Open Access

Translation of in vitro to in vivo pyridinium oxime potential in tabun poisoning / Translacija učinkovitosti piridinijevih oksima kod trovanja tabunom iz in vitro sustava u in vivo primjenu


Cite

1. Gupta R. Toxicology of Organophosphate and Carbamate Compounds. 1st ed. London: Elsevier Academic Press; 2005.Search in Google Scholar

2. Malekirad AA, Faghih M, Mirabdollahi M, Kiani M, Fathi A, Abdollahi M. Neurocognitive, mental health, and glucose disorders in farmers exposed to organophosphorus pesticides.Arh Hig Rada Toksikol 2013;64:1-7. doi: 10.2478/10004-1254-64-2013-229610.2478/10004-1254-64-2013-229623705196Search in Google Scholar

3. Gray AP. Design and structure-activity relationships of antidote to organophosphorus anticholinesterase agents.Drug Metab Rev 1984;15:557-89. doi: 10.3109/03602538 409029973Search in Google Scholar

4. Dawson MR. Review of oximes available for treatment of nerve agent poisoning. J Appl Toxicol 1994;14:317-31.PMID: 782268010.1002/jat.25501405027822680Search in Google Scholar

5. Doctor BP, Maxwell DM, Ashani Y, Saxena A, Gordon RK.New approaches to medical protection against chemical warfare nerve agents. In: Somani SM, Romano JA Jr, editors.Chemical warfare agents: toxicity at low levels. New York (NY): CRC Press; 2002. p. 191-214.Search in Google Scholar

6. Kovarik Z, Radić Z, Berman HA, Simeon-Rudolf V, Reiner E, Taylor P. Mutant cholinesterases possessing enhanced capacity for reactivation of their phosphonylated conjugates.Biochemistry 2004;43:3222-9. PMID: 1502307210.1021/bi036191a15023072Search in Google Scholar

7. Masson P. Evolution of and perspectives on therapeutic approaches to nerve agent poisoning. Toxicol Lett 2011;206:5-13. doi: 10.1016/j.toxlet.2011.04.00610.1016/j.toxlet.2011.04.00621524695Search in Google Scholar

8. Wilhelm CM, Snider TH, Babin MC, Jett DA, Platoff GE Jr, Yeung DT. A comprehensive evaluation of the efficacy of leading oxime therapies in guinea pigs exposed to organophosphorus chemical warfare agents or pesticides.Toxicol Appl Pharmacol 2014;281:254-65. doi: 10.1016/j. taap.2014.10.009Search in Google Scholar

9. Kovarik Z, Maček Hrvat N, Katalinić M, Sit RK, Paradyse A, Žunec S, Musilek K, Fokin VV, Taylor P, Radić Z.Catalytic soman scavenging by the Y337A/F338A acetylcholinesterase mutant assisted with novel site-directed aldoximes. Chem Res Toxicol 2015;28:1036-44. doi: 10.1021/acs.chemrestox.5b00060.10.1021/acs.chemrestox.5b00060479109825835984Search in Google Scholar

10. 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. doi: 10.1016/j.tox.2005.11.00310.1016/j.tox.2005.11.00316332406Search in Google Scholar

11. Lucić Vrdoljak A, Čalić M, Radić B, Berend S, Kuča K, Kovarik Z. Pretreatment with pyridinium oximes improves antidotal therapy against tabun poisoning. Toxicology 2006;228:41-50. doi: 10.1016/j.tox.2006.08.01210.1016/j.tox.2006.08.01216982122Search in Google Scholar

12. 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. doi: 10.2478/v10004-007-0013-710.2478/v10004-007-0013-717562604Search in Google Scholar

13. 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.Search in Google Scholar

14. Katalinić M, Kovarik Z. Reactivation of tabun-inhibited acetylcholinesterase investigated by two oximes and mutagenesis. Croat Chem Acta 2012;85:209-12. doi: 10.5562/cca181510.5562/cca1815Search in Google Scholar

15. Foy JM, Schnieden H. Estimation of total body water (virtual tritium space) in the rat, cat, rabbit, guinea-pig and man, and of the biological half-life of tritium in man. J Physiol 1960;154:169-76. doi: 10.1113/jphysiol.1960.sp00657110.1113/jphysiol.1960.sp006571135979213701136Search in Google Scholar

