Catalytic Bioscavengers Against Toxic Esters, an Alternative Approach for Prophylaxis and Treatments of Poisonings

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Abstract


Bioscavengers are biopharmaceuticals that specifically react with toxicants. thus, enzymes reacting with poisonous esters can be used as bioscavengers for neutralization of toxic molecules before they reach physiological targets. Parenteral administration of bioscavengers is, therefore, intended for prophylaxis or pre-treatments, emergency and post-exposure treatments of intoxications. these enzymes can also be used for application on skin, mucosa and wounds as active components of topical skin protectants and decontamination solutions. Human butyrylcholinesterase is the first stoichiometric bioscavenger for safe and efficient prophylaxis of organophosphate poisoning. However, huge amounts of a costly enzyme are needed for protection. thus, the bioscavenger approach will be greatly improved by the use of catalytic bioscavengers. catalytic bioscavengers are enzymes capable of degrading toxic esters with a turnover. Suitable catalytic bioscavengers are engineered mutants of human enzymes. efficient mutants of human butyrylcholinesterase have been made that hydrolyze cocaine at a high rate. Mutants of human cholinesterases capable of hydrolyzing OPs have been made, but so far their activity is too low to be of medical interest. Human paraoxonase a promiscuous plasma enzyme is certainly the most promising phosphotriesterase. However, its biotechnology is still in its infancy. Other enzymes and proteins from blood and organs, and secondary biological targets of OPs and carbamates are potential bioscavengers, in particular serum albumin that reacts with OPs and self-reactivates. Lastly, non-human enzymes, phosphotriesterases and oxidases from various bacterial and eukaryotic sources could be used for external use against OP poisoning and for internal use after modifications for immunological compatibility.

1 . THE BIOSCAVENGER CONCEPT Potter and Wadkins, 2006; Satoh and Hosokawa, 2006) in the enzyme systems located in skin, blood organs are involved in metabolism of drugs and xenobiotics is well known. the imnatural defences against endogenous and exogenous poisons. portance of plasma esterases in the inactivation of numerous Detoxification processes occur through different types of re-toxicants has been recognized, too. Lastly, there is growing actions, including oxidation, hydrolysis, and conjugation. the evidence that catalytic antibodies play also an efficient role role of liver, lung and kidney enzymes, cytochromes P450 in scavenging deleterious molecules and radicals (Belogurov (Brown et al., 2008), oxidases, transferases (Miners et al., et al., 2009). these multiple enzymes constitute cellular and 2006), amido-carboxylesterases (redinbo and Potter, 2005; circulating barriers that protect physiological machineries and systems against specific toxicants. Here we will examine endogenous and exogenous enzymes that react with poisonous carboxylic-, organophosphoryl- and carbamyl-esters. these enzymes act either as stoichiometric bioscavengers or catalytic bioscavengers. catalytic bioscavengers are biocatalysts capable of degrading poisonous compounds with a turnover. enzymes that are potential catalytic bioscavengers will be reviewed.

Patrick Masson

Centre de Recherches du Service de Santé des Armées, Toxicology department; Institute of Structure Biology, Molecular Biophysics Laboratory

Email: pmasson@unmc.edu
La Tronche, France; Grenoble, France; Grenoble, France

Daniel Rochu

Centre de Recherches du Service de Santé des Armées, Toxicology department; Bundeswehr Institute of Toxicology and Pharmacology

Munich, Germany

  1. Aas, P. (2003) Prehosp. Disast. Med. V18, P208.
  2. Afriat, L., Roodveldt, C., Manco, G., and Tawfik, D.S. (2006) Biochemistry V45, P13677.
  3. Albuquerque, E.X., Pereira, E.F.R., Aracava, Y., Fawcett, W.P., Oliveira, M., Randal, W.R., Hamilton, T.A., Kan, R.K., Romano, J.A., Jr., and Adler, M. (2006) Proc. Natl. Acad. Sci. USA V103, P13220.
  4. Amitai, G., Adani, R., Sod-Moriah, I., Rabinovitz, A., Vincze, H., Leader, H., Chefetz, B., Leibovitz-Persky, L., Friesem, D., and Hadar, Y. (1998) FEBS Lett. V438, P195.
  5. Amitai, G., Adani, R., Hershkovitz, M., Bel, P., Rabinovitz, I., and Meshulam, H. (2003) J. Appl. Toxicol. V23, P225.
  6. Amitai, G., Gaidukov, L., Adani, R., Yishay, S., Yacov, G., Kushnir, M., Teitlboim, S., Lindenbaum, M., Bel, P., Khersonsky, O., Tawfik, D.S., and Meshulam, H. (2006) FEBS J. V273, P1906.
