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Tyrosinase inhibitors

a technology of tyrosinase inhibitors and inhibitors, which is applied in the field of new compounds and cosmetic formulations, can solve the problems of certain side effects and individuals with sensitivity

Inactive Publication Date: 2015-06-25
AVON PROD INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0007]In accordance with the foregoing objectives and others, the present invention provides compounds and cosmetic formulations thereof that improve one or more signs of dermatological aging and / or skin depigmentation when topically applied to human integuments (skin, lips, nails, hair, etc.), particularly skin. The invention ideally provides compositions and methods for reducing unwanted pigmentation in human skin. The compositions and methods may treat hyperpigmentation conditions, including those associated with UV damage and chronological aging, including without limitation treating, ameliorating, diminishing the appearance of, or preventing age spots, liver spots, freckles, and the like. The compositions and methods are also useful for reducing otherwise unwanted pigmentation, including overall lightening of the skin.
[0008]In one aspect of the invention, cosmetic compositions are provided for improving the aesthetic appearance of human skin comprising a cosmetically acceptable vehicle, and an effective amount of a diazothione active agent that reduces pigmentation in keratinous biological substrates, including the skin. The cosmetic composition may comprise a compound according to formula I(a):
[0016]In a related aspect, cosmetic compositions are provided for improving the aesthetic appearance of human skin comprising a cosmetically acceptable vehicle, and an effective amount of a diazothioether active agent that reduces pigmentation in keratinous biological substrates, including the skin. The cosmetic composition may comprise a compound according to formula II(a):
[0019]It is a further object of the present disclosure to provide methods comprising topically applying such depigmenting compositions to skin. The composition may be applied once or twice daily, or more frequently, and the treatment regimen may last for as long as required to obtain the desired visible reduction in pigmentation, which may be, for example, one week, four weeks, eight weeks, twelve weeks or longer. The compositions may be applied to human keratinous surfaces, such as skin, to treat, ameliorate, diminish, or prevent, or delay the onset of one or more of dark complexion, pigmented skin discoloration, pigmented birthmarks, hyperpigmentation, post-inflammatory hyperpigmentation, post-injury hyperpigmentation, freckles, age spots, liver spots, sun damage, tans, pigmented acne marks, scars, melasma, cholasma, after-burn scars, nail stains, yellowing of skin, or dark circles under eye.

Problems solved by technology

While these lightening agents do work, they may exhibit in some individuals having sensitivity thereto certain side effects.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

Mushroom Tyrosinase Assay

[0107]Mushroom tyrosinase and L-Tyrosine were obtained from Sigma-Aldrich, Inc. (St. Louis, Mo.). The enzyme activity was measured in buffer containing 100 mM phosphate buffer pH 6.8, 5% absolute ethanol, 2 micrograms / milliliter mushroom tyrosinase, and 0.2 mg / ml L-Tyrosine. The reaction (conversion of L-Tyrosine to DOPAchrome) was conducted in triplicates at 25° C. for 30 min, and absorbance was then measured at 492 nm. Kojic Acid was used as a positive control inhibitor in these assays. Percent change in tyrosinase activity relative to vehicle control was calculated. Table 1 shows the effect of treatment with each substance on tyrosinase synthesis in the mushroom tyrosinase assay.

TABLE 1PERCENT CHANGE IN TYROSINASE ACTIVITY COMPARED TO DMSO VEHICLE CONTROLMUSHROOM TYROSINASE ASSAYTyrosinaseTest CompoundConcentrationInhibitionAV69890.001%−36%AV6989 0.01%−75%

example 2

Inhibition of Melanin Production

[0108]The effects of various test compounds on melanin levels were determined by performing assays using B16 melanoma cells. These cells are known to constitutively produce melanin and are a commonly utilized and accepted model system for monitoring the inhibition of melanin synthesis. The B16 mouse melanoma cells were seeded (ATCC, cat. #: CRL-6475) into 96-well tissue culture-treated plates (BD Falcon) and treated with test actives or controls in phenol red free DMEM (Mediatech; cat. #: 17-205-CV) with 2 nanogram / ml of alpha MSH (Fluka; cat #:63605). The cells were examined for their ability to modulate pigment formation. Cells were exposed to diluted test actives or control, where test active had a final concentration of 0.001% or 0.0001%. Tests were performed in 6 replicates each. Following the treatment period (4 days), the level of pigment produced or melanin synthesized was quantified by reading the absorbance at 540 nm using a standard micropl...

example 3

Inhibition of Melanin Production in Human Primary Melanocyte

[0111]The effects of various test compounds on melanin productions were determined by performing assays using Human Epidermal Melanocytes, neonatal, darkly pigmented donor (HEMn-DP). The HEMn-DP cells were seeded (Invitrogen; cat. #: C-202-5C) into 6-well tissue culture-treated plates (BD Falcon) and treated with test actives or controls in Medium 254 (Invitrogen; cat. #: M-254-500) supplemented with 1% HMSG (Invitrogen; cat. #: S-002-5) and 1% P / S. The cells were examined for their ability to modulate pigment formation. Cells were exposed to diluted test actives or control, where test active had a final concentration of 0.001% or 0.0001%. Tests were performed in triplicates each. Following the treatment period (5 days), supernatants were aspirated. The melanin was extracted with 0.5 ml of 2N NaOH for 30 minutes at 80° C. The level of melanin synthesized within the cells was quantified by reading the absorbance at 405 nm us...

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Abstract

The compositions and methods of described herein comprise novel ingredients effective to reduce unwanted pigmentation, such as skin discoloration, freckles, age spots, liver spots, sun damage, tans, pigmented acne marks, scars, pigmented birthmarks, hyperpigmentation, post-inflammatory hyperpigmentation, post-injury hyperpigmentation, melasma, cholasma, after-burn scar, nail stain, yellowing of skin, dark circles under eyes, and the like. The composition may include additional ingredients accordingly for a colored cosmetic, moisturizer, cleanser, toner, and the like.

Description

CROSS-REFERENCE TO RELATED APPLICATION[0001]This patent application is a U.S. National Phase application of International Application No. PCT / US2014 / 021187, filed Mar. 6, 2014, which claims priority to U.S. Patent Application Ser. No. 61 / 779,263, filed on Mar. 13, 2013. The entirety of each application is incorporated herein in their entirety by reference. The International Application was published in English on Oct. 9, 2014 as Publication No. WO / 2014 / 164200.FIELD OF INVENTION[0002]The present invention relates generally to novel compounds, cosmetic formulations, and methods of improving the aesthetic appearance and health of human skin. In particular, the invention relates to substances that reduce unwanted pigmentation in human skin.BACKGROUND[0003]Several skin conditions are associated with the overproduction or unwanted production of melanin the skin, including age spots, freckles, and liver spots. The synthesis of melanin occurs in melanocyte cells in the skin and is a complex...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K8/49A61Q19/02A61Q19/00
CPCA61K8/4973A61K8/49A61K2800/10A61Q19/02A61Q19/00A61Q19/08A61K31/175A61K2800/40A61Q19/007
Inventor HU, HONGYIM, SUNGHANSANTHANAM, UMALYGA, JOHN W.
Owner AVON PROD INC
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