO: 9) Tyr-Gly-Gly-Phe-Val-Asp (SEQ ID NO: 10)
Tyr-L-Ala-Gly-Phe-Val-Asp (SEQ ID NO: 11 )
Tyr-D-Ala-Gly-Phe-Val-Asp (SEQ ID NO: 12)
Tyr-Gly-Gly-Phe-Leu-Asn (SEQ ID NO: 13)
Tyr-L-Ala-Gly-Phe-Leu-Asn (SEQ ID NO: 14) Tyr-D-Ala-Gly-Phe-Leu-Asn (SEQ ID NO: 15)
Tyr-Gly-Gly-Phe-lle-Asn (SEQ ID NO: 16)
Tyr-L-Ala-Gly-Phe-lle-Asn (SEQ ID NO: 17)
Tyr-D-Ala-Gly-Phe-lle-Asn (SEQ ID NO: 18) Tyr-Gly-Gly-Phe-Met-Asn (SEQ ID NO: 19)
Tyr-L-Ala-Gly-Phe-Met-Asn (SEQ ID NO: 20)
Tyr-D-Ala-Gly-Phe-Met-Asn (SEQ ID NO: 21)
Tyr-Gly-Gly-Phe-Val-Asn (SEQ ID NO: 22) Tyr-L-Ala-Gly-Phe-Val-Asn (SEQ ID NO: 23)
Tyr-D-Ala-Gly-Phe-Val-Asn (SEQ ID NO: 24)
Tyr-Gly-Gly-Phe-Leu-Glu (SEQ ID NO: 25)
Tyr-Ala-Gly-Phe-Leu-Glu (SEQ ID NO: 26)
Tyr-D-Ala-Gly-Phe-Leu-Glu (SEQ ID NO: 27) Tyr-Gly-Gly-Phe-lle-Glu (SEQ ID NO: 28)
Tyr-L-Ala-Gly-Phe-lle-Glu (SEQ ID NO: 29)
Tyr-D-Ala-Gly-Phe-lle-Glu (SEQ ID NO: 30)
Tyr-Gly-Gly-Phe-Met-Glu (SEQ ID NO: 31)
Tyr-L-Ala-Gly-Phe-Met-Glu (SEQ ID NO: 32) Tyr-D-Ala-Gly-Phe-Met-Glu (SEQ ID NO: 33)
Tyr-Gly-Gly-Phe-Val-Glu (SEQ ID NO: 34)
Tyr-L-Ala-Gly-Phe-Val-Glu (SEQ ID NO: 35)
Tyr-D-Ala-Gly-Phe-Val-Glu (SEQ ID NO: 36)
Tyr-Gly-Gly-Phe-Leu-Gln (SEQ ID NO: 37) Tyr-Ala-Gly-Phe-Leu-Gln (SEQ ID NO: 38)
Tyr-D-Ala-Gly-Phe-Leu-Gln (SEQ ID NO: 39)
Tyr-Gly-Gly-Phe-lle-Gln (SEQ ID NO: 40)
Tyr-L-Ala-Gly-Phe-lle-Gln (SEQ ID NO: 41)
Tyr-D-Ala-Gly-Phe-lle-Gln (SEQ ID NO: 42) Tyr-Gly-Gly-Phe-Met-Gln (SEQ ID NO: 43)
Tyr-L-Ala-Gly-Phe-Met-Gln (SEQ ID NO: 44)
Tyr-D-Ala-Gly-Phe-Met-Gln (SEQ ID NO: 45)
Tyr-Gly-Gly-Phe-Val-Gln (SEQ ID NO: 46)
Tyr-L-Ala-Gly-Phe-Val-Gln (SEQ ID NO: 47) Tyr-D-Ala-Gly-Phe-Val-Gln (SEQ ID NO: 48)
Tyr-D-Ala-Gly-Phe-Leu-Arg (SEQ ID NO: 49)
Tyr-D-Ala-Gly-Phe-Leu-Gly (SEQ ID NO: 50)
Tyr-D-Ala-Gly-Phe-Leu-Lys (SEQ ID NO: 51) Tyr-D-Ala-Gly-Phe-Leu-Thr (SEQ ID NO: 52) Tyr-D-Ala-Gly-Phe-Leu-Ser (SEQ ID NO: 53) Tyr-D-Ala-Gly-Phe-Leu-Pro (SEQ ID NO: 54) Tyr-D-Ala-Gly-Phe-Leu-Glu-Gly-Ala-Gly-Pro-Gly (SEQ ID NO: 55) Tyr-Gly-Gly-Phe-Met (SEQ ID NO: 56)
Tyr-Gly-Gly-Phe-Leu (SEQ ID NO: 57)
3. The use of claim 1 , wherein the harmful effect of sunlight is selected from the group consisting of erythema, sunburn, wrinkles, coarseness, mottled pigmentation, sallowness, laxity, eventually premalignant, and ultimately malignant neoplasms.