  7. Amitai, G., Gupta, R.D., and Tawfik, D.S. (2007) HFSP J. V1, P67.
  8. Ashani, Y., Leader, H., Rothschild, N., and Dosoretz, C. (1998) Biochem. Pharmacol. V55, P159.
  9. Ashani, Y., and Pistinner, S. (2004) Toxicol. Sci. V77, P358.
  10. Aubert, S.D., Li, Y., and Raushel, F.M. (2004) Biochemistry V43, P5707.
  11. Belogurov, A., Kozyr, A., Ponomarenko, N. and Gabibov, A. (2009) BioAssays, in press.
  12. Benning, M.M., Kuo, J.M., Raushel, F.M., and Holden, H.M. (1994) Biochemistry V33, P15001.
  13. Bershtein, S., and Tawfik, D.S. (2008) Curr. Opin. Chem. Biol. V12, P151.
  14. Bird, S.B., Sutherland, T.D., Gresham, C., Oakeshott, J., Scott, C. and Eddleston, M. (2008) Toxicology V247, P88.
  15. Blum, M.-M., Lohr, F., Richardt, A., Ruterjans, H., and Chen, J.C.-H. (2006) J. Am. Chem. Soc. V128, P12750.
  16. Bradshaw, G., Gutierrez, A., Miyake, J.H., Davis, K.R., Li, A.C., Glass, C.K., Curtiss, L.K., and Davis, R.A. (2005) Proc. Natl. Acad. Sci. USA V102, P11029.
  17. Braue, E.H., Hobson, S.T., Govardhan, C., and Khalaf, N. (2002) U.S. Patent n° US 6,410,604 B1, Jun. 25.
  18. Brimijoin, S., Gao, Y., Anker, J., Gliddon, L.A., LaFleur, D., Shah, R., Zhao, Q., Singh, M. and Carroll, M.E. (2008) Neuropsychopharmacol. V33, P2715.
  19. Brown, C.M., Reisfeld, B. and Mayeno, A.N. (2008) Drug Metab. Rev. V40, P1.
  20. Carletti, E., Li, H., Li, B., Ekstrom, F., Nicolet, Y., Loiodice, M., Gillon, E., Froment, M.T., Lockridge, O., Schopfer, L.M., Masson, P. and Nachon, F. (2008) J. Am. Chem. Soc. V130, P16011.
  21. Carletti, E., Jacquamet, L., Loiodice, M., Rochu, D., Masson, P., and Nachon, F. (2009) J. Enz. Inhib. Med. Chem., in press
  22. Casida, J.E., and Quistad, G.B. (2004) Chem. Res. Toxicol. V17, P983.
  23. Chen, S.-L., Fang, W.-H., and Himo, F. (2007) J. Phys. Chem. B. V111, P1253.
  24. Chen, W., and Mulchandani, A. (1998) TIBTECH, V16, P71.
  25. Cheng, T-C., Harvey, S.P., and MacKenzie, A. (1994) in: Proceedings of the 1993 ERDEC Scientific Conference on Chemical Defense Research AD-A286742, P955.
  26. Cheng, T-C., DeFrank, J.J., and Rastogi, V.K. (1999) Chem.-Biol. Interact. V119-120, P455.
  27. Chilukuri, N., Sun, W., Naik, R.S., Parikh, K., Tang, L., Doctor, B. and Saxena, A. (2008) Chem. Biol-Interact. V175, P255.
  28. Chilukuri, N., Duysen, E.G., Parikh, K., Sun, W., Doctor, B.P., Lockridge, O. and Saxena, A. (2008) Chem.-Biol. Interact. V175, P327.
  29. Chitlaru, T., Kronman, C., Zeevi, M., Kam, A., Harel, A., Ordentlich, A., Velan, B., and Shafferman, A. (1998) Biochem J. V336, P647.
  30. Clery-Barraud, C., Renault, F., Leva, J., El Bakdouri, N., Masson, P., and Rochu, D. (2009) Biochim. Biophys. Acta, in press.
  31. Cohen, O., Kronman, C., Raveh, L., Mazor, O., Ordentlich, and A, Shafferman, A. (2006) Mol. Pharmacol. V70, P1121.
  32. Cohen, O., Kronman, C., Lazar, A., Velan, B., and Shafferman, A. (2007) J. Biol. Chem. V282, P35491.
  33. Costa, L.G., and Furlong, C.E. Eds. (2002). “Paraoxonase (PON1) In Health and Disease: Basic and Clinical Aspects”. Kluwer Academic Publishers, Dordrecht, The Netherlands.
