Development of versatile isotopic labeling reagents for profiling the amine submetabolome by liquid chromatography–mass spectrometry

Zhou, Ruokun; Huan, Tao; Liang, Li

doi:10.1016/j.aca.2015.04.021

Cited by 19 publications

(13 citation statements)

References 35 publications

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“…In‐source‐generated fragment ions of the [M + H] + ion of tryptophan are detected at m / z 130 (3‐indolylmethyl cation), m / z 159 (immonium ion of tryptophan) and m / z 188 (neutral loss of ammonia), as described by various authors . The two fragment ions at m / z 159 and m / z 188 could be observed in positive ion mode by both LDI and MALDI.…”

Section: Resultsmentioning

confidence: 64%

A laser desorption ionization/matrix‐assisted laser desorption ionization target system applicable for three distinct types of instruments (LinTOF/curved field RTOF, LinTOF/RTOF and QqRTOF) with different performance characteristics from three vendors

Rados

Pittenauer

Frank

et al. 2018

Rapid Comm Mass Spectrometry

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RationaleWe have developed a target system which enables the use of only one target (i.e. target preparation set) for three different laser desorption ionization (LDI)/matrix‐assisted laser desorption ionization (MALDI) mass spectrometric instruments. The focus was on analysing small biomolecules with LDI for future use of the system for the study of meteorite samples (carbonaceous chondrites) using devices with different mass spectrometric performance characteristics.MethodsThree compounds were selected due to their potential presence in meteoritic chondrites: tryptophan, 2‐deoxy‐d‐ribose and triphenylene. They were prepared (with and without MALDI matrix, i.e. MALDI and LDI) and analysed with three different mass spectrometers (LinTOF/curved field RTOF, LinTOF/RTOF and QqRTOF). The ion sources of two of the instruments were run at high vacuum, and one at intermediate pressure. Two devices used a laser wavelength of 355 nm and one a wavelength of 337 nm.ResultsThe developed target system operated smoothly with all devices. Tryptophan, 2‐deoxy‐d‐ribose and triphenylene showed similar desorption/ionization behaviour for all instruments using the LDI mode. Interestingly, protonated tryptophan could be observed only with the LinTOF/curved field RTOF device in LDI and MALDI mode, while sodiated molecules were observed with all three instruments (in both ion modes). Deprotonated tryptophan was almost completely obscured by matrix ions in the MALDI mode whereas LDI yielded abundant deprotonated molecules.ConclusionsThe presented target system allowed successful analyses of the three compounds using instruments from different vendors with only one preparation showing different analyser performance characteristics. The elemental composition with the QqRTOF analyser and the high‐energy 20 keV collision‐induced dissociation fragmentation will be important in identifying unknown compounds in chondrites.

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Section: Resultsmentioning

confidence: 64%

A laser desorption ionization/matrix‐assisted laser desorption ionization target system applicable for three distinct types of instruments (LinTOF/curved field RTOF, LinTOF/RTOF and QqRTOF) with different performance characteristics from three vendors

Rados

Pittenauer

Frank

et al. 2018

Rapid Comm Mass Spectrometry

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“…We report a sensitive LC–MS workflow for human sweat metabolomics with high coverage. Our method is based on the high-performance chemical isotope labeling (CIL) LC–MS platform for quantitative and in-depth submetabolome profiling. − High-performance CIL uses rationally designed labeling reagents to modify the metabolite’s chemical and physical properties to such an extent that simultaneous improvement in separation, ionization, and quantification can be achieved in LC–MS. For example, 12 C- and 13 C-dansyl labeling LC–MS can be used for relative quantification of the amine/phenol submetabolome with high sensitivity .…”

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confidence: 99%

Comprehensive and Quantitative Profiling of the Human Sweat Submetabolome Using High-Performance Chemical Isotope Labeling LC–MS

