Trypanosama cruzi dihydrolipoamide dehydrogenase as target for phenothiazine cationic radicals. Effect of antioxidants

Current Drug Targets

Volumn 7, Issue 9, 2006, Pages 1155-1179

  Gutiérrez Correa, José ^a  

^a Universidad Nacional Mayor de San Marcos   (Peru)

Author keywords

Cation Radical Decay; Horseradish Peroxidase (HRP); Myeloperoxidase (MPO); Myoglobin (Mb); Peroxidase; Phenothiazines (PTZ)

Indexed keywords

ALIMEMAZINE; ANTIOXIDANT; ANTITRYPANOSOMAL AGENT; ASCORBIC ACID; BENZNIDAZOLE; DIHYDROLIPOAMIDE DEHYDROGENASE; ENZYME INHIBITOR; FLUPHENAZINE; FREE RADICAL; HOMOFENAZINE; HORSERADISH PEROXIDASE; HYDROGEN PEROXIDE; MYELOPEROXIDASE; MYOGLOBIN; NIFURTIMOX; PERICIAZINE; PEROXIDASE; PHENOL DERIVATIVE; PHENOTHIAZINE; PROMAZINE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; THIOL DERIVATIVE; THIORIDAZINE; TRIFLUOPERAZINE; TRIFLUPROMAZINE; TROLOX C; TRYPANOTHIONE REDUCTASE; TRYPTOPHAN; TYROSINE; UNINDEXED DRUG; MONOVALENT CATION; PHENOTHIAZINE DERIVATIVE; SCAVENGER;

CATALYSIS; CHAGAS DISEASE; DRUG BINDING; DRUG MECHANISM; DRUG OXIDATION; DRUG STRUCTURE; DRUG TARGETING; ELECTRON; ENZYME INACTIVATION; HEART; HUMAN; INCUBATION TIME; MACROMOLECULE; MAMMAL; NONHUMAN; REVIEW; SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; TRYPANOSOMA CRUZI; UNSPECIFIED SIDE EFFECT; AMINO ACID SEQUENCE; ANIMAL; CHEMISTRY; DRUG ANTAGONISM; DRUG DELIVERY SYSTEM; DRUG EFFECT; ENZYMOLOGY; GENETICS; METABOLISM; METHODOLOGY; MOLECULAR GENETICS;

AMINO ACID SEQUENCE; ANIMALS; ANTIOXIDANTS; CATIONS, MONOVALENT; DIHYDROLIPOAMIDE DEHYDROGENASE; DRUG DELIVERY SYSTEMS; ENZYME INHIBITORS; FREE RADICAL SCAVENGERS; HUMANS; MOLECULAR SEQUENCE DATA; PHENOTHIAZINES; TRYPANOSOMA CRUZI;

EID: 33748506876     PISSN: 13894501     EISSN: None     Source Type: Journal    
DOI: 10.2174/138945006778226615     Document Type: Review

References (221)

1. World Health Organization. (2002) Tech. Rep. Ser. 905, 1-109.
2. Urbina, J.A., Docampo, R. (2003) Trends in Parasitol. 19, 495-501.
3. Marr, J.J., Docampo, R. (1986) Rev. Infect. Dis. 8 (6), 884-903.
4. Huang, H., Chan, J., Wither, M., Jelicks, L.A., Morris, S.A., Factor, S.M., Weiss, L.M., Braunstein, V., L., Bacchi, C., J., Yarlett, N., Chandra, M., Shirani, J., Tanowitz, H.B. (1999) J. Mol. Cell Cardiol 31, 75-88.
5. Kierszenbaum, F. (1999) Clin. Microbiol. Reviews. 12 (2), 210-223.
6. Kierszenbum, F., Villalta, F., Tai, P-Ch. (1986) J. Immunol. 136 (2), 662-666.
7. Villalta, F.Kierszenbaum, F. (1983) J. Immunol. 131, 1504-1510.
8. Perez-Fuentes, R., Guegan, J.F., Barnabe, C., Lopez-Colombo, A., Salgado-Rosas, H., Torres-Rasgado, E., Briones, B., Romero-Diaz, M., Ramos-Jimenez, J., Sanchez-Guillen, M. (2003) Int. J. Parasitol. 33 (3), 293-299.
