EP0914089A1 - Utilisation de composes antioxydants lipophiles pour empecher les reactions oxydatives induites par les retinoides et vehiculees par les uva - Google Patents

Utilisation de composes antioxydants lipophiles pour empecher les reactions oxydatives induites par les retinoides et vehiculees par les uva

Info

Publication number
EP0914089A1
EP0914089A1 EP97951582A EP97951582A EP0914089A1 EP 0914089 A1 EP0914089 A1 EP 0914089A1 EP 97951582 A EP97951582 A EP 97951582A EP 97951582 A EP97951582 A EP 97951582A EP 0914089 A1 EP0914089 A1 EP 0914089A1
Authority
EP
European Patent Office
Prior art keywords
retinoid
lipid peroxidation
uva
induced
skin
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP97951582A
Other languages
German (de)
English (en)
Inventor
Jeffrey C. Geesin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Johnson and Johnson Consumer Inc
Original Assignee
Johnson and Johnson Consumer Companies LLC
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 Johnson and Johnson Consumer Companies LLC filed Critical Johnson and Johnson Consumer Companies LLC
Publication of EP0914089A1 publication Critical patent/EP0914089A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/004—Aftersun 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
    • A61K8/67—Vitamins
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/522—Antioxidants; Radical scavengers

Definitions

  • the present invention relates to the protection of skin from the oxidative effects of ultraviolet (UV) A radiation that are induced by retinoid use.
  • the present invention relates to means of topically applying a retinoid to skin that reduces or eliminates skin damage caused by retinoid induced, UVA- mediated oxidative effects.
  • Retinoids such as, retinoic acid (also known as vitamin A acid or tretinoin) , retinol, and retinol palmitate, are known to have beneficial effects on the skin. For example, they have been used both orally and topically to treat acne.
  • Retinoids have been shown to be able to act as antioxidants at high concentrations, protecting the skin from sunlight and preventing the induction of lipid peroxidation initiated by the use of ascorbic acid and iron [Das et al., J Neurochem (1989) 52:585-588; Khettab et al., Biochimie (1988) 70:1709-1713; and Geesin et al. Arch Biochem Biophys (1990) 278:350-355].
  • UV radiation from the sun produces its acute and chronic effects on skin involves the production of reactive oxygen species, which cause pathology by a number of different mechanisms including lipid peroxidation production [Shea et al . , "Nonionizing radiation and the skin.” In: Physiology, Biochemistry, and Molecular Biology of the Skin . 1991. LA Goldsmith, ed. Oxford University Press:New York. vol. 2, pp. 910-927]. Indeed, the production of free radicals and lipid peroxidation has been associated with characteristic changes associated with aging in many tissues including the skin [Machlin, et al., FASEB J (1987) 1:441-445; Emerit, I, "Free radicals and aging in skin.” In: Free Radicals and Aging.
  • retinoids have also been reported to produce undesirable side effects.
  • Retinoids have been reported to reduce the exposure time for individuals to produce UV-mediated erythema resulting in increased sensitivity to sunburn [Szaniawska et al., Neoplasm (1988) 35:191-195; Collins et al., J Am Acad Dermatol (1986) 14:274; Ferguson et al., Pharmac Ther (1989) 40:123-135; and Auffret et al . , J Am Acad Dermatol (1990) 23:321-322].
  • the present invention relates to a method of topically applying a retinoid to mammalian skin which reduces or eliminates retinoid induced, UVA-mediated oxidative damage to the skin.
  • the method comprises topically applying to the skin a composition comprising a safe and effective amount of a retinoid and a safe and effective amount of a lipophilic antioxidant.
  • Figure 1 shows the effect of different culture plates on the production of lipid peroxidation by human dermal fibroblasts exposed to solar simulated light.
  • Cells were exposed to solar simulated light through the covers on Corning 75 cm 2 flasks or through Costar 100 mm tissue culture dishes with or without the covers. Triplicate cultures were exposed to increasing numbers of MED using the solar simulator arrangement of lamps.