4. A composition comprising: (a) a sunscreen agent; (b) a peptide of the general formula (I):
Tyr-Xi -GIy-PhIe-X2-X3-Y wherein
Xi is GIy or Ala;
X2 is independently Leu, Met, lie, or VaI; X3 is absent or independently Ala, Asp, Asn, GIu, GIn, Pro,
Arg, GIy, Lys, Thr, or Ser;
Y is absent or a sequence of 1 to 5 amino acid residues; and (c) a dermatologically acceptable carrier.
5. The composition of claim 4, wherein the peptide of the general formula (I) contains amino acid residues in L-form.
6. The composition of claim 4, wherein the peptide of the general formula (I) contains alanine residue in D-form.
7. The composition of claim 4, wherein the peptide is selected from the group consisting of
Tyr-Gly-Gly-Phe-Leu-Asp (SEQ ID NO: 1 ) Tyr-L-Ala-Gly-Phe-Leu-Asp (SEQ ID NO: 2)
Tyr-D-Ala-Gly-Phe-Leu-Asp (SEQ ID NO: 3)
Tyr-Gly-Gly-Phe-lle-Asp (SEQ ID NO: 4)
Tyr-L-Ala-Gly-Phe-lle-Asp (SEQ ID NO: 5) Tyr-D-Ala-Gly-Phe-lle-Asp (SEQ ID NO: 6)
Tyr-Gly-Gly-Phe-Met-Asp (SEQ ID NO: 7)
Tyr-L-Ala-Gly-Phe-Met-Asp (SEQ ID NO: 8)
Tyr-D-Ala-Gly-Phe-Met-Asp (SEQ ID NO: 9)
Tyr-Gly-Gly-Phe-Val-Asp (SEQ ID NO: 10) Tyr-L-Ala-Gly-Phe-Val-Asp (SEQ ID NO: 11 )
Tyr-D-Ala-Gly-Phe-Val-Asp (SEQ ID NO: 12)
Tyr-Gly-Gly-Phe-Leu-Asn (SEQ ID NO: 13)
Tyr-L-Ala-Gly-Phe-Leu-Asn (SEQ ID NO: 14)
Tyr-D-Ala-Gly-Phe-Leu-Asn (SEQ ID NO: 15) Tyr-Gly-Gly-Phe-lle-Asn (SEQ ID NO: 16)
Tyr-L-Ala-Gly-Phe-lle-Asn (SEQ ID NO: 17)
Tyr-D-Ala-Gly-Phe-lle-Asn (SEQ ID NO: 18)
Tyr-Gly-Gly-Phe-Met-Asn (SEQ ID NO: 19)
Tyr-L-Ala-Gly-Phe-Met-Asn (SEQ ID NO: 20) Tyr-D-Ala-Gly-Phe-Met-Asn (SEQ ID NO: 21 )
Tyr-Gly-Gly-Phe-Val-Asn (SEQ ID NO: 22)
Tyr-L-Ala-Gly-Phe-Val-Asn (SEQ ID NO: 23)
Tyr-D-Ala-Gly-Phe-Val-Asn (SEQ ID NO: 24)
Tyr-Gly-Gly-Phe-Leu-Glu (SEQ ID NO: 25) Tyr-Ala-Gly-Phe-Leu-Glu (SEQ ID NO: 26)
Tyr-D-Ala-Gly-Phe-Leu-Glu (SEQ ID NO: 27)
Tyr-Gly-Gly-Phe-lle-Glu (SEQ ID NO: 28)
Tyr-L-Ala-Gly-Phe-lle-Glu (SEQ ID NO: 29)
Tyr-D-Ala-Gly-Phe-lle-Glu (SEQ ID NO: 30) Tyr-Gly-Gly-Phe-Met-Glu (SEQ ID NO: 31 )
Tyr-L-Ala-Gly-Phe-Met-Glu (SEQ ID NO: 32)
Tyr-D-Ala-Gly-Phe-Met-Glu (SEQ ID NO: 33)
Tyr-Gly-Gly-Phe-Val-Glu (SEQ ID NO: 34) Tyr-L-Ala-Gly-Phe-Val-Glu (SEQ ID NO: 35)
Tyr-D-Ala-Gly-Phe-Val-Glu (SEQ ID NO: 36)
Tyr-Gly-Gly-Phe-Leu-Gln (SEQ ID NO: 37)
Tyr-Ala-Gly-Phe-Leu-Gln (SEQ ID NO: 38) Tyr-D-Ala-Gly-Phe-Leu-Gln (SEQ ID NO: 39)
Tyr-Gly-Gly-Phe-lle-Gln (SEQ ID NO: 40)
Tyr-L-Ala-Gly-Phe-lle-Gln (SEQ ID NO: 41 )
Tyr-D-Ala-Gly-Phe-lle-Gln (SEQ ID NO: 42)
Tyr-Gly-Gly-Phe-Met-Gln (SEQ ID NO: 43) Tyr-L-Ala-Gly-Phe-Met-Gln (SEQ ID NO: 44)
