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CN-122011095-A - Acetyl hexapeptide, preparation method and application thereof

CN122011095ACN 122011095 ACN122011095 ACN 122011095ACN-122011095-A

Abstract

The invention relates to an acetyl hexapeptide, a preparation method and application thereof. The acetyl hexapeptide comprises a hexapeptide of amino acid sequence EMEQRR. The acetyl hexapeptide provided by the invention not only can play an anti-aging effect at a low concentration, but also can show better safety and higher bioavailability.

Inventors

  • JI YIQIONG
  • WANG HONGWEI

Assignees

  • 中科纳瑞(苏州)科技有限公司

Dates

Publication Date
20260512
Application Date
20251231

Claims (10)

  1. 1. An acetyl hexapeptide, wherein the acetyl hexapeptide comprises a hexapeptide having an amino acid sequence EMEQRR.
  2. 2. The acetyl hexapeptide of claim 1, wherein the N-terminus of the acetyl hexapeptide has an acetylation modification.
  3. 3. The acetyl hexapeptide of claim 1, wherein the acetyl hexapeptide has the structure shown below: 。
  4. 4. a process for the preparation of an acetyl hexapeptide according to any one of claims 1 to 3, comprising the condensation of a hexapeptide of amino acid sequence EMEQRR with acetic acid.
  5. 5. The process according to claim 4, wherein the hexapeptide is prepared by solid phase synthesis and/or The molar ratio of the acetic acid to the hexapeptide is 1 (0.5-1.5).
  6. 6. The process according to claim 4, wherein the condensation reaction uses 1-ethyl-3 [ 3-dimethylaminopropyl ] carbodiimide hydrochloride (EDC) and hydroxysuccinimide (NHS) as the condensing reagents, and/or The condensation reaction uses trifluoroacetic acid (TFA), phenylthiofide, ethanedithiol, phenol and water as cleavage reagents, and/or, The condensation reaction takes 0.1 to 24 hours, and/or The temperature of the condensation reaction is 0-80 ℃.
  7. 7. The process according to claim 6, wherein the molar ratio of acetic acid to NHS is 1 (1.0-1.5), and/or The molar ratio of the acetic acid to the EDC being 1 (1.0-1.5), and/or The volume ratio of TFA, phenyl sulfide, ethylene dithiol, phenol, and water is (80:1:1:0.5:0.5) - (90:10:10:8:2).
  8. 8. Use of an acetyl hexapeptide according to any one of claims 1-3 or prepared by the method of preparation according to any one of claims 4-7 in the field of skin care products.
  9. 9. A skin care product comprising an active ingredient and the acetyl hexapeptide of any one of claims 1-3 or the acetyl hexapeptide prepared by the method of any one of claims 4-7.
  10. 10. A skin care product according to claim 9, wherein the content of acetyl hexapeptide in the skin care product is 0.05-1% by mass, and/or The functional components comprise one or more of tranexamic acid, nicotinic acid, nicotinamide or salicylic acid; The skin care product comprises skin care water, milk, cream or facial mask.