2016

Self Cite

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Human sweat can be noninvasively collected and used as a media for diagnosis of certain diseases as well as for drug detection. However, because of very low concentrations of endogenous metabolites present in sweat, metabolomic analysis of sweat with high coverage is difficult, making it less widely used for metabolomics research. In this work, a high-performance method for profiling the human sweat submetabolome based on chemical isotope labeling (CIL) liquid chromatography-mass spectrometry (LC-MS) is reported. Sweat was collected using a gauze sponge style patch, extracted from the gauze by centrifugation, and then derivatized using CIL. Differential (12)C- and (13)C-dansylation labeling was used to target the amine/phenol submetabolome. Because of large variations in the total amount of sweat metabolites in individual samples, sample amount normalization was first performed using liquid chromatography with UV detection (LC-UV) after dansylation. The (12)C-labeled individual sample was then mixed with an equal amount of (13)C-labeled pooled sample. The mixture was subjected to LC-MS analysis. Over 2707 unique metabolites were detected across 54 sweat samples collected from six individuals with an average of 2002 ± 165 metabolites detected per sample from a total of 108 LC-MS runs. Using a dansyl standard library, we were able to identify 83 metabolites with high confidence; many of them have never been reported to be present in sweat. Using accurate mass search against human metabolome libraries, we putatively identified an additional 2411 metabolites. Uni- and multivariate analyses of these metabolites showed significant differences in the sweat submetabolomes between male and female, as well as between early and late exercise. These results demonstrate that the CIL LC-MS method described can be used to profile the human sweat submetabolome with high metabolomic coverage and high quantification accuracy to reveal metabolic differences in different sweat samples, thereby allowing the use of sweat as another human biofluid for comprehensive and quantitative metabolomics research.

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“…Moreover, glutathione (GSH), taurine, and γ-aminobutyric acid together with seven other metabolites were accurately identified and their mass spectra were matched successfully with the standards. Zhou, Huan, and Li (2015) developed two NHS esters, namely, 13 C 0 / 13 C 2 -4-methoxybenzoylamido acetic acid NHS esters ( 13 C 0 / 13 C 2 -MBAA-NHS) and 13 C 0 / 13 C 2 -4-dimethylaminoben -zoylamido acetic acid NHS esters ( 13 C 0 / 13 C 2 -DBAA-NHS) for ICD of amines. The syntheses of these reagents were performed using 4-dimethylaminobenzoic acid (4-DMBA) or 4-methoxybenzoic acid as a substrate and they were subjected to amidation using 13 C 0 / 13 C 2glycine followed by the introduction of NHS to the free carboxylic group of glycine.…”

Section: N-hydroxysuccinimidyl Estersmentioning

confidence: 99%

Current trends in isotope‐coded derivatization liquid chromatographic‐mass spectrometric analyses with special emphasis on their biomedical application

El-Maghrabey

Kishikawa

Kuroda

2020

Biomedical Chromatography

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Currently, LC–MS has various applications in different areas such as metabolomics, pharmacokinetics, and pathological studies. Yet, matrix effects resulting from co‐existing constituents remain a major problem for LC–MS [or LC–tandem mass spectrometry (LC–MS/MS)]. Moreover, technical problems and instrumental drifts may lead to ion abundance variance. Thus, an internal standard (IS) is required to guarantee the accuracy and precision of the method. Because of their limited number, isotope‐coded derivatization (ICD) has been recently introduced to overcome this problem. For ICD, a stable heavy isotope‐coded moiety is used for labeling the standard or the control sample and the formed products can act as ISs. A light form of the reagent is used for labeling the sample. Then, both are mixed and analyzed by LC–MS(/MS). This strategy permits the identification of different unknown analytes including potential metabolites and disease biomarkers. All these attributes lead to persistent growth in the applications of ICD LC–MS(/MS) in various biomedical branches. In this article we review the ICD methods published in the last eight years for biomedical applications as well as briefly summarize other applications for environmental and food analyses as some of their used ICD reagents were further applied for analyzing biological specimens or have the potential for that.

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Development of versatile isotopic labeling reagents for profiling the amine submetabolome by liquid chromatography–mass spectrometry

Cited by 19 publications

References 35 publications

A laser desorption ionization/matrix‐assisted laser desorption ionization target system applicable for three distinct types of instruments (LinTOF/curved field RTOF, LinTOF/RTOF and QqRTOF) with different performance characteristics from three vendors

A laser desorption ionization/matrix‐assisted laser desorption ionization target system applicable for three distinct types of instruments (LinTOF/curved field RTOF, LinTOF/RTOF and QqRTOF) with different performance characteristics from three vendors

Comprehensive and Quantitative Profiling of the Human Sweat Submetabolome Using High-Performance Chemical Isotope Labeling LC–MS

Current trends in isotope‐coded derivatization liquid chromatographic‐mass spectrometric analyses with special emphasis on their biomedical application

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