# US 8,569,005 B2 · Chloroacetamidine based inhibitors and activity based probes for the protein arginine methytransferases

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- Number: US 8,569,005 B2
- Document ID: US8569005B2
- Status: Granted
- Kind: B2
- Application number: 13/670,953
- Filed: 2012-11-07
- Published: 2013-04-11
- Granted: 2013-10-29
- Earliest claimed: 2008-12-12
- Assignees: University of South Carolina
- Applicants: University of South Carolina
- Inventors: Paul R. Thompson; Tanesha C. Osborne; Obiamaka Obianyo; Corey P. Causey
- Web page: https://patentgrep.com/patent/US8569005B2

## CPC

- C07K 14/00: Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K 31/00: Medicinal preparations containing organic active ingredients
- C07K 14/47: from mammals
- C12N 9/1007: {Methyltransferases (general) (2.1.1.)}
- C12Q 1/48: involving transferase
- G01N 2500/00: Screening for compounds of potential therapeutic value
- 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)
- 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)
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)
- C12Q: MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS (immunoassay G01N33/53); COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)

## Abstract

In accordance with certain embodiments of the present disclosure, a protein arginine methyltransferase inhibitor is provided. The inhibitor comprises an amino acid peptide joined to a chloroacetamidine warhead.

## Claims

### Claim 1

A method of identifying a protein arginine methyltransferase inhibitor comprising incubating protein arginine methyltransferase with one or more activity-based protein profiling reagents, at least one reagent comprising peptide joined to a chloroacetamidine warhead, wherein the peptide comprises the first 21 amino acids of histone H4, the reagent further comprising a fluorescent molecule.

### Claim 2 (depends on 1)

The method of claim 1, wherein the fluorescent molecule comprises fluorophore, namely, fluoresceinoisothiocyanate, or biotin, or combinations thereof.

### Claim 3 (depends on 1)

The method of claim 1, wherein more than one reagent comprises peptide joined to a chloroacetamidine warhead and a fluorescent molecule.

### Claim 4

A method of inhibiting protein arginine methyltransferase comprising exposing protein arginine methyltransferase to an inhibitor comprising an amino acid peptide joined to a chloroacetamidine warhead, wherein the peptide comprises the first 21 amino acids of histone H4.