9. Krauth-Siegel, R.L., Schöneck, R. (1995) FASEB J. 9, 1138-1146.
10. De, Castro, S.L., Soeiro, M.N.C., De, Meirelles, M.N.L. (1992) Mem. Inst. Oswaldo Cruz. 87 (2), 209-215.
11. Fernandez, R.A., Fretes, R., Rubiales, S., Lacuara, J.L., Paglini-Oliva, P. (1997) Medicina (Buenos Aires) 57, 59-63.
12. Oliveira, M.M., Antunes, A., Mello, F.G. (1984) Mol. Biochem. Parasitol. 11, 283-292.
13. Tellez-Iñon, M.T., Ulloa, R.M., Torruela, M, Torres, H.N. (1985) Mol. Biochem. Parasitol. 17, 143-153.
14. Rivarola, H.W., Fernandez, R.A., Enders, J.E., Fretes, R., Gea, S., Suligoy, M., Palma, J.A., Paglini-Oliva, P. (1999) Ann. Trop. Med. Parasitol. 93(7), 695-702.
15. Hammond, D. J., Cover, B., Gutteridge, W.B. (1984) Trans R. Soc. Trop. Med. Hyg. 76, 91-95.
16. Benson, T.J., McKie, J.H:, Garforth, J., Borges, A., Fairlamb, A.H., Douglas, K.T. (1992) Biochem. J. 286, 9-11.
17. Chan, C., Yin, H., Garforth, J., McKieJ.H., Jaouhari, R., Speers, P., Douglas, K.T., Rock, P.J., Yardley, V., Croft, S.L., Fairlamb, A.H. (1998) J. Med. Chem. 41, 148-156.
18. Gutierrez-Correa, J.Fairlamb, A.H., Stoppani, A.O.M. (2001) Rev. Argentina Microbiol. 33, 36-46.
19. Gutierrez-Correa, J., Fairlamb, A.H., Stoppani, A.O.M. (2001) Free Rad. Res. 34, 363-378.
20. Fairlamb, A.H., Cerami, A. (1992) Annu. Rev. Microbiol. 46, 695-729.
21. Nogoceke, E., Gommel, D.U., Kieß, H.M., Flohé, L. (1997) Biol. Chem. 378, 827-836.
22. Lopez, J.A., Carvalho, T.U., De, Souza, W., Flohé, L., Guerrero, S.A., Montemartini, M., Kalisz, H.M., Nogoceke, E., Singh, M., Alves, M.J.M., Colli, W. (2000) Free Radic. Biol. Med. 28 (5), 767-772.
23. Fairlamb, A.H. (1996) Biochemist. 18, 11-16.
24. Blumenstiel, K, Schöneck, R., Yardley, V., Croft, S.L., Krauth-Siegel, R.L. (1999) Biochem. Pharmacol. 58, 1791-1799.
25. Krieger, S., Schwarz, W., Ariyanayagam, M.R., Fairlamb, A.H., Krauth-Siegel, R.L., Clayton, C. (2000) Mol. Microbiol. 35 (3), 542-552.
26. Boveris, A., Stoppani, A.O. (1977) Experientia 33 (10), 1306-1308.
27. Docampo, R., de, Boiso, J.F., Boveris, A., Stoppani, A.O.M. (1976) Experientia 32 (8), 972-975.
28. Boveris, A., Sies, H., Martino, E.E., Docampo, R, Turrens, J.F., Stoppani, A.O.M. (1980) Biochem. J. 188, 643-648.
29. Gutierrez-Correa, J., Krauth-Siegel, R.L., Stoppani, A.O.M. (2000) Free Rad. Res. 33, 13-22.
30. Levy, L., Tozer, T.N., Loveland, T.B. (1972) J. Med. Chem. 15, 898-905.
31. Motohashi, N., Gollapudi, S.R., Emrani, J., Bhattiprolu, K.R. (1991) Cancer Invest. 9 (3), 305-319.
32. Nagy, S., Argyelan, N.S., Molnar, J., Kawase, M., Motohashi, N. (1996) Anticancer Res. 16 (4A), 1915-1918.
33. Motohashi, N., Kurihara, T., Kawase, M., Hever, A., Tanaka, M., Szabo, D.; Nacsa, J., Yamanaka, W., Kerim, A., Molnar, J. (1997) Anticancer Res. 17 (5A), 3537-3543.
34. Satoh, K., Sakagami, H., Motohashi, N. (1997) Anticancer Res. 17 (4A), 2539-2543
35. Motohashi, N., Kawase, M., Molnar, J., Ferenczy, L., Wesolowska, O., Hendrich, A., B., Bobrowska-Hagerstrand, M., Hagerstrand, H., Michalak, K. (2003) Arzneimittelforschung. 53(8), 590-599.
