Minireview: Does in-vitro testing of oximes help predict their in-vivo action after paraoxon exposure?

Journal of Applied Toxicology

Volumn 29, Issue 6, 2009, Pages 459-469

  Lorke, D E ^a,b   Petroianu, G A ^a  

^a UNITED ARAB EMIRATES UNIVERSITY   (United Arab Emirates)

^b UNIVERSITY OF HAMBURG   (Germany)

Author keywords

Aldoxime; Cholinesterase; Hydrophilicity; Organophosphate; Paraoxon; Partition coefficient; Relative risk

Indexed keywords

1 (TERT BUTYLAMINO) 3 (6 CHLOROPHENOXY) 2 PROPANOL; ACETYLCHOLINESTERASE; ALDOXIME; K 108; K 113; K 27; K 48; OBIDOXIME; ORGANOPHOSPHORUS COMPOUND; OXIME DERIVATIVE; PARAOXON; PRALIDOXIME; PYRIDINIUM DERIVATIVE; THIOCHOLINE; UNCLASSIFIED DRUG;

BLOOD; CHEMICAL PARAMETERS; CORRELATION ANALYSIS; ENZYME ACTIVITY; ENZYME INHIBITION; ERYTHROCYTE; EXPOSURE; HUMAN; HYDROPHILICITY; IC 50; IN VITRO STUDY; IN VIVO STUDY; INTOXICATION; LD 50; LIPOPHILICITY; MORTALITY; NONHUMAN; PARTITION COEFFICIENT; PREDICTION AND FORECASTING; PRIORITY JOURNAL; REVIEW; RISK ASSESSMENT; TOXICITY;

ACETYLCHOLINESTERASE; ANIMALS; CHOLINESTERASE INHIBITORS; CHOLINESTERASE REACTIVATORS; DRUG ANTAGONISM; HUMANS; INHIBITORY CONCENTRATION 50; LETHAL DOSE 50; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS; OXIMES; PARAOXON; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RATS;

RATTUS;

EID: 68949114303     PISSN: 0260437X     EISSN: 10991263     Source Type: Journal    
DOI: 10.1002/jat.1457     Document Type: Review

References (43)

1. Antonijevic B, Stojiljkovic MP. 2007. Unequal efficacy of pyridinium oximes in acute organophosphate poisoning. Clin. Med. Res. 5: 71-82. (Pubitemid 350218782)
2. Bajgar J, Fusek J, Kuča K, Bartosova L, Jun D. 2007. Treatment of organophosphate intoxication using cholinesterase reactivators: facts and fiction. Med. Chem. 7: 461-466. (Pubitemid 46845793)
3. Bertolote JM, Fleischmann A, Eddleston M, Gunnell D. 2006. Deaths from pesticide poisoning: a global response. Br. J. Psychiat. 189: 201-203. (Pubitemid 44343463)
4. Buchwald P, Bodor N. 1998. Octanol-water partition: searching for predictive models. Curr. Med. Chem. 5: 353-380. (Pubitemid 28470788)
5. Buckley NA, Eddleston M, Dawson AH. 2005a. The need for translational research on antidotes for pesticide poisoning. Clin. Exp. Pharmacol. Physiol. 32: 999-1005. (Pubitemid 43906841)
6. Buckley N, Eddleston M, Szinicz L. 2005b. Oximes for acute organophosphate pesticide poisoning. Cochrane Database Syst. Rev. 1: CD005085.
7. Cox DR. 1972. Regression models and life tables. J. R. Statist. Soc. B 34: 189-220.
8. Crawford SL. 2006. Correlation and regression. Circulation 114: 2083-2088.
9. Csermely T, Kalasz H, Petroianu GA, Kuca K, Darvas F, Ludanyi K, Mudhafar AA, Tekes K. 2008. Analysis of pyridinium aldoximes - a chromatographic approach. Curr. Med. Chem. 15: 2401-2418.
10. Diener W, Schlede E. 1999. Acute toxic class methods: alternatives to LD/ LC50 Tests. ALTEX 16: 129-134.
11. Eddleston M, Mohamed F, Davies JO, Eyer P, Worek F, Sheriff MH, Buckley NA. 2006. Respiratory failure in acute organophosphorus pesticide self-poisoning. Q. J. Med. 99: 513-522. (Pubitemid 44304836)
12. Eddleston M, Buckley NA, Eyer P, Dawson AH. 2008. Management of acute organophosphorus pesticide poisoning. Lancet 371: 597-607. (Pubitemid 351232010)
13. Ellman GL, Courtney KD, Andres VJr, Feather-Stone RM. 1961. A new and rapid colorimetric determination of acetyl-cholinesterase activity. Biochem. Pharmacol. 7: 88-95.
14. Eyer P. 2003. The role of oximes in the management of organophosphorus pesticide poisoning. Toxicol. Rev. 22: 165-190. (Pubitemid 38659720)
15. Gunnell D, Eddleston M, Phillips MR, Konradsen F. 2007. The global distribution of fatal pesticide self-poisoning: systematic review. BMC. Public Health 7: 357. (Pubitemid 351341888)
16. Gupta RC. 2004. Brain regional heterogeneity and toxicological mechanisms of organophosphates and carbamates. Toxicol. Mech. Meth. 14: 103-143.
17. Gupta RC. 2006. Classification and uses of organophosphates and carbamates. In: Toxicology of Organophosphate and Carbamate Compounds, Gupta RC (ed.). Elsevier: Amsterdam; 5-24.
18. Hansch C, Fujita T. 1964. ρ-σ-π analysis. A method for the correlation of biological activity and chemical structure. J. Am. Chem. Soc. 86: 1616-1626.
19. Johnson MK, Jacobsen D, Meredith TJ, Eyer P, Heath AJ, Ligtenstein DA, Marrs TC, Szinicz L, Vale JA, Haines JA. 2000. Evaluation of antidotes for poisoning by organophosphourus pesticides. Emerg. Med. 12: 22-37. (Pubitemid 30321724)
20. Kuča K, Jun D, Bajgar J. 2007a. Currently used cholinesterase reactivators against nerve agent intoxication: comparison of their effectivity in vitro. Drug Chem. Toxicol. 30: 31-40. (Pubitemid 46269293)
21. Kuča K, Cabal J, Jun D, Musilek K. 2007b. In vitro reactivation potency of acetylcholinesterase reactivators - K074 and K075 - to reactivate tabun-inhibited human brain cholinesterases. Neurotox. Res. 11: 101-106.
22. Leo A, Hansch C, Elkins D. 1971. Partition coefficients and their uses. Chem. Rev. 71: 525-616.
23. Lorke DE, Hasan MY, Nurulain SM, Sheen R, Kuča K, Petroianu GA. 2007. Entry of two new asymmetric bispyridinium oximes (K-27 and K-48) into the rat brain: comparison with obidoxime. J. Appl. Toxicol. 27: 482-490. (Pubitemid 47255501)
24. Lorke DE, Hasan MY, Nurulain SM, Shafiullah M, Nagelkerke N, Petroianu GA. 2008a. Effect of intrathecal pralidoxime administration upon sur vival of rats exposed to the organophosphate paraoxon. Neurotoxicology 29: 663-670.
