Reactivity of reduced [2Fe-2S] ferredoxins parallels host susceptibility to nitroimidazoles

Antimicrobial Agents and Chemotherapy

Volumn 47, Issue 1, 2003, Pages 302-308

  Vidakovic, Momcilo ^a   Crossnoe, Chetlen R ^a   Neidre, Christopher ^a   Kim, Kyonghee ^a   Krause, Kurt L ^a   Germanas, Juris P ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

DNA; FERREDOXIN; HETEROCYCLIC COMPOUND; NITROIMIDAZOLE DERIVATIVE;

ANABAENA; ARTICLE; CYANOBACTERIUM; DNA SYNTHESIS INHIBITION; DRUG SENSITIVITY; DRUG STRUCTURE; ELECTRON TRANSPORT; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTOZOAL INFECTION; STRUCTURE ACTIVITY RELATION; TRICHOMONAS VAGINALIS; TRICHOMONIASIS;

EID: 0037224473     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.47.1.302-308.2003     Document Type: Article

References (26)

1. Bohme, H., and B. Schrautemeier. 1987. Comparative characterization of ferredoxins from heterocysts and vegetative cells of Anabaena variabilis. Biochim. Biophys. Acta 891:1-7.
2. Butler, K., H. L. Howes, J. E. Lynch, and D. K. Pirie. 1967. Nitroimidazole derivatives. Relationship between structure and antitrichomonal activity. J. Med. Chem. 10:891-897.
3. Crossnoe, C. R., J. P. Germanas, P. LeMagueres, G. Mustata, and K. L. Krause. 2002. The crystal structure of Trichomonas vaginalis ferredoxin provides insight into metronidazole activation. J. Mol. Biol. 308:503-518.
4. Dunn, B. E., H. Cohen, and M. J. Blaser. 1997. Helicobacter pylori. Clin. Microbiol. Rev. 10:720-741.
5. Edwards, D. I., J. H. Tochler, L. D. Dale, D. A. Widdick, D. A., and N. S. Virk. 1990. Effects on DNA of bioreducible nitroimidazole and benzotriazine drugs, p. 275-283. In G. E. Adams, A. Breccia, M. Fielden, and P. Wardman, (ed.), Selective activation of drugs by redox processes. Plenum Press, New York, N.Y.
6. Edwards, D. I. 1993. Nitroimidazole drugs-action and resistance mechanisms. I. Mechanisms of action. J. Antimicrob. Chemother. 31:9-20.
7. Gorrell, T. E., N. Yarlett, and M. Muller. 1984. Isolation and characterization of Trichomonas vaginalis ferredoxin. Carlsberg Res. Commun. 49:259-268.
8. Hansch, C., A. Leo, and D. Hoekman. 1995. Exploring QSAR - hydrophobic, electronic, and steric constants. American Chemical Society, Washington, D.C.
9. Jacobson, B. L., Y. K Chae, J. L. Markley, I. Rayment, and H. M. Holden. 1993. Molecular structure of the oxidized, recombinant heterocyst [2Fe-2S] ferredoxin from Anabaena 7120 determined to 1.7 Å resolution. Biochemistry 32:6788-6793.
10. Lindmark, D. G., and M. Muller. 1974. Reduction of metronidazole by homogenates of trichomonad flagellates. J. Protozool. 21:436-440.
11. Liu, S. M., D. M. Brown, P. O'Donoghue, P. Upcroft, and J. A. Upcroft. 2000. Ferredoxin Involvement in metronidazole resistance of Giardia duodenalis Mol. Biochem. Parasitol. 108:137-140.
12. Marcus, R. A. 1956. On the theory of oxidation-reduction reactions involving electron transfer. J. Chem. Phys. 24:966-978.
13. Miller, M. W., H. L. Howes, R. V. Kasubick, and A. R. English. 1970. Alkylation of 2-methyl-5-nitroimidazole. Some potent antiprotozoal agents. J. Med. Chem. 13:849-852.
14. Moreno, S. N. J., R. P. Mason, P. A. Muniz, F. S. Cruz, and R. Docampo. 1983. Generation of free radicals from metronidazole and other nitroimidazoles by Tritrichomonas foetus. J. Biol. Chem. 258:4051-4054.
15. Muller, M., and T. E. Gorrell. 1983. Metabolism and metronidazole uptake in Trichomonas vaginalis isolates with different metronidazole susceptibilities. Antimicrob. Agents Chemother. 24:667-683.
16. Plant, C. W., and D. I. Edwards. 1976. The effect of tinidazole, metronidazole, and nitrofurazone on nucleic acid synthesis in Clostridium bifermentans. J. Antimicrob. Chemother. 2:203-209.
17. Quon, D. V. K., C. E. D'Oliveira, and P. J. Johnson. 1992. Reduced transcription of the ferredoxin gene in metronidazole-resistant Trichomonas vaginalis. Proc. Natl. Acad. Sci. USA 89:4402-4406.
18. Rypniewski, W. R., D. R. Breiter, M. M. Benning, G. Wesenberg, B. H. Oh, J. L. Markley, I. Raymet, and H. M. Holden. 1991. Crystallization and structure determination to 2.5 Å resolution of the oxidized [2Fe-2S] ferredoxin isolated from Anabaena 7120. Biochemistry 30:4126-4131.
19. + nitroreductase gene. J. Bacteriol. 182:5091-5096.
20. Tetley, R. M., and N. I. Bishop. 1979. The differential action of metronidazole on nitrogen fixation, hydrogen metabolism, photosynthesis and respiration in Anabaena and Scendesmus. Biochim. Biophys. Acta 546:43-53.
21. Tollin, G., L. K. Hanson, M. Caffrey, T. E. Meyer, and M. A. Cusanovich. 1986. Redox pathways in electron-transfer proteins: correlations between reactivities, solvent exposure, and unpaired-spin-density distributions. Proc. Natl. Acad. Sci. USA 83:3693-3697.
22. Vidakovic, M., G. Fraczkiewicz, and J. P. Germanas. 1996. Expression and spectroscopic characterization of the hydrogenosomal [2Fe-2S] ferredoxin from the protozoan Trichomonas vaginalis. J. Biol. Chem. 271:14734-14739.
23. Vidakovic, M., G. Fraczkiewicz, B. C. Dave, R. S. Czernuszewicz, and J. P. Germanas. 1995. The environment of [2Fe-2S] clusters in ferredoxins: the role of residue 45 probed by site-directed mutagenesis and spectroscopic analysis. Biochemistry 34:13906-13911.
24. Vidakovic, M., and J. P. Germanas. 1996. Electrostatic effects in electron transfer reactions of [2Fe-2S] ferredoxins with inorganic reagents. Protein Sci. 5:1793-1799.
25. Wassmann, C., A. Hellberg, E. Tannich, and I. Bruchhaus. 1999. Metronidazole resistance in the protozoan parasite Entamoeba histolytica is associated with increased expression of iron-containing superoxide dismutase and peroxiredoxin and decreased expression of ferredoxin 1 and flavin reductase. J. Biol. Chem. 274:26051-26056.
26. Yarlett, N., T. E. Gorrell, R. Marczak, and M. Muller. 1985. Reduction of nitroimidazole derivatives by hydrogenosomal extracts of Trichomonas vaginalis. Mol. Biochem. Parasitol. 14:29-40.