Effect of phosphatidylcholine chlorohydrins on human erythrocytes

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

Research output: Contribution to journalArticle

Abstract

Hypochlorite generated in vivo under pathological conditions is a known oxidant and chlorinating agent, able to react with proteins and lipids, which affects the stability of biological membranes. Reaction with unsaturated fatty acyl chains in glycerophospholipids such as phosphatidylcholine results in the formation of chlorohydrins. The aim of this study was to determine the effects of chlorohydrins formed by the reaction of hypochlorite with 1-stearoyl-2-oleoyl-, 1-stearoyl-2-linoleoyl-, and 1-stearoyl-2-arachidonylphosphatidylcholine on biophysical properties of bilayers and their effects on human erythrocytes. Using electrospray mass spectrometry we observed complete conversion of the lipids into chlorohydrins, which resulted in a decrease in the rotational correlation time and an increase in the order parameter of liposomes. Unilamellar chlorohydrin liposomes had a lower permeation coefficient for calcein than liposomes made of parent lipids. Flow cytometry demonstrated fast incorporation of uni and multilamellar chlorohydrin liposomes labeled with NBD-phosphatidylethanolamine into erythrocytes. This effect was accompanied by changes in erythrocyte shape (echinocyte formation) and aggregation. Similar but less pronounced effects were noticed for parent lipids only after longer incubation. Chlorohydrins showed also a stronger hemolytic action, proportional to the lipid:erythrocyte ratio. These results are important for understanding the effects of HOCl on mammalian cells, such as might occur in inflammatory pathology.
LanguageEnglish
Pages639-647
Number of pages9
JournalChemistry and Physics of Lipids
Volume163
Issue number7
Early online date1 Jun 2010
DOIs
Publication statusPublished - Sep 2010

Fingerprint

Chlorohydrins
Phosphatidylcholines
Erythrocytes
Liposomes
Lipids
Hypochlorous Acid
Glycerophospholipids
Biological membranes
Unilamellar Liposomes
Flow cytometry
Pathology
Oxidants
Permeation
Mass spectrometry
Mass Spectrometry
Flow Cytometry
Agglomeration
Cells
Membranes

Keywords

  • chlorohydrins
  • erythrocyte aggregation
  • erythrocyte membrane
  • erythrocytes
  • hemolysis
  • humans
  • hypochlorous acid
  • liposomes
  • membrane fluidity
  • phosphatidylcholines

Cite this

Robaszkiewicz, Agnieszka ; Greig, Fiona H. ; Pitt, Andrew R ; Spickett, Corinne M. ; Bartosz, Grzegorz ; Soszyński, Mirosław. / Effect of phosphatidylcholine chlorohydrins on human erythrocytes. In: Chemistry and Physics of Lipids. 2010 ; Vol. 163, No. 7. pp. 639-647.
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Effect of phosphatidylcholine chlorohydrins on human erythrocytes. / Robaszkiewicz, Agnieszka; Greig, Fiona H.; Pitt, Andrew R; Spickett, Corinne M.; Bartosz, Grzegorz; Soszyński, Mirosław.

In: Chemistry and Physics of Lipids, Vol. 163, No. 7, 09.2010, p. 639-647.

Research output: Contribution to journalArticle

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T1 - Effect of phosphatidylcholine chlorohydrins on human erythrocytes

AU - Robaszkiewicz, Agnieszka

AU - Greig, Fiona H.

AU - Pitt, Andrew R

AU - Spickett, Corinne M.

AU - Bartosz, Grzegorz

AU - Soszyński, Mirosław

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N2 - Hypochlorite generated in vivo under pathological conditions is a known oxidant and chlorinating agent, able to react with proteins and lipids, which affects the stability of biological membranes. Reaction with unsaturated fatty acyl chains in glycerophospholipids such as phosphatidylcholine results in the formation of chlorohydrins. The aim of this study was to determine the effects of chlorohydrins formed by the reaction of hypochlorite with 1-stearoyl-2-oleoyl-, 1-stearoyl-2-linoleoyl-, and 1-stearoyl-2-arachidonylphosphatidylcholine on biophysical properties of bilayers and their effects on human erythrocytes. Using electrospray mass spectrometry we observed complete conversion of the lipids into chlorohydrins, which resulted in a decrease in the rotational correlation time and an increase in the order parameter of liposomes. Unilamellar chlorohydrin liposomes had a lower permeation coefficient for calcein than liposomes made of parent lipids. Flow cytometry demonstrated fast incorporation of uni and multilamellar chlorohydrin liposomes labeled with NBD-phosphatidylethanolamine into erythrocytes. This effect was accompanied by changes in erythrocyte shape (echinocyte formation) and aggregation. Similar but less pronounced effects were noticed for parent lipids only after longer incubation. Chlorohydrins showed also a stronger hemolytic action, proportional to the lipid:erythrocyte ratio. These results are important for understanding the effects of HOCl on mammalian cells, such as might occur in inflammatory pathology.

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