  34. Costa, L.G. (2006) Clin. Chim. Acta V366, P1.
  35. Cowan, J., Sinton, C.M., Varley, A.W., Wians, F.H., Haley, R.W., and Munford, R.S. (2001) Toxicol. Appl. Pharmacol. V173, P1.
  36. Davis, H.G., Richter, R.J., Keifer, M., Broomfield, C.A., Sowalla J., and Furlong, C.E. (1996). Nature Genet. V14, P334.
  37. Dawson, R.M., Pantelidis, S., Rose, H.R., and Kotsonis, S.E. (2008) J. Hazard Mater. V157, P308.
  38. DeFranck, J.J., Beaudry, W.T., Cheng, T.C., Harvey, S.P., Stroup, A.N., and Szafraniec, L.L. (1993) Chem.-Biol. Interact. V87, P141.
  39. Deng, SX., Zhu, ZZ., Vinogradov, M., Macdonald, J., Stojanovic, MN. and Landry, DW. (2008) Bioscience Review 2008, Hunt Valley, MD, USA, June1-6. P6.
  40. Diemer, H., Elias, M., Renault, F., Rochu, D., Contreras-Martel, C., Schaeffer, C., Van Dorsselaer, A., and Chabriere E. (2008) Proteins. V71, P1708.
  41. Ding, S-J, Carr, J., Carlson,.E., Xue, W., Li, Y., Schopfer, L.M., Li, B., Nachon, F., Asojo, O., Thompson, C.M., Hinrichs, S.H., Masson, P., and Lockridge, O. (2008) Chem. Res. Toxicol. V21, P1787.
  42. Doctor, B.P., and Saxena, A. (2005) Chem.-Biol. Interact. V157-158, P167.
  43. Dumas, D.P., Durst, H.D., Landis, W.G., and Raushel, F.W. (1990) Arch. Biochem. Biophys. V277, P155.
  44. Eddelston, M., Buckley, N.A., Eyer, P., and Dawson, A.H. (2008) Lancet, V371, P597.
  45. Elias, M., Dupuy, J., Merone, L., Mandrich, L., Porzio, E., Moniot, S., Rochu, D., Lecomte C., Rossi, M., Masson, P., Manco, G., and Chabriere E. (2008) J.Mol. Biol, V379, P1017.
  46. Del Vecchio, P., Elias, M., Merone, L., Graziano, G., Dupuy, J., Mandrich, L., Carullo, P., Fournier, B., Rochu, D., Rossi, M., Masson, P., Chabriere E. and Manco, G. (2009). Extremophiles, in press.
  47. Eyer, P., Szinicz, L., Thiermann, H., Worek, F., and Zilker, T. (2007) Toxicology V233, P108.
  48. Feerer, M., Golyshina, O., Beloqui, A., and Golyshin, P.N. (2007) Current Opin. Microbiol. V10, P207.
  49. Fisher, S., Arad, A., and Margalit, R. (2005) Arch. Biochem. Biophys. V434, P108.
  50. Fleming, C.D., Edwards, C.E., Kirby, S.D., Maxwell, D.M., Potter, P.M., Cerasoli, D.M., and Redindo, M.R. (2007) Biochemistry V46, P5063.
  51. Fokine, A., Morales, R., Contreras-Martel, C., Carpentier, P., Renault, F., Rochu, D., and Chabriere, E. (2003) Acta Cryst. D V59, P2083.
  52. Fu, A.L., Wang, Y.X., and Sun, M.J. (2005) Biochem. Biophys. Res. Commun. V328, P901.
  53. Fujioka, K., and Casida, J.E. (2007) Chem. Res. Toxicol. V20, P1211.
  54. Gaidukov, L., and Tawfik, D.S. (2005) Biochemistry V44, P11843.
  55. Ghanem, E., and Raushel, F.M. (2005) Toxicol Appl. Pharmacol. V207, P459.
  56. Gill, I., and Ballesteros, A. (2000) Biotechnol. Bioeng. V70, P400.
  57. Gordon, R.C., Doctor, B.P., Saxena, A., Feaster, S.R., Maxwell, D., Ross, M., Lenz, D., Lejeune, K., and Russell, A. (2003) U.S. Patent n° US 6,642,037 B2, Nov. 4.
  58. Gregoriadis, G., Fernandes, A. and McCormack, B. (1999) S.T. P. Pharma Sci. V9, P61.
  59. Griffiths, A.D., and Tawfik, D.S. (2003) EMBO J. V22, P24.
  60. Grigoryan, H., Halebyan, G., Lefebvre, B., Brasme, B. and Masson, P. (2008) Biochim. Biophys. Acta, V1784, P1818.
  61. Guns, P.-J., Van Assche, T., Verreth, W., Fransen, P., Mackness, B., Mackness, M., Holvoet, P., and Bult, H. (2008) Brit. J. Pharmacol. V153, P508.
