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Reactive chlorinating species produced during neutrophil activation target tissue plasmalogens: production of the chemoattractant, 2-chlorohexadecanal.

Abstract
Recently alpha-chloro fatty aldehydes have been shown to be products of reactive chlorinating species targeting the vinyl ether bond of plasmalogens utilizing a cell-free system. Accordingly, the present experiments were designed to show that alpha-chloro fatty aldehydes are produced by activated neutrophils and to determine their physiologic effects. A sensitive gas chromatography-mass spectrometry technique was developed to detect pentafluorobenzyl oximes of alpha-chloro fatty aldehydes utilizing negative ion chemical ionization. Phorbol 12-myristate 13-acetate activation of neutrophils resulted in the production of both 2-chlorohexadecanal and 2- chlorooctadecanal through a myeloperoxidase-dependent mechanism that likely involved the targeting of both 16 and 18 carbon vinyl ether-linked aliphatic groups present in the sn-1 position of neutrophil plasmalogens. 2-Chlorohexadecanal was also produced by fMLP-treated neutrophils. Additionally, reactive chlorinating species released from activated neutrophils targeted endothelial cell plasmalogens resulting in 2-chlorohexadecanal production. Physiologically relevant concentrations of 2-chlorohexadecanal induced neutrophil chemotaxis in vitro suggesting that alpha-chloro fatty aldehydes may have a role in neutrophil recruitment. Taken together, these studies demonstrate for the first time a novel biochemical mechanism that targets the vinyl ether bond of plasmalogens during neutrophil activation resulting in the production of alpha-chloro fatty aldehydes that may enhance the recruitment of neutrophils to areas of active inflammation.
AuthorsArun K Thukkani, Fong-Fu Hsu, Jan R Crowley, Robert B Wysolmerski, Carolyn J Albert, David A Ford
JournalThe Journal of biological chemistry (J Biol Chem) Vol. 277 Issue 6 Pg. 3842-9 (Feb 8 2002) ISSN: 0021-9258 [Print] United States
PMID11724792 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, P.H.S.)
Chemical References
  • 2-chlorohexadecanal
  • Aldehydes
  • Plasmalogens
  • Chlorine
Topics
  • Aldehydes (metabolism)
  • Animals
  • Cattle
  • Cells, Cultured
  • Chlorine (metabolism)
  • Endothelium, Vascular (cytology, metabolism)
  • Gas Chromatography-Mass Spectrometry
  • Humans
  • Neutrophil Activation
  • Plasmalogens (metabolism)

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