A comparative study of the redox-cycling of a quinone (rifamycin S) and a quinonimine (rifabutin) antibiotic by rat liver microsomes

Free Radical Biology and Medicine

Volumn 22, Issue 3, 1997, Pages 439-446

  Rao, D N Ramakrishna ^a   Cederbaum, Arthur I ^a,b  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b MOUNT SINAI SCHOOL OF MEDICINE   (United States)

Author keywords

Free radicals; Hydroxyl Radical; Rat Liver Microsomes; Redox Cycling; Rifabutin; Rifamycin S

Indexed keywords

CHELATING AGENT; FERROUS ION; FREE RADICAL; HYDROXYL RADICAL; LEPROSTATIC AGENT; QUINONE DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; RIFABUTIN; RIFAMYCIN S; TUBERCULOSTATIC AGENT;

ANIMAL TISSUE; ARTICLE; COMPLEX FORMATION; DRUG OXIDATION; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; LEPROSY; LIPID PEROXIDATION; LIVER MICROSOME; LIVER MITOCHONDRION; MALE; NONHUMAN; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; RAT; TUBERCULOSIS;

ANIMALS; ANTI-BACTERIAL AGENTS; ANTIBIOTICS, ANTITUBERCULAR; HYDROGEN PEROXIDE; HYDROXYL RADICAL; MALE; MICROSOMES, LIVER; NAD; NADP; OXIDATION-REDUCTION; RATS; RATS, SPRAGUE-DAWLEY; RIFABUTIN; RIFAMYCINS; SPECTROPHOTOMETRY; SUPEROXIDES;

EID: 0031024633     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(96)00335-8     Document Type: Article

References (48)

