The action of hypochlorous acid on phosphatidylcholine liposomes in dependence on the content of double bonds. Stoichimetry and NMR analysis

Article abstract of DOI:10.1016/0009-3084(95)02484-Z

Kinetics of the consumption of hypochlorous acid in its reaction with double bonds of unsaturated phospholipids and fatty acids were measured using luminol chemiluminescence.Stoichiometry ratios between the consumption of HOCl/OCl^- and the loss of double bonds vary from 2:1 to 1:1.Highest values were found in DMPC liposomes containing 5 molpercent oleic acid or OPPC.With increasing content of double bonds or higher numbers of double bonds in a fatty acid acyl chain ddue to incorporated unsaturated fatty acids or phospholipids in DMPC liposomes the stoichiometry ratio falls continuously to 1:1.A ratio of about 1:1 was observed in multilamellar and unilamellar liposomes composed of egg yolk phosphatidylcholine.Products of the reaction of oleic acid with hypochlorous acid were analysed by 1H-NMR spectroscopy.Chlorohydrins were formed in both DMPC liposomes containing 5 or 40 molpercent oleic acid.Keywords: Hypochlorous acid; Chlorohydrins; Double bond; Phospholipids; Fatty acids