Toxicokinetics of chemical warfare agents: Nerve agents and vesicants

Handbook of Toxicology of Chemical Warfare Agents

Volumn , Issue , 2009, Pages 755-790

  John, Harald ^a   Balszuweit, Frank ^a   Kehe, Kai ^a   Worek, Franz ^a   Thiermann, Horst ^a  

^a BUNDESWEHR INSTITUTE OF PHARMACOLOGY AND TOXICOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84859042198     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-012374484-5.00050-X     Document Type: Chapter

References (202)

1. Amitai G., Gaidukov L., Adani R., Yishay S., Yacov G., Kushnir M., Teitlboim S., Lindenbaum M., Bel P., Khersonsky O., Tawfik D.S., Meshulam H. Enhanced stereoselective hydrolysis of toxic OPs by directly evolved variants of mammalian serum paraoxonase. FEBS J. 2006, 273:1906-1919.
2. ATSDR -Agency for Toxic Substances and Disease Registry (2007). Blister Agents. Department of Health and Human Services. Atlanta, GA.
3. Augerson, W. (2000). A review of the scientific literature as it pertains to Gulf War illness, Vol. 5: Chemical and Biological Warfare Agents (W. Augerson, ed.), pp. 99-189. RAND Corp. RAND National Security Research Division and RAND Health, Santa Monica, CA, USA.
4. Aurbek N., Thiermann H., Szinicz L., Eyer P., Worek F. Analysis of inhibition, reactivation and aging kinetics of highly toxic OP compounds with human and pig cholinesterase. Toxicology 2006, 224:91-99.
5. Bakry N.M.S., El-Rashidy A.H., Eldefrawi A.T., Eldefrawi M.E. Direct actions of organophosphate anticholinesterases on nicotinic and muscarinic acetylcholine receptors. J. Biochem. Toxicol. 1988, 3:235-259.
6. Balali-Mood M., Balali-Mood K. Neurotoxic disorders of OP compounds and their management. Arch. Iranian Med. 2008, 11:65-89.
7. Balali-Mood M., Hefazi M. The pharmacology, toxicology, and medical treatment of sulphur mustard poisoning. Fundam. Clin. Pharmacol. 2005, 19:297-315.
8. Balali-Mood, M., Navaeian, A. (1986). Clinical and paraclinical findings in 233 patients with sulphur mustard poisoning. In Proceedings of the Second World Congress on New Compounds in Biological and Chemical Warfare, Vol. 1 (B. Heyndrickx, ed.), pp. 464-73. Rijksuniversiteit, Ghent, Belgium.
9. Barr J.R., Pierce C.L., Smith J.R., Capacio B.R., Woolfitt A.R., Solano M.I., Wooten J.V., Lemire S.W., Thomas J.D., Ash D.H., Ashley D.L. Analysis of urinary metabolites of sulfur mustard in two individuals after accidental exposure. J. Anal. Toxicol. 2008, 32:10-16.
10. Bartling A., Worek F., Szinicz L., Thiermann H. Enzyme-kinetic investigation of different sarin analogues reacting with human acetylcholinesterase and butyrylcholinesterase. Toxicology 2007, 233:166-172.
11. Benschop H.P., de Jong L.P.A. Nerve agent stereoisomers: analysis, isolation, and toxicology. Acc. Chem. Res. 1988, 21:368-374.
12. Benschop H.P., de Jong L.P.A. Toxicokinetics of nerve agents. Chemical Warfare Agents: Toxicity at Low Levels 2001, 25-81. CRC Press LLC, Boca Raton, FL. S.M. Somani, J.A. Romano (Eds.).
13. Benschop H.P., Konings C.A.G., de Jong L.P.A. Gas chromatographic separation and identification of the four stereoisomers of 1,2,2-trimethylpropyl methylphosphonofluoridate (soman). Stereospecificity of in vitro "detoxification' reactions. J. Am. Chem. Soc. 1981, 103:4260-4262.
14. Benschop H.P., Bijleveld E.C., Otto M.F., Degenhardt C.E.A.M., Van Helden H.P.M., de Jong L.P.A. Stabilization and gas chromatographic analysis of the four stereoisomers of 1,2,2-triemethylpropyl methylphosphonofluoridate (soman) in rat blood. Anal. Biochem. 1985, 151:242-253.
15. Billecke S.S., Primo-Parmo S.L., Dunlop C.S., Doorn J.A., La Du B.N., Broomfield C.A. Characterization of a soluble mouse liver enzyme capable of hydrolyzing diisopropyl phosphorofluoridate. Chem. Biol. Interact. 1999, 119-20:251-256.
16. Billecke S., Draganov D., Counsell R., Stetson P., Watson C., Hsu C., La Du B.N. Human serum paraoxonase (PON1) isozymes Q and R hydrolyze lactones and cyclic carbonate esters. Drug Metab. Dispos. 2000, 28:1335-1342.
17. Black R.M., Read R.W. Methods for the analysis of thiodiglycol sulphoxide, a metabolite of sulphur mustard, in urine using gas chromatography-mass spectrometry. J. Chromatogr. 1991, 558:393-404.
18. Black R.M., Read R.W. Biological fate of sulphur mustard, 1,10-thiobis(2-chloroethane): identification of beta-lyase metabolites and hydrolysis products in human urine. Xenobiotica 1995, 25:167-173.
19. Black, R.M., Harrison, J.M., Read, R.W. (1997a). Biological fate of sulfur mustard: in vitro alkylation of human haemoglobin by sulfur mustard. Xenobiotica27: 11-32.
20. Black, R.M., Clarke, R.J., Harrison, J.M., Read, R.W. (1997b). Biological fate of sulfur mustard: identification of valine and histidine adducts in haemoglobin from casualties of sulfur mustard poisoning. Xenobiotica27: 499-512.
21. Black R.M., Harrison J.M., Read R.W. The interaction of sarin and soman with plasma proteins: the identification of a novel phosphonylation site. Arch. Toxicol. 1999, 73:123-126.
22. Blank I.H., Griesener R.D., Gould E. The penetration of an anticholinesterase agent (sarin) into skin. J. Invest. Dermatol. 1957, 29:299-309.
23. Blum M.M., Richardt A. Hydrolytic enzymes for chemical warfare agent decontamination. Decontamination of Warfare Agents 2008, 135-162. Wiley-VCH, Weinheim. A. Richardt, M.M. Blum (Eds.).
