Thiochromene Mass Tag for MALDI-TOF Solubility
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Solution Overview
Problem
Conventional photocleavable mass tags, such as ferrocene-based derivatives, have low water solubility, leading to low conjugation yields with biomaterials like proteins and nucleic acids, and can deform the three-dimensional structure of biomaterials, reducing their specificity in mass spectrometry analysis.
Innovation Solution
A 2-alkylthio-2H-thiochromene derivative is used as a photocleavable mass tag, which is highly soluble in water, absorbs at 355 nm, and can form stable cations upon laser irradiation, allowing for efficient ionization in both MALDI-TOF and matrix-less LDI-TOF mass spectrometry without the need for a matrix, thereby enhancing sensitivity and specificity.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If ferrocene-based photocleavable mass tags are used, then photocleavage efficiency is improved, but water solubility deteriorates
Solution Approach 1:
The patent combines ferrocene photocleavable group with trityl cation-forming group to create a composite mass tag structure. This composite approach allows the ferrocene moiety to provide high photocleavage efficiency while the trityl moiety contributes to cation stability and solubility characteristics, resolving the contradiction between photocleavage efficiency and water solubility
Solution Approach 2:
The patent modifies the chemical structure parameters of conventional ferrocene derivatives by introducing specific substituents and linkers that enhance water solubility while preserving the photocleavage functionality. This structural parameter optimization allows maintenance of high photocleavage efficiency alongside improved aqueous solubility
2Ease of manufacture
If ferrocene-based mass tags are used, then synthesis ease is improved, but conjugation yield with biomaterials deteriorates
Solution Approach 1:
The patent introduces a linker moiety as an intermediary between the ferrocene photocleavable group and the trityl cation-forming group. This linker serves as a bridge that facilitates efficient conjugation with biomaterials containing functional groups like amines, carboxyls, or hydroxyls, thereby improving conjugation yield while maintaining the ease of synthesis associated with ferrocene chemistry
Solution Approach 2:
The patent assigns different functional qualities to different parts of the mass tag molecule: the ferrocene portion provides photocleavage functionality, the linker provides conjugation functionality, and the trityl portion provides cation formation. This local functional differentiation optimizes each aspect independently, achieving high conjugation yield while preserving synthesis ease
3Use of energy by moving object
If matrix is used for MALDI-TOF mass spectrometry, then ionization efficiency is improved, but measurement accuracy deteriorates
Solution Approach 1:
The patent extracts and eliminates the matrix component from the mass spectrometry system by designing a mass tag that performs its own ionization function. The photocleavable mass tag generates ions directly through laser irradiation without requiring external matrix assistance, thereby removing the source of measurement inaccuracy while maintaining ionization efficiency
Solution Approach 2:
The patent enables the mass tag to perform self-ionization through its intrinsic photocleavable ferrocene group that absorbs laser energy and generates ions autonomously. This self-service ionization capability eliminates dependence on external matrix materials, resolving the contradiction between ionization efficiency and measurement accuracy
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 2-alkylthio-2H-thiochromene derivative achieves high sensitivity and specificity in mass spectrometry by forming stable cations under laser irradiation, improving solubility and conjugation yields with biomaterials, and providing enhanced detection capabilities compared to traditional tags.
Implementation Method 1
a photocleavable mass tag, which may be easily photocleaved by a predetermined laser wavelength to thus release a specific mass-tagged cation
Implementation Method 2
absorbs at 355 nm, and can form stable cations upon laser irradiation
Implementation Method 3
a compound for efficiently forming ions through light irradiation as a mass tag for mass spectrometry
Data Source
AI summary
This invention relates to a photocleavable mass tag and the use thereof, and particularly to a thiochromene-type compound useful for MALDI-TOF (Matrix-Assisted Laser Desorption/Ionization Time-Of-Flight) mass spectrometry or matrix-less LDI-TOF (Laser Desorption/Ionization Time-Of-Flight) mass spectrometry and the use thereof.