WO2023143184A1 - Compositions et procédés de prévention ou d'amélioration du vieillissement prématuré de la peau - Google Patents

Compositions et procédés de prévention ou d'amélioration du vieillissement prématuré de la peau Download PDF

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Publication number
WO2023143184A1
WO2023143184A1 PCT/CN2023/072356 CN2023072356W WO2023143184A1 WO 2023143184 A1 WO2023143184 A1 WO 2023143184A1 CN 2023072356 W CN2023072356 W CN 2023072356W WO 2023143184 A1 WO2023143184 A1 WO 2023143184A1
Authority
WO
WIPO (PCT)
Prior art keywords
skin
composition
ergothioneine
improving
photoaging
Prior art date
Application number
PCT/CN2023/072356
Other languages
English (en)
Inventor
Rui SHU
Mingru WANG
Shawn Wells
Kylin LIAO
Original Assignee
Nanjing Nutrabuilding Bio-Tech Co., Ltd.
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 Nanjing Nutrabuilding Bio-Tech Co., Ltd. filed Critical Nanjing Nutrabuilding Bio-Tech Co., Ltd.
Priority to CN202380007853.5A priority Critical patent/CN116390722A/zh
Publication of WO2023143184A1 publication Critical patent/WO2023143184A1/fr

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Classifications

    • 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
    • A61P17/18—Antioxidants, e.g. antiradicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4172—Imidazole-alkanecarboxylic acids, e.g. histidine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles

