# US 11,077,199 B2 · Albumin binding peptide conjugates and methods thereof

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- Number: US 11,077,199 B2
- Document ID: US11077199B2
- Status: Granted
- Kind: B2
- Application number: 16/059,523
- Filed: 2018-08-09
- Published: 2019-02-14
- Granted: 2021-08-03
- Earliest claimed: 2017-08-09
- Assignees: Massachusetts Institute of Technology
- Applicants: Massachusetts Institute of Technology
- Inventors: Kelly Dare Moynihan; Rebecca Lynn Holden; Darrell J. Irvine; Bradley Lether Pentelute
- Web page: https://patentgrep.com/patent/US11077199B2

## CPC

- A61K 47/646: {the entire peptide or protein drug conjugate elicits an immune response, e.g. conjugate vaccines}
- A61K 39/0011: {Cancer antigens}
- A61K 39/001192: {Glycoprotein 100 [Gp100]}
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P 35/00: Antineoplastic agents
- C07K 7/06: having 5 to 11 amino acids
- C07K 7/08: having 12 to 20 amino acids (gastrins C07K14/595; somatostatins C07K14/655; melanotropins C07K14/68)
- C07K 14/4748: {Tumour specific antigens; Tumour rejection antigen precursors [TRAP], e.g. MAGE}
- C07K 14/76: Albumins
- 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 2039/55561: {CpG containing adjuvants; Oligonucleotide containing adjuvants}
- A61K 2039/6031: {Proteins}
- A61K 2039/6093: {Synthetic polymers, e.g. polyethyleneglycol [PEG], Polymers or copolymers of (D) glutamate and (D) lysine}
- A61K 2039/876: {Skin, melanoma}
- C07K 2319/00: Fusion polypeptide
- 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)
- 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)

## Abstract

The present invention provides a conjugate comprising an albumin binding peptide and a cargo, compositions for directing cargos to the lymphatic system, and vaccines. The methods of the invention can be used to increase an immune response, or to treat cancer or an infectious disease.

## Claims

### Claim 1

A conjugate for priming an endogenous immune response comprising:
(a) an albumin binding peptide; and
(b) an immunomodulatory molecule, wherein the immunomodulatory molecule is a peptide antigen or an immunostimulatory oligonucleotide,
and wherein the albumin binding peptide is operatively coupled to the immunomodulatory molecule with or without a linker domain, thereby providing a conjugate for priming an endogenous immune response.

### Claim 2 (depends on 1)

The conjugate of claim 1, wherein the albumin binding peptide is covalently linked to the immunomodulatory molecule, or the albumin binding peptide is operatively coupled to the immunomodulatory molecule via a linker domain.

### Claim 3 (depends on 2)

The conjugate of claim 2, wherein the linker domain comprises a Gly-Ser linker or a polyethylene glycol (PEG) linker.

### Claim 4 (depends on 3)

The conjugate of claim 3, wherein the Gly-Ser linker is a (Gly4Ser)n (SEQ ID NO: 44) linker, and wherein n is 1-6.

### Claim 5 (depends on 3)

The conjugate of claim 3, wherein the PEG linker is a PEG2000 linker.

### Claim 6 (depends on 1)

The conjugate of claim 1, wherein the peptide antigen is a cancer antigen or a melanoma antigen.

### Claim 7 (depends on 1)

The conjugate of claim 1, wherein the immunostimulatory oligonucleotide is CpG DNA.

### Claim 8 (depends on 1)

The conjugate of claim 1, wherein the albumin binding peptide comprises the amino acid sequence DICLPRWGCLW (SEQ ID NO: 9).

### Claim 9 (depends on 1)

A vaccine comprising the conjugate of claim 1 and a pharmaceutically acceptable carrier or excipient.

### Claim 10 (depends on 9)

The vaccine of claim 9 further comprising an adjuvant.

### Claim 11

A composition for directing immunomodulatory molecules to the lymphatic system, wherein the composition comprises a conjugate comprising:
(a) an albumin binding peptide; and
(b) an immunomodulatory molecule,
wherein the immunomodulatory molecule is a peptide antigen or an immunostimulatory oligonucleotide, and wherein the albumin binding peptide is operatively coupled to the immunomodulatory molecule with or without a linker domain.

### Claim 12 (depends on 11)

The composition of claim 11, wherein the conjugate exhibits increased accumulation in the lymph node when administered to the subject in vivo compared to administration of the antigen alone.

### Claim 13 (depends on 1)

An immunogenic composition comprising the conjugate of claim 1.

### Claim 14 (depends on 9)

An immunogenic composition comprising the vaccine of claim 9.

### Claim 15 (depends on 1)

A nucleic acid molecule encoding the conjugate according to claim 1.

### Claim 16 (depends on 15)

A recombinant expression vector comprising a nucleic acid molecule according to claim 15.

### Claim 17 (depends on 16)

A host cell transformed with the recombinant expression vector according to claim 16.

### Claim 18 (depends on 11)

The composition of claim 11, wherein the albumin binding peptide is covalently linked to the immunomodulatory molecule, or the albumin binding peptide is operatively coupled to the immunomodulatory molecule via a linker domain.

### Claim 19 (depends on 18)

The composition of claim 18, wherein the linker domain comprises a Gly-Ser linker or a polyethylene glycol (PEG) linker.

### Claim 20 (depends on 19)

The composition of claim 19, wherein the Gly-Ser linker is a (Gly4Ser)n (SEQ ID NO: 44) linker.

### Claim 21 (depends on 19)

The composition of claim 19, wherein the PEG linker is a PEG2000 linker.

### Claim 22 (depends on 11)

The composition of claim 11, wherein the peptide antigen is a cancer antigen or a melanoma antigen.

### Claim 23 (depends on 11)

The composition of claim 11, wherein the immunostimulatory oligonucleotide is CpG DNA.

### Claim 24 (depends on 11)

The composition of claim 11, wherein the albumin binding peptide comprises the amino acid sequence DICLPRWGCLW (SEQ ID NO: 9).