Nerve Agent Bioscavengers: Progress in Development of a New Mode of Protection against Organophosphorus Exposure

Chemical Warfare Agents: Chemistry, Pharmacology, Toxicology, and Therapeutics

Volumn , Issue , 2007, Pages 175-202

  Lenz, David E ^a   Broomfield, Clarence A ^a   Yeung, David T ^a   Masson, Patrick ^b   Maxwell, Donald M ^a   Cerasoli, Douglas M ^a  

^a US ARMY MEDICAL RESEARCH INSTITUTE OF CHEMICAL DEFENSE   (United States)

^b CENTRE DE RECHERCHES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 50649101957     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/9781420046625-14     Document Type: Chapter

References (177)

1. Aharoni, A., Gaidukov, L., Yagur, S., Toker, L., Silman, I., and Tawfik, D.S. 2004, “Directed evolution of mammalian paraoxonases PON1 and PON3 for bacterial expression and catalytic specialization, " Proc. Natl. Acad. Sci. U.S.A., vol. 101, no. 2, pp. 482-487.
2. Aldridge, W.N. 1953a, “Serum esterases. I. Two types of esterase (A and B) hydrolysing p-nitrophenyl acetate, propionate and butyrate, and a method for their determination, " Biochem. J., vol. 53, no. 1, pp. 110-117.
3. Aldridge, W.N. 1953b, “Serum esterases. II. An enzyme hydrolysing diethyl p-nitrophenyl phosphate (E600) and its identity with the A-esterase of mammalian sera, " Biochem. J., vol. 53, no. 1, pp. 117-124.
4. Aldridge, W.N. and Reiner, E. 1972, “Enzyme Inhibitors as Substrates, " North Holland, Amsterdam.
5. Amitai, G., Adani, R., Rabinovitz, I., and Meshulam, H. 2002, “In vitro Skin Decontamination of VX by Enzymatic Peroxidation, " U.S. Army Medical Research Command, Hunt Valley, MD.
6. Amitai, G., Adani, R., Hershkovitz, M., Bel, P., Rabinovitz, I., and Meshulam, H. 2003, “Degradation of VX and sulfur mustard by enzymatic haloperoxidation, " J. Appl. Toxicol., vol. 23, no. 4, pp.225-233.
7. 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, “Enhanced stereoselective hydrolysis of toxic organophosphates by directly evolved variants of mammalian serum paraoxonase, " FEBS J., vol. 273, no. 9, pp. 1906-1919.
8. Ashani, Y., Shapira, S., Levy, D., Wolfe, A.D., Doctor, B.P., and Raveh, L. 1991, “Butyrylcholinesterase and acetylcholinesterase prophylaxis against soman poisoning in mice, " Biochem. Pharmacol., vol. 41, no. 1, pp. 37-41.
9. Augustinsson, K.B. 1958, “Electrophoretic separation and classification of blood esterases, " Nature, vol. 131, p. 1786.
10. Aviram, M., Billecke, S., Sorenson, R., Bisgaier, C., Newton, R., Rosenblat, M., Erogul, J., Hsu, C., Dunlop, C., and La Du, B. 1998, “Paraoxonase active site required for protection against LDL oxidation involves its free sulfhydryl group and is different from that required for its arylesterase/paraoxonase activities: selective action of human paraoxonase allozymes Q and R, " Arterioscler. Thromb. Vasc. Biol., vol. 18, no. 10, pp. 1617-1624.
11. Bajgar, J., Jakl, A., and Hrdina, V. 1971, “Effect of atropine and trimedoxime on the acetylcholinesterase activity in some parts of the mouse brain, " Cesk. Farm., vol. 20, no. 7, pp. 257-260.
12. Ballantyne, B. and Marrs, T.C. 1992, “Overview of the biological and clinical aspects of organophosphates and carbamates, " in Clinical and Experimental Toxicology of Organophosphates and Carbamates, B. Ballantyne and T.C. Marrs, eds., Butterworth, Oxford, London, p. 1.
13. Billecke, S., Draganov, D., Counsell, R., Stetson, P., Watson, C., Hsu, C., and La Du, B.N. 2000, “Human serum paraoxonase (PON1) isozymes Q and R hydrolyze lactones and cyclic carbonate esters, " Drug Metab. Dispos., vol. 28, no. 11, pp. 1335-1342.
14. Bismuth, C., Inns, R.H., and Marrs, T.C. 1992, “Efficacy, toxicity, and clinical use of oximes in anticholinesterase poisoning, " in Clinical and Experimental Toxicology of Organophosphorus and Carbamates, B. Ballantyne and T.C. Marrs, eds., Butterworth, Oxford, London, p. 555.
15. Blatter, M.C., James, R.W., Messmer, S., Barja, F., and Pometta, D. 1993, “Identification of a distinct human high-density lipoprotein subspecies defined by a lipoprotein-associated protein, K-45. Identity of K-45 with paraoxonase, " Eur. J. Biochem., vol. 211, no. 3, pp. 871-879.
16. Blick, D.W., Murphy, M.R., Brown, G.C., Yochmowitz, M.G., Fanton, J.W., and Hartgraves, S.L. 1994, “Acute behavioral toxicity of pyridostigmine or soman in primates, " Toxicol. Appl. Pharmacol., vol. 126, no. 2, pp. 311-318.
17. Brandeis, R., Raveh, L., Grunwald, J., Cohen, E., and Ashani, Y. 1993, “Prevention of soman-induced cognitive deficits by pretreatment with human butyrylcholinesterase in rats, " Pharmacol. Biochem.Behav., vol. 46, no. 4, pp. 889-896.
18. Brimblecombe, R.W. 1977, “Drugs acting on central cholinergic mechanisms and affecting respiration, " Pharmacol. Ther. [B], vol. 3, no. 1, pp. 65-74.
19. Brimfield, A.A., Lenz, D.E., Maxwell, D.M., and Broomfield, C.A. 1993, “Catalytic antibodies hydrolysing organophosphorus esters, " Chem. Biol. Interact., vol. 87, no. 1-3, pp. 95-102.
20. Brites, F.D., Verona, J., Schreier, L.E., Fruchart, J.C., Castro, G.R., and Wikinski, R.L. 2004, “Paraoxonase 1 and platelet-activating factor acetylhydrolase activities in patients with low hdl-cholesterol levels with or without primary hypertriglyceridemia, " Arch. Med. Res., vol. 35, no. 3, pp. 235-240.
21. Broomfield, C.A. 1992, “A purified recombinant organophosphorus acid anhydrase protects mice against soman, " Pharmacol. Toxicol., vol. 70, no. 1, pp. 65-66.
