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

Acta Biochimica Polonica

Volumn 47, Issue 4, 2000, Pages 889-899

  Spickett, Corinne M ^a   Jerlich, Andreas ^b   Panasenko, Oleg M ^c   Arnhold, Juergen ^d   Pitt, Andrew R ^a   Stelmaszyńska, Teresa ^e   Schaur, R Joerg ^b  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b UNIVERSITY OF GRAZ   (Austria)

^c FEDERAL RESEARCH AND CLINICAL CENTER OF PHYSICAL CHEMICAL MEDICINE OF FEDERAL MEDICAL BIOLOGICAL AGENCY   (Russian Federation)

^d UNIVERSITY OF LEIPZIG   (Germany)

^e JAGIELLONIAN UNIVERSITY   (Poland)

Author keywords

Hypochlorous acid; Lipid chlorohydrins; Lipid peroxidation; Lipids; Low density lipoprotein; Unsaturated fatty acids

Indexed keywords

CHOLESTEROL; FREE RADICAL; HYPOCHLOROUS ACID; OXYGEN; PEROXIDASE; REACTIVE OXYGEN METABOLITE;

ANIMAL; CHEMICAL MODEL; DOSE RESPONSE; HUMAN; LIPID METABOLISM; METABOLISM; PHAGOCYTOSIS; REVIEW; TIME;

ANIMALS; CHOLESTEROL; DOSE-RESPONSE RELATIONSHIP, DRUG; FREE RADICALS; HUMANS; HYPOCHLOROUS ACID; LIPID METABOLISM; MODELS, CHEMICAL; OXYGEN; PEROXIDASE; PHAGOCYTOSIS; REACTIVE OXYGEN SPECIES; TIME FACTORS;

EID: 0034584946     PISSN: 0001527X     EISSN: None     Source Type: Journal    
DOI: 10.18388/abp.2000_3944     Document Type: Review

References (49)

