Interaction of hypohalous acids and heme peroxidases with unsaturated phosphatidylcholines.
The formation of chlorohydrins, bromohydrins, and iodohydrins from 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) by the myeloperoxidase-hydrogen peroxide-halide system was evaluated by means of matrix-assisted laser desorption/ionisation time-of-flight (MALDI-TOF) mass spectrometry. This approach allows to detect different kinds of the halogenation reaction even in one mass spectrum. Using a mixture of Cl-, Br-, I-, and SCN- at physiological concentrations, a bromination of POPC dominates by the MPO-hydrogen peroxide-halide system. Hypothiocyanite does apparently not react with the double bond of POPC, but increasing amounts of SCN- cause a decrease of the bromohydrin peaks. An interconversion between different hypohalous acids produced by the myeloperoxidase-hydrogen peroxide-halide system determines the pattern of halogenohydrins in POPC. Especially, hypochlorous acid is able to oxidise Br- to hypobromous acid.
Spalteholz
Holger
H
Institute of Medical Physics and Biophysics, Medical Faculty, University of Leipzig, Leipzig, Germany.
Wenske
Kathrin
K
Arnhold
Jürgen
J
D000438:Alcohols / Q000378:metabolism; D001965:Bromides / Q000737:chemistry / Q000378:metabolism; D002712:Chlorides / Q000378:metabolism; D006861:Hydrogen Peroxide / Q000378:metabolism; D006997:Hypochlorous Acid / Q000737:chemistry* / Q000378:metabolism; D007454:Iodides / Q000378:metabolism; D010084:Oxidation-Reduction; D009195:Peroxidase / Q000378:metabolism*; D010713:Phosphatidylcholines / Q000737:chemistry / Q000378:metabolism*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013861:Thiocyanates / Q000378:metabolism
D000438:Alcohols; D001965:Bromides; D002712:Chlorides; D007454:Iodides; D010713:Phosphatidylcholines; D013861:Thiocyanates; C023963:bromohydrins; D006997:Hypochlorous Acid; D006861:Hydrogen Peroxide; D009195:Peroxidase; C028694:1-palmitoyl-2-oleoylphosphatidylcholine