36. Molnar, J., Molnar, A., Mucsi, I., Pinter, O., Nagy, B., Varga, S., Motohashi, N. (2003) In Vivo 17, 145-150.
37. Karreman, G., Isenberg, I., Szent-Györgyi. (1959) Science 130, 1191-1192.
38. Levy, L., Burbridge. (1967) Biochem. Pharmacol. 16, 1249-1260.
39. Borg, D.C., Cotzias, G.C. (1962) Proc. Natn. Acad. Sci. USA 48, 617-622.
40. Borg, D.C., Cotzias, G.C. (1962) Proc. Natn. Acad. Sci. USA 48, 623-642.
41. Ohnishi, S., McConnell, H.M. (1965) J. Amer. Chem. Soc. 87, 2293.
42. Motohashi, N., Kamata, K.K., Meyer, R. (1990) Anticancer Res. 10, 1611-1614.
43. Motohashi, N, Sakamoto, Y, Kojima, Y.K., Meyer, R., Kamata, K, (1992) In: Keyzer, H., Eckert, G M., Forrest, I.S., Gupta, R.R., Gutmann, F. and Molnár, J. (eds), Thiazines and Structurally Related Compounds. Krieger Publishing Company, Malabar, Florida, pp. 293-302.
44. Satoh, K, Sakagami, H., Kurihara, T., Motohashi, N. (1997) Anticancer Res. 17, 2465-2470.
45. Lovstad, R, A. (1974) Biochem. Pharmacol. 23, 1045-1052.
46. Lovstad, R.A. (1977) Acta Chem. Scand. B. 31 (2), 186-188.
47. Kulys, J., Krikstopaitis, K., Ziemys, A. (2000) J. Biol. Inorg. Chem. 5, 333-340.
48. Pérez-Gilabert, M, Sánchez-Ferrer, A., García-Carmona, F. (1994) Biochem. Pharmacol. 47, 2227-2232.
49. Rajadhyakska, A., Reddy, V., Hover, C., G., Kulkarni, A.P. (1999) Teratogen. Carcinogen. Mutagen. 19, 211-222.
50. Piette, L.H., Bulow, G., Yamazaki, Y. (1964) Biochem. Biophys. Acta 88, 120-129.
51. De, Mol, N.J., Becht, A.B.C., Koenen, J., Lodder, G. (1986) Chem. Biol. Interact. 57, 73-83.
52. Kelder, P, P, De, Mol, N, J, Hart, B.A, Janssen, L.H.M. (1991) Chem. Biol. Interact. 79, 15-30.
53. Kelder, P.P., Fischer, M.J.E., de, Mol, N.J., Janssen, L.H.M. (1991) Arch. Biochem. Biophys. 284(2), 313-319.
54. Lovstad, R.A. (1980) Gen. Pharmacol. 11 (3), 331-336.
55. Kelder, P.P., de, Mol, N.J., Janssen, L.H.M. (1991) Biochem. Pharmacol. 42, 1551-1559.
56. Kelder, P.P., de, Mol, N.J., Fischer, M.J.E., Janssen, L.H.M. (1994) Biochim. Biophys. Acta 1205, 230-238.
57. Gutierrez-, Correa, J., Stoppani, A.O.M. (2002) Rev. Argentina Microbiol. 34, 83-94.
58. Jaffe, H.H. (1953) Chem. Rev. 53, 191-261.
59. Lovstad, R.A. (1975) Biochem. Pharmacol. 24, 475-478
60. Cheng, H.Y., Sackett, P.H., McCreery, R.L. (1978) J. Am. Chem. Soc. 100 (3), 962-967.
61. Pan, D., Shoute, L.C.T., Phillips, D.L. (2000) J. Phys. Chem. A. 104 (18), 4140-4148.
62. Dunford, HB, Adeniran, A.J. (1986) Arch. Biochem. Biophys. 251, 536-542.
63. Escribano, J., Garcia-Cánovas, F., Garcia-Carmona, F.Lozano, J.A. (1985) Biochim. Biophys. Acta 831, 313-320.
64. Wardman, P. (2002) Curr. Pharm. Des. 8, 1363-1374.
65. Folkes, L.K., Rossiter, S., Wardman, P. (2002) Chem. Res. Toxicol. 15, 877-882.
66. Yamazaki, I., Piette, L.H. (1963) Biochim. Biophys. Acta 77, 47-64.
67. Wittenberg, J.B., Noble, R.W., Wittenberg, B.A., Antonio, E., Brunori, M., Wyman, J. (1967) J. Biol. Chem. 242, 626-634.
