HIGHLY BRANCHED ALPHA-D-GLUCANS

• US 20150080220A1
• Filed: 04/19/2013
• Published: 03/19/2015
• Est. Priority Date: 04/19/2012
• Status: Active Grant

• Current Assignee: Phytoption LLC, Purdue Research Foundation (The Trustees of Purdue University (d/b/a Purdue University))
• Original Assignee: Purdue Research Foundation (The Trustees of Purdue University (d/b/a Purdue University))
• Inventors: Yao, Yuan, Zhang, Jingmin
• Granted Patent: US 10,117,937 B2
• Time in Patent Office: Days
• US Class Current: 504/358
• CPC Class Codes: A61K 2800/49 Solubiliser, Solubilising system
• CPC Class Codes: A61K 2800/544 Dendrimers, Hyperbranched polymers
• CPC Class Codes: A61K 31/192 having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid cannabinoids A61K31/658
• CPC Class Codes: A61K 31/343 condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
• CPC Class Codes: A61K 47/36 Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
• CPC Class Codes: A61K 8/73 Polysaccharides
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 31/10 Antimycotics
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: C08B 37/0009 alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof

Abstract

Compositions including a highly branched alpha-D-glucan or modified forms thereof and a solute compound are described herein. The compositions can provide increased water solubility and/or increased rate of dissolution for the solute compound. The compositions can also provide increased stability for the solute compound. Methods for preparing and using compositions including a solute compound and a highly branched alpha-D-glucan are also described.

Claims

1. A composition for increasing solubility of a solute compound, comprising:

a highly branched alpha-D-glucan or a modified form thereof; and

a solute compound having an aqueous solubility that is greater than the aqueous solubility of the solute compound in the absence of the highly branched alpha-D-glucan.

2. The composition of claim 1, wherein the highly branched alpha-D-glucan has a percentage branch density greater than about 7%.

3. The composition of claim 1, wherein the highly branched alpha-D-glucan has a dendritic structure.

4. The composition of claim 1, wherein the highly branched alpha-D-glucan is glycogen, phytoglycogen, or a modified form thereof.

5. The composition of claim 1, wherein the rate of dissolution of the solute compound in aqueous solvent is greater than the rate of dissolution of the solute compound in the absence of the highly branched alpha-D-glucan.

6. The composition of claim 1, wherein the solubility is increased by at least about a factor of two relative to the solubility of the solute compound in the absence of the highly branched alpha-D-glucan.

7. The composition of claim 1, wherein the highly branched alpha-D-glucan is a modified highly branched alpha-D-glucan.

8. The composition of claim 7, wherein the modified highly branched alpha-D-glucan contains at least a chemical group selected from acetate, phosphate, octenyl succinate, succinate, hydroxypropyl, hydroxyethyl, cationic groups, carboxymethyl, polyethylene glycol (PEG, or polyethylene oxide), polypropylene glycol (or polypropylene oxide), or a combination thereof.

9. The composition of claim 7, wherein the modified highly branched alpha-D-glucan contains at least one group selected from antibody, antigen, aptamer, protein, peptide, amino acid, cyclodextrin, saccharide, lipid, nucleic acid and nucleotide, dendrimer, enzyme, fluorescent group or dye, magnetic group, metal ion, metal nanoparticle, quantum dot, polymer and block co-polymer, radioactive group, or a combination thereof.

10. The composition of claim 7, wherein the modified highly branched alpha-D-glucan is prepared by at least one treatment selected from acid hydrolysis, oxidation, pyrodextrinization, enzymatic treatment using alpha-amylase, beta-amylase, debranching enzymes, transglucosidase, amyloglucosidase, and/or protease, bleaching, shear force treatment, extrusion, kneading, homogenization, hydrothermal processing, dry heating, microwave treatment, radiation, or a combination thereof.

11. The composition of claim 1, wherein the solute compound is a hydrophobic compound.

12. The composition of claim 1, wherein the solute compound is a phenolic compound.

13. The composition of claim 1, wherein the solute compound is selected from the group consisting of carotenoids, curcuminoids, flavonoids, sterols, phytosterols, saponins, and sapogenins.

14. The composition of claim 1, wherein the solute compound is selected from the group consisting of drugs, vitamins, pesticides, herbicides, anti-oxidants, herb extracts, Chinese medicine, coloring agents, hormones, essential oils, or a combination thereof.

15. The composition of claim 1, wherein the solute compound is selected from the group consisting of curcumin, quercetin, lutein, resveratrol, lecithin, thymol, paclitaxel, ibuprophen, and griseofulvin.

16. The composition of claim 1, wherein the composition is prepared using a method comprising the steps of:

dissolving or dispersing at least one solute compound in a first solvent to form a first solution or dispersion;

dissolving or dispersing at least one highly branched alpha-D-glucan or a modified form thereof in a second solvent to form a second solution or dispersion;

mixing the first and second solutions or dispersions together to form a mixture; and

removing the solvent from the mixture to obtain a composition;

wherein the water solubility of the solute compound in the composition is greater than the water solubility of the solute compound in the absence of the at least one highly branched alpha-D-glucan.

17. The composition of claim 16, wherein the method increases the rate of dissolution and/or the stability of the solute compound.

18. The composition of claim 16, further comprising the step of processing the mixture by kneading, extrusion, homogenization, ultrasonic, high-pressure treatment, high-speed treatment, microwave treatment, radiation treatment, heat treatment, or a combination thereof.

19. The composition of claim 16, wherein the solvent is removed from the mixture by spray drying, vacuum drying, freeze drying, drum drying, extrusion, supercritical extraction, or a combination thereof.

20. The composition of claim 1, wherein the composition further comprises other ingredients, including but not limited to pharmaceutically acceptable carriers.

21. The compositions of claim 1, wherein the solute compound and the highly branched alpha-D-glucan are provided in a mass ratio ranging from about 100:

1 to about 1;

1000 of solute compound compared to highly branched alpha-D-glucan.

22. A method of increasing the solubility, the rate of dissolution, and/or the stability of a solute compound, comprising the steps of combining at least one highly branched alpha-D-glucan or a modified form thereof with the solute compound.

23. The method of claim 22, wherein the combination is in the presence of at least a solvent.

24. The method of claim 22, further comprising the step of processing the mixture by kneading, extrusion, homogenization, ultrasonic, high-pressure treatment, high-speed treatment, microwave treatment, radiation treatment, heat treatment, or a combination thereof.

25. The method of claim 23, wherein the solvent is removed from the mixture by spray drying, vacuum drying, freeze drying, drum drying, heat drying, extrusion, supercritical extraction, or a combination thereof.

26. A modified phytoglycogen or glycogen material containing at least a chemical group of polyethylene glycol (PEG) or polyethylene oxide (PEO).

27. The material in claim 26, wherein the material further contains a chemical group selected from acetate, phosphate, octenyl succinate, succinate, hydroxypropyl, hydroxyethyl, cationic groups, carboxymethyl, polypropylene glycol (or polypropylene oxide), or a combination thereof.

28. The material in claim 26, wherein the material improves a property of a solute compound, wherein the property includes the aqueous solubility, rate of dissolution, and/or stability against crystallization, oxidation, degradation, deterioration, reduction, or structure change, or a combination thereof.