22. Broomfield, C.A., Maxwell, D.M., Solana, R.P., Castro, C.A., Finger, A.V., and Lenz, D.E. 1991, “Protection by butyrylcholinesterase against organophosphorus poisoning in nonhuman primates, " J. Pharmacol.Exp. Ther., vol. 259, no. 2, pp. 633-638.
23. Broomfield, C.A., Millard, C.B., Lockridge, O., and Caviston, T.L. 1995, “Mutations of human butyrylcholinesterase glycine 117 to histidine preserves activity but confers resistance to organophosphorus inhibitors, " in Enzymes of the Cholinesterase Family, D.M. Quinn et al., eds., Plenum Press, New York, p. 169.
24. Broomfield, C.A., Morris, B.C., Anderson, R., Josse, D., and Masson, P. 2000, “Kinetics of Nerve Agent Hydrolysis by a Human Plasma Enzyme, " U.S. Army Medical Research Institute of Chemical Defense, Aberdeen Proving Ground, MD.
25. Castro, C.A., Larsen, T., Finger, A.V., Solana, R.P., and McMaster, S.B. 1992, “Behavioral efficacy of diazepam against nerve agent exposure in rhesus monkeys, " Pharmacol. Biochem. Behav., vol. 41, no. 1, pp. 159-164.
26. Castro, C.A., Gresham, V.C., Finger, A.V., Maxwell, D.M., Solana, R.P., Lenz, D.E., and Broomfield, C.A. 1994, “Behavioral decrements persist in rhesus monkeys trained on a serial probe recognition task despite protection against soman lethality by butyrylcholinesterase, " Neurotoxicol. Teratol., vol. 16, no. 2, pp. 145-148.
27. Cerasoli, D.M., Griffiths, E.M., Doctor, B.P., Saxena, A., Fedorko, J.M., Greig, N.H., Yu, Q.S., Huang, Y., Wilgus, H., Karatzas, C.N., Koplovitz, I., and Lenz, D.E. 2005a, “In vitro and in vivo characterization of recombinant human butyrylcholinesterase (Protexia) as a potential nerve agent bioscavenger, " Chem.Biol. Interact., vol. 157-158, pp. 363-365.
28. Cerasoli, D.M., Robison, C.L., Nwaneri, I.Y., Somsamayvong, B., Karatzas, C.N., Wilgus, H., Huang, Y., McDonough, J.H., Lenz, D.E., and Lumley, L.A. 2005b, “Pretreatment with pegylated protexia protects against exposure to the nerve agents VX and soman, " Soc. Neurosci., 31, 337.19.
29. Chabrier, P.E. and Jacob, J. 1980, “In vivo and in vitro inhibition of cholinesterase by methyl-1 (S methyl phosphoryl-3) imidazolium (MSPI), a model of an ‘instantly’ aged phosphorylated enzyme, " Arch.Toxicol., vol. 45, no. 1, pp. 15-20.
30. Cheng, T.C., Liu, L., Wang, B., Wu, J., Frank, J.J., Anderson, D.M., Rastogi, V.K., and Hamilton, A.B. 1997, “Nucleotide sequence of a gene encoding an organophosphorus nerve agent degrading enzyme from Alteromonas haloplanktis, " J. Ind. Microbiol., vol. 18, p. 49.
31. Clement, J.G. 1982, “HI-6: reactivation of central and peripheral acetylcholinesterase following inhibition by soman, sarin and tabun in vivo in the rat, " Biochem. Pharmacol., vol. 31, no. 7, pp. 1283-1287.
32. Clendenning, J.B., Humbert, R., Green, E.D., Wood, C., Traver, D., and Furlong, C.E. 1996, “Structural organization of the human PON1 gene, " Genomics, vol. 35, no. 3, pp. 586-589.
33. Costa, L.G., Li, W.F., Richter, R.J., Shih, D.M., Lusis, A., and Furlong, C.E. 1999, “The role of paraoxonase (PON1) in the detoxication of organophosphates and its human polymorphism, " Chem. Biol. Interact., vol. 119-120, pp. 429-438.
34. Costa, L.G., Cole, T.B., Jarvik, G.P., and Furlong, C.E. 2003a, “Functional genomics of the paraoxonase (PON1) polymorphisms: effects on pesticide sensitivity, cardiovascular disease, and drug metabolism, " Annu. Rev. Med., vol. 54, pp. 371-392.
35. Costa, L.G., Richter, R.J., Li, W.F., Cole, T., Guizzetti, M., and Furlong, C.E. 2003b, “Paraoxonase (PON 1) as a biomarker of susceptibility for organophosphate toxicity, " Biomarkers, vol. 8, no. 1, pp. 1-12.
36. Costa, L.G., Cole, T.B., Vitalone, A., and Furlong, C.E. 2005, “Measurement of paraoxonase (PON1) status as a potential biomarker of susceptibility to organophosphate toxicity, " Clin. Chim. Acta, vol. 352, no. 1-2, pp. 37-47.
37. Dacre, J.C. 1984, “Toxicology of some anticholinesterases used as a chemical warfare agents-a review, " in Cholinesterases, Fundamental and Applied Aspects, M. Brzin, E.A. Barnard, and D. Sket, eds., de Gruyter, Berlin, Germany, p. 415.
38. Davies, H.G., Richter, R.J., Keifer, M., Broomfield, C.A., Sowalla, J., and Furlong, C.E. 1996, “The effect of the human serum paraoxonase polymorphism is reversed with diazoxon, soman and sarin, " Nat. Genet., vol. 14, no. 3, pp. 334-336.
39. de Candole, C.A., Douglas, W.W., Evans, C.L., Holmes, R., Spencer, K.E.V., Torrance, R.W., and Wilson, K.M. 1953, “The failure of respiration in death by anticholinesterase poisoning, " Br. J. Pharmacol. Chemother., vol. 6, p. 466.
40. Doctor, B.P. and Saxena, A. 2005, “Bioscavengers for the protection of humans against organophosphate toxicity, " Chem. Biol. Interact., vol. 157-158, pp. 167-171.
41. Doctor, B.P., Raveh, L., Wolfe, A.D., Maxwell, D.M., and Ashani, Y. 1991, “Enzymes as pretreatment drugs for organophosphate toxicity, " Neurosci. Biobehav. Rev., vol. 15, no. 1, pp. 123-128.