1. Stossel, T.P., Mason, R.J. & Smith, A.L. (1974) Lipid peroxidation by human blood phagocytes. J. Clin. Invest. 54, 638-645.
2. Claster, S., Chiu, D.T., Quintanilha, A. & Lubin, B. (1984) Neutrophils mediate lipid peroxidation in human red cells. Blood 64, 1079-1084.
3. Carlin, G. & Djursaeter, R. (1988) Peroxidation of phospholipids promoted by myeloperoxidase. Free Radical Res. Commun. 4, 251-257.
4. Thomas, M.J., Shirley, P.S., Hedrick, C.C. & DeChatelet, L.R. (1986) Role of free radical processes in stimulated human polymorphonuclear leukocytes. Biochemistry 25, 8042-8048.
5. Cathcart, M.K., Morel, D.W. & Chisolm, G.M. 3d (1985) Monocytes and neutrophils oxidize low density lipoprotein making it cytotoxic. J. Leukoc. Biol. 38, 341-350.
6. Wieland, E., Brandes, A., Armstrong, V.W. & Oellerich, M. (1993) Oxidative modification of low density lipoproteins by human polymorphonuclear leukocytes. Eur. J. Clin. Chem. Clin. Biochem. 31, 725-731.
7. Schaur, R.J., Dussing, G., Kink, E., Schauenstein, E., Posch, W., Kukovetz, E. & Egger, G. (1994) The lipid peroxidation product 4-hydroxynonenal is formed by - and is able to attract - rat neutrophils in vivo. Free Radical Res. 20, 365-373.
8. Daugherty, A., Rateri, D.L., Dunn, J.L. & Heinecke, J.W. (1994) Myeloperoxidase, a catalyst for lipoprotein oxidation, is expressed in human atherosclerotic lesions. J. Clin. Invest. 94, 437-444.
9. Heinecke, J.W. (1997) Mechanism of oxidative damage of low density lipoprotein in human atherosclerosis. Curr. Opin. Lipidol. 8, 268-274.
10. Hazell, L.J., Arnold, L., Flowers, D., Waeg, G., Malle, E. & Stocker, R. (1996) Presence of hypochlorite-modified proteins in human atherosclerotic lesions. J. Clin. Invest. 97, 1535-1544.
11. Harrison, J.E. & Schultz, J. (1976) Studies on the chlorinating activity of myeloperoxidase. J. Biol. Chem. 251, 1371-1374.
12. Jerlich, A., Fabjan, J.S., Tschabuschnig, S., Smirnova, A.V., Horakova, L., Hayn, M., Auer, H., Guttenberger, H., Leis, H.-J., Tatzber, F., Waeg, G. & Schaur, R.J. (1998) Human low density lipoprotein as a target of hypochlorite generated by myeloperoxidase. Free Radical Biol. Med. 24, 1139-1148.
13. Arnhold, J., Wiegel, D., Richter, O., Hammerschmidt, S., Arnold, K. & Krumbiegel, M. (1991) Modification of low density lipoproteins by sodium hypochlorite. Biomed. Biochim. Acta 50, 967-973.
14. Hazell, L.J. & Stocker, R. (1993) Oxidation of low-density lipoprotein with hypochlorite causes transformation of the lipoprotein into a high-uptake form for macrophages. Biochem. J. 290, 165-172.
15. Witztum, J.L. & Steinberg, D. (1991) Role of oxidized low density lipoprotein in atherogenesis. J. Clin. Invest. 88, 1785-1792.
16. Berliner, J.A. & Heinecke, J.W. (1996) The role of oxidized lipoproteins in atherogenesis. Free Radical Biol. Med. 20, 707-727.
17. van den Berg, J.J. & Winterbourn, C.C. (1994) Measurement of reaction products from hypochlorous acid and unsaturated lipids. Methods Enzymol. 233, 639-649.
18. Hazen, S.L., Hsu, F.F., Gaut, J.P., Crowley, J.R. & Heinecke, J.W. (1999) Modification of proteins and lipids by myeloperoxidase. Methods Enzymol. 300B, 88-105.
19. Stelmaszynska, T., Kukovetz, E., Egger, G. & Schaur, R.J. (1992) Possible involvement of myeloperoxidase in lipid peroxidation. Int. J. Biochem. 24, 121-128.
20. Panasenko, O.M. (1997) The mechanism of the hypochlorite-induced lipid peroxidation. Biofactors 6, 181-190.
21. -. Free Radical Biol. Med. 16, 143-148.
22. Panasenko, M.O., Evgina, S.A., Driomina, E.S., Sharov, V.S., Sergienko, V.I. & Vladimirov, Y.A. (1995) Hypochlorite induces lipid peroxidation in blood lipoproteins and phospholipid liposomes. Free Radical Biol. Med. 19, 133-140.
23. Panasenko, O.M., Arnhold, J., Schiller, J., Arnhold, K. & Sergienko, V.I. (1994) Peroxidation of egg yolk phosphatidylcholine liposomes by hypochlorous acid. Biochim. Biophys. Acta 1215, 259-266.
24. Panasenko, O.M. & Arnhold, J. (1996) Mechanisms of hypochlorite-induced peroxidation on phospholipid liposomes. Membr. Cell Biol. 10, 93-104.
25. Panasenko, O.M., Arnhold, J. & Sergienko, V.I. (1998) The effect of pH on hypochlorite-induced peroxidation of phospholipid liposomes. Biofizika 43, 463-469.
26. Jerlich, A., Fritz, G., Kharrazi, H., Hammel, M., Tschabuschnig, S., Glatter, O. & Schaur, R.J. (2000) Comparison of HOCl traps with myeloperoxidase inhibitors in prevention of low density lipoprotein oxidation. Biochim. Biophys. Acta 1481, 109-118.
27. Hazell, J.L., van den Berg, J.J. & Stocker, R. (1994) Oxidation of low density lipoprotein by hypochlorite causes aggregation that is mediated by modification of lysine residues rather than lipid oxidation. Biochem. J. 302, 297-304.
