Effect of organophosphorus hydrolysing enzymes on obidoxime-induced reactivation of organophosphate-inhibited human acetylcholinesterase

Archives of Toxicology

Volumn 78, Issue 6, 2004, Pages 338-343

  Herkenhoff, S ^a   Szinicz, L ^a   Rastogi, V K ^b   Cheng, T C ^b   DeFrank, J J ^b   Worek, F ^a  

^a BUNDESWEHR INSTITUTE OF PHARMACOLOGY AND TOXICOLOGY   (Germany)

^b EDGEWOOD CHEMICAL BIOLOGICAL CENTER   (United States)

Author keywords

Acetylcholinesterase; Obidoxime; Organophosphate; Organophosphorus hydrolase; Phosphonyloxime

Indexed keywords

ACETYLCHOLINESTERASE; DIISOPROPYLFLUOROPHOSPHATASE; METHYLPHOSPHONOTHIOIC ACID S (2 DIISOPROPYLAMINOETHYL) O ETHYL ESTER; OBIDOXIME; ORGANOPHOSPHATE; ORGANOPHOSPHORUS ACID ANHYDROLASE; ORGANOPHOSPHORUS COMPOUND; ORGANOPHOSPHORUS HYDROLASE; PARAOXON; SARIN; SOMAN; TABUN; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; ENZYME INHIBITION; ENZYME REACTIVATION; HUMAN; HUMAN CELL; HYDROLYSIS; PRIORITY JOURNAL;

ANIMALS; ARYLDIALKYLPHOSPHATASE; BACTERIA; CHOLINESTERASE INHIBITORS; CHOLINESTERASE REACTIVATORS; DECAPODIFORMES; ENZYME ACTIVATION; ERYTHROCYTE MEMBRANE; HUMANS; OBIDOXIME CHLORIDE; PHOSPHORIC ACID ESTERS; PHOSPHORIC TRIESTER HYDROLASES; TIME FACTORS;

EID: 3142741790     PISSN: 03405761     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00204-004-0547-2     Document Type: Article

References (40)

