Products of the reaction of HOCl with tryptophan protect LDL from atherogenic modification

Biochimie

Volumn 88, Issue 7, 2006, Pages 785-791

  Kapiotis, Stylianos ^a,b   Jirovetz, Leopold ^c   Hermann, Marcela ^d   Laggner, Hildegard ^a   Exner, Markus ^a   Esterbauer, Harald ^a   Gmeiner, Bernhard M K ^a  

^a MEDICAL UNIVERSITY OF VIENNA   (Austria)

^b Central Laboratory   (Austria)

^c UNIVERSITY OF VIENNA   (Austria)

^d MEDICAL UNIVERSITY OF VIENNA   (Austria)

Author keywords

Atherosclerosis; Carbostyril; Endothelium; Hypochlorite; Indole 3 acetaldehyde; LDL; Lipid oxidation; Tryptophan

Indexed keywords

4 METHYLCARBOSTYRIL; ALDEHYDE DERIVATIVE; APOPROTEIN; CARBOSTYRIL DERIVATIVE; COPPER; HYDROGEN PEROXIDE; HYPOCHLORITE; INDOLEACETALDEHYDE; LOW DENSITY LIPOPROTEIN; MYELOPEROXIDASE; PEROXY RADICAL; TRYPTOPHAN; UNCLASSIFIED DRUG; ACETALDEHYDE; CARBOSTYRIL; DRUG DERIVATIVE; HYPOCHLOROUS ACID; QUINOLINOL DERIVATIVE; QUINOLONE DERIVATIVE;

ANTIOXIDANT ACTIVITY; ARTICLE; ATHEROGENESIS; CHEMICAL REACTION; CONTROLLED STUDY; DECOMPOSITION; ENDOTHELIUM CELL; HUMAN; HUMAN CELL; HYPOTHESIS; LIPID OXIDATION; PROTEIN MODIFICATION; CELL CULTURE; CHEMISTRY; CYTOLOGY; DRUG EFFECT; LIPID METABOLISM; LIPID PEROXIDATION; METABOLISM; OXIDATION REDUCTION REACTION;

ACETALDEHYDE; CELLS, CULTURED; COPPER; ENDOTHELIAL CELLS; HUMANS; HYDROXYQUINOLINES; HYPOCHLOROUS ACID; LIPID METABOLISM; LIPID PEROXIDATION; LIPOPROTEINS, LDL; OXIDATION-REDUCTION; QUINOLONES; TRYPTOPHAN;

EID: 33746485101     PISSN: 03009084     EISSN: 61831638     Source Type: Journal    
DOI: 10.1016/j.biochi.2006.01.006     Document Type: Article

References (29)