Definitions

  • One aspect of the invention relates to a topical composition, comprising at least one ergothioneine, an analog or derivative thereof, or a dermatologically acceptable salt thereof, for preventing or treating skin aging, particularly, premature aging.
  • Another aspect of the invention relates to a method for treating skin aging, comprising topical application of the composition of the invention. This topical composition has been reported to rarely produce skin irritation.
  • Skin is the main barrier that segregate our body from the outer environment and protects us against environmental stressors. However, like other human organs, skin is also subject to the aging process. Skin aging is a complex biological phenomenon, influenced by both intrinsic factors (e.g., genetics, cellular metabolism, hormone environment) and extrinsic factors (e.g., chemicals, toxins, pollutants, ultraviolet (UV) , and ionizing radiation) , and affecting different constituents of the skin.
  • intrinsic factors e.g., genetics, cellular metabolism, hormone environment
  • extrinsic factors e.g., chemicals, toxins, pollutants, ultraviolet (UV) , and ionizing radiation
  • Intrinsic aging is an inevitable, genetically determined process that affects unexposed and exposed skin and is characterized by dryness, laxity, fine wrinkles, and skin atrophy, while extrinsic aging is engendered by external environment factors such as air pollution, smoking, poor nutrition, and sun exposure, resulting in coarse wrinkles, loss of elasticity, laxity, and rough ⁇ textured appearance (Cell Transplant. 2018 May; 27 (5) : 729–738) . While many external factors could contribute to skin aging, ultraviolet (UV) radiation from sunlight is the primary factor of extrinsic skin aging, also referred to as premature skin aging or photoaging. UV irradiation can induce non ⁇ genomic signal transduction.
  • UV ultraviolet
  • ROS reactive oxygen species
  • Photoaging can be controlled to an extent as it is a result of external factors. Photoaging affects the sun ⁇ exposed areas and is characterized clinically by fine and coarse wrinkling, roughness, dryness, laxity, and pigmentary changes. There is also an increase in development of benign and malignant neoplasms on photoaged skin (Journal of the American Academy of Dermatology, Volume 49, Issue 4, October 2003, Pages 690 ⁇ 697) . The anti ⁇ aging strategies to combat skin aging signs and dysfunction have been developed over the last decades. As people’s cosmetic requirements increase, more research efforts are conducted to help relieving skin aging or preventing of extrinsic aging from occurring.
  • Ergothioneine is a naturally occurring, sulfur ⁇ containing amino acid, and is presumed to function as a natural antioxidant. It is mainly found in mushrooms, but also in king crab, and animals that have grazed on grasses containing ergothioneine. Since humans or other vertebrates are unable to synthesize ergothioneine, it can only be acquired by diet. Studies in animals and humans have found no toxicity or adverse effects to be associated with ergothioneine administration, even at high doses. Recently, ergothioneine (Tetrahedron, Paris, France) has attained European Food Safety Authority approval as a Novel Food in the European Union and is generally recognized as a safe supplement and food ingredient by the Food and Drug Administration in the US (GRAS notice No. 734) (FEBS Letters 592 (2016) 3357–3366) .
  • Applicants of the present invention have investigated the safety and efficacy of a composition comprising ergothioneine on alleviating skin aging, and provided a topical composition comprising at least one ergothioneine, an analog or derivative thereof, or a dermatologically acceptable salt thereof, which can counteract or delay skin aging signs in a safe and effective way.
  • This topical composition has been reported to rarely produce skin irritation.
  • This invention generally relates to compositions for preventing or improving skin aging, containing at least an active compound which is ergothioneine, an analog, derivative, or dermatologically acceptable salt thereof. Additionally, this invention also relates to a topical application of the composition of the invention to an area of the skin for preventing or treating of damages to skin, particularly, skin damages resulting from premature aging (also known as photoaging) .
  • compositions for preventing or treating skin aging comprising at least one compound selected from the group consisting of ergothioneine, an analog or derivative thereof, or a dermatologically acceptable salt thereof.
  • ergothioneine, an analog or derivative thereof, or a dermatologically acceptable salt thereof is present in an amount ranging from 0.01 to 20 %by weight (w/w) , 0.01 to 15 %by weight (w/w) , or 0.01 to 12 %by weight (w/w) .
  • ergothioneine, an analog or derivative thereof, or a dermatologically acceptable salt thereof is present in an amount of 10%by weight (w/w) . In some other embodiments, ergothioneine, an analog or derivative thereof, or a dermatologically acceptable salt thereof, is present in an amount of 0.5 %by weight (w/w) .
  • the analog or derivative of ergothioneine is selected from the group consisting of S ⁇ Methyl ⁇ L ⁇ Ergothioneine, N ⁇ Desmethyl L ⁇ Ergothioneine Methyl Ester, N(Im) ⁇ Ethoxycarbonyl ⁇ S ⁇ ethoxycarbonyl L ⁇ Ergothioneine Methyl Ester Iodide, N ⁇ Desmethyl L ⁇ Ergothioneine ⁇ D6 Methyl Ester, L ⁇ (+) ⁇ Ergothioneine ⁇ D3, ergothioneine sulfonate, and L ⁇ Ergothioneine Hydrochloride.
  • ergothioneine is L ⁇ ergothioneine.
  • the composition further comprises at least one additional agent.
  • additional agent include, but not limited to, growth factor, Hyaluronic Acid, Retinol/Retinoic acid, Hydrolyzed Collagen/Collagen Peptides, Vitamin C, Vitamin E, Cannabidiol, EGCG/Green tea, Polyhydroxy Acids , Glycolic Acid , Aloe vera , Niacinamide , Resveratrol , Superoxide dismutase , Tea tree oil , Bakuchiol , Grapeseed oil , Petroleum jelly , and squalene.
