A novel class of cytochrome P450 reductase redox cyclers: Cationic manganoporphyrins

Toxicological Sciences

Volumn 85, Issue 1, 2005, Pages 713-719

  Day, Brian J ^a,b   Kariya, Chirag ^b  

^a NATIONAL JEWISH MEDICAL AND RESEARCH CENTER   (United States)

^b UNIVERSITY OF COLORADO   (United States)

Author keywords

Catalytic antioxidants; Human; Oxidoreductase; Rat; Xenobiotic metabolism

Indexed keywords

AEOL 10113; AEOL 10123; AEOL 10150; AEOL 10201; ANTIOXIDANT; BETA NAPHTHOFLAVONE; CARBON; CATION; CYTOCHROME P450 REDUCTASE; DIPHENYLIODONIUM SALT; IMIDAZOLE DERIVATIVE; MANGANESE DERIVATIVE; MESOTETRAKIS(1,3 DIETHYLIMIDAZOLIUM 2 YL)PORPHYRIN MANGANESE; MESOTETRAKIS(1,3 DIMETHYLIMIDAZOLIUM 2 YL)PORPHYRIN MANGANESE; MESOTETRAKIS(4 BENZOIC ACID)PORPHYRIN MANGANESE; MESOTETRAKIS(N ETHYLPYRIDINIUM 2 YL)PORPHYRIN MANGANESE; OXIDOREDUCTASE; OXYGEN; PARAQUAT; PORPHYRIN DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; RESORUFIN DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIOXIDANT ACTIVITY; ARTICLE; CATALYSIS; CONTROLLED STUDY; CORRELATION ANALYSIS; DEALKYLATION; DRUG POTENCY; DRUG STRUCTURE; HUMAN; HUMAN CELL; IN VITRO STUDY; LIVER MICROSOME; METABOLIC REGULATION; NONHUMAN; OXIDATION REDUCTION REACTION; POLAROGRAPHY; RAT; RISK BENEFIT ANALYSIS; SPECTROFLUOROMETRY; SPECTROPHOTOMETRY; XENOBIOTIC METABOLISM;

ANIMALS; ANTIOXIDANTS; CATIONS; CYTOCHROME P-450 CYP2B1; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; MANGANESE; METALLOPORPHYRINS; MICROSOMES, LIVER; NADPH-FERRIHEMOPROTEIN REDUCTASE; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; OXIDOREDUCTASES; RATS; RECOMBINANT PROTEINS; XENOBIOTICS;

EID: 18144396884     PISSN: 10966080     EISSN: None     Source Type: Journal    
DOI: 10.1093/toxsci/kfi108     Document Type: Article

References (40)