  62. Guven, M., Sungur, M., Eser, B., Sari, I., and Altuntas, F. (2004) Clin. Toxicol. V42, P617.
  63. Harel, M., Aharoni, A., Gaidukov, L., Brumshtein, B., Khersonsky, O., Meged, R., Dvir, H., Ravelli, R.B.G., McCarty, A., Toker, L., Silman, I., and Sussman, J. (2004) Nat. Struct. Mol. Biol. V11, P412.
  64. Hartlieb, J., and Ruterjans, H. (2001) Biochim. Biophys. Acta V1546, P312.
  65. Hill, C.M., Li, W.S., Thoden, J.B., Holden, H.M., and Raushel, F.M. (2003) J. Am. Chem. Soc. V125, P8990.
  66. Hoffman, R., Morasco, R. and Goldfrank, L. (1996) J Toxicol. Clin. Toxicol., V34, P259.
  67. Hoskin, F.C.G., Walker, J.E., Detbarn, W.D., and Wild, J.R. (1995) Biochem. Pharmacol. V49, P711.
  68. Hsu, Y-T., Su, C-Y., Du, H-C., Jao, S-C. and Li, W-S. (2008) Chem. Diversity V5, P1401.
  69. Lynch, T., Mattes, C., Singh, A., Bradley, R., Brady, R. and Dretchen, K. (1997) J. Appl. Pharmacol., V145, P363.
  70. Hu, X., Jiang, X., Lenz, D.E., Cerasoli, D.M., and Wallqvist, A. (2009) Proteins. In press.
  71. Huang,Y.J, HuangY., Baldassarre, H., Wang, B., Lazaris, A., Leduc, M., Bilodeau, A.S., Bellemare, A., Cote, M., Herskovits, P., Touati, M., Turcotte, C., Valeanu, L., Lemée, N., Wilgus, H., Begin, I., Bhatia, B., Rao, K., Neveu, N., Brochu, E., Pierson, J., Hockley, D.K., Cerasoli, D.M., Lenz, D.E., Karatzas, C.N., and Langermann, S. (2007) Proc. Natl. Acad. Sci. USA V104, P13603.
  72. Huang, Y.J., Lundy, P.M., Lazaris,A., Huang, Y., Baldassarre, H., Wang, B., Turcotte, C., Cote, M., Bellemare, A., Bilodeau, A.S., Brouillard, S., Touati, M., Herskovits, P., Begin, I., Neveu, N., Brochu, E., Pierson, J., Hockley, D.K., Cerasoli, D.M., Lenz, D.E., Wilgus, H., Karatzas, C.N., and Langermann, S. (2008) BMC Biotechnol. V8, P50.
  73. Inaba, T., Stewart, D.J. and Kalow, W. (1978) Clin. Pharmacol. Ther. V23, P547.
  74. Jarv, J. (1989) in “Enzymes hydrolysing organophosphorus compounds” (E. Reiner, W.N. Aldridge, and F.C.G. Hoskin, Eds.), Ellis Horwood Ltd, Chichester, UK, P221.
  75. Jackson, C.J., Foo, J.-L., Kim, H.-K., Carr, P.D., Liu, J.-W., Salem, G., and Ollis, D.L. (2008) J. Mol. Biol. V375, P1189.
  76. James, R.W., and Deakin, S.P. (2004) Free Rad. Biol. Med. V37, P1986.
  77. Josse, D., Xie, W., Renault, F., Rochu, D., Schopfer, L.M., Masson, P., and Lockridge, O. (1999) Biochemistry V38, P2816.
  78. Jovic, F., Louise, L., Mioskowski, C., and Renard, P.Y. (2005) Tetrahedron Lett. V46, P6809.
  79. Jun, D., Kuca K., Bajgar, J., Hruby, M., Kucka, J., Renault, F., and Masson, P. (2007) Toxicology, V233, P235.
  80. Jun, D., Musilova, L., Nachon, F., Rochu, D., Renault, F., Masson, P. (2008) Bioscience Review Meeting 2008, Hunt Valley, MA, USA, 1-6 June 2008.
  81. Kaliste-Korhonen, E., Tuovinen, K., and Haninen, O. (1996) Hum. Exp. Toxicol. V15, P972.
  82. Karnati, C., Du, H., Ji, H.-F., Xu, X., Lvov, Y., Mulchandani, A., Mulchandani, P., and Chen, W. (2007) Biosens. Bioelectron. V22, P2636.
