The evaluation of the reactivating and therapeutic efficacy of two novel oximes (K361 and K378) in comparison with the oxime K203 and trimedoxime in tabun-poisoned rats and mice

References

• Antonijevic B, Stojiljkovic P. (2007). Unequal efficacy of pyridinium oximes in acute organophosphate poisoning. Clin Med Res 5:71–82
   PubMedGoogle Scholar
• Bajgar J. (2004). Organophosphate/nerve agent poisoning: mechanism of action, diagnosis, prophylaxis and treatment. Adv Clin Chem 38:151–216
   PubMed Web of Science ®Google Scholar
• Cabal J, Bajgar J. (1999). Tabun – reappearance 50 years later (in Czech). Chem Listy 93:27–31
   Web of Science ®Google Scholar
• Cabal J, Kuca K, Kassa J. (2004). Specification of the structure of oximes able to reactivate tabun-inhibited acetylcholinesterase. Pharmacol Toxicol 95:81–6
   Google Scholar
• Clement JG, Hansen AS, Boulet CA. (1999). Efficacy of HLö-7 and pyrimidoxime as antidotes of nerve agent poisoning in mice. Arch Toxicol 66:216–19
   Web of Science ®Google Scholar
• Dawson RM. (1994). Review of oximes available for treatment of nerve agent poisoning. J Appl Toxicol 14:317–31
   PubMed Web of Science ®Google Scholar
• Eddleston M, Szinicz L, Eyer P, et al. (2002). Oximes in acute organophosphorus pesticide poisoning: a systematic review of clinical trials. Q J Med 95:275–83
   Google Scholar
• Ekström F, Akfur C, Tunemalm AK, et al. (2006). Structural changes of phenylalanine 338 and histidine 447 revealed by the crystal structures of tabun-inhibited murine acetylcholinesterase. Biochemistry 45:74–81
   PubMed Web of Science ®Google Scholar
• Ellman GL, Courtney DK, Andres V, Jr et al. (1961). A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 7:88–93
   PubMed Web of Science ®Google Scholar
• Eyer P. (2003). The role of oximes in the management of organophosphorus pesticide poisoning. Toxicol Rev 22:165–90
   PubMedGoogle Scholar
• Johnson MK, Jacobsen D, Meredith TJ, et al. (2000). Evaluation of antidotes for poisoning by organophosphorus pesticides. Emer Med 12:22–37
   Google Scholar
• Jokanovic M. (2012). Structure-activity relationship and efficacy of pyridinium oximes in the treatment of poisoning with organophosphorus compounds: a review of recent data. Curr Topic Med Chem 12:1775–89
   PubMed Web of Science ®Google Scholar
• Jokanovic M, Prostran M. (2009). Pyridinium oximes as cholinesterase reactivators. Structure-activity relationship and efficacy in the treatment of poisoning with organophosphorus compounds. Curr Med Chem 16:2177–88
   PubMed Web of Science ®Google Scholar
• de Jong LPA, Benschop HP, van den Berg GR, et al. (1981). Reactivation of tabun-inhibited acetylcholinesterase by 1-(hetero)arylmethyl-pyridinium oximes. Eur J Med Chem 16:257–62
   Web of Science ®Google Scholar
• Jun D, Kuca K, Stodulka P, et al. (2007). HPLC analysis of HI-6 dichloride and dimethanesulfonate – antidotes against nerve agents and organophosphorus pesticides. Anal Lett 40:2783–7
   Web of Science ®Google Scholar
• Kassa J, Kuca K, Bartosova L, et al. (2007). The development of new structural analogues of oximes for the antidotal treatment of poisoning by nerve agents and the comparison of their reactivating and therapeutic efficacy with currently available oximes. Curr Org Chem 11:267–83
   Web of Science ®Google Scholar
• Kassa J, Karasova J, Musilek K, et al. (2008). An evaluation of therapeutic and reactivating effects of newly developed oximes (K156, K203) with commonly used oximes (obidoxime, trimedoxime, HI-6) in tabun-poisoned rats and mice. Toxicology 243:311–16
   PubMed Web of Science ®Google Scholar
