Sulfodichlorophenol Labeling Reagents for Hydrolytic Stability
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Solution Overview
Problem
Current labeling reagents, such as succinimidyl esters and perfluorophenyl esters, have high reactivity rates with water, leading to hydrolysis and reduced shelf life, resulting in low efficiency and waste in biomolecule labeling processes, especially in aqueous environments.
Innovation Solution
Development of a compound with a sulfodichlorophenol reactive ester that forms a stable conjugate with a reporter molecule and a carrier molecule or solid support, offering enhanced hydrolytic stability and reactivity in aqueous solutions, allowing for efficient biomolecule labeling.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If standard esters (succinimidyl esters or perfluorophenyl esters) are used for labeling, then reactivity with water is high, but hydrolytic stability is poor leading to reduced shelf life and waste
Solution Approach 1:
The patent modifies the chemical structure of the ester by introducing a sulfonate group and changing the phenolic ester to a sulfodichlorophenolic ester. This parameter change in molecular structure dramatically improves hydrolytic stability while maintaining or enhancing reactivity with nucleophiles in biomolecules, resolving the contradiction between stability and reactivity
Solution Approach 2:
The invention creates a composite reactive group combining sulfonate, dichlorophenolic ester, and water-solubilizing moieties into a single molecular structure. This composite approach allows the reagent to simultaneously achieve hydrolytic stability, water solubility, and high reactivity with biomolecules, eliminating the trade-off between stability and functionality
2Productivity
If highly reactive esters are used, then labeling speed is fast, but shelf life is reduced due to premature hydrolysis
Solution Approach 1:
By changing the chemical parameters of the ester (introducing sulfonate and dichlorophenolic groups), the patent achieves a reagent that maintains high labeling efficiency through enhanced nucleophile reactivity while simultaneously extending shelf life through improved resistance to water-mediated hydrolysis
Solution Approach 2:
The patent eliminates the need to treat labeling reagents as short-lived consumables by creating a reagent with extended stability. The improved hydrolytic resistance allows the reagent to be stored and handled without special precautions, reducing waste and improving cost-effectiveness
3Ease of operation
If conventional esters are used in aqueous buffers, then labeling can proceed, but most reagents hydrolyze prior to reaction reducing efficiency
Solution Approach 1:
The patent introduces water-solubilizing groups (sulfonate and dichlorophenolic moieties) that enable the reagent to function effectively in aqueous buffers. Simultaneously, these structural changes provide protection against hydrolysis, ensuring high labeling yields are achieved without significant reagent degradation in aqueous environments
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 compound provides significantly improved stability and labeling efficiency, with nearly twice the biomolecule labeling capacity of equivalent amounts of standard esters, and maintains reactivity across a wide pH range, reducing waste and improving handling and storage.
Implementation Method 1
contacting a carrier molecule or solid support comprising a nucleophile with a compound of Formula IA or a tautomer or salt thereof forming a compound of Formula I or a tautomer or salt thereof
Implementation Method 2
R3 comprises a water solubilizing group
Data Source
AI summary
The present disclosure is directed to a reactive ester agent capable of conjugating a reporter molecule to a carrier molecule or solid support. The reactive ester agent has the general formula:wherein the variables are described throughout the application.