24. Blum M.M., Löhr F., Richardt A., Rüterjans H., Chen J.C.H. Binding of a designed substrate analogue to diisopropyl fluorophosphatase: implications for the phosphotriesterase mechanism. J. Am. Chem. Soc. 2006, 128:12750-12757.
25. Bossle P.C., Ellzy M.W., Martin J.J. Determination of L1 contamination in environmental waters by high performance liquid chromatography. Technical Report CRDEC-TR-042, AD-A206 000/2 1989.
26. Brank M., Zajc-Kreft K., Kreft S., Komel R., Grubic Z. Biogenesis of acetylcholinesterase is impaired, although its mRNA level remains normal, in the glucocorticoid-treated rat skeletal muscle. Eur. J. Biochem. 1998, 251:374-381.
27. Butler A.M., Murray M. Biotransformation of parathion in human liver: participation of CYP3A4 and its activation during microsomal parathion oxidation. J. Pharmacol. Exp. Ther. 1997, 280:966-973.
28. Cahn R.S., Ingold C., Prelog V. Spezifikation der molekularen Chiralität. Angew. Chem. 1966, 78:413-447.
29. Carol-Visser J., Van der Schans M., Fidder A., Hulst A.G., Van Baar B.L.M., Irth H., Noort D. Development of an automated on-line pepsin digestion-liquid chromatography-tandem mass spectrometry configuration for the rapid analysis of protein adducts of chemical warfare agents. J. Chromatogr. B 2008, 870:91-97.
30. Casida J.E., Quistad G.B. Serine hydrolase targets of OP toxicants. Chem. Biol. Interact. 2005, 157-8:277-283.
31. Chilcott R.P., Jenner J., Carrick W., Hotchkiss S.A., Rice P. Human skin absorption of bis-2-(chloroethyl)sulphide (sulphur mustard) in vitro. J. Appl. Toxicol. 2000, 20:349-355.
32. Chilcott R.P., Jenner J., Hotchkiss S.A., Rice P. In vitro skin absorption and decontamination of sulphur mustard: comparison of human and pig-ear skin. J. Appl. Toxicol. 2001, 21:279-283.
33. Chilcott R.P., Jenner J., Hotchkiss S.A., Rice P. Evaluation of barrier creams against sulphur mustard. I. In vitro studies using human skin. Skin Pharmacol. Appl. Skin Physiol. 2002, 15:225-235.
34. Chilcott R.P., Dalton C.H., Hill I., Davison C.M., Blohm K.L., Hamilton M.G. Clinical manifestations of VX poisoning following percutaneous exposure in the domestic white pig. Hum. Exp. Toxicol. 2003, 22:255-261.
35. Chilcott R.P., Dalton C.H., Hill I., Davison C.M., Blohm K.L., Clarkson E.D., Hamilton M.G. In vivo skin absorption and distribution of the nerve agent VX (O-ethyl-S-[2(diisopropylamino)ethyl]methylphosphonothioate) in the domestic white pig. Hum. Exp. Toxicol. 2005, 24:347-352.
36. Chilukuri N., Parikh K., Sun W., Naik R., Tipparaju P., Doctor B.P., Saxena A. Polyethylene glycosylation prolongs the circulatory stability of recombinant human butyrylcholinesterase. Chem. Biol. Interact. 2005, 157-8:115-121.
37. Committee on Gulf War and Health (2004). Gulf War and Health: updated literature review of sarin. The National Academic Press, Washington, DC. http://www.nap.edu/catalog/11064.html.
38. Committee on Health Effects Associated with Exposures during the Gulf War, Division of Health Promotion and Disease Prevention, Institute of Medicine of the National Academies (2000). Gulf War and Health: Vol. 1. Depleted Uranium, Pyridostigmine Bromide, Sarin, and Vaccines (C.E. Fulco, C.T. Liverman, H.C. Sox, eds). National Academies Press, Washington, DC. http://www.nap.edu/catalog.php%3Frecord_id%3D9953.
39. Costa L.G. Current issues in organophosphate toxicology. Clin. Chim. Acta 2006, 366:1-13.
40. Czerwinski S.E., Maxwell D.M., Lenz D.E. A method for measuring octanol:water partition coefficients of highly toxic OP compounds. Toxicol. Methods 1998, 8:139-149.
41. Czerwinski S.E., Skvorak J.P., Maxwell D.M., Lenz D.E., Baskin S.I. Effect of octanol:water partition coefficients of OP compounds on biodistribution and percutaneous toxicity. J. Biochem. Mol. Toxicol. 2006, 20:241-246.
42. Dabisch P.A., Horsmon M.S., Taylor J.T., Muse W.T., Miller D.B., Sommerville D.R., Mioduszewski R.J., Thomson S. Gender difference in the miotic potency of soman vapor in rats. Cutan. Ocul. Toxicol. 2008, 27:123-133.
43. Dacre J.C., Goldman M. Toxicology and pharmacology of the chemical warfare agent sulfur mustard. Pharmacol. Rev. 1996, 48:289-326.
44. Dalton C.H., Hattersley I.J., Rutter S.J., Chilcott R.P. Absorption of the nerve agent VX (O-ethyl-S-[2(di-isopropylamino)ethyl] methyl phosphonothioate) through pig, human and guinea pig skin in vitro. Toxicol. Vitro 2006, 20:1532-1536.
45. Daly J.D., O'Hehir C.M. A sensitive method for quantitation of beta-lyase metabolites of sulfur mustard as 1,10-sulfonylbis[2-(methylthio)ethane] (SBMTE) in human urine by isotope dilution liquid chromatography-positive ion-electrospray-tandem mass spectrometry. J. Chromatogr. B 2007, 850:120-127.
46. Davies H.G., Richter R.J., Keifer M., Broomfield C.A., Sowalla J., Furlong C.E. The effect of the human serum paraoxonase polymorphism is reversed with diazoxon, soman and sarin. Nat. Genet. 1996, 14:334-336.
47. Delaunois A., Gustin P., Ansay M. Altered capillary filtration coefficient in parathion-and paraoxon-induced edema in isolated and perfused rabbit lungs. Toxicol. Appl. Pharmacol. 1992, 116:161-169.