16. 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;30:145-7. doi: 10.1385/JMN:30:1:14510.1385/JMN:30:1:145Search in Google Scholar

17. Thiermann H, Eyer F, Felgenhauer N, Pfab R, Zilker T, Eyer P, Worek F. Pharmacokinetics of obidoxime in patients poisoned with organophosphorus compounds. Toxicol Lett 2010;197:236-42. doi: 10.1016/j.toxlet.2010.06.00510.1016/j.toxlet.2010.06.005Search in Google Scholar

18. Lenz DE, Maxwell DM, Koplovitz I, Clark CR, Capacio BR, Cerasoli DM, Federko JM, Luo C, Saxena A, Doctor BP, Olson C. Protection against soman or VX poisoning by human butyrylcholinesterase in guinea pigs and cynomolgus monkeys. Chem Biol Interact 2005;157-158:205-10. PMID: 1628906410.1016/j.cbi.2005.10.025Search in Google Scholar

19. Rosenberg YJ, Laube B, Mao L, Jiang X, Hernandez-Abanto S, Lee KD, Adams R. Pulmonary delivery of an aerosolized recombinant human butyrylcholinesterase pretreatment protects against aerosolized paraoxon in macaques. Chem Biol Interact 2013;203:167-71. doi: 10.1016/j. cbi.2012.11.004Search in Google Scholar

20. Kovarik Z, Katalinić M, Šinko G, Binder J, Holas O, Jung Y-S, Musilova L, Jun D, Kuča K. Pseudo-catalytic scavenging: searching for a suitable reactivator of phosphorylated butyrylcholinesterase. Chem Biol Interact 2010;187:167-71. doi: 10.1016/j.cbi.2010.02.02310.1016/j.cbi.2010.02.023Search in Google Scholar

21. Radić Z, Dale T, Kovarik Z, Berend S, Garcia E, Zhang L, Amitai G, Green C, Radić B, Duggan BM, Ajami D, Rebek JJr, Taylor P. Catalytic detoxification of nerve agent and pesticide organophosphates by butyrylcholinesterase assisted with nonpyridinium oximes. Biochem J 2013;450:231-42. doi: 10.1042/BJ20121612.10.1042/BJ20121612Search in Google Scholar

22. Kovarik Z, Lucić Vrdoljak A, Berend S, Čalić M, Kuča K, Musilek K, Radić B. Evaluation of oxime K203 as antidote in tabun poisoning. Arh Hig Rada Toksikol 2009;60:19-26. doi: 10.2478/10004-1254-60-2009-189010.2478/10004-1254-60-2009-1890Search in Google Scholar

23. Camp S, Zhang L, Krejci E, Dobbertin A, Bernard V, Girard E, Duysen EG, Lockridge O, De Jaco A, Taylor P.Contributions of selective knockout studies to understanding cholinesterase disposition and function. Chem Biol Interact 2010;187:72-7. doi: 10.1016/j.cbi.2010.02.00810.1016/j.cbi.2010.02.008Search in Google Scholar

24. Ellman GL, Courtney KD, Andres VJr, Featherstone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1961;7:88-90. doi: 10.1016/0006-2952(61)90145-910.1016/0006-2952(61)90145-9Search in Google Scholar

25. Eyer P, Worek F, Kiderlen D, Sinko G, Stuglin A, Simeon- Rudolf V, Reiner E. Molar absorption coefficients for the reduced Ellman reagent: reassessment. Anal Biochem 2003;312:224-7. doi: 10.1016/S0003-2697(02)00506-710.1016/S0003-2697(02)00506-7Search in Google Scholar

26. Reiner E, Šinko G, Škrinjarić-Špoljar M, Simeon-Rudolf V.Comparison of protocols for measuring activities of human blood cholinesterases by the Ellman method. Arh Hig Rada Toksikol 2000;51:13-8. PMID: 11059068Search in Google Scholar

27. Simeon-Rudolf V, Šinko G, Štuglin A, Reiner E. Inhibition of human blood acetylcholinesterase and butyrylcholinesterase by ethopropazine. Croat Chem Acta 2001;74:173-82.Search in Google Scholar