  • Figure 2 shows the spectral dose distribution of light sources with different culture materials.
  • the spectral dose distribution is presented for the three cell culture conditions identified in the lipid peroxidation measurements described previously (see Figure 1) using the solar simulator arrangement of lamps.
  • Figure 3 shows the spectral irradiance of F40 350BL lamps.
  • Figure 4 shows the absorbance spectra of Schott filters. The absorbance of various WG filters was determined and is shown.
  • Figure 5 shows the spectral dose distribution produced with the Schott Filters described in Figure 4.
  • Figure 6 show the difference spectra produced using the Sylvania F40 350BL fluorescent lamps in combination with the Schott Filters described in Figures 4 and 5. These spectra represent the differences in spectra produced when comparing one filter to the next in the series.
  • Figure 7 shows lipid peroxidation produced in human dermal fibroblasts (HSF) and Swiss 3T3 cells (S3T3) in the presence or absence of the Schott filters described in Figures 4-6.
  • Figure 8 shows lipid peroxidation action spectrum for human dermal fibroblasts (HSF) and Swiss 3T3 Mouse Fibroblasts (S3T3) . These action spectra were determined using the information from Figures 6 and 7.
  • Figure 9 shows difference spectra produced using the Sylvania F40 350BL fluorescent lamps as described in Figure 6. This presentation highlights selected wavelengths (290-310nm) from Figure 6.
  • Figure 10 shows the spectral irradiance of Westinghouse FS40 Sunlamps alone.
  • Figure 11 shows the effect of exposure to Westinghouse FS40 Sunlamps on the production of lipid peroxidation in human dermal fibroblasts. Triplicate cultures were exposed to increasing number of MED.
  • Figure 12 shows the effect of retinoids on UVA-induced lipid peroxidation.
  • Swiss 3T3 mouse fibroblasts (S3T3) (A) and human dermal fibroblasts (B) were exposed to 60 joules/cm 2 UVA using Sylvania F40 350BL lamps.
  • Figure 13 shows dose and wavelength dependence for the effect of retinoic acid on UV-induced lipid peroxidation. Triplicate cultures were irradiated for the indicated number of MED using the solar simulator arrangement of lamps or for the indicated levels of joules/cm 2 UVA in the presence of 100 mM retinoic acid.
  • Figure 15 shows the effect of retinoids on background levels of lipid peroxidation in Swiss 3T3 cells. Triplicate cultures were treated with the indicated concentrations and types of retinoids and maintained either under aluminum foil away from the lamps (NO UV) or under the lamps (FOIL) .
  • Figure 16 shows the lipid peroxidation action spectrum for Swiss 3T3 cells treated with retinoic acid.
  • Figure 17 shows the absorbance spectrum for a 50 ⁇ M solution of all-trans retinoic acid in methanol.
  • Figure 18 shows the effect of butylated hydroxyanisole, butylated hydroxytoluene, and ascorbic acid (asborbate) on the synergistic effect of retinoic acid and UVA on the production of lipid peroxidation in Swiss 3T3 cells.
  • the present invention is directed to methods of topically applying to the skin a retinoid while reducing or eliminating skin damage caused by retinoid induced,
  • a composition that contains an effective amount of a retinoid and an effective amount of a lipophilic antioxidant that reduces and/or eliminates retinoid induced, UVA-mediated oxidative damage.
  • Retinoid induced UVA-mediated oxidative effects include, but are not limited to, lipid peroxidation and the products produced by lipid peroxidation such as cross-linking agents.
  • Lipophilic antioxidants have been found to be effective at preventing skin damage caused by retinoid induced, UVA-mediated oxidative effects.
  • Preferred lipophilic antioxidants include, but are not limited to, ascorbyl-6-palmitate, butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) .
  • Ascorbyl palmitate has previously been shown to be ineffective at preventing UVB induced wrinkling in hairless mice [Bissett et al., Photodermatol Photoimmunol Photomed (1990) 7:56-62], however it has been shown to protect endothelial cells from the cytotoxic effects of products of lipid peroxidation [Kaneko et al., Arch Biochem Biophys (1993) 304:176-180]. No examination of the effect of ascorbyl-palmitate on UVA-mediated events has been reported. BHA has also been shown to be effective at preventing UVC-induced lipid peroxidation in liposomes [Pelle et al., Arch Biochem Biophys (1990) 283:234-240].
