Novel anti-aging peptides and cosmetic and/or pharmaceutical composition containing same

Abstract

Peptide compounds of general formula (I) R 1 -(AA) n -X 1 -Ser-Thr-Pro-X 2 -(AA) p -R 2 were developed that restore the circadian rhythm and resynchronize the biological clock of skin cells. Cosmetic or pharmaceutical compositions that include at least one peptide of general formula (I) in a cosmetically or dermatologically acceptable medium, and a cosmetic treatment method for restoring the circadian rhythm and resynchronising the biological clock of cells to reduce the dysfunctions caused by jet lag and/or nightshift work and/or to prevent or treat the cutaneous signs of aging were also developed.

1 . A peptide compound of general formula (I) below: 
       
         
           
                 
                 
               
                     
                   R 1 -(AA) n -X 1 -Ser-Thr-Pro-X 2 -(AA) p -R 2   
                 
             
                
               
            
           
         
         wherein 
         X 1  is a threonine, a serine or is equal to zero, 
         X 2  is an isoleucine, a leucine, a valine, an alanine, a glycine or is equal to zero, 
         AA is any amino acid except for proline or a derivative thereof, and n and p are integers between 0 and 4, 
         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, 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 3 to 13 amino acid residues, 
         said sequence of general formula (I) optionally comprising substitutions of amino acids X 1  and X 2  with other chemically equivalent amino acids, characterized in that the other chemically equivalent amino acids makes it possible to restore the circadian rhythm and resynchronize the biological clock of skin cells. 
       
     
     
         2 . The peptide compound according to  claim 1 , characterized in it is protected by an acetylation of the amino-terminal end. 
     
     
         3 . The peptide compound according to  claim 1 , characterized in that it corresponds to one of the following formulae: 
       
         
           
                 
                 
                 
               
                     
                   (SEQ ID no. 1) 
                   Tyr-Val-Ser-Thr-Pro-Tyr-Asn-NH 2   
                 
                     
                     
                 
                     
                   (SEQ ID no. 2) 
                   Val-Ser-Thr-Pro-Glu-NH 2   
                 
                     
                     
                 
                     
                   (SEQ ID no. 3) 
                   Ser-Thr-Pro-NH 2   
                 
                     
                     
                 
                     
                   (SEQ ID no. 4) 
                   Leu-His-Ser-Thr-Pro-NH 2   
                 
                     
                     
                 
                     
                   (SEQ ID no. 5) 
                   Arg-His-Ser-Thr-Pro-Glu-NH 2   
                 
                     
                     
                 
                     
                   (SEQ ID no. 6) 
                   His-Ser-Thr-Pro-Glu-NH 2 . 
                 
             
                
                
                
                
                
                
                
                
                
                
                
               
            
           
         
       
     
     
         4 . The peptide according to  claim 1 , wherein the peptide is characterized as a medicament. 
     
     
         5 . A cosmetic composition comprising:
 a peptide compound of general formula (I) below:   
       
         
           
                 
                 
               
                     
                   
                     R 1 -(AA) n -X 1 -Ser-Thr-Pro-X 2 -(AA) p -R 2   
                   
                 
             
                
               
            
           
         
         wherein 
         X 1  is a threonine, a serine or is equal to zero, 
         X 2  is an isoleucine, a leucine, a valine, an alanine, a glycine or is equal to zero, 
         AA is any amino acid except for proline or a derivative thereof, and n and p are integers between 0 and 4, 
         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, 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 3 to 13 amino acid residues, 
         said sequence of general formula (I) optionally comprising substitutions of amino acids X 1  and X 2  with other chemically equivalent amino acids, characterized in that the other chemically equivalent amino acids makes it possible to restore the circadian rhythm and resynchronize the biological clock of skin cells. 
       
     
     
         6 . The cosmetic composition according to  claim 5 , characterized in that it is present in a form adapted to topical application comprising a cosmetically acceptable medium. 
     
