Anti-aging peptides and cosmetic and/or pharmaceutical composition containing same

1. A peptide compound of general formula (I) below:

R 1 -X 1 -X 2 -Ser-Pro-Leu-Gln-X 3 -X 4 -R 2

wherein

X 1 is a cysteine, a methionine or is equal to zero,

X 2 is a serine, a threonine, or is equal to zero,

X 3 is an alanine, a glycine, an isoleucine, a leucine, a proline, a valine or is equal to zero,

X 4 is an asparagine, a glutamine, or is equal to zero,

R 1 is the primary amine function of the N-terminal amino acid, either free or substituted by a protective group which can be selected from an acetyl group, a benzoyl group, a tosyl group or a benzyloxycarbonyl group,

R 2 is the hydroxyl group of the carboxyl function of the C-terminal amino acid, either free or substituted by a protective group which can be selected from a C 1 to C 20 alkyl chain or a NH 2 , NHY or NYY group where Y is a C 1 to C 4 alkyl chain.

2. The peptide compound according to claim 1 , wherein said peptide of general formula (I) comprises at least one protective group protecting at least one functional group, said protective group selected from an acetylation of the amino-terminal end or an amidation or esterification of the carboxy-terminal end, or both.

3. The peptide compound according to claim 1 , wherein said peptide is selected from the group consisting of

(SEQ ID no. 1)

Ser-Pro-Leu-Gln-NH 2

(SEQ ID no. 2)

Thr-Ser-Pro-Leu-Gln

(SEQ ID no. 3)

Ser-Ser-Pro-Leu-Gln-Leu-NH 2

(SEQ ID no. 4)

Ser-Ser-Pro-Leu-Gln-Ala-Asn-NH 2 .

4. A cosmetic composition comprising;

a peptide compound of general formula (I) below:

R 1 -X 1 -X 2 -Ser-Pro-Leu-Gln-X 3 -X 4 -R 2

wherein

X 1 is a cysteine, a methionine or is equal to zero,

X 2 is a serine, a threonine, or is equal to zero,

X 3 is an alanine, a glycine, an isoleucine, a leucine, a proline, a valine or is equal to zero,

X 4 is an asparagine, a glutamine, or is equal to zero,

R 1 is the primary amine function of the N-terminal amino acid, either free or substituted by a protective group which can be selected from an acetyl group, a benzoyl group, a tosyl group or a benzyloxycarbonyl group,

R 2 is the hydroxyl group of the carboxyl function of the C-terminal amino acid, either free or substituted by a protective group which can be selected from a C 1 to C 20 alkyl chain or a NH 2 , NHY or NYY group where Y is a C 1 to C 4 alkyl chain,

said sequence of general formula (I) being formed of 4 to 8 amino acid residues.

5. The cosmetic composition according to claim 4 , wherein said peptide is in a form adapted for topical application and comprises cosmetically acceptable medium.

6. The composition according to claim 4 , wherein said peptide compound is present in the composition at a concentration between approximately 0.0005 and 500 parts per million (ppm).

7. The composition according to claim 4 , wherein said peptide is solubilized in one or more solvents selected from the group consisting of water, glycerol, ethanol, propylene glycol, butylene glycol, dipropylene glycol, ethoxylated or propoxylated diglycols, cyclic polyols, petroleum jelly, a vegetable oil, and combinations thereof.

8. A cosmetic treatment method for treating the cutaneous signs of aging or to protect the skin against the harmful effects caused by ultraviolet (UV) radiation, the method comprising:

topically applying, to skin or skin appendages to be treated, a composition comprising an effective quantity of a peptide compound of general formula (I) below:

R 1 -X 1 -X 2 -Ser-Pro-Leu-Gln-X 3 -X 4 -R 2

wherein

X 1 is a cysteine, a methionine or is equal to zero,

X 2 is a serine, a threonine, or is equal to zero,

X 3 is an alanine, a glycine, an isoleucine, a leucine, a proline, a valine or is equal to zero,

X 4 is an asparagine, a glutamine, or is equal to zero,

R 1 is the primary amine function of the N-terminal amino acid, either free or substituted by a protective group which can be selected from an acetyl group, a benzoyl group, a tosyl group or a benzyloxycarbonyl group,

R 2 is the hydroxyl group of the carboxyl function of the C-terminal amino acid, either free or substituted by a protective group which can be selected from a C 1 to C 20 alkyl chain or a NH 2 , NHY or NYY group where Y is a C 1 to C 4 alkyl chain,

said sequence of general formula (I) being formed of 4 to 8 amino acid residues.

9. The cosmetic treatment method of claim 8 , wherein topically applying includes applying the composition before going to sleep.

10. The composition of claim 6 , wherein the peptide compound is present at a concentration between 0.01 and 5 parts per million (ppm).

11. The composition according to claim 4 , wherein the peptide compound of general formula (I) comprises at least one protective group protecting at least one functional group, said protective group selected from an acetylation of the amino-terminal end or an amidation or esterification of the carboxy-terminal end, or both.

12. The composition of claim 4 , wherein the peptide compound is selected from the group consisting of

(SEQ ID no. 1)

Ser-Pro-Leu-Gln-NH 2

(SEQ ID no. 2)

Thr-Ser-Pro-Leu-Gln

(SEQ ID no. 3)

Ser-Ser-Pro-Leu-Gln-Leu-NH 2

(SEQ ID no. 4)

Ser-Ser-Pro-Leu-Gln-Ala-Asn-NH 2 .

13. The method of claim 8 , wherein the peptide of general formula (I) comprises at least one protective group protecting at least one functional group, said protective group selected from an acetylation of the amino-terminal end or an amidation or esterification of the carboxy-terminal end, or both.

14. The method of claim 8 , wherein the peptide compound is selected from the group consisting of

(SEQ ID no. 1)

Ser-Pro-Leu-Gln-NH 2

(SEQ ID no. 2)

Thr-Ser-Pro-Leu-Gln

(SEQ ID no. 3)

Ser-Ser-Pro-Leu-Gln-Leu-NH 2

(SEQ ID no. 4)

Ser-Ser-Pro-Leu-Gln-Ala-Asn-NH 2 .