[64] Measurement of reaction products from hypochlorous acid and unsaturated lipids

Berg, J. Van Den; Winterbourn, C C

doi:10.1016/s0076-6879(94)33067-0

Cited by 18 publications

(6 citation statements)

References 7 publications

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“…In addition, our analyses showed that the levels of fatty acids and glycerol esters of fatty acids were affected by HOCl stress. Fatty acids and compounds of the cell membrane are among the first components encountering HOCl molecules [ 45 , 46 ]. It is a known mechanism that bacterial cells alter their membrane composition and cell envelope structure to antagonize HOCl stress, corroborating our observations [ 22 , 38 ].…”

Section: Discussionmentioning

confidence: 99%

Metabolic Response of Escherichia coli upon Treatment with Hypochlorite at Sub-Lethal Concentrations

et al. 2015

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Hypochlorite is a reactive oxygen species that is worldwide as an antibacterial disinfectant. Hypochlorite exposure is known to cause oxidative damage to DNA and proteins. As a response to these effects, the metabolite profiles of organisms treated with sub-lethal doses of hypochlorite are assumed to be severely modified; however, the nature of these changes is hardly understood. Therefore, using nuclear magnetic resonance spectroscopy and gas chromatography-coupled mass spectrometry, we analyzed the time-dependent impact of hypochlorite exposure with a sub-lethal concentration (50 µM) on the metabolite profile of the Escherichia coli strain MG1655. Principle component analysis clearly distinguished between the metabolite profiles of bacteria treated for 0, 5,10, 20, 40, or 60 min. Major changes in the relative amounts of fatty acids, acetic acid, and formic acid occurred within the first 5 min. Comparative gas chromatography-coupled mass spectrometry analyses revealed that the amounts of free methionine and alanine were significantly decreased in the treated cells, demonstrating their susceptibility to hypochlorite exposure. The concentrations of succinate, urea, orotic acid, 2-aminobutyric acid, and 2-hydroxybutyric acid were also severely affected, indicating general changes in the metabolic network by hypochlorite. However, most metabolite levels relaxed to the reference values of untreated cells after 40–60 min, reflecting the capability of E. coli to rapidly adapt to environmental stress factors such as the presence of sub-lethal oxidant levels.

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Section: Discussionmentioning

confidence: 99%

Metabolic Response of Escherichia coli upon Treatment with Hypochlorite at Sub-Lethal Concentrations

et al. 2015

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“…In the next series of experiments, we investigated whether consumption of HDL 3 fatty acids by NaOCl is accompanied by the formation of fatty acid chlorohydrins. Chlorohydrin formation was followed by GC-MS, essentially as described by van den Berg et al (28,34). The total ion current (TIC) trace of NaOCl-modified HDL 3 lipid extracts revealed the occurrence of two peak clusters with retention times of 28.02 and 28.51 min not present in native HDL 3 lipids (Fig.…”

Section: Effect Of Naocl Modification On Hdlmentioning

confidence: 94%

“…HDL 3 modification in the presence of the MPO/H 2 O 2 /Cl Ϫ system was performed at pH 7.4 or 4.5 to generate HOCl or Cl 2 as the oxidant (28,29). Briefly, to the substrates (1 mg of HDL 3 protein/ml in PBS (50 mM, pH 7.4) or in sodium phosphate (50 mM, 100 M diethylenetriamine pentaacetic acid, pH 4.5)) additions of 20 M H 2 O 2 were made at 10-min intervals at 37°C until reaching a total of 15 additions (final concentration 300 M; assuming quantitative conversion, a molar oxidant: lipoprotein ratio of ϳ20:1 could be expected).…”

Section: Mpo Modification Of Hdlmentioning

confidence: 99%

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Effects of Reagent and Enzymatically Generated Hypochlorite on Physicochemical and Metabolic Properties of High Density Lipoproteins

