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A nonapeptide-1 derivative and its synthesis method and application

A synthesis method and derivative technology, applied in the field of cosmetic peptides, can solve the problem of nonapeptide-1 derivatives, etc., and achieve the effects of inhibiting tyrosinase activity, scavenging DPPH free radicals, and preventing skin aging.

Active Publication Date: 2022-03-29
浙江湃肽生物股份有限公司深圳分公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although nonapeptide-1 exhibits various effects and applications as described above, there are few studies on nonapeptide-1 derivatives at present.

Method used

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  • A nonapeptide-1 derivative and its synthesis method and application
  • A nonapeptide-1 derivative and its synthesis method and application
  • A nonapeptide-1 derivative and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] The synthetic method of nonapeptide-1-Aa derivative

[0049] Adding nonapeptide-1, asiatic acid, HOBt and DCC to CH 2 Cl 2 , stirred at room temperature for 24 h, after the reaction, the solvent was distilled off under reduced pressure, distilled water and ethyl acetate were added for extraction, the organic layer was washed with distilled water, hydrochloric acid solution, saturated sodium bicarbonate solution and saturated sodium chloride solution successively, and finally Dry over anhydrous sodium sulfate, concentrate under reduced pressure, and finally recrystallize from chloroform-methanol to obtain nonapeptide-1-Aa derivatives with a yield of 81.15%.

[0050] Wherein, the molar ratio of nonapeptide-1 and asiatic acid is 1:3.0, the molar ratio of asiatic acid, HOBt and DCC is 1:1.05:1.05, nonapeptide-1 and CH 2 Cl 2 The dosage ratio of nonapeptide-1 and ethyl acetate is 1 g: 6 mL; during the extraction process, the volume ratio of distilled water and ethyl aceta...

Embodiment 2

[0052] The synthetic method of nonapeptide-1-Aa derivative

[0053] The raw materials used in this example and the synthesis method are basically the same as those in Example 1, except that the used condensing agent HOBt / DCC is replaced by DMAP / DCC, and the molar ratio of Asiatic acid, DMAP and DCC is 1:0.2:1.05. The yield of nonapeptide-1-Aa derivative was 83.42%.

Embodiment 3

[0055] The synthetic method of nonapeptide-1-Ma derivative

[0056] The raw materials used in this example and the synthesis method are basically the same as those in Example 1, the difference being that the asiatic acid used is replaced by madecassic acid. The yield of nonapeptide-1-Ma derivative was 80.02%.

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Abstract

The invention discloses a nonapeptide-1 derivative and its synthesis method and application, belonging to the technical field of cosmetic peptides, using nonapeptide-1, asiatic acid or hydroxyasiatic acid as raw materials, nonapeptide-1 and asiatic acid The molar ratio of nonapeptide-1 and madecassic acid is 1: 2.0-4.0, or the molar ratio of nonapeptide-1 and madecassic acid is 1: 2.0-4.0, with HOBt / DCC or DMAP / DCC as condensing agent, carry out condensation reaction, obtain nine Peptide-1 derivatives. The nonapeptide-1 derivative of the present invention has inhibitory tyrosinase activity, antioxidant activity, anti-photoaging activity, anti-sensitivity activity, and good transdermal permeability, and can be used to prepare skin depigmentation agents, whitening agents, and light spots Agents, anti-aging agents, anti-sensitivity agents.

Description

technical field [0001] The invention belongs to the technical field of cosmetic peptides, and in particular relates to a nonapeptide-1 derivative and its synthesis method and application. Background technique [0002] Nonapeptide-1, also known as Meritide, is a whitening nonapeptide containing nine amino acids, mainly used for whitening and brightening skin and removing freckles. The first step in the formation of melanin is the combination of melanocyte-stimulating hormone and the MC1 receptor on melanocytes, and then activates tyrosinase to further form melanin. Nonapeptide-1 is a biomimetic peptide, which has a very good match with the MC1 receptor on melanocytes, so it can be used as an antagonist of melanocyte-stimulating hormone, competitively binding to MC1 receptors, and preventing tyrosine The enzyme is further activated to produce melanin. Nonapeptide-1 competitively blocks the entrance of receptors and various factor signals on melanoblasts, weakens the activity...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K7/06C07K1/107A61K8/64A61Q19/02A61Q19/08A61Q19/00
CPCC07K7/06A61K8/64A61Q19/02A61Q19/08A61Q19/005A61K2800/782A61K2800/522
Inventor 陈超傅小明钱令页黄毅
Owner 浙江湃肽生物股份有限公司深圳分公司
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