  83. Katsemi, V., Lucke, C., Koepke, J., Lohr, F., Maurer, S., Fritzsch, G., and Ruterjans, H. (2005) Biochemistry V44, P9022.
  84. Khersonsky, O., and Tawfik, D.S. (2005) Biochemistry V44, P6371.
  85. Khersonsky, O., and Tawfik, D.S. (2006) J. Biol. Chem. V281, P7649.
  86. Kovarik, Z., Radic, Z., Berman, H.A., and Taylor, P. (2007) Toxicology V233, P79.
  87. Kovarik, Z.,Calić, M., Sinko, G., Bosak, A., Berend, S., Vrdoljak, A.L., and Radić, B. (2008) Chem.-Biol. Interact. V175, P173.
  88. Kronman, C., Velan, B., Marcus, D., Ordentlich, A. Reuveny, S., and Shafferman, A. (1995) Biochem. J. V311, P959.
  89. Kronman, C., Chitlaru, T., Elhanany, E., Velan, B., and Shafferman, A. (2000) J. Biol. Chem. V275, P29488.
  90. Kronman, C., Cohen, O., Raveh, L., Mazor, O., Ordentlich, A., and Shafferman, A. (2007) Toxicology V233, P40.
  91. Kuo, J.N., Chae, M.Y., and Raushel, F.M. (1997) Biochemistry V36, P1982.
  92. La Du, B.N. (1996) Nature Med. V2, P1186.
  93. Lai, K., Stolowich, N.J., and Wild, J.R. (1995) Arch. Biochem. Biophys. V318, P59.
  94. Landry, D.W., Zhao, K., Yang, G. X. Q., Glickman, M. and Georgiadis, T.M. (1993) Science, V259, P1899.
  95. Landry, D.W., and Deng, S.X. (2006) United States Patent № 20060216778.
  96. Larsen, N.A., de Prada, P., Deng, S.X., Mittal, A., Braskett, M., Zhu, X., Wilson, I.A. and Landry, D.W. (2004) Biochemistry, V43, P8067.
  97. Letant, S.E., Kane, S.R., Hart, B.R., Hadi, M.Z., Cheng, T.-C., Rastogi, V.K., and Reynolds, J.G. (2005) Chem. Commun. V7, P851.
  98. Lejeune, K.E., and Russell, A. J. (1999) Biotechnol. Bioengn. V62, P659.
  99. Lenz, D.E., Broomfield, C.A., Yeung, D.T., Masson, P., Maxwell, D.M., and Cerasoli, D.M. (2007) in “Chemical warfare agents: chemistry, pharmacology and therapeutics” (J.A. Romano, B. Luckey, and H. Salem Eds), CRC Press, Boca Raton, P175.
  100. Li, B., Sedlacek, M., Manoharan, I., Boopathy, R., Duysen, E.G., Masson, P. and Lockridge, O. (2005) Biochem. Pharmacol. V70, P1673.
  101. Li, B., Duysen, E.G., Poluektova, L.Y., Murrin, L.C., and Lockridge, O. (2006) Toxicol. Appl. Pharmacol. V214, P152.
  102. Li, H., Schopfer, L.M., Nachon, F., Froment, M-T., Masson, P., and Lockridge, O. (2007) Toxicol. Sci. V100, P136.
  103. Li, B., Nachon, F., Froment, M.T., Verdier, L., Debouzy, J.C., Brasme, B., Gillon, E., Schopfer, L.M., Lockridge, O., and Masson, P. (2008) Chem. Res. Toxicol. V21, P421.
  104. Lockridge, O. (1990) Pharmac. Ther. V47, P35.
  105. Lockridge, O., Blong, R.M., Masson, P., Millard, C.B., and Broomfield, C.A. (1997) Biochemistry V36, P786.
  106. Lockridge, O., Duysen, E. G. and Masson, P. (2009) In: Anticholinesterase pesticides: metabolism, neurotoxicity, and epidemiology, (Satoh, T. and Gupta, R.C., Eds), Elsevier, in press.
  107. Lundy, P.M., Raveh, L., and Amitai, G. (2006) Toxicol. Rev. V25, P1.
  108. Lynch, T., Mattes, C., Singh, A., Bradley, R., Brady, R. and Dretchen, K. (1997) Toxical. Appl. Pharmacol., V145, P363.
  109. Mackness, B., Mackness, M., Aviram, M., and Paragh, G. Eds. (2008) “The paraoxonase: their role in disease development and xenobiotic metabolism”. Springer, Dordrecht, The Netherlands.
  110. McKenzie, K.M., Mee, J.M., Rogers, C.J., Hixon, M.S., Kaufmann, G.F. and Janda, K.D. (2007) J. Mol. Biol. V365, P722.
