In vitro degradation of hexanitrohexaazaisowurtzitane (CL-20) by cytosolic enzymes of Japanese quail and the rabbit

Environmental Toxicology and Chemistry

Volumn 25, Issue 12, 2006, Pages 3221-3229

  Bardai, Ghalib K ^a,b   Halasz, Annamaria ^a   Sunahara, Geoffrey I ^a   Dodard, Sabine ^a   Spear, Philip A ^b   Grosse, Stephan ^a   Hoang, Johnston ^a   Hawari, Jalal ^a  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

^b UNIVERSITÉ DU QUÉBEC À MONTRÉAL   (Canada)

Author keywords

Biotransformation; Embryo; Explosives; Glutathione S transferase; Japanese quail

Indexed keywords

BIOTRANSFORMATIONS; GLUTATHIONE-S-TRANSFERASE; INTERMEDIATE METABOLITES; JAPANESE QUAIL;

BIODIVERSITY; DEGRADATION; ENZYMES; HEALTH RISKS; LIQUID CHROMATOGRAPHY; PROPELLANTS;

EXPLOSIVES;

ETACRYNIC ACID; EXPLOSIVE; GLUTATHIONE DERIVATIVE; GLUTATHIONE TRANSFERASE; HEXANITROHEXAAZAISOWURTZITANE; NITRITE; PROPELLANT; S OCTYLGLUTATHIONE; UNCLASSIFIED DRUG;

BIODEGRADATION; BIOTRANSFORMATION; CHLOROBENZENE; EMBRYO; ENZYME; EXPLOSIVE; GAMEBIRD; LAGOMORPH; MAMMAL; NEMATODE;

ANIMAL TISSUE; ARTICLE; BIOTRANSFORMATION; CONTROLLED STUDY; DEGRADATION; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME PURIFICATION; FEMALE; LIQUID CHROMATOGRAPHY; LIVER CYTOSOL; LIVER METABOLISM; MASS SPECTROMETRY; MOLECULAR WEIGHT; NONHUMAN; PRIORITY JOURNAL; QUAIL; RABBIT;

AMINO ACID SEQUENCE; ANIMALS; AZA COMPOUNDS; CARBON; COTURNIX; CYTOSOL; ENZYME INHIBITORS; GLUTATHIONE TRANSFERASE; HETEROCYCLIC COMPOUNDS; LIVER; MOLECULAR CONFORMATION; MOLECULAR SEQUENCE DATA; RABBITS; TIME FACTORS;

ANIMALIA; COTURNIX; COTURNIX JAPONICA; ORYCTOLAGUS CUNICULUS; PHASIANIDAE;

EID: 33846264569     PISSN: 07307268     EISSN: None     Source Type: Journal    
DOI: 10.1897/06-068R.1     Document Type: Article

References (37)

