Have a personal or library account? Click to login
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 Cover

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

Open Access
|Dec 2015

References

  1. 1. Gupta R. Toxicology of Organophosphate and Carbamate Compounds. 1st ed. London: Elsevier Academic Press; 2005.
  2. 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: 10.2478/10004-1254-64-2013-229610.2478/10004-1254-64-2013-229623705196
  3. 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 409029973
  4. 4. Dawson MR. Review of oximes available for treatment of nerve agent poisoning. J Appl Toxicol 1994;14:317-31.PMID: 782268010.1002/jat.25501405027822680
  5. 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.
  6. 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/bi036191a15023072
  7. 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.2011.04.00621524695
  8. 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.2014.10.009
  9. 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.5b00060479109825835984
  10. 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.2005.11.00316332406
  11. 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.2006.08.01216982122
  12. 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/v10004-007-0013-717562604
  13. 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.
  14. 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/cca1815
  15. 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.sp006571135979213701136
  16. 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:30:1:145
  17. 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.2010.06.005
  18. 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.2005.10.025
  19. 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.2012.11.004
  20. 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.2010.02.023
  21. 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/BJ20121612
  22. 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: 10.2478/10004-1254-60-2009-189010.2478/10004-1254-60-2009-1890
  23. 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.2010.02.008
  24. 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)90145-9
  25. 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)00506-7
  26. 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: 11059068
  27. 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.
  28. 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/5.6part2.89
  29. 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/s00216-006-0490-616763789
  30. 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.169921717485
  31. 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: 929228710.1177/0960327197016008089292287
  32. 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/s00216-007-1507-517768608
  33. 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.2013.01.001
  34. 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/c1cc10787a21451868
  35. 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.M111.230656310332121464125
  36. 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.M111.333732332092822343626
  37. 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.2012.09.02323111374
  38. 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.2014.03.04424704618
  39. 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.2012.08.019353064322960624
  40. 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.2010.02.03320227398
  41. 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.0014213299705521151975
  42. 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.2010.03.00620223229
  43. 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. 2015.980813
  44. 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.
  45. 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.1215824741714
  46. 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.156120635332
  47. 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.2010.05.00920546883
  48. 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:1024960819430
DOI: https://doi.org/10.1515/aiht-2015-66-2740 | Journal eISSN: 1848-6312 | Journal ISSN: 0004-1254
Language: English, Croatian, Slovenian
Page range: 291 - 298
Submitted on: Nov 1, 2015
Accepted on: Nov 1, 2015
Published on: Dec 30, 2015
Published by: Institute for Medical Research and Occupational Health
In partnership with: Paradigm Publishing Services
Publication frequency: 4 issues per year

© 2015 Maja Katalinić, Nikolina Maček Hrvat, Jana Žďárová Karasová, Jan Misik, Zrinka Kovarik, published by Institute for Medical Research and Occupational Health
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.