WO1992020321A1 - Composition and method of enhancing sun tanning - Google Patents

Composition and method of enhancing sun tanning Download PDF

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Publication number
WO1992020321A1
WO1992020321A1 PCT/GB1992/000877 GB9200877W WO9220321A1 WO 1992020321 A1 WO1992020321 A1 WO 1992020321A1 GB 9200877 W GB9200877 W GB 9200877W WO 9220321 A1 WO9220321 A1 WO 9220321A1
Authority
WO
WIPO (PCT)
Prior art keywords
pseudocatalase
composition
skin
tanning
bicarbonate
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.)
Ceased
Application number
PCT/GB1992/000877
Other languages
French (fr)
Inventor
John Martin Wood
Karin Uta Schallreuter
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.)
Stiefel Research Australia Pty Ltd
Stiefel Laboratories Inc
Original Assignee
Stiefel Research Australia Pty Ltd
Stiefel Laboratories Inc
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 Stiefel Research Australia Pty Ltd, Stiefel Laboratories Inc filed Critical Stiefel Research Australia Pty Ltd
Priority to DE69213231T priority Critical patent/DE69213231T2/en
Priority to EP92910468A priority patent/EP0584178B1/en
Priority to US08/150,015 priority patent/US5443819A/en
Priority to AU17936/92A priority patent/AU650343B2/en
Priority to JP4510486A priority patent/JPH06510274A/en
Publication of WO1992020321A1 publication Critical patent/WO1992020321A1/en
Anticipated expiration legal-status Critical
Priority to GR960402737T priority patent/GR3021364T3/en
Priority to HK198396A priority patent/HK198396A/en
Ceased legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/66Enzymes
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier 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
    • A61Q17/04Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/04Preparations for care of the skin for chemically tanning the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/58Metal complex; Coordination compounds

Definitions

  • a pseudocatalase in the manufacture of a topical composition for the enhancement of tanning of skin, especially fair skin, on exposure to sunlight or UVB light.
  • the invention provides a topical sunscreen composition
  • a topical sunscreen composition comprising a pseudocatalase, a sunscreen agent and a physiologically acceptable topical vehicle therefor.
  • the invention provides a pseudocatalase for use in the enhancement of tanning of skin, especially fair skin, on exposure to sunlight or UVB light.
  • the invention provides a method of enhancing tanning of skin, especially fair skin, which comprises applying to the skin an effective amount of a pseudocatalase.
  • the invention provides use of a pseudocatalase to enhance tanning of skin on exposure to sunlight or UVB light.
  • the pseudocatalase can be any physiologically acceptable compound which catalyzes the dis utation of -3-
  • Mn(II) bicarbonate are already known to be pseudocatalases and others can be determined by simple screening tests.
  • the presently preferred pseudocatalases are transition metal co-ordination complexes in which the inductive effect of the electron acceptor ligand enhances the redox effect of the metal on hydrogen peroxide dismutation.
  • the metal will be Cu(I) , Fe(II) or, especially Mn(II) and the ligand will be bicarbonate. It is especially preferred that the pseudocatalase is Mn(II) bicarbonate complex. Said complex readily can be prepared by contacting manganous chloride with excess bicarbonate in aqueous solution.
  • the pseudocatalase is formulated in a topical vehicle for use.
  • the vehicle comprises a hydrophilic cream to which an aqueous solution or suspension of the pseudocatalase is added to form a cream or lotion.
  • the vehicle can be a bath oil although any other compatible topical vehicle can be used to provide a topical composition.
  • the composition will contain a sunscreen agent, and other components such as emollients, perfumes etc conventionally used in sunscreen preparations.
  • the composition can contain calcium ions, suitably added as calcium chloride, usually in a concentration of 5 to 20 mmol.
  • any conventional sunscreen agent such as Parsol MCX, or other component can be used.
  • Manganous chloride (380 mg) was added to a solution of sodium bicarbonate (2.3 g) in purified water (3.0 ml) at ambient temperature. The mixture was allowed to stand until the evolution of gas had ceased. The resultant pinkish brown liquid was mixed with a hydrophilic cream (Neribase) to provide a white cream.
  • Neribase is a cream vehicle containing Macrogol stearate 2000; stearic alcohol; liquid paraffin; white soft paraffin; polyacryiic acid; sodium hydroxide; disodium EDTA (i.e. ethylenediaminetetraacetic acid disodium salt); methyl and propyl Paraben (i.e. 4-hydroxybenzoic acid methyl and propyl esters) ; and water.
  • disodium EDTA i.e. ethylenediaminetetraacetic acid disodium salt
  • methyl and propyl Paraben i.e. 4-hydroxybenzoic acid methyl and propyl esters
  • the cream was applied to test skin areas of healthy volunteers having skin type II or III and, after a period of 20, 45 or 60 minutes, the treated skin exposed to UVB light for 10 to 20 seconds.
  • the UVB source was a Saalmann UV-Test machine and the doses were 0.06, 0.05, 0.04, 0.03, 0.02 mJ/cirr (10 seconds) and 0.18, 0.15, 0.12, 0.09, 0.06 mJ/cirr (30 seconds) .
  • the degree of erythema/tanning of the treated area and untreated area was determined by observation after 24 and 72 hours post-irradiation.
  • T j time between application and UVB irradiation
  • T time of UVB irradiation
  • Example 1 The test of Example 1 was repeated using creams tc which calcium chloride had been added to provide 5 mmole or 10 mmole calcium ion content. The results are set forth in Tables II and III below. -6-
  • T ⁇ time between application and UVB irradiation time of UVB irradiation -7-

