Derivatives of elastin-like polypeptides and uses thereof

1. A process for modulating the lower critical solution temperature of an elastin-like polypeptide comprising at least one methionine residue, said process comprising a thioether alkylation step of said elastin-like polypeptide.

2. A compound comprising at least one repetitive unit having the following formula (I):

wherein R is selected from the group consisting of:

(C 1 -C 22 )alkyl groups;

said alkyl groups being possibly substituted by one or several substituents selected from the group consisting of: OH, OR a , NR b R c , and NHC(O)R c ,

R a being selected from the group consisting of: (C 1 -C 10 )alkyl groups possibly interrupted by one or several heteroatom(s), (C 1 -C 10 )alkylene-(C 2 -C 10 )alkyne groups, (C 1 -C 10 )alkylene-(C 2 -C 10 )alkenyl groups, and (C 1 -C 10 )alkylene-X′ groups;

X′ representing a radical having the following formula:

R b and R c representing independently from each other H or a (C 1 -C 10 )alkyl group;

(C 1 -C 22 )alkylene-(C 6 -C 30 )aryl groups;

(C 6 -C 30 )aryl groups;

(C 2 -C 22 )alkyne groups; and

saccharides.

3. The compound of claim 2 , having the following formula (II):

wherein:

n is an integer varying from 1 to 200, and

A is selected from the group consisting of: H, acetyl, natural or unnatural amino acids, peptides, proteins and synthetic polymers; and

B is selected from the group consisting of: OH, NH 2 , NHAc, natural or unnatural amino acids, peptides, proteins, and synthetic polymers.

4. The compound of claim 3 , wherein A is selected from the group consisting of peptides and natural or unnatural amino acids.

5. The compound of claim 3 , wherein B is OH or is selected from the group consisting of peptides and natural or unnatural amino acids.

6. The compound of claim 2 , having the following formula (III):

wherein:

m is an integer varying from 1 to 200, and

A′ is a peptide comprising from 1 to 20 amino acids.

7. The compound of claim 2 , having the following formula (IV):

wherein:

p is an integer varying from 1 to 200, and

A″ is a peptide comprising from 1 to 20 amino acids.

8. The compound of claim 2 , wherein R is selected from the group consisting of:

(C 1 -C 22 )alkyl groups; and

(C 1 -C 22 )alkylene-phenyl groups.

9. The compound of claim 2 , wherein R is -A 1 -CH(OH)-A 2 -O-A 3 -A 4 , wherein:

A 1 is a (C 1 -C 4 )alkylene radical;

A 2 is a (C 1 -C 4 ) alkylene radical;

A 3 is a (C 1 -C 4 )alkylene radical or a —(CH 2 —CH 2 —O) i — group, i being an integer varying from 1 to 4, and

A 4 is a (C 1 -C 4 )alkylene radical or a (C 2 -C 4 )alkyne group.

10. The compound of claim 2 , wherein R is a (C 1 -C 4 )alkyl or benzyl group.

11. A thioether alkylation process for preparing a compound according to claim 2 , comprising a thioether alkylation step of an elastin-like polypeptide comprising at least one repetitive unit having the following formula (V):

said thioether alkylation step consisting in the reaction with an alkylation agent.

12. The thioether alkylation process of claim 11 , wherein the alkylation agent is a compound of formula (III) R—X, and X being a halogen atom, or a compound of formula (III-1):

wherein:

A 2 is a (C 1 -C 4 )alkylene radical;

A 3 is a (C 1 -C 4 )alkylene radical or a —(CH 2 —CH 2 —O) i — group, i being an integer varying from 1 to 4, and

A 4 is a (C 1 -C 4 )alkylene radical or a (C 2 -C 4 )alkyne group.

13. A process for modulating the lower critical solution temperature of an elastin-like polypeptide, said process comprising a thioether alkylation step of an elastin-like polypeptide comprising at least one repetitive unit having the following formula (V):

14. The process for modulating the lower critical solution temperature of claim 13 , wherein the thioether alkylation step consists in reacting the elastin-like polypeptide with a compound of formula (III) R—X, and X being a halogen atom, and R being selected from the group consisting of:

(C 1 -C 22 )alkyl groups;

said alkyl groups being possibly substituted by one or several substituents selected from the group consisting of: OH, OR a , NR b R c , and NHC(O)R c ,

R a being selected from the group consisting of: (C 1 -C 10 )alkyl groups possibly interrupted by one or several heteroatom(s), (C 1 -C 10 )alkylene-(C 2 -C 10 )alkyne groups, (C 1 -C 10 )alkylene-(C 2 -C 10 )alkenyl groups, and (C 1 -C 10 )alkylene-X′ groups;

X′ representing a radical having the following formula:

R b and R c representing independently from each other H or a (C 1 -C 10 )alkyl group;

(C 1 -C 22 )alkylene-(C 6 -C 30 )aryl groups;

(C 6 -C 30 )aryl groups;

(C 2 -C 22 )alkyne groups; and

saccharides.

15. A compound comprising at least one repetitive unit having the following formula (I′):

wherein:

X 1 is a counterion,

R is selected from the group consisting of:

(C 1 -C 22 )alkyl groups;

said alkyl groups being possibly substituted by one or several substituents selected from the group consisting of: OH, OR a , NR b R c , and NHC(O)R c ,

R a being selected from the group consisting of: (C 1 -C 10 )alkyl groups possibly interrupted by one or several heteroatom(s), (C 1 -C 10 )alkylene-(C 2 -C 10 )alkyne groups, (C 1 -C 10 )alkylene-(C 2 -C 10 )alkenyl groups, and (C 1 -C 10 )alkylene-X′ groups;

X′ representing a radical having the following formula:

R b and R c representing independently from each other H or a (C 1 -C 10 )alkyl group;

(C 1 -C 22 )alkylene-(C 6 -C 30 )aryl groups;

(C 6 -C 30 )aryl groups;

(C 2 -C 22 )alkyne groups; and

saccharides.

16. The compound of claim 15 , having the following formula (II′):

wherein:

X 1 is a counterion,

n is an integer varying from 1 to 200, and

A is selected from the group consisting of: H, acetyl, natural or unnatural amino acids, peptides, proteins and synthetic polymers; and

B is selected from the group consisting of: OH, NH 2 , NHAc, natural or unnatural amino acids, peptides, proteins, and synthetic polymers.