Detoxification of nerve agents by a substituted β-cyclodextrin: Application of a modified biological assay

Toxicology

Volumn 265, Issue 3, 2009, Pages 96-100

  Wille, T ^a   Tenberken, O ^a   Reiter, G ^a   Muller S ^a   Le Provost, R ^b,c   Lafont, O ^b   Estour, F ^b,c   Thiermann, H ^a   Worek, F ^a  

^a BUNDESWEHR INSTITUTE OF PHARMACOLOGY AND TOXICOLOGY   (Germany)

^b Normandie Université   (France)

^c UNIVERSITÉ DE ROUEN   (France)

Author keywords

Cyclodextrin; Acetylcholinesterase; Biological assay; Nerve agents; Small molecule scavenger

Indexed keywords

2 O (3 CARBOXYL 4 IODOSOBENZYL) BETA CYCLODEXTRIN; ACETYLCHOLINESTERASE; BETA CYCLODEXTRIN; BETA CYCLODEXTRIN DERIVATIVE; CHEMICAL WARFARE AGENT; CYCLOSARIN; METHYLPHOSPHONOTHIOIC ACID S (2 DIISOPROPYLAMINOETHYL) O ETHYL ESTER; SARIN; TABUN; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; BIOASSAY; CHEMICAL ANALYSIS; CHEMICAL REACTION; CONTROLLED STUDY; DETOXIFICATION; ENZYME INHIBITION; ERYTHROCYTE; HUMAN; HUMAN CELL; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS;

ACETYLCHOLINESTERASE; BETA-CYCLODEXTRINS; BIOLOGICAL ASSAY; BUFFERS; CHEMICAL WARFARE AGENTS; CHOLINESTERASE INHIBITORS; ERYTHROCYTE MEMBRANE; HUMANS; HYDROGEN-ION CONCENTRATION; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS; ORGANOTHIOPHOSPHORUS COMPOUNDS; PHOSPHORIC ACID ESTERS; REFERENCE STANDARDS; REPRODUCIBILITY OF RESULTS; SARIN; TIME FACTORS;

EID: 71749092296     PISSN: 0300483X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tox.2009.09.018     Document Type: Article

References (24)

1. Black R.M., and Harrison J.M. The chemistry of organophosphorus chemical warfare agents. In: Hartley F.R. (Ed). The Chemistry of Organophosphorus Compounds (1996), John Wiley & Sons, Chichester 781-840
2. Breslow R., and Dong S.D. Biomimetic reactions catalyzed by cyclodextrins and their derivatives. Chem. Rev. 98 (1998) 1997-2012
3. Brewster M.E., and Loftsson T. Cyclodextrins as pharmaceutical solubilizers. Adv. Drug Deliv. Rev. 59 (2007) 645-666
4. Desire B., and Saint-Andre S. Interaction of soman with α-cyclodextrin. Fundam. Appl. Toxicol. 7 (1986) 646-657
5. Desire B., and Saint-Andre S. Inactivation of sarin and soman by cyclodextrins in vitro. Experientia 43 (1987) 395-397
6. Dodge J.T., Mitchell C., and Hanahan D.J. The preparation and chemical characteristics of hemoglobin-free ghosts of human erythrocytes. Arch. Biochem. Biophys. 100 (1963) 119-130
7. Eyer P., Worek F., Kiderlen D., Sinko G., Stuglin A., Simeon-Rudolf V., and Reiner E. Molar absorption coefficients for the reduced Ellman reagent: reassessment. Anal. Biochem. 312 (2003) 224-227
8. Grob D. The manifestations and treatment of poisoning due to nerve gas and other organic phosphate anticholinesterase compounds. Arch. Intern. Med. 98 (1956) 221-239
9. Hoskin F.C., Steeves D.M., and Walker J.E. Substituted cyclodextrin as a model for a squid enzyme that hydrolyzes the nerve gas soman. Biol. Bull. 197 (1999) 284-285
10. LeJeune K.E., Dravis B.C., Yang F., Hetro A.D., Doctor B.P., and Russell A.J. Fighting nerve agent chemical weapons with enzyme technology. Ann. N. Y. Acad. Sci. 864 (1998) 153-170
11. MacIlwain C. Study proves Iraq used nerve gas. Nature 363 (1993) 3
12. Marrs T.C. Organophosphate poisoning. Pharmacol. Ther. 58 (1993) 51-66
13. Masurier N., Estour F., Froment M.T., Lefevre B., Debouzy J.C., Brasme B., Masson P., and Lafont O. Synthesis of 2-substituted β-cyclodextrin derivatives with a hydrolytic activity against the organophosphorylester paraoxon. Eur. J. Med. Chem. 40 (2005) 615-623
14. Masurier N., Estour F., Lefevre B., Brasme B., Masson P., and Lafont O. Improved access to 2-O-monobenzyl ethers of β-cyclodextrin as precursors of catalysts for organophosphoryl esters hydrolysis. Carbohydr. Res. 341 (2006) 935-940
15. Nagao M., Takatori T., Matsuda Y., Nakajima M., Iwase H., and Iwadate K. Definitive evidence for the acute sarin poisoning diagnosis in the Tokyo subway. Toxicol. Appl. Pharmacol. 144 (1997) 198-203
16. Reiter G., Mikler J., Hill I., Weatherby K., Thiermann H., and Worek F. Chromatographic resolution, characterisation and quantification of VX enantiomers in hemolysed swine blood samples. J. Chromatogr. B 873 (2008) 86-94
17. Tenberken, O., Worek, F., Thiermann, H., Reiter, G., in press. Development and validation of a sensitive gas chromatography-ammonia chemical ionization mass spectrometry method for the determination of tabun enantiomers in hemolyzed blood and plasma of different species. J. Chromatogr. B. doi:10.1016/j.jchromb.2009.09.002
18. Vale J.A., Rice P., and Marrs T.C. Managing civilian casualties affected by nerve agents. In: Marrs T.C., Maynard R.L., and Sidell F.R. (Eds). Chemical Warfare Agents: Toxicology and Treatment (2007), John Wiley, London 249-260
19. van der Schans M.J., Lander B.J., van der W.H., Langenberg J.P., and Benschop H.P. Toxicokinetics of the nerve agent (±)-VX in anesthetized and atropinized hairless guinea pigs and marmosets after intravenous and percutaneous administration. Toxicol. Appl. Pharmacol. 191 (2003) 48-62
20. Van Hooidonk C., and Breebaart-Hansen J.C. Stereospecific reaction of isopropyl methyl-phosphonofluoridate (sarin) with α-cyclodextrin. Recueil 89 (1970) 289-299
21. Worek F., Mast U., Kiderlen D., Diepold C., and Eyer P. Improved determination of acetylcholinesterase activity in human whole blood. Clin. Chim. Acta 288 (1999) 73-90
22. Worek F., Reiter G., Eyer P., and Szinicz L. Reactivation kinetics of acetylcholinesterase from different species inhibited by highly toxic organophosphates. Arch. Toxicol. 76 (2002) 523-529
23. Worek F., Koller M., Thiermann H., and Szinicz L. Diagnostic aspects of organophosphate poisoning. Toxicology 214 (2005) 182-189
24. Zilker T. Medical management of incidents with chemical warfare agents. Toxicology 214 (2005) 221-231