42. Doctor, B.P., Blick, D.W., Caranto, G., Castro, C.A., Gentry, M.K., Larrison, R., Maxwell, D.M., Murphy, M.R., Schutz, M., Waibel, K., et al. 1993, “Cholinesterases as scavengers for organophosphorus compounds: protection of primate performance against soman toxicity, " Chem. Biol. Interact., vol. 87, no. 1-3, pp. 285-293.
43. Doorn, J.A., Sorenson, R.C., Billecke, S.S., Hsu, C., and La Du, B.N. 1999, “Evidence that several conserved histidine residues are required for hydrolytic activity of human paraoxonase/arylesterase, " Chem. Biol.Interact., vol. 119-120, pp. 235-241.
44. Draganov, D.I., Stetson, P.L., Watson, C.E., Billecke, S.S., and La Du, B.N. 2000, “Rabbit serum paraoxonase 3 (PON3) is a high density lipoprotein-associated lactonase and protects low density lipoprotein against oxidation, " J. Biol. Chem., vol. 275, no. 43, pp. 33435-33442.
45. Dumas, D.P., Durst, H.D., Landis, W.G., Raushel, F.M., and Wild, J.R. 1990, “Inactivation of organophosphorus nerve agents by the phosphotriesterase from Pseudomonas diminuta, " Arch. Biochem. Biophys., vol. 277, no. 1, pp. 155-159.
46. Dunn, M.A. and Sidell, F.R. 1989, “Progress in medical defense against nerve agents, " JAMA, vol. 262, no. 5, pp. 649-652.
47. Duysen, E.G., Li, B., Darvesh, S., and Lockridge, O. 2006, “Sensitivity of butyrylcholinesterase knockout mice to (-)-huperzine A and donepezil suggests humans with butyrylcholinesterase deficiency may not tolerate these Alzheimer’s disease drugs and indicates butyrylcholinesterase function in neurotransmission, " Toxicology, vol. 233, no. 1-3, pp. 60-69.
48. Ellinghaus, P., Seedorf, U., and Assmann, G. 1998, “Cloning and sequencing of a novel murine liver carboxylesterase cDNA, " Biochim. Biophys. Acta, vol. 1397, no. 2, pp. 175-179.
49. Ember, L. 1991, “Chemical weapons: plans prepared to destroy Iraqi arms, " Chem. Eng. News, vol. 19, p. 6.
50. Erdmann, W., Bosse, I., and Franke, P. 1965, “Resorption and excretion of toxogonin following intramuscular injection in man, " Dtsch. Med. Wochenschr., vol. 90, pp. 1436-1438.
51. Fidder, A., Moes, G.W., Scheffer, A.G., van der Schans, G.P., Baan, R.A., de Jong, L.P., and Benschop, H.P. 1994, “Synthesis, characterization, and quantitation of the major adducts formed between sulfur mustard and DNA of calf thymus and human blood, " Chem. Res. Toxicol., vol. 7, no. 2, pp. 199-204.
52. Fleisher, J.H. and Harris, L.W. 1965, “Dealkylation as a mechanism for aging of cholinesterase after poisoning with pinacolyl methylphosphonofluoridate, " Biochem. Pharmacol., vol. 14, no. 5, pp. 641-650.
53. Fletcher, S.P., Geyer, B.C., Smith, A., Evron, T., Joshi, L., Soreq, H., and Mor, T.S. 2004, “Tissue distribution of cholinesterases and anticholinesterases in native and transgenic tomato plants, " Plant Mol. Biol., vol. 55, no. 1, pp. 33-43.
54. Furlong, C.E., Li, W.F., Costa, L.G., Richter, R.J., Shih, D.M., and Lusis, A.J. 1998, “Genetically determined susceptibility to organophosphorus insecticides and nerve agents: developing a mouse model for the human PON1 polymorphism, " Neurotoxicology, vol. 19, no. 4-5, pp. 645-650.
55. Furlong, C.E., Li, W.F., Brophy, V.H., Jarvik, G.P., Richter, R.J., Shih, D.M., Lusis, A.J., and Costa, L.G. 2000a, “The PON1 gene and detoxication, " Neurotoxicology, vol. 21, no. 4, pp. 581-587.
56. Furlong, C.E., Li, W.F., Richter, R.J., Shih, D.M., Lusis, A.J., Alleva, E., and Costa, L.G. 2000b, “Genetic and temporal determinants of pesticide sensitivity: role of paraoxonase (PON1), " Neurotoxicology, vol. 21, no. 1-2, pp. 91-100.
57. Furlong, C.E., Cole, T.B., Jarvik, G.P., and Costa, L.G. 2002, “Pharmacogenomic considerations of the paraoxonase polymorphisms, " Pharmacogenomics, vol. 3, no. 3, pp. 341-348.
58. Gaidukov, L., Rosenblat, M., Aviram, M., and Tawfik, D.S. 2006, “The 192R/Q polymorphs of serum paraoxonase PON1 differ in HDL binding, lipolactonase stimulation, and cholesterol efflux, " J. Lipid Res., vol. 47, no. 11, pp. 2492-2502.
59. Gan, K.N., Smolen, A., Eckerson, H.W., and La Du, B.N. 1991, “Purification of human serum paraoxonase/ arylesterase. Evidence for one esterase catalyzing both activities, " Drug Metab. Dispos., vol. 19, no. 1, pp. 100-106.
60. Garcia, G.E., Moorad-Doctor, D., Doctor, B.P., Saxena, A., Lockridge, O., Lenz, D.E., Cerasoli, D., and Huang, Y. 2005, “Glycan structure comparison of native human plasma butyrylcholinesterase (Hu-BChE) and transgenic goat produced Hu-BChE, " FASEB J., vol. 19, p. A867.
61. Genovese, R.F. and Doctor, B.P. 1995, “Behavioral and pharmacological assessment of butyrylcholinesterase in rats, " Pharmacol. Biochem. Behav., vol. 51, no. 4, pp. 647-654.
62. Gordon, J.J., Leadbeater, L., and Maidment, M.P. 1978, “The protection of animals against organophosphate poisoning by pretreatment with a carbamate, " Toxicol. Appl. Pharmacol., vol. 43, no. 1, pp. 207-216.
63. Gouedard, C., Koum-Besson, N., Barouki, R., and Morel, Y. 2003, “Opposite regulation of the human paraoxonase-1 gene PON-1 by fenofibrate and statins, " Mol. Pharmacol., vol. 63, no. 4, pp. 945-956.
64. Gouedard, C., Barouki, R., and Morel, Y. 2004, “Dietary polyphenols increase paraoxonase 1 gene expression by an aryl hydrocarbon receptor-dependent mechanism, " Mol. Cell Biol., vol. 24, no. 12, pp. 5209-5222.
