Peroxidase-catalyzed oxidation of β-carotene in HL-60 cells and in model systems: Involvement of phenoxyl radicals

Lipids

Volumn 32, Issue 2, 1997, Pages 131-142

  Tyurin, Vladimir A ^a,d   Carta, Gianfranca ^a,c,d   Tyurina, Yulia Y ^a,d   Banni, Sebastiano ^a,c,d   Day, Billy W ^a,b,d   Corongiu, Francesco P ^c,d   Kagan, Valerian E ^a,b,d  

^a UNIVERSITY OF PITTSBURGH   (United States)

^b UNIVERSITY OF PITTSBURGH CANCER INSTITUTE   (United States)

^c UNIVERSITY OF CAGLIARI   (Italy)

^d SECHENOV INSTITUTE OF EVOLUTIONARY PHYSIOLOGY AND BIOCHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

6 HYDROXY 2,2,5,7,8 PENTAMETHYLCHROMAN; ANTIOXIDANT; BETA CAROTENE; CAROTENOID; HORSERADISH PEROXIDASE; HYDROGEN PEROXIDE; HYDROXYL RADICAL; MYELOPEROXIDASE; PEROXIDASE; PHENOL DERIVATIVE;

ANTIOXIDANT ACTIVITY; ARTICLE; CELL STRAIN HL 60; CONTROLLED STUDY; FATTY ACID OXIDATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; LIPID PEROXIDATION; MICELLE; OXIDATIVE STRESS; REACTION ANALYSIS; SPECTROPHOTOMETRY;

BETA CAROTENE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMONES; ELECTRON SPIN RESONANCE SPECTROSCOPY; HL-60 CELLS; HUMANS; HYDROGEN PEROXIDE; MASS SPECTROMETRY; OXIDATION-REDUCTION; PHENOL; PHENOLS;

EID: 0031042871     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11745-997-0017-0     Document Type: Article

References (57)