48. Dorandeu F., Foquin A., Briot R., Delacour C., Denis J., Alonso A., Froment M.T., Renault F., Lallement G., Masson P. An unexpected plasma cholinesterase activity rebound after challenge with a high dose of the nerve agent VX. Toxicology 2008, 248:151-157.
49. Dragonov D.I., La Du B.N. Pharmacogenetics of paraoxonases: a brief review. Nauyn-Schmiedebergs Arch. Pharmacol. 2004, 369:78-88.
50. Drasch G., Kretschmer G., Kauert L., Von Meyer L. Concentration of mustard gas [bis(2-chloroethyl)sulfide] in the tissues of a victim of a vesicant exposure. J. Forensic Sci. 1987, 32:1788-1793.
51. Due A.H., Trap H.C., Van der Wiel H.J., Benschop H.P. Effect of pretreatment with CBDP on the toxicokinetics of soman stereoisomers in rats and guinea pigs. Arch. Toxicol. 1993, 67:706-711.
52. Duffy F.H., Burchfiel J.L., Bartels P.H., Gaon M., Sim V.M. Long-term effects of an organophosphate upon the human electroencephalogram. Toxicol. Appl. Pharmacol. 1979, 47:161-176.
53. Duysen E.G., Li B., Xie W., Schopfer L.M., Anderson R.S., Broomfield C.A., Lockridge O. Evidence of nonacetylcholinesterase targets of OP nerve agent: supersensitivity of acetylcholinesterase knockout mouse to VX lethality. J. Pharmacol. Exp. Ther. 2001, 299:528-535.
54. Eddleston, M., Eyer, P., Worek, F., Rezvi Sheriff, M.H., Buckley, N.A. (2008a). Predicting outcome using butyrylcholinesterase activity in OP pesticide self-poisoning. QJM101: 467-74.
55. Eddleston, M., Buckley, N.A., Eyer, P., Dawson, A.H. (2008b). Management of acute OP pesticide poisoning. Lancet371: 597-607.
56. Eddleston M., Eyer P., Worek F., Mohammed F., Senarathna L., Von Meyer L., Juszczak E., Hittarage A., Azher S., Dissanayake W., SheriffM.H.R., Szinicz L., Dawson A.H., Buckley N.A. Differences between OP insecticides in human self-poisoning. Lancet 2005, 366:1452-1459.
57. Elhanany E., Ordentlich A., Dgany O., Kaplan D., Segall Y., Barak R., Velan Y., Shafferman A. Resolving pathways of interaction of covalent inhibitors with the active site of acetylcholinesterase: MALDI-TOF/MS analysis of various nerve agent phosphyl adducts. Chem. Res. Toxicol. 2001, 14(7):912-918.
58. Fidder A., Moes G.W., Scheffer A.G., Van der Schans G.P., Baan R.A., de Jong L.P., Benschop H.P. Synthesis, characterization, and quantitation of the major adducts formed between sulfur mustard and DNA of calf thymus and human blood. Chem. Res. Toxicol 1994, 7:199-204.
59. Fidder, A., Noort, D., de Jong, L.P., Benschop, H.P., Hulst, A.G. (1996a). N7-(2-hydroxyethylthioethyl)-guanine: a novel urinary metabolite following exposure to sulphur mustard. Arch. Toxicol.70: 854-5.
60. Fidder, A., Noort, D., de Jong, A.L., Trap, H.C., de Jong, L.P.A., Benschop, H.P. (1996b). Monitoring of in vitro and in vivo exposure to sulfur mustard by GC/MS determination of the N-terminal valine adduct in hemoglobin after a modified Edman degradation. Chem. Res. Toxicol.9: 788-92.
61. Fidder A., Noort D., Hulst A.G., de Jong L.P., Benschop H.P. Biomonitoring of exposure to lewisite based on adducts to haemoglobin. Arch. Toxicol. 2000, 74:207-214.
62. Fowler W.K., Stewart D.C., Weinberg D.S., Sarver E.W. Gas chromatographic determination of lewisite hydrolysate. 2-chlorovinylarsonous acid, after derivatization with 1,2-ethanedithiol J. Chromatogr. 1991, 558:235-243.
63. Franke S. Lehrbuch der Militärchemie, Band 1 1977, Militärverlag der Deutschen Demokratischen Republik, Berlin. S. Franke (Ed.).
64. Franz T.J. Percutaneous absorption. On the relevance of in vitro data. J. Invest. Dermatol. 1975, 64:190-195.
65. Fredriksson, T. (1958). Studies on the percutaneous absorption of sarin and two allied OP cholinesterase inhibitors. Acta Derm. Venerol.38 (Suppl. 41): 1-83.
66. Fujikawa Y., Satoh T., Suganuma A., Suzuki S., Niikura Y., Yui S., Yamaura Y. Extremely sensitive biomarker of acute OP insecticide exposure. Hum. Exp. Toxicol. 2005, 24:333-336.
67. Furlong C.E. Genetic variability in the cytochrom P450-paraoxonase 1 (PON1) pathway for detoxification of OP compounds. J. Biochem. Mol. Toxicol. 2007, 21:197-205.
68. Ghanem E., Raushel F.M. Detoxification of organophosphate nerve agents by bacterial phosphotriesterase. Toxicol. Appl. Pharmacol. 2005, 207:S459-S470.
69. Goldman M., Dacre J.C. Lewisite: its chemistry, toxicology, and biological effects. Rev. Environ. Contam. Toxicol. 1989, 110:75-115.
70. Goodman L.S., Wintrobe M.M., Dameshek W., Goodman M.J., Gilman A., McLennan M.T. Landmark article Sept. 21, 1946: nitrogen mustard therapy. Use of methyl-bis(beta-chloroethyl)amine hydrochloride and tris(beta-chloroethyl)amine hydrochloride for Hodgkin's disease, lymphosarcoma, leukemia and certain allied and miscellaneous disorders. JAMA 1984, 251:2255-2261.
71. Göransson-Nyberg A., Fredriksson S.A., Karlsson B., Lundström M., Cassel G. Toxicokinetics of soman in cerebrospinal fluid and blood of anaesthetized pigs. Arch. Toxicol. 1998, 72:459-467.
72. Gordon J.J., Inns R.H., Johnson M.K., Leadbeater L., Maidment M.P., Upshall D.G., Cooper G.H., Rickard R.L. The delayed neuropathic effects of nerve agents and some other OP compounds. Arch. Toxicol. 1983, 52:71-82.
