# US 12,109,187 B2 · Antimicrobial compositions and related methods

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- Number: US 12,109,187 B2
- Document ID: US12109187B2
- Status: Granted
- Kind: B2
- Application number: 17/396,223
- Filed: 2021-08-06
- Published: 2022-02-10
- Granted: 2024-10-08
- Earliest claimed: 2020-08-07
- Assignees: West Liberty University; The University of Mississippi
- Applicants: West Liberty University; University of Mississippi
- Inventors: Joseph A. Horzempa; Elliot M. Collins; Juan Francisco Leon
- Web page: https://patentgrep.com/patent/US12109187B2

## CPC

- A61K 31/36: Compounds containing methylenedioxyphenyl groups, e.g. sesamin
- A61K 31/09: having two or more such linkages
- A61P 31/04: Antibacterial agents
- Y02A 50/30: Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
- 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
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE

## Abstract

A pharmaceutical composition is provided that comprises an effective amount of dillapiole or a derivative thereof, and a pharmaceutically-acceptable vehicle, carrier, or excipient. Methods of treating a bacterial infection are also described and include administering an effective amount of dillapiole or a derivative thereof to a subject in need of such treatment. Methods of reducing bacterial virulence are further described and include contacting a bacterium, such as a F. tularensis or A. baumannii bacterium, with an effective amount of dillapiole or a derivative thereof.

## Claims

### Claim 1

A method for treating a bacterial infection, comprising administering to a subject in need thereof an effective amount of dillapiole, wherein the bacterial infection is a F. tularensis or an A. baumannii infection, and wherein the dillapiole or the derivative thereof has the formula:
wherein R1 and R2 are independently selected from a hydrogen atom and an alkyl group; or
wherein R1 is selected from a propene group, a propyne group, a propane group, an isopropyl group, or a cyclopropyl group.

### Claim 2 (depends on 1)

The method of claim 1, wherein administering the dillapiole comprises administering an amount of dillapiole sufficient to reduce an amount of expression of one or more virulence factors in a bacterium, to reduce an amount of activity of MglA/SspA in the bacterium, or to reduce an amount of replication by the bacterium.

### Claim 3 (depends on 2)

The method of claim 2, wherein the replication is intracellular replication.

### Claim 4 (depends on 2)

The method of claim 2, wherein the bacterium is an antibiotic resistant bacterium.

### Claim 5 (depends on 1)

The method of claim 1, wherein administering the dillapiole comprises administering an amount of dillapiole sufficient to reduce an expression level of tumor necrosis factor alpha (TNFα) in the subject.

### Claim 6

A method for reducing bacterial virulence, comprising contacting a bacterium with an effective amount of dillapiole, wherein the bacterium is a bacterium reliant on activity of MglA/SspA for pathogenesis, and wherein contacting the bacterium with the dillapiole comprises contacting the bacterium with an amount of the dillapiole sufficient to reduce an amount of activity of MglA/SspA in the bacterium or to reduce an expression level of one or more genes controlled by MglA/SspA in the bacterium, and wherein the dillapiole has the formula:
wherein R1 and R2 are independently selected from a hydrogen atom and an alkyl group; or
wherein R1 is selected from a propene group, a propyne group, a propane group, an isopropyl group, or a cyclopropyl group.

### Claim 7 (depends on 6)

The method of claim 6, wherein the one or more genes are encoded by the Francisella pathogenicity island (FPI).

### Claim 8 (depends on 6)

The method of claim 6, wherein the bacterium is an antibiotic resistant bacterium.

### Claim 9 (depends on 6)

The method of claim 6, wherein the bacterium is selected from F. tularensis or A. baumannii.

### Claim 10 (depends on 1)

The method of claim 1, wherein administering the effective amount of dillapiole comprises administering dillapiole having the formula:

### Claim 11 (depends on 6)

The method of claim 6, wherein administering the effective amount of dillapiole comprises administering dillapiole having the formula: