In vitro oxime-assisted reactivation of paraoxon-inhibited human acetylcholinesterase and butyrylcholinesterase

Clinical Toxicology

Volumn 47, Issue 6, 2009, Pages 545-550

  Musilova, Lucie ^a   Kuca, Kamil ^b,c,d   Jung, Young Sik ^e   Jun, Daniel ^b,c,f  

^a Charles University in Prague Faculty of Pharmacy   (Czech Republic)

^b UNIVERSITY OF DEFENCE   (Czech Republic)

^c UNIVERSITY OF DEFENCE   (Czech Republic)

^d J E PURKINJE UNIVERSITY   (Czech Republic)

^e Korea Research Institute of Chemical Technology   (South Korea)

^f CZECH UNIVERSITY OF LIFE SCIENCES PRAGUE   (Czech Republic)

Author keywords

Acetylcholinesterase; Bioscavenger; Butyrylcholinesterase; Organophosphate; Oxime; Paraoxon; Pesticide; Reactivator

Indexed keywords

1 (4 CARBAMOYLPYRIDINIO) 1' (2 HYDROXYIMINOMETHYLPYRIDINIO)DIMETHYL ETHER; ACETYLCHOLINESTERASE; ANTIDOTE; CHOLINESTERASE; METHOXIME; OBIDOXIME; OXIME; OXIME DERIVATIVE; PARAOXON; PRALIDOXIME; SCAVENGER; TRIMEDOXIME; UNCLASSIFIED DRUG; CHOLINESTERASE INHIBITOR; CHOLINESTERASE REACTIVATOR;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CONTROLLED STUDY; ENZYME ACTIVATION; ENZYME INHIBITION; EVALUATION; HUMAN; IN VITRO STUDY; INTOXICATION; CELL CULTURE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; ENZYMOLOGY; ERYTHROCYTE; METABOLISM; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ACETYLCHOLINESTERASE; ANTIDOTES; CELLS, CULTURED; CHOLINESTERASE INHIBITORS; CHOLINESTERASE REACTIVATORS; ERYTHROCYTES; HUMANS; MOLECULAR STRUCTURE; PARAOXON; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 67651153132     PISSN: 15563650     EISSN: 15569519     Source Type: Journal    
DOI: 10.1080/15563650903058914     Document Type: Article

References (39)

1. Aygun D, Doganay Z, Altintop L, Guven H, Onar M, Deniz T, Sunter T. Serum acetylcholinesterase and prognosis of acute organophosphate poisoning. Clin Toxicol 2002; 40:903-910.
2. Kuca K, Cabal J, Jun D, Hrabinova M. Potency of five structurally different acetylcholinesterase reactivators to reactivate human brain cholinesterases inhibited by cyclosarin. Clin Toxicol 2007; 45:512-515.
3. Bajgar J, Kuca K, Jun D, Bartosova L, Fusek J. Cholinesterase reactivators: the fate and effects in the organism poisoned with organophosphates/ nerve agents. Curr Drug Metab 2007; 8:803-809.
4. Kuca K, Juna D, Musilek K. Structural requirements of acetylcholinesterase reactivators. Mini Rev Med Chem 2006; 6:269-277.
5. Petroianu GA, Arafat K, Kuca K, Kassa J. Five oximes (K-27, K-33, K-48, BI-6 and methoxime) in comparison with pralidoxime: in vitro reactivation of red blood cell acetylcholinesterase inhibited by paraoxon. J Appl Toxicol 2006; 26:64-71. (Pubitemid 43171336)
6. Qian Y, Venkatraj J, Barhoumi R, Pal R, Datta A, Wild JR, Tiffany-Castiglioni E. Comparative non-cholinergic neurotoxic effects of paraoxon and diisopropyl fluorophosphate (DFP) on human neuroblastoma and astrocytoma cell lines. Toxicol Appl Pharmacol 2007; 219:162-1671.
7. Saxena A, Sun W, Luo C, Myers TM, Koplovitz I, Lenz DE, Doctor BP. Bioscavenger for protection from toxicity of organophosphorus compounds. J Mol Neurosci 2006; 30:145-148.
8. Kolarich D, Weber A, Pabst M, Stadlmann J, Teschner W, Ehrlich H, Schwarz HP, Altmann F. Glycoproteomic characterization of butyrylcholinesterase from human plasma. Proteomics 2008; 8:254-263
9. Grunwald J, Marcus D, Papier Y, Raveh L, Pittel Z, Ashani Y. Largescale purification and long-term stability of human butyrylcholinesterase: a potential bioscavenger drug. J Biochem Biophys Methods 1997; 34:123-135.
10. Lockridge O, Blong RM, Masson P, Froment MT, Millard CB, Broomfield CA. A single amino acid substitution, Gly117His, confers phosphotriesterase (organophosphorus acid anhydride hydrolase) activity on human butyrylcholinesterase. Biochemistry 1997; 36:786-795.
11. Pan Y, Gao D, Yang W, Cho H, Yang G, Tai HH, Zhan CG. Computational redesign of human butyrylcholinesterase for anticocaine medication. Proc Natl Acad Sci USA 2005; 102:16656-16661.
12. Wang Y, Schopfer LM, Duysen EG, Nachon F, Masson P, Lockridge O. Screening assays for cholinesterases resistant to inhibition by organophosphorus toxicants. Anal Biochem 2004; 329:131-138.
13. Wang Y, Boeck AT, Duysen EG, Van KM, Saunders TL, Lockridge O. Resistance to organophosphorus agent toxicity in transgenic mice expressing the G117H mutant of human butyrylcholinesterase. Toxicol Appl Pharmacol 2004; 196:356-366.
14. Doctor BP, Saxena A. Bioscavengers for the protection of humans against organophosphate toxicity. Chem Biol Interact 2005; 157-158: 167-171.
15. First Time in Human Study of Protexia. 2008. http://clinicaltrials.gov/ ct2/show/NCT00744146. Accessed 4 March 2009.
16. A Study of Plasma-Derived Human Butyrylcholinesterase Administered Intramuscularly. 2007. http://clinicaltrials.gov/ct2/show/NCT00333528. Accessed 4 March 2009.
17. Pharmacokinetic (PK) and Safety Study of Plasma-Derived Human Butyrylcholinesterase Administered Intravenously. 2007. http:// clinicaltrials.gov/ct2/show/NCT00333515. Accessed 4 March 2009.
18. Ellman GL, Courtney KD, Andres V, Jr, Feather-Stone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1961; 7:88-95.
19. Jun D, Musilova L, Kuca K, Kassa J, Bajgar J. Potency of several oximes to reactivate human acetylcholinesterase and butyrylcholinesterase inhibited by paraoxon in vitro. Chem Biol Interact 2008; 175:421-424.
20. Bajgar J. Organophosphates/nerve agent poisoning: mechanism of action, diagnosis, prophylaxis, and treatment. Adv Clin Chem 2004; 38:151-216.
21. Petroianu GA, Arafat K, Nurulain SM, Kuca K, Kassa J. In vitro oxime reactivation of red blood cell acetylcholinesterase inhibited by methylparaoxon. J Appl Toxicol 2007; 27:168-175.
22. Okuno S, Sakurada K, Ohta H, Ikegaya H, Kazui Y, Akutsu T, Takatori T, Iwadate K. Blood-brain barrier penetration of novel pyridinealdoxime methiodide (PAM)-type oximes examined by brain microdialysis with LC-MS/MS. Toxicol Appl Pharmacol 2008; 227:8-15.
23. Musilek K, Holas O, Kuca K, Jun D, Dohnal V, Dolezal M. Synthesis of asymmetrical bispyridinium compounds bearing cyano-moiety and evaluation of their reactivation activity against tabun and paraoxoninhibited acetylcholinesterase. Bioorg Med Chem Lett 2006; 16:5673-5676. (Pubitemid 44415434)
24. 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. (Pubitemid 46705550)
25. Oh KA, Park NJ, Park NS, Kuca K, Jun D, Jung YS. Reactivation of DFP- and paraoxon-inhibited acetylcholinesterases by pyridinium oximes. Chem Biol Interact 2008; 175:365-367.
26. Petroianu GA, Nurulain SM, Nagelkerke N, Al-Sultan MA, Kuca K, Kassa J. Five oximes (K-27, K-33, K-48, BI-6 and methoxime) in comparison with pralidoxime: survival in rats exposed to the organophosphate paraoxon. J Appl Toxicol 2006; 26:262-268. (Pubitemid 43773887)
27. 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 methylparaoxon. J Appl Toxicol 2007; 27:453-457.
28. Musilek K, Kuca K, Jun D, Dohnal V, Dolezal M. Synthesis of a novel series of bispyridinium compounds bearing a xylene linker and evaluation of their reactivation activity against chlorpyrifos-inhibited acetylcholinesterase. J Enzyme Inhib Med Chem 2005; 20:409-415.
29. Kuca K, Kassa J. In vitro reactivation of acetylcholinesterase using the oxime K027. Vet Hum Toxicol 2004; 46:15-18.
30. Worek F, Eyer P, Kiderlen D, Thiermann H, Szinicz L. Effect of human plasma on the reactivation of sarin-inhibited human erythrocyte acetylcholinesterase 3. Arch Toxicol 2000; 74:21-26.
31. Kiderlen D, Worek F, Klimmek R, Eyer P. The phosphoryl oximedestroying activity of human plasma. Arch Toxicol 2000; 74:27-32.
32. 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; 18:529-535.
33. Kassa J, Jun D, Karasova J, Bajgar J, Kuca K. A comparison of reactivating efficacy of newly developed oximes (K074, K075) and currently available oximes (obidoxime, HI-6) in soman, cyclosarin and tabunpoisoned rats. Chem Biol Interact 2008; 175:425-427.
34. Kuca K, Cabal J, Musilek K, Jun D, Bajgar J. Effective bisquaternary reactivators of tabun-inhibited AChE. J Appl Toxicol 2005; 25:491-495.
35. Kuca K, Cabal J, Jun D, Musilek K. In vitro reactivation potency of acetylcholinesterase reactivators - K074 and K075 - to reactivate tabuninhibited human brain cholinesterases. Neurotox Res 2007; 11:101-106.
36. Kovarik Z, Calic M, Sinko G, Bosak A, Berend S, Vrdoljak AL, Radic B. Oximes: reactivators of phosphorylated acetylcholinesterase and antidotes in therapy against tabun poisoning. Chem Biol Interact 2008; 175:173-179.
37. Calic M, Bosak A, Kuca 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; 175:305-308.
38. Kim TH, Oh KA, Park NJ, Park NS, Kim YJ, Yum EK, Jung YS. Reactivation Study of Pyridinium Oximes for Acetylcholinesterases Inhibited by Paraoxon or DFP. J Appl Biomed 2006; 4:67-72.
39. Karasova JZ, Kassa J, Jung YS, Musilek K, Pohanka M, Kuca K. Effect of several new and currently available oxime cholinesterase reactivators on tabun-intoxicated Rats. Int J Mol Sci 2008; 9(11):2243-2252.