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Cosmetics (AREA)
  • Treatment And Processing Of Natural Fur Or Leather (AREA)
  • Reinforced Plastic Materials (AREA)
  • Radiation-Therapy Devices (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Sun tanning, especially of fair skin, is enhanced by topical application of a pseudocatalase prior to exposure to sunlight or UVB light. The preferred pseudocatalases are transition metal co-ordination complexes, especially manganese (II) bicarbonate.

Description

-2-
causing an undesirable increase in hydroxyl ion concentration unless catalase or some other competing mechanism removes peroxide ion. Thus, the presence of a pseudocatalase is believed to allow sufficient UVB exposure for superoxide anion radical formation to promote pigmentation in catalase deficient areas without burning or other cell damage.
According to a first aspect of the present invention, there is provided the use of a pseudocatalase in the manufacture of a topical composition for the enhancement of tanning of skin, especially fair skin, on exposure to sunlight or UVB light.
In a second aspect, the invention provides a topical sunscreen composition comprising a pseudocatalase, a sunscreen agent and a physiologically acceptable topical vehicle therefor.
In a third aspect, the invention provides a pseudocatalase for use in the enhancement of tanning of skin, especially fair skin, on exposure to sunlight or UVB light.
In a fourth aspect, the invention provides a method of enhancing tanning of skin, especially fair skin, which comprises applying to the skin an effective amount of a pseudocatalase.
In a fifth aspect, the invention provides use of a pseudocatalase to enhance tanning of skin on exposure to sunlight or UVB light.
The pseudocatalase can be any physiologically acceptable compound which catalyzes the dis utation of -3-
hydrogen peroxide. Some compounds such as Mn(II) bicarbonate are already known to be pseudocatalases and others can be determined by simple screening tests.
The presently preferred pseudocatalases are transition metal co-ordination complexes in which the inductive effect of the electron acceptor ligand enhances the redox effect of the metal on hydrogen peroxide dismutation. Usually, the metal will be Cu(I) , Fe(II) or, especially Mn(II) and the ligand will be bicarbonate. It is especially preferred that the pseudocatalase is Mn(II) bicarbonate complex. Said complex readily can be prepared by contacting manganous chloride with excess bicarbonate in aqueous solution.
The pseudocatalase is formulated in a topical vehicle for use. Conveniently, the vehicle comprises a hydrophilic cream to which an aqueous solution or suspension of the pseudocatalase is added to form a cream or lotion. Alternatively, the vehicle can be a bath oil although any other compatible topical vehicle can be used to provide a topical composition.
Usually, the composition will contain a sunscreen agent, and other components such as emollients, perfumes etc conventionally used in sunscreen preparations. In particular, the composition can contain calcium ions, suitably added as calcium chloride, usually in a concentration of 5 to 20 mmol. Subject to compatibility with the pseudocatalase and superoxide anion, any conventional sunscreen agent, such as Parsol MCX, or other component can be used.
The invention is illustrated in the following non- limiting Examples. -4 -
Example 1
Manganous chloride (380 mg) was added to a solution of sodium bicarbonate (2.3 g) in purified water (3.0 ml) at ambient temperature. The mixture was allowed to stand until the evolution of gas had ceased. The resultant pinkish brown liquid was mixed with a hydrophilic cream (Neribase) to provide a white cream.
Neribase is a cream vehicle containing Macrogol stearate 2000; stearic alcohol; liquid paraffin; white soft paraffin; polyacryiic acid; sodium hydroxide; disodium EDTA (i.e. ethylenediaminetetraacetic acid disodium salt); methyl and propyl Paraben (i.e. 4-hydroxybenzoic acid methyl and propyl esters) ; and water.
The cream was applied to test skin areas of healthy volunteers having skin type II or III and, after a period of 20, 45 or 60 minutes, the treated skin exposed to UVB light for 10 to 20 seconds. The UVB source was a Saalmann UV-Test machine and the doses were 0.06, 0.05, 0.04, 0.03, 0.02 mJ/cirr (10 seconds) and 0.18, 0.15, 0.12, 0.09, 0.06 mJ/cirr (30 seconds) . The degree of erythema/tanning of the treated area and untreated area was determined by observation after 24 and 72 hours post-irradiation.
The results are set forth in Table I below. Tha erythema increase is indicated on the scale +, ++ and +++ with ++ and +++ presenting a darker tan. -5-
TABLE I
Sex/ Skin T 24 h treated/ 72 h treated/ aσe type min sec control side control side
20 20 20 20 20 20 20
20
Figure imgf000006_0001
20
Figure imgf000006_0002
+ - +++ grade of erythema / tanning
Tj = time between application and UVB irradiation T = time of UVB irradiation
Example 2
The test of Example 1 was repeated using creams tc which calcium chloride had been added to provide 5 mmole or 10 mmole calcium ion content. The results are set forth in Tables II and III below. -6-
TABLE II
(5 mmol Ca2+)
T2 24 h treated/ 72 h treated/ sec control side control side
Figure imgf000007_0001
Figure imgf000007_0002
+ - +++ grade of erythema / tanning
T} = time between application and UVB irradiation time of UVB irradiation -7-
TABLE III
Figure imgf000008_0001
+ - +++ : grade of erythema / tanning τi = time between application and UVB irradiation T2 = time of UVB irradiation