65. Hanke, D.W. and Overton, M.A. 1991, “Phosphylation kinetic constants and oxime-induced reactivation in acetylcholinesterase from fetal bovine serum, bovine caudate nucleus, and electric eel, " J. Toxicol.Environ. Health, vol. 34, no. 1, pp. 141-156.
66. Harel, M., Aharoni, A., Gaidukov, L., Brumshtein, B., Khersonsky, O., Meged, R., Dvir, H., Ravelli, R.B., McCarthy, A., Toker, L., Silman, I., Sussman, J.L., and Tawfik, D.S. 2004a, “Corrigendum: structure and evolution of the serum paraoxonase family of detoxifying and anti-atherosclerotic enzymes, " Nat. Struct. Mol. Biol., vol. 11, no. 12, p. 1253.
67. Harel, M., Aharoni, A., Gaidukov, L., Brumshtein, B., Khersonsky, O., Meged, R., Dvir, H., Ravelli, R.B., McCarthy, A., Toker, L., Silman, I., Sussman, J.L., and Tawfik, D.S. 2004b, “Structure and evolution of the serum paraoxonase family of detoxifying and anti-atherosclerotic enzymes, " Nat. Struct. Mol. Biol., vol. 11, no. 5, pp. 412-419.
68. Harris, L.W., Fleisher, J.H., Clark, J., and Cliff, W.J. 1966, “Dealkylation and loss of capacity for reactivation of cholinesterase inhibited by sarin, " Science, vol. 154, no. 747, pp. 404-407.
69. Hartleib, J. and Ruterjans, H. 2001, “Insights into the reaction mechanism of the diisopropyl fluorophosphatase from Loligo vulgaris by means of kinetic studies, chemical modification and site-directed mutagenesis, " Biochim. Biophys. Acta, vol. 1546, no. 2, pp. 312-324.
70. Hassett, C., Richter, R.J., Humbert, R., Chapline, C., Crabb, J.W., Omiecinski, C.J., and Furlong, C.E. 1991, “Characterization of cDNA clones encoding rabbit and human serum paraoxonase: the mature protein retains its signal sequence, " Biochemistry, vol. 30, no. 42, pp. 10141-10149.
71. Heath, A.J.W. and Meredith, T. 1992, “Atropine in the management of anticholinesterase poisoning, " in Clinical and Experimental Toxicology of Organophosphates and Cabamates, B. Ballantyne and T.C. Marrs, eds., Butterworth, Oxford, London, p. 543.
72. Heffron, P.F. and Hobbiger, F. 1979, “Relationship between inhibition of acetylcholinesterase and response of the rat phrenic nerve-diaphragm preparation to indirect stimulation at higher frequencies, " Br. J. Pharmacol., vol. 66, no. 2, pp. 323-329.
73. Huff, B.B. 1986, “Physician’s Desk Reference, " Medical Economics Co. Inc., Oradell.
74. Jakubowski, H. 2000, “Calcium-dependent human serum homocysteine thiolactone hydrolase. a protective mechanism against protein N-homocysteinylation, " J. Biol. Chem., vol. 275, no. 6, pp. 3957-3962.
75. Jakubowski, H., Ambrosius, W.T., and Pratt, J.H. 2001, “Genetic determinants of homocysteine thiolactonase activity in humans: implications for atherosclerosis, " FEBS Lett., vol. 491, no. 1-2, pp. 35-39.
76. James, R.W. and Deakin, S.P. 2004, “The importance of high-density lipoproteins for paraoxonase-1 secretion, stability, and activity, " Free Radic. Biol. Med., vol. 37, no. 12, pp. 1986-1994.
77. Jarv, S. 1984, “Stereochemical aspects of cholinesterase catalysis, " Bioorg. Med. Chem., vol. 12, p. 259.
78. Jokanovic, M., Kosanovic, M., and Maksimovic, M. 1996, “Interaction of organophosphorus compounds with carboxylesterases in the rat, " Arch. Toxicol., vol. 70, no. 7, pp. 444-450.
79. Josse, D., Xie, W., Masson, P., and Lockridge, O. 1999a, “Human serum paraoxonase (PON1): identification of essential amino acid residues by group-selective labelling and site-directed mutagenesis, " Chem. Biol.Interact., vol. 119-120, pp. 71-78.
80. Josse, D., Xie, W., Masson, P., Schopfer, L.M., and Lockridge, O. 1999b, “Tryptophan residue(s) as major components of the human serum paraoxonase active site, " Chem. Biol. Interact., vol. 119-120, pp. 79-84.
81. Josse, D., Xie, W., Renault, F., Rochu, D., Schopfer, L.M., Masson, P., and Lockridge, O. 1999c, “Identification of residues essential for human paraoxonase (PON1) arylesterase/organophosphatase activities, " Biochemistry, vol. 38, no. 9, pp. 2816-2825.
82. Josse, D., Lockridge, O., Xie, W., Bartels, C.F., Schopfer, L.M., and Masson, P. 2001, “The active site of human paraoxonase (PON1), " J. Appl. Toxicol., vol. 21 Suppl. 1, pp. 7-11.
83. Josse, D., Broomfield, C.A., Cerasoli, D., Kirby, S., Nicholson, J., Bahnson, B., and Lenz, D.E. 2002 “Engineering of HuPON1 for a Use as a Catalytic Bioscavenger in Organophosphate Poisoning, " U.S. Army Medical Research Institute of Chemical Defense, Aberdeen Proving Ground, MD.
84. Khersonsky, O. and Tawfik, D.S. 2005, “Structure-reactivity studies of serum paraoxonase PON1 suggest that its native activity is lactonase, " Biochemistry, vol. 44, no. 16, pp. 6371-6382.
85. Khersonsky, O. and Tawfik, D.S. 2006, “The histidine 115-134 DYAD mediates the lactonase activity of mammalian serum paraoxonases, " J. Biol. Chem. vol. 281, no. 11, pp. 7649-7656.
86. Koelle, G.B. 1963, “Cholinesterases and anticholinesterases, " in Handbuch der Experimentallen Pharmackologie, O. Ekhler and P.I. Feder, eds., Springer-Verlag, Berlin, Germany.
87. Korza, G. and Ozols, J. 1988, “Complete covalent structure of 60-kDa esterase isolated from 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin-induced rabbit liver microsomes, " J. Biol. Chem., vol. 263, no. 7, pp. 3486-3495.