Panzenboeck

Raitmayer

Reicher

et al. 1997

Journal of Biological Chemistry

102

105

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Myeloperoxidase (MPO),In contrast to low density lipoproteins (LDL), 1 high plasma concentrations of high density lipoproteins (HDL) are associated with a decreased risk for the development of coronary artery disease, an effect commonly attributed to their central role in reverse cholesterol transport (1). During this process, HDL is able to promote efflux of cholesterol from peripheral tissues, and the accepted cholesterol is (at least in part) esterified by the action of lecithin-cholesterol acyltransferase (2). Cholesteryl esters (CEs) formed by the lecithin-cholesterol acyltransferase reaction are then transferred from HDL to other lipoproteins mediated by the cholesterol ester transfer protein or are delivered to the liver for bilary secretion or reutilization during lipoprotein assembling (3).Within the oxidative theory, HDL appears to be Janus-faced (4 -6). The majority of lipid hydroperoxides (the first detectable products of lipoprotein oxidation) in plasma are transported in the HDL fraction (7), and HDL was suggested to act as a sink for preformed lipid hydro(pero)xides. HDL-associated cholesteryl ester hydroperoxides, which are probably transferred to HDL by the action of the cholesterol ester transfer protein (8), are preferentially catabolized over nonoxidized CEs; this was shown in HepG2 cells (9), in situ perfused rat liver (10), and intact rats (11). HDL was also shown to protect LDL from lipid peroxidation, inhibiting the formation of lipid hydroperoxides but not the formation of conjugated dienes (12). On the other hand, HDL is more easily oxidized than LDL (7), HDLassociated lecithin-cholesterol acyltransferase is modified by reactive short and long chain aldehydes (13), and the ability of oxidatively modified HDL to promote cellular cholesterol efflux is diminished (14 -16), most probably due to alterations in its apolipoprotein moiety. During the acute phase response, up to 80% of apolipoprotein A-I (apoA-I), the major apolipoprotein of HDL, is displaced by serum amyloid A (17), and due to this exchange in the HDL apolipoprotein domain, native, anti-inflammatory HDL became proinflammatory during the acute phase response (18). The above mentioned results imply that HDL can protect LDL against oxidative modifications and could serve as a vehicle for detoxification of potentially (cyto)-toxic lipid hydroperoxides. However, under certain circumstances many of the important physiological properties of HDL can be lost during oxidation/modification, transforming HDL into a proatherogenic lipoprotein particle.

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“…There are not many methods [216] for evaluating the generation of lipid chlorohydrins apart from MS, but at least a few of them should be shortly mentioned.…”

Section: Analysis Of Chlorinated Lipids Using Different Mass Spectmentioning

confidence: 99%

Chlorinated Phospholipids and Fatty Acids: (Patho)physiological Relevance, Potential Toxicity, and Analysis of Lipid Chlorohydrins

Schröter

Schiller

2016

Oxidative Medicine and Cellular Longevity

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Chlorinated phospholipids are formed by the reaction of hypochlorous acid (HOCl), generated by the enzyme myeloperoxidase under inflammatory conditions, and the unsaturated fatty acyl residues or the head group. In the first case the generated chlorohydrins are both proinflammatory and cytotoxic, thus having a significant impact on the structures of biomembranes. The latter case leads to chloramines, the properties of which are by far less well understood. Since HOCl is also widely used as a disinfecting and antibacterial agent in medicinal, industrial, and domestic applications, it may represent an additional source of danger in the case of abuse or mishandling. This review discusses the reaction behavior of in vivo generated HOCl and biomolecules like DNA, proteins, and carbohydrates but will focus on phospholipids. Not only the beneficial and pathological (toxic) effects of chlorinated lipids but also the importance of these chlorinated species is discussed. Some selected cleavage products of (chlorinated) phospholipids and plasmalogens such as lysophospholipids, (chlorinated) free fatty acids and α-chloro fatty aldehydes, which are all well known to massively contribute to inflammatory diseases associated with oxidative stress, will be also discussed. Finally, common analytical methods to study these compounds will be reviewed with focus on mass spectrometric techniques.

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[64] Measurement of reaction products from hypochlorous acid and unsaturated lipids

Cited by 18 publications

References 7 publications

Metabolic Response of Escherichia coli upon Treatment with Hypochlorite at Sub-Lethal Concentrations

Metabolic Response of Escherichia coli upon Treatment with Hypochlorite at Sub-Lethal Concentrations

Effects of Reagent and Enzymatically Generated Hypochlorite on Physicochemical and Metabolic Properties of High Density Lipoproteins

Chlorinated Phospholipids and Fatty Acids: (Patho)physiological Relevance, Potential Toxicity, and Analysis of Lipid Chlorohydrins

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