Application of a fluorous derivatization method for characterization of glutathione-trapped reactive metabolites with liquid chromatography–tandem mass spectrometry analysis

Nishijo, Nao; Hayama, Tadashi; Tomita, Ryoko; Yamaguchi, Masatoshi; Fujioka, Toshihiro

doi:10.1016/j.chroma.2020.461160

Cited by 7 publications

(7 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It remains a challenge to analyze these reactive metabolites adducts. Glutathione labeled with a fluorescence tag of dansyl (dGSH) can be applied as a trapping agent for the fluorescent quantification and identification of hard reactive metabolites ( Gan et al, 2005 ; Nishijo et al, 2020 ).On one hand, dGSH can increase the detection sensitivity of trapped reactive metabolites; On the other hand, dGSH captures only soft electrophilic reactive metabolites. CysGlu-Dan labeled cystine have been built to detect soft and hard electrophilic reactive metabolites ( Shibazaki et al, 2021 ).…”

Section: Novel Analytical Techniques Used For Detection Of the Reactive Metabolites Of Natural Productsmentioning

confidence: 99%

Metabolic Activation of the Toxic Natural Products From Herbal and Dietary Supplements Leading to Toxicities

Wang

Xia

et al. 2021

Front. Pharmacol.

View full text Add to dashboard Cite

Currently, herbal and dietary supplements have been widely applied to prevent and treat various diseases. However, the potential toxicities and adverse reactions of herbal and dietary supplements have been increasingly reported, and have gradually attracted widespread attention from clinical pharmacists and physicians. Metabolic activation of specific natural products from herbal and dietary supplements is mediated by hepatic cytochrome P450 or intestinal bacteria, and generates chemical reactive/toxic metabolites that bind to cellular reduced glutathione or macromolecules, and form reactive metabolites-glutathione/protein/DNA adducts, and these protein/DNA adducts can result in toxicities. The present review focuses on the relation between metabolic activation and toxicities of natural products, and provides updated, comprehensive and critical comment on the toxic mechanisms of reactive metabolites. The key inductive role of metabolic activation in toxicity is highlighted, and frequently toxic functional groups of toxic natural products were summarized. The biotransformation of drug cytochrome P450 or intestinal bacteria involved in metabolic activation were clarified, the reactive metabolites-protein adducts were selected as biomarkers for predicting toxicity. And finally, further perspectives between metabolic activation and toxicities of natural products from herbal and dietary supplements are discussed, to provide a reference for the reasonable and safe usage of herbal and dietary supplements.

show abstract

Section: Novel Analytical Techniques Used For Detection Of the Reactive Metabolites Of Natural Productsmentioning

confidence: 99%

Metabolic Activation of the Toxic Natural Products From Herbal and Dietary Supplements Leading to Toxicities

Wang

Xia

et al. 2021

Front. Pharmacol.

View full text Add to dashboard Cite

show abstract

“…S C H E M E 2 Derivatization reactions of carbonylic and carboxylic compounds with 2-hydrazinoquinoline reactive metabolites produced by drug metabolism (Nishijo, Hayama, Tomita, Yamaguchi, & Fujioka, 2020). The GSH-trapped reactive metabolites were obtained after incubation of the test compounds with human liver microsome in the presence of GSH and NADPH.…”

Section: S C H E M E 1 Reaction Between Cyclohexane-13-dione and Aldmentioning

confidence: 99%

“…Chen et al, 2019), but many of them were used for the analysis by gas chromatography. Derivatization of the α ‐carboxyl group from glutathione (GSH) was selectively perfluoroalkylated with the fluorous amine reagent 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11‐ heptadecafluoroundecylamine and used for the screening and characterization of GSH‐trapped reactive metabolites produced by drug metabolism (Nishijo, Hayama, Tomita, Yamaguchi, & Fujioka, 2020). The GSH‐trapped reactive metabolites were obtained after incubation of the test compounds with human liver microsome in the presence of GSH and NADPH.…”

Section: In Situ Derivatizationmentioning

confidence: 99%

Derivatization procedures and their analytical performances for HPLC determination in bioanalysis

David

Moldoveanu

Galaon

2020

Biomedical Chromatography

View full text Add to dashboard Cite

Derivatization, or chemical structure modification, is often used in bioanalysis performed by liquid chromatography technique in order to enhance detectability or to improve the chromatographic performance for the target analytes. The derivatization process is discussed according to the analytical procedure used to achieve the reaction between the reagent and the target compounds (containing hydroxyl, thiol, amino, carbonyl and carboxyl as the main functional groups involved in derivatization). Important procedures for derivatization used in bioanalysis are in situ or based on extraction processes (liquid-liquid, solid-phase and related techniques) applied to the biomatrix. In the review, chiral, isotope-labeling, hydrophobicity-tailored and post-column derivatizations are also included, based on representative publications in the literature during the last two decades. Examples of derivatization reagents and brief reaction conditions are included, together with some bioanalytical applications and performances (chromatographic conditions, detection limit, stability and sample biomatrix).

show abstract

“…[30][31][32][33][34][35][36][37][38] In 2020, Hayama et al generated GSH adducts from biological matrices via uorous derivatization. 12 In their method, GSH adducts were subjected to a trapping assay and then derivatized with a light uorous tag. The compounds were separated using LC/MS equipped with a uorous silica gel column.…”

mentioning

confidence: 99%

“…Each compound was identied by their highresolution MS (HRMS) m/z values and known adducts of cysteine or GSH (M + Rf 8 CYS + O for ethynylbenzene; M + Rf 8 CYS-2H for troglitazone, ticlopidine, clozapine, and amodiaquine; and M + Rf 8 CYS-4H-O for abacavir). 12,13,17,18,23,25,[40][41][42] For ticlopidine, an unprecedented metabolite adduct (M + Rf 8 CYS-S + O) was observed, possibly due to the improved MS sensitivity of Rf 8 CYS. Ticlopidine has a thiophene ring which is expected to metabolize into an a,b-unsaturated carbonyl compound based on a previous report.…”

mentioning

confidence: 99%

Development of a fluorous trapping reagent for rapid detection of electrophilic reactive metabolites

Akagi,

Yamakoshi,

Iwabuchi

2024

Anal. Methods

View full text Add to dashboard Cite

show abstract

Application of a fluorous derivatization method for characterization of glutathione-trapped reactive metabolites with liquid chromatography–tandem mass spectrometry analysis

Cited by 7 publications

References 29 publications

Metabolic Activation of the Toxic Natural Products From Herbal and Dietary Supplements Leading to Toxicities

Metabolic Activation of the Toxic Natural Products From Herbal and Dietary Supplements Leading to Toxicities

Derivatization procedures and their analytical performances for HPLC determination in bioanalysis

Development of a fluorous trapping reagent for rapid detection of electrophilic reactive metabolites

Contact Info

Product

Resources

About