Amphiphilic polymer
The present application relates to a micelle comprising a drug encapsulated by an amphiphilic polymer and a composition comprising the same. The micelle of the present application has an excellent dispersion property on an aqueous solution and a superior percutaneous absorption characteristic on preparing a formulation.
1. A micelle comprising:
a drug; and
an amphiphilic polymer which encapsulates said drug, has a first block (A) and a second block (B) that is phase-separated with said first block (A) and comprises a polymerization unit (B1) of an acrylic monomer or a vinylic monomer having a solubility parameter of a single polymer of less than 10.0 (cal/cm 3 ) 1/2 and a polymerization unit (B2) of a polymerizable monomer having a functional group being capable of forming a hydrogen bond,
wherein the first block (A) comprises a polymer having a solubility parameter of 10 (cal/cm 3 ) 1/2 or more,
wherein a weight ratio (B1:B2) of the polymerization unit (B1) of an acrylic monomer or a vinylic monomer having a solubility parameter of a single polymer of less than 10.0 (cal/cm 3 ) 1/2 and the polymerization unit (B2) of a polymerizable monomer having a functional group being capable of forming a hydrogen bond, in the second block (B), is in a range of 1:9 to 9:1,
wherein the drug includes intramolecular —H, wherein the intramolecular —H forms a hydrogen bond with the functional group of polymerization unit (B2) in the second block (B) of the amphiphilic polymer.
2. The micelle according to claim 1 , wherein the drug comprises a physiologically active substance.
3. The micelle according to claim 2 , wherein the physiologically active substance is sparingly soluble.
4. The micelle according to claim 3 , wherein the sparingly soluble and physiologically active substance is any one selected from the group consisting of genistein, daidzein, cucurbitasin, prangenidin or a derivative thereof; a polyphenol; or a mixture thereof.
5. The micelle according to claim 4 , wherein the sparingly soluble and physiologically active substance is genistein or a glycoside of said genistein.
6. The micelle according to claim 1 , wherein the first block (A) is any one selected from the group consisting of polyethylene glycol, a polyethylene glycol-propylene glycol copolymer, polyvinyl pyrrolidone and polyethyleneimine.
7. The micelle according to claim 1 , wherein
the acrylic monomer is represented by Formula 1 or Formula 2 below:
where, Q in Formula 1 and 2 is hydrogen or an alkyl group, B in Formula 1 is a straight or branched alkyl group having at least one carbon atom, an alicyclic hydrocarbon group, an aromatic substituent or a carboxyl group, and R 1 and R 2 in Formula 2 are each independently hydrogen, a straight or branched alkyl group having at least one carbon atom, an alicyclic hydrocarbon group, or an aromatic substituent.
8. The micelle according to claim 7 , wherein
Q in Formula 1 is hydrogen or an alkyl group having 1 to 4 carbon atoms, B is an alkyl group having at least one carbon atom or an alicyclic hydrocarbon group having 6 to 12 carbon atoms.
9. The micelle according to claim 1 , wherein
the vinylic monomer is represented by Formula 3 or Formula 4 below:
where, X is a nitrogen atom or an oxygen atom, Y is a carbonyl group or a single bond, R 3 and R 5 are each independently hydrogen or an alkyl group, or R 3 and R 5 are linked together to form an alkylene group, and R 4 is an alkenyl group (provided that R 3 is not present, if X is an oxygen atom);
where, R 6 , R 7 and R 8 are each independently hydrogen or an alkyl group, and R 9 is a cyano group or an aromatic substituent.
10. The micelle according to claim 1 , wherein
the functional group is a hydroxyl group, an amine group, a nitro group, an amino group, an imide group, an alkoxysilane group or a cyano group.
11. The micelle according to claim 1 , wherein
the amphiphilic polymer has a block ratio (A:B) of the first block (A) and the second block (B) different from each other.
12. The micelle according to claim 11 , wherein
the block ratio (A:B) of the first block (A) and the second block (B) in the amphiphilic polymer is 1:9 to 9:1.
13. The micelle according to claim 1 , wherein
the block ratio (A:B) of the first block (A) and the second block (B) in the amphiphilic polymer is 3:7 to 7:3.
14. The micelle according to claim 1 , wherein
the second block of the amphiphilic polymer is adjacent to the drug.
15. The micelle according to claim 1 , wherein
the average particle diameter is in a range of 1 to 10,000 nm.
16. A composition for preparing particles comprising the micelle of claim 1 .
17. A pharmaceutical or cosmetic composition comprising the micelle of claim 1 .
18. The pharmaceutical or cosmetic composition according to claim 17 , wherein the composition is in a water-in-oil type emulsion form or an oil-in-water type emulsion form.
19. A process for preparing the micelle of claim 1 comprising:
a step of polymerizing a polymer forming a first block (A) and an acrylic monomer or a vinylic monomer having a solubility parameter of a single polymer of less than 10.0 (cal/cm 3 ) 1/2 to prepare an amphiphilic polymer; and
a step of mixing said amphiphilic polymer and a drug.