25. Lorke DE, Hasan MY, Arafat K, Kuča K, Musilek K, Schmitt A, Petroianu GA. 2008b. In vitro oxime reactivation of red blood cell acetylcholinesterase inhibited by diisopropyl-fluorophosphate (DFP). J. Appl. Toxicol, 28: 422-429. (Pubitemid 351716527)
26. Lorke DE, Hasan MY, Nurulain SM, Kuča K, Kassa J, Petroianu GA. 2008c. Eight new bispyridinium oximes in comparison with the conventional oximes pralidoxime and obidoxime: in vivo efficacy to protect from diisopropylfluorophosphate (DFP) toxicity. J. Appl. Toxicol. 28: 920-928.
27. Lorke DE, Kalasz H, Petroianu GA, Tekes K. 2008d. Entry of oximes into the brain: a review. Curr. Med. Chem. 15: 743-753.
28. Lorke DE, Hasan MY, Arafat K, Nurulain SM, Kuča K, Petroianu GA. 2009. Species differences in oxime protection of acetylcholinesterase inhibited by different organophosphates. An in vitro study on red blood cells. In preparation.
29. Musilek K, Holas O, Kuča K, Jun D, Dohnal V, Dolezal M. 2007. Synthesis of a novel series of non-symmetrical bispyridinium compounds bearing a xylene linker and evaluation of their reactivation activity against tabun and paraoxon-inhibited acetylcholinesterase. J. Enzyme Inhib. Med. Chem. 22: 425-432. (Pubitemid 47225704)
30. Nurulain SM, Lorke DE, Hasan MY, Shafiullah M, Kuca K, Musilek K, Petroianu GA. 2009. Efficacy of eight experimental bispyridinium oximes against paraoxon-induced mortality: comparison with the conventional oximes pralidoxime and obidoxime. Neurotox. Res. 16: 60-67.
31. Peter JV, Moran JL, Graham P. 2006. Oxime therapy and outcomes in human organophosphate poisoning: an evaluation using metaanalytic techniques. Crit. Care Med. 34: 502-510. (Pubitemid 43145632)
32. Petroianu GA, Kalasz HJ. 2007. Comparison of the ability of oximes to reactivate human RBC cholinesterases inhibited by ethyl- and methylparaoxon. Curr. Org. Chem. 11: 1624-1634.
33. Petroianu GA, Lorke DE. 2008. Pyridinium oxime reactivators of cholinesterase inhibited by diisopropyl-fluorophosphate (DFP): predictive value of in-vitro testing for in-vivo efficacy. Mini Rev. Med. Chem. 8: 1328-1342.
34. Petroianu GA, Arafat K, Kuča K, Kassa J. 2006a. 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. 26: 64-71. (Pubitemid 43171336)
35. Petroianu GA, Nurulain SM, Nagelkerke N, Al-Sultan MA, Kuča K, Kassa J. 2006b. 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. 26: 262-268. (Pubitemid 43773887)
36. Petroianu GA, Lorke DE, Hasan MY, Adem A, Sheen R, Nurulain SM, Kalasz H. 2007a. Paraoxon has only a minimal effect on pralidoxime brain concentration in rats. J. Appl. Toxicol. 27: 350-357. (Pubitemid 47066763)
37. Petroianu GA, Hasan MY, Nurulain SM, Nagelkerke N, Kassa J, Kuča K. 2007b. New K-oximes (K-27 and K-48) in comparison with obidoxime (LuH-6), pralidoxime, HI-6 and trimedoxime (TMB-4): survival in rats exposed to the organophosphate paraoxon. Toxicol. Mech. Meth. 17: 401-408. (Pubitemid 47360086)
38. Rahimi R, Nikfar S, Abdollahi M. 2006. Increased morbidity and mortality in acute human organophosphate-poisoned patients treated by oximes: a meta-analysis of clinical trials. Hum. Exp. Toxicol. 25: 157-162.
39. Scherrmann JM. Drug delivery to brain via the blood-brain barrier. 2002. Vasc. Pharmacol. 38: 349-354. (Pubitemid 36398256)
40. Wiener SW, Hoffman RS. 2004. Nerve agents: a comprehensive review. J. Intensive Care Med. 19: 22-37.
41. Worek F, Mast U, Kiderlen D, Diepold C, Eyer P. 1999. Improved determination of acetylcholinesterase activity in human whole blood. Clin. Chim. Acta 288: 73-90. (Pubitemid 29472417)
42. Worek F, Reiter G, Eyer P, Szinicz L. 2002. Reactivation kinetics of acetylcholinesterase from different species inhibited by highly toxic organophosphates. Arch. Toxicol. 76: 523-529.
43. Worek F, Eyer P, Aurbek N, Szinicz L, Thiermann H. 2007. Recent advances in evaluation of oxime efficacy in nerve agent poisoning by in vitro analysis. Toxicol. Appl. Pharmacol. 219: 226-234. (Pubitemid 46282867)