In vivo evaluation of cholinesterase activity, oxidative stress markers, cyto- and genotoxicity of K048 Oxime - a promising antidote against organophosphate Poisoning

Basic and Clinical Pharmacology and Toxicology

Volumn 114, Issue 4, 2014, Pages 344-351

  Žunec, Suzana ^a   Kopjar, Nevenka ^a   Želježić, Davor ^a   Kuča, Kamil ^b   Musilek, Kamil ^c   Vrdoljak, Ana Lucić ^a  

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

^b UNIVERSITY HOSPITAL HRADEC KRALOVE   (Czech Republic)

^c UNIVERSITY OF HRADEC KRALOVE   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

1 (4 CARBAMOYLPYRIDINIO) 4 (4 HYDROXYIMINOMETHYLPYRIDINIO)BUTANE DIBROMIDE; ACRIDINE ORANGE; ANTIDOTE; CHOLINESTERASE; ETHIDIUM BROMIDE; SUPEROXIDE DISMUTASE; TABUN; THIOBARBITURIC ACID REACTIVE SUBSTANCE;

ACUTE TOXICITY; ANIMAL EXPERIMENT; ANIMAL MODEL; APOPTOSIS; ARTICLE; CELL DEATH; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DNA DAMAGE; ENZYME ACTIVITY; GENOTOXICITY; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; LD 50; LIPID PEROXIDATION; LYMPHOCYTE; MALE; MOUSE; NONHUMAN; ORGANOPHOSPHATE POISONING; OXIDATIVE STRESS; PRIORITY JOURNAL;

MUS; RATTUS;

ACETYLCHOLINESTERASE; ANIMALS; ANTIDOTES; CELL SURVIVAL; CHOLINESTERASE INHIBITORS; COMET ASSAY; DNA DAMAGE; LETHAL DOSE 50; LIPID PEROXIDATION; LYMPHOCYTES; MALE; ORGANOPHOSPHATE POISONING; ORGANOPHOSPHATES; OXIDATIVE STRESS; OXIMES; PHOSPHORYLATION; PYRIDINIUM COMPOUNDS; RATS; RATS, WISTAR; SUPEROXIDE DISMUTASE; THIOBARBITURIC ACID REACTIVE SUBSTANCES; TOXICITY TESTS, ACUTE;

EID: 84895485707     PISSN: 17427835     EISSN: 17427843     Source Type: Journal    
DOI: 10.1111/bcpt.12158     Document Type: Article

References (65)