1. Bartoszek, A., and Wolf, C. R. (1992). Enhancement of doxorubicin toxicity following activation by NADPH cytochrome P450 reductase. Biochem. Pharmacol, 43, 1449-1457.
2. Batinic-Haberle, I., Benov, L., Spasojevic, I., and Fridovich, I. (1998). The ortho effect makes manganese(III) meso-tetrakis(N-methylpyridinium-2-yl)porphyrin a powerful and potentially useful superoxide dismutase mimic. J. Biol. Chem. 273, 24521-24528.
3. Baud, L, and Ardaillou, R. (1986). Reactive oxygen species: Production and role in the kidney. Am. J, Physiol. 251, F765-F776.
4. Baudry, M., Etienne, S., Bruce, A., Palucki, M., Jacobsen, E., and Malfroy, B. (1993). Salen-manganese complexes are superoxide dismutase-mimics, Biochem. Biophys, Res, Commun. 192, 964-968.
5. Burke, M, D., and Mayer, R. T, (1983). Differential effects of phenobarbitone and 3-methylcholanthrene induction on the hepatic microsomal metabolism and cytochrome P-450-binding of phenoxazone and a homologous series of its n-alkyl ethers (alkoxyresorufins). Chem. Viol. Interact. 45, 243-258.
6. Byczkowski, J. Z., and Kulkarni, A. P. (1989), NADPH-dependent drug redox cycling and lipid peroxidation in microsomes from human term placenta. Int. J. Biochem. 21, 183-190.
7. Choi, A. M., and Alam, J. (1996). Heme oxygenase-1: Function, regulation, and implication of a novel stress-inducible protein in oxidant-induced lung injury. Am. J. Respir Cell. Mol. Biol. 15, 9-19.
8. Comporti, M. (1989). Three models of free radical-induced cell injury. Chem. Biol. Interact. 72, 1-56.
9. Day, B. J. (2004). Catalytic antioxidants: A radical approach to new therapeutics. Drug Discov. Today 9, 557-566.
10. Day, B. J., Batinic-Haberle, I., and Crapo, J. D. (1999a). Metalloporphyrins are potent inhibitors of lipid peroxidation. Free Radic. Biol. Med. 26, 730-736.
11. Day, B. J., Fridovich, I., and Crapo, J. D. (1997). Manganic porphyrins possess catalase activity and protect endothelial cells against hydrogen peroxide-mediated injury. Arch. Biochem. Biophys, 347, 256-262.
12. Day, B. J., Patel, M., Calavetta, L., Chang, L, Y., and Stamler, J. S. (1999b). A mechanism of paraquat toxicity involving nitric oxide synthase. Proc. Natl. Acad. Sci. U.S.A. 96, 12760-12765.
13. Djinovic, K., Coda, A., Antolini, L., Pelosi, G., Desideri, A, Falconi, M., Rotilio, G., and Bolognesi. M. (1992). Crystal structure solution and refinement of the semisynthetic cobalt-substituted bovine erythrocyte superoxide dismutase at 2.0 A resolution, J. Mol. Biol. 226, 227-238.
14. Forman, H. J., and Torres, M. (2002), Reactive oxygen species and cell signaling: Respiratory burst in macrophage signaling. Am. J. Respir. Crit. Care Med. 166, S4-8.
15. Gonzalez, F. J. (1992). Human cytochromes P450: problems and prospects. Trends Pharmacol. Sci. 13, 346-352.
16. Grisham, M. B., and Granger, D. N. (1988). Neutrophil-mediated mucosal injury. Role of reactive oxygen metabolites. Dig. Dig. Dis. Sci. 33, 6S-15S.
17. Gross, S. S., and Wolin, M. S. (1995). Nitric oxide: Pathophysiological mechanisms. Annu. Rev. Physiol. 57, 737-769.
18. Hochstein, P. (1983). Futile redox cycling: Implications for oxygen radical toxicity. Fundam. Appl. Toxicol. 3, 215-217.
19. Kachadourian, R., Johnson, C. A., Min. E., Spasojevic, I., and Day, B. J. (2004). Flavin-dependent antioxidant properties of a new series of meso-N,N′-dialkyl-imidazolium substituted manganese(III) porphyrins. Biochem. Pharmacol. 67, 77-85.
20. Kappus, H., and Sies, H. (1981). Toxic drug effects associated with oxygen metabolism: Redox cycling and lipid peroxidation. Experientia 37, 1233-1241.
21. Lambeth, J. D. (2002). Nox/Duox family of nicotinamide adenine dinucleotide (phosphate) oxidases. Curr. Opin. Hematol. 9, 11-17.
22. Liochev, S. I., and Fridovich, I. (2000). Copper- and zinc-containing superoxide dismutase can act as a superoxide reductase and a superoxide oxidase. J. Biol. Chem. 275, 38482-38485.
23. Lubet, R. A., Syi, J. L., Nelson, J. O., and Nims, R. W. (1990). Induction of hepatic cytochrome P-450 mediated alkoxyresorufin O-dealkylase activities in different species by prototype P-450 inducers. Chem. Biol. Interact. 75, 325-339.