1. Barclay, L.R.C., Locke, S.J., MacNeil, J.M., Van Kessel, J., Burton, G.W., and Ingold, K.U. (1984) Autoxidation of "Micelles" and Model Membranes: Quantitative Kinetic Measurements Can Be Made by Using Either Water-Soluble or Lipid-Soluble Initiators with Water-Soluble or Lipid-Soluble Chain-Breaking Antioxidants, J. Am. Chem. Soc. 106, 2479-2481.
2. Yamamoto, Y., Haga, S., Niki, E., and Kamiya, Y. (1984) Oxidation of Lipids. V. Oxidation of Methyl Linoleate in Aqueous Dispersions, Bull. Chem. Soc. Jpn. 57, 1260-1264.
3. Mukai, K., Kageyama, Y., Ishida, T., and Fukuda, K. (1989) Synthesis and Kinetic Study of Antioxidant Activity of New Tocopherol (vitamin E) Compounds, J. Org. Chem. 54, 552-556.
4. Pryor, W.A., Cornicelli, J.A., Devall, L.J., Tait, B., Trivedi, D.T., Witiak, D.T., and Wu, M. (1993) A Rapid Screening Test to Determine the Antioxidant Potencies of Natural and Synthetic Antioxidants, J. Org. Chem. 58, 3521-3532.
5. Eastmond, D.A., Smith, M.T., Ruzo, L.O., and Ross, D. (1986) Metabolic Activation of Phenol by Human Myeloperoxidase and Horseradish Peroxidase, Mol. Pharmacol. 30, 674-679.
6. Schreiber, J., Foureman, G.L., Hughes, M.F., Mason, R.P., and Eling, T.E. (1989) Detection of Glutathione Thiyl Free Radical Catalyzed by Prostaglandin H Synthase Present in Keratinocytes. Study of Co-Oxidation in a Cellular System, J. Biol. Chem. 264, 7936-7943.
7. Eisenstein, O., Giessner-Prettre, C., Maddaluno, J., Stussi, D., and Weber, J. (1992) Theoretical Study of Oxyhemocyanin Activesite: A Possible Insight on the First Step of Phenol Oxidation by Tyrosinase, Arch. Biochem. Biophys. 296, 247-255.
8. Stoyanovsky, D.A., Goldman, R., Claycamp, H.G., and Kagan, V.E. (1995) Phenoxyl Radical-Induced Thiol-Dependent Generation of Reactive Oxygen Species: Implications for Benzene Toxicity, Arch. Biochem. Biophys. 317, 315-323.
9. Mao, S.S., Holler, T.P., Yu, G.X., Bollinger, J.M. Jr., Booker, S., Johnston, M.I., and Stubbe, J. (1992) A Model for the Role of Multiple Cysteine Residues Involved in Ribonucleotide Reduction: Amazing and Still Confusing, Biochemistry 31, 9733-9743.
10. Ormo, M., Regnstrom, K., Wang, Z., Que, L. Jr., Sahlin, M., and Sjoberg, B.M. (1995) Residues Important for Radical Stability in Ribonucleotide Reductase from Escherichia coli, J. Biol. Chem. 270, 6570-6576.
11. Foti, M., Ingold, K.U., and Lusztyk, J. (1994) The Surprisingly High Reactivity of Phenoxyl Radicals, J. Am. Chem. Soc. 116, 9440-9447.
12. Goldman, R., Stoyanovsky, D.A., Day, B.W., and Kagan, V.E. (1995) Reduction of Phenoxyl Radicals by Thioredoxin Results in Selective Oxidation of its SH-Groups to Disulfides. An Antioxidant Function of Thioredoxin, Biochemistry 34, 4765-1772.
13. Tyurina, Y.Y., Tyurin, V.A., Yalowich, J.C., Quinn, P.J., Claycamp, H.G., Schor, N.F., Pitt, B.R., and Kagan, V.E. (1995) Phenoxyl Radicals of Etoposide (VP-16) Can Directly Oxidize Intracellular Thiols: Protective Versus Damaging Effects of Phenolic Antioxidants, Toxicol. Appl. Pharmacol. 131, 277-288.
14. 2, Pharmacology 49, 325-335.
15. Kalyanaraman, B., Darleyusmar, V., Struck, A., Hogg, N., and Parthasarathy, S. (1995) Role of Apolipoprotein B-Derived Radical and Alpha-Tocopheroxyl Radical in Peroxidase-Dependent Oxidation of Low Density Lipoprotein, J. Lipid Res. 36, 1037-1045.
16. Miller, Y.I., Felikman, Y., and Shaklai, N. (1996) Hemoglobin-Induced Apolipoprotein-B Cross-Linking in Low Density Lipoprotein Peroxidation, Arch. Biochem. Biophys. 326, 252-260.
17. Santanam, N., and Parthasarathy, S. (1995) Paradoxical Actions of Antioxidants in the Oxidation of Low Density Lipoprotein by Peroxidases, J. Clin. Inv. 95, 2594-2600.