1. Somani SM, Husain K. Low-level nerve agent toxicity under normal and stressful conditions. In: Somani SM, Romano JA Jr (eds) Chemical Warfare Agents: Toxicity at Low Levels. CRC Press LLC, Boca Raton 2001;83-120.
2. Chambers J, Patricia EL. Organophosphates: Chemistry, Fate and Effects. Academic Press Inc., New York, 1992.
3. Antonijević B, Stojiljković MP. Unequal efficacy of pyridinium oximes in acute organophosphate poisoning. Clin Med Res 2007;5:71-82.
4. Jokanović M, Stojiljković MP. Current understanding of the application of pyridinium oximes as cholinesterase reactivators in treatment of organophosphate poisoning. Eur J Pharmacol 2006;553:10-7.
5. Voicu VA, Thiermann H, Rǎdulescu FŞ, Mircioiu C, Miron DS. The toxicokinetics and toxicodynamics of organophosphonates versus the pharmacokinetics and pharmacodynamics of oxime antidotes: biological consequences. Basic Clin Pharmacol Toxicol 2009;106:73-85.
6. Reiner E. Organophosphorus compounds and esterases: current research topics concerning the toxicity of and protection against organophosphates. Arh Hig Rada Toksikol 2001;52:323-31.
7. Balali-Mood M, Shariat M. Treatment of organophosphate poisoning. Experience of nerve agents and acute pesticide poisoning on the effect of oximes. J Physiol Paris 1998;92:375-8.
8. Luo C, Saxena A, Smith M, Garcia G, Radić Z, Taylor P et al. Phosphoryl oxime inhibition of acetylcholinesterase during oxime reactivation is prevented by edrophonium. Biochemistry 1999;38:9937-47.
9. Kiderlen D, Worek F, Klimmek R, Eyer P. The phosphoryloxime-destroying activity of human plasma. Arch Toxicol 2000;74:27-32.
10. Lugokenski TH, Gubert P, Bueno DC, Nogara PA, de Aquino Saraiva R, Barcelos RP et al. Effect of different oximes on rat and human cholinesterases inhibited by methamidophos: a comparative in vitro and in silico study. Basic Clin Pharmacol Toxicol 2012;111:362-70.
11. Kuča K, Bielavsky J, Cabal J, Bielavska M. Synthesis of a potential reactivator of acetylcholinesterase 1-(4-hydroxyiminomethylpyridinium)-3-(carbamoylpyridinium)-propane dibromide. Tetrahedron Lett 2003a;44:3123-5.
12. Kuča K, Bielavsky J, Cabal J, Kassa J. Synthesis of a new reactivator of tabun-inhibited acetylcholinesterase. Bioorg Med Chem 2003b;13:3545-7.
13. Musilek K, Holas O, Hambalek J, Kuča K, Jun D, Dohnal V et al. Synthesis of bispyridinium compounds bearing propane linker and evaluation of their reactivation activity against tabun- and paraoxon-inhibited acetylcholinesterase. Lett Org Chem 2006;3:831-5.
14. Čalić M, Lucić Vrdoljak A, Radić B, Jelić D, Jun D, Kuča K et al. 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.
15. Berend S, Lucić Vrdoljak A, Radić B, Kuča K. New bispyridinium oximes: in vitro and in vivo evaluation of their biological efficiency in soman and tabun poisoning. Chem Biol Interact 2008;175:413-6.
16. Kovarik Z, Lucić Vrdoljak A, Berend S, Katalinić M, Kuča K, Musilek K et al. Evaluation of oxime K203 as antidote in tabun poisoning. Arh Hig Rada Toksikol 2009;60:19-26.
17. Kassa J, Misik J, Karasova JZ. Evaluation of the potency of two novel bispyridinium oximes (K456, K458) in comparison with oxime K203 and trimedoxime to counteract tabun-induced neurotoxicity in rats. Basic Clin Pharmacol Toxicol 2013;113:201-8.
18. Kassa J, Karasova JZ, Sepsova V, Caisberger F. The benefit of combinations of oximes for the reactivating and therapeutic efficacy of antidotal treatment of sarin poisoning in rats and mice. Basic Clin Pharmacol Toxicol 2011;109:30-4.
19. Kassa J, Misik J, Karasova JZ. A comparison of the potency of a novel bispyridinium oxime K203 and currently available oximes (Obidoxime, HI-6) to counteract the acute neurotoxicity of sarin in rats. Basic Clin Pharmacol Toxicol 2012;111:333-8.
20. Park NJ, Jung YS, Musilek K, Jun D, Kuča K. Potency of several structurally different acetylcholinesterase reactivators to reactivate house fly and bovine acetylcholinesterases inhibited by paraoxon and DFP. Bull Korean Chem Soc 2006;27:1401-4.
21. Kuča K, Musilek K, Jun D, Pohanka M, Kumar Ghosh K, Hrabinova M. Oxime K027: novel low-toxic candidate for the universal reactivator of nerve agent- and pesticide-inhibited acetylcholinesterase. J Enzyme Inhib Med Chem 2010;25:509-12.