1. Heinecke J.W. Mass spectrometric quantification of amino acid oxidation products in proteins: insights into pathways that promote LDL oxidation in the human artery wall. FASEB J. 13 (1999) 1113-1120
2. Steinberg D., and Lewis A. Conner memorial lecture. Oxidative modification of LDL and atherogenesis. Circulation 95 (1997) 1062-1071
3. 2-halide system in human atherosclerotic lesions: colocalization of myeloperoxidase and hypochlorite-modified proteins. Eur. J. Biochem. 267 (2000) 4495-4503
4. Hazell L.J., Arnold L., Flowers D., Waeg G., Malle E., and Stocker R. Presence of hypochlorite-modified proteins in human atherosclerotic lesions. J. Clin. Invest. 97 (1996) 1535-1544
5. Balla G., Jacob H.S., Eaton J.W., Belcher J.D., and Vercellotti G.M. Hemin: a possible physiological mediator of low density lipoprotein oxidation and endothelial injury. Arterioscler. Thromb. 11 (1991) 1700-1711
6. Grinshtein N., Bamm V.V., Tsemakhovich V.A., and Shaklai N. Mechanism of low-density lipoprotein oxidation by hemoglobin-derived iron. Biochemistry 42 (2003) 6977-6985
7. Hazell L.J., Davies M.J., and Stocker R. Secondary radicals derived from chloramines of apolipoprotein B-100 contribute to HOCl-induced lipid peroxidation of low-density lipoproteins. Biochem. J. 339 Pt. 3 (1999) 489-495
8. Jerlich A., Hammel M., Nigon F., Chapman M.J., and Schaur B.J. Kinetics of tryptophan oxidation in plasma lipoproteins by myeloperoxidase-generated HOCl. Eur. J. Biochem. 267 (2000) 4137-4143
9. 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
10. Hawkins C.L., and Davies M.J. Hypochlorite-induced damage to proteins: formation of nitrogen-centred radicals from lysine residues and their role in protein fragmentation. Biochem. J. 332 (1998) 617-625
11. Pitkanen H.T., Oja S.S., Kemppainen K., Seppa J.M., and Mero A.A. Serum amino acid concentrations in aging men and women. Amino Acids 24 (2003) 413-421
12. Exner M., Alt E., Hermann M., Hofbauer R., Kapiotis S., Quehenberger P., Speiser W., Minar E., and Gmeiner B. p-Hydroxyphenylacetaldehyde, the major product of tyrosine oxidation by the activated myeloperoxidase system can act as an antioxidant in LDL. FEBS Lett. 490 (2001) 28-31
13. Hermann M., and Gmeiner B. Altered susceptibility to in vitro oxidation of LDL in LDL complexes and LDL aggregates. Arterioscler. Thromb. 12 (1992) 1503-1506
14. Kapiotis S., Besemer J., Bevec D., Valent P., Bettelheim P., Lechner K., and Speiser W. Interleukin-4 counteracts pyrogen-induced downregulation of thrombomodulin in cultured human vascular endothelial cells. Blood 78 (1991) 410-415
15. Esterbauer H., Striegl G., Puhl H., and Rotheneder M. Continuous monitoring of in vitro oxidation of human low density lipoprotein. Free Radic. Res. Commun. 6 (1989) 67-75
16. Prinz W., and Savage N. A simple, non-enzymic synthesis of cinnabarinic acid (2-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid). Hoppe Seylers Z. Physiol. Chem. 358 (1977) 1161-1163
17. Schaur J.R., Jerlich A., and Stelmaszynska T. Hypochlorous acid as reactive oxygen species, Curr. Topics Biophysics 22 (1998) 176-185
18. Zgliczynski J.M., Stelmaszynska T., Domanski J., and Ostrowski W. Chloramines as intermediates of oxidation reaction of amino acids by myeloperoxidase. Biochim. Biophys. Acta 235 (1971) 419-424
19. Heller J.I., Crowley J.R., Hazen S.L., Salvay D.M., Wagner P., Pennathur S., and Heinecke J.W. p-Hydroxyphenylacetaldehyde, an aldehyde generated by myeloperoxidase, modifies phospholipid amino groups of low density lipoprotein in human atherosclerotic intima. J. Biol. Chem. 275 (2000) 9957-9962
20. Thomas S.R., Witting P.K., and Stocker R. 3-Hydroxyanthranilic acid is an efficient, cell-derived co-antioxidant for alpha-tocopherol, inhibiting human low density lipoprotein and plasma lipid peroxidation. J. Biol. Chem. 271 (1996) 32714-32721
21. Christen S., Thomas S.R., Garner B., and Stocker R. Inhibition by interferon-gamma of human mononuclear cell-mediated low density lipoprotein oxidation. Participation of tryptophan metabolism along the kynurenine pathway. J. Clin. Invest. 93 (1994) 2149-2158
22. Baldo-Enzi G., Baiocchi M.R., Bertazzo A., Costa C.V., and Allegri G. Tryptophan and atherosclerosis. Adv. Exp. Med. Biol. 398 (1996) 429-432
23. Simat T.J., and Steinhart H. Oxidation of free tryptophan and tryptophan residues in peptides and proteins. J. Agric. Food Chem. 46 (1998) 490-498
24. Cano A., Alcaraz O., and Arnao M.B. Free radical-scavenging activity of indolic compounds in aqueous and ethanolic media. Anal. Bioanal. Chem. 376 (2003) 33-37
25. Herraiz T., and Galisteo J. Endogenous and dietary indoles: a class of antioxidants and radical scavengers in the ABTS assay. Free Radic. Res. 38 (2004) 323-331
26. Wagner P., and Heinecke J.W. Copper ions promote peroxidation of low density lipoprotein lipid by binding to histidine residues of apolipoprotein B100, but they are reduced at other sites on LDL. Arterioscler. Thromb. Vasc. Biol. 17 (1997) 3338-3346
27. Hawkins C.L., Pattison D.I., and Davies M.J. Hypochlorite-induced oxidation of amino acids, peptides and proteins. Amino Acids 25 (2003) 259-274
28. Pattison D.I., and Davies M.J. Absolute rate constants for the reaction of hypochlorous acid with protein side chains and peptide bonds. Chem. Res. Toxicol. 14 (2001) 1453-1464
29. Drozdz R., Naskalski J.W., and Sznajd J. Oxidation of amino acids and peptides in reaction with myeloperoxidase, chloride and hydrogen peroxide. Biochim. Biophys. Acta 957 (1988) 47-52