     
         7 . The composition according to  claim 5 , characterized in that said peptide compound is present in the composition at a concentration between approximately 0.0005 and 500 ppm. 
     
     
         8 . The composition according to  claim 5 , characterized in that 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. 
     
     
         9 . The composition according to  claim 5 , characterized in that it further contains at least one active ingredient promoting the action of said peptide compound. 
     
     
         10 . The composition according to  claim 9 , characterized in that said active ingredient is an anti-radical or anti-oxidant agent or an agent stimulating the synthesis of dermal macromolecules, or else an agent stimulating the energy metabolism. 
     
     
         11 . The peptide of  claim 1  wherein the peptide is a Clock activator active ingredient. 
     
     
         12 . The composition of  claim 5 , further comprising a cosmetically acceptable medium, wherein the composition restores the circadian rhythm and resynchronizes the biological clock of skin cells. 
     
     
         13 . The composition according to  claim 12 , characterized in that said composition makes it possible to activate cellular renewal and to stimulate cellular metabolism, makes it possible to reduce the dysfunctions caused by jet lag and/or nightshift work, makes it possible to prevent or treat the cutaneous signs of aging and to reduce the signs of skin fatigue, or prevents or combats the pathologies associated with dysfunctions of the circadian rhythm. 
     
     
         14 . (canceled) 
     
     
         15 . The composition according to  claim 12 , characterized in that said composition is in the form of a cosmetic night-time treatment. 
     
     
         16 - 17 . (canceled) 
     
     
         18 . A cosmetic treatment method for restoring the circadian rhythm and resynchronizing the biological clock of cells, 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 -(AA) n -X 1 -Ser-Thr-Pro-X 2 -(AA) p -R 2   
                   
                 
             
                
               
            
           
         
         wherein 
         X 1  is a threonine, a serine or is equal to zero, 
         X 2  is an isoleucine, a leucine, a valine, an alanine, a glycine or is equal to zero, 
         AA is any amino acid except for proline or a derivative thereof, and n and p are integers between 0 and 4, 
         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, 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 3 to 13 amino acid residues, 
         said sequence of general formula (I) optionally comprising substitutions of amino acids X 1  and X 2  with other chemically equivalent amino acids, characterized in that the other chemically equivalent amino acids makes it possible to restore the circadian rhythm and resynchronize the biological clock of skin cells. 
       
     
     
         19 . The cosmetic treatment method of  claim 18 , characterized in that the composition is applied before going to sleep so as to respect the circadian rhythm of the skin. 
     
     
         20 . The cosmetic treatment method of  claim 18 , characterized in that the composition is applied before going to sleep in order to prevent or treat the cutaneous signs of aging. 
     
     
         21 . The composition of  claim 7 , wherein the peptide compound is present at a concentration between 0.01 and 5 ppm. 
     
     
         22 . The composition according to  claim 5 , wherein the peptide compound is protected by an acetylation of the amino-terminal end. 
     
     
         23 . The composition according to  claim 5 , characterized in that the peptide compound corresponds to one of the following formulae: 
       
         
           
                 
                 
                 
               
                     
                   (SEQ ID no. 1) 
                   Tyr-Val-Ser-Thr-Pro-Tyr-Asn-NH 2   
                 
                     
                     
                 
                     
                   (SEQ ID no. 2) 
                   Val-Ser-Thr-Pro-Glu-NH 2   
                 
                     
                     
                 
                     
                   (SEQ ID no. 3) 
                   Ser-Thr-Pro-NH 2   
                 
                     
                     
                 
                     
                   (SEQ ID no. 4) 
                   Leu-His-Ser-Thr-Pro-NH 2   
                 
                     
                     
                 
                     
                   (SEQ ID no. 5) 
                   Arg-His-Ser-Thr-Pro-Glu-NH 2   
                 
                     
                     
                 
                     
                   (SEQ ID no. 6) 
                   His-Ser-Thr-Pro-Glu-NH 2 .