Click-mass Spectrometry of Alkyne-Labeled Compounds

Simple SummaryContent extracted from patent full text and abstract with AI.

This invention provides specialized nitrogen-containing compounds and methods that greatly improve the detection and quantification of alkyne-labeled organic molecules (such as lipids, proteins, and nucleic acids) using mass spectrometry. By employing unique 'click chemistry' reactions, the invention attaches positively charged tags to alkyne-labeled compounds, which makes them much easier and more sensitive to detect with mass spectrometry. The process is faster, more sensitive, and provides higher resolution than traditional radioactive or fluorescent labeling techniques, while also supporting sample multiplexing and absolute quantification.

Use CasesContent extracted from patent full text and abstract with AI.

• Analyzing and quantifying lipid metabolism in biological cells (including research on metabolic diseases such as diabetes or metabolic syndrome).
• Determining enzyme activity in biological samples (e.g., lipid-processing enzymes).
• High-throughput screening of biochemical reactions involving alkyne-labeled substrates.
• Analyzing metabolic incorporation of alkyne-labeled precursors into biomolecules in vivo or in vitro.
• Direct detection of alkyne-labeled proteins, peptides, nucleic acids, or small molecules in complex biological mixtures.
• Pharmaceutical development and biomarker discovery, especially where sensitive and multiplexed lipidomics or metabolomics are required.
• Clinical research and diagnostics involving measurement of labeled biomolecules in blood, serum, or tissue samples.

BenefitsContent extracted from patent full text and abstract with AI.

• Faster analysis (hours instead of days) compared to traditional labeling methods.
• Greatly increased sensitivity and resolution, enabling detection and quantification of low-abundance molecular species.
• No requirement for radioactive tracers, improving safety and simplifying procedures.
• Ability to distinguish and quantify specific molecular species rather than just classes (e.g., detecting distinct lipid species).
• Supports multiplexing (measuring multiple samples together in one mass spectrometry run), reducing measurement time and improving data comparability.
• Permanent positive charge on tags improves ionization, leading to stronger and more reliable mass spectrometry signals.
• Allows absolute quantification by inclusion of internal standards, improving accuracy and reproducibility.
• Simpler sample preparation procedures, reducing complexity, time, and risk of error.
• Flexibility for use with a wide range of biomolecules, not only lipids but also proteins, nucleic acids, etc.
• Tags can be isotopically labeled for advanced multiplexed experiments and error correction.

Technical Classifications (CPCs)

Inventors & Applicants

Patent Abstract

The present invention relates to specific nitrogen containing compounds of formulas (I), (II) and (IV) of the present invention, which are suitable to be used in a method to detect alkyne group containing organic compounds by mass spectrometry. Furthermore, the present invention relates to methods for the synthesis of these compounds and for the detection of organic compounds containing the specific compounds of the present invention, uses of the compounds in mass spectrometry, for determining enzyme activity or monitoring the lipid metabolism in a cell, and a kit, which contains at least one of these compounds and at least one internal standard.