73. Graham J.S., Reid F.M., Smith J.R., Stotts R.R., Tucker E.S., Shumaker S.M., Niemuth N.A., Janny S.J. A cutaneous full-thickness liquid sulfur mustard burn model in weanling swine: clinical pathology and urinary excretion of thiodiglycol. J. Appl. Toxicol. 2000, 20:161-172.
74. Graham, J.S., Stevenson, R.S., Mitcheltree, L.W., Hamilton, T.A., Deckert, R.R., Lee, R.B., Schiavetta, A.M. (2008). Concepts in the surgical management of sulfur mustard injuries. 11th Medical Chemical Defence Conference, Munich, Germany.
75. Grubić Z., Sketelj J., Klinar B., Brzin M. Recovery of acetylcholinesterase in the diaphragm, brain, and plasma of the rat after irreversible inhibition by soman: a study of cytochemical localization and molecular forms of the enzyme in the motor end plate. J. Neurochem. 1981, 37:909-916.
76. Hanaoka S., Nomura K., Wada T. Determination of mustard and lewisite related compounds in abandoned chemical weapons (yellow shells) from sources in China and Japan. J. Chromatogr. A 2006, 1101:268-277.
77. Hooijschuur E.W.J., Kientz C.E., Brinkman U.A.T. Analytical separation techniques for the determination of chemical warfare agents. J. Chromatogr. A 2002, 982:177-200.
78. Hosokawa M., Satoh T. Structure, function, and regulation of carboxylesterases. Toxicology of Organophosphate and Carbamate Compounds 2006, 219-231. Academic Press/Elsevier, Amsterdam. R.C. Gupta (Ed.).
79. Huang, Y.S., Huang, Y., Baldasssarre, H., Wang, B., Lazaris, A., Leduc, M., Bilodeau, A.S., Bellemare, A., Cote, M., Herskovits, P., Touati, M., Turcotte, C., Valeanu, L., Lemee, 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., Langermann, S. (2007). Recombinant human butyrylcholinesterase from milk of transgenic animals to protect against organophosphate poisoning. Proc. Natl Acad. Sci. USA104: 13603-8.
80. Huang, Y.S., Lundy, P.M., Lataris, A., Huang, Y., Baldasssarre, 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., Langermann, S. (2008). Substantially improved pharmacokinetics of recombinant human butyrylcholinesterase by fusion to human serum albumin. BMC Biotechnol. (In press) (doi: 10.1186/1472-6750-8-50).
81. Inayat-Hussain, S., Lubis, S.H., Sakian, N.I.M., Ghazali, A.R., Ali, N.S., el Sersi, M., Toong, L.M., Zainal, A.M., Hashim, S., Ghazali, M.S., Saidin, M.N., Ab Rahman, A.R., Rafaai, M.J.M., Omar, S., Rapiai, R., Othman, R., Chan, L.T., Johari, A., Soon, W.H., Salleh, A.R., Satoh, T. (2007). Is plasma β-glucuronidase a novel human biomarker for monitoring anticholinestrease pesticides exposure? A Malaysian experience. Toxicol. Appl. Pharmacol.219: 210-16.
82. Inns R.H., Rice P. Efficacy of dimercapto chelating agents for the treatment of poisoning by percutaneously applied dichloro(2-chlorovinyl)arsine in rabbits. Hum. Exp. Toxicol. 1993, 12:241-246.
83. Inns R.H., Rice P., Bright J.E., Marrs T.C. Evaluation of the efficacy of dimercapto chelating agents for the treatment of systemic organic arsenic poisoning in rabbits. Hum. Exp. Toxicol. 1990, 9:215-220.
84. Jakubowski E.M., Smith J.R., Logan T.P., Wiltshire N., Woodward C.L. Verification of lewisite exposure: quantification of chlorovinylarsonous acid in biological samples. Proceedings 1993 Medical Defense Bioscience Review, United States Army Medical Research and Material Command 1993, 361-368.
85. a of 12-S-hydroxyheptadecatrienoic acid by studies of its vial surface adsorption using high-performance liquid chromatography and liquid scintillation technique. Chem. Phys. Lipids 1999, 99:95-101.
86. John H., Walden M., Schäfer S., Genz S., Forssmann W.G. Analytical procedures for quantification of peptides in pharmaceutical research by liquid chromatography mass spectrometry. Anal. Bioanal. Chem. 2004, 378:883-897.
87. John H., Radtke K., Ständker L., Forssmann W.G. Identification and characterization of novel endogenous proteolytic forms of the human angiogenesis inhibitors restin and endostatin. Biochim. Biophys. Acta 2005, 1747:161-170.
88. John H., Worek F., Thiermann H. LC-MS based procedures for monitoring of toxic OP compounds and the verification of pesticide and nerve agent poisoning. Anal. Bioanal. Chem. 2008, 391:97-116.
89. Kehe K., Szinicz L. Medical aspects of sulphur mustard poisoning. Toxicology 2005, 214:198-209.
90. Kiderlen D., Eyer P., Worek F. Formation and disposition of diethylphosphoryl-obidoxime, a potent anticholinesterase that is hydrolyzed by human paraoxonase. Biochem. Pharmacol. 2005, 69:1853-1867.
91. Koelle G.B. Handbuch der Experimentellen Pharmkologie, Band 15, Cholinesterases and Anticholinesterase Agents 1963, Springer-Verlag, Berlin. O. Eichler, A. Farah, G.B. Koelle (Eds.).
92. Kolarich D., Weber A., Pabst M., Stadlmann J., Teschner W., Ehrlich H., Schwarz H.P., Altmann F. Glycoproteomic characterization of butyrylcholinesterase from human plasma. Proteomics 2008, 8:254-263.
93. Kondo Y., Ishigami A., Kubo S., Handa S., Gomi K., Hirokawa K., Kajiyama N., Chiba T., Shimokado K., Maruyama N. Senescence marker protein-30 is a unique enzyme that hydrolyzes diisopropyl phosphorofluoridate in the liver. FEBS Lett. 2004, 570:57-62.
94. Lainee P., Robineau P., Guittin P., Coq H., Benchetrit G. Mechanism of pulmonary edema induced by an OP compound in anesthetized dogs. Fundam. Appl. Toxicol. 1991, 17:177-185.
