Enzymatic redox properties of novel nitrotriazole explosives implications for their toxicity

Zeitschrift fur Naturforschung - Section C Journal of Biosciences

Volumn 59, Issue 5-6, 2004, Pages 399-404

  Šarlauskas, Jonas ^a   Nemeikaite Čeniene, Aušra ^a   Anusevičius, Žilvinas ^a   Misevičiene, Lina ^a   Maroziene, Audrone ^a   Markevičius, Arvydas ^a   Čenas, Narimantas ^a  

^a VILNIUS UNIVERSITY   (Lithuania)

Author keywords

Cytotoxicity; Hemoglobin; Nitroaromatic Explosives; Oxidative Stress

Indexed keywords

BOS TAURUS; BOVINAE; BOVINE LEUKEMIA VIRUS; ENTEROBACTER; ENTEROBACTER CLOACAE; LAMB; MAMMALIA;

EID: 3042804031     PISSN: 09395075     EISSN: None     Source Type: Journal    
DOI: 10.1515/znc-2004-5-620     Document Type: Article

References (24)

1. Čėnas N., Nemeikaitė-Čėnienė A., Sergedienė E., Nivinskas H., Anusevičius Ž., and Šarlauskas J. (2001), Quantitative structure-activity relationships in enzymatic single-electron reduction of nitroaromatic explosives: implications for their cytotoxicity. Biochim. Biophys. Acta 1528, 31-38.
2. Cossum P. A. and Rickert D. E. (1987), Metabolism and toxicity of dinitrobenzene isomers in erythrocytes from Fischer-344 rats, Rhesus monkeys and humans. Toxicol. Lett. 37, 155-163.
3. Dilley J. V., Tyson C. A., Spangoord R. J., Sasmore D. P., Newell G. W., and Decre J. C. (1982), Short-term oral toxicity of 2,4,6-trinitrotoluene in mice, rats, and dogs. J. Toxicol. Environ. Health 9, 565-585.
4. Djerassi L. (1998), Hemolytic crisis in G6P-deficient individuals in the occupational setting. Int. Arch. Occup. Environ. Health 71, 26-28.
5. Facchini V. and Griffiths L. A. (1981), The involvement of the gastro-intestinal microflora in nitrocompound-induced methaemoglobinaemia in rats and its relationship to nitro group reduction. Biochem. Pharmacol. 30, 931-935.
6. Homma-Takeda S., Hiraka Y., Ohkuma Y., Oikawa S., Murata M., Ogawa K., Iwamuro T. L. S., Sun G. F., Kumagai Y., Shimojo N., and Kawanishi S. (2002), 2,4,6-Trinitrotoluene-induced reproductive toxicity via oxidative DNA damage by its metabolite. Free Rad. Res. 36, 555-566.
7. Knox R. J., Friedlos F., and Boland M. P. (1993), The bioactivation of CB 1954 and its use as a prodrug in antibody-directed enzyme prodrug therapy (AD-EPT). Cancer Metastasis Rev. 12, 195-212.
8. Koder R. L. and Miller A.-F. (1998), Steady-state kinetic mechanism, stereospecificity, substrate and inhibitor specificity of Enterobacter cloacae nitroreductase. Biochim. Biophys. Acta 1387, 395-405.
9. Kong L. Y., Jiang Q. C., and Qu Q. S. (1989), Formation of superoxide radical and hydrogen peroxide enhanced by trinitrotoluene in rat liver, brain, kidney, and testicle in vitro and in monkey liver in vivo. Biomed. Environ. Sci. 2, 72-77.
10. Le Campion L., Vandais A., and Ouzzani J. (1999), Microbial remediation of NTO in aqueous industrial wastes. FEMS Microbiol. Lett. 176, 197-203.
11. Leung K. H., Yao M., Stearns R., and Chiu S.-H. L. (1995), Mechanism of bioactivation and covalent binding of 2,4,6-trinitrotoluene. Chem.-Biol. Interact. 97, 37-51.
12. London J. O. and Smith D. M. (1985), A toxicological study of NTO. Los Alamos National Laboratory Report LA-10533-MS.
13. Marozienė A., Kliukienė R., Šarlauskas J., and Čėnas N. (2001), Methemoglobin formation in human erythrocytes by nitroaromatic explosives. Z. Naturforsch. 56c, 1157-1163.
14. Nivinskas H., Koder R. L., Anusevičius Ž., Šarlauskas J., Miller A.-F., and Čėnas N. (2001), Quantitative structure-activity relationships in two-electron reduction of nitroaromatic compounds by Enterobacter cloacae NAD(P)H:nitroreductase. Arch. Biochem. Biophys. 385, 170-178.
15. Ollinger K. and Brunmark A. (1991), Effect of hydroxy substituent position on 1,4-naphthoquinone toxicity to rat hepatocytes. J. Biol. Chem. 266, 21496-21503.
16. Orna M. V. and Mason R. P. (1989), Correlation of kinetic parameters of nitroreductase enzymes with redox properties of nitroaromatic compounds. J. Biol. Chem. 264, 12379-12384.
17. Prochaska H. J. (1988), Purification and crystallization of rat liver NAD(P)H:(quinone-acceptor) oxidore-ductase by cibacron blue affinity chromatography: identification of a new and potent inhibitor. Arch. Biochem. Biophys. 267, 529-538.
18. + reductase, ferredoxin and flavodoxin from a single batch of the cyanobacterium Anabaena PCC7119. Prep. Biochem. 21, 191-204.
19. Riefler R. G. and Smets B. F. (2000), Enzymatic reduction of 2,4,6-trinitrotoluene and related nitroarenes: kinetics linked to one-electron redox potentials. Environ. Sci. Technol. 34, 3900-3906.
20. Sabbioni G. and Jones C. R. (2002), Biomonitoring of arylamines and nitroarenes. Biomarkers 7, 347-421.
21. Sikder A. K., Geetha M., Sarwade D. B., and Agrawal J. P. (2001), Studies on characterization and thermal behaviour of 3-amino-5-nitro-1,2,4-triazole and its derivatives. J. Hazard. Mat. A82, 1-12.
22. Wardman P. (1989), Reduction potentials of one-electron couples involving free radicals in aqueous solution. J. Phys. Chem. Ref. Data 18, 1637-1755.
23. Winterbourn C. C. (1985), Reactions of superoxide with hemoglobin. In: CRC Handbook of Methods for Oxygen Radical Research (R. A. Greenwald, ed.). CRC Press Inc., Boca Raton, FL, pp. 137-141.
24. Yasukochi Y. and Masters B. S. S. (1976), Some properties of a detergent-solubilized NADPH-cytochrome c (cytochrome P-450) reductase purified by biospecific affinity chromatography. J. Biol. Chem. 251, 5337-5334.