Curcuminoid complexes with enhanced stability, solubility and/or bioavailability

Patent metadata

Field	Value
Publication number	US-9504754-B2
Application number	US-201414213063-A
Country	US
Kind code	B2
Filing date	Mar 14, 2014
Priority date	Mar 15, 2013
Publication date	Nov 29, 2016
Grant date	Nov 29, 2016

Abstract

Methods and materials relating to a medicament preparation comprising a curcuminoid component and a euradit component provided as a curcuminoid-eudragit complex, which enhance the bioavailability of the curcumin component and are useful for the treatment of various diseases including cancer, neurodegeneration, inflammation, and immunodeficiency. In some aspects, the curcuminoid component comprises curcumin to prepare a curcumin-eudragit complex and a medicament comprising curcumin-eudragit complexes.

First claim

What is claimed is:

1. A curcuminoid composition comprising:
a curcuminoid-polymer complex comprising at least one curcuminoid component selected from the group consisting of curcumin, demethoxycurcumin, bisdemethoxycurcumin, tetrahydroxycurcumin, Bis-0-Demethyl curcumin (BDMC), or combinations thereof;
at least one polymer or co-polymer component having a backbone comprising polymethacrylate or methyl methacrylate; and
surfactant component,
wherein the curcuminoid component and the polymer or co-polymer component are in the form of the curcuminoid-polymer complex having a plurality of particles with an average particle size between about 10.0 nm and about 5000.0 nm; and
wherein the curcuminoid-polymer complex is formed by a process comprising:
dissolving the curmuminoid component and the polymer or co-polymer component in an organic solvent to form a curmuminoid-polymer solution;
adding the curmuminoid-polymer solution to an aqueous solution having the surfactant to to precipitated the curcuminoid-polymer complex and form a dispersion; and
removing the organic solvent from the dispersion to collect the curcumoid-polymer complex.

2. The curcuminoid composition of claim 1 , wherein the curcuminoid component comprises curcumin.

3. The curcuminoid composition of claim 2 , wherein the complex presents an aqueous solubility of the curcumin in an amount greater than about 1 μg/ml.

4. The curcuminoid composition of claim 1 , wherein the aqueous solubility is between about 1 μg/ml and about 50 mg/ml.

5. The curcuminoid composition of claim 1 , wherein the polymer or co-polymer component is chosen such that the aqueous solubility of the curcuminoid component is greater than about 1 μg/ml at a pH between about 1.0 and about 5.0.

6. The curcuminoid composition of claim 1 , wherein the polymer or co-polymer component is chosen such that the aqueous solubility of the curcuminoid component is greater than about 1 μg/ml at a pH between about 5.0 and about 14.0.

7. The curcuminoid composition of claim 1 , comprising a first polymer or co-polymer component and a second polymer or co-polymer component, the first polymer or co-polymer forming a first complex and the second polymer or co-polymer forming a second complex, wherein the first polymer or co-polymer component is chosen such that the aqueous solubility of the curcuminoid component of the first complex is greater than about 1 μg/ml at a pH between about 1.0 and about 5.0, and wherein the second polymer or co-polymer component is chosen such that the aqueous solubility of the curcuminoid component of the second complex is greater than about 1 μg/ml at a pH between about 5.5 and about 14.0.

8. The curcuminoid composition of claim 1 , wherein a weight ratio of the curcuminoid component to the polymer or co-polymer component is between about 1:0.1 to about 1:50.

9. The curcuminoid composition of claim 1 , wherein the complex increases the stability of the curcuminoid component in an aqueous solution compared to free curcumin.

10. The curcuminoid composition of claim 1 , further comprising at least one adjuvant.

11. The curcuminoid composition of claim 1 , wherein the complex is in the form chosen from a solid, a liquid or a semisolid.