1. Lester W. Rifamycin; a Semisynthetic Derivative of Rifamycin - a Prototype of the Future. Annu. Rev. Microbiol. 26:1972;85-102.
2. Pretet S., Lebeaut A., Parrot R., Truffot C., Grosset J., Dinh-Xuan A. T. Combined Chemotherapy Including Rifabutin for Rifampicin, and Isoniazid Resistant Pulmonary Tuberculosis. Eur. Respir. J. 5:1992;680-684.
3. Yoder L. J., Jacobson R. R., Hastings R. C. The Activity of Rifabutin Against Mycobacterium Leprae. Lepr. Rev. 62:1991;280-287.
4. Dhople A. M., Ibanez M. A. In Vivo Susceptibility of Mycobacterium Leprae to Ofloxacin Either Singly or in Combination with Rifampicin and Rifabutin. Anti-Leprosy Activity of Ofloxacin and Ansamycins in Mice. Arzneimittelforschung. 44:1994;563-565.
5. Thayer W. R. The Use of Anti-Mycobacterial Agents in Crohn's Disease. J. Clin. Gastroenterol. 15:1992;5-7.
6. Brogden R. N., Fitton A. Rifabutin; a Review of its Anti-Microbial Activity, Pharmacokinetic Properties and Therapeutic Efficacy. Drugs. 47:1994;983-1009.
7. Wehrli W., Nuesch J., Knusel F., Stachelin M. Action of Rifamycins on RNA Polymerase. Biochim. Biophys. Acta. 157:1968;215-217.
8. Travers A. A., Burgess R. R. Cyclic Re-Use of the RNA Polymerase Sigma Factor. Nature. 222:1969;537-540.
9. Scrutton M. C., Wu C. W., Goldthwait D. A. The Presence and Possible Role of Zinc in RNA Polymerase Obtained from E. coli. Proc. Natl. Acad. Sci (USA). 68:1971;2497-2501.
10. Kono Y. Oxygen Enhancement of Bacterial Activity of Rifamycin SV on E. Coli and Aerobic Oxidation of Rifamycin SV to Rifamycin S Catalyzed by Manganous Ions: the Role of Superoxide. J. Biochem. 91:1982;381-395.
11. Kono Y., Sugiuhara Y. Electron Spin Resonance Studies on the Oxidation of Rifamycin SV Catalyzed by Metal Ions. J. Biochem. 91:1987;397-401.
12. Quinlan G. J., Gutteridge J. M. C. Oxygen Radical Damage to DNA by Rifamycin SV and Copper Ions. Biochem. Pharmacol. 36:1987;3629-3633.
13. Quinlan G. J., Gutteridge J. M. C. DNA Base Damage by β-Lactam , Tetracycline, Bacitracin, and Rifamycin Antibacterial Antibiotics. Biochem. Pharmacol. 42:1991;1595-1599.
14. Zweir J. L. Iron-Mediated Formation of an Oxidized Adriamycin free Radical. Biochim. Biophys. Acta. 839:1985;209-213.
15. Powis G. Free Radical Formation by Antitumor Quinones. Free Rad. Biol. Med. 6:1989;63-101.
16. Dikalov S., Alou P., Rangelova D. Role of Iron Chelation by Quinones in their Reduction, OH-Radical Generation and Lipid Peroxidation. Biochem. Biophys. Res. Commun. 195:1993;1113-1119.
17. Dikalov S. I., Rumyantseva G. V., Piskunov A. V., Weiner L. M. Role of Quinone-Iron(III) Interaction in NADPH-Dependent Enzymatic Generation of Hydroxyl Radicals. Biochemistry. 31:1992;8947-8953.
18. Hollins P. J., Simmons A. V. Jaundice Associated with Rifamycin. Tubercle. 51:1970;328-332.
19. Lees A. W., Ascher B., Hashem M. A., Sinha B. N. Jaundice after Rifampicin. Br. J. Dis. Chest. 64:1971;90-95.
20. Scampini G., Nava A., Newman A. J., Della-Torre P., Mazue G. Multinucleated Hepatocytes Induced by Rifabutin in Rats. Toxicol. Pathol. 21:1993;369-376.
21. Saez G. T., Valls V., Muniz P., Perez-Broseta C., Iradi A., Oliva M. R., Bannister J. V., Bannister W. H. The Role of Glutathione in Protection Against DNA Damage Induced by Rifamycin SV and Cu(II) Ions. Free Rad. Res. Commun. 19:1993;81-92.
22. Kukielka E., Dicker E., Cederbaum A. I. Stimulation of NADH-dependent Microsomal DNA Strand Cleavage by Rifamycin SV. Biochem. J. 307:1995;361-367.
23. Kukielka E., Cederbaum A. I. Stimulation of Microsomal Production of Reactive Oxygen Intermediates by Rifamycin SV: Effect of Ferric Complexes and Comparisons Between NADPH and NADH. Arch. Biochem. Biophys. 298:1992;602-611.
24. Rietjens I. M., Tyrakowska B., Veeger C., Vervoort J. Reaction Pathways for Biodehalogenation of Fluorinated Anilines. Eur. J. Biochem. 194:1990;945-956.
25. Mau B-L., Powis G. Mechanism-Based Inhibition of Thioredoxin Reductase by Antitumor Quinoid Compounds. Biochem. Pharmacol. 43:1992;1613-1620.
