The reactions of hypochlorous acid, the reactive oxygen species produced by myeloperoxidase, with lipids

C.M. Spickett, A. Jerlich, O.M. Panasenko, J. Arnhold, A.R. Pitt, T. Stelmaszynska, R.J. Schaur

Research output: Contribution to journalArticle

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Abstract

Myeloperoxidase (MPO), an abundant enzyme in phagocytes, has been implicated in the pathogenesis of various inflammatory diseases including atherosclerosis. The major oxidant produced by MPO, hypochlorous acid (HOCl), is able to modify a great variety of biomolecules by chlorination and/or oxidation. In this paper the reactions of lipids (preferentially unsaturated fatty acids and cholesterol) with either reagent HOCl or HOCl generated by the MPO-hydrogen peroxide-chloride system are reviewed. One of the major issues has been whether the reaction of HOCl with lipids of low density lipoprotein (LDL) yields predominantly chlorohydrins or lipid hydroperoxides. Electrospray mass spectrometry provided direct evidence that chlorohydrins rather than peroxides are the major products of HOCl- or MPO-treated LDL phosphatidylcholines. Nevertheless lipid peroxidation is a possible alternative reaction of HOCl with polyunsaturated fatty acids if an additional radical source such as pre-formed lipid hydroperoxides is available. In phospholipids carrying a primary amino group such as phosphatidylethanolamine chloramines are the preferred products compared to chlorohydrins. Cholesterol can be converted by HOCl to great variety of oxysterols besides three isomers of chlorohydrins. For the situation in vivo it appears that the type of reaction occurring between HOCl and lipids would very much depend on the circumstances, e.g. the pH and the presence of radical initiators. The biological effects of lipid chlorohydrins are not yet well understood. It has been shown that chlorohydrins of both unsaturated fatty acids as well as of cholesterol may cause lysis of target cells, possibly by disruption of membrane structures.
LanguageEnglish
Pages889-899
Number of pages10
JournalActa Biochimica Polonica
Volume47
Issue number4
Publication statusPublished - 2000

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Hypochlorous Acid
Chlorohydrins
Peroxidase
Reactive Oxygen Species
Lipids
Unsaturated Fatty Acids
Lipid Peroxides
Cholesterol
LDL Lipoproteins
Chloramines
Membrane structures
Hydrochloric Acid
Chlorination
Halogenation
Peroxides
Biomolecules
Phagocytes
Phosphatidylcholines
Oxidants
Isomers

Keywords

  • low density lipoprotein
  • hypochlorous acid
  • lipids
  • lipid peroxidation
  • lipid chlorohydrins
  • unsaturated fatty acids

Cite this

Spickett, C. M., Jerlich, A., Panasenko, O. M., Arnhold, J., Pitt, A. R., Stelmaszynska, T., & Schaur, R. J. (2000). The reactions of hypochlorous acid, the reactive oxygen species produced by myeloperoxidase, with lipids. Acta Biochimica Polonica, 47(4), 889-899.
Spickett, C.M. ; Jerlich, A. ; Panasenko, O.M. ; Arnhold, J. ; Pitt, A.R. ; Stelmaszynska, T. ; Schaur, R.J. / The reactions of hypochlorous acid, the reactive oxygen species produced by myeloperoxidase, with lipids. In: Acta Biochimica Polonica. 2000 ; Vol. 47, No. 4. pp. 889-899.
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Spickett, CM, Jerlich, A, Panasenko, OM, Arnhold, J, Pitt, AR, Stelmaszynska, T & Schaur, RJ 2000, 'The reactions of hypochlorous acid, the reactive oxygen species produced by myeloperoxidase, with lipids' Acta Biochimica Polonica, vol. 47, no. 4, pp. 889-899.

The reactions of hypochlorous acid, the reactive oxygen species produced by myeloperoxidase, with lipids. / Spickett, C.M.; Jerlich, A.; Panasenko, O.M.; Arnhold, J.; Pitt, A.R.; Stelmaszynska, T.; Schaur, R.J.

In: Acta Biochimica Polonica, Vol. 47, No. 4, 2000, p. 889-899.

Research output: Contribution to journalArticle

TY - JOUR

T1 - The reactions of hypochlorous acid, the reactive oxygen species produced by myeloperoxidase, with lipids

AU - Spickett, C.M.

AU - Jerlich, A.

AU - Panasenko, O.M.

AU - Arnhold, J.

AU - Pitt, A.R.

AU - Stelmaszynska, T.

AU - Schaur, R.J.

PY - 2000

Y1 - 2000

N2 - Myeloperoxidase (MPO), an abundant enzyme in phagocytes, has been implicated in the pathogenesis of various inflammatory diseases including atherosclerosis. The major oxidant produced by MPO, hypochlorous acid (HOCl), is able to modify a great variety of biomolecules by chlorination and/or oxidation. In this paper the reactions of lipids (preferentially unsaturated fatty acids and cholesterol) with either reagent HOCl or HOCl generated by the MPO-hydrogen peroxide-chloride system are reviewed. One of the major issues has been whether the reaction of HOCl with lipids of low density lipoprotein (LDL) yields predominantly chlorohydrins or lipid hydroperoxides. Electrospray mass spectrometry provided direct evidence that chlorohydrins rather than peroxides are the major products of HOCl- or MPO-treated LDL phosphatidylcholines. Nevertheless lipid peroxidation is a possible alternative reaction of HOCl with polyunsaturated fatty acids if an additional radical source such as pre-formed lipid hydroperoxides is available. In phospholipids carrying a primary amino group such as phosphatidylethanolamine chloramines are the preferred products compared to chlorohydrins. Cholesterol can be converted by HOCl to great variety of oxysterols besides three isomers of chlorohydrins. For the situation in vivo it appears that the type of reaction occurring between HOCl and lipids would very much depend on the circumstances, e.g. the pH and the presence of radical initiators. The biological effects of lipid chlorohydrins are not yet well understood. It has been shown that chlorohydrins of both unsaturated fatty acids as well as of cholesterol may cause lysis of target cells, possibly by disruption of membrane structures.

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KW - low density lipoprotein

KW - hypochlorous acid

KW - lipids

KW - lipid peroxidation

KW - lipid chlorohydrins

KW - unsaturated fatty acids

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Spickett CM, Jerlich A, Panasenko OM, Arnhold J, Pitt AR, Stelmaszynska T et al. The reactions of hypochlorous acid, the reactive oxygen species produced by myeloperoxidase, with lipids. Acta Biochimica Polonica. 2000;47(4):889-899.