88. Kuo, C.L. and La Du, B.N. 1998, “Calcium binding by human and rabbit serum paraoxonases. Structural stability and enzymatic activity, " Drug Metab. Dispos., vol. 26, no. 7, pp. 653-660.
89. La Du, B.N., Furlong, C.E., and Reiner, E. 1999, “Recommended nomenclature system for the paraoxonases, " Chem. Biol. Interact., vol. 119-120, pp. 599-601.
90. Lacinski, M., Skorupski, W., Cieslinski, A., Sokolowska, J., Trzeciak, W.H., and Jakubowski, H. 2004, “Determinants of homocysteine-thiolactonase activity of the paraoxonase-1 (PON1) protein in humans, " Cell Mol. Biol. (Noisy-le-grand), vol. 50, no. 8, pp. 885-893.
91. Langenberg, J.P., van Dijk, C., Sweeney, R.E., Maxwell, D.M., de Jong, L.P., and Benschop, H.P. 1997, “Development of a physiologically based model for the toxicokinetics of C(þ/_)P(þ/_)-soman in the atropinized guinea pig, " Arch. Toxicol., vol. 71, no. 5, pp. 320-331.
92. Leadbeater, L., Inns, R.H., and Rylands, J.M. 1985, “Treatment of poisoning by soman, " Fundam. Appl.Toxicol., vol. 5, no. 6 Pt 2, pp. S225-S231.
93. Lenz, D.E. and Cerasoli, D.M. 2002, “Nerve agent bioscavengers: protection with reduced behavioral effects, " Mil. Psychol., vol. 14, p. 121.
94. Lenz, D.E., Brimfield, A.A., and Cook, A.A. 1997, “The development of immunoassays for detection of chemical warfare agents, " in Development and Applications of Immunoassays for Environmental Analysis, D. Aga and E.M. Thurman, eds., ACS Books, Washington DC, p. 77.
95. Lenz, D.E., Maxwell, D.M., Koplovitz, I., Clark, C.R., Capacio, B.R., Cerasoli, D.M., Federko, J.M., Luo, C., Saxena, A., Doctor, B.P., and Olson, C. 2005, “Protection against soman or VX poisoning by human butyrylcholinesterase in guinea pigs and cynomolgus monkeys, " Chem. Biol. Interact., vol. 157-158, pp. 205-210.
96. Li, B., Sedlacek, M., Manoharan, I., Boopathy, R., Duysen, E.G., Masson, P., and Lockridge, O. 2005, “Butyrylcholinesterase, paraoxonase, and albumin esterase, but not carboxylesterase, are present in human plasma, " Biochem. Pharmacol., vol. 70, no. 11, pp. 1673-1684.
97. Li, W.F., Costa, L.G., and Furlong, C.E. 1993, “Serum paraoxonase status: a major factor in determining resistance to organophosphates, " J. Toxicol. Environ. Health, vol. 40, no. 2-3, pp. 337-346.
98. Li, W.F., Furlong, C.E., and Costa, L.G. 1995, “Paraoxonase protects against chlorpyrifos toxicity in mice, " Toxicol. Lett., vol. 76, no. 3, pp. 219-226.
99. Li, W.F., Costa, L.G., Richter, R.J., Hagen, T., Shih, D.M., Tward, A., Lusis, A.J., and Furlong, C.E. 2000, “Catalytic efficiency determines the in-vivo efficacy of PON1 for detoxifying organophosphorus compounds, " Pharmacogenetics, vol. 10, no. 9, pp. 767-779.
100. Lockridge, O., Blong, R.M., Masson, P., Froment, M.T., Millard, C.B., and Broomfield, C.A. 1997, “A single amino acid substitution, Gly117His, confers phosphotriesterase (organophosphorus acid anhydride hydrolase) activity on human butyrylcholinesterase, " Biochemistry, vol. 36, no. 4, pp. 786-795.
101. Long, R.M., Satoh, H., Martin, B.M., Kimura, S., Gonzalez, F.J., and Pohl, L.R. 1988, “Rat liver carboxylesterase: cDNA cloning, sequencing, and evidence for a multigene family, " Biochem. Biophys. Res.Commun., vol. 156, no. 2, pp. 866-873.
102. Main, A.R. 1956, “The role of A-esterase in the acute toxicity of paraoxon, TEPP, and parathion, " Can.J. Biochem. Physiol., vol. 34, no. 2, pp. 197-216.
103. Masson, P., Adkins, S., Pham-Trong, P., and Lockridge, O. 1992, “Expression and refolding of functional human butyrylcholinesterase from E. coli, " in Multidisciplinary Approaches to Cholinesterase Function, A. Shafferman and B. Velan, eds., Plenum Press, NY pp. 49-52.
104. Masson, P., Josse, D., Lockridge, O., Viguie, N., Taupin, C., and Buhler, C. 1998, “Enzymes hydrolyzing organophosphates as potential catalytic scavengers against organophosphate poisoning, " J. Physiol.Paris, vol. 92, no. 5-6, pp. 357-362.
105. Masuda, N., Takatsu, M., Morinari, H., and Ozawa, T. 1995, “Sarin poisoning in Tokyo subway, " Lancet, vol. 345, no. 8962, p. 1446.
106. Matsushima, M., Inoue, H., Ichinose, M., Tsukada, S., Miki, K., Kurokawa, K., Takahashi, T., and Takahashi, K. 1991, “The nucleotide and deduced amino acid sequences of porcine liver proline- beta-naphthylamidase.Evidence for the identity with carboxylesterase, " FEBS Lett., vol. 293, no. 1-2, pp. 37-41.
107. Matzke, S.M., Oubre, J.L., Caranto, G.R., Gentry, M.K., and Galbicka, G. 1999, “Behavioral and immunological effects of exogenous butyrylcholinesterase in rhesus monkeys, " Pharmacol. Biochem. Behav., vol. 62, no. 3, pp. 523-530.
108. Maxwell, D.M. 1992, “The specificity of carboxylesterase protection against the toxicity of organophosphorus compounds, " Toxicol. Appl. Pharmacol., vol. 114, pp. 306-312.
109. Maxwell, D.M., Brecht, K.M., and O’Neill, B.L. 1987, “The effect of carboxylesterase inhibition on interspecies differences in soman toxicity, " Toxicol. Lett., vol. 39, no. 1, pp. 35-42.
110. Maxwell, D.M., Wolfe, A.D., Ashani, Y., and Doctor, B.P. 1991, “Cholinesterase and carboxylesterase as scavengers for organophosphorus agents, " in Cholinesterases: Structure, Function, Mechanism, Genetics and Cell Biology, J. Massoulie et al., eds., American Chemical Society, Washington DC, p. 206.
