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Redox Report
Communications in Free Radical Research
Volume 3, 1997 - Issue 5-6
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Original Articles

Modification of red cell membrane lipids by hypochlorous acid and haemolysis by preformed lipid chlorohydrins

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Pages 263-271 | Received 16 Oct 1997, Accepted 18 Dec 1997, Published online: 13 Jul 2016

REFERENCES

  • Nunez J. Thyroid hormones: mechanism of phenoxy ether formation. Methods Enzymol 1984; 107: 476–488.
  • Winterbourn C C. Comparative reactivities of various biological compounds with myeloperoxidase-hydrogen peroxide-chloride, and similarity of the oxidant to hypochlorite. Biochim Biophys Acta 1985; 840: 204–210.
  • Albrich J M, McCarthy C A, Hurst J K. Biological reactivity of hypochlorous acid: Implications for microbicidal mechanisms of leukocyte myeloperoxidase. Proc Natl Acad Sci USA 1981; 78: 210–214.
  • Winterbourn C C, van den Berg J J M, Roitman E, Kuypers F A. Chlorohydrin formation from unsaturated fatty acids reacted with hypochlorous acid. Arch Biochem Biophys 1992; 296: 547–555.
  • van den Berg J J M, Winterbourn C C, Kuypers F A. Hypochlorous acid-mediated oxidation of cholesterol and phospholipid: Analysis of reaction products by gas chromatography-mass spectrometry. J Lipid Res 1993; 34: 2005–2012.
  • Carr A C, van den Berg J J M, Winterbourn C C. Chlorination of cholesterol in cell membranes by hypochlorous acid. Arch Biochem Biophys 1996; 332: 63–69.
  • Heinecke J W, Li W, Mueller D M, Bohrer A, Turk J. Cholesterol chlorohydrin synthesis by the myeloperoxidase-hydrogen peroxide-chloride system: potential markers for lipoproteins oxidatively damaged by phagocytes. Biochemistry 1994; 33: 10127–10136.
  • Hazen S L, Hsu F F, Duffin K, Heinecke J W. Molecular chlorine generated by the myeloperoxidase-hydrogen peroxide-chloride system of phagocytes converts low density lipoprotein cholesterol into a family of chlorinated sterols. J Biol Chem 1996; 271: 23080–23088.
  • Carr A C, Winterbourn C C, Blunt J W, Phillips A J, Abell A D. Nuclear magnetic resonance characterisation of 6a-chloro-5b-cholestane-3b,5-diol formed from the reaction of hypochlorous acid with cholesterol. Lipids 1997; 32: 363–367.
  • Domigan N M, Carr A C, Elder P A, Lewis J G, Winterbourn C C. A monoclonal antibody recognising the chlorohydrin derivatives of oleic acid for probing hypochlorous acid involvement in tissue injury. Redox Report 1997; 3: 57–63.
  • van den Berg J J M, Cook N E, Tribble D L. Reinvestigation of the antioxidant properties of conjugated linoleic acid. Lipids 1995; 30: 599–605.
  • Theunissen J J H, Jackson R L, Kempen H J M, Demel R A. Membrane properties of oxysterols. Interfacial orientation, influence on membrane permeability and redistribution between membranes. Biochim Biophys Acta 1986; 860: 66–74.
  • Streuli R A, Chung J, Scanu A M, Yachnin S. Serum lipoprotein modulate oxygenated sterol insertion into human red cell membranes. Science 1981; 212: 1294–1296.
  • Wharton S A, Green C. Effect of sterol structure on the transfer of sterols and phospholipids from liposomes to erythrocytes in vitro. Biochim Biophys Acta 1982; 711: 398–402.
  • Sepe S M, Clark R A. Oxidant membrane injury by the neutrophil myeloperoxidase system. I Characterization of a liposome model and injury by myeloperoxidase, hydrogen peroxide and halides. J Immunol 1985; 134: 1888–1895.
  • Sepe S M, Clark R A. Oxidant membrane injury by the neutrophil myeloperoxidase system. II. Injury by stimulated neutrophils and protection by lipid soluble antioxidants. J Immunol 1985; 134: 1896–1901.
  • Dallegri F, Patrone F, Bonvini E, Gahrton G, Holm G, Sacchetti C. Ox erythrocyte cytotoxicity by phorbol myristate acetate-activated human neutrophils. Scand J Immunol 1983; 17: 109–114.
  • Dallegri F, Ballestrero A, Frumento G, Patrone F. Erythrocyte lysis by PMA-triggered neutrophil polymorphonuclears: evidence for an hypochlorous acid-dependent process. Immunology 1985; 55: 639–645.