  • growth factors are, but not limited to, EGF, FGF, NGF, PDGF, VEGF, IGF, GMCSF, GCSF, TGF, Erythropieitn, TPO, BMP, HGF, GDF, Neurotrophins, MSF, SGF, GDF.
  • the skin aging comprises photoaging.
  • Example of photoaging includes, but not limited to, wrinkling, scar tissue deposition, altered skin elasticity, altered skin color, altered skin texture, altered skin thickness, angioma, telangiectasia, sunburn, dryness, itchiness, neoplasia and precancerous growth.
  • the preventing or improving treating skin aging comprises one or more of the following effects: alleviating skin photoaging, diminishing skin wrinkles, improving skin elasticity, improving skin firmness, or improving skin’s radiance, luminosity, or texture.
  • the composition improves skin’s radiance, luminosity, or texture, and rarely produces skin irritation.
  • the composition is prepared in any one formulation selected from the group consisting of a skin lotion, a skin softener, a skin toner, a skin cream, a sunscreen, an essence, a mask pack, a mask sheet, a soap, a shampoo, a cleaning foam, a cleaning lotion, a cleaning cream, an ointment, a gel and a massage cream.
  • Another aspect of the invention relates to a method for preventing or improving skin aging in a subject, comprising topically applying the composition, comprising at least one compound selected from the group consisting of ergothioneine, an analog or derivative thereof, or a dermatologically acceptable salt thereof, to an area of the skin.
  • ergothioneine an analog or derivative thereof, or a dermatologically acceptable salt thereof, is present in an amount ranging from 0.01 to 20 %by weight (w/w) , 0.01 to 15 %by weight (w/w) , or 0.01 to 12%by weight (w/w) .
  • the subject is human.
  • ergothioneine is L ⁇ ergothioneine.
  • the skin aging comprises photoaging.
  • the preventing or improving treating skin aging comprises one or more of the following effects: alleviating skin photoaging, diminishing skin wrinkles, improving skin elasticity, improving skin firmness, or improving skin’s radiance, luminosity, or texture. In some particular embodiments, the preventing or improving treating skin aging comprises one or more of the following effects: improving skin’s radiance, luminosity, or texture, and rarely produces skin irritation.
  • a further aspect of the invention relates to use of ergothioneine in manufacturing a composition capable of treating skin photoaging.
  • Figure 1 depicts the change of Methylobacterium ⁇ Methylorubrum after 12 ⁇ week's treatment of Ergothioneine.
  • compositions comprising at least one compound selected from the group consisting of ergothioneine, an analog or derivative thereof, or a dermatologically acceptable salt thereof; as well as methods for preventing or treating skin aging, comprising topical application of the composition of the invention to an area of skin.
  • the composition can be prepared in a variety of forms, such as a skin lotion, a skin softener, a skin toner, a skin cream, a sunscreen, an essence, a mask pack, a mask sheet, a soap, a shampoo, a cleaning foam, a cleaning lotion, a cleaning cream, an ointment, a gel, and a massage cream.
  • the term “or” is meant to include both “and” and “or” . In other words, the term “or” may also be replaced with “and/or. ”
  • the term “at least” followed by a number is used to denote the start of a range beginning with that number.
  • the term “comprise” or “include” and their conjugations refer to a situation where said terms are used in their non-limiting sense to mean that items following the word are included, but items not specifically mentioned are not excluded. It also encompasses the more limiting verb ‘to consist essentially of’a nd ‘to consist of’ .
  • the term “subject” or “patient” is used interchangeably and as used herein mean any mammal including but not limited to human beings including a human patient or subject to which the compositions of the invention can be administered.
  • the term “mammals” include human patients and non ⁇ human primates, as well as experimental animals such as rabbits, rats, and mice, and other animals.
  • the term “treat” , “treating” or “treatment” and the like as used herein, refers to any indicia of success in the prevention or amelioration of an injury, pathology or condition, including any objective or subjective parameter such as abatement; remission; diminishing of symptoms or making the injury, pathology, or condition more tolerable to the patient; slowing in the rate of degeneration or decline; making the final point of degeneration less debilitating; or improving a subject's physical or mental well ⁇ being.
  • the treatment or amelioration of symptoms can be based on objective or subjective parameters; including the results of a physical examination, neurological examination, and/or psychiatric evaluations. Accordingly, the term “treating” or “treatment” includes the administration of L ⁇ Ergothioneine which may be in combination with other compounds or agents.
  • the terms “improving” and the like are used generally to mean improving or alleviating it or its symptoms partially in the subject, such as alleviating skin photoaging, diminishing skin wrinkles, improving skin elasticity, improving skin firmness, or improving skin’s radiance, luminosity, or texture.
  • preventing, ” “prevention, ” and the like are used generally to mean preventing or inhibiting deterioration or further deterioration of the visual system of an aging subject, as compared with a comparable visual system not receiving the synthetic retinal derivative.
  • the term “effective amount” refers to an amount that is required to improve at least one symptom of a medical condition in an individual.
  • a "cosmetic" can be contacted with the skin, such as by being rubbed, poured, sprinkled, or sprayed on the skin or otherwise introduced into or onto the skin, and is intended to improve the aesthetic appearance of the skin, such as by cleaning, beautifying, promoting attractiveness, or altering, e.g., improving, the aesthetic appearance of the contacted skin.
