# US 11,993,556 B1 · Peptoid-based inhibitors of the protein arginine methyltransferase (PRMT) family

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- Number: US 11,993,556 B1
- Document ID: US11993556B1
- Status: Granted
- Kind: B1
- Application number: 17/527,475
- Filed: 2021-11-16
- Granted: 2024-05-28
- Earliest claimed: 2020-11-17
- Assignees: University of North Florida Board of Trustees
- Applicants: Bryan Knuckley; Corey P. Causey; Fatima Khwaja Rehman
- Inventors: Bryan Knuckley; Corey P. Causey; Fatima Khwaja Rehman
- Web page: https://patentgrep.com/patent/US11993556B1

## CPC

- A61K 38/005: {Enzyme inhibitors (protease inhibitors A61K38/55)}
- C07C 259/06: having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
- A61P 35/00: Antineoplastic agents
- 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)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Novel peptoid compounds, compositions and methods of using the compounds and compositions to inhibit protein arginine methyltransferase (PRMT) and induce apoptosis in cancer cells are presented.

## Claims

### Claim 1

A method of inducing apoptosis in at least one cancer cell comprising:
administering a therapeutically effective amount of a peptide mimetic to the at least one cancer cell wherein the peptide mimetic is a peptoid-based inhibitor of protein arginine methyltransferase (PRMT) comprising Formula (II)
wherein R1 is at least one amine monomer;
wherein R2 is at least one amine monomer;
wherein X is a halogen; and
wherein n is an integer between 1 and 4.

### Claim 2 (depends on 1)

The method of claim 1, wherein X is selected from the group consisting of chlorine (Cl), iodine (I), flourine (F), bromine (Br), and astatine (At).

### Claim 3 (depends on 2)

The method of claim 2, wherein the halogen is chlorine (Cl).

### Claim 4 (depends on 3)

The method of claim 3, wherein the peptoid-based inhibitor is unacetylated.

### Claim 5

A method of inhibiting protein arginine methyltransferase (PRMT) in a patient in need thereof comprising:
administering a therapeutically effective amount of a peptide mimetic to the patient wherein the peptide mimetic is a peptoid-based inhibitor of PRMT comprising Formula (I)
wherein R1 is at least one amine monomer;
wherein R2 is at least one amine monomer;
wherein R3 is NH2 or CH2—X;
wherein X is a halogen; and
wherein n is an integer between 1 and 4.

### Claim 6 (depends on 5)

The method of claim 5, wherein R3 is CH2—X.

### Claim 7 (depends on 6)

The method of claim 6, wherein X is selected from the group consisting of chlorine (Cl), iodine (I), flourine (F), bromine (Br), and astatine (At).

### Claim 8 (depends on 5)

The method of claim 5, wherein the peptoid-based inhibitor mimics an N-terminal tail of histone H4.

### Claim 9 (depends on 8)

The method of claim 8, wherein the peptoid-based inhibitor mimics Histone H4-16, Histone-H4-13, or Histone H4-8 peptide.

### Claim 10 (depends on 9)

The method of claim 9, wherein the peptoid-based inhibitor mimics Histone H4-16.

### Claim 11 (depends on 5)

The method of claim 5, wherein the peptoid-based inhibitor is unacetylated.