68. Adediran, S.A. (1996) Arch. Biochem. Biophys. 327(2), 279-284
69. Candeias, L.P., Folkes, L.K., Wardman, P. (1997) Biochemistry 36, 7081-7085.
70. Klebanoff, S.J. (1993) Free Radic. Biol. Med. 14, 351-360.
71. Daugherty, A., Dunn, J., L., Rateri, D.L., Heinecke, J.W. (1994) J. Clin. Invest. 94, 437-444.
72. Hazen, S.L., Heinecke, J.W. (1997) J. Clin. Invest. 99(9), 2075-2081.
73. Nauseef, W.M. (1998) J. Mol. Med. 76, 661-668.
74. Nauseef, W.M., McCormick, S., Goedken (2000) Redox Report 5, 197-206.
75. Kooter, I.M., Moguilevsky, N., Bollen, A., Sijtsema, N.M., Otto, C., Dekker, H.L., Wever, R. (1999) Eur. J. Biochem. 264, 211-217.
76. Kooter, I.M., Moguilevsky, N., Bollen, A., van den Veen, L.A., Otto, C., Dekker, H-L., Wever (1999) J. Biol. Chem. 274, 26794-26802.
77. Zeng, J., Fenna, R.E. (1992) J. Mol. Biol. 226, 185-207.
78. Furtmüller, P.G., Jantschko, W., Regelsberger, G., Jakopitsch, C., Moguilevsky, N., Obinger, C. (2001) FEBS Lett. 503, 147-150.
79. Kettle, A.J., Winterbourn, C.C. (1997) Redox Report 3(1), 3-15.
80. Furtmüller, P.G., Burner, U., Obinger, C. (1998) Biochemistry 37, 17923-17930.
81. Van Dalen, C.J., Whitehouse, M.W., Winterbourn, C., C., Kettle, A.J. (1997) Biochem. J. 327, 487-492.
82. Goldman, R., Claycamp, G.H., Sweetland, M.A., Sedlov, A.V., Tyurin, V.A., Kisin, E.R., Tyurina, Y.Y., Ritov, V.B., Wenger, S.L., Grant, S.G., Kagan, V.E. (1999) Free Radic. Biol. Med. 27, 1050-1063.
83. Eastmond, D.A., Smith, M.T., Ruzo, L.O., Ross, D. (1986) Mol. Pharmacol. 30, 674-679.
84. Metodiewa, D., Dunford, H.B. (1990) Eur. J. Biochem. 193, 445-448
85. Abu-Soud, H.M., Hazen, S.L. (2000) J. Biol. Chem. 275 (45), 37524-37532.
86. Kettle, A.J., Gedye, C.A., Winterbourn, C.C. (1993) Biochem. Pharmacol. 45, 2003-2010.
87. Kettle, A.J., Candeias, L.P. (2000) Redox Report. 5(4), 179-184.
88. Kettle, A.J., Winterbourn, C.C. (1994) J. Biol. Chem. 269(25), 17146-17151.
89. Allegra, M., Furtmüller, P.G., Regelsberger, G., Turco-Liveri, M.L., Tesoriere, L., Perretti, M., Livrea, M.A., Obinger, C. (2001) Biochem. Biophys. Res. Commun. 282, 380-386.
90. Kettle, A.J., Winterbourn, C.C. (1994) J. Biol. Chem. 269, 17146-17151
91. Svensson, B.E., Lindvall, S. (1988) Biochem. J. 249, 521-530.
92. Kettle, A.J., Winterbourn, C.C. (2001) Biochemistry 40, 17923-17930.
93. Alayash, A.I., Patel, R.P., Cashon, R.E. (2001) Antioxid. Redox Signal. 3, 313-327.
94. Winterbourn, C.C., McGrath, B.M., Carrell, R.W. (1976) Biochem. J. 155, 493-502.
95. Yusa, K., Shikama, K. (1987) Biochemistry 26, 6684-6688.
96. Carlsen, C.U., Moller, J.K.S., Skibsted, L.H. (2004) Coordination Chem. Rev. In press.
97. Egawa, T., Shimada, H., Ishimura, Y. (2000) J. Bio. Chem. 275 (45), 34858-34866.
98. Ostdal, H., Skibsted, L.H., Andersen, H.J. (1997) Free Radic. Biol. Med. 23 (5), 754-761.
99. Davies, M.J. (1991) Biochem. Biophys. Acta 1077, 86-90.
100. Giulivi, C., Cadenas, E. (1998) Free Radic. Biol. Med. 25 (2), 175-183.
101. Gunther, M.R., Kelman, D.J., Corbett, J.T., Mason, R.P. (1995) J. Biol. Chem. 270, 16075-16084.
102. Gunther, M.R., Tschirret-Guth, R.A., Witowska, H.E., Fann, Y.C., Barr, D.P., Ortiz, de, Montellano, P.R., Mason, R.P. (1998) Biochem. J. 330, 1293-1299.
