Options of the Main Derivatization Approaches for Analytical ESI and MALDI Mass Spectrometry

Заикин, В. Г.; Борисов, Р. С.

doi:10.1080/10408347.2021.1873100

Cited by 31 publications

(28 citation statements)

References 406 publications

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“…Planar chromatography is one of the first analytical methods where derivatization procedures were applied mainly for spot visualization (Zarzycki, 2015). Derivatization is also widely used in MALDI-MS and MALDI imaging for enhancing desorption/ ionization efficiencies of the analytes (Zaikin and Halket, 2009;Zaikin and Borisov, 2021). However, chemical modification procedures are much less popular in case of TLC/MALDI.…”

Section: Derivatizationmentioning

confidence: 99%

Recent Advances in Combinations of TLC With MALDI and Other Desorption/Ionization Mass-Spectrometry Techniques

2021

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The combination of planar chromatography with desorption/ionization mass-spectrometry (MS) techniques provides chemists with unique tools for fast and simple separation of mixtures followed by the detection of analytes by the most powerful analytical method. Since its introduction in the early 1990s, thin-layer chromatography (TLC)/matrix-assisted mass spectrometry (MALDI) has been used for the analysis of a wide range of analytes, including natural and synthetic organic compounds. Nowadays, new desorption/ionization approaches have been developed and applied in conjunction with planar chromatography competing with MALDI. This review covers recent developments in the combination of TLC with various desorption/ionization MS methods which were made in recent several years.

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Section: Derivatizationmentioning

confidence: 99%

Recent Advances in Combinations of TLC With MALDI and Other Desorption/Ionization Mass-Spectrometry Techniques

2021

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“…On-tissue chemical derivatization is a well-established strategy for increasing the selectivity and sensitivity of mass spectrometry imaging toward low abundance, poor-ionizing nonpolar and low polarity compounds. − The (1-(4-(aminomethyl)phenyl)pyridin-1-ium chloride (AMPP) derivatization reagent has shown promise for efficient derivatization via amide linkage and sensitive detection of carboxyl-containing biomolecules using LC–MS and MALDI-MS in positive ionization mode. Given the presence of a nucleophilic primary amine, we reasoned that AMPP should undergo Schiff base reactions with aldehyde-containing biomolecules under these conditions.…”

Section: Introductionmentioning

confidence: 99%

On-Tissue Chemical Derivatization for Comprehensive Mapping of Brain Carboxyl and Aldehyde Metabolites by MALDI–MS Imaging

Kaya

Schembri²,

Nilsson

et al. 2023

J. Am. Soc. Mass Spectrom.

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The visualization of small metabolites by MALDI mass spectrometry imaging in brain tissue sections is challenging due to low detection sensitivity and high background interference. We present an on-tissue chemical derivatization MALDI mass spectrometry imaging approach for the comprehensive mapping of carboxyls and aldehydes in brain tissue sections. In this approach, the AMPP (1-(4-(aminomethyl)phenyl)pyridin-1-ium chloride) derivatization reagent is used for the covalent charge-tagging of molecules containing carboxylic acid (in the presence of peptide coupling reagents) and aldehydes. This includes free fatty acids and the associated metabolites, fatty aldehydes, dipeptides, neurotoxic reactive aldehydes, amino acids, neurotransmitters and associated metabolites, as well as tricarboxylic acid cycle metabolites. We performed sensitive ultrahigh mass resolution MALDI-MS detection and imaging of various carboxyl- and aldehyde-containing endogenous metabolites simultaneously in rodent brain tissue sections. We verified the AMPP-derivatized metabolites by tandem MS for structural elucidation. This approach allowed us to image numerous aldehydes and carboxyls, including certain metabolites which had been undetectable in brain tissue sections. We also demonstrated the application of on-tissue derivatization to carboxyls and aldehydes in coronal brain tissue sections of a nonhuman primate Parkinson’s disease model. Our methodology provides a powerful tool for the sensitive, simultaneous spatial molecular imaging of numerous aldehydes and carboxylic acids during pathological states, including neurodegeneration, in brain tissue.

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“…As a class, steroids are commonly derivatized prior to MS-based analysis to improve ionization efficiency, sensitivity, and limits of detection, increase their stability, change their molecular weight and/or charge state, provide characteristic fragmentation patterns, and improve chromatographic resolution by shifting retention time. − Carbonyl and hydroxyl functional groups, one or both of which are found in nearly all steroids, present ideal derivatization sites. Similar strategies have been applied to more broad metabolomics approaches, targeting carbonyl, carboxyl, and phosphoryl functional groups .…”

Section: Introductionmentioning

confidence: 99%

Improved Ion Mobility Separation and Structural Characterization of Steroids using Derivatization Methods

Velosa

Dunham

Rivera

et al. 2022

J. Am. Soc. Mass Spectrom.

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Steroids are an important class of biomolecules studied for their role in metabolism, development, nutrition, and disease. Although highly sensitive GC- and LC-MS/MS-based methods have been developed for targeted quantitation of known steroid metabolites, emerging techniques including ion mobility (IM) have shown promise in improved analysis and capacity to better identify unknowns in complex biological samples. Herein, we couple LC-IM-MS/MS with structurally selective reactions targeting hydroxyl and carbonyl functional groups to improve IM resolution and structural elucidation. We demonstrate that 1,1-carbonyldiimidazole derivatization of hydroxyl stereoisomer pairs such as testosterone/epitestosterone and androsterone/epiandrosterone results in increased IM resolution with ΔCCS > 15%. Additionally, performing this in parallel with derivatization of the carbonyl group by Girard’s Reagent P resulted in unique products based on relative differences in number of each functional group and C17 alkylation. These changes could be easily deciphered using the combination of retention time, collision cross section, accurate mass, and MS/MS fragmentation pattern. Derivatization by Girard’s Reagent P, which contains a fixed charge quaternary amine, also increased the ionization efficiency and could be explored for its potential benefit to sensitivity. Overall, the combination of these simple and easy derivatization reactions with LC-IM-MS/MS analysis provides a method for improved analysis of known target analytes while also yielding critical structural information that can be used for identification of potential unknowns.

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Options of the Main Derivatization Approaches for Analytical ESI and MALDI Mass Spectrometry

Cited by 31 publications

References 406 publications

Recent Advances in Combinations of TLC With MALDI and Other Desorption/Ionization Mass-Spectrometry Techniques

Recent Advances in Combinations of TLC With MALDI and Other Desorption/Ionization Mass-Spectrometry Techniques

On-Tissue Chemical Derivatization for Comprehensive Mapping of Brain Carboxyl and Aldehyde Metabolites by MALDI–MS Imaging

Improved Ion Mobility Separation and Structural Characterization of Steroids using Derivatization Methods

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