  • BHA has been found to be effective at preventing UVB- or PUVA-induced ornithine decarboxylase activity (associated with tumor formation) [Kono et al., J Dermatol (1992) 19:389-392; Black et al., Photochem Photobiol (1986) 43:403-408], however, BHA had no effect on UVB-induced photocarcinogenesis [Black et al., Photochem Photobiol (1986) 43:403-408]. No results concerning the effects of BHA on other UVA-mediated events have been reported.
  • BHT has been shown to be effective in preventing UVA- [Bose et al., Radiat Res (1993) 133:340-344] and UVC- [Pelle et al.. Arch Biochem Biophys (1990) 283:234-240] induced lipid peroxidation in liposomes. No evidence of activity of BHT against UVA-mediated oxidative effects in animals or cultured cells has been reported.
  • the retinoid composition containing a lipophilic antioxidant is applied topically to the skin to protect it from retinoid induced, UVA- mediated oxidative effects.
  • the amount of retinoid used in the topical compositions and methods of the present invention can vary within significant limits depending on the therapeutic use for which the retinoid composition will be applied to the skin.
  • the retinoid will be present from about 0.001 to about 3.0 percent by weight, more preferably from about 0.025 to about 0.5 percent by weight.
  • the amount of the lipophilic antioxidant present in the retinoid compositions and applied to the skin cells may vary so long as a sufficient amount of the antioxidant is present to reduce or eliminate retinoid induced, UVA- mediated oxidative damage, including lipid peroxidation, to the skin.
  • the antioxidant is present in the composition from about .0001 % to about 10 % (w/w) , more preferably from about .01 % to about 1 %, and more preferably still from about .1 % to about .5 %.
  • the retinoid compositions of the present invention may be made into a variety of product types.
  • the compositions can be in solid, liquid or aerosol form so long as they are suitable for topical administration.
  • the compositions can be formulated into a liposomal formulation, an emollient, a liquid, a cream, a gel, an ointment, a microemulsion, or a solution.
  • Other typical skin care agents and additives that assist in the purpose of the present invention or that are conventionally used in topical cosmetics or medical compositions may also be included in the retinoid compositions used in the present invention.
  • Various vitamins may also be included in the photoprotective compositions of the present invention. Examples of such vitamins include, but are not limited to. Vitamin A and derivatives thereof. Vitamin B 2 , biotin, pantothenic, Vitamin D, Vitamin E and combinations thereof.
  • S3T3 mouse Swiss 3T3
  • HSF human dermal fibroblasts
  • Example 1 Effect of culture materials on the production of lipid peroxidation
  • neonatal human dermal fibroblasts were irradiated using a combination of Sylvania F40 350BL lamps (98% UVA) and Westinghouse FS40 Sunlamps (approximately 50% UVA, 50% UVB) to simulate the normal solar spectrum.
  • Neonatal human dermal fibroblast cultures were grown as described above in Corning 75 cm 2 tissue culture flasks or in 100 mm Costar culture dishes. Cultures were then irradiated through the use of a solar simulator arrangement of bulbs with a 6:5 mix of Sylvania F40 350BL lamps and Westinghouse FS40 Sunlamps (50% UVA, 50% UVB) .
  • the action spectra for the phenomenon was determined as described above. Briefly, using the Schott filters, the levels of lipid peroxidation were determined in Swiss 3T3 cells in the presence of retinoic acid, retinol or retinol acetate ( Figure 14) compared to UVA alone ( Figure 14 and Figure 7) . Treatment of S3T3 cells with retinoids produced a similar, but not identical, pattern for all the retinoids tested.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Cosmetics (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)