111. Maxwell, D.M., Castro, C.A., De La Hoz, D.M., Gentry, M.K., Gold, M.B., Solana, R.P., Wolfe, A.D., and Doctor, B.P. 1992, “Protection of rhesus monkeys against soman and prevention of performance decrement by pretreatment with acetylcholinesterase, " Toxicol. Appl. Pharmacol., vol. 115, no. 1, pp. 44-49.
112. Maxwell, D.M., Brecht, K.M., Doctor, B.P., and Wolfe, A.D. 1993, “Comparison of antidote protection against soman by pyridostigmine, HI-6 and acetylcholinesterase, " J. Pharmacol. Exp. Ther., vol. 264, no. 3, pp. 1085-1089.
113. Maxwell, D.M., Lieske, C.N., and Brecht, K.M. 1994, “Oxime-induced reactivation of carboxylesterase inhibited by organophosphorus compounds, " Chem. Res. Toxicol., vol. 7, no. 3, pp. 428-433.
114. Maxwell, D.M., Brecht, K.M., Saxena, A., Feaster, S.R., and Doctor, B.P. 1998, “Comparison of cholinesterases and carboxylesterases as bioscavengers for organophosphorus compounds, " in Structure and Function of Cholinesterases and Related Proteins, B.P. Doctor, D.M. Quinn, and P. Taylor, eds., Plenum Press, New York, p. 387.
115. Maynard, R.L. and Beswick, F.W. 1992, “Organophosphorus compounds as chemical warfare agents, " in Clinical and Experimental Toxicology of Organophosphates and Carbamates, B. Ballantyne and T.C. Marrs, eds., Butterworth, Oxford, London, p. 373.
116. Mazur, A. 1946, “An enzyme in animal tissues capable of hydrolyzing the phosphorus-fluorine bond of alkyl fluorophosphates, " J. Biol. Chem., vol. 164, pp. 271-289.
117. McDonough, J.H. 2002, “Performance impacts of nerve agents and their pharmacological countermeasures, " Mil. Psychol., vol. 14, no. 2, pp. 93-119.
118. Medda, S. and Proia, R.L. 1992, “The carboxylesterase family exhibits C-terminal sequence diversity reflecting the presence or absence of endoplasmic-reticulum-retention sequences, " Eur. J. Biochem., vol. 206, no. 3, pp. 801-806.
119. Mesulam, M.M., Guillozet, A., Shaw, P., Levey, A., Duysen, E.G., and Lockridge, O. 2002, “Acetylcholinesterase knockouts establish central cholinergic pathways and can use butyrylcholinesterase to hydrolyze acetylcholine, " Neuroscience, vol. 110, no. 4, pp. 627-639.
120. Millard, C.B., Lockridge, O., and Broomfield, C.A. 1995, “Design and expression of organophosphorus acid anhydride hydrolase activity in human butyrylcholinesterase, " Biochemistry, vol. 34, no. 49, pp. 15925-15933.
121. Millard, C.B., Lockridge, O., and Broomfield, C.A. 1998, “Organophosphorus acid anhydride hydrolase activity in human butyrylcholinesterase: synergy results in a somanase, " Biochemistry, vol. 37, no. 1, pp. 237-247.
122. Miller, A.D., Scott, D.F., Chacko, T.L., Maxwell, D.M., Schlager, J.J., and Lanclos, K.D. 1999, “Expression and partial purification of a recombinant secretory form of human liver carboxylesterase, " Protein Expr.Purif., vol. 17, p. 16.
123. Mor, T.S., Sternfeld, M., Soreq, H., Arntzen, C.J., and Mason, H.S. 2001, “Expression of recombinant human acetylcholinesterase in transgenic tomato plants, " Biotechnol. Bioeng., vol. 75, no. 3, pp. 259-266.
124. Morales, R., Beswick, F.W., Carpentier, P., Contreras-Martel, C., Renault, F., Nicodeme, M., Chesne-Seck, M., Bernier, F., Depuy, J., Schaeffer, C., Diemer, H., Van-Dorsselaer, A., Fontecilla-Camps, J.C., Masson, P., Rochu, D., and Chabriere, E. 2006, “Serendipitous discovery and x-ray structure of a human phosphate binding apolipoprotein, " Structure, vol. 14, pp. 1-9.
125. Murakami, K., Takagi, Y., Mihara, K., and Omura, T. 1993, “An isozyme of microsomal carboxyesterases, carboxyesterase Sec, is secreted from rat liver into the blood, " J. Biochem. (Tokyo), vol. 113, no. 1, pp. 61-66.
126. Nachon, F., Wieseler, S., Masson, P., and Lockridge, O. 2003, “Optimization of the Expression of Human Butyrylcholinesterase, " Proceedings NATO TG-004 meeting Medicine Hat, Canada.
127. Ordentlich, A., Kronman, C., Barak, D., Stein, D., Ariel, N., Marcus, D., Velan, B., and Shafferman, A. 1993, “Engineering resistance to ‘aging’ of phosphylated human acetylcholinesterase. Role of hydrogen bond network in the active center, " FEBS Lett., vol. 334, no. 2, pp. 215-220.
128. Ovnic, M., Swank, R.T., Fletcher, C., Zhen, L., Novak, E.K., Baumann, H., Heintz, N., and Ganschow, R.E. 1991a, “Characterization and functional expression of a cDNA encoding egasyn (esterase-22): the endoplasmic reticulum-targeting protein of beta-glucuronidase, " Genomics, vol. 11, no. 4, pp. 956-967.
129. Ovnic, M., Tepperman, K., Medda, S., Elliott, R.W., Stephenson, D.A., Grant, S.G., and Ganschow, R.E. 1991b, “Characterization of a murine cDNA encoding a member of the carboxylesterase multigene family, " Genomics, vol. 9, no. 2, pp. 344-354.
130. Ozols, J. 1989, “Isolation, properties, and the complete amino acid sequence of a second form of 60-kDa glycoprotein esterase. Orientation of the 60-kDa proteins in the microsomal membrane, " J. Biol. Chem., vol. 264, no. 21, pp. 12533-12545.
131. Parsa, R. and Green, H. 2001, “Destruction of DFP by organophosphorus acid anhydrase covalently coupled to the cornified layer of human epidermis, " in Proceedings of the International Symposium on Applications of Enzymes in Chemical and Biological Defense, Orlando, FL.
