Kinetic prerequisites of oximes as effective reactivators of organophosphate-inhibited acetylcholinesterase: a theoretical approach

References

• Namba T, Hiraki K. PAM (pyridine-2-aldoxime methiodide) therapy for alkylphosphate poisoning. JAMA 1958;166:1834–1839.
   PubMed Web of Science ®Google Scholar
• Eyer P. The role of oximes in the management of organophosphorus pesticide poisoning. Toxicol Rev 2003;22:165–190.
   PubMedGoogle Scholar
• Eddleston M, Eyer P, Worek F, Juszczak E, Alder N, Mohamed F, Senarathna L, Hittarage A, Azher S, Jeganathan K, Jayamanne S, von Meyer L, Dawson AH, Sheriff MH, Buckley NA. Pralidoxime in acute organophosphorus insecticide poisoning–a randomised controlled trial. PLoS Med 2009;6:e1000104.
   Google Scholar
• Eddleston M, Buckley NA, Eyer P, Dawson AH. Management of acute organophosphorus pesticide poisoning. Lancet 2008;371:597–607.
   PubMed Web of Science ®Google Scholar
• Jokanovic M. Medical treatment of acute poisoning with organophosphorus and carbamate pesticides. Toxicol Lett 2009;190:107–115.
   PubMed Web of Science ®Google Scholar
• Finkelstein Y, Kushnir A, Raikhlin-Eisenkraft B, Taitelman U. Antidotal therapy of severe acute organophosphate poisoning: a multihospital study. Neurotoxicol Teratol 1989;11:593–596.
   PubMed Web of Science ®Google Scholar
• Eyer P, Worek F. Oximes. In: Marrs TC, Maynard RL, Sidell FR, eds. Chemical Warfare Agents: Toxicology and Treatment. Chichester: John Wiley & Sons Ltd., 2007:305–29.
   Google Scholar
• Erdmann WD, von Clarmann. A new esterase reactivator for the treatment of alkylphosphate poisonings. Dtsch Med Wochenschr 1963;88:2201–2206.
   PubMed Web of Science ®Google Scholar
• Xue SZ, Ding XJ, Ding Y. Clinical observation and comparison of the effectiveness of several oxime cholinesterase reactivators. Scand J Work Environ Health 1985;11(Suppl 4):46–48.
   Google Scholar
• Kusic R, Jovanovic D, Randjelovic S, Joksovic D, Todorovic V, Boskovic B, Jokanovic M, Vojvodic V. HI-6 in man: efficacy of the oxime in poisoning by organophosphorus insecticides. Hum Exp Toxicol 1991;10:113–118.
   PubMed Web of Science ®Google Scholar
• Worek F, Eyer P, Aurbek N, Szinicz L, Thiermann H. Recent advances in evaluation of oxime efficacy in nerve agent poisoning by in vitro analysis. Toxicol Appl Pharmacol 2007;219:226–234.
   PubMed Web of Science ®Google Scholar
• Reiner E, Simeon-Rudolf V. Pyridinium, imidazolium and quinuclidinium compounds: toxicity and antidotal effects against the nerve agents Tabun and Soman. Arh Hig Rada Toksikol 2006;57:171–179.
   Google Scholar
• Hobbiger F. Reactivation of phosphorylated acetylcholinesterase. In: Koelle GB, ed. Cholinesterases and Anticholinesterase Agents. Berlin: Springer-Verlag, 1963:921–988.
   Google Scholar
• Hagedorn I, Gündel WH, Schoene K. Reaktivierung phosphorylierter acetylcholin-esterase mit oximen: beitrag zum studium des reaktionsablaufes. Drug Res 1969;19:603–606.
   Google Scholar
• Bismuth C, Inns RH, Marrs TC. Efficacy, toxicity and clinical use of oximes in anticholinesterase poisoning. In: Ballantyne B, Marrs TC, eds. Clinical and Experimental Toxicology of Organophosphates and Carbamates. Oxford: Butterworth & Heinemann, 1992:555–577.
   Google Scholar
• Worek F, Thiermann H, Szinicz L, Eyer P. Kinetic analysis of interactions between human acetylcholinesterase, structurally different organophosphorus compounds and oximes. Biochem Pharmacol 2004;68:2237–2248.
