Charged tag founded in N-(1-chloroalkyl)pyridinium quaternization for quantification of fatty aldehydes

Cao, Yanjing; Guan, Qing; Qi, Wei; Guo, Yinlong

doi:10.1016/j.aca.2016.05.032

Cited by 16 publications

(19 citation statements)

References 54 publications

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“…Liquid chromatography–mass spectrometry-based approaches have been used extensively to quantify derivatized carbonyl compounds, and recently for screening of unknown carbonyl compounds. Aldehyde derivatizations using 2,4-DNPH [143,197,198,199,200,201,202], dansylhydrazine (DnsHz) [203,204], N -(1-chloroalkyl)pyridinium [205], o -phenyldiamine [206], D-cysteine [207], 9,10-phenanthrenequinone (PQ) [208], 3-nitrophenylhydrazine [209], and 3,4-diaminobenzophenone [210] have been used to provide chromatographic retention and separation, efficient MS ionization, and MS/MS detectability. Typically, LC-MS analysis has been performed using selected reaction monitoring (SRM) with either atmospheric pressure chemical ionization (APCI), atmospheric pressure photoionization (APPI) or electrospray ionization (ESI).…”

Section: Bioanalytical and Mass Spectrometric Methods For Charactementioning

confidence: 99%

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Bioanalytical and Mass Spectrometric Methods for Aldehyde Profiling in Biological Fluids

Dator

Solivio

Villalta

et al. 2019

Toxics

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Human exposure to aldehydes is implicated in multiple diseases including diabetes, cardiovascular diseases, neurodegenerative disorders (i.e., Alzheimer’s and Parkinson’s Diseases), and cancer. Because these compounds are strong electrophiles, they can react with nucleophilic sites in DNA and proteins to form reversible and irreversible modifications. These modifications, if not eliminated or repaired, can lead to alteration in cellular homeostasis, cell death and ultimately contribute to disease pathogenesis. This review provides an overview of the current knowledge of the methods and applications of aldehyde exposure measurements, with a particular focus on bioanalytical and mass spectrometric techniques, including recent advances in mass spectrometry (MS)-based profiling methods for identifying potential biomarkers of aldehyde exposure. We discuss the various derivatization reagents used to capture small polar aldehydes and methods to quantify these compounds in biological matrices. In addition, we present emerging mass spectrometry-based methods, which use high-resolution accurate mass (HR/AM) analysis for characterizing carbonyl compounds and their potential applications in molecular epidemiology studies. With the availability of diverse bioanalytical methods presented here including simple and rapid techniques allowing remote monitoring of aldehydes, real-time imaging of aldehydic load in cells, advances in MS instrumentation, high performance chromatographic separation, and improved bioinformatics tools, the data acquired enable increased sensitivity for identifying specific aldehydes and new biomarkers of aldehyde exposure. Finally, the combination of these techniques with exciting new methods for single cell analysis provides the potential for detection and profiling of aldehydes at a cellular level, opening up the opportunity to minutely dissect their roles and biological consequences in cellular metabolism and diseases pathogenesis.

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Section: Bioanalytical and Mass Spectrometric Methods For Charactementioning

confidence: 99%

“…Another labeling reagent using N -(1-chloroalkyl)pyridinium quaternization to provide a charged tag was developed for quantifying aliphatic fatty aldehydes. This approach is used to measure the levels of long-chain non-volatile fatty acids in thyroid carcinoma tissues [205].…”

Section: Bioanalytical and Mass Spectrometric Methods For Charactementioning

confidence: 99%

Bioanalytical and Mass Spectrometric Methods for Aldehyde Profiling in Biological Fluids

Dator

Solivio

Villalta

et al. 2019

Toxics

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“…N-(1-chloroalkyl)pyridinium quaternization (NAPIQ) is also a new derivatization method for labeling aliphatic aldehydes [127]. Unlike common precharged reagents, uncharged pyridine and thionyl chloride in NAPIQ are designed to add a permanently charged label to the aldehyde.…”

