HMG-CoA reductase derived peptide and cosmetic or pharmaceutical composition containing same
View Patent ↗The present invention relates to a peptide of general formula (I): R 1 -(AA) n -X 1 -Gly-Glu-Leu-Ser-X 2 -X 3- (AA) p -R 2 , derived from human HMG-CoA reductase. The present invention also relates to a cosmetic or pharmaceutical composition comprising at least one peptide of general formula (I), in a physiologically suitable medium. The present invention further relates to the use of this novel peptide as an active principle that activates human HMG-CoA reductase in a cosmetic composition intended to strengthen the barrier function of the skin and to stimulate epidermal differentiation. The invention further applies to a cosmetic treatment method intended to prevent and/or combat the external stresses and signs of cutaneous aging.
1. A peptide derived from human HMG-CoA reductase, of general formula (I)
R 1 -(AA) n -X 1 -Gly-Glu-Leu-Ser-X 2 -X 3 -(AA) p -R 2
in which,
X 1 is alanine, valine or isoleucine,
X 2 is leucine, isoleucine or absent,
X 3 is methionine, serine, alanine or absent,
AA represents any amino acid, and n and p are integers between 0 and 4, with the proviso that when X 2 and X 3 are no amino acid, p is 0,
R 1 represents the primary amine function of the N-terminal amino acid, free or substituted by a protecting group selected from an acetyl group, a benzoyl group, a tosyl group or a benzyloxycarbonyl group,
R 2 represents the hydroxyl group of the carboxyl function of the C-terminal amino acid, free or substituted by a protecting group selected from an alkyl chain from C 1 to C 20 , or an NH 2 , NHY or NYY group with Y representing an alkyl chain from C 1 to C 4 .
2. The peptide according to claim 1 , wherein the peptide is selected from the group consisting of
(SEQ ID No. 1)
Met-Ala-Gly-Glu-Leu-Ser-Leu-Met-Ala-Ala,
(SEQ ID No. 2)
Gly-Val-Gly-Glu-Leu-Ser-Ile-Ser-Ala,
(SEQ ID No. 3)
Ile-Gly-Glu-Leu-Ser-Leu-Ala-Ala,
(SEQ ID No. 4)
Ala-Gly-Glu-Leu-Ser,
(SEQ ID No. 5)
Ala-Gly-Glu-Leu-Ser-NH 2 ,
(SEQ ID No. 6)
Ile-Gly-Glu-Leu-Ser,
and
(SEQ ID No. 7)
Ile-Gly-Glu-Leu-Ser-NH 2 .
3. The peptide according to claim 2 , wherein the peptide corresponds to the SEQ ID No. 4 sequence.
4. The peptide according to claim 2 , wherein the peptide corresponds to the SEQ ID No. 5 sequence.
5. The peptide according to claim 1 , wherein the peptide is solubilized in one or more physiologically acceptable solvents selected from the group consisting of water, glycerol, ethanol, propylene glycol, butylene glycol, dipropylene glycol, ethoxylated diethylene glycol or propoxylated diethylene glycol, cyclic polyols, white petroleum jelly, vegetable oil and combinations thereof.
6. The peptide according to claim 1 , wherein the peptide is characterized as a medication.
7. A cosmetic or pharmaceutical composition comprising:
At least one peptide derived from human HMG-CoA reductase, of general formula (I)
R 1 -(AA) n -X 1 -Gly-Glu-Leu-Ser-X 2 -X 3 -(AA) p -R 2
in which,
X 1 is alanine, valine or isoleucine,
X 2 is leucine, isoleucine or absent,
X 3 is methionine, serine, alanine or absent,
AA represents any amino acid, and n and p are integers between 0 and 4, with the proviso that when X 2 and X 3 are no amino acid, p is 0,
R 1 represents the primary amine function of the N-terminal amino acid, free or substituted by a protecting group selected from an acetyl group, a benzoyl group, a tosyl group or a benzyloxycarbonyl group,
R 2 represents the hydroxyl group of the carboxyl function of the C-terminal amino acid, free or substituted by a protecting group selected from an alkyl chain from C 1 to C 20 , or an NH 2 , NHY or NYY group with Y representing an alkyl chain from C 1 to C 4 ; and
a physiologically acceptable medium;
wherein the peptide is present in the medium, as an active principle that activates human HMG-CoA reductase, alone or in combination with at least one other anti-aging active principle.
