Biomarkers of organophosphorus nerve agent exposure: Comparison of phosphylated butyrylcholinesterase and phosphylated albumin after oxime therapy

Archives of Toxicology

Volumn 84, Issue 1, 2010, Pages 25-36

  Read, Robert W ^a   Riches, James R ^a   Stevens, Jacqueline A ^a   Stubbs, Sarah J ^a   Black, Robin M ^a  

^a DEFENCE SCIENCE AND TECHNOLOGY LABORATORY   (United Kingdom)

Author keywords

Biomarkers; Nerve agents; Oxime therapy; Phosphylated butyrylcholinesterase; Phosphylated tyrosine

Indexed keywords

ALBUMIN; BIOLOGICAL MARKER; CHOLINESTERASE; CYCLOSARIN; ORGANOPHOSPHORUS COMPOUND; OXIME; SARIN; SOMAN; TABUN; TYROSINE;

ARTICLE; CONTROLLED STUDY; DEALKYLATION; DEAMINATION; GUINEA PIG; HUMAN; IN VITRO STUDY; IN VIVO STUDY; MARMOSET; NONHUMAN; PRIORITY JOURNAL; PROTEIN PHOSPHORYLATION;

ANIMALS; BIOLOGICAL MARKERS; BUTYRYLCHOLINESTERASE; CALLITRICHINAE; CENTRAL NERVOUS SYSTEM AGENTS; CHOLINESTERASE INHIBITORS; CHOLINESTERASE REACTIVATORS; ENVIRONMENTAL EXPOSURE; HUMANS; INJECTIONS, INTRAMUSCULAR; LETHAL DOSE 50; ORGANOPHOSPHORUS COMPOUNDS; OXIMES; PHOSPHORYLATION; SERUM ALBUMIN; TIME FACTORS; TYROSINE;

ANIMALIA; CAVIA;

EID: 76749097989     PISSN: 03405761     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00204-009-0473-4     Document Type: Article

References (32)