  • a cosmetic benefit is typically visual or aesthetic, and can be evaluated using subjective or objective assays.
  • topical application means directly laying on or spreading on the skin, hair, or nail, e.g., by use of the hands or an applicator such as a wipe.
  • the term "dermatologically acceptable” is used to refer to compounds and compositions that retain biological effectiveness and which are suitable for use in contact with the skin or hair of humans and lower animals without undue toxicity, incompatibility, instability, irritation, allergic response, and the like.
  • subjects will be randomly assigned to use 0.01 ⁇ 12%ergothioneine moisturizer of the invention to the right or left face and the bland moisturizer to the opposite face. Neither the subjects nor the investigator will know the identity of the creams. The study coordinator will develop and maintain the study blind. Subjects will be dispensed a diary to record daily use of the moisturizers, provided a return schedule, and asked to return to the research center at week 4, 8 and 12. On each return (check point) , the enrolled subjects will complete baseline efficacy and tolerability assessments separately for each side of the face. The skin elasticity and corneometry measurements will be made and recorded from both sides of the face. Additionally, at week 8 and 12, ten randomly selected subjects will participate in the photography substudy.
  • VISIA ⁇ CR images will be taken of the front, right, and left face with standard lighting 1 at baseline and week 12 in both jpeg and CR2 raw files for image analysis at a later date. Furthermore, at week 12 (the study endpoint) , both sides of the face are swabbed for microbiome analysis. Subject diaries will be checked for compliance and collected.
  • Noninvasive assessments skin elasticity and corneometery hydration measurements will be made and recorded from both the right and left cheek at baseline, week 4, week 8, and week 12 (Data will be recorded in the Table below) .
  • Microbiome swabbing Both sides of the face will be swabbed for microbiome analysis at baseline and week 12. Two swabs will be generated per visit for a total of 4 swabs per subject. Swabs will be stored in the –80°C freezer until the end of the study for shipping (on dry ice) to a commercial laboratory in Vancouver, Canada for microbiome quantitative profiling . 120 swabs will be shipped at the end of study for analysis.
  • ⁇ STEP 1 Dip a fresh swab in molecular grade DNA free water. With one hand, stretch the skin site taut. With the other hand, hold the swab so the shaft is parallel to the skin surface. Apply firm pressure and rub the swab back and forth rigorously 50 times (for 30 seconds) rotating the swab slowly while swabbing.
  • ⁇ STEP 2 Carefully return the swab to the tube, ensuring that neither the swab, the swab stick nor the vessel touch any surface.
  • ⁇ STEP 3 Place the tube into a biospecimen bag and freeze at ⁇ 80°C until ready to ship.
  • the intensity or severity of an AE is characterized as:
  • Moderate AE sufficiently discomforting to interfere with daily activity.
  • AE occurs following the application of the study product and it cannot be reasonably explained by any other known characteristics of the subject’s clinical state, environmental or toxic factors, or other modes of therapy administered to the subject. It disappears or decreases upon discontinuation of the study product and reappears on a re ⁇ challenge of the study product. This is necessary to evaluate allergic or irritant contact dermatitis.
  • a Wilcoxon signed rank test is used for analysis of all ordinal nonparametric data as compared to baseline.
  • a Student’s T ⁇ test is used to analyze all parametric numerical elasticity and corneometry data.
  • An outside lab will analyze the data from the facial swabs. Statistical significance is defined as p value less than or equal to 0.05.
  • a topical composition comprising ergothioneine was prepared.
  • the amounts of each component of the compositions are given as percentages of each component’s weight relative to the total weight of the composition.
  • the formulation comprises 0.01 to 12 % (w/w) ergothioneine, and one or more additives selected from Hyaluronic Acid (0.1 ⁇ 3%) , Retinol/Retinoic acid (0.1 ⁇ 2%) , Hydrolyzed Collagen/Collagen Peptides (0.1 ⁇ 3%) , Vitamin C (0.1 ⁇ 6%) , Vitamin E (0.1 ⁇ 10%) , Cannabidiol (0.1 ⁇ 5%) , EGCG/Green tea (0.1 ⁇ 10%) , Polyhydroxy Acids (0.1 ⁇ 12%) , Glycolic Acid (0.1 ⁇ 10%) , Aloe vera (0.1 ⁇ 10%) , Niacinamide (0.1 ⁇ 10%) , Resveratrol (0.1 ⁇ 5%) , Superoxide dismutase (0.1 ⁇ 5%) , Tea tree oil (0.1 ⁇ 10%) , Bakuchiol (0.1 ⁇ 5%) , Grapeseed oil (0.1 ⁇ 10%) , Petroleum jelly (0.1 ⁇ 5%) , or squalene (0.1 ⁇ 10%) (w/w)
  • the primary efficacy endpoint was met at week 4 for luminosity and radiance and week 8 for radiance, luminosity, and texture.
  • the safety endpoint was the absence of significant adverse reactions. The safety endpoint was met.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Birds (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne, entre autres, une composition topique destinée à prévenir ou traiter le vieillissement cutané, comprenant au moins un composé choisi dans le groupe constitué par l'ergothionéine, un analogue ou un dérivé de celle-ci, ou un sel de qualité dermatologique de celle-ci. Cette composition topique améliore l'éclat, la luminosité ou la texture de la peau, et ne provoque que rarement des irritations cutanées. Selon un autre aspect, la présente invention concerne un procédé de prévention ou de traitement du photovieillissement chez un sujet, comprenant l'application topique de la composition de l'invention.
PCT/CN2023/072356 2022-01-28 2023-01-16 Compositions et procédés de prévention ou d'amélioration du vieillissement prématuré de la peau WO2023143184A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202380007853.5A CN116390722A (zh) 2022-01-28 2023-01-16 预防或改善皮肤老化的方法和组合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN2022074500 2022-01-28
CNPCT/CN2022/074500 2022-01-28