   PubMed Web of Science ®Google Scholar
• Worek F, Reiter G, Eyer P, Szinicz L. Reactivation kinetics of acetylcholinesterase from different species inhibited by highly toxic organophosphates. Arch Toxicol 2002;76:523–529.
   PubMed Web of Science ®Google Scholar
• Worek F, Thiermann H, Szinicz L. Reactivation and aging kinetics of human acetylcholinesterase inhibited by organophosphonylcholines. Arch Toxicol 2004;78:212–217.
   PubMed Web of Science ®Google Scholar
• Bartling A, Worek F, Szinicz L, Thiermann H. Enzyme-kinetic investigation of different sarin analogues reacting with human acetylcholinesterase and butyrylcholinesterase. Toxicology 2007;233:166–172.
   PubMed Web of Science ®Google Scholar
• Worek F, Aurbek N, Koller M, Becker C, Eyer P, Thiermann H. Kinetic analysis of reactivation and aging of human acetylcholinesterase inhibited by different phosphoramidates. Biochem Pharmacol 2007;73:1807–1817.
   PubMed Web of Science ®Google Scholar
• Aurbek N, Thiermann H, Szinicz L, Eyer P, Worek F. Analysis of inhibition, reactivation and aging kinetics of highly toxic organophosphorus compounds with human and pig acetylcholinesterase. Toxicology 2006;224:91–99.
   PubMed Web of Science ®Google Scholar
• Worek F, Aurbek N, Wetherell J, Pearce P, Mann T, Thiermann H. Inhibition, reactivation and aging kinetics of highly toxic organophosphorus compounds: pig versus minipig acetylcholinesterase. Toxicology 2008;244:35–41.
   PubMed Web of Science ®Google Scholar
• Worek F, Herkert NM, Koller M, Aurbek N, Thiermann H. Interaction of pentylsarin analogues with human acetylcholinesterase: a kinetic study. Toxicol Lett 2009;187:119–123.
   Google Scholar
• Eddleston M, Eyer P, Worek F, Mohamed F, Senarathna L, von Meyer L, Juszczak E, Hittarage A, Azhar S, Dissanayake W, Sheriff MH, Szinicz L, Dawson AH, Buckley NA. Differences between organophosphorus insecticides in human self-poisoning: a prospective cohort study. Lancet 2005;366:1452–1459.
   PubMed Web of Science ®Google Scholar
• Dawson RM. Review of oximes available for treatment of nerve agent poisoning. J Appl Toxicol 1994;14:317–331.
   PubMed Web of Science ®Google Scholar
• Thiermann H, Worek F, Eyer F, Eyer P, Felgenhauer K, Zilker T. Obidoxime in acute organophosphate poisoning: 2—PK/PD relationships. Clin Toxicol 2009;47:807–813.
   Web of Science ®Google Scholar
• Eyer F, Worek F, Eyer P, Felgenhauer K, Haberkorn M, Zilker T, Thiermann H. Obidoxime in acute organophosphate poisoning: 1—clinical effectiveness. Clin Toxicol 2009;47:798–806.
   Web of Science ®Google Scholar
• Peter JV, Moran JL, Graham P. Oxime therapy and outcomes in human organophosphate poisoning: an evaluation using meta-analytic techniques. Crit Care Med 2006;34:502–510.
   PubMed Web of Science ®Google Scholar
• Cherian MA, Roshini C, Peter JV, Cherian AM. Oximes in organophosphorus poisoning. Ind J Crit Care Med 2005;9:155–163.
   Google Scholar
• de Silva HJ, Wijewickrema R, Senanayake N. Does pralidoxime affect outcome of management in acute organophosphorus poisoning? Lancet 1992;339:1136–1138.
   PubMed Web of Science ®Google Scholar
• Pawar KS, Bhoite RR, Pillay CP, Chavan SC, Malshikare DS, Garad SG. Continuous pralidoxime infusion versus repeated bolus injection to treat organophosphorus pesticide poisoning: a randomised controlled trial. Lancet 2006;368:2136–2141.
