Effect of phosphatidylcholine chlorohydrins on human erythrocytes

Robaszkiewicz, Agnieszka; Greig, Fiona H.; Pitt, Andrew R.; Spickett, Corinne M.; Bartosz, Grzegorz; Soszyński, Mirosław

doi:10.1016/j.chemphyslip.2010.05.201

Cited by 14 publications

(15 citation statements)

References 38 publications

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“…However, questions about the mechanism of toxicity to cells remain. Here, we confirmed the toxicity of [18]. A later study reported that SOPC chlorohydrin induced apoptosis of U937 monocytic cells with the activation of caspase-3 [21].…”

Section: Discussionsupporting

confidence: 75%

“…In 15 terms of cell membrane localization of HOCl-modified lipids, the structure of the lipid molecule is likely to be of crucial importance as it may affect the local membrane environment. As we demonstrated previously, an increase in level of chlorination was accompanied by an increase in liposome membrane rigidity and erythrocyte lysis [18]. Such alterations in cellular membrane structure or intracellular membranes may impair or trigger signaling pathways and intracellular events, e.g.…”

Section: Discussionmentioning

confidence: 78%

“…apoptosis induction and cell cycle progression). As mentioned above, phosphatidylcholine chlorohydrins (which are demonstrated in the current study and previously published papers [15,18,20] as major products of the reaction between HOCl and phosphatidylcholines) were shown to induce ROS production in splenocytes, thereby acting as less reactive but long-lasting mediators of HOCl oxidative action. Immortalized Human Umbilical Vein Endothelial Cells (HUVEC-ST) were used as a model cells.1-stearoyl-2-oleoyl-, 1-stearoyl-2-linoleoyl-, and 1-stearoyl-2-arachidonyl-phosphatidylcholinewere exposed to HOCl as described previously, and the products were subjected to more precise analysis (MS/MS and NMR) in order to confirm high abundance of lipid chlorohydrins in the mixture of HOCl-modified products [18].…”

Section: Introductionmentioning

confidence: 89%

“…Early work showed that pre-formed fatty acid chlorohydrins caused lysis of red blood cells, which was thought to involve a physical disruption of the membrane [14]. Our recent work on this topic has demonstrated that phospholipid chlorohydrins are taken up more rapidly than the corresponding unmodified lipids by red blood cells, and incorporated into the membrane [18]. Phospholipid chloro-and bromohydrins were found to cause toxicity to human umbilical vein endothelial cells (HUVECs), determined by leakage of chromium from the cells [19], while in cultured myeloid cells several phospholipid chlorohydrins were observed to cause deletion of ATP and loss of viability according to the MTT assay [20].…”

Section: Introductionmentioning

confidence: 99%

“…The incorporation of liposomes into HUVEC-ST cells was analyzed using NBD-labeled liposomes prepared according to a previously described method [18], which were added to cells (plated the day before the experiment on a black 96-well plate) and incubated for selected time periods. After three cycles of washing with PBS, fluorescence was measured at 485/538 nm.…”

Section: Synthesis Of Lipid Chlorohydrinsmentioning

confidence: 99%

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HOCl-modified phosphatidylcholines induce apoptosis and redox imbalance in HUVEC-ST cells

Robaszkiewicz

Bartosz

Pitt

et al. 2014

Archives of Biochemistry and Biophysics

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Electrophilic attack of hypochlorous acid on unsaturated bonds of fatty acyl chains is known to result mostly in chlorinated products that show cytotoxicity to some cell lines and were found in biological systems exposed to HOCl. This study aimed to investigate more deeply the products and the mechanism underlying cytotoxicity of phospholipid-HOCl oxidation products, synthesized by the reaction of HOCl with 1-stearoyl-2-oleoyl-, 1-stearoyl-2-linoleoyl-, and 1-stearoyl-2-arachidonyl-phosphatidylcholine. Phospholipid chlorohydrins were found to be the most abundant among obtained products. HOCl-modified lipids were cytotoxic towards HUVEC-ST (endothelial cells), leading to a decrease of mitochondrial potential and an increase in the number of apoptotic cells. These effects were accompanied by an increase of the level of active caspase-3 and caspase-7, while the caspase-3/-7 inhibitor Ac-DEVD-CHO dramatically decreased the number of apoptotic cells. Phospholipid-HOCl oxidation products were shown to affect cell proliferation by a concentration-dependent cell cycle arrest in the G 0 /G 1 phase and activating redox sensitive p38 kinase. The redox imbalance observed in HUVEC-ST cells exposed to modified phosphatidylcholines was accompanied by an increase in ROS level, and a decrease in glutathione content and antioxidant capacity of cell extracts.

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Section: Discussionsupporting

confidence: 75%

Section: Discussionmentioning

confidence: 78%

Section: Introductionmentioning

confidence: 89%

Section: Introductionmentioning

confidence: 99%

Section: Synthesis Of Lipid Chlorohydrinsmentioning

confidence: 99%

See 3 more Smart Citations

HOCl-modified phosphatidylcholines induce apoptosis and redox imbalance in HUVEC-ST cells

Robaszkiewicz

Bartosz

Pitt

et al. 2014

Archives of Biochemistry and Biophysics

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Lipid Oxidation

Fauzi¹,

Spickett²

2015

Oxidative Stress in Applied Basic Research and Clinical Practice

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Mass spectrometry and inflammation—MS methods to study oxidation and enzyme-induced changes of phospholipids

Fuchs

2013

Anal Bioanal Chem

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Many diseases such as arthritis or atherosclerosis are accompanied by inflammatory processes. Inflammation is characterized by the infiltration of cells such as neutrophilic granulocytes and (a) the release of phospholipases [particularly phospholipase A2 (PLA2)] and (b) the generation of reactive oxygen as well as nitrogen species (ROS and RNS). While PLA2 leads to defined lyso products (lacking one acyl residue), lipid oxidation is characterized by much more complex product patterns, including lipid peroxides, aldehydes (by double bond cleavage), and many others. Nevertheless, oxidation processes are highly important under in vivo conditions because molecules with regulatory functions are generated by the oxidation of lipids and/or free fatty acids. Therefore, lipid oxidation products as well as lysolipids are increasingly assumed to represent important disease (bio)markers. Consequently, there is also increasing interest in methods to characterize these products qualitatively and quantitatively.Mass spectrometry (MS) seems to be the method of choice to study (phospho)lipids changed under inflammatory conditions: nowadays, soft ionization MS methods are regularly used to study oxidative lipid modifications because of their high sensitivities and the tremendous mass resolutions that are achievable by using modern mass spectrometers. However, experimental care is required to be able to detect all relevant products. Although electrospray ionization (ESI) MS is so far most popular, applications of matrix-assisted laser desorption and ionization (MALDI) MS are continuously increasing. This review aims to summarize the so far available data on MS analyses of oxidized lipids as well as lysolipids. In addition to model systems, special attention will be paid to the monitoring of oxidized lipids and lysolipids under in vivo conditions. It is the aim of this review to provide a critical survey of the advantages and drawbacks of the different MS methods, with the focus on MALDI and ESI.

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Effect of phosphatidylcholine chlorohydrins on human erythrocytes

Cited by 14 publications

References 38 publications

HOCl-modified phosphatidylcholines induce apoptosis and redox imbalance in HUVEC-ST cells

HOCl-modified phosphatidylcholines induce apoptosis and redox imbalance in HUVEC-ST cells

Lipid Oxidation

Mass spectrometry and inflammation—MS methods to study oxidation and enzyme-induced changes of phospholipids

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