Quantitative analysis of hemolytic action of lysophosphatidylcholines in vitro: Effect of acyl chain structure.

Handa, Tetsurou; Miyajima, Koichiro; Mikura, Yasushi; Shimizu, Hisayoshi; Toguchi, Hajime

doi:10.1248/cpb.36.4253

Cited by 28 publications

(16 citation statements)

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“…The final concentration was 50 mM. The critical micelle concentration of oleoyl lyso-PC is 2 mM in phosphate-buffered saline (28). The micelles were incubated for 1 h at 23 C before size measurement.…”

Section: Size Determination Of Extruded Unilamellar Vesiclesmentioning

confidence: 99%

Natural Ceramides and Lysophospholipids Cosegregate in Fluid Phosphatidylcholine Bilayers

Sazzad

Möuts

Palacios-Ortega

et al. 2019

Biophysical Journal

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The mode of interactions between palmitoyl lysophosphatidylcholine (palmitoyl lyso-PC) or other lysophospholipids (lyso-PLs) and palmitoyl ceramide (PCer) or other ceramide analogs in dioleoylphosphatidylcholine (DOPC) bilayers has been examined. PCer is known to segregate laterally into a ceramide-rich phase at concentrations that depend on the nature of the ceramides and the co-phospholipids. In DOPC bilayers, PCer forms a ceramide-rich phase at concentrations above 10 mol%. In the presence of 20 mol% palmitoyl lyso-PC in the DOPC bilayer, the lateral segregation of PCer was markedly facilitated (segregation at lower PCer concentrations). The thermostability of the PCer-rich phase in the presence of palmitoyl lyso-PC was also increased compared to that in the absence of palmitoyl lyso-PC. Other saturated lyso-PLs (e.g., palmitoyl lyso-phosphatidylethanolamine and lyso-sphingomyelin) also facilitated the lateral segregation of PCer in a similar manner as palmitoyl lyso-PC. When examined in the DOPC bilayer, it appeared that the association between palmitoyl lyso-PC and PCer was equimolar in nature. It is proposed that the interaction of PCer with lyso-PLs was driven by the need of ceramide to obtain a large-headgroup co-lipid, and saturated lyso-PLs were preferred co-lipids over DOPC because of the nature of their acyl chain. Structural analogs of PCer (1-or 3-deoxy-PCer) were also associated with palmitoyl lyso-PC, similarly to PCer, suggesting that the ceramide/lyso-PL interaction was not sensitive to structural alterations in the ceramide molecule. Binary complexes containing palmitoyl lyso-PC and ceramide were prepared, and these had a bilayer structure as ascertained by transmission electron microscopy. It is concluded that ceramides and lyso-PLs associated with each other both in binary bilayers and in ternary systems based on the DOPC bilayers. This association may have biological relevance under conditions in which both sphingomyelinases and phospholipase A 2 enzymes are activated, such as during inflammatory processes.

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Section: Size Determination Of Extruded Unilamellar Vesiclesmentioning

confidence: 99%

Natural Ceramides and Lysophospholipids Cosegregate in Fluid Phosphatidylcholine Bilayers

Sazzad

Möuts

Palacios-Ortega

et al. 2019

Biophysical Journal

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“…The proportion of the hydrophilic group to the hydrophobic group in LPC is greater than that in PC, and the ability of the emulsification of LPC is characteristically great. LPC also, however, causes hemolysis because LPC has not only the ability of emulsification but also very high solubility, and thus a fat emulsion using LPC as the emulsifier cannot be used for parenteral emulsions [8,9].…”

Section: Resultsmentioning

confidence: 99%

Physicochemical properties of structured phosphatidylcholine in drug carrier lipid emulsions for drug delivery systems

Kawaguchi

Shimokawa

Ishii

2008

Colloids and Surfaces B: Biointerfaces

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“…Quinn et al [17] have shown LPC to be a potent and specific chemoattractant for monocytes. This substance is cytotoxic to various cells, including myocardial cells [18], lymphocytes [19], erythrocytes [20], alveolar epithelial cells [21], and human lymphoma Raji cells [22].…”

Section: Discussionmentioning

confidence: 99%

Comparative toxicity of oxidatively modified low-density lipoprotein and lysophosphatidylcholine in cultured vascular endothelial cells

et al. 1994

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Oxidative modification of low-density lipoprotein (LDL) may play an important role in the initiation and progression of atherosclerosis. We previously showed that the cytotoxicity of oxidized LDL (oxLDL) depended on the level of lipid hydroperoxides. Meanwhile, it has been shown that during LDL oxidation, a significant part of the LDL phosphatidylcholine (PC) is degraded to lysophosphatidylcholine (LPC) by an intrinsic phospholipase A2-like activity, and that LPC is toxic to various cells. In the present study, we compared the toxicity of oxLDL with that of LPC in cultured bovine aortic endothelial cells. Cytotoxicity induced by LPC, assessed by the release of lactate dehydrogenase (LDH), reached a plateau within 1 h. LDH release induced by oxLDL occurred much later, at about 3 h, and increased linearly until nearly all the LDH was released at 10 h. The addition of deferoxamine, a Fe3+ chelator, to the reaction medium prevented the toxic effects of oxLDL, but not of LPC. Native LDL and oxLDL inhibited the toxicity of LPC, while native LDL promoted the toxicity of oxLDL. Albumin inhibited the toxicity of LPC but not of oxLDL. Preincubation of endothelial cells with an antioxidant, probucol, protected against oxLDL toxicity, but not against LPC toxicity. These results suggest that lipid hydroperoxides associated with the oxLDL particle, not LPC, constitute the toxic moiety of oxLDL. These substances may generate lipid peroxyl and alkoxyl radicals in the presence of ionic iron, probably from intracellular iron stores in endothelial cells, and produce cytotoxicity.

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Quantitative analysis of hemolytic action of lysophosphatidylcholines in vitro: Effect of acyl chain structure.

Cited by 28 publications

References 0 publications

Natural Ceramides and Lysophospholipids Cosegregate in Fluid Phosphatidylcholine Bilayers

Natural Ceramides and Lysophospholipids Cosegregate in Fluid Phosphatidylcholine Bilayers

Physicochemical properties of structured phosphatidylcholine in drug carrier lipid emulsions for drug delivery systems

Comparative toxicity of oxidatively modified low-density lipoprotein and lysophosphatidylcholine in cultured vascular endothelial cells

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