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Trolox-peptide conjugate and use thereof

A technology of conjugates and cosmetic compositions, applied in the field of Trolox-peptide conjugates, can solve the problems of hair growth, high price, and difficulty in large-scale production that have not been shown to treat hair loss, so as to control or prevent hair loss and promote hair loss. Growth, inhibitory activity effects

Pending Publication Date: 2022-02-01
CAREGEN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Finasteride is easy to take and very effective, but the reagents used to make finasteride are expensive or toxic and can be a burden on production costs
In particular, incidental products are not easily removed, and the purity of the final product may deteriorate
In addition, there are problems in that reagents or active derivatives whose activity is easily inhibited by moisture are used, and it is difficult to produce on a large scale
However, conventional hair restorers do not have the function of preventing hair loss and promoting hair growth at the same time, and substantially do not show significant effects of treating hair loss and promoting hair growth

Method used

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  • Trolox-peptide conjugate and use thereof
  • Trolox-peptide conjugate and use thereof
  • Trolox-peptide conjugate and use thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0073] peptide synthesis

[0074] [1-1] Include SEQ ID Synthesis of Peptides with Amino Acid Sequence NO:2

[0075]700 mg of chlorotrityl chloride resin (CTL resin, Nova biochem Class No. 01-64-0021) was placed in the reaction vessel, and 10 ml of dichloromethane was added to the reaction vessel, followed by stirring for 3 minutes. Then, the solvent was removed and 10 ml of dimethylformamide was added to the reaction vessel. After stirring for an additional 3 minutes, the solvent was removed. 10 ml of dichloromethane was added to the reaction vessel, and after adding 200 mmol of Fmoc-Cys(trt)-OH (Bachem, Switzerland) and 400 mmol of diisopropylethylamine, stirring was performed for 1 hour to initiate a reaction. After washing the reaction product, methanol and diisopropylethylamine mixed at a ratio of 2:1 were added, and a reaction was performed for 10 minutes. Then, excess dichloromethane and dimethylformamide mixed in a ratio of 1:1 were added and washed again. The...

preparation example 2

[0083] [Preparation Example 2] Preparation of Trolox-peptide conjugates

[0084] 1 mol of peptidyl resin and 10 mL of 1-methyl-2-pyrrolidone (NMP) were placed in a peptide reactor, and 270 mg (2.0 equivalents) of 1-hydroxybenzotriazole (1-HOBt) were added to the reactor ) and 759 mg (2.0 equivalents) of N,N,N',N'-tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (HBTU), followed by reaction for 30 minutes . Then, 388 mg (3.0 equivalents) of N,N'-diisopropylethylamine (DIEA) and 500 mg (2.0 equivalents) of Trolox were added to the reaction product, reacted at room temperature for 72 hours, and were filtered. Then, the filtrate and the cleavage solution were reacted at room temperature for 2 hours to remove the resin and the protecting group. Finally, 10 mL of diethyl ether was added for crystallization, and a Trolox-peptide conjugate (ie, a conjugate of the peptide of SEQ ID NO: 1, SEQ ID NO: 2 or SEQ ID NO: 3 and Trolox) was prepared. The reaction used to pr...

Embodiment 1

[0088] Confirmation of proliferation promoting effect

[0089] Human hair follicle dermal papilla cells (HFDPC) and human keratinocytes HaCaT were mixed at 2×10 3 Aliquot into each well of a 96-well plate and incubate overnight. The medium in which the cells were cultured was replaced with serum-free medium, treated with 0.5 μM, 5 μM or 50 μM of Trolox-peptide conjugate, and cultured for an additional 3 days. Then, in order to confirm cell proliferation, 4 mg / ml of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) was placed in 100 μl of each well well, and reacted for 4 hours. The formazan thus prepared was treated and dissolved with DMSO, and the absorbance at 560 nm was measured using a microplate reader. In this case, as a positive control, 1 μM of IGF-1 or EGF (IGF-1 or EGF is known to be a growth factor promoting the proliferation of HFDPC and HaCaT cells) was used, and as a comparison group, a single Trolox compound and a compound with A compound ...

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Abstract

The present invention relates to a Trolox-peptide conjugate having a structure in which Trolox and a peptide are chemically bonded. The Trolox-peptide conjugate not only very effectively inhibits the activity of 5 alpha-reductase, but also inhibits the death of papilla cells and keratinocytes, promotes the growth thereof, and has antioxidative effects, and thus can remarkably promote hair formation while avoiding or preventing hair loss.

Description

technical field [0001] The present invention relates to a Trolox-peptide conjugate and its application. The Trolox-peptide conjugate has a structure in which Trolox and peptide are chemically combined. Background technique [0002] The hair follicle is a unique organ in mammalian skin and is an organ that grows from the lower part of the original epidermis and extends into deeper skin layers. At the base of the hair follicle is a plug of cells called the balloon or dermal papilla cells, and the dermal papilla cells are essential for the normal circulation of the follicle and the growth of the hair shaft. The hair shaft has a filamentous structure formed by epithelial cells, which are the stems that emerge from the scalp and are composed of keratin filaments and filament-aggregating proteins tightly attached to them . [0003] Human hair repeats cyclically: the anagen phase when the hair grows, the catagen phase when it stops growing and shrinks the hair bulb, the telogen p...

Claims

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Application Information

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IPC IPC(8): A61K8/64A61K8/49A61K31/352A61K38/08A61K38/10A61K38/16A61K47/55A61K47/64A61P17/14A61Q7/00A61Q19/08A61Q5/02A61Q5/12
CPCA61K8/64A61K8/498A61Q7/00A61Q19/08A61Q5/02A61Q5/12A61K31/352A61K38/08A61K38/10A61K38/16A61K47/55A61K47/64A61P17/14A61K2800/522A61K2800/782C07K7/06C07K7/08A61K2800/57A61K31/353C07K19/00
Inventor 郑镕池金银美李应智金敏雄
Owner CAREGEN
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