132. Patel, P., Clark, C.R., Brecht, K., Maxwell, D.M., Lenz, D.E., and Cerasoli, D. 2005, “Binding of organophosphorus compounds to sera from rats, guinea pigs, monkeys and humans, " FASEB J., vol. 19, no. 5, Abstract 527.13 edn.
133. Petrikovics, I., Papahadjopoulos, D., 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, “Comparing therapeutic and prophylactic protection against the lethal effect of paraoxon, " Toxicol. Sci., vol. 77, no. 2, pp. 258-262.
134. Poyot, T., Nachon, F., Froment, M.T., Loiodice, M., Wieseler, S., Schopfer, L.M., Lockridge, O., and Masson, P. 2006, “Mutant of Bungarus fasciatus acetylcholinesterase with low affinity and low hydrolase activity toward organophosphorus esters, " Biochim. Biophys. Acta, vol. 1764, no. 9, pp. 1470-1478.
135. Primo-Parmo, S.L., Sorenson, R.C., Teiber, J., and La Du, B.N. 1996, “The human serumparaoxonase/arylesterase gene (PON1) is one member of a multigene family, " Genomics, vol. 33, no. 3, pp. 498-507.
136. Raveh, L., Grunwald, J., Marcus, D., Papier, Y., Cohen, E., and Ashani, Y. 1993, “Human butyrylcholinesterase as a general prophylactic antidote for nerve agent toxicity. In vitro and in vivo quantitative characterization, " Biochem. Pharmacol., vol. 45, no. 12, pp. 2465-2474.
137. Raveh, L., Grauer, E., Grunwald, J., Cohen, E., and Ashani, Y. 1997, “The stoichiometry of protection against soman and VX toxicity in monkeys pretreated with human butyrylcholinesterase, " Toxicol. Appl.Pharmacol., vol. 145, no. 1, pp. 43-53.
138. Robbi, M. and Beaufay, H. 1992, “Topogenesis of carboxylesterases: a rat liver isoenzyme ending in -HTEHTCOOH is a secreted protein, " Biochem. Biophys. Res. Commun., vol. 183, no. 2, pp. 836-841.
139. Robbi, M., Beaufay, H., and Octave, J.N. 1990, “Nucleotide sequence of cDNA coding for rat liver pI 6.1 esterase (ES-10), a carboxylesterase located in the lumen of the endoplasmic reticulum, " Biochem. J., vol. 269, no. 2, pp. 451-458.
140. Rochu, D., Chabrieres, E., and Masson, P. 2007, “Human paraoxonase: a promising approach for pre-treatment and therapy of organophosphorus poisoning, " Toxicology, vol. 233, no. 1-3, pp. 47-59.
141. Rodrigo, L., Mackness, B., Durrington, P.N., Hernandez, A., and Mackness, M.I. 2001, “Hydrolysis of platelet-activating factor by human serum paraoxonase, " Biochem. J., vol. 354, no. Pt 1, pp. 1-7.
142. Rosenblat, M., Gaidukov, L., Khersonsky, O., Vaya, J., Oren, R., Tawfik, D.S., and Aviram, M. 2006, “The catalytic histidine dyad of high density lipoprotein-associated serum paraoxonase-1 (PON1) is essential for PON1-mediated inhibition of low density lipoprotein oxidation and stimulation of macrophage cholesterol efflux, " J. Biol. Chem., vol. 281, pp. 7657-7665.
143. Satoh, T. 1987, “Role of carboxylesterases in xenobiotic metabolism, " in Reviews in Biological Toxicology, vol. 8 E. Hodgsen, J.R. Bend, and R.M. Philpot, eds., Elsevier, New York, p. 155.
144. Satoh, T. and Hosokawa, M. 1998, “The mammalian carboxylesterases: from molecules to functions, " Annu. Rev. Pharmacol. Toxicol., vol. 38, pp. 257-288.
145. Satoh, T. and Hosokawa, M. 2006, “Structure, function and regulation of carboxylesterases, " Chem. Biol.Interact., vol. 162, no. 3, pp. 195-211.
146. Saxena, A. 2002, “Human Serum Butyrylcholinesterase: A Future Generation Antidote for Organophosphate Chemical Warfare Agent Toxicity, " Proceedings of the Seventh International meeting on cholinesterases, Pucon, Chile.
147. Saxena, A., Sun, W., Luo, C., and Doctor, B.P. 2005, “Human serum butyrylcholinesterase: in vitro and in vivo stability, pharmacokinetics, and safety in mice, " Chem. Biol. Interact., vol. 157-158, pp. 199-203.
148. Schwer, H., Langmann, T., Daig, R., Becker, A., Aslanidis, C., and Schmitz, G. 1997, “Molecular cloning and characterization of a novel putative carboxylesterase, present in human intestine and liver, " Biochem.Biophys. Res. Commun., vol. 233, no. 1, pp. 117-120.
149. Serdar, C.M. and Gibson, D.T. 1985, “Enzymatic hydrolysis of organophosphates: cloning and expression of a parathion hydrolase gene from Pseudomonas diminuta, " Biotechnology, vol. 3, p. 567.
150. Shibata, F., Takagi, Y., Kitajima, M., Kuroda, T., and Omura, T. 1993, “Molecular cloning and characterization of a human carboxylesterase gene, " Genomics, vol. 17, p. 76.
151. Shih, D.M., Gu, L., Xia, Y.R., Navab, M., Li, W.F., Hama, S., Castellani, L.W., Furlong, C.E., Costa, L.G., Fogelman, A.M., and Lusis, A.J. 1998, “Mice lacking serum paraoxonase are susceptible to organophosphate toxicity and atherosclerosis, " Nature, vol. 394, no. 6690, pp. 284-287.
152. Sidell, F.R. and Groff, W.A. 1970, “Toxogonin: blood levels and side effects after intramuscular administration in man, " J. Pharm. Sci., vol. 59, no. 6, pp. 793-797.
153. Siritunga, D. and Sayre, R.T. 2003, “Generation of cyanogen-free transgenic cassava, " Planta, vol. 217, no. 3, pp. 367-373.
154. Somani, S.M., Solana, R.P., and Dube, S.N. 1992, “Toxiodynamics of nerve agents, " in Chemical Warfare Agents, S.M. Somani, ed., Academic Press, San Diego, CA, p. 68.
155. Sone, T., Isobe, M., Takabatake, E., and Wang, C.Y. 1994, “Cloning and sequence analysis of a hamster liver cDNA encoding a novel putative carboxylesterase, " Biochim. Biophys. Acta, vol. 1207, no. 1, pp. 138-142.
