Cyclodextrin Encapsulation of 3-Halopyruvates for Systemic Delivery

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Solution Overview

Problem

Current systemic administration of selective ATP inhibitors like 3-halopyruvates is hindered by their reactivity with electrophilic molecules and instability in aqueous environments, leading to increased toxicity and limited efficacy due to rapid degradation, which has restricted their use to loco-regional delivery methods.

Innovation Solution

Encapsulating 3-halopyruvates within cyclodextrins stabilizes the compound in vivo, protecting it from nucleophilic entities and providing a steady release, thereby maintaining its alkylating ability and reducing systemic toxicity, allowing for systemic administration.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If 3-halopyruvates are administered systemically, then they can reach tumor cells throughout the body, but they react with nucleophilic groups in proteins and degrade rapidly in aqueous environments, leading to increased toxicity and reduced efficacy

Engineering Contradiction:
Improvesystemic administration capabilityVSAvoidcompound stability
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

The patent uses cyclodextrins as intermediary carriers to encapsulate 3-halopyruvates. The cyclodextrin cavity provides a hydrophobic environment that protects the electrophilic 3-halopyruvate from nucleophilic attack by proteins and aqueous degradation, enabling systemic administration while maintaining compound stability and anticancer activity

Inventive Principle:
Principle #24Intermediary (Mediator)

2Quantity of substance

If the dose of 3-halopyruvates is increased to overcome rapid degradation, then more compound reaches the target, but toxicity near the injection site increases

Engineering Contradiction:
Improveamount of active compound at targetVSAvoidlocal toxicity
Core Design Contradiction:
Quantity of substanceVSObject-affected harmful factors

Solution Approach 1:

The cyclodextrin encapsulation performs preliminary protection of the 3-halopyruvate before administration. This preliminary action prevents premature reaction with nucleophilic groups in the circulation, allowing the compound to reach the target with sufficient concentration without requiring dose increases that would cause local toxicity

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

Cyclodextrins act as intermediaries that control the release and delivery of 3-halopyruvates to the target site, ensuring that the compound remains stable during circulation and only becomes active when needed, thereby reducing local toxicity while maintaining effective target concentration

Inventive Principle:
Principle #24Intermediary (Mediator)

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 cyclodextrin encapsulation of 3-halopyruvates enhances their stability and efficacy, enabling effective systemic delivery while minimizing toxicity, as demonstrated in both in vitro and in vivo models, particularly with β-cyclodextrins providing better protection than α-cyclodextrins.

Implementation Method 1

Encapsulating 3-halopyruvates within cyclodextrins stabilizes the compound in vivo, protecting it from nucleophilic entities

Methodology Applied
Scientific EffectEncapsulation: Physical Containment

Implementation Method 2

providing a steady release, thereby maintaining its alkylating ability and reducing systemic toxicity

Methodology Applied
Scientific EffectSteady release: Diffusion

Data Source

PatentEP3094317B1Cyclodextrin compositions encapsulating a selective ATP inhibitor and uses thereof
Publication Date: 2019.10.02 JOHNS HOPKINS UNIVERSITY
  • EP3094317B1 patent drawingFigure 1
  • EP3094317B1 patent drawingFigure 2A~2B
  • EP3094317B1 patent drawingFigure 3

AI summary

The invention provides compositions comprising cyclodextrins encapsulating a selective ATP inhibitor, as well as uses thereof.