   PubMed Web of Science ®Google Scholar
• Holmstedt B. Pharmacology of organophosphorus cholinesterase inhibitors. Pharmacol Rev 1959;11:567–688.
   PubMed Web of Science ®Google Scholar
• Eckert S, Eyer P, Herkert N, Bumm R, Weber G, Thiermann H, Worek F. Comparison of the oxime-induced reactivation of erythrocyte and muscle acetylcholinesterase following inhibition by sarin or paraoxon, using a perfusion model for the real-time determination of membrane-bound acetylcholinesterase activity. Biochem Pharmacol 2008;75:698–703.
   PubMed Web of Science ®Google Scholar
• Herkert NM, Eckert S, Eyer P, Bumm R, Weber G, Thiermann H, Worek F. Identical kinetics of human erythrocyte and muscle acetylcholinesterase with respect to carbamate pre-treatment, residual activity upon soman challenge and spontaneous reactivation after withdrawal of the inhibitors. Toxicology 2008;246:188–192.
   Google Scholar
• Thiermann H, Zilker T, Eyer F, Felgenhauer N, Eyer P, Worek F. Monitoring of neuromuscular transmission in organophosphate pesticide-poisoned patients. Toxicol Lett 2009;191:297–304.
   PubMed Web of Science ®Google Scholar
• Thiermann H, Szinicz L, Eyer F, Worek F, Eyer P, Felgenhauer N, Zilker T. Modern strategies in therapy of organophosphate poisoning. Toxicol Lett 1999;107:233–239.
   PubMed Web of Science ®Google Scholar
• Mast U. Reaktivierung der erythrozyten-acetylcholinesterase durch Oxime. Thesis, University Munich, 1997.
   Google Scholar
• Kovarik Z, Calic M, Sinko G, Bosak A. Structure-activity approach in the reactivation of tabun-phosphorylated human acetylcholinesterase with bis-pyridinium para-aldoximes. Arh Hig Rada Toksikol 2007;58:201–209.
   PubMedGoogle Scholar
• Skrinjaric-Spoljar M, Kralj M. Reactivating and protective effects of pyridinium compounds in human erythrocyte acetylcholinesterase inhibition by organophosphates in vitro. Arch Toxicol 1980;45:21–27.
   Google Scholar
• Skrinjaric-Spoljar M, Simeon V, Reiner E, Krauthacker B. Bis-pyridinium compounds: inhibition of human erythrocyte acetylcholinesterase and protection of the enzyme against phosphylation. Acta Pharmacol Jugoslav 1988;38:101–109.
   Google Scholar
• Calesnick B, Christensen, Richter M. Human toxicity of various oximes. 2-Pyridine aldoxime methyl chloride, its methane sulfonate salt, and 1,1′-trimethylenebis-(4-formylpyridinium chloride). Arch Environ Health 1967;15:599–608.
   PubMed Web of Science ®Google Scholar
• Marrs TC. Toxicology of oximes used in treatment of organophosphate poisoning. Adverse Drug React Toxicol Rev 1991;10:61–73.
   PubMedGoogle Scholar
• Pang YP, Kollmeyer TM, Hong F, Lee JC, Hammond PI, Haugabouk SP, Brimijoin S. Rational design of alkylene-linked bis-pyridiniumaldoximes as improved acetylcholinesterase reactivators. Chem Biol 2003;10:491–502.
   PubMed Web of Science ®Google Scholar
• Hammond PI, Kern C, Hong F, Kollmeyer TM, Pang YP, Brimijoin S. Cholinesterase reactivation in vivo with a novel bis-oxime optimized by computer-aided design. J Pharmacol Exp Ther 2003;307:190–196.
   PubMed Web of Science ®Google Scholar
• Eyer F, Meischner V, Kiderlen D, Thiermann H, Worek F, Haberkorn M, Felgenhauer N, Zilker T, Eyer P. Human parathion poisoning. A toxicokinetic analysis. Toxicol Rev 2003;22:143–163.
   PubMedGoogle Scholar
• Lotti M. Cholinesterase inhibition: complexities in interpretation. Clin Chem 1995;41:1814–1818.
   PubMed Web of Science ®Google Scholar