1. Dodard S, Sunahara GI, Sarrazin M, Gong P, Kuperman RG, Ampleman G, Thiboutot S, Hawari J. 2005. Survival and reproduction of enchytraeid worms (Oligochaeta) in different soil types amended with cyclic nitramine explosives. Environ Toxicol Chem 24:2579-2587.
2. Robidoux PY, Sunahara GI, Savard K, Berthelot Y, Dodard S, Martel M, Gong P, Hawari J. 2004. Acute and chronic toxicity of the new explosive CL-20 to the earthworm (Eisenia andrei) exposed to amended natural soils. Environ Topical Chem 23: 1026-1034.
3. Gong P, Sunahara GI, Rocheleau S, Dodard SG, Robidoux PY, Hawari J. 2004. Preliminary ecotoxicological characterization of a new energetic substance, CL-20. Chemosphere 56:653-658.
4. Bardai GK, Sunahara GI, Spear PA, Martel M, Gong P, Hawari J. 2005. Effects of dietary administration of CL 20 on the Japanese quail (Coturnix coturnix japonica). Arch Environ Contain Toxicol 49:215-222.
5. Armstrong RN. 1997. Structure, catalytic mechanism, and evolution of the glutathione transferases. Chem Res Toxicol 10:2-18.
6. Eaton DL, Bammler TK. 1999. Concise review of the glutathione-S- transferases and their significance to toxicology. Toxicol Sci 49:156-164.
7. Chasseaud LF. 1979. The role of glutathione and glutathione-S- transferases in the metabolism of chemical carcinogens and other electrophilic agents. Adv Cancer Res 29:175-274.
8. Jakoby WB. 1978. The glutathione-S-transferases: A group of multifunctional detoxification proteins. Adv Enzymol Relat Areas Mol Biol 46:383-414.
9. Dai HQ, Edens FW, Roe MR. 1996. Glutathione-S-transferase in the Japanese quail: Tissue distribution and purification of the liver isozymes. J Biochem Toxicol 11:85-96.
10. Lammeli UK. 1970. Cleavage of structural proteins during the assembly of the head of the bacteriophage T4. Nature 227:580-685.
11. Bhushan B, Halasz A, Hawari J. 2005. Biotransformation of CL-20 by a dehydrogenase enzyme from Clostridium sp. EDB2. Appl Microbiol Biotech 70:4040-4047.
12. Habig WH, Pabst MJ, Jakoby WB. 1974. Glutathione-S-transferases: The first enzymatic step in mercapturic acid formation. J Biol Chem 249:7130-7139.
13. Okemgbo AA, Hill HH, Metcalf SG, Bachelor MA. 1999. Determination of nitrate and nitrite in Hanford defense waste by reverse-polarity capillary zone electrophoresis. J Chromatogr A 844:387-394.
14. Balakrishnan VK, Halasz A, Hawari J. 2003. Alkaline hydrolysis of the cyclic nitramine explosives RDX, HMX, and CL-20: New insights into degradation pathways obtained by the observation of novel intermediates. Environ Sci Technol 37:1838-1843.
15. Hissin PJ, Hilf R. 1976. A fluorometric method for determination of oxidized and reduced glutathione in tissues. Anal Biochem 74: 214-226.
16. Bhushan B, Halasz A, Hawari J. 2004. Nitroreductase catalyzed biotransformation of CL-20. Biochem Biophys Res Commun 322: 271-276.
17. Balakrishnan V, Monteil-Rivera F, Halasz A, Hawari J. 2004. Decomposition of the polycyclic nitramine explosive, CL-20, by Fe(0). Environ Sci Technol 38:6861-6866.
18. Bhushan B, Paquet L, Spain JC, Hawari J. 2003. Biotransformation of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20) by denitrifying Pseudomonas sp. strain FA1. Appl Environ Microbiol 69:5216-5221.
19. Cameron AD, Sinning I, L'Hermite G, Olin B, Board PG, Mannervik B, Jones JA. 1995. Structural analysis of human alpha-class glutathione transferase in the apo-form and in complexes with ethacrynic acid and its glutathione conjugate. Structure 3: 717-727.
20. Poleman JHTM, van Ommen B, Bogaards JPP, van Bladeren PJ. 1993. Ethacrynic acid and its glutathione conjugates as inhibitors of glutathione-S-transferases. Xenobiotica 23:913-923.
21. Schultz M, Dutta S, Tew KD. 1997. Inhibitors of glutathione-S- transferases as therapeutic agents. Adv Drug Deliv Rev 26:91-104.
22. Chang L-H, Chuang LF, Tsai CP, Tu CPD, Tam MF. 1990. Characterization of glutathione-S-transferases from day-old chick livers. Biochemistry 29:744-750.
23. Hsieh C-H, Liu L-F, Tsai C-P, Tam MF. 1999. Characterization and cloning of avian-hepatic glutathione-S-transferases. Biochem J 343:87-93.
24. Yeung TC, Gidari AS. 1980. Purification and properties of a chicken liver glutathione-S-transferase. Arch Biochem Biophys 205:404-411.
25. Bhushan B, Halasz A, Spain JC, Hawari J. 2004. Initial reaction(s) in biotransformation of CL-20 is catalyzed by salicylate 1-mono-oxygenase from Pseudomonas sp. Strain ATCC 29352. Appl Environ Microbiol 70:4040-4047.
26. Matés JM, Pérez-Gómez C, Blanca M. 2000. Chemical and biological activity of free radical "scavengers" in allergic diseases. Clin Chim Acta 296:1-15.
27. Meister A, Anderson ME. 1983. Glutathione. Annu Rev Biochem 52:711-760.
28. Cenas N, Anusevicius Z, Nivinskas H, Miseviciene L, Sarlauskas J. 2004. Structure-activity relationships in two-electron reduction of quinones. Methods Enzymol 382:258-277.
29. Sarlauskas J, Nemeikaite-Ceniene A, Anusevicius Z, Miseviciene L, Julvez MM, Medina M, Gomez-Moreno C, Cenas N. 2004. Flavoenzyme-catalyzed redox cycling of hydroxylamino- and amino metabolites of 2,4,6-trinitrotoluene: Implications for their cytotoxicity. Arch Biochem Biophys 425:184-192.
30. Ogawa NO, Hirose T, Tsukamoto M, Fukushima K, Suwa T, Satoh T. 1995. GSH-independent denitration of organic nitrate esters in rabbit hepatic cytosol and vascular cytosol. Res Commun Mol Pathol Pharmacol 88:153-161.
31. Ogawa NO, Hirose T, Tsukamoto M, Fukushima K. Suwa T, Satoh T. 1995. Purification and characterization of glutathione-independent denitration enzyme of organic nitrate esters in rabbit hepatic cytosol. Biol Pharm Bull 18:1352-1355.
32. Odani H, Shinzato T, Usami J, Matsumoto Y, Brinkmann Frye E, Baynes JW, Maeda K. 1998. Imidazolium crosslinks derived from reaction of lysine with glyoxal and methylglyoxal are increased in serum proteins of uremia patients: Evidence for increased oxidative stress in uremia. FEBS Lett 427:381-385.
33. Dieckhaus CM, Fernandez-Metzler CL, King R, Krolikowski PH, Baillie TA. 2005. Negative ion tandem mass spectrometry for the detection of glutathione conjugates. Chem Res Toxicol 18:630-638.
34. Hochachka PW, Somero GN. 1984. Biochemical Adaptation. Princeton University Press, Princeton, NJ, USA.
35. DeSesso JM, Jacobson CF, Scialli AR, Goeringer GC. 2000. Hydroxy lamine moiety of developmental toxicants is associated with early cell death: A structure-activity analysis. Teratology 62:346-355.
36. Yoshizaki N, Soga M, Ito Y, Mao KM, Sultana S, Yonezawa S. 2004. Two-step consumption of yolk granules during the development of quail embryos. Dev Growth Differ 46:229-238.
37. DeBruin WC, Te Morsche RH, Wagenmans MJ, Alferink JC, Townsend AJ, Wieringa B, Peters WH. 1998. Identification of a novel murine glutathione-S-transferase class mu gene. Biochem J 330:623-626.