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WO2023143184A1 true WO2023143184A1 (fr) 2023-08-03

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2281799A1 (fr) * 1997-02-20 1998-08-27 Oxis International, Inc. Procedes et compositions servant a proteger les mitochondries
CN105982890A (zh) * 2014-09-05 2016-10-05 中国医药大学 麦角硫因应用于活化细胞的Nrf2信号通路的用途
CN110917061A (zh) * 2019-12-26 2020-03-27 华熙生物科技股份有限公司 一种含麦角硫因提取液、糙米发酵滤液和乙酰壳糖胺的组合物及其应用
CN113648236A (zh) * 2021-08-26 2021-11-16 上海拜思丽实业有限公司 一种抗氧化组合物、抗氧化化妆品组合物及其制备方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2281799A1 (fr) * 1997-02-20 1998-08-27 Oxis International, Inc. Procedes et compositions servant a proteger les mitochondries
CN105982890A (zh) * 2014-09-05 2016-10-05 中国医药大学 麦角硫因应用于活化细胞的Nrf2信号通路的用途
CN110917061A (zh) * 2019-12-26 2020-03-27 华熙生物科技股份有限公司 一种含麦角硫因提取液、糙米发酵滤液和乙酰壳糖胺的组合物及其应用
CN113648236A (zh) * 2021-08-26 2021-11-16 上海拜思丽实业有限公司 一种抗氧化组合物、抗氧化化妆品组合物及其制备方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
LI, YI QUN; ZHOU, NIAN-BO: "Ergothioneine biological function and major applications", FOOD ENGINEERING, CN, no. 3, 30 September 2010 (2010-09-30), CN , pages 26 - 28, XP009547878, ISSN: 1673-6044 *

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