# US 12,109,217 B2 · Bioactive agents included in functionalized starch having a single helix V-structure

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- Number: US 12,109,217 B2
- Document ID: US12109217B2
- Status: Granted
- Kind: B2
- Application number: 15/121,993
- Filed: 2015-02-25
- Published: 2017-03-16
- Granted: 2024-10-08
- Earliest claimed: 2014-02-27
- Assignees: B-Organic Films Corp.
- Applicants: B-Organic Films Corp.
- Inventors: Tien Canh Le; Mircea-Alexandru Mateescu
- Web page: https://patentgrep.com/patent/US12109217B2

## CPC

- A61K 31/593: 9,10-Secocholestane derivatives, e.g. cholecalciferol, i.e. vitamin D3
- A01N 33/12: Quaternary ammonium compounds
- A23D 9/007: characterised by ingredients other than fatty acid triglycerides
- A23L 29/219: Chemically modified starch; Reaction or complexation products of starch with other chemicals
- A23L 33/10: using additives (addition of substantially indigestible substances A23L33/21)
- A23L 33/105: Plant extracts, their artificial duplicates or their derivatives
- A23L 33/12: Fatty acids or derivatives thereof
- A23L 33/155: Vitamins A or D
- A23P 10/40: free-flowing powder or instant powder, i.e. powder which is reconstituted rapidly when liquid is added (A23P10/20, A23P10/30 take precedence)
- A61K 8/022: {Powders; Compacted Powders}
- A61K 8/347: {Phenols}
- A61K 8/35: Ketones, e.g. benzophenone
- A61K 8/732: {Starch; Amylose; Amylopectin; Derivatives thereof}
- A61K 9/2059: {Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin}
- A61K 31/122: having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
- A61K 31/202: having three or more double bonds, e.g. linolenic (eicosanoids, e.g. leukotrienes A61K31/557)
- A61K 31/366: having six-membered rings, e.g. delta-lactones
- A61K 47/6949: {inclusion complexes, e.g. clathrates, cavitates or fullerenes}
- A61P 7/02: Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A61P 33/06: Antimalarials
- A61P 35/00: Antineoplastic agents
- A61Q 5/02: Preparations for cleaning the hair
- A61Q 5/12: Preparations containing hair conditioners
- C08B 31/04: of organic acids {, e.g. alkenyl-succinated starch}
- C08B 31/12: having alkyl or cycloalkyl radicals substituted by heteroatoms, {e.g. hydroxyalkyl or carboxyalkyl starch}
- C08J 3/12: Powdering or granulating
- C08K 5/0041: {Optical brightening agents, organic pigments}
- C08K 5/01: Hydrocarbons {(C08K5/0091 takes precedence)}
- C08K 5/05: Alcohols; Metal alcoholates
- C08K 5/07: Aldehydes; Ketones
- C08K 5/103: with polyalcohols
- C08K 5/14: Peroxides
- A61K 2800/56: Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms
- C08J 2300/14: Water soluble or water swellable polymers, e.g. aqueous gels
- C08J 2303/04: Starch derivatives
- Y02A 50/30: Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A23D: EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS (preservation thereof A23B20/00; production, refinement or preservation of animal or vegetable fats or oils C11B, C11C)
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- A23P: SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C08B: POLYSACCHARIDES; DERIVATIVES THEREOF (polysaccharides containing less than six saccharide radicals attached to each other by glycosidic linkages C07H; fermentation or enzyme-using processes C12P19/00; sugar industry C13; production of cellulose D21)
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE

## Abstract

The present document describes a powder composition comprising a functionalized starch having a single helix V-structure and having a degree of substitution of at least 0.25, and a bioactive agent, forming an inclusion complex with said functionalized starch, where the bioactive agent is within the helix V-structure of the functionalized starch having a single helix V-structure. Also described are the functionalized starch having a single helix V-structure and having a degree of substitution of at least 0.25, methods of making the same and methods of using the same to manufacture the powder composition.

## Claims

### Claim 1

A powder composition comprising:
a carboxymethylated starch powder prepared by the following process:
(a) placing a native starch and sodium monochloroacetate (SMCA) in an alkaline solvent-water medium having a solvent:water ratio of from about 70% to about 95% (vol/vol) solvent in water and at least 3 M sodium hydroxide (NaOH), and stirring for at least 10 hours at a temperature of from about 22° C. to about 28° C. to generate a carboxymethylated starch; and
(b) washing and drying the carboxymethylated starch from step (a) to generate the carboxymethylated starch powder,
and
a poorly water-soluble or water insoluble bioactive agent, forming a water-soluble or water dispersible inclusion complex with said carboxymethylated starch powder,
wherein said carboxymethylated starch powder and said bioactive agent are present in a ratio of about 4:1 to about 1:1 w/w.

### Claim 2 (depends on 1)

The powder composition of claim 1, wherein said carboxymethylated starch has a degree of substitution (DS) from about 0.25 to about 1.5.

### Claim 3 (depends on 1)

The powder composition of claim 1, wherein said carboxymethylated starch has a DS from about 0.4 to about 0.7.

### Claim 4 (depends on 1)

The powder composition of claim 1, wherein said native starch is a corn starch, a potato starch, a pea starch, a rice starch, a bean starch, a wheat starch, or combinations thereof.

### Claim 5 (depends on 4)

The powder composition of claim 4, wherein said native starch is a potato starch.

### Claim 6 (depends on 1)

The powder composition of claim 1, wherein said solvent-water medium is an alcohol-water medium.

### Claim 7 (depends on 6)

The powder composition of claim 6, wherein said alcohol-water medium is an ethanol-water medium or isopropanol-water medium.

### Claim 8 (depends on 1)

The powder composition of claim 1, wherein said bioactive agent is a simple fatty acid, a lipid compound, a complex lipid, an antibiotic, a protein, a peptide, a pharmaceutically active ingredient or combinations thereof.

### Claim 9 (depends on 8)

The powder composition of claim 8, wherein said simple fatty acid is alpha-linolenic acid, eicosapentaenoic acid, docosahexaenoic acid, or combinations thereof.

### Claim 10 (depends on 8)

The powder composition of claim 8, wherein said complex lipid is a glyceride, a carotenoid, a terpenoid, an isoprenoid, a with anolide, a cholesterol, a phytosterol, a liposoluble vitamin, a stilbenoid, or combinations thereof.

### Claim 11 (depends on 10)

The powder composition of claim 10, wherein said glyceride is omega-3 monoglyceride, omega-3 diglyceride, omega-3 triglycerides, or combinations thereof.

### Claim 12 (depends on 1)

A pharmaceutical composition comprising:
the powder composition of claim 1, and
a pharmaceutically acceptable carrier.

### Claim 13 (depends on 12)

The pharmaceutical composition of claim 12, wherein said bioactive agent is artemisinin or its derivatives.

### Claim 14 (depends on 1)

A method of treating malaria comprising administering to a subject in need thereof the powder composition of claim 1, wherein said bioactive agent is artemisinin.