NOVEL PEPTIDES, USE THEREOF IN COSMETIC AND COSMECEUTIC APPLICATIONS, AND COMPOSITIONS COMPRISING SAME
申请人:Hocquaux Michel
公开号:US20100310484A1
公开(公告)日:2010-12-09
A peptide of formula I (SEQ ID NO: 1): Lip-A-Gly-His-B-R (I) wherein: Lip is a lipoyl residue of R or S configuration; A is absent or is a lysine residue of configuration L or D; GIy is a glycine residue; His is a histidine residue of configuration L or D; B is a lysine residue of configuration L or D, or a lysine residue of configuration L or D in which the NH2 group of the side chain comprises a modification, wherein said modification is (i) a replacement with a hydrogen or (ii) a modification with a protecting group selected from the group consisting of acetyl, benzoyl, tosyl, sulfonyl benzene, benzyloxycarbonyle and palmitoyl; wherein R is O(Z) or N(Z′)(Z′), and wherein Z, Z′ and Z′ are independently of each other a hydrogen or a protecting group selected from the group consisting of methyl, ethyl, propyl, phenyl, hexyl, decyl and hexadecyl, or a racemate, an enantiomer or a diastereomer thereof, or a mixture thereof, or a salt thereof. A peptide of formula II (SEQ ID NO: 2): Lip-A-His-B-C-Trp-R (II) wherein: Lip is a lipoyl residue of configuration R or S; His is a histidine residue of configuration L; Trp is a tryptophane residue of configuration L; A is absent, is an amino acid residue of configuration L or D selected from the group consisting of a lysine residue, an alanine residue, a glutamic acid residue and a glycine residue, or is a spacer of formula: NH—(CH2)n-CO— wherein n is an integer comprised between 2 and 14; B is an aromatic amino acid residue of configuration D selected from the group consisting of a phenylalanine residue, a homophenylalanine residue, a tryptophane residue, a β-(1-Naphthyl)-alanine residue, a β-(2-Naphthyl)-alanine residue and a phenylglycine residue; C is a basic amino acid residue of configuration L selected from the group consisting of an arginine residue, a lysine residue, an ornithine residue and a homoarginine residue; wherein R is O(Z) or N(Z′)(Z′),
序列编号为1的肽类分子式为I:Lip-A-Gly-His-B-R,其中:Lip是R或S构型的脂肪酰残基;A不存在或是L或D构型的赖
氨酸残基;Gly是甘
氨酸残基;His是L或D构型的组
氨酸残基;B是L或D构型的赖
氨酸残基,或是其侧链的NH2基团经修饰后的赖
氨酸残基,该修饰是(i)用氢原子替换或(ii)用保护基选自乙酰基、苯甲酰基、托磺基苯、苄氧羰基和棕榈酰基的保护基进行修饰;其中R是O(Z)或N(Z′)(Z′),Z、Z′和Z′独立地选自氢原子或选自甲基、乙基、丙基、苯基、己基、癸基和
十六烷基的保护基,或是它们的外消旋体、对映体或二对映异构体的混合物,或是其盐。
序列编号为2的肽类分子式为II:Lip-A-His-B-C-Trp-R,其中:Lip是R或S构型的脂肪酰残基;His是L构型的组
氨酸残基;Trp是L构型的色
氨酸残基;A不存在,是选自L或D构型的
氨基酸残基的赖
氨酸残基、丙
氨酸残基、谷
氨酸残基和甘
氨酸残基,或是分子式为NH—(
CH2)n-CO—,其中n为2至14之间的整数的间隔物;B是D构型的芳香族
氨基酸残基,选自苯丙
氨酸残基、同型苯丙
氨酸残基、色
氨酸残基、β-(1-
萘基)-丙
氨酸残基、β-(2-
萘基)-丙
氨酸残基和苯基甘
氨酸残基;C是L构型的碱性
氨基酸残基,选自精
氨酸残基、赖
氨酸残基、
鸟氨酸残基和同型精
氨酸残基;其中R是O(Z)或N(Z′)(Z′)。