  111. Masson, P., Josse, D., Lockridge, O., Viguie, N., Taupin, C., and Buhler, C. (1998) J. Physiol. V92, P357.
  112. Masson, P. Clery, C., Guerra, P., Redslob, A., Albaret, C., and Fortier, P-L. (1999) Biochem. J. V343, P361.
  113. Masson, P., Froment, M.T., Gillon, E., Nachon, F., Lockridge, O., and Schopfer, L.M. (2007) Biochim. Biophys. Acta V1774, P16.
  114. Masson, P., Nachon, F., Broomfield, C.A., Lenz, D.E., Verdier, L., Schopfer, L.M., and Lockridge, O. (2008) Chem.-Biol. Interact. V.175, P.273.
  115. Maturano, M.D., Bongibault, V., Willson, M., Klaebe, A., and Fournier, D. (1997) Tetrahedron V53, P17241.
  116. Maxwell, D.M., Brecht, K.M., Koplovitz, I., and Sweeney, R.E. (2006) Arch. Toxicol. V80, P756.
  117. Mazor, O., Cohen, O., Kronman, C., Raveh, L., Stein, D., Ordentlich, A. and Shafferman, A. (2008) Mol. Pharmacol. V74, P755.
  118. McDaniel, C.S., McDaniel, J., Wales, M.E., and Wild, J.R. (2006) Prog. Organ. Coatings V55, P182.
  119. Merone, L., Mandrich, L., Rossi, M., and Manco G. (2005) Extremophiles V9, P297.
  120. Millard, C.B., Lockridge, O., and Broomfield, C.A. (1995) Biochemistry V34, P15925.
  121. Millard, C.B., Lockridge, O., and Broomfield, C.A. (1999) Biochemistry V37, P237.
  122. Miners, J.O., Knights, K.M., Houston, J.B. and Mackenzie, P.L. (2006) Biochem. Pharmacol. V71, P1531.
  123. Miyoshi, M., Nakano, Y., Sakagushi, T., Ogi, H., Oda, N., Suenari, K., Kiyotani, K., Ozono, R., Oshima, T., Yoshida, T., and Chayama, K. (2007) Hypertens. Res. V30, P85. Morales, R., Berna, A., Carpentier, P., Contreras-Martel, C., 124. Renault, F., Nicodeme, M., Chesne-Seck, M.-L. Bernier, F., Schaeffer, C., Diemer, H., Van-Dorsselaer, A., Fontecilla-Camps, J.C., Masson, P., Rochu, D., and Chabriere, E. (2006) Structure V14, P601.
  124. Moriarty, L.M., Lally, M.N., Carolan, C.G., Jones, M., Clancy, J.M. and Gilmer, J.F. (2008) J. Med. Chem. V51, P7991.
  125. Nachon, F., Asojo, O.A., Borgstahl, G.E.O., Masson, P., and Lockridge, O. (2005) Biochemistry V44, P1154.
  126. Newcomb, R.D., Campbell, P.M., Ollis, D.L., Cheah, E., Russell, R.J., and Oakeshott, J.G. (1997) Proc. Natl. Acad. Sci. USA V94, P7464.
  127. Nicolet, Y., Lockridge, O., Masson, P., Fontecilla-Camps, J.C., and Nachon, F. (2003) J. Biol. Chem. V278, P41141.
  128. Nomura, D.K., Leung, D., Chiang, K.P., Quistad, G.B., Cravatt, B.F., and Casida, J.E. (2005) Proc. Natl. Acad. Sci. USA V102, P6195.
  129. Nomura, D.K., Fujioka, K., Issa, R.S., Ward, A.M., Cravatt, B.F., and Casida, J.E. (2008) Toxicol. Appl. Pharmacol. V228, P42.
  130. Pan, Y., Gao, D. Yang, W., Cho, H., Yang, G., Tai, Hh., and Zhan, CG. (2005) Proc. Natl. Acad. USA V102, P16656.
  131. Pan, Y., Gao, D. and Zhan, C.G. (2008) J. Am. Chem. Soc. V130, P5140.
  132. Parsa, R., and Green, H. (2001) in “Proceedings of the Internal Symposium on Applications of Enzymes in Chemical and Biological Defense”. Orlando, FL.
  133. Petrikovics, I., Papahadjopoulos, D., I., Hong, K., Cheng, T.C., Baskin, S.I., Jiang, J., Jaszberenyi, J.C., Logue, B.A., Szilasi, M., Mcguinn, W.D., and Way, J.L. (2004) Toxicol. Sci. V77, P258.