18. Palozza, P., and Krinsky, N.I. (1992) β-Carotene and α-Tocopherol are Synergistic Antioxidants, Arch. Biochem. Biophys. 297, 184-187.
19. Palozza, P., and Krinsky, N.I. (1992) Astaxanthin and Canthaxanthin Are Potent Antioxidants in a Membrane Model, Arch. Biochem. Biophys. 297, 291-295.
20. Palozza, P., and Krinsky, N.I. (1992) Antioxidants Effects of Carotenoids in vivo and in vitro: An Overview, Meth. Enzymol. 213, 163-170.
21. Palozza, P., Luberto, C., and Bartoli, G.M. (1995) The Effect of Fatty Acid Unsaturation on the Antioxidant Activity of β-Carotene and α-Tocopherol in Hexane Solutions, Free Radical Biol. Med. 18, 943-948.
22. Tsuchihashi, H., Kigoshi, M., Iwatsuki, M., and Niki, E. (1995) Action of β-Carotene as an Antioxidant Against Lipid Peroxidation, Arch. Biochem. Biophys. 323, 137-147.
23. Handelman, G.J. (1996) Carotenoids as Scavengers of Active Oxygen Species, in Handbook of Antioxidants (Cadenas E., and Packer L., eds.) pp. 259-314, Marcel Dekker, New York.
24. Palozza, P., Calviello, G., and Bartoli, G.M. (1995) Prooxidant Activity of β-Carotene Under 100% Oxygen Pressure in Rat Liver Microsomes, Free Radical Biol. Med. 19, 887-892.
25. Burton, G.W., and Ingold, K.U. (1984) β-Carotene, An Unusual Type of Lipid Antioxidant, Science 224, 569-573.
26. Burton, G.W. (1989) Antioxidant Action of Carotenoids, J. Nutr. 119, 109-111.
27. Palozza, P., Luberto, C., Ricci, P., Sgarlata, E., Caviello, G., and Bartoli, G.M. (1996) Effect of β-Carotene and Canthaxanthin on tert-Butyl Hydroperoxide-Induced Lipid Peroxidation in Murine Normal and Tumor Thymocytes, Arch. Biochem. Biophys. 325, 145-151.
28. Nonaka, T., Mio, M., Doi, M., and Tasaka, K. (1992) Histamine-Induced Differentiation of HL-60 cells. The Role cAMP and Protein Kinase A, Biochem. Pharmacol. 44, 1115-1691.
29. Lang, J.K., Cohil, K., and Packer, L. (1986) Simultaneous Determination of Tocopherols, Ubiquinols, and Ubiquinones in Blood, Plasma, Tissue Homogenates and Subcellular Fraction, Anal. Biochem. 157, 106-116.
30. Moore, K.L. Moronne, M.M., and Mehlhorn, R.J. (1992) Electron Spin Resonance Study of Peroxidase Activity and Kinetics, Arch. Biochem. Biophys. 299, 47-56.
31. Liebler, D. C., and McClure, T. D. (1996) Antioxidant Reactions of β-Carotene - Identification of Carotenoid-Radical Adducts, Chem. Res. Toxicol. 9, 8-11.
32. Partridge, R.S., Monroe, S.M., Parks, J.K., Johnson, K., Parker, Jr., W.D., Eaton, G.R., and Eaton, S.S. (1994) Spin Trapping of Azidyl and Hydroxyl Radicals in Azide-Inhibited Rat Brain Submitochondrial Particles, Arch. Biochem. Biophys. 310, 210-217.
33. Omelka, L., and Kovacova, J. (1994) Spin-Trapping of Sterically Unhindered Phenoxyl Radicals with Nitrosobenzene and Nitrosodurene, Magnet. Reson. Chem. 32, 525-531.
34. Packer, J.E., Slater, T.F., and Wilson, R.L. (1979) Direct Observation of a Free Radical Interaction Between Vitamin E and Vitamin C, Nature 278, 737-738.
35. Kagan, V.E., Serbinova, E.A., and Packer, L. (1990) Recycling and Antioxidant Activity of Tocopherol Homologues of Differing Hydrocarbon Chainlength in Liver Microsomes, Arch. Biochem. Biophys. 282, 221-225.
36. Kagan, V.E. (1988) Lipid Peroxidation in Biomembranes, pp. 1-184, CRC Press, Boca Raton.
37. Kagan, V.E., Freileben, H.J., Tsuchiya, M., Forte, T., and Packer, L. (1991) Generation of Probucol Radicals and Their Reduction by Ascorbate and Dihidrolipoic Acid in Human Low Density Lipoproteins, Free Radical Res. Commun. 15, 2403-2413.