Section: Othersmentioning

confidence: 99%

Progress and Challenges in Quantifying Carbonyl-Metabolomic Phenomes with LC-MS/MS

2021

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Carbonyl-containing metabolites widely exist in biological samples and have important physiological functions. Thus, accurate and sensitive quantitative analysis of carbonyl-containing metabolites is crucial to provide insight into metabolic pathways as well as disease mechanisms. Although reversed phase liquid chromatography electrospray ionization mass spectrometry (RPLC-ESI-MS) is widely used due to the powerful separation capability of RPLC and high specificity and sensitivity of MS, but it is often challenging to directly analyze carbonyl-containing metabolites using RPLC-ESI-MS due to the poor ionization efficiency of neutral carbonyl groups in ESI. Modification of carbonyl-containing metabolites by a chemical derivatization strategy can overcome the obstacle of sensitivity; however, it is insufficient to achieve accurate quantification due to instrument drift and matrix effects. The emergence of stable isotope-coded derivatization (ICD) provides a good solution to the problems encountered above. Thus, LC-MS methods that utilize ICD have been applied in metabolomics including quantitative targeted analysis and untargeted profiling analysis. In addition, ICD makes multiplex or multichannel submetabolome analysis possible, which not only reduces instrument running time but also avoids the variation of MS response. In this review, representative derivatization reagents and typical applications in absolute quantification and submetabolome profiling are discussed to highlight the superiority of the ICD strategy for detection of carbonyl-containing metabolites.

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“…Mass spectrometry coupled with GC or LC is now the most popular technique for the selective and sensitive screening and quantification of molecules in various matrices, particularly with the use of triple-quadrupole mass spectrometers operating in the multiple reaction monitoring (MRM) mode. This technique currently provides the most sensitive detection method when applied to known targeted compounds, and has been extensively used for the analysis of several oxidation products—such as aldehydes and ketones—in various matrices [ 15 , 16 , 17 , 18 , 19 ]. However, depending on the chain length and the unsaturation degree and position of the fatty acids, lipid peroxidation is known to give rise to numerous and various carbonyl compounds.…”

Section: Introductionmentioning

confidence: 99%

Towards Aldehydomics: Untargeted Trapping and Analysis of Reactive Diet-Related Carbonyl Compounds Formed in the Intestinal Lumen

et al. 2021

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Lipid peroxidation and subsequent formation of toxic aldehydes, such as 4-hydroxynonenal, is known to be involved in numerous pathophysiological processes, possibly including the development of colorectal cancer. This work aimed at the development of an untargeted approach using high-performance liquid chromatography coupled with high-resolution mass spectrometry (HPLC–HRMS) for tracking aldehydes in both suspect screening and untargeted methods in fecal water, representing the aqueous environment of colon epithelial cells. This original approach is based on the introduction of a characteristic isotopic labeling by selective derivatization of the carbonyl function using a brominated reagent. Following a metabolomics workflow, the developed methodology was applied to the characterization of aldehyde compounds formed by lipid peroxidation in rats fed two different diets differentially prone to lipoperoxidation. Derivatized aldehydes were first selectively detected on the basis of their isotopic pattern, then annotated and finally identified by tandem mass spectrometry. This original approach allowed us to evidence the occurrence of expected aldehydes according to their fatty acid precursors in the diet, and to characterize other aldehydes differentiating the different diets.

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Charged tag founded in N-(1-chloroalkyl)pyridinium quaternization for quantification of fatty aldehydes

Cited by 16 publications

References 54 publications

Bioanalytical and Mass Spectrometric Methods for Aldehyde Profiling in Biological Fluids

Bioanalytical and Mass Spectrometric Methods for Aldehyde Profiling in Biological Fluids

Progress and Challenges in Quantifying Carbonyl-Metabolomic Phenomes with LC-MS/MS

Towards Aldehydomics: Untargeted Trapping and Analysis of Reactive Diet-Related Carbonyl Compounds Formed in the Intestinal Lumen

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