A comparison of the reactivating and therapeutic efficacy of newly developed bispyridinium oximes (K250, K251) with commonly used oximes against tabun in rats and mice

References

• Kassa J. Review of oximes in the antidotal treatment of poisoning by organophosphorus nerve agents. J Toxicol Clin Toxicol 2002;40:803–816.
   PubMed Web of Science ®Google Scholar
• Marrs TC. Organophosphate poisoning. Pharmacol Ther 1993;58:51–66.
   PubMed Web of Science ®Google Scholar
• Cabal J, Bajgar J. Tabun – reappearance 50 years later (in Czech). Chem Listy 1999;93:27–31.
   Web of Science ®Google Scholar
• Ekström F, Akfur C, Tunemalm AK, Lundberg S. Structural changes of phenylalanine 338 and histidine 447 revealed by the crystal structures of tabun-inhibited murine acetylcholinesterase. Biochemistry 2006;45:74–81.
   PubMed Web of Science ®Google Scholar
• Jokanovic M, Maksimovic M, Kilibarda V, Jovanovic D, Savic D. Oxime-induced reactivation of acetylcholinesterase inhibited by phosphoramidates. Toxicol Lett 1996;85:35–39.
   PubMed Web of Science ®Google Scholar
• Bajgar J. Organophosphate/nerve agent poisoning: mechanism of action, diagnosis, prophylaxis and treatment. Adv Clin Chem 2004;38:151–216.
   PubMed Web of Science ®Google Scholar
• Koplovitz I, Stewart JR. A comparison of the efficacy of HI-6 and 2-PAM against soman, tabun, sarin and VX in the rabbit. Toxicol Lett 1994;70:169–179.
   Web of Science ®Google Scholar
• Puu G, Artursson E, Bucht G. Reactivation of nerve agent inhibited acetylcholinesterases by HI-6 and obidoxime. Biochem Pharmacol 1986;35:1505–1510.
   PubMed Web of Science ®Google Scholar
• Worek F, Widmann R, Knopff O, Szinicz L. Reactivating potency of obidoxime, pralidoxime, HI-6 and HLö-7 in human erythrocyte acetylcholinesterase inhibited by highly toxic organophosphorus compounds. Arch Toxicol 1998;72:237–243.
   PubMed Web of Science ®Google Scholar
• Musilek K, Holas O, Jun D, Dohnal V, Gunn-Moore F, Opletalova V, Dolezal M, Kuca K. Monooxime reactivators of acetylcholinesterase with (E)-but-2-ene linker – Preparation and reactivation of tabun and paraoxon-inhibited acetylcholinesterase. Bioorg Med Chem,2007;15: 6733–6741.
   PubMed Web of Science ®Google Scholar
• Tallarida R. Murray R. Manual of Pharmacological Calculation with Computer Programs. New York:Springer-Verlag;1987.
   Google Scholar
• Clement JG, Hansen AS, Boulet CA. Efficacy of HLö-7 and pyrimidoxime as antidotes of nerve agent poisoning in mice. Arch Toxicol 1992;66:216–219.
   PubMed Web of Science ®Google Scholar
• Ellman GL, Courtney DK, Andres VJr, Feartherstone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1961;7:88–93.
   PubMed Web of Science ®Google Scholar
• Kassa J, Cabal J. A comparison of the efficacy of a new asymmetric bispyridinium oxime BI-6 with currently available oximes and H oximes against soman by in vitro and in vivo methods. Toxicology 1999;132:111–118.
   PubMed Web of Science ®Google Scholar
• Kassa J, Cabal J. A comparison of the efficacy of a new asymmetric bispyridinium oxime BI-6 with presently used oximes and H oximes against sarin by in vitro and in vivo methods. Hum Exp Toxicol 1999;18:560–565.
   PubMed Web of Science ®Google Scholar
• Kassa J, Cabal J. A comparison of the efficacy of acetylcholinesterase reactivators against cyclohexylmethylphosphonofluoridate (GF agent) by in vitro and in vivo methods. Pharmacol Toxicol 1999;84:41–45.
   PubMedGoogle Scholar
• Kuca K, Kassa J. A comparison of the ability of a new bispyridinium oxime – 1-(4- hydroxyiminomethylpyridinium-4-(4-carbamoylpy ridinium)butane dibromide and currently used oximes to reactivate nerve agent-inhibited rat brain acetylcholinesterase by in vitro methods. J Enz Inhib Med Chem 2003;18:529–535.