103. Gunther, M.R., Sturgeon, B.E., Mason, R.P. (2000) Free Radic. Biol. Med. 28 (5), 709-719.
104. DeGray, J.A., Gunther, M., R., Tschirret-Guth, R., Ortiz, de, Montellano, P.R., Mason, R.P. (1997) J. Biol. Chem. 272 (4), 2359-2362.
105. Witting, P.K., Mauk, G.A. (2001) J. Biol. Chem. 276 (19), 16540-16547.
106. Witting, P.K., Mauk, G.A., Douglas, D.J., Stocker, R. (2001) Biochem. Biophys. Res. Commun. 286, 352-356.
107. Carlsen, C.U., Skovgaard, L.M., Skibsted, L.H. (2003) J. Agric. Food Chem. 51(19), 5815-5823.
108. Wolfenden, B.S., Willson, R.L. (1982) J. Chem. Soc. Perkin Trans. II, 805-812.
109. Gutierrez-Correa, J., Stoppani, A.O.M. (1997) Free Rad. Res. 27, 543-555
110. Gutierrez-Correa, J., Stoppani, A.O.M. (1998) An. Asoc. Quim. Argent. 86, 123-130.
111. King, N.K., Winfield, M.E. (1963) J. Biol. Chem. 238, 1520-1528.
112. Redaelli, C., Monzani, E., Santagostini, L., Casella, L., Sanangelantoni, A.M., Pierattelli, R., Banci, L. (2002) Chembiochem. 3 (2-3), 226-233.
113. Hersleth, H.P., Dalhus, B., Görbitz, C.H., Andersson, K.K. (2002) J. Biol. Inorg. Chem. 7, 299-304.
114. Reeder, B.J., Wilson, M.T. (2001) Free Radic. Biol. Med. 30 (11), 1311-1318.
115. Miura, T., Muraoka, S., Ogiso, T. (1995) Biochem. Mol. Biol. Int. 36 (3), 587-594.
116. Gunther, M.R., Sampath, V., Caughey, W.S. (1999) Free Radic. Biol. Med. 26 (11/12), 1388-1395.
117. Osawa, Y., Williams, M.S. (1996) Free Radic. Biol. Med. 21(1), 35-01.
118. Moore, K.P, Holt, S.G., Patel, R.P., Svistunenko, D.A., Zackert, W., Goodier, D., Reeder, B.J., Clozel, M., Anand, R., Cooper, C.E., Morrow, J.D., Wilson, M.T., Darley-Usmar, V., Roberts, L.J. (1998) J. Biol. Chem. 273, 31731-31737.
119. Reeder, B.J., Svistunenko, D.A., Sharpe, M.A., Wilson, M.T. (2002) Biochemistry 41, 367-375.
120. Leeuwenburgh, C., Wagner, P., Holloszy, J.O., Sohal, R.S., Heinecke, J.W. (1997) Arch. Biochem. Biophys. 346 (1), 74-80.
121. Lohrer, H., Krauth-Siegel, R.L. (1990) Eur. J. Biochem. 194, 863-869.
122. Schöneck, R., Billaut-Mulot, O., Numrich, P., Ouaissi, M.A., Krauth-Siegel, R.L. (1997) Eur. J. Biochem. 243, 739-747.
