Quaternary Ammonium Compounds with Aromatic Rings for Bacterial Infections

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Solution Overview

Problem

Current antibiotic options are limited by bacterial resistance, and quaternary amine compounds (QACs) used for disinfection are toxic and have unclear antimicrobial effects, particularly at near-inhibitory concentrations, raising concerns about cross-resistance and toxicity, necessitating the development of new compounds for treating bacterial infections.

Innovation Solution

Development of compounds containing one or more quaternary ammonium ions linked by multiple aromatic rings, which may be less toxic and more effective than traditional QACs, potentially usable as pharmaceuticals to treat bacterial infections, including multi-drug resistant strains.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If traditional quaternary ammonium compounds (QACs) are used for disinfection at high concentrations, then antimicrobial effectiveness is improved, but toxicity increases

Engineering Contradiction:
Improveantimicrobial effectivenessVSAvoidtoxicity
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent modifies the chemical structure of traditional QACs by introducing multiple aromatic rings between quaternary ammonium groups, changing the molecular parameters to achieve both reduced toxicity and maintained antimicrobial effectiveness. This structural parameter change allows the compound to be effective at lower concentrations with reduced harmful effects.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite molecular structures combining multiple quaternary ammonium groups separated by aromatic ring systems, forming a new class of compounds that integrate the antimicrobial properties of QACs with the structural stability and reduced toxicity of aromatic frameworks.

Inventive Principle:
Principle #40Composite materials

2Reliability

If traditional QACs are used as biocides, then antimicrobial activity is achieved, but cross-resistance with antibiotics may develop

Engineering Contradiction:
Improveantimicrobial activityVSAvoidcross-resistance risk
Core Design Contradiction:
ReliabilityVSPower

Solution Approach 1:

By changing the molecular parameters of QACs through the introduction of multiple aromatic rings, the patent creates compounds with novel mechanisms of action that differ from traditional QACs and antibiotics, thereby reducing the risk of cross-resistance while maintaining antimicrobial activity.

Inventive Principle:
Principle #35Parameter changes

3Object-affected harmful factors

If QACs are used at near inhibitory concentrations, then reduced toxicity may be achieved, but antimicrobial effectiveness becomes unclear

Engineering Contradiction:
ImprovetoxicityVSAvoidantimicrobial effectiveness
Core Design Contradiction:
Object-affected harmful factorsVSReliability

Solution Approach 1:

The structural modifications with multiple aromatic rings enhance the antimicrobial potency of the compounds, allowing them to maintain effectiveness at lower concentrations where traditional QACs would be ineffective, thus resolving the uncertainty about antimicrobial activity at near-inhibitory doses.

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentUS20240116857A1Quaternary ammonium compounds as antimicrobials
Publication Date: 2024.04.11 SAINT LOUIS UNIV
  • US20240116857A1 patent drawing
  • US20240116857A1 patent drawing
  • US20240116857A1 patent drawing

AI summary

In one aspect, the present disclosure provides compounds such as those with one or more quaternary ammonium ions joined by one or more aromatic rings. These compounds may have a formula:These compounds may be used in the treatment of a microbial infection such as a bacterial infection including infections of drug resistant strains of bacteria.