156. Sorenson, R.C., Primo-Parmo, S.L., Kuo, C.L., Adkins, S., Lockridge, O., and La Du, B.N. 1995, “Reconsideration of the catalytic center and mechanism of mammalian paraoxonase/arylesterase, " Proc. Natl.Acad. Sci. U.S. A., vol. 92, no. 16, pp. 7187-7191.
157. Sorenson, R.C., Bisgaier, C.L., Aviram, M., Hsu, C., Billecke, S., and La Du, B.N. 1999, “Human serum Paraoxonase/Arylesterase’s retained hydrophobic N-terminal leader sequence associates with HDLs by binding phospholipids: apolipoprotein A-I stabilizes activity, " Arterioscler. Thromb. Vasc. Biol., vol. 19, no. 9, pp. 2214-2225.
158. Stewart, W.C. 1959, “The effects of sarin and atropine on the respiratory center and neuromuscular junctions of the rat, " Can. J. Biochem. Physiol., vol. 37, no. 5, pp. 651-660.
159. Stewart, W.C. and Anderson, E.A. 1968, “Effect of a cholinesterase inhibitor when injected into the medulla of the rabbit, " J. Pharmacol. Exp. Ther., vol. 162, no. 2, pp. 309-318.
160. Talbot, B.G., Anderson, D.R., Harris, L.W., Yarbrough, L.W., and Lennox, W.J. 1988, “A comparison of in vivo and in vitro rates of aging of soman-inhibited erythrocyte acetylcholinesterase in different animal species, " Drug Chem. Toxicol., vol. 11, no. 3, pp. 289-305.
161. Taylor, P. 2001a, “Agents acting at the neuromuscular junction and autonomic ganglia, " in Goodman and Gilman’s The Pharmacological Basis of Therapeutics, 10th edn, J.G. Hardman, L.E. Limbird, and A.G.Gilman, eds., McGraw-Hill, New York, pp. 193-214.
162. Taylor, P. 2001b, “Anticholinesterase agents, " in Goodman and Gillman’s The Pharmacological Basis of Therapeutics, 10th edn, J.G. Hardman and L.E. Limbird, eds., Macmillan Publishing Company, New York, pp. 175-192.
163. Teiber, J.F., Draganov, D.I., and La Du, B.N. 2003, “Lactonase and lactonizing activities of human serum paraoxonase (PON1) and rabbit serum PON3, " Biochem. Pharmacol., vol. 66, no. 6, pp. 887-896.
164. Tuovinen, K., Kaliste-Korhonen, E., Raushel, F.M., and Hanninen, O. 1999, “Success of pyridostigmine, physostigmine, eptastigmine and phosphotriesterase treatments in acute sarin intoxication, " Toxicology, vol. 134, no. 2-3, pp. 169-178.
165. van Himbergen, T.M., van Tits, L.J., Roest, M., and Stalenhoef, A.F. 2006, “The story of PON1: how an organophosphate-hydrolysing enzyme is becoming a player in cardiovascular medicine, " Neth. J. Med., vol. 64, no. 2, pp. 34-38.
166. Vojvodic, V. 1970, “Blood levels, urinary excretion and potential toxicity of N, N 0-trimethylenebis(pyridinium-4-aldoxime) dichloride (TMB-4) in healthy man following intramuscular injection of oxime, " Eur.J. Clin. Pharmacol., vol. 2, p. 216.
167. Welch, R.W., Campbell, J., Toledo, A., Davis, D., Latzgo, H., Haupt, G., Love, K., Sly, J.M., Cohen, G., Eisenberg, R., Whitbeck, J.C., Aldaz-Carroll, L., Lou, H., Lenz, D.E., Patel, P., and Cerasoli, D. 2006, “Rapid production of recombinant proteins utilizing the PERLXpress platform, " Bioprocessing J., vol. 5, no. 2, pp. 63-70.
168. Wenger, G.R. 1979, “Effects of physostigmine, atropine and scopolamine on behavior maintained by a multiple schedule of food presentation in the mouse, " J. Pharmacol. Exp. Ther., vol. 209, no. 1, pp. 137-143.
169. Wiezorek, W., Kreisel, W., Schnitzlein, W., and Matzkowski, H. 1968, “Eigenwirkungen von trimedoxin und pralidoxim am menschen, " Zeitschr. Militarmed., vol. 4, p. 223.
170. Wolfe, A.D., Rush, R.S., Doctor, B.P., Koplovitz, I., and Jones, D. 1987, “Acetylcholinesterase prophylaxis against organophosphate toxicity, " Fundam. Appl. Toxicol., vol. 9, no. 2, pp. 266-270.
171. Wolfe, A.D., Blick, D.W., Murphy, M.R., Millers, S.A., Gentry, M.K., Hartgraves, S.L., and Doctor, B.P. 1992, “Use of cholinesterases as pretreatment drugs for the protection of rhesus monkeys against soman toxicity, " Toxicol. Appl. Pharmacol., vol. 117, no. 2, pp. 189-193.
172. Xiong, L. and Sayre, R.T. 2004, “Engineering the chloroplast encoded proteins of chlamydomonas, " Photosynth.Res., vol. 80, no. 1-3, pp. 411-419.
173. Yan, B., Yang, D., Brady, M., and Parkinson, A. 1994, “Rat kidney carboxylesterase. Cloning, sequencing, cellular localization, and relationship to rat liver hydrolase, " J. Biol. Chem., vol. 269, no. 47, pp. 29688-29696.
174. Yeung, D.T., Josse, D., Nicholson, J.D., Khanal, A., McAndrew, C.W., Bahnson, B.J., Lenz, D.E., and Cerasoli, D.M. 2004, “Structure/function analyses of human serum paraoxonase (HuPON1) mutants designed from a DFPase-like homology model, " Biochim. Biophys. Acta, vol. 1702, no. 1, pp. 67-77.
175. Yeung, D.T., Lenz, D.E., and Cerasoli, D.M. 2005, “Analysis of active-site amino-acid residues of human serum paraoxonase using competitive substrates, " FEBS J., vol. 272, no. 9, pp. 2225-2230.
176. Yeung, D.T., Smith, J.R., Sweeney, R.E., Lenz, D.E., and Cerasoli, D. 2006, “Direct detection of stereospecific soman (GD) hydrolysis by wild-type human serum paraoxonase (HuPON1), " FEBS J.
177. Yli-Kauhaluoma, J., Humppi, T., and Yliniemela, A. 1999, “Hydrolysis of organophosphorus nerve agent soman by the monoclonal antibodies elicited against an oxyphosphorane hapten, " Acta Chem. Scand., vol. 53, pp. 473-479.