95. Lama P.J. Systemic reactions associated with ophthalmic medications. Ophthalmol. Clin. North Am. 2005, 18:569-584.
96. Langenberg J.P., Van Dijk C., Sweeney R.E., Maxwell D.M., de Jong L.P.A., Benschop H.P. Development of a physiologically based model for the toxicokinetics of C()P()-soman in the atropinized guinea pig. Arch. Toxicol. 1997, 71:320-331.
97. Langenberg, J.P., Spruit, H.E.T., Van der Wiel, H.J., Trap, H.C., Helmich, R.B., Bergers, W.W.A., Van helden, H.P.M., Benschop, H.P. (1998a). Inhalation toxicokinetics of soman stereoisomers in the atropinized guinea pig with nose-only exposure to soman vapor. Toxicol. Appl. Pharmacol.151: 79-87.
98. Langenberg, J.P., Van der Schans, G.P., Spruit, H.E., Kuijpers, W.C., Mars-Groenendijk, R.H., Van Dijk-Knijnenburg, H.C., Trap, H.C., Van Helden, H.P., Benschop, H.P. (1998b). Toxicokinetics of sulfur mustard and its DNA-adducts in the hairless guinea pig. Drug Chem. Toxicol.21: 131-47.
99. Langford R.E. Introduction to Weapons of Mass Destruction: Radiological, Chemical, and Biological. Wiley-Interscience 2004, John Wiley & Sons, Hoboken, NJ. R.E. Langford (Ed.).
100. Lawrence, R.J., Smith, J.R., Boyd, B.L., Capacio, B.R. (2008). Improvements in the methodology of monitoring sulfur mustard exposure by gas chromatography-mass spectrometry analysis of cleaved and derivatized blood protein adducts. J. Anal. Toxicol.32: 31-6.
101. Lenz D.E., Yeung D., Smith J.R., Sweeney R.E., Lumley L.A., Cerasoli D.M. Stoichiometric and catalytic scavengers as protection against nerve agent toxicity: a mini review. Toxicology 2007, 233:31-39.
102. Levy A., Cohen G., Gilat E., Kapon J., Dachir S., Abraham S., Herskovitz M., Teitelbaum Z., Raveh L. Extrapolation from animal studies to the efficacy in humans of a pretreatment combination against organophosphate poisoning. Arch. Toxicol. 2007, 81:353-359.
103. Li B., Schopfer L.M., Hinrichs S.H., Masson P., Lockridge O. Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry assay for OP toxicants bound to human albumin Tyr411. Anal. Biochem. 2007, 361:263-272.
104. Li B., Nachon F., Froment M.T., Verdier L., Debouzy J.C., Brasme B., Gillon E., Schopfer L.M., Lockridge O., Masson P. Binding and hydrolysis of soman by human serum albumin. Chem. Res. Toxicol. 2008, 21:421-431.
105. Li J.T., Ruan J.X., Zhang Z.Q., Yuan S.L., Song Z.Y., Han D. Influence of portal vein and liver artery ligation on the toxicokinetics of soman in rabbits. Toxicol. Lett. 2002, 135:74-78.
106. Li, J.T., Ruan, X.J., Zhang, Z.Q., Yu W.D., Song, Z.Y., Qiao, J.Z. (2003a). Effects of pretreatment with verapamil on the toxicokinetics of soman in rabbits and distribution in mouse brain and diaphragm. Toxicol. Lett.138: 227-33.
107. Li, J.T., Ruan, J.X., Zhang, Z.Q., Yuan, S.L., Yu, W.D., Song, Z.Y. (2003b). Effects of pretreatment with 8018 on the toxicokinetics of soman in rabbits and distribution in mice. Life Sci.73: 1053-62.
108. Li W.S., Lum K.T., Chen-Goodspeed M., Sogorb M.A., Raushel F.M. Stereoselective detoxification of chiral sarin and soman analogues by phosphotriesterase. Bioorg. Med. Chem. 2001, 9:2083-2091.
109. 3H]sarin and its metabolites in mice. Toxicol. Appl. Pharmacol. 1986, 83:412-419.
110. Little J.S., Broomfield C.A., Fox-Talbot M.K., Boucher L.J., MacIver B., Lenz D.E. Partial characterization of an enzyme that hydrolyzes sarin, soman, tabun, and diisopropyl phosphorofluoridate (DFP). Biochem. Pharmacol. 1989, 38:23-29.
111. Lockridge O., Schopfer L.M., Winger G., Woods J.H. Large scale purification of butyrylcholinesterase from human plasma suitable for injection into monkeys; a potential new therapeutic for protection against cocaine and nerve agent toxicity. J. Med. CBR Def. 2005, 5:1-20.
112. Lodhi I.J., Sweeney J.F., Clift R.E., Hinshaw D.B. Nuclear dependence of sulfur mustard-mediated cell death. Toxicol. Appl. Pharmacol. 2001, 170:69-77.
113. Logan T.P., Smith J.R., Jakubowski E.M., Nielson R.E. Verification of lewisite exposure by analysis of 2-chloroarsonous acid in urine. Proceedings 1993 Medical Defense Bioscience Review, United States Army Medical Research and Material Command 1996, 923-934.
114. Logan T.P., Millard C.B., Shutz M., Schulz S.M., Lee R.B., Bongiovanni R. Cutaneous uptake of 14C-HD vapor by the hairless guinea pig. Drug Chem. Toxicol. 1999, 22:375-387.
115. Lorke D.E., Kalasz H., Petroianu G.A., Tekes K. Entry of oximes into the brain: a review. Curr. Med. Chem. 2008, 15:743-753.
116. Ludlum D.B., Kent S., Mehta J.R. Formation of O6-ethylthioethylguanine in DNA by reaction with the sulfur mustard, chloroethyl sulfide, and its apparent lack of repair by O6-alkylguanine-DNA alkyltransferase. Carcinogenesis 1986, 7:1203-1206.
117. Ludlum D.B., Austin-Ritchie P., Hagopian M., Niu T.Q., Yu D. Detection of sulfur mustard-induced DNA modifications. Chem. Biol. Interact. 1994, 91:39-49.
118. Maisonneuve A., Callebat I., Debordes L., Coppet L. Biological fate of sulphur mustard in rat: toxicokinetics and disposition. Xenobiotica 1993, 23:771-780.