Claims

-8-CLAIMS
1. A topical composition comprising a pseudocatalase, a sunscreen agent and a physiologically acceptable topical vehicle therefor.
2. A composition as claimed in Claim 1, which is free of calcium ions.
3. A composition as claimed in Claim 1, which contains 5 to 20 mmol calcium ions.
4. A topical composition as claimed in Claim 1, wherein the pseudocatalase is a transition metal co-ordination complex.
5. A composition as claimed in Claim 4, wherein the pseudocatalase is a Cu(I) , Fe(II) or Mn(II) co-ordination complex.
6. A composition as claimed in Claim 4, wherein the ligand of said co-ordination complex is bicarbonate.
7. A composition as claimed in Claim 6, wherein the pseudocatalase is a Mn(II)-bicarbonate complex.
8. A composition as claimed in Claim 7, wherein the
Mn(II)-bicarbonate complex has been obtained by contacting manganous chloride with excess sodium bicarbonate in aqueous solution.
9. A method of enhancing tanning of skin which comprises applying to the skin an effective amount of a pseudocatalase. -9-
10. A pseudocatalase for use in the enhancement of tanning of skin on exposure to sunlight or UVB light.
11. The use of a pseudocatalase in the manufacture of a topical composition for the enhancement of tanning skin on exposure to sunlight or UVB light.
12. Use of a pseudocatalase to enhance tanning of skin on exposure to sunlight or UVB light.
PCT/GB1992/000877 1991-05-15 1992-05-15 Composition and method of enhancing sun tanning Ceased WO1992020321A1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
DE69213231T DE69213231T2 (en) 1991-05-15 1992-05-15 COMPOSITION AND METHOD FOR REINFORCING TAN
EP92910468A EP0584178B1 (en) 1991-05-15 1992-05-15 Composition and method of enhancing sun tanning
US08/150,015 US5443819A (en) 1991-05-15 1992-05-15 Composition and method of enhancing sun tanning
AU17936/92A AU650343B2 (en) 1991-05-15 1992-05-15 Composition and method of enhancing sun tanning
JP4510486A JPH06510274A (en) 1991-05-15 1992-05-15 Compositions and methods for enhancing sun-induced discoloration
GR960402737T GR3021364T3 (en) 1991-05-15 1996-10-16 Composition and method of enhancing sun tanning.
HK198396A HK198396A (en) 1991-05-15 1996-10-31 Composition and method of enhancing sun tanning

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9110651.8 1991-05-15
GB919110651A GB9110651D0 (en) 1991-05-15 1991-05-15 Composition and method of enhancing sun tanning

Publications (1)

Publication Number Publication Date
WO1992020321A1 true WO1992020321A1 (en) 1992-11-26

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Country Status (18)

Country Link
US (1) US5443819A (en)
EP (1) EP0584178B1 (en)
JP (1) JPH06510274A (en)
AT (1) ATE141785T1 (en)
AU (1) AU650343B2 (en)
CA (1) CA2102515A1 (en)
DE (1) DE69213231T2 (en)
ES (1) ES2091467T3 (en)
GB (1) GB9110651D0 (en)
GR (1) GR3021364T3 (en)
HK (1) HK198396A (en)
IE (1) IE69260B1 (en)
IL (1) IL101873A (en)
MY (1) MY108163A (en)
NZ (1) NZ242749A (en)
TW (1) TW201693B (en)
WO (1) WO1992020321A1 (en)
ZA (1) ZA923560B (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2307175A (en) * 1995-11-14 1997-05-21 Steifel Lab Inc Topical composition comprising a transition metal and bicarbonate ions, particularly for the promotion of pigmentation
FR2814945A1 (en) * 2000-10-09 2002-04-12 Oreal CANITIY TREATMENT PROCESS
US6953486B2 (en) 2000-10-09 2005-10-11 L'oreal Dyeing composition, method for obtaining the same and use for coloring the skin and/or keratinous fibres
US7704285B2 (en) 2002-11-29 2010-04-27 L'oreal S.A. Composition for coloring a keratin material, comprising at least two components, and coloring processes