22. Lucić Vrdoljak A, Čalić M, Radić B, Berend S, Jun D, Kuča K et al. Pretreatment with pyridinium oximes improves antidotal therapy against tabun poisoning. Toxicology 2006;228:41-50.
23. Berend S. Učinkovitost bispiridinijevih oksima u terapiji trovanja tabunom i somanom. PhD thesis (in Croatian) Faculty of Science, Zagreb, Croatia, 2012;1-109.
24. Veinlichova A, Jancova P, Siller M, Anzenbacher P, Kuča K, Jun D et al. Effect of acetylcholinesterase oxime-type reactivators K048 and HI-6 on human liver microsomal cytochromes P450 in vitro. Chem Biol Interact 2009;180:449-53.
25. Thompson WR. Use of moving averages and interpolation to estimate median effective dose. Bacteriol Rev 1947;11:115-45.
26. Weil CS. Tables for convenient calculation of median effective dose (LD50 or ED50) and instruction in their use. Biometrics 1952;8:249-63.
27. Ellman GL, Courtney KD, Andres VJ, Featherstone RM. A new and rapid colorimetric detremination of acetylcholinesterase activity. Biochem Pharmacol 1961;7:88-95.
28. Meuling WJA, Jongen MJM, van Hemmen JJ. An automated method for the determination of acetyl and pseudo cholinesterase in hemolyzed whole blood. Am J Ind Med 1992;22:231-41.
29. Taylor P, Radic Z, Hosea NA, Camp S, Marchot P, Berman HA. Structural bases for the specificity of cholinesterase catalysis and inhibition. Toxicol Lett 1995;82-83:453-8.
30. Worek F, Mast U, Kiderlen C, Diepold P, Eyer P. Improved determination of acetylcholinesterase activity in human whole blood. Clin Chim Acta 1999;288:73-90.
31. Reiner E, Simeon-Rudolf V. Cholinesterase activity assays: an overview of procedures suggested for human whole blood analysis. In: Bokan S, Orehovec Z, Price B (eds). The Proceedings of the Chemical and Biological Medical Treatment Symposium CB MTS - Industry III. Applied Science and Analysis Aberdeen, Maryland, USA 2004;362-5.
32. Li B, Sedlacek M, Manoharan I, Boopathy R, Duysen EG, Masson P et al. Butyrylcholinesterase, paraoxonase, and albumin esterase, but not carboxylesterase, are present in human plasma. Biochem Pharmacol 2005;70:1673-84.
33. Drury JA, Nycyk JA, Cooke RWI. Comparison of urinary and plasma malodialdehyde in preterm infants. Clin Chim Acta 1997;263:177-85.
34. Flohé L, Ötting F. Superoxide dismutase assays. Methods Enzymol 1971;105:93-104.
35. Bradford MM. A rapid and sensitive assay for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 1976;72:248-54.
36. http://www.sigmaaldrich.com/etc/medialib/docs/Sigma/General_Information/1/1077.Par.0001.File.tmp/1077.pdf/July 2013
37. Duke RC, Cohen JJ. Morphological and biochemical assays of apoptosis. In: Coligan JE, Kruisbeal AM (eds). Current Protocols in Immunology. John Willey and Sons, New York, 1992;1-3.
38. Singh NP, McCoy MT, Tice RR, Schneider LL. A simple technique for quantitation of low levels of DNA damage in individual cells. Exp Cell Res 1988;175:184-91.
39. Moretti M, Villarini M, Scassellati Sforzilini G, Pasquini R. Pesticide-induced primary DNA damage n peripheral blood leukocytes of farm workers evaluated by the computerized "comet" assay. Biomarkers 2005;5:192-204.
40. Gabianelli R, Lupidi G, Villarini M, Falcioni G. DNA damage induced by copper on erythrocytes of gilthead sea bream Sparus aurata and mollusk Scapharca inaequivalvis. Arch Environ Contam Toxicol 2003;45:350-6.
41. Masson P. Evolution of and perspectives on therapeutic approaches to nerve agent poisoning. Toxicol Lett 2011;206:5-13.
42. Vučinić S, Zlatković M, Antonijević B, Ćurčić M, Bošković B. Fresh frozen plasma as a successful antidotal supplement in acute organophosphate poisoning. Arh Hig Rada Toksikol 2013;64:273-7.
43. Nurulain SM. In vivo efficacy of eight new bisquaternary K-oximes in comparison to 2-PAM and obidoxime against rat with paraoxon and DFP intoxication. PhD thesis, University of Pharmaceutical Sciences PhD School, Budapest, 2010;1-110.
44. Thompson CM, Richardson RJ. Anticholinesterase insecticides. In: Marrs TC, Ballantyne B (eds). Pesticide Toxicology and International Regulation. John Wiley & Sons Ltd., Chichester, 2004;89-127.