24. Macarthur, H., Couri, D. M., Wilken, G. H., Westfall, T. C., Lechner, A. J., Matuschak, G. M., Chen, Z., and Salvemini, D. (2003). Modulation of serum cytokine levels by a novel superoxide dismutase mimetic, M40401, in an Escherichia coli model of septic shock: Correlation with preserved circulating catecholamines. Crit. Care Med. 31, 237-245.
25. McDonald, M. C., d'Emmanuele di Villa Bianca, R., Wayman, N. S., Pinto, A., Sharpe, M. A., Cuzzocrea, S., Chatterjee, P. K., and Thiemermann, C. (2003). A superoxide dismutase mimetic with catalase activity (EUK-8) reduces the organ injury in endotoxic shock. Eur J. Pharmacol. 466, 181-189.
26. McGuire, J. J., Anderson, D. J., and Bennett, B. M. (1994). Inhibition of the biotransformation and pharmacological actions of glyceryl trinitrate by the flavoprotein inhibitor, diphenyleneiodonium sulfate. J. Pharmacol. Exp. Ther. 271, 708-714.
27. Novak, J., Jr., and Qualls, C. W., Jr. (1989). Effects of phenobarbital and 3-methylcholanthrene on the hepatic cytochrome P-450 metabolism of various alkoxyresorufin ethers in the cotton rat (Sigmodon hispidus). Comp. Biochem. Physiol. C 94, 543-545.
28. Pasternack, R. F., and Skowronek, W. R., Jr. (1979). Catalysis of the disproportionation of superoxide by metalloporphyrins. J. Inorg. Biochem. 11, 261-267.
29. Pfeiffer, S., Lass, A., Schmidt, K., and Mayer, B. (2001). Protein tyrosine nitration in mouse peritoneal macrophages activated in vitro and in vivo: Evidence against an essential role of peroxynitrite. FASEB J. 15, 2355-2364.
30. Pfeiffer, S., Schrammel, A., Koesling, D, Schmidt, K., and Mayer, B. (1998). Molecular actions of a Mn(III)Porphyrin superoxide dismutase mimetic and peroxynitrite scavenger: Reaction with nitric oxide and direct inhibition of NO synthase and soluble guanylyl cyclase. Mol. Pharmacol. 53, 795-800.
31. Rashba-Step, J., and Cederbaum, A. I. (1994). Generation of reactive oxygen intermediates by human liver microsomes in the presence of NADPH or NADH. Mol. Pharmacol. 45, 150-157.
32. Rosen, G. M., Pou, S., Ramos, C. L., Cohen, M. S., and Britigan, B. E. (1995). Free radicals and phagocytic cells. FASEB J. 9, 200-209.
33. Salvemini, D., Wang, Z. Q., Zweier, J. L., Samouilov, A., Macarthur, H., Misko, T. P., Currie, M. G., Cuzzocrea, S., Sikorski, J. A., and Riley, D. P. (1999). A nonpeptidyl mimic of superoxide dismutase with therapeutic activity in rats. Science 286, 304-306.
34. Schacter, B. A., Nelson, E. B., Marver, H. S., and Masters, B. S. (1972). Immunochemical evidence for an association of heme oxygenase with the microsomal electron transport system. J. Biol Chem. 247, 3601-3607.
35. Szabo, C., Day, B. J., and Salzman, A. L. (1996). Evaluation of the relative contribution of nitric oxide and peroxynitrite to the suppression of mitochondrial respiration in immunostimulated macrophages using a manganese mesoporphyrin superoxide dismutase mimetic and peroxynitrite scavenger. FEBS Lett. 381, 82-86.
36. Szabo, C., Mabley, J. G., Moeller, S. M., Shimanovich, R., Pacher, P., Virag, L., Soriano, F. G., Van Duzer, J. H., Williams, W., Salzman, A. L., and Groves, J. T. (2002). Part I: Pathogenetic role of peroxynitrite in the development of diabetes and diabetic vascular complications: Studies with FP15, a novel potent peroxynitrite decomposition catalyst. Mol. Med. 8, 571-580.
37. Tindberg, N., and Ingelman-Sundberg, M. (1989). Cytochrome P-450 and oxygen toxicity. Oxygen-dependent induction of ethanol-inducible cytochrome P-450 (IIE1) in rat liver and lung. Biochemistry 28, 4499-4504.
38. Vermilion, J. L., and Coon, M. J. (1978). Identification of the high and low potential flavins of liver microsomal NADPH-cytochrome P-450 reductase. J. Biol. Chem. 253, 8812-8819.
39. Wang, W., Jittikanont, S., Falk, S. A., Li, P., Feng, L., Gengaro, P. E., Poole, B. D., Bowler, R. P., Day, B. J., Crapo, J. D., and Schrier, R. W. (2003). Interaction among nitric oxide, reactive oxygen species, and antioxidants during endotoxemia-related acute renal failure. Am. J. Physiol. Renal Physiol. 284, F532-F537.
40. Weissmann, G., Serhan, C., Korchak, H. M., and Smolen, J. E. (1982). Neutrophils: Release of mediators of inflammation with special reference to rheumatoid arthritis. Ann. N. Y. Acad. Sci. 389, 11-24.