Description

Acetyl hexapeptide, preparation method and application thereof Technical Field The invention belongs to the technical field of biological medicines and cosmetics, and particularly relates to an acetyl hexapeptide, a preparation method and application thereof. Background Polypeptide substances are widely used in skin care products as a kind of signal molecules. One class of botulinum toxin polypeptides, such as acetyl hexapeptide-8, has been widely used in anti-aging products as a safe and effective polypeptide. The polypeptide can imitate oligopeptide with 6 amino acids at the N end of SNAP-25 protein, and the acting domain neuromuscular joint affects the formation of a foam-melting complex by participating in competing with SNAP-25 at the site of the foam-melting complex, so that vesicles can not effectively release neurotransmitters, wrinkles caused by facial expression muscle contraction are reduced, and the wrinkle-removing effect on skin wrinkle oil is remarkable. Although the polypeptide has been widely used in skin care products, the effective concentration is still high. Disclosure of Invention Aiming at the defects existing in the prior art, the invention designs and synthesizes the acetyl hexapeptide so as to improve the bioavailability and reduce the effective concentration of the acetyl hexapeptide. According to one aspect of the present invention, there is provided an acetyl hexapeptide comprising a hexapeptide of amino acid sequence EMEQRR, i.e. arginine (Arg) -glutamine (Gln) -glutamic acid (Glu) -methionine (Met) -glutamic acid (Glu). In some embodiments, the hexapeptide has an acetylation modification at the N-terminus. In some embodiments, the acetyl hexapeptide has the structure shown below: 。 According to another aspect of the present invention, there is provided a method for preparing the acetyl hexapeptide of the present invention, which comprises subjecting a hexapeptide having the amino acid sequence EMEQRR to a condensation reaction with acetic acid. In some embodiments, the molar ratio of acetic acid to hexapeptide is 1 (1.0-1.5), e.g., 1:0.5, 1:1, 1:1.1, 1:1.2, 1:1.3, 1:1.4, 1:1.5, or any value therebetween. In some embodiments, the condensation reaction employs 1-ethyl-3 [ 3-dimethylaminopropyl ] carbodiimide hydrochloride (EDC) and hydroxysuccinimide (NHS) as the condensing reagents. In some embodiments, the molar ratio of acetic acid to NHS is 1 (1.0-1.5), e.g., 1:1, 1:1.1, 1:1.2, 1:1.3, 1:1.4, 1:1.5, or any value therebetween. In some embodiments, the molar ratio of acetic acid to EDC is 1 (1.0-1.5), e.g., 1:1, 1:1.1, 1:1.2, 1:1.3, 1:1.4, 1:1.5, or any value therebetween. In some embodiments, the time of the condensation reaction is from 0.1h to 24h, for example, 0.1h, 0.5 h, 1h, 2h, 3h, 4h, 5h, 10h, 15 h, 20 h, 24h, or any value therebetween. In some preferred embodiments, the time of the condensation reaction is from 0.1 to 4 hours. In some embodiments, the temperature of the condensation reaction is 0-80 ℃, e.g., 0 ℃,5 ℃, 10 ℃, 20 ℃, 30 ℃, 40 ℃, 50 ℃, 60 ℃, 70 ℃, 80 ℃, or any value therebetween. In some embodiments, the condensation reaction uses TFA, phenyl sulfide, ethylene dithiol, phenol, and water as cleavage reagents. In some embodiments, the volume ratio of TFA, phenyl sulfide, ethylene dithiol, phenol, and water is (80:1:1:0.5:0.5) - (90:10:10:8:2). In some embodiments, the volume ratio of TFA, phenyl sulfide, ethylene dithiol, phenol, and water is 85:5:5:4:1. In some embodiments, the hexapeptide is prepared using a solid phase synthesis method. In some embodiments, the hexapeptide is prepared by attaching an amino acid to an insoluble resin, then attaching the amino acid via a coupling reaction and a deprotection reaction, and finally cleaving the hexapeptide molecule from the resin. In some embodiments, the insoluble resin is wang resin. In some embodiments, the hexapeptide may be prepared by a biosynthetic method. To this end, the invention also provides a nucleic acid molecule comprising a nucleotide sequence encoding said hexapeptide. The invention also provides an expression vector comprising the nucleic acid molecule of the invention. The invention also provides a host cell comprising the nucleic acid molecule of the invention or the expression vector of the invention. According to a further aspect of the present invention there is provided the use of an acetyl hexapeptide according to the present invention or prepared by the method of preparation in the field of skin care products. According to a further aspect of the present invention there is provided a skin care product comprising an active ingredient and an acetyl hexapeptide according to the present invention or an acetyl hexapeptide prepared by a method of preparation according to the present invention. In some embodiments, the acetyl hexapeptide is present in the skin care product in an amount of 0.05-1% by mass, for example 0.05%, 0.06%, 0.07%, 0.08%, 0.09%, 1% or any value therebetween. In some embo