28. Kušić R, Bošković B, Vojvodić V, Jovanović D. HI-6 in man: blood levels, urinary excretion, and tolerance after intramuscular administration of the oxime to healthy volunteers. Fundam Appl Toxicol 1985;5(6part2):S89-S97. doi: 10.1093/toxsci/5.6part2.8910.1093/toxsci/5.6part2.89Search in Google Scholar

29. 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. PMID: 1676378910.1007/s00216-006-0490-616763789Search in Google Scholar

30. Zdarova Karasova J, Chladek J, Hroch M, Josef F, Hnidkova D, Kuca K. Pharmacokinetic study of two acetylcholinesterase reactivators, trimedoxime and newly synthesized oxime K027, in rat plasma. J Appl Toxicol 2011;33:18-23. doi: 10.1002/jat.169910.1002/jat.169921717485Search in Google Scholar

31. Worek F, Baecker M, Thiermann H, Szinicz L, Mast U, Klimmek R, Eyer P. Reappraisal of indications and limitations of oxime therapy in organophosphate poisoning.Hum Exp Toxicol 1997;16:466-72. PMID: 929228710.1177/0960327197016008089292287Search in Google Scholar

32. Benkö B, Kalász H, Ludányi K, Petroianu G, Kuca K, Darvas F, Tekes K. In vitro and in vivo metabolisms of K-48. Anal Bioanal Chem 2007;389:1243-7. PMID: 1776860810.1007/s00216-007-1507-517768608Search in Google Scholar

33. Zdarova Karasova J, Zemek F, Kassa J, Kuca K. Entry of oxime K027 into the different parts of rat brain: Comparison with obidoxime and oxime HI-6. J Appl Biomed 2014;12:25-9. doi: 10.1016/j.jab.2013.01.00110.1016/j.jab.2013.01.001Search in Google Scholar

34. Mercey G, Verdelet T, Saint-André G, Gillon E, Wagner A, Baati R, Jean L, Nachon F, Renard PY. First efficient uncharged reactivators for the dephosphylation of poisoned human acetylcholinesterase. Chem Commun (Camb) 2011;47:5295-7. doi: 10.1039/c1cc10787a10.1039/c1cc10787a21451868Search in Google Scholar

35. Sit RK, Radić Z, Gerardi V, Zhang L, Garcia E, Katalinić M, Amitai G, Kovarik Z, Fokin VV, Sharpless KB, Taylor P.New structural scaffolds for centrally acting oxime reactivators of phosphylated cholinesterases. J Biol Chem 2011;286:19422-30. doi: 10.1074/jbc.M111.23065610.1074/jbc.M111.230656310332121464125Search in Google Scholar

36. Radić Z, Sit RK, Kovarik Z, Berend S, Garcia E, Zhang L, Amitai G, Green C, Radić B, Fokin VV, Sharpless KB, Taylor P. Refinement of structural leads for centrally acting oxime reactivators of phosphylated cholinesterases. J Biol Chem 2012;287:11798-809. doi: 10.1074/jbc.M111.33373210.1074/jbc.M111.333732332092822343626Search in Google Scholar

37. Renou J, Mercey G, Verdelet T, Păunescu E, Gillon E, Arboléas M, Loiodice M, Kliachyna M, Baati R, Nachon F, Jean L, Renard P-Y. Syntheses and in vitro evaluations of uncharged reactivators for human acetylcholinesterase inhibited by organophosphorus nerve agents. Chem Biol Interact 2013;203:81-4. doi: 10.1016/j.cbi.2012.09.02310.1016/j.cbi.2012.09.02323111374Search in Google Scholar

38. Kliachyna M, Santoni G, Nussbaum V, Renou J, Sanson B, Colletier JP, Arboléas M, Loiodice M, Weik M, Jean L, Renard P-Y, Nachon F, Baati R. Design, synthesis and biological evaluation of novel tetrahydroacridine pyridinealdoxime and -amidoxime hybrids as efficient uncharged reactivatorsofnerveagent-inhibitedhumanacetylcholinesterase. Eur J Med Chem 2014;78:455-67. doi: 10.1016/j.ejmech.2014.03.04410.1016/j.ejmech.2014.03.04424704618Search in Google Scholar

