# US 8,784,777 B2 · Flexibly labeling peptides

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 8,784,777 B2
- Document ID: US8784777B2
- Status: Granted
- Kind: B2
- Application number: 12/955,575
- Filed: 2010-11-29
- Published: 2011-05-05
- Granted: 2014-07-22
- Earliest claimed: 2006-09-06
- Assignees: Case Western Reserve University
- Applicants: Mark D. Pagel; Byunghee Yoo
- Inventors: Mark D. Pagel; Byunghee Yoo
- Web page: https://patentgrep.com/patent/US8784777B2

## CPC

- A61K 49/0002: {General or multifunctional contrast agents, e.g. chelated agents}
- A61K 49/085: {conjugated systems}
- A61K 49/14: Peptides, e.g. proteins
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07K 1/04: on carriers {(C07K1/003, C07K1/006 take precedence)}
- C07K 5/06052: {Val-amino acid}
- C07K 5/081: {the side chain containing O or S as heteroatoms, e.g. Cys, Ser}
- C07K 5/0819: {with the first amino acid being acidic}
- C07K 5/1008: {the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala}
- C07K 5/1021: {with the first amino acid being acidic}
- 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 14/47: from mammals
- 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

A solid phase peptide synthesis method for synthesizing a peptidyl contrast agent is disclosed. In one example, the method includes synthesizing an amino-chelator loaded resin, coupling of the amino-chelator loaded resin to the C-terminus and/or backbone of a peptide, cleaving the amino-chelator-peptide from a resin, and chelating a lanthanide metal to the amino-chelator-peptide.

## Claims

### Claim 1

A peptidyl imaging agent, comprising:
a peptide, and
a nitrogen-containing macrocyclic ring containing chelate coupled to an amidated C-terminus of the peptide,
wherein the amide of the peptide is coupled within one carbon atom of the nitrogen in the macrocyclic ring containing of the chelate.

### Claim 2 (depends on 1)

The peptidyl imaging agent of claim 1, including an amide group located from about 4.0 angstroms to about 5.1 angstroms from a lanthanide ion.

### Claim 3 (depends on 1)

The peptidyl imaging agent of claim 1, where the chelate is DOTA-Tm3+.

### Claim 4 (depends on 1)

The peptidyl imaging agent of claim 1, where the chelate is DOTA-Gd3+.

### Claim 5

A peptidyl imaging agent, comprising:
a peptide; and
a nitrogen-containing macrocyclic ring chelate coupled within the backbone of the peptide,
wherein an amide of the backbone of the peptide is coupled within one carbon atom of the nitrogen in the macrocyclic ring chelate.

### Claim 6 (depends on 5)

The peptidyl imaging agent of claim 5, including an amide group located from about 4.0 angstroms to about 5.1 angstroms to a lanthanide ion.

### Claim 7 (depends on 5)

The peptidyl imaging agent of claim 5, where the chelate is DOTA-Tm3+.

### Claim 8 (depends on 5)

The peptidyl imaging agent of claim 5, where the chelate is DOTA-Gd3+.