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2287899A1 (en) * 1974-10-15 1976-05-14 Oreal NEW ENZYME-BASED COSMETIC COMPOSITIONS
US4349536A (en) * 1980-03-11 1982-09-14 Hausler Kenneth J Method of promoting suntan using a cream containing zinc and copper salts
EP0155344A2 (en) * 1983-08-02 1985-09-25 Blendax GmbH Skin treatment composition
US4806344A (en) * 1987-01-05 1989-02-21 Gaskin Frances C Sun protectant composition and method
EP0380335A2 (en) * 1989-01-27 1990-08-01 Lancaster Societe Anonyme Monegasque Sun tan accelerator compositions
EP0424033A2 (en) * 1989-10-19 1991-04-24 Pola Chemical Industries Inc External skin preparation

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02108612A (en) * 1988-10-19 1990-04-20 Shizen:Kk Divalent and trivalent complex iron salt-compounded cosmetic

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2287899A1 (en) * 1974-10-15 1976-05-14 Oreal NEW ENZYME-BASED COSMETIC COMPOSITIONS
US4349536A (en) * 1980-03-11 1982-09-14 Hausler Kenneth J Method of promoting suntan using a cream containing zinc and copper salts
EP0155344A2 (en) * 1983-08-02 1985-09-25 Blendax GmbH Skin treatment composition
US4806344A (en) * 1987-01-05 1989-02-21 Gaskin Frances C Sun protectant composition and method
EP0380335A2 (en) * 1989-01-27 1990-08-01 Lancaster Societe Anonyme Monegasque Sun tan accelerator compositions
EP0424033A2 (en) * 1989-10-19 1991-04-24 Pola Chemical Industries Inc External skin preparation

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Patent Abstracts of Japan, vol. 14, no. 314 (C-737)[4257], 5 July 1990, & JP,A,2108612 (SHIZEN K.K.) 20 April 1990, see the abstract *
STN File Supplier, Karlsruhe DE, File Chemical Abstract, & CA, vol. 114, no. 21, 27 May 1991, (Columbus, Ohio, US), Y. KONO: "Manganese calatase", see abstract no. 202133d, & KASSEI SANSO, FURI RAJIKARU, 1990, 2(1), 18-26, see the abstract *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2307175A (en) * 1995-11-14 1997-05-21 Steifel Lab Inc Topical composition comprising a transition metal and bicarbonate ions, particularly for the promotion of pigmentation
WO1997017943A1 (en) * 1995-11-14 1997-05-22 Stiefel Laboratories, Inc. Improved pseudocatalase composition
US5895642A (en) * 1995-11-14 1999-04-20 Stiefel Laboratories, Inc. Pseudocatalase activity
FR2814945A1 (en) * 2000-10-09 2002-04-12 Oreal CANITIY TREATMENT PROCESS
WO2002030372A1 (en) * 2000-10-09 2002-04-18 L'oreal Method for treating whitening of hair
US6953486B2 (en) 2000-10-09 2005-10-11 L'oreal Dyeing composition, method for obtaining the same and use for coloring the skin and/or keratinous fibres
US7704285B2 (en) 2002-11-29 2010-04-27 L'oreal S.A. Composition for coloring a keratin material, comprising at least two components, and coloring processes

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DE69213231T2 (en) 1997-02-20
ATE141785T1 (en) 1996-09-15
AU1793692A (en) 1992-12-30
IL101873A0 (en) 1992-12-30
US5443819A (en) 1995-08-22
JPH06510274A (en) 1994-11-17
GB9110651D0 (en) 1991-07-03
AU650343B2 (en) 1994-06-16
MY108163A (en) 1996-08-30
GR3021364T3 (en) 1997-01-31
HK198396A (en) 1996-11-08
TW201693B (en) 1993-03-11
IE69260B1 (en) 1996-08-21
EP0584178A1 (en) 1994-03-02
EP0584178B1 (en) 1996-08-28
CA2102515A1 (en) 1992-11-16
DE69213231D1 (en) 1996-10-02
IE921558A1 (en) 1992-11-18
ES2091467T3 (en) 1996-11-01
IL101873A (en) 1996-08-04
ZA923560B (en) 1993-04-28
NZ242749A (en) 1994-12-22

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