119. Manoharan I., Boopathy R. Diisopropylflurophosphate-sensitive aryl acylamidase activity of fatty acid free human serum albumin. Arch. Biochem. Biophys. 2006, 452:186-188.
120. Marquardt H., Schäfer S., McClellan R., Welsch F. Toxicology 1999, Academic Press, San Diego, CA. H. Marquardt, S. Schäfer, R. McClellan, F. Welsch (Eds.).
121. Marrs T.C., Maynard R.L., Sidell F.R. Chemical Warfare Agents. Toxicology and Treatment 1996, 177. John Wiley & Sons, New York, NY. T.C. Marrs, R.L. Maynard, F. Sidell (Eds.).
122. Marrs T.C., Maynard R.L., Sidell F.R. Chemical Warfare Agents, Toxicology and Treatment 2007, John Wiley & Sons, Chichester, UK. 2nd edition. T.C. Marrs, R.L. Maynard, F.R. Sidell (Eds.).
123. Massoulie J. The origin of the molecular diversity and functional anchoring of cholinesterases. Neurosignals 2002, 11:130-143.
124. Maxwell D.M., Brecht K.M. The role of carboxylesterase in species variation of oxime protection against soman. Neurosci. Biobehav. Rev. 1991, 15:135-139.
125. Maxwell D.M., Brecht K.M. Carboxylesterase: specificity and spontaneous reactivation of an endogenous scavenger for OP compounds. J. Appl. Toxicol. 2001, 21:S103-S107.
126. Maxwell M., Brecht K.M., Koplovitz I., Sweeney R.E. Acetylcholinesterase inhibition: does it explain the toxicity of OP compounds?. Arch. Toxicol. 2006, 80:756-760.
127. Maynard R.L., Beswick F.W. OP compounds as chemical warfare agents. Clinical and Experimental Toxicology of OPs and Carbamates 1992, 373-385. Butterworth-Heinemann, Oxford. B. Ballantyne, T.C. Marrs, W.N. Aldridge (Eds.).
128. Minami M., Hui D.M., Katsumata M., Inagaki H., Boulet C.A. Method for the analysis of the methylphosphonic acid metabolites of sarin and its ethanol-substituted analogue in urine as applied to the victims of the Tokyo sarin disaster. J. Chromatogr. B 1997, 695:237-244.
129. Morita H., Yanagisawa N., Nakajima T., Shimizu M., Hirabayashi H., Okudera H., Nohara M., Midorikawa Y., Mimura S. Sarin poisoning in Matsumoto, Japan. Lancet 1995, 346:290-293.
130. Munro N.B., Talmage S.S., Griffin G.D., Waters L.C., Watson A.P., King J.F., Hauschild V. The sources, fate, and toxicity of chemical warfare agent degradation products. Environ. Health Perspect. 1999, 107:933-974.
131. Nieuwland J.A. Some Reactions of Acetylene 1904, (Dissertation.) Notre Dame Press, Notre Dame, IN, USA.
132. Niven A.S., Roop S.A. Inhalational exposure to nerve agents. Respir. Care Clin. N. Am. 2004, 10:59-74.
133. Nomura, D.K., Fujioka, K., Issa, R.S., Ward, A.M., Cravatt, B.F., Casina, J.E. (2008). Dual roles of brain serine hydrolase KIAA1363 in ether lipid metabolism and organophosphate detoxification. Toxicol. Appl. Pharmacol.228: 42-8.
134. Noort D., Verheij E.R., Hulst A.G., De Jong L.P.A., Benschop H.P. Characterization of sulfur mustard induced structural modifications in human hemoglobin by liquid chromatography-tandem mass spectrometry. Chem. Res. Toxicol 1996, 9:781-787.
135. Noort D., Hulst A.G., Trap H.C., de Jong L.P., Benschop H.P. Synthesis and mass spectrometric identification of the major amino acid adducts formed between sulphur mustard and haemoglobin in human blood. Arch Toxicol. 1997, 71:171-178.
136. Noort D., Hulst A.G., de Jong L.P., Benschop H.P. Alkylation of human serum albumin by sulfur mustard in vitro and in vivo: mass spectrometric analysis of a cysteine adduct as a sensitive biomarker of exposure. Chem. Res. Toxicol. 1999, 12:715-721.
137. Noort D., Benschop H.P., Black R.M. Biomonitoring of exposure to chemical warfare agents: a review. Toxicol. Appl. Pharmacol. 2002, 15:116-126.
138. Noort D., Fidder A., Van der Schans M.J., Hulst A.G. Verification of exposure to OPs: generic mass spectrometric method for detection of human butyrylcholinesterase adducts. Anal. Chem. 2006, 78:6640-6644.
139. Noort D., Fidder A., Degenhardt-Langelaan C.E., Hulst A.G. Retrospective detection of sulfur mustard exposure by mass spectrometric analysis of adducts to albumin and hemoglobin: an in vivo study. J. Anal. Toxicol. 2008, 32:25-30.
140. Nordgren I., Lundgren G., Puu G., Holmstedt B. Stereoselectivity of enzymes involved in toxicity and detoxification of soman. Arch. Toxicol. 1984, 55:70-75.
141. NRC, National Research Council (1982). Possible Long-Term Health Effects of Short-Term Exposure to Chemical Agents, Vol. 1: Anticholinesterases and Anticholinergics. National Academy Press, Washington, DC.
142. NRC, National Research Council (1985). Possible Long-Term Health Effects of Short-Term Exposure to Chemical Agents, Vol. 3: Final Report. Current Health Status of Test Subjects. National Academy Press, Washington, DC.
143. Oberst F.W., Crook J.W., Christensen M.K., Cresthull P., Koon W.S., Freeman G. Inhaled GB retention studies in man at rest and during activity 1959, Chemical Corps Research and Development Command, DTIC, Army Chemical Center, MD, AD226805.
144. Oberst F.W., Koon W.S., Christensen M.K., Crook J.W., Cresthull P., Freeman G. Retention of inhaled sarin vapor and its effects on red blood cell cholinesterase activity in man. Clin. Pharm. Ther. 1968, 9:421-427.