  134. Potter, P.M. and Wadkins, R. (2006) Curr. Med. Chem. V11, P1045.
  135. Poyot, T., Nachon, F., Froment, M.T., Loiodice, M., Wieseler, S., Schopfer, L.M., Lockridge, O., and Masson, P. (2006) Biochim. Biophys. Acta V1764, P1470.
  136. Rastogi, V.K., Defranck, J.J., Cheng, T.-C., and Wild, J.R. (1997) Biochem. Biophys. Res. Comm. V241, P294.
  137. Ray, R. Boucher, L.J., and Lenz, D.E. (1988) Biochim. Biophys. Acta V967, P373.
  138. Redinbo, M.R., and Potter, P.M. (2005) Drug Discov.Today V10, P313.
  139. Renault, F., Chabriere, E., Andrieu, J.P., Dublet, B., Masson, P., and Rochu, D. (2006) J. Chromatogr. B V836, P15.
  140. Reshetnyak, A.V., Armentano, M.F., Ponomarenko, N.A., Vizzuso, D., Durova, O.M., Ziganshin, R., Serebryakova, M., Govorum, V., Gololobov, G., Morse, H.C., Friboulet, A., Makker, S.P., Gabibov, A.G. and Tramontano, A. (2007) J. Am. Chem. Soc., V129, P16175.
  141. Richardt, A., and Blum, M.M. (2008) Decontamination of warfare agents: enzymatic methods for the removal of B/C weapons, Wiley-VCH, Berlin, 311 pages.
  142. Rochu, D., Chabriere, E., and Masson, P. (2007a) Toxicology V233, P47.
  143. Rochu D., Renault, F., Clery-Barraud, C., Chabriere, E., and Masson P. (2007b) Biochim. Biophys. Acta V1774, P874.
  144. Rochu D., Chabriere, E., Renault, F., Elias, M., Clery-Barraud, C., and Masson P. (2007c) Biochem. Soc. Trans. V35, P1616.
  145. Russel, A.J., Berberich, J.A., Drevon, G.F., and Koepsel, R.R. (2003) Annu. Rev. Biomed. Engn. V5, P1.
  146. Samples, C.R., Raushel, F.M., and DeRose, V.J. (2007) Biochemistry V46, P3435.
  147. Satoh, T. and Hosokawa, M. (2006) Chem-Biol. Interact. V162, P195.
  148. Saxena, A., Ashani, Y., Raveh, L., Stevenson, D., Patel, T., and Doctor, B.P. (1998) Mol. Pharmacol. V53, P112.
  149. Saxena, A., Sun, W., Luo, C., Myers, T.M., Koplovitz, Lenz, D.E., and Doctor, B.P. (2006) J. Mol. Neurosci. V30, P145.
  150. Saxena, A., Luo, C., Chilukuri, N., Maxwell, D.M. and Doctor, B.P. (2007) In: Chemical Warfare Agents Chemistry, Pharmacology, Toxicology and Therapeutics, (Romano, J.A., Luckey, B.J. and Salem, H., Eds), CRC Press, Boca Raton, Fl, P145.
  151. Schallreuter, K.U., Gibbons, N.C.J., Elwary, S.M., Parkin, S.M., and Wood, J.M. (2007) Biochem. Biophys. Res. Commun. V355, P1069.
  152. Schopfer, L.M., Ticu-Boeck, A., Broomfield, C.A., and Lockridge, O. (2004) J. Med. Chem. Def. V2, P1.
  153. Seibert, C.M., and F.M. Raushel, (2005) Biochemistry V44, P6383.
  154. Shafferman, A., Ordentlich, A., Barak, D., Stein, D., Ariel, N., and Velan, B. (1996) Biochem. J. V318, P833.
  155. Shih, D.M., Gu, L., Xia, Y.R., Navab, M., LiIi, W.F., Hama, S., Castellani, L.W., Furlong, C.E., Costa, L.G., Fogelman, A.M., and Lusis, A.J. (1998) Nature V394, P284.
  156. Smolen, A., Eckreson, H.W., Gan, K.N., Hailat, N., and La Du, B.N. (1991) Drug. Metab. Dispos. V19, P107.
  157. Sogorb, M.A., Alvarez-Escalante, Carrera, V., and Vilanova, E. (2007) Arch. Toxicol. V81, P113.
  158. Sogorb, M.A., Garcia-Arquelles, S., Carrera, V. and Vilanova, E. (2008) Chem. Res. Toxicol. V21, P1524.
  159. Stevens, R.C., Suzuki, S.M., Cole, T.B., Park, S.S., Richter, R.J., and Furlong, C.E. (2008) Proc. Natl. Acad. USA V105, P12780.