Abstract

Cette invention se rapporte à des moyens et à des procédés pour appliquer topiquement sur la peau d'un mammifère un rétinoïde qui réduit ou élimine les effets oxydatifs induits par les rétinoïdes et véhiculés par les ultra-violets A. Ce procédé consiste à appliquer topiquement sur la peau une composition de rétinoïde qui contient une quantité efficace de rétinoïde et une quantité efficace d'un antioxydant lipophile.
EP97951582A 1996-12-10 1997-12-08 Utilisation de composes antioxydants lipophiles pour empecher les reactions oxydatives induites par les retinoides et vehiculees par les uva Withdrawn EP0914089A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US76278496A 1996-12-10 1996-12-10
US762784 1996-12-10
PCT/US1997/022441 WO1998025587A1 (fr) 1996-12-10 1997-12-08 Utilisation de composes antioxydants lipophiles pour empecher les reactions oxydatives induites par les retinoides et vehiculees par les uva

Publications (1)

Publication Number Publication Date
EP0914089A1 true EP0914089A1 (fr) 1999-05-12

Family

ID=25066031

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97951582A Withdrawn EP0914089A1 (fr) 1996-12-10 1997-12-08 Utilisation de composes antioxydants lipophiles pour empecher les reactions oxydatives induites par les retinoides et vehiculees par les uva

Country Status (11)

Country Link
EP (1) EP0914089A1 (fr)
JP (1) JP2000505816A (fr)
KR (1) KR19990082411A (fr)
CN (1) CN1215328A (fr)
AU (1) AU5518898A (fr)
BR (1) BR9707630A (fr)
CA (1) CA2246306A1 (fr)
ID (1) ID18520A (fr)
IL (1) IL125700A0 (fr)
IN (1) IN187969B (fr)
WO (1) WO1998025587A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2801790B1 (fr) * 1999-12-03 2002-01-18 Fabre Pierre Cosmetique Association retinal et aldehydes, composition cosmetique la contenant, a titre de medicament l'association retinal et aldehydes, et procede de preparation de cette association
DE10012151A1 (de) * 2000-03-13 2001-09-27 Gsf Forschungszentrum Umwelt Mittel zur Behandlung von Erkrankungen des Tracheo-Brochialtraktes, insbesondere der COPD
JP5728152B2 (ja) * 2008-07-07 2015-06-03 株式会社ファンケル 乾燥リポソーム製剤

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3372843D1 (en) * 1982-05-15 1987-09-10 Beecham Group Plc Skin treatment compositions
JP3280712B2 (ja) * 1992-07-13 2002-05-13 株式会社資生堂 皮膚外用剤
FR2718021B1 (fr) * 1994-04-05 1996-06-28 Fabre Pierre Cosmetique Composition topique à base de rétinal.
US6461622B2 (en) * 1994-09-07 2002-10-08 Johnson & Johnson Consumer Companies, Inc. Topical compositions
US5747010A (en) * 1996-06-12 1998-05-05 Johnson & Johnson Consumer Products, Inc. Photoprotective lipophilic antioxidant compounds and their use to prevent UVA-mediated lipid peroxidation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9825587A1 *

Also Published As

Publication number Publication date
IN187969B (fr) 2002-08-03
CA2246306A1 (fr) 1998-06-18
JP2000505816A (ja) 2000-05-16
ID18520A (id) 1998-04-16
IL125700A0 (en) 1999-04-11
CN1215328A (zh) 1999-04-28
KR19990082411A (ko) 1999-11-25
BR9707630A (pt) 1999-07-27
AU5518898A (en) 1998-07-03
WO1998025587A1 (fr) 1998-06-18

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