Monitoring the hydrolysis of toxic organophosphonate nerve agents in aqueous buffer and in bicontinuous microemulsions by use of diisopropyl fluorophosphatase (DFPase) with 1H-31P HSQC NMR spectroscopy

Analytical and Bioanalytical Chemistry

Volumn 396, Issue 3, 2010, Pages 1213-1221

  Gäb, Jürgen ^a,b   Melzer, Marco ^a,c   Kehe, Kai ^d   Wellert, Stefan ^e   Hellweg, Thomas ^f   Blum, Marc Michael ^a  

^a Blum Scientific Services   (Germany)

^b PHILIPPS UNIVERSITY MARBURG   (Germany)

^c JOHANNES GUTENBERG UNIVERSITY   (Germany)

^d Bundeswehr Institute for Pharmacology and Toxicology   (Germany)

^e HAHN MEITNER INSTITUT   (Germany)

^f UNIVERSITY OF BAYREUTH   (Germany)

Author keywords

DFPase; Enzymes; Hydrolases; Nerve agents; NMR; Phosphotriesterases

Indexed keywords

AQUEOUS BUFFER; AQUEOUS SOLUTIONS; BICONTINUOUS MICROEMULSION; CYCLOSARIN; ENZYMATIC ACTIVITIES; FLUOROPHOSPHATE; FTIR; HSQC NMR; HYDROLASES; IN-SITU; KINETIC DATA; LIMITS OF DETECTION; LOLIGO VULGARIS; MANUAL HANDLING; NERVE AGENTS; NON-INVASIVE; ORGANOPHOSPHONATES; ORGANOPHOSPHORUS COMPOUNDS; PH-STAT; PHOSPHOTRIESTERASES; REACTIVE CHEMICALS; REAL-TIME QUANTIFICATION; TIME FRAME; WORK SAFETY;

CATALYSTS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HYDROLYSIS; ION SELECTIVE ELECTRODES; MICROEMULSIONS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORUS COMPOUNDS; TOXIC MATERIALS;

ENZYMES;

CHEMICAL WARFARE AGENT; CHOLINESTERASE INHIBITOR; CONVULSANT AGENT; CYCLOSARIN; DIISOPROPYL FLUOROPHOSPHATASE; DIISOPROPYL-FLUOROPHOSPHATASE; ORGANOPHOSPHORUS COMPOUND; PHOSPHOTRIESTERASE; SARIN; SOMAN;

ANIMAL; ARTICLE; ENZYMOLOGY; GENETIC PROCEDURES; HYDROLYSIS; METABOLISM; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SQUID; STATISTICAL PARAMETERS; VALIDATION STUDY;

ANIMALS; BIOSENSING TECHNIQUES; CHEMICAL WARFARE AGENTS; CHOLINESTERASE INHIBITORS; CONVULSANTS; HYDROLYSIS; LIMIT OF DETECTION; LOLIGO; MAGNETIC RESONANCE SPECTROSCOPY; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHORIC TRIESTER HYDROLASES; SARIN; SOMAN;

CEPHALOPODA; LOLIGO VULGARIS;

EID: 76749155337     PISSN: 16182642     EISSN: 16182650     Source Type: Journal    
DOI: 10.1007/s00216-009-3299-2     Document Type: Article

References (26)