  160. Sun, H., Pang, Y.P., Lockridge, O. and Brimijoin, S. (2002) Mol. Pharmacol., V62, P220.
  161. Sussman, J. L., Harel, M., Frolow, F., Oefner, C., Goldman, A., Toker, L., and Silman, I. (1991) Science V253, P872.
  162. Tahroni, M.H., Carter, W.G., and Ray, D.E. (2007) Toxicology V240, P173.
  163. Tavori, H., Khatib, S., Aviram, M., and Vaya, J. (2008) Bioorg Med. Chem. V16, P7504.
  164. Taylor, P., Reiner, E., Kovarik, Z., and Radić, Z. (2007) Arh. Hig. Rada. Toksikol. V58, P339.
  165. Thiermann, H., Szinicz, L., Eyer, P., Felgenhauer, N., Zilker, T., and Worek, F. (2007) Toxicology V233, P145.
  166. Vaisar, T., Pennathur, S., Green, P.S., Gharib, S.A., Hoofnagle, A.N., Cheung, M.C., Byun, J., Vuletic, S., Kassim, S., Singh, P., Chea, H., Knopp, R.H., Brunzell, J., Geary, R., Chait, A., Zhao, X.Q., Elkon, K., Marcovina, S., Ridker, P., Oram, J.F., Heinecke, J.W. (2007) J Clin Invest V117, P746.
  167. Vayron, P., Renard, P.Y., Taran, F., Creminon, C. Frobert, Y., Grassi, J., and Mioskovski, C. (2000) Proc. Natl. Acad. Sci. USA V97, P7058.
  168. Viragh, C., Akhmetshin, R., and Kovach, I. (1997) Biochemistry V36, P8243.
  169. Wang, Q.D., Sun, M.J., Zhang, H., and Huang, C.F. (1998) J. Biochem. Mol. Toxicol. V12, P213.
  170. Wang, S.H., Zhi, Q.W. and Sun, M.J. (2005) Arch. Toxicol. V79, P253.
  171. Wang, S.H., Zhi, Q.W., and Sun, M.J. (2006) Toxicol in Vitro V20, P71.
  172. Wang X, Wu N, Guo J, Chu X, Tian J, Yao B, Fan Y. (2008) Biochem. Biophys. Res. Commun. V365, P453.
  173. Wang, Y., Boeck, A.T., Duysen, E.G., van Keuren, M., Saunders, T.L., and Lockridge, O. (2004) Toxicol. Appl. Pharmacol. V196, P356.
  174. Watson, A.D., Berliner, J.A., Hama, S.Y., and La Du, B.N. (1995) J. Clin. Invest. V96, P2882.
  175. Wetherell, J., Price, M., Munford, H., Armstrong, and S. Scott, L. (2007) Toxicology V233, P120.
  176. Wolfe, A.D., Rush, R.S., Doctor, B.P., Koplovitz, I., and Jones, D. (1987) Fundam. Appl. Toxicol. V9, P266.
  177. Wong, K.-Y., and Gao, J. (2007) Biochemistry V46, P13352.
  178. Worek, F., Eyer, P., Aurbek, N., Szinicz, L., and Thiermann, H. (2007) Toxicol. Appl. Pharmacol. V219, P226.
  179. Xie W., Varkey-Altamirano, C., Bartels, C.F., Speirs, R.J., Cashman, J.R. and Lockridge, O. (1999) Mol. Pharmacol., V55, P83.
  180. Simo, Y., Butnaro, O., Eisenkraft, A., Shrot, S., Rosman, Y., Dushnitsky, T. and Krivoy, A. (2008) Crit. Rev. Biotechnol. V28, P265.
  181. Yeung, D.T., Josse, D., Nicholson, J.D., Khanal, A., Mcandrew, C.W., Bahnson, B.J., Lenz, D.E., and Cerasoli, D.M. (2004) Biochim. Biophys. Acta V1702, P67.
  182. Yeung, D.T., Smith, J., Sweeney, R., Lenz, D., and Cerasoli, D. (2008) J. Anal.Toxicol. V32, 86.
  183. Zhang, C., Peng, W., Jiang, X., Chen, B., Zhu, J., Zang, Y., Zhang, J., Zhu,, T., and Qin, J. (2008) J. Gene Med. V10, P94.
  184. Zheng, F., and Zhang, C.-G. (2008) Org. Biomol. Chem. V6, P836.
  185. Zheng, F., Yang, W., Ko, M-C., Liu, J., Cho, H., Gao, D., Tong, M., Tai, H-H., Woods, J.H. and Zhan, C-G. (2008) J. Am. Chem. Soc., V130, P12148.

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