Evaluation of oxime K203 as antidote in tabun poisoning

Arhiv za Higijenu Rada i Toksikologiju

Volumn 60, Issue 1, 2009, Pages 19-26

  Kovarik, Zrinka ^a   Vrdoljak, Ana Lucić ^a   Berend, Suzana ^a   Katalinić, Maja ^a   Kuč, Kamil ^b   Musilek, Kamil ^b   Radić, Bozǎica ^a  

^a INSTITUTE FOR MEDICAL RESEARCH AND OCCUPATIONAL HEALTH   (Croatia)

^b UNIVERSITY OF DEFENCE   (Czech Republic)

Author keywords

Acetylcholinesterase; Bioscavenger; Butyrylcholinesterase; K048; Nerve agents; Pyridinium oxime; TMB 4

Indexed keywords

1 (4 CARBAMOYLPYRIDINIUM) 4 (4 HYDROXYIMINOMETHYL PYRIDINIUM)BUT 2 ENE DIBROMIDE; ACETYLCHOLINESTERASE; ANTIDOTE; CHOLINESTERASE; K 048; K 203; OXIME DERIVATIVE; TABUN; TRIMEDOXIME; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; COMPARATIVE STUDY; CONTROLLED STUDY; DRUG POTENCY; DRUG STRUCTURE; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME PHOSPHORYLATION; HUMAN; HUMAN CELL; INTOXICATION; LD 50; MALE; MOUSE; NONHUMAN; SURVIVAL;

ACETYLCHOLINESTERASE; ANIMALS; ANTIDOTES; BUTYRYLCHOLINESTERASE; CHEMICAL WARFARE AGENTS; ENZYME ACTIVATION; LETHAL DOSE 50; MALE; MICE; OXIMES; PHOSPHORIC ACID ESTERS; RATS; TRIMEDOXIME;

MUS; RATTUS;

EID: 63849218394     PISSN: 00041254     EISSN: None     Source Type: Journal    
DOI: 10.2478/10004-1254-60-2009-1890     Document Type: Article

References (28)