   PubMed Web of Science ®Google Scholar
• Picha J, Kuca K, Kivala M, Kohout M, Cabal J, Liska F. New group of monoquaternary reactivators of the acetylcholinesterase inhibited by nerve agents. J Enz Inhib Med Chem 2005;20:233–237.
   PubMed Web of Science ®Google Scholar
• Musilek K, Holas O, Kuca K, Jun D, Dohnal V, Dolezal M. Synthesis of a novel non-symmetrical bispyridinium compounds bearing a xylene linker and evaluation of their reactivation activity using tabun and paraoxon-inhibited acetylcholinesterase. J Enz Inhib Med Chem 2007;22:425–432.
   PubMed Web of Science ®Google Scholar
• Musilek K, Holas O, Kuca K, Jun D, Dohnal V, Opletalova V, Dolezal M. Synthesis of monooxime-monocarbamoyl bispyridinium compounds bearing (E)-but-2-ene linker and evaluation of their reactivation activity against tabun- and paraoxon-inhibited acetylcholinesterase. J Enz Inhib Med Chem 2008;23:70–76.
   PubMed Web of Science ®Google Scholar
• Cabal J, Kuca K, Kassa J. Specification of the structure of oximes able to reactivate tabun-inhibited acetylcholinesterase. Pharmacol Toxicol 2004;95:81–86.
   Google Scholar
• Kuca K, Jun D, Musilek K. Structural requirements of acetylcholinesterase reactivators. Mini Rev Med Chem 2006;6:269–277.
   PubMed Web of Science ®Google Scholar
• Musilek K, Kuca K, Jun D, Dolezal M. Progress in synthesis of new acetylcholinesterase reactivators during the period 1990-2004. Curr Org Chem 2007; 11:229–238.
   Web of Science ®Google Scholar
• Carey FA, Sundberg RJ. In: The Structure and Mechanisms, 4th ed.; Plenum Publishers, New York, 2000, p. 13.
   Google Scholar
• Musilek K, Holas O, Kuca K, Jun D, Dohnal V, Opletalova V, Dolezal M. Novel series of bispyridinium compounds bearing a (Z)-but-2-ene linker – synthesis and evaluation of their reactivation activity against tabun and paraoxon-inhibited acetylcholinesterase. Bioorg Med Chem Lett 2007;17:3172–3176.
   PubMed Web of Science ®Google Scholar
• Bajgar J, Fusek J, Kuca K, Bartosova L, Jun D. Treatment of organophosphate intoxication using cholinesterase reactivators: facts and fiction. Mini-Rev Med Chem 2007;7:461–466.
   PubMed Web of Science ®Google Scholar
• Kassa J, Kuca K, Bartosova L, Kunesova G. 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 2007;11:267–283.
   Web of Science ®Google Scholar
• Jokanovic M, Maksimovic M. A comparison of trimedoxime, obidoxime, pralidoxime and HI-6 in the treatment of oral organophosphorus insecticide poisoning in the rat. Arch Toxicol 1995;70:119–123.
   PubMed Web of Science ®Google Scholar
• Petroianu GA, Nurulain SM, Nagelkerke N, Shafiullah M, Kassa J, Kuca K. Five oximes (K-27, K-48, obidoxime, HI-6 and trimedoxime) in comparison with pralidoxime: survival in rats exposed to methyl-paraoxon. J Appl Toxicol 2007;27: 453–457.
   PubMed Web of Science ®Google Scholar
• Worek F, Kirchner T, Bäker M, Szinicz L. Reactivation by various oximes of human erythrocyte acetylcholinesterase inhibited by different organophosphorus compounds. Arch Toxicol 1996;70:497–503.
   PubMed Web of Science ®Google Scholar
• Kassa J, Jun D, Kuca K. A comparison of reactivating efficacy of newly developed oximes (K074, K075) and currently available oximes (obidoxime, HI-6) in cyclosarin and tabun-poisoned rats. J Enz Inhib Med Chem. 2007; 22:297–300
   PubMed Web of Science ®Google Scholar
• Kassa J, Karasova J, Bajgar Kuca, K, Musilek KA comparison of the therapeutic and reactivating efficacy of newly developed bispyridinium compounds (K206, K269) with currently available oximes against tabun in rats and mice. J Enz Inhib Med Chem 2008; 23: 776–780
   PubMed Web of Science ®Google Scholar