8. The composition according to claim 7 , wherein said peptide is present at a concentration of between 0.0005 and 500 ppm.
9. The composition according to claim 8 , wherein said peptide is present at a concentration of between 0.01 and 5 ppm.
10. The composition according to claim 7 , wherein the composition is a topically administrable composition.
11. The composition according to claim 7 , wherein the composition strengthens the barrier function of the epidermis and stimulates epidermal differentiation.
12. The composition according to claim 7 , wherein the composition prevents and combats the cutaneous signs of aging and photoaging.
13. The composition according to claim 7 , wherein the composition protects the skin from external stresses.
14. The composition according to claim 7 , wherein the composition treats pathologies characterized by an alteration in the barrier function, selected from the group consisting of hypersensitive, irritated or reactive skin and atopic eczema.
15. A method for the treatment of external aggressions or cutaneous signs of aging and photoaging, the method comprising:
topically applying, to the skin to be treated, a composition comprising an effective quantity of a peptide derived from human HMG-CoA reductase, of general formula (I)
R 1 -(AA) n -X 1 -Gly-Glu-Leu-Ser-X 2 -X 3 -(AA) p -R 2
in which,
X 1 is alanine, valine or isoleucine,
X 2 is leucine, isoleucine or absent,
X 3 is methionine, serine, alanine or absent,
AA represents any amino acid, and n and p are integers between 0 and 4, with the proviso that when X 2 and X 3 are no amino acid, p is 0,
R 1 represents the primary amine function of the N-terminal amino acid, free or substituted by a protecting group selected from an acetyl group, a benzoyl group, a tosyl group or a benzyloxycarbonyl group,
R 2 represents the hydroxyl group of the carboxyl function of the C-terminal amino acid, free or substituted by a protecting group selected from an alkyl chain from C 1 to C 20 , or an NH 2 , NHY or NYY group with Y representing an alkyl chain from C 1 to C 4 .
16. The method according to claim 15 , wherein the peptide is solubilized in one or more physiologically suitable solvents selected from the group consisting of water, glycerol, ethanol, propanediol, propylene glycol, butylene glycol, dipropylene glycol, ethoxylated diethylene glycol or propoxylated diethylene glycol, cyclic polyols, white petroleum jelly, vegetable oil, and combinations thereof.
17. The method according to claim 15 , wherein the peptide is present at a concentration of between 0.0005 and 500 ppm.
18. The method according to claim 15 , wherein the peptide is present at a concentration of between 0.01 and 5 ppm.
19. The method according to claim 15 , wherein the peptide is selected from the group consisting of:
(SEQ ID No. 1)
Met-Ala-Gly-Glu-Leu-Ser-Leu-Met-Ala-Ala
(SEQ ID No. 2)
Gly-Val-Gly-Glu-Leu-Ser-Ile-Ser-Ala
(SEQ ID No. 3)
Ile-Gly-Glu-Leu-Ser-Leu-Ala-Ala
(SEQ ID No. 4)
Ala-Gly-Glu-Leu-Ser
(SEQ ID No. 5)
Ala-Gly-Glu-Leu-Ser-NH 2
(SEQ ID No. 6)
Ile-Gly-Glu-Leu-Ser
(SEQ ID No. 7)
Ile-Gly-Glu-Leu-Ser-NH 2 .
20. The composition according to claim 7 , wherein the peptide is selected from the group consisting of
(SEQ ID No. 1)
Met-Ala-Gly-Glu-Leu-Ser-Leu-Met-Ala-Ala,
(SEQ ID No. 2)
Gly-Val-Gly-Glu-Leu-Ser-Ile-Ser-Ala,
(SEQ ID No. 3)
Ile-Gly-Glu-Leu-Ser-Leu-Ala-Ala,
(SEQ ID No. 4)
Ala-Gly-Glu-Leu-Ser,
(SEQ ID No. 5)
Ala-Gly-Glu-Leu-Ser-NH 2 ,
(SEQ ID No. 6)
Ile-Gly-Glu-Leu-Ser,
and
(SEQ ID No. 7)
Ile-Gly-Glu-Leu-Ser-NH 2 .