145. Okumura T., Takasu N., Ishimatsu S., Miyanoki S., Mitsuhashi A., Kumada K., Tanaka K., Hinohara S. Report on 640 victims of the Tokyo subway sarin attack. Ann. Emerg. Med. 1996, 28:129-135.
146. Okuno S., Sakurada K., Ohta H., Ikegaya H., Kazui Y., Akutsu T., Takatori T., Iwadate K. Blood-brain barrier penetration of novel pyridinealdoxime methiodide (PAM)-type oximes examined by brain microdialysis with LC-MS/MS. Toxicol. Appl. Pharmacol. 2008, 227:8-15.
147. Ordentlich A., Barak D., Kronman C., Benschop H.P., de Jong L.P.A., Ariel N., Barak R., Segall Y., Velan B., Shafferman A. Exploring the active center of human acetylcholinesterase with stereomers of an OP inhibitor with two chiral centers. Biochemistry 1999, 38:3055-3066.
148. Peeples E.S., Schopfer L.M., Duysen E.D., Spaulding R., Voelker T., Thompson C.M., Lockridge O. Albumin, a new biomarker of organophosphorus toxicant exposure, identified by mass spectrometry. Toxicol. Sci. 2005, 83:303-312.
149. Peters R.A. Biochemical research at Oxford upon mustard gas. Nature 1947, 159:149-151.
150. Pope C.N. OP pesticides: do they all have the same mechanism of toxicity?. J. Toxicol. Environ. Health, B Crit. Rev. 1999, 2:161-181.
151. Poulin P., Krishnan K. An algorithm for predicting tissue:blood partition coefficients of organic chemicals from n-octanol:water partition coefficient data. J. Toxicol. Environ. Health 1995, 46:117-129.
152. Prelog V., Helmchen G. Grundlagen des CIP-Systems und Vorschläge für eine Revision. Angew. Chem. 1982, 94:614-631.
153. Quin L.D. Optically active OP compounds. A Guide to OP Chemistry 2000, 272-307. Wiley-Interscience, New York, NY. L.D. Quin (Ed.).
154. Reiter G., Koller M., Thiermann H., Dorandeau F., Mikler J., Worek F.
155. Rice P. Use of Dermabrasion to treat sulphur mustard skin injuries. 11th Medical Chemical Defence Conference 2008, Germany, Munich.
156. Decontamination of Warfare Agents 2008, Wiley-VCH, Weinheim, Germany. A. Richardt, M.M. Blum (Eds.).
157. Rochu D., Chabrière E., Masson P. Human paraoxonase: a promising approach for pre-treatment and therapy of OP poisoning. Toxicology 2007, 233:47-59.
158. Satoh T., Hosokawa M. Structure, function and regulation of carboxylesterases. Chem. Biol. Interact. 2006, 162:195-211.
159. Satoh T., Taylor P., Borson W.F., Sanghani S.P., Hosokawa M., La Du B.N. Current progress on esterases: from molecular structure to function. Drug Metab. Dispos. 2002, 30:488-493.
160. Saxena A., Chunyuan L., Doctor B.P. Developing procedures for the large-scale purification of human serum butyrylcholinesterase. Protein Express. Purif. 2008, 61:191-196.
161. Schulz-Knappe P., Zucht H.D., Heine G., Jürgens M., Hess R., Schrader M. Peptidomics: the comprehensive analysis of peptides in complex biological mixtures. Comb. Chem. High Throughput Screen. 2001, 4:207-217.
162. Scremin O.U., Jenden D.J. Cholinergic control of cerebral flow in stroke, trauma, and aging. Life Sci. 1996, 58:2011-2018.
163. Seidell A. Solubilities of Organic Compounds 1941, Van Norstrand Co., New York. A. Seidell (Ed.).
164. Shahin S., Cullinane C., Gray P.J. Mitochondrial and nuclear DNA damage induced by sulphur mustard in keratinocytes. Chem. Biol. Interact. 2001, 138:231-245.
165. Shih M.L., McMonagle J.D., Dolzine T.W., Gresham V.C. Metabolite pharmacokinetics of soman, sarin and GF in rats and biological monitoring of exposure to toxic OP agents. J. Appl. Toxicol. 1994, 14:195-199.
166. Sidell F.R., Borak J. Chemical warfare agents: II. Nerve agents. Ann. Emerg. Med. 1992, 21:865-871.
167. Sidell F.R., GroffW.A. The reactivatibility of cholinesterase inhibited by VX and sarin in man. Toxicol. Appl. Pharmacol. 1974, 27:241-252.
168. Silveira, C.L., Elderfawi, A.T., Elderfawi, M.E. (1990). Putative M2 muscarinic receptors of rat heart have high affinity for OP anticholinesterases. Toxicol. Appl. Pharmacol.103: 474-81.
169. Sim, V.M., Duffy, F.H., Burchfiel, J.L., Gaon, M.D. (1971). Nerve agents and pesticides: value of computer analysis of electroencephalograms in the diagnosis of exposure to OPs and chlorinated hydrocarbons. Edgewood Arsenal, MD, DTIC AD785679.
170. Simonsen L., Fullerton A. Development of an in vitro skin permeation model simulating atopic dermatitis skin for the evaluation of dermatological products. Skin Pharmacol. Physiol. 2006, 20:230-236.
171. Smith J.R., Schlager J.J. Gas chromatographic separation of the stereoisomers of OP chemical warfare agents using cyclodextrin capillary columns. J. High Resolut. Chromatogr. 1996, 19:151-154.
172. Smith J.R., Capacio B.R., Korte W.D., Woolfitt A.R., Barr J.R. Analysis for plasma protein biomarkers following an accidental human exposure to sulfur mustard. J. Anal. Toxicol. 2008, 32:17-24.
173. Snider T.H., Wientjes M.G., Joiner R.L., Fisher G.L. Arsenic distribution in rabbits after Lewisite administration and treatment with British anti-Lewisite (BAL). Fundam. Appl. Toxicol. 1990, 14:262-272.
174. Solberg Y., Alkalay M., Belkin M. Ocular injury by mustard gas. Surv. Ophthalmol. 1997, 41:461-466.
175. Spruit H.E.T., Langenberg J.P., Trap H.C., Van der Wiel H.J., Helmich R.B., Van Helden H.P.M., Benschop H.P. Intravenous and inhalation toxicokinetics of sarin stereoisomers in atropinized guinea pigs. Toxicol. Appl. Pharmacol. 2000, 169:249-254.