12. A method of forming a plurality of particles comprising a curcuminoid-polymer complex, the method comprising:
dissolving at least one curcuminoid component and at least one polymer or co-polymer component in an organic solvent to form a solution having the curcuminoid-polymer complex, the polymer component comprising a polymer or co-polymer having a backbone comprising polymethacrylate or methyl methacrylate;
adding the solution containing the curcuminoid-polymer complex to an aqueous solution containing a surfactant to form the plurality of particles comprising the curcuminoid-polymer complex;
removing the organic solvent from the aqueous solution comprising the curcuminoid-polymer complex particles;
separating the curcuminoid-polymer complex particles from the aqueous solution.

13. The method of claim 12 , wherein an aqueous solubility of the curcuminoid component of the curcuminoid-polymer complex particles in an aqueous solution is between about 1 μg/ml and about 50 mg/ml at a pH between about 1.0 and about 14.0.

14. The method of claim 12 , further comprising adding at least one adjuvant to the organic solvent, wherein the curcuminoid-polymer complex particles comprise the at least one adjuvant.

15. The method of claim 12 , further comprising adding a surfactant to the aqueous solution prior to the step of adding the solution containing the curcuminoid-polymer complex to the aqueous solution.

16. The method of claim 12 , wherein the curcuminoid component comprises curcumin.

17. A medicament preparation providing enhanced curcuminoid stability, aqueous solubility and/or bioavailability, the medicament preparation comprising:
at least one curcuminoid component, at least one polymer or co-polymer component and a surfactant in the form of a curcuminoid-polymer complex, the at least one curcuminoid component selected from the group consisting of curcumin, demethoxycurcumin, bisdemethoxycurcumin, tetrahydroxycurcumin, Bis-0-Demethyl curcumin (BDMC), or combinations thereof and the at least one polymer or co-polymer component having a backbone comprising polymethacrylate or methyl methacrylate, wherein the curcuminoid component and the polymer or co-polymer component are provided as the curcuminoid-polymer complex having a plurality of particles with an average particle size between about 10.0 nm and about 5000.0 nm, and wherein the curcuminoid-polymer complex enhances a stability, an aqueous solubility and/or bioavailability of the curcuminoid component compared to a free curcuminoid component when the curcuminoid component and the free curcuminoid component are the same curcuminoid component; and wherein the curcuminoid-polymer complex is formed by a process comprising dissolving the curcuminoid component and the polymer or co-polymer component in an organic solvent to form a curcuminoid-polymer solution, adding the curcuminoid-polymer solution to an aqueous solution having the surfactant to precipitate the curcuminoid-polymer complex and form a dispersion, and removing the organic solvent from the dispersion to collect the curcuminoid-polymer complex.

18. The medicament preparation of claim 17 , wherein the curcuminoid component comprises curcumin.

19. The medicament preparation of claim 17 , wherein the solubility of the curcuminoid component of the complex in an aqueous solution is between about 1 μg/ml and about 50 mg/ml at a pH between about 1.0 and about 5.0.

20. The medicament preparation of claim 17 , wherein the solubility of the curcuminoid component of the complex in an aqueous solution is between about 1 μg/ml and about 50 mg/ml at a pH between about 5.5 and about 14.0.

21. The medicament preparation of claim 17 , wherein a weight ratio of the curcuminoid component to the polymer or co-polymer component is between about 1:0.1 to about 1:50.

22. The medicament preparation of claim 17 , further comprising at least one surfactant in a concentration between about 1.0% and about 20.0%, weight to volume.

23. The medicament preparation of claim 17 , further comprising at least one adjuvant.

24. The medicament preparation of claim 17 , wherein the medicament preparation is in the form of a solid, a liquid, or a semisolid.

Assignees

• South Dakota Board Of Regents

Inventors

• Tummala Hemachand
• Kumar Sunny

Classifications

• A61K31/12 Primary

  Ketones · CPC title

• A61K47/48176 Primary

  Human Necessities · mapped topic

• A61K47/58 Primary

  obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin · CPC title