Biosensor Phenyl Ester Stability
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Solution Overview
Problem
Conventional biosensors face challenges in maintaining the stability of functional groups used for binding physiologically active substances, as the active esters formed by mixing EDC and NHS in water are not sufficiently stable and undergo hydrolysis over time.
Innovation Solution
A biosensor with a substrate modified by a phenyl ester group having an increased electron-withdrawing ability is used, which is activated through a chemical reaction immediately before forming an amide bond with a compound having an amino group, thereby enhancing both stability and reactivity.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If EDC and NHS are mixed in water to form active ester, then the functional group for binding physiologically active substance is activated, but the active ester is not sufficiently stable and undergoes hydrolysis over time
Solution Approach 1:
The patent changes the chemical structure of the ester group by introducing electron-withdrawing substituents (such as trifluoromethyl groups) at specific positions on the aromatic ring. This structural modification increases the electron-withdrawing ability, which stabilizes the active ester against hydrolysis while maintaining its reactivity toward amino groups. The parameter change is in the chemical composition and electronic properties of the ester group.
2Reliability
If a phenyl ester group with increased electron-withdrawing ability is used, then the stability is improved, but the complexity of the chemical structure increases
Solution Approach 1:
The patent introduces electron-withdrawing substituents at specific local positions (meta and/or para positions) on the aromatic ring of the phenyl ester group, rather than modifying the entire molecule. This localized modification achieves the desired stability enhancement while keeping the rest of the molecular structure relatively simple and manageable.
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 allows for the effective immobilization of physiologically active substances on the biosensor surface, maintaining stability and enabling efficient binding with test substances, as demonstrated by increased fluorescence intensity in binding experiments.
Implementation Method 1
a phenyl ester group having an increased electron-withdrawing ability is used, which is activated through a chemical reaction immediately before forming an amide bond with a compound having an amino group
Implementation Method 2
the carboxylic acid existing on the biosensor surface is activated with 1-(3-dimethylaminopropyl)-3 ethylcarbodiimide (EDC) and N-hydroxysuccinimide (NHS) in an aqueous medium, and the biosensor surface is then allowed to react with the amino group of the physiologically active substance, so as to form a carboxylic amide
Implementation Method 3
The SPR measurement technique is a method of measuring changes in the refractive index near an organic functional film attached to the metal film of a chip by measuring a peak shift in the wavelength of reflected light
Implementation Method 4
The QCM measurement technique is a technique of detecting adsorbed or desorbed mass at the ng level, using a change in frequency of a crystal due to adsorption or desorption of a substance on gold electrodes of a quartz crystal
Implementation Method 5
detecting a substance associated with a living organism from sedimentation of gold fine particles
Data Source
AI summary
It is an object of the present invention to provide a technique of conserving a functional group used for binding a physiologically active substance in the form of an inactive ester, and converting it to an activated ester by simple operations immediately before formation of an amide bond. The present invention provides a biosensor which comprises a substrate that has been modified with a phenyl ester group having a substituent whose electron-withdrawing ability is increased as a result of a chemical reaction.