• Kloog Y, Galron R, Sokolovsky M. (1986). Bisquaternary pyridinium oximes as presynaptic agonists and postsynaptic antagonists of muscarinic receptors. J Neurochem 46:767–72
   PubMed Web of Science ®Google Scholar
• Kuca K, Cabal J, Kassa J. (2004). A comparison of the efficacy of a bispyridinium oxime – 1,4-bis-(2-hydroxyiminomethylpyridinium) butane dibromide and currently used oximes to reactivate sarin, tabun or cyclosarin-inhibited acetylcholinesterase by in vitro methods. Pharmazie 59:795–8
   PubMed Web of Science ®Google Scholar
• Kuca K, Jun D, Musilek K. (2006). Structural requirements of acetylcholinesterase reactivators. Mini Rev Med Chem 6:269–77
   PubMed Web of Science ®Google Scholar
• Lorke DE, Kalasz H, Petroianu GA, et al. (2008). Entry of oximes into the brain. A review. Curr Med Chem 15:743–53
   PubMed Web of Science ®Google Scholar
• Lotti M. (2000). Organophosphorus compounds. In Spencer PS, Schaumburg HH, eds. Experimental and clinical neurotoxicology. New York: Oxford University Press, 898–925
   Google Scholar
• Lundy PM, Hamilton MG, Sawyer TW, et al. (2011). Comparative protective effects of HI-6 and MMB-4 against organophosphorous nerve agent poisoning. Toxicology 285:90–6
   PubMed Web of Science ®Google Scholar
• Marrs TC, Rice P, Vale JA. (2006). The role of oximes in the treatment of nerve agent poisoning in civilian casualties. Toxicol Rev 25:297–323
   PubMedGoogle Scholar
• Musilek K, Holas O, Kuca K, et al. (2007a). Synthesis of the novel series of non-symmetrical bispyridinium compounds bearing xylene linker and evaluation of their reactivation activity against tabun and paraoxon-inhibited acetylcholinesterase. J Enzym Inhib Med Chem 22:425–32
   PubMed Web of Science ®Google Scholar
• Musilek K, Kuca K, Jun D, et al. (2007b). Progress in synthesis of new acetylcholinesterase reactivators during the period 1990 – 2004. Curr Org Chem 11:229–38
   Web of Science ®Google Scholar
• Musilek K, Kucera J, Jun D, et al. (2008). Monoquaternary pyridinium salts with modified side chain – synthesis and evaluation on model of tabun- and paraoxon-inhibited acetylcholinestrase. Bioorg Med Chem 16:8218–23
   PubMed Web of Science ®Google Scholar
• Musilek K, Dolezal M, Gunn-Moore F, et al. (2011). Design, evaluation and structure-activity relationship studies of the AChE reactivators against organophosphorus pesticides. Med Res Rev 31:548–75
   PubMed Web of Science ®Google Scholar
• Nurulain SM. (2011). Efficacious oxime for organophosphorus poisoning: a minireview. Trop J Pharm Res 10:341–9
   Web of Science ®Google Scholar
• Peter JV, Cherian AV. (2000). Organic insecticides. Anaesth Intensive Care 28:11–21
   PubMed Web of Science ®Google Scholar
• Peter JV, Moran JL, Graham P. (2006). Oxime therapy and outcomes in human organophosphate poisoning: an evaluation using meta-analytic techniques. Crit Care Med 34:502–10
   PubMed Web of Science ®Google Scholar
• Sakurada K, Matsubara K, Shimizu K, et al. (2003). Pralidoxime iodide (2-PAM) penetrates across the blood-brain barrier. Neurochem Res 28:1401–7
   PubMed Web of Science ®Google Scholar
• Tallarida R, Murray R. (1987). Manual of pharmacological calculation with computer programs. New York: Springer-Verlag
   Google Scholar
• Van Helden HPM, Busker RW, Melchers BPC, et al. (1996). Pharmacological effects of oximes: how relevant are they? Arch Toxicol 70:779–86
   PubMed Web of Science ®Google Scholar
• Worek F, Widmann R, Knopff O, et al. (1998). Reactivating potency of obidoxime, pralidoxime, HI-6 and HLö-7 in human erythrocyte acetylcholinesterase inhibited by highly toxic organophosphorus compounds. Arch Toxicol 72:237–43
   PubMed Web of Science ®Google Scholar