CN106420680A - Benzophenone derivatives serving as tyrosinase activating agents and applications thereof - Google Patents
Benzophenone derivatives serving as tyrosinase activating agents and applications thereof Download PDFInfo
- Publication number
- CN106420680A CN106420680A CN201610877440.4A CN201610877440A CN106420680A CN 106420680 A CN106420680 A CN 106420680A CN 201610877440 A CN201610877440 A CN 201610877440A CN 106420680 A CN106420680 A CN 106420680A
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- China
- Prior art keywords
- dihydroxy benaophenonel
- benzophenone
- tyrosinase
- aminobenzophenone
- cosmetics
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- 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.)
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- 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
- A61K31/12—Ketones
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
-
- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
-
- 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
- A61Q19/04—Preparations for care of the skin for chemically tanning the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
-
- 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
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
Abstract
The invention belongs to the technical field of cosmetics, medicines and food chemistry, and discloses benzophenone derivatives serving as tyrosinase activating agents and applications thereof. The benzophenone derivatives serve as the tyrosinase activating agents and are one or more than one of 2-hydroxybenzophenone, 3-hydroxybenzophenone, 4-hydroxybenzophenone, 4-methoxybenzophenone, 4-aminobenzophenone, 3-aminobenzophenone, 4, 4'-dihydroxy benaophenonel, 2, 4, 4'-trihydroxybenzophenone or 3-methoxyl-4, 4'-dihydroxy benaophenonel. The compounds disclosed by the invention have intense tyrosinase activation activity and obvious application prospect in medicines (such as treatment of leucoderma) and cosmetics (such as hair-blacking liquid shampoo).
Description
Technical field
The present invention relates to cosmetics, medicine and food chemistry field are and in particular to a kind of benzophenone derivates are used as junket
Propylhomoserin zymoexciter and its application in cosmetics and medicine.
Background technology
Tyrosinase is a multi-functional, enzyme containing two copper atoms, is widely present in microorganism, animals and plants and its people
In body.It is diphenol (monophenolase activity) that this enzyme utilizes the single phenol of molecular oxygen catalysis oxidation, and catalysis oxidation diphenol is corresponding afterwards
Quinone.Quinone, through a series of enzymatic or no enzymatic process, obtains mixing melanin.
Tyrosinase is relevant with a lot of bioprocess, such as closely related with the pigmentation disease of the aging of people, human body.
Recent research indicate that the activity reduction of tyrosinase can make one to suffer from some hypopigmentation diseases, for example：Young person with greying hair, leucoderma
Deng.
Research currently, with respect to tyrosinase inhibitor is more, and the research with regard to tyrosinase activator is less, most
Obtained by random screening.Domestic mainly its activation to tyrosinase is studied by Chinese traditional medicine's extractant, such as Psoralen
The Chinese medical extracts such as fat, the root of kudzu vine, the red sage root, the fleece-flower root, Eclipta prostrata, Radix Angelicae Sinensis all show has different degrees of activation to make to tyrosinase
With.(referring to document：Wang Xiyuan etc., psoralen compound is to tyrosinase synergistic activation performance study.《Natural products research
With exploitation》.2007,19,77～80.Chen Lianghua etc., the research to Mushroom Tyrosinase activation for the medicinal plant.《Xiamen is big
Learn journal (natural science edition)》, 2008,47 (2), 110～114.Deng Xiangqing etc., the reaction of coffee acid active tyrosinase catalysis
Dynamics research,《Food Science》, 2008,29 (4), 98～101.Yan Guilong etc., kudzu root extract is to tyrosinase activity
Impact,《Research and development of natural products》, 2009,21,96～98.) also rare to the research of tyrosinase activator abroad.
Content of the invention
Present invention aims to above-mentioned the deficiencies in the prior art, a kind of benzophenone derivates are provided to be used as junket ammonia
Sour zymoexciter, this activator has high activity.
It is a further object of the present invention to provide above-mentioned benzophenone derivates have activation tyrosinase activity for preparation
Medicine.Leukodermic medicine preferably treated by described medicine.
It is still another object of the present invention to provide above-mentioned benzophenone derivates have activation tyrosine enzyme activity for preparation
The cosmetics of property.Described cosmetics are preferably U.S. melanism cosmetic and/or black hair cosmetics.