38. Kagan, V.E., Yalowich, J.C., Day, B.W., Goldman, R.R., and Stoyanovsky, D.A. (1994) Ascorbate Is the Primary Reductant of the Phenoxyl Radical of Etoposide (VP-16) in the Presence of Thiols Both in Cell Homogenates and in Model Systems, Biochemistry 33, 9651-9660.
39. Packer, L., and Kagan, V.E. (1993) Vitamin E: The Antioxidant Harvesting Center of Membranes and Lipoproteins, in Vitamin E: Biochemistry and Clinical Applications (Packer, L., and Fuchs, J., eds.) pp. 179-192, Marcel Dekker, New York.
40. Sies, H., Stahl, W., and Sundquist, A.R. (1992) Vitamins E and C, β-Carotene, and Other Carotenoids, Ann. N.Y. Acad. Sci. 669, 7-20.
41. The α-Tocopherol, β-Carotene Cancer Prevention Study Group (1994) The Effect of Vitamin E and β-Carotene on the Incidence of Lung Cancer and Other Cancers in Male Smokers, New Engl. J. Med. 330, 1029-1035.
42. Britton, G. (1995) Structure and Properties of Carotenoids in Relation to Function, FASEB J. 9, 1551-1558.
43. Weitberg, A.B., Weizman, S.A., Clark, E.P., and Stossel, T.P. (1985) Effects of Antioxidants on Oxidant-Induced Sister Chromatid Exchange Formation, J. Clin. Invest. 75, 1835-1841.
44. Rousseau, E.J., Davison, A.J., and Dunn, B. (1992) Protection by β-Carotene and Related Compounds Against Oxygen-Mediated Cytotoxicity and Genotoxicity: Implications for Carcinogenesis and Anticarcinogenesis, Free Radical Biol. Med. 13, 407-433.
45. Esterbauer, H., Puhl, H., Dieber-Rotheneder, M., Waeg, G., and Rabl, H. (1991) Effect of Antioxidants on Oxidative Modification of LDL, Ann. Med. 23, 573-581.
46. Suarna, C., Hood, R.L., Dean, R.T., and Stocker, R. (1993) Comparative Antioxidant Activity of Tocotrienols and Other Natural Lipid-Soluble Antioxidants in a Homogenous System, and in Rat and Human Lipoproteins, Biochim. Biophys. Acta 1166, 163-170.
47. Dowry, V.W., Ingold, K.V., and Stocker, R. (1992) Vitamin E in Human Low Density Lipoprotein: When and How This Antioxidant Becomes a Prooxidant, Biochem. J. 288, 341-344.
48. Kettle, A.J., Gedye, C.A., Hampton, M.B., and Winterbourn, C.C. (1995) Inhibition of Myeloperoxidase by Benzoic Acid Hydrazides, Biochem. J. 308, 559-563.
49. Kanner, J., and Kinsella, J.E. (1983) Lipid Deterioration Initiated by Phagocytic Cells in Muscle Foods: β-Carotene Destruction by a Myeloperoxidase-Hydrogen Peroxide-Halide System, J. Agric. Food Chem. 31, 370-376.
50. Steinbeck, M.J., Khan, A.U., and Karnovsky, M.J. (1992) Intracellular Singlet Oxygen Generation by Phagocytosing Neutrophils in Response to Particles Coated with a Chemical Trap, J. Biol. Chem. 267, 13425-13433.
51. Heinecke, J.W., Li, W., Mueller, D.M., Bohrer, A., and 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.
52. Heinecke, J.W., Li, W., Daehnke, 3rd, H.L., and 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.
53. Stoyanovsky, D.A., Goldman, R., Jonnalagadda, S.S., Day, B.W., Claycamp, H.G., and Kagan, V.E. (1996) Detection and Characterization of the Electron Paramagnetic Resonance-Silent Glutathionyl-5,5-Dimethyl-1-Pyrroline N-Oxide Adduct Derived from Redox Cycling of Phenoxyl Radicals in Model Systems and HL-60 Cells, Arch. Biochem. Biophys. 330, 3-11.
54. Subrahmanyam, V.V., Ross, D., Eastmond, D.A., and Smith, M.T. (1991) Potential Role of Free Radicals in Benzene-Induced Myelotoxicity and Leukemia, Free Radical Biol. Med. 1, 495-515.
55. Snyder, R., Witz, G., and Goldstein, B.D. (1993) The Toxicology of Benzene, Environ. Health Persp. 100, 293-306.
56. Niki, E. (1990) Free Radical Initiators as Source of Water- and Lipid-Soluble Peroxyl Radicals, Meth. Enzymol. 186, 100-108.
57. Qin, Y., and Wheeler, R.A. (1995) Tyrosine Phenoxyl Radical Structures, Vibrational Frequencies, and Spin-Densities, J. Am. Chem. Soc. 117, 6083-6092.