Tyr-D-Ala-Gly-Phe-Met-Gln (SEQ ID NO: 45)
Tyr-Gly-Gly-Phe-Val-Gln (SEQ ID NO: 46)
Tyr-L-Ala-Gly-Phe-Val-Gln (SEQ ID NO: 47)
Tyr-D-Ala-Gly-Phe-Val-Gln (SEQ ID NO: 48) Tyr-D-Ala-Gly-Phe-Leu-Arg (SEQ ID NO: 49)
Tyr-D-Ala-Gly-Phe-Leu-Gly (SEQ ID NO: 50)
Tyr-D-Ala-Gly-Phe-Leu-Lys (SEQ ID NO: 51 )
Tyr-D-Ala-Gly-Phe-Leu-Thr (SEQ ID NO: 52)
Tyr-D-Ala-Gly-Phe-Leu-Ser (SEQ ID NO: 53) Tyr-D-Ala-Gly-Phe-Leu-Pro (SEQ ID NO: 54)
Tyr-D-Ala-Gly-Phe-Leu-Glu-Gly-Ala-Gly-Pro-Gly (SEQ ID NO: 55)
Tyr-Gly-Gly-Phe-Met (SEQ ID NO: 56)
Tyr-Gly-Gly-Phe-Leu (SEQ ID NO: 57)
8. The composition of claim 4, wherein an effective amount of the peptide of the general formula (I) is from about 0.00001 to 10 % by the weight of the composition.
9. The composition of claim 8, wherein an effective amount of the peptide of the general formula (I) is from about 0.0001 to 0.1 % by the weight of the composition.
10. The composition of claim 4, wherein the sunscreen agent is selected from the group consisting of zinc oxide, titanium dioxide, silica, iron oxide, dibenzoylmethane, 4-isopropyl dibenzoylmethane, 4-tert. butyl- 4'-methoxydibenzoylmethane (PARSOL 1789), dimethoxydibenzoylmethane, 4,4'-methoxy-t-butyldibenzoylmethane, ethyl p-aminobenzoic acid, octyldimethyl-p-aminobenzoic acid, 2- ethylhexyl N,N-dimethyl-p-aminobenzoate, p-aminobenzoic acid, octyl triazone (UVINUL T-150), dioctyl butamido triazone (UVASORB HEB), cinoxate, dioxybenzone, homosalate, menthylanthranilate, 2-ethylhexyl 2-cyano-3,3-diphenylacrylate (octocrylene, PARSOL 340), ethyl 2- cyano-3,3-diphenylacrylate, octyl methoxycinnamate, octyl salicylate, homomenthyl salicylate, TEA salicylate, trolamine salicylate, oxybenzone, padimate O, phenylbenzimidazole sulfonic acid, sulisobenzone, octyl methoxycinnamate (PARSOL MCX), ethoxyethyl methoxycinnamate, diethanolamine methoxycinnamate (PARSOL
Hydro), isoamyl methoxycinnamate, octyl methoxycinnamate, 2- ethylhexyl-p-methoxycinnamate (commercially available as PARSOL MCX), dromethzole trisiloxane, 4-methyl benzylidene camphor (PARSOL 5000), 3-benzylidene camphor, 3-(4-methylbenzylidene) camphor, camphor benzalkonium methosulfate, polyacrylamidomethyl benzylidene camphor, sulfo benzylidene camphor, sulphomethyl benzylidene camphor, therephthalidene dicamphor sulfonic acid, hydroxy methylphenyl benzotriazole, methylene bis- benzotriazoyltetramethylbutylphenol, 2-hydroxy-4-methoxybenzo- phenone, 2-phenylbenzimidazole-5-sulfonic acid, and 2-phenyl benzimidazole sulfonic acid.
