# US 10,245,327 B2 · Cell penetrating peptide, conjugate comprising same, and composition comprising conjugate

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- Number: US 10,245,327 B2
- Document ID: US10245327B2
- Status: Granted
- Kind: B2
- Application number: 15/374,805
- Filed: 2016-12-09
- Published: 2017-04-27
- Granted: 2019-04-02
- Earliest claimed: 2012-09-19
- Assignees: GemVax & KAEL Co., Ltd.
- Applicants: GemVax & KAEL Co., Ltd.
- Inventors: Sang Jae Kim
- Web page: https://patentgrep.com/patent/US10245327B2

## CPC

- A61K 49/0056: {Peptides, proteins, polyamino acids}
- A23L 33/175: Amino acids
- A23L 33/18: Peptides; Protein hydrolysates
- A61K 9/0019: {Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner (non-active ingredients are additionally classified in A61K47/00)}
- A61K 47/64: Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent (peptidic linkers A61K47/65)
- A61K 49/0043: {Fluorescein, used in vivo}
- A61P 35/00: Antineoplastic agents
- A61P 35/02: specific for leukemia
- A61P 37/02: Immunomodulators
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07K 7/08: having 12 to 20 amino acids (gastrins C07K14/595; somatostatins C07K14/655; melanotropins C07K14/68)
- C07K 14/00: Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A23V 2002/00: Food compositions, function of food ingredients or processes for food or foodstuffs
- A61K 38/00: Medicinal preparations containing peptides (peptides containing beta-lactam rings A61K31/00; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, A61K31/00; ergot alkaloids of the cyclic peptide type A61K31/48; containing macromolecular compounds having statistically distributed amino acid units A61K31/74; medicinal preparations containing antigens or antibodies A61K39/00; medicinal preparations characterised by the non-active ingredients, e.g. peptides as drug carriers, A61K47/00)
- 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)
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00)
- A23V: INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION

## Abstract

The present invention relates to a conjugate of cell penetrating peptide and an active ingredient; and its use. Specifically, a conjugate including a cell penetrating peptide which is a peptide comprising any one amino acid sequence of SEQ ID NO: 2 to SEQ ID NO: 178, a fragment of any one sequence of SEQ ID NO: 2 to SEQ ID NO: 178, or a peptide having above 80% homology with the above-mentioned sequence; and a composition comprising the same are disclosed.

## Claims

### Claim 1

A conjugate having cell penetrating activity, wherein the conjugate comprises a cell penetrating carrier peptide and an active ingredient, the carrier peptide is 11 amino acids in length and consists of the amino acid sequence of SEQ ID NO:139, and wherein the carrier peptide increases the cell penetration of the active ingredient.

### Claim 2 (depends on 1)

The conjugate according to claim 1, wherein the active ingredient is a protein, nucleic acid, peptide, lipid, mineral, sugar, nano-particle, contrast agent, or drug.

### Claim 3 (depends on 2)

The conjugate according to claim 2, wherein the active ingredient is a protein or a peptide.

### Claim 4 (depends on 3)

The conjugate according to claim 3, wherein the active ingredient is a cytokine, antibody, fragment of antibody, therapeutic enzyme, soluble receptor or ligand.

### Claim 5 (depends on 2)

The conjugate according to claim 2, wherein the contrast agent is selected from the group consisting of radiopaque contrast agent, paramagnetic contrast agent, superparamagnetic contrast agent and computed tomography (CTS contrast agent.

### Claim 6 (depends on 2)

The conjugate according to claim 2, wherein the contrast agent comprises iron.

### Claim 7 (depends on 6)

The conjugate according to claim 6, wherein the contrast agent is a ferrocene carboxylate.

### Claim 8 (depends on 1)

The conjugate according to claim 1, wherein the carrier peptide is bonded to the active ingredient via a covalent bond and optionally mediated by a linker.

### Claim 9 (depends on 1)

The conjugate according to claim 1, wherein the carrier peptide is bonded to the active ingredient via a non-covalent bond.

### Claim 10 (depends on 1)

A contrast agent comprising the conjugate of claim 1.

### Claim 11 (depends on 10)

A cell comprising the contrast agent according to claim 10.

### Claim 12 (depends on 11)

The cell according to claim 11, wherein the host cell is a stem cell.

### Claim 13 (depends on 1)

A composition comprising the conjugate according to claim 1 as an active ingredient wherein the composition is selected from a pharmaceutical composition, a cosmetic composition, and a health food composition.

### Claim 14 (depends on 13)

The composition according to claim 13, wherein the composition is a pharmaceutical composition.

### Claim 15 (depends on 13)

The composition according to claim 13, wherein the composition is a cosmetic composition.

### Claim 16 (depends on 13)

The composition according to claim 13, wherein the composition is a health food composition.

### Claim 17

A cell penetrating carrier peptide that is 11 amino acids in length and consists of the amino acid sequence of SEQ ID NO: 139.

### Claim 18

A conjugate having cell penetrating activity, wherein the conjugate comprises a cell penetrating carrier peptide and an active ingredient, the carrier peptide is 12 amino acids in length and consists of the amino acid sequence of SEQ ID NO:130, and wherein the carrier peptide increases the cell penetration of the active ingredient.

### Claim 19 (depends on 18)

The conjugate according to claim 18, wherein the active ingredient is a protein, nucleic acid, peptide, lipid, mineral, sugar, nano-particle, contrast agent, or drug.

### Claim 20 (depends on 19)

The conjugate according to claim 19, wherein the active ingredient is a protein or a peptide.

### Claim 21 (depends on 20)

The conjugate according to claim 20, wherein the active ingredient is a cytokine, antibody, fragment of antibody, therapeutic enzyme, soluble receptor or ligand.

### Claim 22 (depends on 19)

The conjugate according to claim 19, wherein the contrast agent is selected from the group consisting of radiopaque contrast agent, paramagnetic contrast agent, superparamagnetic contrast agent and computed tomography (CT) contrast agent.

### Claim 23 (depends on 19)

The conjugate according to claim 19, wherein the contrast agent comprises iron.

### Claim 24 (depends on 23)

The conjugate according to claim 23, wherein the contrast agent is a ferrocene carboxylate.

### Claim 25 (depends on 18)

The conjugate according to claim 18, wherein the carrier peptide is bonded to the active ingredient via a covalent bond and optionally mediated by a linker.

### Claim 26 (depends on 18)

The conjugate according to claim 18, wherein the carrier peptide is bonded to the active ingredient via a non-covalent bond.

### Claim 27 (depends on 18)

A contrast agent comprising the conjugate of claim 18.

### Claim 28 (depends on 27)

A cell comprising the contrast agent according to claim 27.

### Claim 29 (depends on 28)

The cell according to claim 28, wherein the host cell is a stem cell.

### Claim 30 (depends on 18)

A composition comprising the conjugate according to claim 18 as an active ingredient; wherein the composition is selected from a pharmaceutical composition, a cosmetic composition, and a health food composition.

### Claim 31 (depends on 30)

The composition according to claim 30, wherein the composition is a pharmaceutical composition.

### Claim 32 (depends on 30)

The composition according to claim 30, wherein the composition is a cosmetic composition.

### Claim 33 (depends on 30)

The composition according to claim 30, wherein the composition is a health food composition.

### Claim 34

A cell penetrating carrier peptide that is 12 amino acids in length and consists of the amino acid sequence of SEQ ID NO: 130.