123. Gutierrez-Correa, J., Krauth-Siegel, R.L., Stoppani, A.O.M. (2003) Free Rad. Res. 37 (3), 281-291.
124. Mattevi, A., Schierbeek, A.J., Hol, W.G.J. (1991) J. Mol. Biol. 220, 975-994.
125. Jentoft, J.E., Shoham, M., Hurst, D., Patel, M.S. (1992)Proteins: Struct. Funct. Genet. 14, 88-101.
126. Benen, J., van, Berkel, W., Veeger, C., deKok, A. (1992) Eur. J. Biochem. 207, 499-505.
127. Williams, C.H. Jr. (1992) In Chemistry and Biochemistry of Flavoenzymes, vol 3. Lipoamide dehydrogenase, glutathione reductase, thioredoxin reductase and mercuric reductase. A Family of Flavoenzyme Transhydrogenases. (Müller, F. Ed.) pp. 121-211, CRC Press, Boca Raton, FL
128. Massey, V., Gibson, Q.H., Veeger, G. (1960) Biochem. J. 77, 341-351.
129. Mattews, R.G., Ballou, D.P., Thorpe, C., Williams, C.H. Jr. (1977) J. Biol. Chem. 252, 3199-3207.
130. Argyrou, A., Sun, G., Palfey, B.A., Blanchard, J.S. (2003) Biochemistry 42, 2218-2228.
131. Kagan, V.E., Shvedova, A., Serbinova, E., Kham, S., Swanson, C., Powell, R., Packer, L. (1992) Biochem. Pharmacol. 44, 1637-1649
132. Packer, L., Trischler, H.J., and, Wessel, K. (1997) Free. Radic. Biol. Med. 22, 359-378.
133. Shreider, C.M., Grinblat, L., Stoppani, A.O.M. (1990) Biochem. Pharmacol. 40 (8), 1849-1857.
134. Chen, H-J., C., Chen, Y-M., Chang, C-M. (2002) Chem-Biol. Interact. 140, 199-213.
135. Vienozinskis, J, Butkus, A., Cenas, N., Kulys, J. (1990) Bhicem. J. 269, 101-105.
136. Gutiérrez-Correa, J., Stoppani, A.O.M. (2000) Rev. Argent. Microbiol. 32, 136-143.
137. Argyrou, A., Blanchard, J.S. (2001) Biochemistry 50, 11353-11363.
138. Olsson, J.M., Xia, L., ErokssonL.C-, Björnsttedt, M. (1999) FEBS Lett. 448, 190-192.
139. Xia, L., Björnstedt, M., Nordman, T., Eriksson, L.C., Olsson, J.M. (2001) Eur. J. Biochem. 268, 1486-1490.
140. Argyrou, A., Sun, G., Palfey, B.A., Blanchard, J.S. (2003) Biochemistry 42, 2218-2228.
141. Bando, Y., Aki, K. (1991) J. Biochem. 450-454.
142. Gutierrez-Correa, J., Stoppani, A.O.M. (1999) Free Rad. Res. 30, 105-117.
143. De, Boiso, J.F., Stoppani, A., O.M. (1973) J. Protozool. 20, 673.
144. Saada, A., Aptowitzer, I., Link, G., Elpeleg, O. (2000) Biochem. Biophys. Res. Comm. 269, 382-386.
145. Van, Kammen, D.P., Marder, S.R. (1995) Dopamine Receptor Antagonists. In Kaplan, H.L., Saddock, B.J. Ed. Comprehensive Textbook of Psychiatry. Williams and Wilkins; Baltimore, pp 1987-2002.
146. Yang, X., Kulkarni, A.P. (1997) Teratogen Carcinogen Mutagen. 17, 139-151.
147. Bos, A., Wever, R., Roos, D. (1978) Biochim. Biophys. Acta 525, 37-44.
148. Rimoldi, M.T., Olabuenaga, S.E., Elizalde de Bracco, M.M. (1981) J. Protozool. 28, 351-354.
149. Crowle, A.J., Douvas, G.S., May, M.H. (1992) Exp. Chemother. 38, 410-419.
150. Hu, O.Y., Curry, S.H. (1989) Biopharm. Drug Dispos. 10, 537-548.
151. Ordway, D., Viveiros, M., Leandro, C., Bettencourt, R, Almeida, J., Martins, M., Kristiansen, J.E., Molnar, J., Amaral, L. (2003) Antimicrob. Agents Chemother. 47 (3), 917-922.
