Strategies for the analysis of chlorinated lipids in biological systems |
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| Institution: | 1. Div. of Natural Sciences, University of California at Merced, PO Box 2039, Merced, CA 95344, USA hforman@ucmerced.edu;2. Dept. of Medicine, University College London Medical School, Rowland Hill St., London, NW3 2PF, UK K.Moore@medsch.ucl.ac.uk;1. Key Laboratory of Zoonosis Research, Ministry of Education/Institute of Zoonosis/College of Veterinary Medicine, Jilin University, Xi An Da Lu 5333, Changchun 130062, PR China;2. Jilin Bussiness and Technology College, Jilin University, Changchun 130062, PR China;1. Department of Chemistry, Warsaw University of Life Sciences (SGGW), ul. Nowoursynowska 159c, 02-776 Warszawa, Poland;2. Institut de Chimie de Nice, UMR 7272, Université Côte d’Azur, CNRS, Parc Valrose, 06108 Nice, France;1. School of Biotechnology and Biomolecular Sciences, UNSW Sydney, New South Wales, 2052, Australia;2. School of Pharmacy, The University of Queensland, Queensland, 4102, Australia;3. Department of Medicine, Boston University School of Medicine, Massachusetts, 02118, United States;1. Nuclear Safety Institute (IBRAE), Russian Academy of Sciences, 52, B. Tulskaya, Moscow 115191, Russia;2. Moscow Institute of Physics and Technology (MIPT) (State University), 9, Institutskii per, Dolgoprudny, Moscow Region 141700, Russia;1. Plasma and Plasmonics Simulation Laboratory, Centre for Energy Studies, Indian Institute of Technology, Delhi 110016, India;2. Shivaji College, University of Delhi, New Delhi 110027, India |
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| Abstract: | Myeloperoxidase-derived HOCl reacts with the vinyl ether bond of plasmalogens yielding α-chlorofatty aldehydes. These chlorinated aldehydes can be purified using thin-layer chromatography, which is essential for subsequent analysis of extracts from some tissues such as myocardium. The α-chlorofatty aldehyde 2-chlorohexadecanal (2-ClHDA) is quantified after conversion to its pentafluorobenzyl oxime derivative using gas chromatography–mass spectrometry and negative-ion chemical ionization detection. 2-ClHDA accumulates in activated human neutrophils and monocytes, as well as in atherosclerotic lesions and infarcted myocardium. Metabolites of 2-ClHDA have also been identified, including the oxidation product, 2-chlorohexadecanoic acid (2-ClHA), and the reduction product, 2-chlorohexadecanol. 2-ClHA can be quantified using LC–MS with selected reaction monitoring (SRM) detection. 2-ClHA can be ω-oxidized by hepatocytes and subsequently β-oxidized from the ω-end, leading to the production of the dicarboxylic acid, 2-chloroadipic acid. This dicarboxylic acid is excreted in the urine and can also be quantified using LC–MS methods with SRM detection. Quantitative analyses of these novel chlorinated lipids are essential to identify the role of these lipids in leukocyte-mediated injury and disease. |
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