A comparison of the therapeutic and reactivating efficacy of newly developed bispyridinium compounds (K206, K269) with currently available oximes against tabun in rats and mice

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 23, Issue 6, 2008, Pages 776-780

  Kassa, Jiri ^a   Karasova, Jana ^a   Bajgar, Jiri ^a   Kuca, Kamil ^a   Musilek, Kamil ^a  

^a UNIVERSITY OF DEFENCE   (Czech Republic)

Author keywords

Acetylcholinesterase; Acetylthiocholine; HI 6; Inhibition; K206; K269; Obidoxime; Reactivation; Tabun; Trimedoxime

Indexed keywords

1 (3 CARBAMOYLPYRIDINIO) 1' (2 HYDROXYIMINOMETHYLPYRIDINIO)DIMETHYL ETHER; ACETYLCHOLINESTERASE; ATROPINE; BIS(PYRIDINIUM OXIME) DERIVATIVE; K 269; OBIDOXIME; TABUN; TIPINDOLE METHIODIDE; TRIMEDOXIME; UNCLASSIFIED DRUG;

ACUTE TOXICITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BLOOD; BRAIN; CONTROLLED STUDY; DIAPHRAGM; DRUG EFFICACY; DRUG POTENCY; DRUG STRUCTURE; ENZYME INHIBITION; ENZYME REACTIVATION; IN VIVO STUDY; INTOXICATION; LD 50; MALE; MONOTHERAPY; MOUSE; NEUROTOXICITY; NONHUMAN; PRIORITY JOURNAL; RAT; TISSUE;

ACETYLCHOLINESTERASE; ANIMALS; CHOLINESTERASE INHIBITORS; ENZYME ACTIVATION; LETHAL DOSE 50; MALE; MICE; MOLECULAR STRUCTURE; OXIMES; PYRIDINES; PYRIDINIUM COMPOUNDS; RATS;

MUS; RATTUS;

EID: 56449111425     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.1080/14756360701809902     Document Type: Article

References (28)

1. Kassa, J. (2002) Review of oximes in the antidotal treatment of poisoning by organophosphorus nerve agents. J Toxicol Clin Toxicol, 40, pp. 803-816.
2. Marrs, TC (1993) Organophosphate poisoning. Pharmacol Ther, 58, pp. 51-66.
3. Cabal, J. and Bajgar, J. (1999) Tabun - reappearance 50 years later (in Czech). Chem Listy, 93, pp. 27-31.
4. Ekstrom, F., Akfur, C., Tunemalm, AK and Lundberg, S. (2006) Structural changes of phenylalanine 338 and histidine 447 revealed by the crystal structures of tabun-inhibited murine acetylcholinesterase. Biochemistry, 45, pp. 74-81.
5. Jokanovic, M., Maksimovic, M., Kilibarda, V., Jovanovic, D. and Savic, D. (1996) Oxime-induced reactivation of acetylcholinesterase inhibited by phosphoramidates. Toxicol Lett, 85, pp. 35-39.
6. Bajgar, J. (2004) Organophosphate/nerve agent poisoning: Mechanism of action, diagnosis, prophylaxis and treatment. Adv Clin Chem, 38, pp. 151-216.
7. Koplovitz, I. and Stewart, JR (1994) A comparison of the efficacy of HI-6 and 2-PAM against soman, tabun, sarin and VX in the rabbit. Toxicol Lett, 70, pp. 169-179.
8. Kassa, J. (1995) Comparison of efficacy of two oximes (HI-6 and obidoxime) in soman poisoning in rats. Toxicology, 101, pp. 167-174.
9. Puu, G., Artursson, E. and Bucht, G. (1986) Reactivation of nerve agent inhibited acetylcholinesterases by HI-6 and obidoxime. Biochem Pharmacol, 35, pp. 1505-1510.
10. Worek, F., Widmann, R., Knopff, O. and Szinicz, L. (1998) Reactivating potency of obidoxime, pralidoxime, HI-6 and HLo-7 in human erythrocyte acetylcholinesterase inhibited by highly toxic organophosphorus compounds. Arch Toxicol, 72, pp. 237-243.
11. Musilek, K., Holas, O., Kuca, K., Jun, D., Dohnal, V., Opletalova, V. and Dolezal, M. (2007) 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
12. Musilek, K., Holas, O., Jun, D., Dohnal, V., Gunn-Moore, F., Opletalova, V., Dolezal, M. and 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, pp. 6733-6741.
13. Tallarida, R. and Murray, R. (1987) Manual of Pharmacological Calculation with Computer Programs, Springer-Verlag, New York
14. Clement, JG, Hansen, AS and Boulet, CA (1992) Efficacy of HLo-7 and pyrimidoxime as antidotes of nerve agent poisoning in mice. Arch Toxicol, 66, pp. 216-219.
15. Ellman, GL, Courtney, DK, Andres, VJr and Feartherstone, RM (1961) A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol, 7, pp. 88-93.
16. Kuca, K. and Kassa, J. (2003) 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 Enz Inhib Med Chem, 18, pp. 529-535.
17. Musilek, K., Holas, O., Kuca, K., Jun, D., Dohnal, V. and Dolezal, M. (2007) 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, 22, pp. 425-432.
18. Cabal, J., Kuca, K. and Kassa, J. (2004) Specification of the structure of oximes able to reactivate tabun-inhibited acetylcholinesterase. Pharmacol Toxicol, 95, pp. 81-86.
19. Kassa, J. and Cabal, J. (1999) 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, 132, pp. 111-118.
20. Kassa, J. and Cabal, J. (1999) 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, 18, pp. 560-565.
21. Kassa, J. and Cabal, J. (1999) A comparison of the efficacy of acetylcholinesterase reactivators against cyclohexylmethylphosphonofluoridate (GF agent) by in vitro and in vivo methods. Pharmacol Toxicol, 84, pp. 41-45.
22. Kuca, K., Jun, D. and Musilek, K. (2006) Structural requirements of acetylcholinesterase reactivators. Mini Rev Med Chem, 6, pp. 269-277.
23. Bajgar, J., Fusek, J., Kuca, K., Bartosova, L. and Jun, D. (2007) Treatment of organophosphate intoxication using cholinesterase reactivators: Facts and fiction. Mini-Rev Med Chem, 7, pp. 461-466.
24. Kassa, J. (2006) The influence of oxime and anticholinergic drug selection on the potency of antidotal treatment to counteract acute toxic effects of tabun in mice. Neurotox Res, 9, pp. 59-62.
25. Kassa, J., Kuca, K., Bartosova, L. and Kunesova, G. (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, pp. 267-283.
26. Jokanovic, M. and Maksimovic, M. (1995) A comparison of trimedoxime, obidoxime, pralidoxime and HI-6 in the treatment of oral organophosphorus insecticide poisoning in the rat. Arch Toxicol, 70, pp. 119-123.
27. Petroianu, GA, Nurulain, SM, Nagelkerke, N., Shafiullah, M., Kassa, J. and Kuca, K. (2007) 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, 27, pp. 453-457.
28. Worek, F., Kirchner, T., Baker, M. and Szinicz, L. (1996) Reactivation by various oximes of human erythrocyte acetylcholinesterase inhibited by different organophosphorus compounds. Arch Toxicol, 70, pp. 497-503.