26. Laurialt V. M., O'Brien P. J. Molecular Mechanism for Prevention of N-Acetyl-P-Benzoquinonimine Cytotoxicity by the Permeable Thiol Drugs Diethyldithiocarbamate and Dithiothreitol. Mol. Pharmacol. 40:1991;125-134.
27. Harrison A. C., Kitteringham N. R., Clarke J. B., Park B. K. The Mechanism of Bioactivation and Antigen Formation of Amodiaquine in the Rat. Biochem. Pharmacol. 43:1992;1421-1430.
28. Albano E., Rundgren M., Harvison P. J., Nelson S. D., Moldeus P. Mechanisms of N-Acetyl-P-Benzoquinonenimine Cytotoxicity. Mol. Pharmacol. 28:1985;306-311.
29. Kalyanaraman B., Premovic P. I., Sealy R. C. Semiquinone Anion Radicals from Addition of Amino Acids, Peptides, and Proteins to Quinones Derived from Oxidation of Catechols and Catecholamines. An ESR Spin Stabilization Study. J. Biol. Chem. 262:1987;11080-11087.
30. Omura T., Sato R. The Carbon Monoxide Pigment of Liver Microsomes. J. Biol. Chem. 239:1964;2370-2378.
31. Kukielka E., Dicker E., Cederbaum A. I. Increased Production of Reactive Oxygen Species by Rat Liver Mitochondria after Chronic Ethanol Treatment. Arch. Biochem. Biophys. 309:1994;377-386.
32. Bradford M. H. A Rapid and Sensitive Method for the Quantitation of Microgram Quantities of Protein Utilizing the Principle of Protein-Dye Binding. Anal. Biochem. 72:1976;248-253.
33. Rao D. N. R., Cederbaum A. I. Production of Nitric Oxide and other Iron-Containing Metabolites During the Reductive Metabolism of Nitroprusside by Microsomes and by Thiols. Arch. Biochem. Biophys. 321:1995;363-371.
34. Morrisett J. D. Spin-labelling Theory and Applications. Berliner L. J. 1976;272-338 Academic Press, Orlando, FL.
35. Buege J. A., Aust S. D. Microsomal Lipid Peroxidation. Meth. Enzymol. 52:1978;302-310.
36. Ponganis K. V., Dearaujo M. A., Hodges H. L. A Kinetic Investigation of the Oxidation of bis (1,10-Phenanthroline) Copper(II) by Hydrogen Peroxide in Aqueous and Sodium Dodecyl Sulfate Solution. Inorg. Chem. 19:1980;2704-2709.
37. Johnson G. R. A., Nazhat N. B., Saadalla-Nazhat R. A. Reaction of the Aquocopper(I) Ion with Hydrogen Peroxide: Evidence Against Hydroxyl Free Radical Formation. J. Chem. Soc. Chem. Commun. 1985;407-408.
38. Talcott R. E., Smith M. T., Giannini D. D. Inhibition of Lipid Peroxidation by Naphthoquinones: Structure-Activity Relationships and Possible Mechanisms of Action. Arch. Biochem. Biophys. 241:1985;88-94.
39. Suno M., Nagaoka A. Inhibition of Lipid Peroxidation by Idebenone in Brain Mitochondria in the Presence of Succinate. Arch. Gerontol. Geriatr. 8:1989;291-297.
40. Belisario M. A., Maturo M., Pecce R., De Rosa S., Villani G. R. D. Effect of Avarol and Avarone on an In Vitro-induced Microsomal Lipid Peroxidation. Toxicology. 72:1992;221-233.
41. O'Brien P. J. Molecular Mechanisms of Quinone Cytotoxicity. Chem-Biol. Interact. 80:1991;1-41.
42. Kappus H., Muliawan H., Scheulen M. E. Holnstedt B., Lauwerys A., Mercer M., Robenfroid M. Mechanisms of Toxicity and Hazard Evaluation. 1980;635 Elsevier, Oxford.
43. Minotti G., Aust S. D. Redox Cycling of Iron and Lipid Peroxidation. Lipids. 27:1992;219-226.
44. Afanasev I. B., Dorozhko A. I., Polozova N. I., Kuprianova N. S., Brodoskii A. I., Ostrachovitch E. A., Korkina L. G. Is Superoxide an Initiator of Microsomal Lipid Peroxidation? Arch. Biochem. Biophys. 302:1993;200-205.
45. Sausville E. A., Horwitz J. B. Crooke S. Effects of Drugs on the Cell Nucleus. 1979;181 Academic Press, New York.
46. Myers C. E., Gianni L., Simone C. B., Klecker R., Greene R. Oxidative Destruction of Erythrocyte Ghost Membranes Catalyzed by the Doxorubicin-Iron Complex. Biochemistry. 21:1982;1707-1713.
47. Lynch M. W., Valentine M., Hendrickson D. N. Mixed Valence Semiquinone-Catecholate-Iron Complexes. J. Am. Chem. Soc. 104:1982;6982-6989.
48. Buchanan R. M., Kessel S. L., Downs H. H., Pierpont C. G., Hendrickson D. N. Structural and Magnetic Properties of Tris(O-Semiquinone) Complexes of Iron(III) and Chromium(III). J. Am. Chem. Soc. 100:1978;7894-7900.