1. R Barak A Ordentlich D Barak M Fischer HP Benschop LPA De Jong Y Segall B Velan A Shafferman 1997 Direct determination of the chemical composition of acetylcholinesterase phosphonylation products utilizing electrospray-ionization mass spectrometry FEBS Lett 407 42 50 10.1016/S0014-5793(97)00375-X (Pubitemid 27200982)
2. D Barak A Ordentlich D Kaplan R Barak D Mizrahi C Kronman Y Segall B Velan A Shafferman 1999 Evidence for P-N bond scission in phosphoramidate nerve agent adducts of human acetylcholinesterase Biochemistry 39 1156 1161 10.1021/bi992009n
3. JR Barr WJ Driskell LS Aston RA Martinez 2004 Quantitation of metabolites of the nerve agents sarin, soman, cyclosarin, VX, and Russian VX in human urine using isotope-dilution gas chromatography-tandem mass spectrometry J Anal Toxicol 28 372 378 1:CAS:528:DC%2BD2cXlsFKmsLY%3D 15239858
4. Black RM, Noort D (2005) Methods for the retrospective detection of exposure to toxic scheduled chemicals. Part A. Analysis of free metabolites. In: Mesilaakso M (ed) Chemical weapons convention chemicals analysis (sample collection, preparation and analytical methods). Wiley, Chichester, pp 403-431
5. RM Black RJ Clarke RW Read MTJ Reid 1994 Applications of gas chromatography-mass spectrometry and gas chromatography-tandem mass spectrometry to the analysis of chemical warfare samples, found to contain residues of the nerve agent sarin, sulphur mustard and their degradation products J Chromatogr A 662 301 321 10.1016/0021-9673(94)80518-0 1:CAS:528:DyaK2cXitFSisbs%3D 8143028 (Pubitemid 24075188)
6. RM Black JM Harrison RW Read 1999 The interaction of sarin and soman with plasma proteins: the identification of a novel phosphonylation site Arch Toxicol 73 123 126 10.1007/s002040050596 1:CAS:528:DyaK1MXitlyiur4%3D 10350193 (Pubitemid 29226171)
7. E Carletti H Li B Li F Ekström Y Nicolet M Loiodice E Gillon MT Froment O Lockridge LM Schopfer P Masson F Nachon 2008 Aging of cholinesterases phosphylated by tabun proceeds through O-dealkylation J Am Chem Soc 130 16011 16020 10.1021/ja804941z 1:CAS:528:DC%2BD1cXhtlWqtbbP 18975951
8. FL Ciner CE McCord RW Plunkett Jr CF Martin TR Croley 2007 Isotope dilution LC/MS/MS for the detection of nerve agent exposure in urine J Chromatogr B 846 42 50 10.1016/j.jchromb.2006.08.008 1:CAS:528: DC%2BD2sXhtVKgt7o%3D (Pubitemid 46149487)
9. CEAM Degenhardt K Pleisjier MJ van der Schans JP Langenberg K Preston MI Solano VL Maggio JR Barr 2004 Improvements of the fluoride reactivation method for the verification of nerve agent exposure J Anal Toxicol 28 364 371 1:CAS:528:DC%2BD2cXlsFKmsLk%3D 15239857
10. S-J Ding J Carr JE Carlson L Tong W Xue Y Li LM Schopfer B Li F Nachon O Asojo CM Thompson SH Hinrichs P Masson O Lockridge 2008 Five tyrosines and two serines in human albumin are labeled by the organophosphorus agent FP-biotin Chem Res Toxicol 21 1787 1794 10.1021/tx800144z 1:CAS:528:DC%2BD1cXpvFSntbY%3D 18707141
11. GL Ellman KD Courtney V Andres RM Featherstone 1961 A new rapid colorimetric determination of AChE activity Biochem Pharmacol 7 88 95 10.1016/0006-2952(61)90145-9 1:CAS:528:DyaF3MXht1Gns7o%3D 13726518
12. A Fidder AG Hulst D Noort R de Ruiter MJ van der Schans HP Benschop JP Langenberg 2002 Retrospective detection of exposure to organophosphorus anti-cholinesterases: mass spectrometric analysis of phosphylated human butyrylcholinesterase Chem Res Toxicol 15 582 590 10.1021/tx0101806 1:CAS:528:DC%2BD38XitFGhtrw%3D 11952345 (Pubitemid 34406420)
13. J Grunwald D Marcus Y Papier L Raveh Z Pittel Y Ashani 1997 Large-scale purification and long-term stability of human butyrylcholinesterase: a potential bioscavenger drug J Biochem Biophys Methods 34 123 135 10.1016/S0165-022X(97) 01208-6 1:CAS:528:DyaK2sXjs1ensrY%3D 9178088 (Pubitemid 27204971)
14. B Li LM Schopfer SH Hinrichs P Masson O Lockridge 2007 Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry assay for organophosphorus toxicants bound to human albumin at Tyr411 Anal Biochem 361 263 272 10.1016/j.ab.2006.11.018 1:CAS:528:DC%2BD2sXhtVKgurk%3D 17188226 (Pubitemid 46135390)
15. H Li LM Schopfer F Nachon MT Froment P Masson O Lockridge 2007 Aging pathways for organophosphate-inhibited human butyrylcholinesterase, including novel pathways for isomalathion, resolved by mass spectrometry Toxicol Sci 100 136 145 10.1093/toxsci/kfm215 1:CAS:528:DC%2BD2sXhtFKlsLvO 17698511 (Pubitemid 47617811)
