Reactivation kinetics of a homologous series of bispyridinium bis-oximes with nerve agent-inhibited human acetylcholinesterase

Archives of Toxicology

Volumn 86, Issue 9, 2012, Pages 1379-1386

  Worek, Franz ^a   Von Der Wellen, Jens ^a   Musilek, Kamil ^b   Kuca, Kamil ^c   Thiermann, Horst ^a  

^a BUNDESWEHR INSTITUTE OF PHARMACOLOGY AND TOXICOLOGY   (Germany)

^b UNIVERSITY OF HRADEC KRALOVE   (Czech Republic)

^c UNIVERSITY OF DEFENCE   (Czech Republic)

Author keywords

Acetylcholinesterase; Kinetics; Nerve agent; Organophosphorus compound; Oximes; Reactivation

Indexed keywords

ACETYLCHOLINESTERASE; BIS(PYRIDINIUM OXIME) DERIVATIVE; CYCLOSARIN; OBIDOXIME; ORGANOPHOSPHATE; OXIME; SARIN; TABUN;

ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG MECHANISM; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME REACTIVATION; PRIORITY JOURNAL; SPECTROPHOTOMETRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ACETYLCHOLINESTERASE; ALKENES; CHOLINESTERASE INHIBITORS; CHOLINESTERASE REACTIVATORS; ERYTHROCYTE MEMBRANE; GPI-LINKED PROTEINS; HUMANS; KINETICS; MOLECULAR STRUCTURE; ORGANOPHOSPHATES; ORGANOPHOSPHORUS COMPOUNDS; OXIMES; PYRIDINIUM COMPOUNDS; SARIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84866065172     PISSN: 03405761     EISSN: 14320738     Source Type: Journal    
DOI: 10.1007/s00204-012-0842-2     Document Type: Article

References (25)