152. Paglini-Oliva, Fernandez, A.R., Fretes, T., Pelsman, A. (1998) Exp. Mol. Pathol. 65, 78-86.
153. Panousis, C.Kettle, A.J., Phillips, D.R. (1994) Biochem. Pharmacol. 48, 2223-2230.
154. McFaul, S.J., Lin, H., Everse, J. (1986) Proc. Soc. Exp. Biol. Med. 183 (2), 244-249.
155. Moore, K., L., Mehlhorn, R.J. (1993) Free Radic. Biol. Med. 14, 371-379.
156. Hillar, A., Loewen, P.C. (1995) Arch. Biochem. Biophys. 323 (2), 438-446.
157. Dessen, A., Quemard, A., Blanchard, J.S., Jacobs, W.R., Sacchettini, J.C. (1995) Science 267, 1638-1641.
158. Bryk, R., Lima, C.D., Erdjument-Bromage, H., Tempst, P., Nathan, C. (2002) Science 295 (5557), 1073-1077.
159. Koshkin, A., Nunn, C.M., Djordjevic, S., Ortiz, de, Montellano, P.R. (2003) J. Biol. Chem. 278 (32), 29502-29508.
160. Hait, W., N., Lazo, J.S. (1986) J. Clin. Oncol. 4 (6), 994-1012.
161. Weiss, B., Prozialeck, W., Cimino, M., Barnette, M.S., Wallace, T.L. (1980) Ann. N. Y. Acad. Sci. 356, 319-345.
162. Mercier, M.J., Dumont, P.A. (1972) Pharm. Pharmacol. 24, 706-712.
163. Hori, H., Fenna, R.E., Kimura, S., Ikeda-Saito, M. (1994) J. Biol. Chem. 269, 8388-8392.
164. Kocherginsky, N., Swartz, H.M. (1995) Nitroxide Spin Labels, Reactions in Biology and Chemistry, CRC Press, New York, pp 63-65.
165. Vasquez, A., Tudela, J., Varón, R., García-Cánovas, F. (1992) Biochem. Pharmacol. 44, 889-894.
166. Tamba, M., O'Neill, P. (1991) J. Chem. Soc. Perkin. Trans. 2, 1681-1685.
167. O'Brien, P.J. (1988) Free Radic. Biol. Med. 4, 169-183.
168. Wardman, P. (1995) Reactions of Thiyl Radicals. Biothiols in health and disease. Packer, L., Cadenas, E. (Ed) pp. 1-18. Marcel Dekker, Inc. New York.