1. Convention on the prohibition of the development, production, stockpiling and use of chemical weapons and on their destruction; Technical Secretariat of the Organisation for the Prohibition of Chemical Weapons: The Hague, 1997
2. A Vale 2005 What lessons can we learn from the Japanese sarin attacks? Przegl Lek 62 528 532
3. EI Scharff J Koepke G Fritzsch C Lücke H Rüterjans 2001 Crystal structure of diisopropylfluorophosphatase from Loligo vulgaris Structure 9 493 502 10.1016/S0969-2126(01)00610-4 1:CAS:528:DC%2BD3MXkvVekuro%3D (Pubitemid 32577101)
4. MM Blum F Löhr A Richardt H Rüterjans JCH Chen 2006 Binding of a designed substrate analogue to diisopropyl fluorophosphatase: implications for the phosphotriesterase mechanism J Am Chem Soc 128 12750 12757 10.1021/ja061887n 1:CAS:528:DC%2BD28XptlOls7o%3D (Pubitemid 44527751)
5. MM Blum M Mustyakimov H Rüterjans K Kehe BP Schönborn P Langan JCH Chen 2009 Rapid determination of hydrogen positions and protonation states of diisopropyl fluorophosphatase by joint neutron and X-ray diffraction refinement Proc Natl Acad Sci USA 106 713 718 10.1073/pnas.0807842106 1:CAS:528:DC%2BD1MXht12ju7o%3D
6. J Gäb M Melzer K Kehe A Richardt MM Blum 2009 Quantification of hydrolysis of toxic organophosphates and organophosphonates by diisopropyl fluorophosphatase from Loligo vulgaris by in situ Fourier transform infrared spectroscopy Anal Biochem 385 187 193 10.1016/j.ab.2008.11.012
7. J Hartleib H Rüterjans 2001 High-yield expression, purification, and characterization of the recombinant diisopropylfluorophosphatase from Loligo vulgaris Protein Expr Purif 21 210 219 10.1006/prep.2000.1360 1:CAS:528:DC%2BD3MXmsFCgsA%3D%3D (Pubitemid 32614516)
8. FCG Hoskin RJ Long 1972 Purification of a DFP- hydrolyzing enzyme from squid head ganglion Arch Biochem Biophys 150 548 555 10.1016/0003-9861(72)90073- 2 1:CAS:528:DyaE38XksVCksr0%3D
9. FCG Hoskin AH Roush 1982 Hydrolysis of nerve gas by squid-type diisopropyl phosphorofluoridate hydrolyzing enzyme on agarose resin Science 215 1255 1257 10.1126/science.7058344 1:CAS:528:DyaL38XhsFKrt70%3D
10. J Hartleib H Rüterjans 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 1546 312 324 1:CAS:528:DC%2BD3MXisF2rtrs%3D
11. G Amitai L Gaidukov R Adani S Yishay G Yacov M Kushnir S Teitlboim M Lindenbaum P Bel O Khersonsky DS Tawfik H Meshulam 2006 Enhanced stereoselective hydrolysis of toxic organophosphates by directly evolved variants of mammalian serum paraoxonase FEBS J 273 1906 1919 10.1111/j.1742-4658.2006.05198.x 1:CAS:528:DC%2BD28XkvVertrg%3D
12. L Briseno-Roa J Hill S Notman D Sellers AP Smith CM Timperley J Wetherell NH Williams GR Williams AR Fersht AD Griffiths 2006 Analogues with fluorescent leaving groups for screening and selection of enzymes that efficiently hydrolyze organophosphorus nerve agents J Med Chem 49 246 255 10.1021/jm050518j 1:CAS:528:DC%2BD2MXhtlSmtrvE (Pubitemid 43077337)
13. MM Blum CM Timperley GR Williams H Thiermann F Worek 2008 Inhibitory potency against human acetylcholinesterase and enzymatic hydrolysis of fluorogenic nerve agent mimics by human paraoxonase 1 and squid diisopropyl fluorophosphatase Biochemistry 47 5216 5224 10.1021/bi702222x 1:CAS:528:DC%2BD1cXksVShtL4%3D (Pubitemid 351620758)
14. S Wellert M Karg H Imhof A Steppin HJ Altmann M Dolle A Richardt B Tiersch J Koetz A Lapp T Hellweg 2008 Structure of biodiesel based bicontinuous microemulsions for environmentally compatible decontamination: A small angle neutron scattering and freeze fracture electron microscopy study J Colloid Interface Sci 325 250 258 10.1016/j.jcis.2008.05.062 1:CAS:528: DC%2BD1cXovFOqtrc%3D
15. Hellweg T, Wellert S, Mitchell SJ, Richardt A (2008) Microemulsions: a versatile carrier for decontamination agents. In: Richardt A, Blum MM (eds) Decontamination of warfare agents - Enzymatic methods for the removal of B/C weapons. Wiley-VCH, Weinheim
16. 1H} NMR spectroscopy Anal Chem 68 2313 2318 10.1021/ac960085f 1:CAS:528:DyaK28Xjtlygtr8%3D
17. 31P inverse NMR spectroscopy to the detection of trace amounts of organophosphorus compounds related to the chemical weapons convention Anal Chem 69 2694 2700 10.1021/ac9700639 1:CAS:528:DyaK2sXjvVChtbY%3D
18. 31P inverse NMR spectroscopy to the screening of solutions for the presence of organophosphorus compounds related to the chemical weapons convention Anal Chem 76 392 398 10.1021/ac0350099 1:CAS:528:DC%2BD3sXpsFyhtLY%3D (Pubitemid 38090777)
19. H Koskela ML Rapinoja ML Kuitunen P Vanninen 2007 Determination of trace amounts of chemical warfare agent degradation products in decontamination solutions with NMR spectroscopy Anal Chem 79 9098 9106 10.1021/ac0713196 1:CAS:528:DC%2BD2sXht1egs7fN (Pubitemid 350231721)
20. FM Raushel 2002 Bacterial detoxification of organophosphate nerve agents Curr Opin Microbiol 5 288 295 10.1016/S1369-5274(02)00314-4 1:CAS:528: DC%2BD38XktFynsLk%3D (Pubitemid 34614941)
21. TC Cheng JJ DeFrank VK Rastogi 1999 Alteromonas prolidase for organophosphorus G-agent decontamination Chem Biol Interact 119-120 455 462 10.1016/S0009-2797(99)00058-7 (Pubitemid 29278583)
22. DE Lenz D Yeung JR Smith RE Sweeney LA Lumley DM Cerasoli 2007 Stoichiometric and catalytic scavengers as protection against nerve agent toxicity: a mini review Toxicology 233 31 39 10.1016/j.tox.2006.11.066 1:CAS:528:DC%2BD2sXjslSqs7o%3D (Pubitemid 46505351)
23. Deutsche Forschungsgemeinschaft (1991) Rückstandsanalytik von Pflanzenschutzmitteln, 11:XI-A-1. VCH, Weinheim
24. H Frehse HP Their 1991 The limits of detection and of determination in residue analyses - their derivation according to the new DFP-approach GIT Fachz Lab 35 285 291 1:CAS:528:DyaK3MXlt12rtb8%3D
25. 1H NMR with external standards: use in preparation of calibration solutions for algal toxins and other natural products Anal Chem 77 3123 3131 10.1021/ac048385h 1:CAS:528:DC%2BD2MXis1Ojtrc%3D (Pubitemid 40695467)
26. Quinn LD (2000) Organophosphorus chemistry. Wiley-Interscience, New York, pp 169-172