The purpose of the present invention is achieved through the following technical solutions：
Benzophenone derivates be used as tyrosinase activator, described benzophenone derivates be 2- dihydroxy benaophenonel,
3- dihydroxy benaophenonel, 4- dihydroxy benaophenonel, 4- methoxy benzophenone, 4- aminobenzophenone, 3- aminobenzophenone,
In 4,4 '-dihydroxy benaophenonel, 2,4,4 '-trihydroxybenzophenone or 3- methoxyl group -4,4 '-dihydroxy benaophenonel one
More than kind.
I.e. described tyrosinase activator is 2- dihydroxy benaophenonel, 3- dihydroxy benaophenonel, 4- dihydroxy benaophenonel, 4-
Methoxy benzophenone, 4- aminobenzophenone, 3- aminobenzophenone, 4,4 '-dihydroxy benaophenonel, 2,4,4 '-three hydroxyls
One or more of base benzophenone or 3- methoxyl group -4,4 '-dihydroxy benaophenonel.
Described benzophenone derivates are used for the medicine that preparation has activation tyrosinase activity.Described medicine is preferably controlled
Treat leukodermic medicine.Now benzophenone derivates are 2- dihydroxy benaophenonel, 3- dihydroxy benaophenonel, 4- hydroxy benzophenone
Ketone, 4- methoxy benzophenone, 4- aminobenzophenone, 3- aminobenzophenone, 4,4 '-dihydroxy benaophenonel, 2,4,4 '-
One or more of trihydroxybenzophenone or 3- methoxyl group -4,4 '-dihydroxy benaophenonel.
Described state benzophenone derivates for preparation have activate tyrosinase activity cosmetics.Described cosmetics are excellent
Elect U.S. melanism cosmetic and/or black hair cosmetics as.Now benzophenone derivates are 2- dihydroxy benaophenonel, 3- hydroxy benzophenone
Ketone, 4- dihydroxy benaophenonel, 4- methoxy benzophenone, 4- aminobenzophenone, 3- aminobenzophenone, 4,4 '-dihydroxy
One or more of benzophenone, 2,4,4 '-trihydroxybenzophenone or 3- methoxyl group -4,4 '-dihydroxy benaophenonel.
With prior art ratio, the invention has the advantages that and beneficial effect：
1：The present invention provides organic compound (benzophenone derivates) as the application of tyrosinase activator, is different from
The natural animal-plant extract applied on the market at present；
2：The benzophenone derivative of the present invention has preferable activity ratio to tyrosinase；Show through in vitro study, this
Bright benzophenone derivates all effectively can activate tyrosinase, thus promoting melanic generation, to improve relevant disease.
Specific embodiment
With reference to embodiment, the present invention is described in further detail, but embodiments of the present invention not limited to this.
Embodiment：Benzophenone derivative is used as the application of tyrosinase activator：
(1) test method：
It is separately added into 890 μ L phosphate buffer solution (pH=6.8) in the centrifuge tube of 1.5mL, and 20 μ of variable concentrations
L compound (benzophenone derivative) solution (DMSO preparation), in final solution, the concentration of DMSO is 2%, is subsequently adding 10 μ L junket
Propylhomoserin enzyme solutions (are prepared with the phosphate buffer solution of pH=6.8,0.5mg/mL), shake up, 25 DEG C of water bath with thermostatic control 30min.Subsequently
Add the L-DOPA solution (1.5mg/mL) of 80 μ L, shake up rapidly, then under 25 DEG C of constant temperatures test solution under 475nm
OD value (OD value) change, testing time 1min, deduction cushioning liquid impact that this is tested.Then increased according to OD value
Straight line obtains its slope, i.e. enzyme activity force value.The test result of the activity ratio to tyrosinase for the benzophenone derivative is as shown in table 1.
Enzyme relative activity is activity ratio.
Enzyme relative activity=(adding enzyme activity force value/not after activator plus the enzyme activity force value of activator) × 100%
The Activation Activity to tyrosinase for the table 1 benzophenone derivates series two
Above-described embodiment is the present invention preferably embodiment, but embodiments of the present invention are not subject to above-described embodiment
Limit, other any Spirit Essences without departing from the present invention and the change made under principle, modification, replacement, combine, simplify,
All should be equivalent substitute mode, be included within protection scope of the present invention.
Claims (5)
1. benzophenone derivates be used as tyrosinase activator it is characterised in that：Described benzophenone derivates are 2- hydroxyl
Benzophenone, 3- dihydroxy benaophenonel, 4- dihydroxy benaophenonel, 4- methoxy benzophenone, 4- aminobenzophenone, 3- amido
Benzophenone, 4,4 '-dihydroxy benaophenonel, 2,4,4 '-trihydroxybenzophenone or 3- methoxyl group -4,4 '-dihydroxy hexichol
One or more of ketone.