1. 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
2. Calic M, Bosak A, Kuca K, Kovarik Z (2008) Interactions of butane, but-2-ene or xylene-like linked bispyridinium para-aldoximes with native and tabun-inhibited human cholinesterases. Chem Biol Interact 175:305-308
3. De Jong LPA, Verhagen AAV, Langenberg JP, Hagedorn I, Löffler M (1989) The bispyridinium-dioxime HLö-7: a potent reactivator for acetylcholinesterase inhibited by the stereoisomers of tabun and soman. Biochem Pharmacol 38:633-640 (Pubitemid 19050103)
4. Ekström F, Pang YP, Boman M, Artursson E, Akfur C, Börjegren S (2006) Crystal structures of acetylcholinesterase in complex with HI-6, Ortho-7 and obidoxime: structural basis for differences in the ability to reactivate tabun conjugates. Biochem Pharmacol 72:597-607 (Pubitemid 44163303)
5. Eyer P, Worek F (2007) Oximes. In: Marrs TC, Maynard RL, Sidell FR (eds) Chemical warfare agents: toxicology and treatment. John Wiley & Sons Ltd., Chichester, pp 305-329
6. Eyer P, Worek F, Kiderlen D, Sinko G, Stuglin A, Simeon-Rudolf V, Reiner E (2003) Molar absorption coefficients for the reduced Ellman reagent: reassessment. Anal Biochem 312:224-227 (Pubitemid 36151135)
7. Gray AP (1984) Design and structure-activity relationships of antidotes to organophosphorus anticholinesterase agents. Drug Metab Rev 15:557-589 (Pubitemid 14011860)
8. Hobbiger F (1963) Reactivation of phosphorylated acetylcholinesterase. In: Koelle GB (ed) Cholinesterases and anticholinesterase agents. Springer, Berlin, pp 921-988
9. Kuca K, Sevelova-Bartosova L, Krejcova-Kunesova G (2004) In vitro reactivation of acetylcholinesterase inhibited by cyclosarin using bisquaternary pyridinium aldoximes K005, K033, K027 and K048. Acta Med 47:107-109
10. Kuca K, Cabal J, Jun D, Bajgar J, Hrabinova M (2006a) Potency of new structurally different oximes to reactivate cyclosarininhibited human brain acetylcholinesterases. J Enzym Inhib 21:663-666 (Pubitemid 44970954)
11. Kuca K, Cabal J, Jun D, Hrabinova M (2006b) In vitro evaluation of acetylcholinesterase reactivators as potential antidotes against tabun nerve agent poisonings. Drug Chem Toxicol 29:443-449 (Pubitemid 44384742)
12. Luo C, Chambers C, Pattabiraman N, Tong M, Tipparaju P, Saxena A (2010) Y124 at the peripheral anionic site is important for the reactivation of nerve agent-inhibited acetylcholinesterase by H oximes. Biochem Pharmacol 80:1427-1436
13. Musilek K, Kuca K, Jun D, Dohnal V, Dolezal M (2006) Synthesis of the novel series of bispyridinium compounds bearing (E)-but-2- ene linker and evaluation of their reactivation activity against chlorpyrifos-inhibited acetylcholinesterase. Bioorg Med Chem Lett 16:622-627 (Pubitemid 43019159)
14. Musilek K, Holas O, Jun D, Dohnal V, Gunn-Moore F, Opletalova V, Dolezal M, Kuca K (2007) Monooxime reactivators of acetylcholinesterase with (E)-but-2-ene linker-preparation and reactivation of tabun and paraoxon-inhibited acetylcholinesterase. Bioorg Med Chem 15:6733-6741 (Pubitemid 47385242)
15. Musilek K, Dolezal M, Gunn-Moore F, Kuca K (2011) Design, evaluation and structure-activity relationship studies of the AChE reactivators against organophosphorus pesticides. Med Res Rev 31:548-575
16. Reiner E, Simeon-Rudolf V (2006) Pyridinium, imidazolium and quinuclidinium compounds: toxicity and antidotal effects against the nerve agents tabun and soman. Arh Hig Rada Toksikol 57:171-179 (Pubitemid 43989261)
17. Schoene K (1980) Pyridinium salts as organophosphate antagonists. Monogr Neural Sci 7:85-98
18. Schoene K, Oldiges H (1973) Die Wirkungen von Pyridiniumsalzen gegenüber Tabun- und Sarinvergiftungen in vivo und in vitro. Arch Int Pharmacodyn Ther 204:110-123
19. Taylor P, Wong L, Radic Z, Tsigelny I, Brüggemann R, Hosea N, Berman HA (1999) Analysis of cholinesterase inactivation and reactivation by systematic structural modification and enantiomeric selectivity. Chem Biol Interact 119-120:3-15
20. Wong L, Radic Z, Brüggemann JM, Hosea N, Berman HA, Taylor P (2000) Mechanism of oxime reactivation of acetylcholinesterase analyzed by chirality andmutagenesis. Biochemistry 39:5750-5757 (Pubitemid 30307963)
21. Worek F, Mast U, Kiderlen D, Diepold C, Eyer P (1999) Improved determination of acetylcholinesterase activity in human whole blood. Clin Chim Acta 288:73-90 (Pubitemid 29472417)
22. Worek F, Reiter G, Eyer P, Szinicz L (2002) Reactivation kinetics of acetylcholinesterase from different species inhibited by highly toxic organophosphates. Arch Toxicol 76:523-529
23. Worek F, Thiermann H, Szinicz L, Eyer P (2004) Kinetic analysis of interactions between human acetylcholinesterase, structurally different organophosphorus compounds and oximes. Biochem Pharmacol 68:2237-2248 (Pubitemid 39446151)
24. Worek F, Aurbek N, Koller M, Becker C, Eyer P, Thiermann H (2007) Kinetic analysis of reactivation and aging of human acetylcholinesterase inhibited by different phosphoramidates. Biochem Pharmacol 73:1807-1817 (Pubitemid 46601412)
25. Worek F,Wille T, Aurbek N, Eyer P, Thiermann H (2010) Reactivation of organophosphate-inhibited human, cynomolgus monkey, swine and guinea pig acetylcholinesterase byMMB-4: a modified kinetic approach. Toxicol Appl Pharmacol 249:231-237