11. The composition of claim 4, wherein an effective amount of a sunscreen agent is from about 1 % to about 20% by weight of the composition.
12. The composition of claim 4, wherein the pH of the composition is from about 5.0 to 7.5.
13.A method for the protection of a human skin against harmful effects of sunlight comprising administering to a subject in need thereof an effective amount of a composition which comprises a peptide of the general formula (I):
Tyr-Xi -GIy-PhIe-X2-X3-Y wherein
Xi is GIy or Ala;
X2 is independently Leu, Met, lie, or VaI; X3 is absent or independently Ala, Asp, Asn, GIu, GIn, Pro,
Arg, GIy, Lys, Thr, or Ser; Y is absent or a sequence of 1 to 5 amino acid residues.
14. The method of claim 13, wherein the peptide is selected from the group consisting of
Tyr-Gly-Gly-Phe-Leu-Asp (SEQ ID NO: 1 )
Tyr-L-Ala-Gly-Phe-Leu-Asp (SEQ ID NO: 2)
Tyr-D-Ala-Gly-Phe-Leu-Asp (SEQ ID NO: 3)
Tyr-Gly-Gly-Phe-lle-Asp (SEQ ID NO: 4) Tyr-L-Ala-Gly-Phe-lle-Asp (SEQ ID NO: 5)
Tyr-D-Ala-Gly-Phe-lle-Asp (SEQ ID NO: 6)
Tyr-Gly-Gly-Phe-Met-Asp (SEQ ID NO: 7)
Tyr-L-Ala-Gly-Phe-Met-Asp (SEQ ID NO: 8)
Tyr-D-Ala-Gly-Phe-Met-Asp (SEQ ID NO: 9) Tyr-Gly-Gly-Phe-Val-Asp (SEQ ID NO: 10)
Tyr-L-Ala-Gly-Phe-Val-Asp (SEQ ID NO: 11 )
Tyr-D-Ala-Gly-Phe-Val-Asp (SEQ ID NO: 12)
Tyr-Gly-Gly-Phe-Leu-Asn (SEQ ID NO: 13)
Tyr-L-Ala-Gly-Phe-Leu-Asn (SEQ ID NO: 14) Tyr-D-Ala-Gly-Phe-Leu-Asn (SEQ ID NO: 15)
Tyr-Gly-Gly-Phe-lle-Asn (SEQ ID NO: 16)
Tyr-L-Ala-Gly-Phe-lle-Asn (SEQ ID NO: 17)
Tyr-D-Ala-Gly-Phe-lle-Asn (SEQ ID NO: 18) Tyr-Gly-Gly-Phe-Met-Asn (SEQ ID NO: 19)
Tyr-L-Ala-Gly-Phe-Met-Asn (SEQ ID NO: 20)
Tyr-D-Ala-Gly-Phe-Met-Asn (SEQ ID NO: 21)
Tyr-Gly-Gly-Phe-Val-Asn (SEQ ID NO: 22) Tyr-L-Ala-Gly-Phe-Val-Asn (SEQ ID NO: 23)
Tyr-D-Ala-Gly-Phe-Val-Asn (SEQ ID NO: 24)
Tyr-Gly-Gly-Phe-Leu-Glu (SEQ ID NO: 25)
Tyr-Ala-Gly-Phe-Leu-Glu (SEQ ID NO: 26)
Tyr-D-Ala-Gly-Phe-Leu-Glu (SEQ ID NO: 27) Tyr-Gly-Gly-Phe-lle-Glu (SEQ ID NO: 28)
Tyr-L-Ala-Gly-Phe-lle-Glu (SEQ ID NO: 29)
Tyr-D-Ala-Gly-Phe-lle-Glu (SEQ ID NO: 30)
Tyr-Gly-Gly-Phe-Met-Glu (SEQ ID NO: 31)
Tyr-L-Ala-Gly-Phe-Met-Glu (SEQ ID NO: 32) Tyr-D-Ala-Gly-Phe-Met-Glu (SEQ ID NO: 33)
Tyr-Gly-Gly-Phe-Val-Glu (SEQ ID NO: 34)
Tyr-L-Ala-Gly-Phe-Val-Glu (SEQ ID NO: 35)
Tyr-D-Ala-Gly-Phe-Val-Glu (SEQ ID NO: 36)
Tyr-Gly-Gly-Phe-Leu-Gln (SEQ ID NO: 37) Tyr-Ala-Gly-Phe-Leu-Gln (SEQ ID NO: 38)
Tyr-D-Ala-Gly-Phe-Leu-Gln (SEQ ID NO: 39)
Tyr-Gly-Gly-Phe-lle-Gln (SEQ ID NO: 40)
Tyr-L-Ala-Gly-Phe-lle-Gln (SEQ ID NO: 41)
Tyr-D-Ala-Gly-Phe-lle-Gln (SEQ ID NO: 42) Tyr-Gly-Gly-Phe-Met-Gln (SEQ ID NO: 43)
Tyr-L-Ala-Gly-Phe-Met-Gln (SEQ ID NO: 44)
Tyr-D-Ala-Gly-Phe-Met-Gln (SEQ ID NO: 45)
