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Synthetic cholinecontaining phospholipids comprise a new class of compounds with antineoplastic properties. We have investigated the effect of recently synthesized glucosecontaining analogs of lysophosphatidylcholine (glyceroglucophospholipid, GlcPC) and of lysoplatelet activating factor (GlcPAF) and its C16, C14 and C12 derivatives (ET-16, ET-14, and ET-12) on proliferation of immortalized human keratinocyte (HaCaT) cells. The data were compared to the ability of the compounds to intercalate into phosphatidylserine liposomes and to form lesions in planar bilayer membranes. A correlation between bioactivity and membrane activity was found. The number of molecules that intercalated into phosphatidylserine liposomes depended on the chemical structure of the compounds and was in the order GlcPAF [almost equal to] ET-16 [almost equal to] ET-14 [greater than] GlcPC [greater than] ET-12. All compounds induced membrane lesions, and the lesion forming activity was in the same order. Similar activity rankings were found for the release of lactate dehydrogenase from HaCaT cells as a measure of lytic activity and for the influence on cell number as a measure of proliferation. In the latter test, however, proliferation was already inhibited at nontoxic concentrations. From these findings, it may be concluded that the intercalation of the compounds at toxic concentrations leads to the formation of membrane lesions and finally results in membrane rupture leading to cell death.

Structure-Dependent Effects of Glucose-Containing Analogs of Platelet Activating Factor (PAF) on Membrane Integrity