176. Spruit H.E.T., Trap H.C., Langenberg J.P., Benschop H.P. Bioanalysis of the enantiomers of-sarin using automated thermal cold-trap injection combined with two-dimensional gas chromatography. J. Anal. Toxicol. 2001, 25:57-61.
177. Subcommittee on Chronic Reference Doses for Selected Chemical Warfare Agents, National Research Council (1999). Review of the U.S. Army's Health Risk Assessments for oral exposure to six chemical warfare agents. The National Academic Press, Washington, DC. http://www.nap.edu/catalog/9644.html.
178. Sweeney R.E., Langenberg J.P., Maxwell D.M. A physiologically based pharmacokinetic (PB/PK) model for multiple exposure routes of soman in multiple species. Arch. Toxicol. 2006, 80:719-731.
179. Thiermann H., Worek F., Szinicz L., Eyer P. Effects of oximes on muscle force and acetylcholinesterase activity in isolated mouse hemidiaphragm exposed to Paraoxon. Toxicology 2005, 214:190-197.
180. Thiermann H., Szinicz L., Eyer P., Felgenhauer N., Zilker T., Worek F. Lessons to be learnt from OP pesticide poisoning for the treatment of nerve agent poisoning. Toxicology 2007, 233:145-154.
181. ToxNet, Toxicology data network, Hazardous Substances Data Bank (HSDB), United States National Library of Medicine:data for tabun:; data for sarin:; data for soman:; data for VX:. http://toxnet.nlm.nih.gov/cgi-bin/sis/search/f%3F./temp/&%238764%3B8 KkwPp%3A1.
182. Tsuchihashi H., Katagi M., Nishikawa M., Tatsuno M. Identification of metabolites of nerve agent VX in serum collected from a victim. J. Anal. Toxicol. 1998, 22:383-388.
183. Tsugawa W., Nakamura H., Sode K., Ohuchi S. Improvement of enantioselectivity of chiral organophosphate insecticide hydrolysis by bacterial phosphotriesterase. Appl. Biochem. Biotechnol. 2000, 84-6:311-317.
184. Tsuge K., Seto Y. Detection of butyrylcholinesterase-nerve gas adducts by liquid chromatography-mass spectrometric analysis after in gel chymotryptic digestion. J. Chromatogr. B 2006, 838:21-30.
185. Vallet V., Cruz C., Licausi J., Bazire A., Lallement G., Boudry I. Percutaneous penetration and distribution of VX using in vitro pig or human excised skin validation of demeton-S-methyl as adequate simulant for VX skin permeation investigations. Toxicology 2008, 246:73-82.
186. Van der Schans M.J., Lander B.J., Van der Wiel H., Langenberg J.P., Benschop H.P. Toxicokinetics of nerve agent-VX in anesthetized and atropinized hairless guinea pigs and marmosets after intravenous and percutaneous administration. Toxicol. Appl. Pharmacol. 2003, 191:48-62.
187. Vilanova E., Sogorb M.A. The role of phosphotriesterases in the detoxication of OP compounds. Crit. Rev. Toxicol. 1999, 29:21-57.
188. Vilensky J.A., Redman K. British anti-Lewisite (dimercaprol): an amazing history. Ann. Emerg. Med. 2003, 41:378-383.
189. Vycudilik W. Detection of mustard gas bis(2-chloroethyl)-sulfide in urine. Forensic Sci. Int. 1985, 28:131-136.
190. Vycudilik W. Detection of bis(2-chlorethyl)-sulfide (Yperite) in urine by high resolution gas chromatography-mass spectrometry. Forensic Sci. Int. 1987, 35:67-71.
191. 14C-obidoxime. Toxicol. Environ. Chem. 1988, 18:1-10.
192. Weiss, M., Fresenau, M., Monius, T., Stutz, A., Billich, A. (2008). Binding of pimecrolimus and tacrolimus to skin and plasma proteins: implications for systemic exposure after topical application. Drug Metab. Dispos. June 4, 2008. (Epub ahead of print), DOI: 10.1124/dmd.108.021915.
193. Whalley C.E., Shih T.M. Effects of soman and sarin on high affinity choline uptake by rat brain synaptosomes. Brain Res. Bull. 1989, 22:853-858.
194. Williams N.H., Harrison J.M., Read R.W., Black R.M. Phosphylated tyrosine in albumin as a biomarker of exposure to OP nerve agents. Arch. Toxicol. 2007, 81:627-639.
195. Winkenwerder, W. (2002). Technical Report: Modeling and Risk Characterization of US Demolition Operations at the Khamisiyah Pit, Tab II to Appendix B -Summary of acute lethality data for sarin and cyclosarin. Force Health Protection and Readiness, Falls Church, VA, USA. http://www.gulflink.osd.mil/khamisiyah_tech/.
196. Wolthuis O.L., Berends F., Meeter E. Problems in the therapy of soman poisoning. Fundam. Appl. Toxicol. 1981, 1:183-192.
197. Worek F., Eyer P., Szinicz L. Inhibition, reactivation and aging kinetics of cyclohexylmethylphosphonofluoridate-inhibited human cholinesterases. Arch. Toxicol. 1998, 72:580-587.
198. Worek F., Koller M., Thiermann H., Szinicz L. Diagnostic aspects of organophosphate poisoning. Toxicology 2005, 214:182-189.
199. Worek F., Eyer P., Szincz L., Thiermann H. Simulation of cholinesterase status at different scenarios of nerve agent exposure. Toxicology 2007, 233:155-165.
200. Worek F., Aurbek N., Wetherell J., Pearce P., Mann T., Thiermann H. Inhibition, reactivation and aging kinetics of highly toxic OP compounds: pig versus minipig acetylcholinesterase. Toxicology 2008, 244:35-41.
201. Yeung D.T., Smith J.R., Sweeney R.E., Lenz D.E., Cerasoli D.M. Direct detection of stereospecific soman hydrolysis by wild-type human serum paraoxonase. FEBS J. 2007, 274:1183-1191.
202. Yeung D.T., Smith J.R., Sweeney R.E., Lenz D.E., Cerasoli D.M. A gas-chromatographic-mass spectrometric approach to examining stereoselective interaction of human plasma proteins with soman. J. Anal. Toxicol. 2008, 32:86-91.