Biodegradable Quinolone Antibiotics with Amide Bonds

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Solution Overview

Problem

The persistence and accumulation of non-degradable antibiotics in water resources pose a risk to water quality and promote antibiotic resistance in bacteria, as existing antibiotics are not effectively biodegradable and can retain antibiotic activity for extended periods, leading to environmental contamination and resistance development.

Innovation Solution

Development of environmentally friendly fluoroquinolone antibiotic variants with amide bonds on the basic structure, which are biodegradable and break down quickly under UV light, maintaining antibiotic activity for a sufficient period in the body but degrading rapidly, reducing the risk of resistance development and environmental contamination.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If non-biodegradable antibiotics are used to treat infections, then antibiotic effectiveness is maintained, but accumulation in water resources occurs and promotes resistance development

Engineering Contradiction:
Improveantibiotic effectivenessVSAvoidenvironmental contamination and resistance promotion
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent modifies the chemical structure of fluoroquinolone antibiotics by introducing amide bonds at specific positions (R3) in the molecule. This structural parameter change enables biodegradability while maintaining antibiotic activity, allowing the substance to break down in the environment after exerting its therapeutic effect, thus eliminating long-term accumulation and resistance promotion.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates antibiotics designed to be temporarily active and then readily degraded. The amide bond-containing structure allows the antibiotic to fulfill its therapeutic function and then be quickly broken down by environmental microorganisms, similar to disposable items that serve their purpose and are then discarded/degraded, preventing persistent environmental contamination.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

2Duration of action of stationary object

If biodegradable compounds with amide bonds are introduced, then environmental persistence is reduced, but stability in the human body must be sufficient for effective treatment duration

Engineering Contradiction:
Improveenvironmental degradation timeVSAvoidantibiotic stability in body
Core Design Contradiction:
Duration of action of stationary objectVSReliability

Solution Approach 1:

The patent applies amide bonds specifically at the R3 position in the fluoroquinolone structure, while maintaining the stability of other critical structural elements. This localized modification enables biodegradability at the environmental level without compromising the overall molecular stability required for effective antibiotic action within the human body during the treatment period.

Inventive Principle:
Principle #3Local quality

3Object-generated harmful factors

If amide bonds are added to the antibiotic backbone, then biodegradability is enhanced, but the risk of enzymatic cleavage in the human body increases

Engineering Contradiction:
Improveenvironmental biodegradabilityVSAvoidmetabolic stability
Core Design Contradiction:
Object-generated harmful factorsVSReliability

Solution Approach 1:

The patent uses proline, a natural amino acid, as the R3 substituent which contains an amide bond. This approach copies a biologically compatible structure that is already present in the human body, reducing the likelihood of unexpected enzymatic cleavage while still providing the desired environmental biodegradability through the same amide bond functionality.

Inventive Principle:
Principle #26Copying

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 new antibiotic variants exhibit significant activity against E. coli while minimizing resistance development in other bacteria and environmental persistence, offering a pharmacologically and environmentally improved treatment option with reduced collateral selection pressure.

Implementation Method 1

after excretion from the body, the compounds are degraded relatively quickly (i.e., within a few weeks or months), for example, under the influence of UV light

Methodology Applied
Scientific EffectPhotodegradation: Photodissociation

Data Source

PatentEP3694516B1Biodegradable quinolone antibiotics
Publication Date: 2023.12.13 LEUPHANA UNIV LUNEBURG STIFTUNG OFFENTLICHEN RECHTS
  • EP3694516B1 patent drawingFigure 1a~1b
  • EP3694516B1 patent drawingFigure 2
  • EP3694516B1 patent drawingFigure 3

AI summary

The present invention relates to novel quinolone antibiotics and to the use thereof.