39. Kovarik Z, Maček N, Sit RK, Radić Z, Fokin VV, Sharpless KB. Taylor P. Centrally acting oximes in reactivation of tabun-phosphoramidated AChE. Chem Biol Interact 2013;203:77-80. doi: 10.1016/j.cbi.2012.08.01910.1016/j.cbi.2012.08.019353064322960624Search in Google Scholar

40. Garcia EG, Campbell JA, Olson J, Moorad-Doctor D, Morthole IV. Novel oximes as blood-brain barrier penetrating cholinesterase reactivators. Chem Biol Interact 2010;187:199-206. doi: 10.1016/j.cbi.2010.02.03310.1016/j.cbi.2010.02.03320227398Search in Google Scholar

41. Wagner S, Kufleitner J, Zensi A, Dadparvar M, Wien S, Bungert J, Vogel T, Worek FG, Kreuter J, von Briesen H.Nanoparticulate transport of oximes over an in vitro bloodbrain barrier model. PLoS ONE 2010;5(12):e14213. doi: 10.1371/journal.pone.001421310.1371/journal.pone.0014213299705521151975Search in Google Scholar

42. Shih T-M, Skovira JW, O’Donnell JC, McDonough JH. In vivo reactivation by oximes of inhibited blood, brain and peripheral tissue cholinesterase activity following exposure to nerve agents in guinea pigs. Chem Biol Interact 2010;187:207-14. doi: 10.1016/j.cbi.2010.03.00610.1016/j.cbi.2010.03.00620223229Search in Google Scholar

43. Voicu V, Rădulescu FŞ, Medvedovici A. Relationships between the antidotal efficacy and structure, PK/PD parameters and bio-relevant molecular descriptors of AChE reactivating oximes: inclusion and integration to biopharmaceutical classification systems. Expert Opin Drug Metab Toxicol 2015;11:95-109. doi: 10.1517/17425255. 2015.980813Search in Google Scholar

44. Katalinić M, Miš K, Pirkmajer S, Grubič Z, Kovarik Z, Marš T. The cholinergic and non-cholinergic effects of organophosphates and oximes in cultured human myoblasts. Chem Biol Interact 2013;203:144-8. doi: 10.1016/j. cbi.2012.09.015.Search in Google Scholar

45. Žunec S, Kopjar N, Želježić D, Kuča K, Musilek K, Lucić Vrdoljak A. In vivo evaluation of cholinesterase activity, oxidative stress markers, cyto- and genotoxicity of K048 oxime-a promising antidote against organophosphate poisoning. Basic Clin Pharmacol Toxicol 2014;114:344-51. doi: 10.1111/bcpt.1215810.1111/bcpt.1215824741714Search in Google Scholar

46. Voicu VA, Bajgar J, Medvedovici A, Radulescu FS, Miron DS. Pharmacokinetics and pharmacodynamics of some oximes and associated therapeutic consequences: a critical review. J Appl Toxicol 2010;30:719-29. doi: 10.1002/ jat.156110.1002/jat.156120635332Search in Google Scholar

47. Zdarova Karasova J, Pohanka M, Musilek K, Zemek F, Kuca K. Passive diffusion of acetylcholinesterase oxime reactivators through the blood-brain barrier: influence of molecular structure. Toxicol in Vitro 2010;24:1838-44. doi: 10.1016/j.tiv.2010.05.00910.1016/j.tiv.2010.05.00920546883Search in Google Scholar

48. Sakurada K, Matsubara K, Shimizu K, Shiono H, Seto Y, Tsuge K, Yoshino M, Sakai I, Mukoyama H, Takatori T. Pralidoxime iodide (2-PAM) penetrates across the bloodbrain barrier. Neurochem Res 2003;28:1401-7. doi: 10.1023/A:1024960819430 10.1023/A:1024960819430Search in Google Scholar

eISSN:
0004-1254
Languages:
English, Slovenian
Publication timeframe:
4 times per year
Journal Subjects:
Medicine, Basic Medical Science, other