  • Dallegri F, Ballestrero A, Frumento G, Patrone F. Role of hypochlorous acid and chloramines in the extracellular cytolysis by neutrophil polymorphonuclear leukocytes. J Clin Lab Immunol 1986; 20: 37–41.
  • Vissers M C M, Stern A, Kuypers F, van den Berg J J M, Winterbourn C C. Hypochlorous acid-mediated injury to human red blood cells: an investigation into the mechanism of lysis. Free Radical Biol Med 1994; 16: 703–712.
  • Kettle A J, Winterbourn C C. Assays for the chlorination activity of myeloperoxidase. Methods Enzymol. 1994; 233: 502–512.
  • Rose H G, Oklander M. Improved procedure for the extraction of lipids from human erythrocytes. J Lipid Res 1965; 6: 428–431.
  • Awasthi Y C, Garg H S, Dao D D, Partridge C A, Srivastava S K. Enzymatic conjugation of erythrocyte glutathione with 1-chloro-2,4-dinitrobenzene: The fate of glutathione conjugate in erythrocytes and the effect of glutathione depletion on hemoglobin. Blood 1981; 58: 733–738.
  • Vissers M C M, Winterbourn C C. Oxidation of intracellular glutathione after exposure of red cells to hypochlorous acid. Biochem J 1995; 307: 57–62.
  • Brito R M M, Vaz W L C. Determination of the critical micelle concentration of surfactants using the fluorescent probe N-phenyl-1-napthylamine. Anal Biochem 1986; 152: 250–255.
  • Boyland E, Chasseaud L F. The role of glutathione and glutathione S-transferases in mercapturic add biosynthesis. Adv Enzymol 1969; 32: 173–219.
  • Lubin B H, Kuypers F A, Chiu D T, Shohet S B. Analysis of red cell membrane lipids. Methods Hematol 1988; 19: 171–197.
  • Peter H, Deutschmann S, Muelle A, Gansewendt B, Bolt M, Hallier E. Different Affinity of erthrocyte Glutathione-S-Transferase to Methyl Chloride in humans. Arch Toxicol 1989; Suppl 13: 128–132.
  • Chasseaud L F. The nature and distribution of enzymes catalysing the conjugation of glutathione with foreign compounds. Drug Metabolism Reviews 1973; 2: 185–220.
  • Lee C W, Lewis R A, Corey E J, Barton A, Oh H, Tauber AI et al. Oxidative inactivation of leukotriene C4 by stimulated human polymorphonuclear leukocytes. Proc Natl Acad Sci USA 1982; 79: 4166–4170.
  • Cooper R A, Arner E C, Wiley J S, Shattil S J. Modification of red cell membrane structure by cholesterol-rich lipid disperions: A model for the primary spur cell defect. J Clin Invest 1975; 55: 115–126.
  • Lange Y, Cutler H B, Steck T L. The effect of cholesterol and other intercalated amphipaths on the contour and stability of the isolated red cell membrane. J Biol Chem 1980; 255: 9331–9337.
  • Saito Y, Shimada H, Imada T, Kikuchi T, Ikekawa N, Inada Y. Lysis of platelets and erythrocytes by the incorporation of a unique oxygenated sterol: 22R-hydroxycholesterol. J Membrane Biol 1985; 83: 187–191.
  • Hsu R C, Kanofski J R, Yachnin S. The formation of echinocytes by the insertion of oxygenated sterol compounds into red cell membranes. Blood 1980; 56: 109–117.
  • Kucuk O, Lis L J, Dey T, Mata R, Westerman M P, Yachnin S et al. The effects of cholesterol oxidation products in sickle and normal red blood cell membranes. Biochim Biophys Acta 1992; 1103: 296–302.
  • Rooney M W, Yachnin S, Kucuk O, Lis L J, Kauffman J W. Oxygenated cholesterols synergistically immobilize acyl chains and enhance protein helical structure in human erythrocyte membranes. Biochem Biophys Acta 1985; 820: 33–39.
  • Sugihara T, Rawicz W, Evans E A, Hebbel R P. Lipid hydroperoxides permit deformation-dependent leak of monovalent cation from erythrocytes. Blood 1991; 77: 2757–2763.
  • Vissers M C M, Carr A C, Chapman A L P. A comparison of human red cell lysis by hypochlorous and hypobromous acid: Insights into the mechanism of lysis. Biochem J 1998; in press
  • Smith L L, Johnson B H. Biological activities of oxysterols. Free Radical Biol Med 1989; 7: 285–332.
  • Christ M, Luu B, Mejia J E, Moosbrugger I, Bischoff P. Apoptosis induced by oxysterols in murine lyphoma cells and in normal thymocytes. Immunology 1993; 78: 455–460.
  • Sandstrom P A, Tebbey P W, Van Cleave S, Buttke T M. Lipid hydroperoxides induce apoptosis in T cells displaying a HIV-associated glutathione deficiency. J Biol Chem 1994; 269: 798–801.

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