16. B Li M Nachon MT Froment L Verdier JC Debouzy B Brasme E Gillon LM Schopfer O Lockridge P Masson 2008 Binding and hydrolysis of soman by human serum albumin Chem Res Toxicol 21 421 431 10.1021/tx700339m 1:CAS:528: DC%2BD1cXntFWr 18163544
17. DB Mawhinney EI Hamelin R Fraser SS Silva AJ Pavlopoulos RJ Kobelski 2007 The determination of organophosphonate nerve agent metabolites in human urine by hydrophilic interaction liquid chromatography tandem mass spectrometry J Chromatogr B 852 235 243 10.1016/j.jchromb.2007.01.023 1:CAS:528: DC%2BD2sXmtVGms7w%3D (Pubitemid 46830115)
18. M Nagao T Takatori Y Matsuda M Nakajima H Iwase K Iwadate 1997 Definitive evidence for the acute sarin poisoning diagnosis in the Tokyo subway Toxicol Appl Pharmacol 144 198 203 10.1006/taap.1997.8110 1:CAS:528:DyaK2sXivFKhur4%3D 9169085 (Pubitemid 27208353)
19. Noort D, Black RM (2005) Methods for the retrospective detection of exposure to toxic scheduled chemicals. Part B. Mass spectrometric and immunochemical analysis of covalent adducts to proteins and DNA. In: Mesilaakso M (ed) Chemical weapons convention chemicals analysis (sample collection, preparation and analytical methods). Wiley, Chichester, pp 433-451
20. D Noort AG Hulst DHJM Platenburg HP Benschop 1998 Quantitative analysis of O-isopropyl methylphosphonic acid in serum samples of Japanese citizens allegedly exposed to sarin: estimation of internal dosage Arch Toxicol 72 671 675 10.1007/s002040050559 1:CAS:528:DyaK1cXmvFCqtLo%3D 9851684 (Pubitemid 28523097)
21. D Noort AG Hulst LPA de Jong HP Benschop 1999 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 12 715 721 10.1021/tx9900369 1:CAS:528:DyaK1MXktl2jurk%3D 10458705 (Pubitemid 29398534)
22. D Noort A Fidder MJ van der Schans AG Hulst 2006 Verification of exposure to organophosphates: generic mass spectrometric method for detection of human butyrylcholinesterase adducts Anal Chem 78 6640 6644 10.1021/ac060954t 1:CAS:528:DC%2BD28Xot1aqsrk%3D 16970345 (Pubitemid 44413620)
23. ES Peeples LM Schopfer EG Duysen R Spaulding T Voelker CM Thompson O Lockridge 2005 Albumin, a new biomarker of organophosphorus toxicant exposure, identified by mass spectrometry Toxicol Sci 83 303 312 10.1093/toxsci/kfi023 1:CAS:528:DC%2BD2MXisVWmuw%3D%3D 15525694 (Pubitemid 40227900)
24. M Polhuijs JP Langenberg HP Benschop 1997 New method for retrospective detection of organophosphorus anticholinesterases: application to alleged sarin victims of Japanese terrorists Toxicol Appl Pharmacol 146 156 161 10.1006/taap.1997.8243 1:CAS:528:DyaK2sXmt1Wgsb0%3D 9299607 (Pubitemid 27406407)
25. J Riches I Morton RW Read RM Black 2005 The trace analysis of alkyl alkylphosphonic acids in urine using gas chromatography-ion trap negative ion tandem mass spectrometry J Chromatogr B 816 251 258 10.1016/j.jchromb.2004.11. 039 1:CAS:528:DC%2BD2MXmvFahsA%3D%3D
26. J Sun BC Lynn 2007 Development of a MALDI-TOF-MS method to identify and quantify butyrylcholinesterase inhibition resulting from exposure to organophosphate and carbamate pesticides J Am Soc Mass Spectrom 18 698 706 10.1016/j.jasms.2006.11.009 17223355 (Pubitemid 46441868)
27. LL Swaim RC Johnson Y Zhou C Sandlin JR Barr 2008 Quantification of organophosphorus nerve agent metabolites using a reduced-volume, high-throughput sample processing format and liquid chromatography-tandem mass spectrometry J Anal Toxicol 32 774 777 1:CAS:528:DC%2BD1cXhtl2gsrrL 19021934
28. H Tsuchihashi M Katagi M Nishikawa M Tatsuno 1998 Identification of metabolites of nerve agent VX in serum collected from a victim J Anal Toxicol 22 383 388 1:CAS:528:DyaK1cXlvFaru7s%3D 9737333
29. K Tsuge Y Seto 2006 Detection of human butyrylcholinesterase-nerve gas adducts by liquid chromatography-mass spectrometric analysis after in gel chymotryptic digestion J Chromatogr B 838 21 30 10.1016/j.jchromb.2006.02.054 1:CAS:528:DC%2BD28Xls1ejsLw%3D (Pubitemid 43832207)
30. United Nations (1984) Report of the specialists appointed by the Secretary-General to investigate allegations by the Islamic Republic of Iran concerning the use of chemical weapons. Report number S/16433
31. United Nations (1993) Convention on the prohibition of the development, production, stockpiling and use of chemical weapons and on their destruction
32. NH Williams JM Harrison RW Read RM Black 2007 Phosphylated tyrosine in albumin as a biomarker of exposure to organophosphorus nerve agents Arch Toxicol 81 627 639 10.1007/s00204-007-0191-8 1:CAS:528:DC%2BD2sXosFarsLc%3D 17345062 (Pubitemid 47228768)