Azide-Functionalized Sequestration Reagent for Alkyne Molecules

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Solution Overview

Problem

The selective sequestration of alkyne-presenting molecules, such as 17α-ethinylestradiol, from environmental water systems is challenging due to their toxic effects and ability to disrupt hormonal homeostasis, despite existing methods, as they can mimic hormones and interfere with biological systems.

Innovation Solution

A method and system using a sequestration reagent with azide or sulfonyl azide groups that binds to alkyne-presenting molecules through click chemistry, allowing for their removal from unprepared matrices, including aqueous and organic media, using copper(I)-catalyzed reactions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional sequestration methods are used to remove alkyne-presenting molecules from water systems, then some removal capability is achieved, but selectivity is insufficient allowing hormone-mimicking chemicals to interfere with biological systems

Engineering Contradiction:

Improveselectivity of sequestrationVSAvoidtoxic effects on biological systems

Core Design Contradiction:

ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The invention changes the chemical parameter of the sequestration reagent by introducing azide or sulfonyl azide functional groups that specifically react with alkyne moieties. This chemical parameter change enables high selectivity for alkyne-presenting molecules among various hormone-mimicking compounds, resolving the contradiction between removal capability and selectivity

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention employs composite materials combining a support structure with azide or sulfonyl azide functional groups. This composite approach creates a sequestration reagent that maintains structural stability while providing specific chemical reactivity toward alkyne-containing compounds, thereby achieving both reliable removal and high selectivity

Inventive Principle:

Principle #40Composite materials

2Measurement precision

If sample preparation steps are implemented to improve detection accuracy of alkyne-presenting molecules, then measurement precision increases, but processing time and operational complexity increase

Engineering Contradiction:

Improvedetection accuracyVSAvoidprocessing time

Core Design Contradiction:

Measurement precisionVSLoss of time

Solution Approach 1:

The sequestration reagent is pre-functionalized with azide or sulfonyl azide groups that are specifically designed to react with alkyne moieties. This preliminary preparation of the reagent with built-in selectivity eliminates the need for time-consuming sample preparation steps, achieving both high detection accuracy and rapid processing

Inventive Principle:

Principle #10Preliminary action

Solution Approach 2:

The azide or sulfonyl azide functional groups act as intermediaries that specifically mediate the interaction between the sequestration reagent and alkyne-presenting molecules. This intermediary mechanism provides inherent selectivity that eliminates the need for complex sample preparation procedures, reducing both time and operational complexity

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

This approach enables the selective and efficient sequestration of 17α-ethinylestradiol from various matrices, including water, blood, and urine, without the need for sample preparation, using Cu(I)-catalyzed 1,3-dipolar cycloaddition reactions, effectively reducing the concentration of these toxic compounds.

Implementation Method 1

binding of the azide or sulfonyl azide groups to the one or more alkyne-presenting molecules results in sequestration of the alkyne-presenting molecules from the matrix

Methodology Applied

Scientific EffectClick chemistry: Chemical Bonding

Implementation Method 2

using copper(I)-catalyzed reactions

Methodology Applied

Scientific EffectCu(I)-catalyzed 1,3-dipolar cycloaddition: Catalysis

Data Source

PatentUS10088491B2Methods for the selective sequestration of alkyne-presenting molecules and related compositions and methods

Publication Date: 2018.10.02 LAWRENCE LIVERMORE NAT SECURITY LLC

AI summary

Provided herein are methods for sequestering an alkyne-presenting molecule in a sample and related sequestration reagents, compositions, methods and systems.