2. benzophenone derivates be used for preparation have activation tyrosinase activity medicine it is characterised in that：Described hexichol first
Ketone derivatives are 2- dihydroxy benaophenonel, 3- dihydroxy benaophenonel, 4- dihydroxy benaophenonel, 4- methoxy benzophenone, 4- amine
Base benzophenone, 3- aminobenzophenone, 4,4 '-dihydroxy benaophenonel, 2,4,4 '-trihydroxybenzophenone or 3- methoxy
One or more of base -4,4 '-dihydroxy benaophenonel.
3. benzophenone derivates are used for the medicine that preparation has activation tyrosinase activity according to claim 2, and it is special
Levy and be：Described medicine is to treat leukodermic medicine.
4. benzophenone derivates be used for preparation have activation tyrosinase activity cosmetics it is characterised in that：Described hexichol
Ketone derivatives are 2- dihydroxy benaophenonel, 3- dihydroxy benaophenonel, 4- dihydroxy benaophenonel, 4- methoxy benzophenone, 4-
Aminobenzophenone, 3- aminobenzophenone, 4,4 '-dihydroxy benaophenonel, 2,4,4 '-trihydroxybenzophenone or 3- methoxy
One or more of base -4,4 '-dihydroxy benaophenonel.
5. benzophenone derivates are used for the cosmetics that preparation has activation tyrosinase activity according to claim 4, its
It is characterised by：Described cosmetics are U.S. melanism cosmetic and/or black hair cosmetics.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610877440.4A CN106420680B (en) | 2016-09-30 | 2016-09-30 | Benzophenone derivates are used as tyrosinase activator and its application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610877440.4A CN106420680B (en) | 2016-09-30 | 2016-09-30 | Benzophenone derivates are used as tyrosinase activator and its application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106420680A true CN106420680A (en) | 2017-02-22 |
| CN106420680B CN106420680B (en) | 2019-04-23 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201610877440.4A Active CN106420680B (en) | 2016-09-30 | 2016-09-30 | Benzophenone derivates are used as tyrosinase activator and its application |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111892486A (en) * | 2019-05-06 | 2020-11-06 | 莆田学院 | Hydroxyl-substituted benzophenone compound and preparation method and application thereof |
| CN113143897A (en) * | 2021-04-20 | 2021-07-23 | 中国科学院武汉病毒研究所 | Application of 4-aminobenzophenone |
| CN115212192A (en) * | 2022-08-15 | 2022-10-21 | 山西医科大学 | Application of benzophenone derivative in preparation of anti-renal fibrosis medicine |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060134031A1 (en) * | 2004-12-22 | 2006-06-22 | Dennis Decola | Phototherapy compositions and methods |
| CN101460060A (en) * | 2006-03-01 | 2009-06-17 | 特莱斯特拉塔公司 | Composition and method for topical treatment of tar-responsive dermatological disorders |
-
2016
- 2016-09-30 CN CN201610877440.4A patent/CN106420680B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060134031A1 (en) * | 2004-12-22 | 2006-06-22 | Dennis Decola | Phototherapy compositions and methods |
| CN101460060A (en) * | 2006-03-01 | 2009-06-17 | 特莱斯特拉塔公司 | Composition and method for topical treatment of tar-responsive dermatological disorders |
Non-Patent Citations (1)
| Title |
|---|
| YASUTAKA KURODA等: "Depigmentation of the skin induced by 4-(4-hydroxyphenyl)-2-butanol is spontaneously re-pigmented in brown and black guinea pigs.", 《THE JOURNAL OF TOXICOLOGICAL SCIENCES》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111892486A (en) * | 2019-05-06 | 2020-11-06 | 莆田学院 | Hydroxyl-substituted benzophenone compound and preparation method and application thereof |
| CN113143897A (en) * | 2021-04-20 | 2021-07-23 | 中国科学院武汉病毒研究所 | Application of 4-aminobenzophenone |
| CN115212192A (en) * | 2022-08-15 | 2022-10-21 | 山西医科大学 | Application of benzophenone derivative in preparation of anti-renal fibrosis medicine |
| CN115212192B (en) * | 2022-08-15 | 2023-09-08 | 山西医科大学 | Application of diphenyl ketone derivative in preparation of kidney fibrosis resisting medicine |
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| Publication number | Publication date |
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| CN106420680B (en) | 2019-04-23 |
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