1. Dawson RM. Review of oximes available for the treatment of nerve agent poisoning. J Appl Toxicol 1994;14:317-31.
2. Johnson MK, Jacobsen D, Meredith TJ, Eyer P, Heath AJ, Ligtenstein DA, Marrs TC, Szinicz L, Vale JA, Haines JA. Evaluation of antidotes for poisoning by organophosphorus pesticides. Emerg Med 2000;12:22-37.
3. Sheridan RD, Beeson D, Tattersall JEH. Non-competitive block of the human muscle adult nicotinic acetylcholine receptor ion channel by the bispyridinium compounds, SAD-128 (SAD), toxogonin (TOX) and HI-6. Eur J Neurosci 2000;12(Suppl. S):36.
4. Stojiljković MP, Jokanović M. Pyridinium oximes: rationale for their selection as causal antidotes against organophosphate poisonings and current solutions for auto-injectors. Arh Hig Rada Toksikol 2006;57:435-43.
5. Shih TM, Koviak TA, Capacio BR. Anticonvulsants for poisoning by the organophosphorus compound soman: Pharmacological mechanisms. Neurosci Biobehav Rev 1991;15:349-62.
6. Shih TM, McDonough JH, Koplovitz I. Anticonvulsants for soman-induced seizure activity. J Biomed Sci 1999;6:86-96.
7. Thiermann H, Szinicz L, Eyer P, Felgenhauer N, Zilker T, Worek F. Lessons to be learnt from organophosphorus pesticide poisoning for the treatment of nerve agent poisoning. Toxicology 2007;233:145-54.
8. Thiermann H, Szinicz L, Eyer F, Worek F, Eyer P, Felgenhauer N, Zilker T. Modern strategies in therapy of organophosphate poisoning. Toxicol Lett 1999;107:233-9.
9. Eto M. Organic and biological chemistry. In: Zweig G, editor. The Organophosphorus Pesticides. Cleveland: CRC Press Inc.; 1976. p. 142.
10. Hamilton MG, Lundy PM. HI-6 therapy of soman and tabun poisoning in primates and rodents. Arch Toxicol 1989;63:144-9.
11. Maksimović M, Boškovic B, Radović L, Tadić V, Deljac V, Binenfeld Z. Antidotal effects of bis-pyridinium-2-monooxime carbonyl derivatives in intoxications with highly toxic organophosphorus compounds. Acta Pharm Jugoslav 1980;30:151-60.
12. Jokanović M, Maksimović M, Kilibarda V, Jovanović D, Savić D. Oxime-induced reactivation of acetylcholinesterase inhibited by phosphoramidates. Toxicol Lett 1996;85:35-9.
13. Čalić M, Lucić Vrdoljak A, Radić B, Jelić D, Jun D, Kuča K, Kovarik Z. In vitro and in vivo evaluation of pyridinium oximes: Mode of interaction with acetylcholinesterase, effect on tabun- and soman-poisoned mice and their cytotoxicity. Toxicology 2006;219:85-96.
14. Lucić Vrdoljak A, Čalić M, Radić B, Berend S, Jun D, Kuča K, Kovarik Z. Pretreatment with pyridinium oximes improves antidotal therapy against tabun poisoning. Toxicology 2006;228:41-50.
15. Kovarik Z, Čalić M, Bosak A, Šinko G, Jelić D. In vitro evaluation of aldoxime interactions with human acetylcholinesterase. Croat Chem Acta 2008;81:47-57.
16. Kovarik Z, Čalić M, Šinko G, Bosak A, Berend S, Lucić Vrdoljak A, Radić B. Oximes: Reactivators of phosphorylated acetylcholinesterase and antidotes in therapy against tabun poisoning. Chem Biol Interact 2008;175:173-9.
17. Berend S, Lucić Vrdoljak A, Radić B, Kuča K. New bispyridinium oximes: In vitro and in vivo evaluation of their biological effi ciency in soman and tabun poisoning. Chem Biol Interact 2008;175:413-6.
18. Čalić M, Bosak A, Kuča K, Kovarik Z. Interactions of butane, but-2-ene or xylene-like linked bispyridinium para-aldoximes with native and tabun-inhibited human cholinesterases. Chem Biol Interact 2008;175:305-8.
19. Musilek K, Jun D, Cabal J, Kassa J, Gunn-Moore F, Kuca K. Design of a potent reactivator of tabuninhibited acetylcholinesterase-synthesis and evaluation of (E)-1-(4-carbamoylpyridinium)-4-(4-hydroxyiminomethylpyridinium)- but-2-ene dibromide (K203). J Med Chem 2007;50:5514-8.
20. Kovarik Z, Čalić M, Šinko G, Bosak A. Structure-activity approach in the reactivation of tabun-phosphorylated human acetylcholinesterase with bispyridinium para-oximes. Arh Hig Rada Toksikol 2007;58:201-9.
21. Šinko G, Čalić M, Kovarik Z. para- and ortho-Pyridinium aldoximes in reaction with acetylcholinesterase. FEBS Letters 2006;580:3167-72.
22. Šinko G, Čalić M, Bosak A, Kovarik Z. Limitation of the Ellman method: Cholinesterase activity measurement in the presence of oximes. Anal Biochem 2007;370:223-7.
23. Thompson WR. Use of moving averages and interpolation to estimate median effective dose. Bacteriol Rev 1947;11:115-45.
24. Weil CS. Tables for convenient calculation of medianeffective dose (LD50 or ED50) and instruction in their use. Biometrics 1952;8:249-63.
25. Ellman GL, Courtney KD, Andres VJ, Featherstone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1960;7:88-95.
26. Thiermann H, Mast U, Klimmek R, Eyer P, Hibler A, Pfab R, Flegenhauer N, Zilker T. Cholinesterase status, pharmacokinetics and laboratory fi ndings during obidoxime therapy in organophosphate poisoned patients. Hum Exp Toxicol 1997;16:473-80.
27. Eddleston M, Szinicz L, Eyer P, Buckley N. Oximes in acute organophosphorus pesticide poisoning: a systemic review of clinical trials. Qjm-Mon J Assoc Phys 2002;95:275-83.
28. Kalász H, Hasan MY, Sheen R, Kuča K, Petroianu G, Ludányi K, Gergely A, Tekes K. HPLC analysis of K-48 concentration in plasma. Anal Bioanal Chem 2006;385:1062-7.