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Title

Characterization of glutathione conjugates of chloroacetanilide pesticides using ultra-performance liquid chromatography/quadrupole time-of-flight mass spectrometry and liquid chromatography/ion trap mass spectrometry

AuthorsPérez Solsona, Sandra ; Farkas, Michael; Barceló, Damià ; Aga, Diana S.
KeywordsGlutathione conjugates
Mass spectrometry
Liquid chromatography
Stress-induced
Elucidation GSH
Stable drug-GSH
Biological systems
Issue Date14-Nov-2007
PublisherJohn Wiley & Sons
CitationRapid Communication in Mass Spectrometry 21(24): 4017-4022 (2007)
AbstractGlutathione S-transferases (GSTs) isolated from maize were used to catalyze the conjugation of glutathione (GSH) with chloroacetanilide herbicides, producing stable conjugates that were structurally characterized using ultra-performance liquid chromatography/quadrupole time-of-flight mass spectrometry (UPLC/QqToF-MS) and liquid chromatography/ion trap mass spectrometry (LC/IT-MS). Enzyme-mediated dechlorination of alachlor, metolachlor, and propachlor resulted during GSH conjugation as revealed by the mass spectra of the conjugates, which was confirmed by the loss of the chlorine isotopic signature and from high accurate mass measurements. Several fragmentation patterns in the mass spectra of the chloroacetanilide-GSH conjugates can be used to verify the identities of the enzyme reaction products, such as characteristic ions corresponding to the neutral loss of glutamic acid residue (129 Da) and water (18 Da) observed in the product ion spectrum. For the first time, data are presented showing detection of chloroacetanilides that are conjugated with two GSH molecules, in addition to the known single GSH conjugates.
Description6 pages, 4 figures, 3 tables.-- PMID: 18004742 [PubMed].
Publisher version (URL)http://dx.doi.org/10.1002/rcm.3308
URIhttp://hdl.handle.net/10261/10658
DOIhttp://dx.doi.org/10.1002/rcm.3308
ISSN0951-4198
E-ISSN1097-0231
Appears in Collections:(IDAEA) Artículos
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