28. Hazell, L.J., Davies, M.J. & Stocker, R. (1999) Secondary radicals derived from chloramines of apolipoprotein B-100 contribute to HOCl-induced lipid-peroxidation of low density lipoprotein. Biochem. J. 339, 489-495.
29. Winterbourn, C.C., van den Berg, J.J., Roitman, E. & Kuypers, F.A. (1992) Chlorohydrin formation from unsaturated fatty acids reacted with hypochlorous acid. Arch. Biochem. Biophys. 296, 547-555.
30. Heinecke, J.W., Li, W., Mueller, D.M., Bohrer, A. & Turk, J. (1994) Cholesterol chlorohydrin synthesis by the myeloperoxidase-hydrogen peroxide-chloride system: Potential markers for lipoproteins oxidatively damaged by phagocytes. Biochemistry 33, 10127-10136.
31. Arnhold, J., Panasenko, O.M., Schiller, J., Vladimirov, Y.A. & Arnold, K. (1995) The action of hypochlorous acid on phosphatidylcholine liposomes in dependence on the content of double bonds. Stoichiometry and NMR analysis. Chem. Phys. Lipids 78, 55-64.
32. van den Berg, J.J., Winterbourn, C.C. & Kuypers, F.A. (1993) Hypochlorous acid-mediated modification of cholesterol and phospholipid: Analysis of reaction products by gas chromatography-mass spectrometry. J. Lipid Res. 34, 2005-2012.
33. Carr, A.C., van den Berg, J.J. & Winterbourn, C.C. (1996) Chlorination of cholesterol in cell membranes by hypochlorous acid. Arch. Biochem. Biophys. 332, 63-69.
34. Carr, A.C., Winterbourn, C.C., Blunt, J.W., Phillips, A.J. & Abell, A.D. (1997) Nuclear magnetic resonance characterization of 6 α-chloro-5 β-cholestane-3 β,5 diol formed from the reaction of hypochlorous acid with cholesterol. Lipids 32, 363-367.
35. Hazen, S.L., Hsu, F.F., Duffin, K. & Heinecke, J.W. (1996) 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. 271, 23080-23088.
36. Jerlich, A., Pitt, A.R., Schaur, R.J. & Spickett, C.M. (2000) Pathways of phospholipid oxidation by HOCl in human LDL detected by LC-MS. Free Radical Biol. Med. 28, 673-682.
37. Panasenko, O.M. & Arnhold, J. (1999) Linoleic acid hydroperoxide favours hypochlorite- and myeloperoxidase-induced lipid peroxidation. Free Radical Res. 30, 479-487.
38. 1H NMR spectroscopy and chemiluminescence analyses. Z. Naturforsch. 51c, 386-394.
39. Panasenko, O.M., Arnhold, J. & Schiller, J. (1997) Hypochlorite reacts with an organic hydroperoxide forming free radicals, but not singlet oxygen, and thus initiates lipid peroxidation. Biochemistry (Moscow) 62, 951-959.
40. Savenkova, M.I., Mueller, D.M. & Heinecke, J.W. (1994) Tyrosyl radical generated by myeloperoxidase is a physiological catalyst for the initiation of lipid peroxidation in low density lipoprotein. J. Biol. Chem. 269, 20394-20400.
41. Heinecke, J.W., Li, W., Daehnke, H.L. & Goldstein, J.A. (1993) Dityrosine, a specific marker of oxidation, is synthesized by the myeloperoxidase-hydrogen peroxide system of human neutrophils and macrophages. J. Biol. Chem. 268, 4069-4077.
42. Heinecke, J.W., Li, W., Francis, G.A. & Goldstein, J.A. (1993) Tyrosyl radical generated by myeloperoxidase catalyzes the oxidative cross-linking of proteins. J. Clin. Invest. 91, 2866-2872.
43. Hawkins, C.L. & Davies, M.J. (1998) Hypochlorite-induced oxidation of plasma proteins: Formation of nitrogen-centred radicals and their role in protein fragmentation. Curr. Top. Biophys. 22, 89-98.
44. Momynaliev, K.T., Osipova, S.V., Sadovskaya, V.L., Govorun, V.M. & Sergienko, V.I. (1997) Products of the reaction of cholesterol with hypochlorite anion. Biochemistry (Moscow) 62, 158-164.
45. Carr, A.C., van den Berg, J.J. & Winterbourn, C.C. (1998) Differential reactivities of hypochlorous and hypobromous acids with purified Escherichia coli phospholipid - formation of haloamines and halohydrins. Biochim. Biophys. Acta 1392, 254-264.
46. Vissers, M.C., Stern, A., Kuypers, F., van den Berg, J.J. & Winterbourn, C.C. (1994). Membrane changes associated with lysis of red blood cells by hypochlorous acid. Free Radical Biol. Med. 16, 703-712.
47. Vissers, M.C.M., Carr, A.C. & Chapman, A.L.P. (1998) Comparison of human red-cell lysis by hypochlorous and hypobromous acids - insights into the mechanisms of lysis. Biochem. J. 330, 131-138.
48. Carr, A.C., Vissers, M.C., Domigan, N.M. & Winterbourn, C.C. (1997) Modification of red cell membrane lipids by hypochlorous acid and haemolysis by preformed lipid chlorohydrins. Redox Rep. 3, 263-271.
49. Drobnies, A.E., Venczel, A.E. & Cornell, R.B. (1998) Activation of CTP-phosphocholine cytidyltransferase by hypochlorite-oxidized phosphatidylcholines. Biochim. Biophys. Acta 1393, 90-98.