Tyr-Gly-Gly-Phe-Val-Gln (SEQ ID NO: 46)
Tyr-L-Ala-Gly-Phe-Val-Gln (SEQ ID NO: 47) Tyr-D-Ala-Gly-Phe-Val-Gln (SEQ ID NO: 48)
Tyr-D-Ala-Gly-Phe-Leu-Arg (SEQ ID NO: 49)
Tyr-D-Ala-Gly-Phe-Leu-Gly (SEQ ID NO: 50)
Tyr-D-Ala-Gly-Phe-Leu-Lys (SEQ ID NO: 51) Tyr-D-Ala-Gly-Phe-Leu-Thr (SEQ ID NO: 52) Tyr-D-Ala-Gly-Phe-Leu-Ser (SEQ ID NO: 53) Tyr-D-Ala-Gly-Phe-Leu-Pro (SEQ ID NO: 54) Tyr-D-Ala-Gly-Phe-Leu-Glu-Gly-Ala-Gly-Pro-Gly (SEQ ID NO: 55) Tyr-Gly-Gly-Phe-Met (SEQ ID NO: 56)
Tyr-Gly-Gly-Phe-Leu (SEQ ID NO: 57)
15. The method of claim 13, wherein the harmful effect of sunlight is selected from the group consisting of erythema, sunburn, wrinkles, coarseness, mottled pigmentation, sallowness, laxity, eventually premalignant, and ultimately malignant neoplasms.
PCT/EP2008/055008 2008-04-24 2008-04-24 Photoprotective compositions containing peptides WO2009129855A1 (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103505377A (en) * 2013-09-11 2014-01-15 深圳市维琪医药研发有限公司 Polypeptide composition with skin activity

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5002933A (en) * 1987-06-19 1991-03-26 Vinogradov Valentin A Hexapeptide and medicinal preparation produced from it to treat erosive and ulcerative lesions of gastrointestinal tract
US20050036974A1 (en) * 2003-07-17 2005-02-17 L'oreal Beta-endorphin activity in cosmetics and dermatology
EP1892247A1 (en) * 2005-04-08 2008-02-27 Lipotec, S.A. Dermopharmaceutical or cosmetic composition comprising enkephalin-derived peptides for reducing and/or eliminating facial wrinkles
WO2008029064A2 (en) * 2006-09-06 2008-03-13 Thorel Jean-Noel Topical use of a peptide extract of soybean and/or of wheat as photoprotective agent

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5002933A (en) * 1987-06-19 1991-03-26 Vinogradov Valentin A Hexapeptide and medicinal preparation produced from it to treat erosive and ulcerative lesions of gastrointestinal tract
US20050036974A1 (en) * 2003-07-17 2005-02-17 L'oreal Beta-endorphin activity in cosmetics and dermatology
EP1892247A1 (en) * 2005-04-08 2008-02-27 Lipotec, S.A. Dermopharmaceutical or cosmetic composition comprising enkephalin-derived peptides for reducing and/or eliminating facial wrinkles
WO2008029064A2 (en) * 2006-09-06 2008-03-13 Thorel Jean-Noel Topical use of a peptide extract of soybean and/or of wheat as photoprotective agent

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103505377A (en) * 2013-09-11 2014-01-15 深圳市维琪医药研发有限公司 Polypeptide composition with skin activity
CN103505377B (en) * 2013-09-11 2015-06-03 深圳市维琪医药研发有限公司 Polypeptide composition with skin activity

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