1. Aldridge WN, Reiner E (1972) Enzyme inhibitors as substrates - interactions of esterases with esters of organophosphorus and carbamic acids. North-Holland Publishing, Amsterdam
2. Ashani Y, Leader H, Rothschild N, Dosoretz C (1998) Combined effect of organophosphorus hydrolase and oxime on the reactivation rate of diethylphosphoryl-acetylcholinesterase conjugates. Biochem Pharmacol 55:159-168
3. Ashani Y, Bhattacharjee AK, Leader H, Saxena A, Doctor BP (2003) Inhibition of cholinesterases with cationic phosphonyl oximes highlights distinctive properties of the charged pyridine groups of quaternary oxime reactivators. Biochem Pharmacol 66:191-202
4. Ballantyne B, Marrs TC (1992) Overview of the biological and clinical aspects of organophosphates and carbamates. In: Ballantyne B, Marrs TC (eds) Clinical and experimental toxicology of organophosphates and carbamates. Butterworth & Heinemann, Oxford, pp 3-14
5. Bismuth C, Inns RH, Marrs TC (1992) Efficacy, toxicity and clinical use of oximes in anticholinesterase poisoning. In: Ballantyne B Marrs TC (eds) Clinical and experimental toxicology of organophosphates and carbamates. Butterworth & Heinemann, Oxford, pp 555-577
6. de Jong LPA, Ceulen DI (1978) Anticholinesterase activity and rate of decomposition of some phosphylated oximes. Biochem Pharmacol 27:857-863
7. de Jong LPA, Wolring GZ (1978) Effect of 1-(AR)-alkyl-hydroxyiminomethyl- pyridinium salts on reactivation and aging of acetylcholinesterase inhibited ethyl dimethylphosphoramidocyanidate (tabun). Biochem Pharmacol 27:2229-2235
8. de Jong LPA, Wolring GZ (1984) Stereospecific reactivation by some Hagedorn-oximes of acetycholinesterases from various species including man inhibited by soman. Biochem Pharmacol 33:1119-1125
9. DeFrank JJ, Cheng TC (1991) Purification and properties of an organophosphorus acid anhydrase from a halophilic bacterial isolate. J Bacteriol 173:1938-1943
10. Dodge JT, Mitchell C, Hanahan DJ (1963) The preparation and chemical characteristics of hemoglobin-free ghosts of human erythrocytes. Arch Biochem Biophys 100:119-130
11. Ellman GL, Courtney KD, Anders V, Featherstone RM (1961) A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 7:88-95
12. Erdmann WD, Bosse I, Franke P (1965) Zur Resorption und Ausscheidung von Toxogonin nach intramuskulärer Injektion am Menschen. Dtsch Med Wochenschr 90:1436-1438
13. Eyer P (1996) Optimal oxime dosage regimen, a pharmacokinetic approach. In: Szinicz L, Eyer P, Klimmek R (eds) Role of oximes in the treatment of anticholinesterase agent poisoning. Spektrum Akademischer Verlag, Heidelberg, pp 33-51
14. Hackley BE, Owens OO (1959) Preparation of O-(isopropylmethylphosphono)- 4-formyl-1-methylpyridiniuin iodide oxime. J Org Chem 24:1120
15. Hackley BE, Steinberg GM, Lamb JC (1959) Formation of potent inhibitors of AChE by reaction of pyridinaldoximes with isopropyl methylphosphonofluoridate (GB). Arch Biochem Biophys 80:211-214
16. Hartleib J, Rüterjans H (2001) High-yield expression, purification, and characterization of the recombinant diisopropylfluorophosphatase from Loligo vulgaris. Protein Expr Purif 21:210-219
17. Harvey B, Sellers DJ, Watts P (1984) The reactivation by oximes of phosphonylated acetylcholinesterase: the possible erroneous interpretation of reactivating potency. Biochem Pharmacol 33:3499-3501
18. Harvey B, Scott RP, Sellers DJ, Watts P (1986) In vitro studies on the reactivation by oximes of phosphylated acetylcholinesterase-I. Biochem Pharmacol 35:737-744
19. Kiderlen D, Worek F, Klimmek R, Eyer P (2000) The phosphoryl oxime-destroying activity of human plasma. Arch Toxicol 74:27-32
20. Lamb JC, Steinberg GM, Hackley BE (1964) Isopropyl methylphosphonylated bisquaternary oximes, powerful inhibitors of cholinesterase. Biochim Biophys Acta 89:174-176
21. Leader H, Vincze A, Manisterski B, Rothschild N, Dosoretz C, Ashani Y (1999) Characterization of O,O-diethylphosphoryl oximes as inhibitors of cholinesterases and substrates of phosphotriesterases. Biochem Pharmacol 58:503-515
22. Lee EC (2003) Clinical manifestations of sarin nerve gas exposure. JAMA 290:659-662
23. MacIlwain C (1993) Study proves Iraq used nerve gas. Nature 363:3
24. Marrs TC (1993) Organophosphate poisoning. Pharmacol Ther 58:51-66
25. Mulbry WJ, Karns JS (1989) Parathion hydrolase specified by the Flavobacterium opd gene: relationship between the gene and the protein. J Bacteriol 171:6740-6746
26. Nagao M, Takatori T, Matsuda Y, Nakajima M, Iwase H, Iwadate K (1997) Definitive evidence for the acute sarin poisoning diagnosis in the Tokyo subway. Toxicol Appl Pharmacol 144:198-203
27. Nenner M (1974) Phosphonylierte Aldoxime Hemmwirkung auf Acetylcholinesterase und hydrolytischer Abbau. Biochem Pharmacol 23:1255-1262
28. Scaife JF (1959) Oxime reactivation studies of inhibited true and pseudo cholinesterase. Can J Biochem Physiol 37:1301-1311
29. Schoene K (1973) Phosphonyloxime aus Soman: Bildung und Reaktion mit Acetylcholinesterase in vitro. Biochem Pharmacol 22:2997-3003
30. Sidell FR (1992) Clinical considerations in nerve agent intoxication. In: Somani SM (ed) Chemical warfare agents. Academic Press, San Diego, pp 155-194
31. Sogorb MA, Vilanova E (2002) Enzymes involved in the detoxification of organophosphorus, carbamate and pyrethroid insecticides through hydrolysis. Toxicol Lett 128:215-228
32. Thiermann H, Szinicz L, Eyer F, Worek F, Eyer P, Felgenhauer N, Zilker T (1999) Modern strategies in therapy of organophosphate poisoning. Toxicol Lett 107:233-239
33. Volans AP (1996) Sarin: guidelines on the management of victims of a nerve gas attack. J Accid Emerg Med 13:202-206
34. Wilson IB, Ginsburg S (1955) A powerful reactivator of alkylphosphate-inhibited acetylcholinesterase. Biochim Biophys Acta 18:168-170
35. Worek F, Szinicz L (2000) Reaktivierung Nervenkampfstoffgehemmter humaner Erythrozyten-Acetylcholinesterase und Butyrylcholinesterase mit Oximen - Einfluß von Enzymkonzentration und Plasmabestandteilen. Interim Report Project 07/94
36. Worek F, Eyer P, Szinicz L (1998a) Inhibition, reactivation and aging kinetics of cyclohexylmethylphosphonofluoridate-inhibited human cholinesterases. Arch Toxicol 72:580-587
37. Worek F, Widmann R, Knopff O, Szinicz L (1998b) Reactivating potency of obidoxime, pralidoxime, HI 6 and HLö 7 in human erythrocyte acetylcholinesterase inhibited by highly toxic organophosphorus compounds. Arch Toxicol 72:237-243
38. Worek F, Diepold C, Eyer P (1999a) Dimethylphosphoryl-inhibited human cholinesterases: inhibition, reactivation, and aging kinetics. Arch Toxicol 73:7-14
39. Worek F, Mast U, Kiderlen D, Diepold C, Eyer P (1999b) Improved determination of acetylcholinesterase activity in human whole blood. Clin Chim Acta 288:73-90
40. Worek F, Eyer P, Kiderlen D, Thiermann H, Szinicz L (2000) Effect of human plasma on the reactivation of sarin-inhibited human erythrocyte acetylcholinesterase. Arch Toxicol 74:21-26