45. Giacobini E. Cholinesterases in human brain: the effect of cholinesterase inhibitors on Alzheimer's disease and related disorders. In: Giacobini E, Pepeu G (eds). The Brain Cholinergic System in Health and Disease. Informa Healthcare, Oxon, 2006;235-64.
46. Faff J, Bak W. Increased sensitivity to obidoxime induced by fluostigmine in the rat. Toxicol Appl Pharmacol 1978;46:429-33.
47. Hiraoka A, Ohtaka J, Koike S, Tsuboi Y, Tsuchikawa S, Miura I. Inhibition of copper-containing amine oxidase by oximes. Chem Pharm Bull (Tokyo) 1988;36:3027-31.
48. Mličkova K, Šebela M, Cibulka R, Frebort I, Peč P, Liška F et al. Inhibition of copper amine oxidases by pyridine-derived aldoximes and ketoximes. Biochimie 2001;83:995-1002.
49. Sakurada K, Ikegaya H, Ohta H, Fukushima H, Akutsu T, Watanabe K. Effects of oximes on mitochondrial oxidase activity. Toxicol Lett 2009;189:110-4.
50. Ziech D, Franco R, Georgakilas AG, Georgakila S, Malamou-Mitsi V, Schoneveld O et al. The role of reactive oxygen species and oxidative stress in environmental carcinogenesis and biomarker development. Chem Biol Interact 2010;188:334-9.
51. Pohanka M, Zdarova-Karasova J, Musilek K, Kuča K, Kassa J. Effect of five acetylcholinesterase reactivators on tabun-intoxicated rats: induction of oxidative stress versus reactivation efficacy. J Appl Toxicol 2009;29:483-8.
52. da Silva AP, Farina M, Franco JL, Dafre AL, Kassa J, Kuča K. Temporal effects of newly developed oximes (K027, K048) on malathion-induced acetylcholinesterase inhibition and lipid peroxidation in mouse prefrontal cortex. Neurotoxicology 2008;29:184-9.
53. Puntel GO, Gubert P, Peres GL, Bresolin L, Rocha JBT, Pereira ME et al. Antioxidant properties of oxime 3-(phenylhydrazono) butan-2-one. Arch Toxicol 2008;82:755-62.
54. Novak I, Komorsky-Lovrić Š, Žunec S, Lucić Vrdoljak A. Anodic behaviour of some bispyridinium oximes on a glassy-carbon electrode. Int J Electrochem Sci 2013;8:9818-34.
55. Kovačić P. Mechanism of organophosphates (nerve gases and pesticides) and antidotes: electron transfer and oxidative stress. Curr Med Chem 2003;10:2705.
56. Worek F, Bäcker M, Thiermann H, Szinicz L, Mast U, Klimmek R et al. Reappraisal of indications and limitations of oxime therapy in organophosphate poisoning. Hum Exp Toxicol 1997;16:466-72.
57. Eyer P. The role of oximes in the management of organophosphorus pesticide poisoning. Toxicol Rev 2003;22:165-90.
58. Eddleston M, Buckley NA, Checketts H, Senarathna L, Mohamed F, Sheriff MHR et al. Speed of initial atropinisation in significant organophosphorus pesticide poisoning - a systematic comparison of recommended regimens. J Toxicol Clin Toxicol 2004;42:852-62.
59. Svobodova H, Jost P, Stetina R. Comparison of potential cytotoxicity and genotoxicity of selected antidotes against organophosphates inhibiting acetylcholinesterase. Mil Med Sci Lett (Voj Zdrav Listy) 2011;80:142-9.
60. Radić B, Lucić Vrdoljak A, Želježić D, Fuchs N, Berend S, Kopjar N. Evaluation of HI-6 oxime: potential use in protection of human acetylcholinesterase inhibited by antineoplastic drug irinotecan and its cyto/genotoxicity in vitro. Acta Biochim Polon 2007;54:583-93.
61. Lovrić J, Berend S, Lucić Vrdoljak A, Radić B, Katalinić M, Kovarik Z et al. A conjugate of pyridine-4-aldoxime and atropine as a potential antidote against organophosphorus compounds poisoning. Acta Biochim Pol 2011;58:193-8.
62. Tice RR, Agurell E, Anderson D, Burlinson B, Hartmann A, Kobayashi H et al. Single cell gel/comet assay: guidelines for in vitro and in vivo genetic toxicology testing. Environ Mol Mutagen 2000;35:206-21.
63. Wong VWC, Szeto YT, Collins AR, Benzie IFF. The comet assay: a biomonitoring tool for nutraceutical research. Curr Top Nutraceutical Res 2005;3:1-14.
64. Dawson RM. Review of oximes available for the treatment of nerve agent poisoning. J Appl Toxicol 1994;14:317-31.
65. Lucić Vrdoljak A, Berend S, Želježić D, Piljac-Žegarac J, Pleština S, Kuča K et al. Irinotecan side effects relieved by the use of HI-6 oxime: in vivo experimental approach. Basic Clin Pharmacol Toxicol 2009;105:401-9.