Evaluation of products upon the reaction of hypohalous acid with unsaturated phosphatidylcholines

Chemistry and Physics of Lipids

Volumn 129, Issue 1, 2004, Pages 85-96

  Spalteholz, Holger ^a   Wenske, Kathrin ^a   Panasenko, Oleg M ^b   Schiller, Jürgen ^a   Arnhold, Jürgen ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

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

Author keywords

Halogenohydrins; Hypobromous acid; Hypochlorous acid; MALDI TOF mass spectrometry; Myeloperoxidase; Phosphatidylcholine

Indexed keywords

ALPHA CHLOROHYDRIN; BROMINE DERIVATIVE; CHLORINE DERIVATIVE; HALOGEN; HYPOCHLOROUS ACID; ISOTOPE; OXYGEN; OXYGEN 18; PHOSPHATIDYLCHOLINE;

ARTICLE; CHEMICAL BOND; COMPLEX FORMATION; EVALUATION; LIPID ANALYSIS; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MOLECULAR INTERACTION; MOLECULAR STABILITY; PRIORITY JOURNAL; REACTION ANALYSIS;

BROMATES; BROMINE; CHLORINE; GLYCOLS; HYDROGEN PEROXIDE; HYPOCHLOROUS ACID; ISOTOPE LABELING; ISOTOPES; OXYGEN ISOTOPES; PEROXIDASE; PHOSPHATIDYLCHOLINES; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 1442348379     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2003.12.005     Document Type: Article

References (26)

1. Arlandson M., Decker T., Roongta V.A., Bonilla L., Mayo K.H., MacPherson J.C., Hazen S.L., Slungaard A. Eosinophil peroxidase oxidation of thiocyanate. J. Biol. Chem. 276:2001;215-224.
2. Arnhold J., Mueller S., Arnold K., Sonntag K. Mechanisms of inhibition of chemiluminescence in the oxidation of luminol by sodium hypochlorite. J. Biolumin. Chemilumin. 8:1993;307-313.
3. Arnhold J., Osipov A.N., Spalteholz H., Panasenko O.M., Schiller J. Effects of hypochlorous acid on unsaturated phosphatidylcholines. Free Radic. Biol. Med. 31:2001;1111-1119.
4. Arnhold J., Osipov A.N., Spalteholz H., Panasenko O.M., Schiller J. Formation of lysophospholipids from unsaturated phosphatidylcholines under the influence of hypochlorous acid. Biochim. Biophys. Acta. 1572:2002;91-100.
5. Arnhold J., Panasenko O.M., Schiller J., Vladimirov J.A., Arnold K. The action of hypochlorous acid on phosphatidylcholine liposomes in dependence on the content of double bonds. Stoichiometry and NMR analysis. Chem. Phys. Lipids. 78:1995;55-64.
6. Baldus S., Eiserich J.P., Mani A., Castrom L., Figueroa M., Chumley P., Ma W., Tousson A., White R., Bullard D.C., Brennan M.-L., Lusis A.J., Moore K.P., Freeman B.A. Endothelial transcytosis of myeloperoxidase confers specificity to vascular ECM proteins as targets to tyrosine nitration. J. Clin. Invest. 108:2001;1759-1770.
7. Bamberger E., Lodter W. Studium über alicyclische Naphthalinderivate. Liebigs Ann. Chem. Pharm. 288:1895;74-133.
8. van den Berg J.J.M., Winterbourn C.C., Kuypers F.A. Hypochlorous acid-mediated modification of cholesterol and phospholipid: analysis of reaction products by gas chromatography-mass spectrometry. J. Lipid Res. 34:1993;2005-2012.
9. Carr A.C., Winterbourn C.C., van den Berg J.J.M. Peroxidase-mediated bromination of unsaturated fatty acids to form bromohydrins. Arch. Biochem. Biophys. 327:1996;227-233.
10. Cech P., Lehrer R.I. Phagolysosomal pH of human neutrophils. Blood. 63:1984;88-95.
11. Cheek C.H., Linnenbom V.J. The radiation chemistry of alkaline hypobromite solutions. J. Phys. Chem. 67:1963;1856-1860.
12. Daphna E.M., Michaela S., Eynat P., Irit A., Rimon S. Association of myeloperoxidase with heparin: oxidative inactivation of proteins on the surface of endothelial cells by the bound enzyme. Mol. Cell. Biochem. 183:1998;55-61.
13. Evans W.P. Über die Abspaltungsgeschwindigkeiten von Chlorwasserstoff aus Chlorhydrinen und ihre Beziehung zur stereochemischen Konstitution. Z. Phys. Chem. 7:1891;337-357.
14. Klebanoff, S.J., 1992. Myeloperoxidase: occurrence and biological function. In: Everse, J., Everse, K., Grisham, M.B. (Eds.), Peroxidases in Chemistry and Biology. CRC Press, Boca Raton, pp. 1-35.
15. Morris J.C. The acid ionization constant of HOCl from 5 to 35°J. Phys. Chem. 70:1966;3798-3805.
16. Panasenko O.M., Arnhold J., Vladimirov Y.A., Arnold K., Sergienko V.I. Hypochlorous acid-induced peroxidation of egg yolk phosphatidylcholine is mediated by hydroperoxides. Free Radic. Res. 27:1997;1-12.
17. Panasenko O.M., Arnhold J. Linoleic acid hydroperoxide favours hypochlorite- and myeloperoxidase-induced lipid peroxidation. Free Radic. Res. 30:1999;479-487.
18. Panasenko O.M., Spalteholz H., Schiller J., Arnhold J. Myeloperoxidase-induced formation of chlorohydrins and lysophospholipids from unsaturated phosphatidylcholines. Free Radic. Biol. Med. 34:2003;553-562.
19. Petrenko-Kritschenko P., Konschin A. Ueber die Leichtigkeit der Bildung ringförmiger Verbindungen. Liebigs Ann. Chem. Pharm. 342:1905;51-59.
20. Prütz W. Hypochlorous acid interactions with thiols, nucleotides, DNA, and other biological substrates. Arch. Biochem. Biophys. 332:1996;110-120.
21. Schaur R.J., Jerlich A., Stelmaszynska T. Hypochlorous acid as reactive oxygen species. Curr. Top. Biophys. 22:1998;176-185.
22. Schiller J., Arnhold J., Gründer W., Arnold K. The action of hypochlorous acid on polymeric components of cartilage. Biol. Chem. Hoppe-Seyler. 375:1994;167-172.
23. Schiller J., Arnhold J., Benard S., Müller M., Reichl S., Arnold K. Lipid analysis by matrix-assisted-laser-desorption and ionization mass spectrometry: a methodological approach. Anal. Biochem. 267:1999;45-56.
24. Segal A.W., Geisow M., Garcia R., Harper A., Miller R. The respiratory burst of phagocytic cells is associated with a rise in vacuolar pH. Nature. 290:1981;406-409.
25. Winterbourn C.C. Comparative reactivities of various biological compounds with myeloperoxidase-hydrogen peroxide-chloride, and similarity of the oxidant to hypochlorite. Biochim. Biophys. Acta. 840:1985;204-210.
26. 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. 296:1992;547-555.