Pleuromulin Lipoic Acid Ester Antibacterial Activity

Solution Overview

Problem

Current antibacterial drugs are ineffective against multi-drug resistant bacteria, posing a significant challenge in clinical treatment, especially for vulnerable populations such as infants, young children, immunocompromised individuals, and the elderly.

Innovation Solution

The development of a pleuromulin lipoic acid ester, synthesized by reacting pleuromulin with lipoic acid using specific solvents and catalysts, which demonstrates excellent antibacterial activity against multi-drug resistant bacteria.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If commonly used antibacterial drugs (β-lactams, aminoglycosides, fluoroquinolones, macrolides, tetracyclines) are used for treatment, then treatment coverage is broad, but effectiveness against multi-drug resistant bacteria is poor

Engineering Contradiction:

Core Design Contradiction:

ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent creates a composite molecular structure by combining pleuromulin (a diterpenoid antibiotic) with lipoic acid through esterification. This composite molecule integrates the antibacterial properties of pleuromulin with the antioxidant and membrane-disrupting capabilities of lipoic acid, resulting in enhanced effectiveness against multi-drug resistant bacteria while maintaining broad treatment coverage

Inventive Principle:

Principle #40Composite materials

2Reliability

If pleuromulin is modified by lipoic acid to obtain pleuromulin lipoic acid ester, then antibacterial activity is enhanced, but synthesis complexity increases

Engineering Contradiction:

Core Design Contradiction:

ReliabilityVSDevice complexity

Solution Approach 1:

The patent modifies the chemical parameters of pleuromulin by introducing lipoic acid through controlled esterification reactions. By adjusting reaction conditions (catalysts, solvents, temperature, molar ratios), the synthesis process achieves high conversion efficiency and product purity while managing the complexity of creating this novel composite molecule

Inventive Principle:

Principle #35Parameter changes

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The pleuromulin lipoic acid ester exhibits strong inhibitory effects on multi-drug resistant Staphylococcus aureus, offering a promising candidate for treating infections caused by these bacteria with potential low toxicity and high medical application value.

Implementation Method 1

reacting a compound of formula (II) (pleuromulin) with a compound of formula (III) (lipoic acid) to obtain the compound of formula (I)

Methodology Applied

Scientific EffectEsterification: Chemical Bonding

Implementation Method 2

adding an organic solvent, a catalytic amount of 4-DMAP ((4-dimethylamino)pyridine), and DCC (N,N′-Dicyclohexylcarbodiimide)

Methodology Applied

Scientific EffectCatalysis: Catalysis

Data Source

PatentUS11597714B2Pleuromulin lipoic acid ester with antibacterial activity and a method of preparing the same

Publication Date: 2023.03.07

AI summary

A compound with anti-drug resistant bacteria activity having the following formula (I):is disclosed. A method of preparing the compound of formula (I) is also disclosed.