617
Views
11
CrossRef citations to date
0
Altmetric
Original Article

A comparison of reactivating and therapeutic efficacy of the oxime K203 and its fluorinated analog (KR-22836) with currently available oximes (obidoxime, trimedoxime, HI-6) against tabun in rats and mice

, , , , &
Pages 480-484 | Received 11 Jun 2009, Accepted 12 Aug 2009, Published online: 16 Mar 2010

References

  • Marrs TC. Organophosphate poisoning. Pharmacol Ther 1993;58:51–66.
  • Lotti M. Organophosphorus compounds. In: Spencer PS, Schaumburg HH, eds. Experimental and Clinical Neurotoxicology. New York: Oxford University Press, 2000:898–925.
  • Kassa J. Review of oximes in the antidotal treatment of poisoning by organophosphorus nerve agents. J Toxicol Clin Toxicol 2002;40:803–16.
  • Bajgar J. Organophosphate/nerve agent poisoning: mechanism of action, diagnosis, prophylaxis, and treatment. Adv Clin Chem 2004;38:151–216.
  • Marrs TC, Rice P, Vale JA. The role of oximes in the treatment of nerve agent poisoning in civilian casualties. Toxicol Rev 2006;25:297–323.
  • Cabal J, Bajgar J. Tabun – reappearance 50 years later. Chem Listy 1999;93:27–31. [in Czech]
  • 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.
  • 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;70:169–79.
  • Kassa J. Comparison of efficacy of two oximes (HI-6 and obidoxime) in soman poisoning in rats. Toxicology 1995;101:167–74.
  • Puu G, Artursson E, Bucht G. Reactivation of nerve agent inhibited acetylcholinesterases by HI-6 and obidoxime. Biochem Pharmacol 1986;35:1505–10.
  • 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;72:237–43.
  • Kuca K, Musilek K, Paar M, Jun D, Stodulka P, Hrabinova M, et al. Targeted synthesis of 1-(4-hydroxyiminomethylpyridinium)-3-pyridiniumpropane dibromide – a new nerve agent reactivator. Molecules 2007;12:1964–72.
  • Musilek K, Holas O, Kuca K, Jun D, Dohnal V, Opletalova V, et al. 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 Enzyme Inhib Med Chem 2007;23:70–6.
  • Kassa J, Karasova J, Musilek K, Kuca K. An evaluation of therapeutic and reactivating effects of newly developed oximes (K156, K203) and commonly used oximes (obidoxime, trimedoxime, HI-6) in tabun-poisoned rats and mice. Toxicology 2008;243:311–16.
  • Jeong HCH, Kang NS, Park N-J, Yum EK, Jung Y-S. Reactivating potency of fluorinated pyridinium oximes for acetylcholinesterases inhibited by paraoxon organophosphorus agent. Bioorg Med Chem Lett 2009;19:1214–17.
  • Jeong HCH, Park N-J, Chae CHH, Musilek K, Kassa J, Kuca K, Jung Y-S. Fluorinated pyridinium oximes as potential reactivators for acetycholinesterases inhibited by paraoxon organophosphorus agent. Bioorg Med Chem 2009;17:6213–17.
  • Tallarida R, Murray R. Manual of Pharmacological Calculation with Computer Programs. New York: Springer-Verlag, 1987.
  • Clement JG, Hansen AS, Boulet CA. Efficacy of HLö-7 and pyrimidoxime as antidotes of nerve agent poisoning in mice. Arch Toxicol 1992;66:216–19.
  • Ellman GL, Courtney DK, Andres V Jr, Feartherstone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1961;7:88–93.
  • Wildman SA, Crippen GM. Prediction of physicochemical parameters by atomic contribution. J Chem Inf Comp Sci 1999;39:868–73.
  • Mueller K, Faeh C, Diederich F. Fluorine in pharmaceuticals: looking beyond intuition. Science 2007;317:1881–6.
  • Kirk KL. Selective fluorination in drug design and development. An overview of biochemical rationales. Curr Top Med Chem 2006;6:1447–56.
  • 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;132:111–18.
  • 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;18:560–5.
  • 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;84:41–5.
  • Kuca K, Kassa J. A comparison of the ability of a new bispyridinium oxime – 1-(4- hydroxyiminomethylpyridinium-4-(4-carbamoylpyridinium)butane dibromide and currently used oximes to reactivate nerve agent-inhibited rat brain acetylcholinesterase by in vitro methods. J Enzyme Inhib Med Chem 2003;18:529–35.
  • Musilek K, Holas O, Kuca K, Jun D, Dohnal V, Dolezal M. Synthesis of novel non-symmetrical bispyridinium compounds bearing a xylene linker and evaluation of their reactivation activity using tabun and paraoxon-inhibited acetylcholinesterase. J Enzyme Inhib Med Chem 2007;22:425–32.
  • 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 Enzyme Inhib Med Chem 2005;20:233–7.
  • Kuca K, Jun D, Musilek K. Structural requirements of acetylcholinesterase reactivators. Mini Rev Med Chem 2006;6:109–20.
  • Cabal J, Kuca K, Kassa J. Specification of the structure of oximes able to reactivate tabun-inhibited acetylcholinesterase. Pharmacol Toxicol 2004;95:81–6.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.