169. Forni, L.G., Mönig, J., Mora-Arellano, V.O., Willson, R.L. (1983) J. Chem. Soc. Perkin. Trans. 2, 961-965.
170. Bando, M., Obazawa, H., Tanikawa, T. (1986) Free Radic. Biol. Med. 2, 261-266.
171. Buettner, G.R. (1993) Arch. Biochem. Biophys. 300 (2), 535-545.
172. Yang, E.Y., Campbell, A., Bondy, S.C. (2000) Redox Report 5 (6), 371-375.
173. Harman, L.S., Mottley, C., Mason, R, P. (1984) J. Biol. Chem. 259, 5606-5611.
174. Burner, U., Jantshko, W., Obinger, C. (1999) FEBS Lett. 443, 290-296.
175. Kapiotis, S., Hermann, M., Mühl, A., Gmeiner, B. (1997) FEBS Lett. 409, 223-226.
176. Heinecke, J.W., Li, W., Daehnke, H.L., Goldstein, J.A. (1993) J. Biol. Chem. 268, 4069-4077.
177. Marquez, L.A., Dunford, H.B. (1995) J. Biol. Chem. 270 (51), 30434-30440.
178. Tien, M. (1999) Arch. Biochem. Biophys. 367 (1), 61-66.
179. Francis, G.A., Mendez, A.J., Bierman, E.L., Heinecke, J.W. (1993) Proc. Natl. Acad. Sci. USA 90, 6631-6635.
180. Goodwin, D., D.C., Aust, S.D., Grover, T.A. (1995) Biochemistry 34, 5060-5065.
181. Goodwin, D.C., Grover, T.A., Aust, S.D. (1996) Chem. Res. Toxicol. 9, 476-483.
182. Goodwin, D., C., Grover, T., A., Aust, S.D. (1997) Biochemistry. 36, 139-147.
183. Olorunniji, F.J., Malomo, S.O., Adediran, S.A., Odutuga, A.A. (2000) Arch. Biochem. Biophys. 380 (2), 251-256.
184. Hunter, E.P.L., Desrosiers, M.F., Simic, M.G. (1989) Free Radic. Biol. Med. 6, 581-585.
185. Baker, C.J., Deahl, K., Domek, J., Orlandini, E.W. (2000) Arch. Biochem. Biophys. 382 (2), 232-237.
186. Barr, D.P., Aust, S.D. (1993) Arch. Biochem. Biophys. 303 (2), 377-382.
187. Winterbourn, C.C., Pichorner, H., Kettle, A.J. (1997) Arch. Biochem. Biophys. 338, 15-21.
188. DeFelippis, M.R., Murthy, C.P., Faraggi, M., Klapper, M.H. (1989) Biochemistry 28, 4847-4853.
189. Heinecke, J.W. (1997) Curr. Opin. Lipidol. 8, 268-271.
190. Ostdal, H., Davies, M.J., Andersen, H.J. (2002) Free Radic. Biol. Med. 33 (2), 201-209.
191. Irwin, J.A., Ostdal, H., Davies, M.J. (1999) Arch. Biochem. Biophys. 362 (1), 94-104.
192. Ostdal, H., Andersen, H.J., Davies, M.J. (1999) Arch. Biochem. Biophys. 362, 105-112.
193. Ostdal, H., Bjerrum, M.J., Pedersen, J.A., Andersen, H.J. (2000) J. Agric. Food Chem. 48, 3939-3944.
194. Van, Overveld, F.W.P.C., Haenen, G.R.M.M., Rhemrev, J., Vermeiden, J.P.W., Bast, A. (2000) Chem. Biol. Interact. 127, 151-161.
195. Moosman, B., Behl, C. (2000) Eur. J. Biochem. 267, 5687-5692.
196. Moosman, B., Behl, C. (2002) Mol. Pharmacol. 61, 260-268
197. Deterding, L.J., Barr, D.P., Mason, R.P., Tomer, K.R. (1998) J. Biol. Chem. 273, 12863-12869.
198. Lovstad, R.A. (1979) Gen. Pharmac. 10, 437-440.
199. Kirsch, M., De, Groot, H. (2001) FASEB J. 15, 1569-1574.
200. Schellenberg, K.A., Hellerman, L. (1958) J. Biol. Chem. 231, 547-556.
201. Land, E.J., Swalow, A.J. (1971) Biochim. Biophys. Acta 234, 34-42.
202. Kirkor, E.S., Scheeeline, A. (2000) Eur. J. Biochem. 267, 5014-5022.
203. Pelizzetti, E., Meisel, D., Mulac, W.A., Neta, P. (1979) J. Am. Chem. Soc. 101, 6954-6959.
204. Kröger-Ohlsen, M., Skibsted, L.H. (1997) J. Agric. Food Chem. 45, 668-676.
205. Giulivi, C., Cadenas, E. (1993) FEBS Lett. 332 (3), 287-290.
206. Romero, F.J., Ordoñez, I., Arduini, A., Cadenas, E. (1992) J. Biol. Chem. 267 (3), 1680-1688.
207. Galaris, D., Cadenas, E., Hochstein, P. (1989) Arch. Biochem. Biophys. 273 (2), 497-504.
208. Mikkelsen, A., Skibsted, L. H. (1995) Z. Lebensm Unters Forsch. 200, 171-177.
209. Galaris, D., Sevanian, A., Cadenas, E., Hochstein, P. (1990) Arch. Biochem. Biophys. 281 (1), 163-169.
210. Frimat, B., Gressier, B., Odou, P., Brunet, C., Dine, T., Luycky, M., Cazin, M., Cazn, J.C. (1997) Fundam. Clin. Pharmacol. 11, 267-274.
211. Hsuanyu, Y., Dunford, H.B. (1999) Arch. Biochem. Biophys. 368 (2), 413-429.
212. Davies, M., J., Forni, L.G., Willson, R.L. (1988) Biochem. J. 255, 513-522.
213. Metodiewa, D., Dunford, H.B. (1991) Biochem. Int. 25, 895-904.
214. Nakamura, M., Hayashi (1992) Arch. Biochem. Biophys. 299, 313-319.
215. Kagan, V., E., Kuzmenko, A.L, Shvedova, A.A., Kisin, E.R., Tyurina, Y.Y., Yalowich, J.C. (2000) Biochem. Biophys. Res. Commun. 270, 1086-1092.
216. Giulivi, C., Cadenas, E. (1993) Arch. Biochem. Biophys. 303, 152-158.
217. Guo, Q., Packer, L. (2000) Free Radic. Biol. Med. 29 (3/4) pp. 368-374
218. Carr, A., Frei, B. (1999) FASEB J. 13 (9), 1007-1024.
219. Heikkila, R.E., Cohen, G., Manian, A.A. (1975) Biochem. Pharmacol. 24, 363-368.
220. Everse, K.E., Lin, H., Stuyt, E, L., Brady, J, C., Buddingh, F., Everse, J. (1985) Br. J. Cancer 51, 743-746.
221. Kousparou, C.A., Epenetos, A.A., Deonarain, M.P. (2002) Int. J. Cancer. 99 (1), 138-148.