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Research Article

Synthesis of a novel series of bispyridinium compounds bearing a xylene linker and evaluation of their reactivation activity against chlorpyrifos-inhibited acetylcholinesterase

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Pages 409-415 | Received 27 Mar 2005, Accepted 21 Apr 2005, Published online: 04 Oct 2008

Keep up to date with the latest research on this topic with citation updates for this article.

Read on this site (10)

Jiri Kassa, Jana Zdarova Karasova, Kamil Kuca & Kamil Musilek. (2010) A comparison of the reactivating and therapeutic efficacy of newly developed oximes (K347, K628) with commonly used oximes (obidoxime, HI-6) against tabun in rats and mice. Drug and Chemical Toxicology 33:3, pages 227-232.
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Lucie Musilova, Kamil Kuca, Young-Sik jung & Daniel Jun. (2009) In vitro oxime-assisted reactivation of paraoxon-inhibited human acetylcholinesterase and butyrylcholinesterase. Clinical Toxicology 47:6, pages 545-550.
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Miroslav Pohanka, Daniel Jun & Kamil Kuca. (2008) Photometric microplate assay for estimation of the efficacy of paraoxon-inhibited acetylcholinesterase reactivation. Journal of Enzyme Inhibition and Medicinal Chemistry 23:6, pages 781-784.
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Danijela Z. Krstić, Mirjana Čolović, Mojca Bavcon kralj, Mladen Franko, Katarina Krinulović, Polonca Trebše & VESNA VASIĆ. (2008) Inhibition of AChE by malathion and some structurally similar compounds. Journal of Enzyme Inhibition and Medicinal Chemistry 23:4, pages 562-573.
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Kamil Musilek, Ondrej Holas, Kamil Kuca, Daniel Jun, Vlastimil Dohnal, Veronika Opletalova & Martin Dolezal. (2008) Synthesis of monooxime-monocarbamoyl bispyridinium compounds bearing (E)-but-2-ene linker and evaluation of their reactivation activity against tabun- and paraoxon-inhibited acetylcholinesterase. Journal of Enzyme Inhibition and Medicinal Chemistry 23:1, pages 70-76.
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Kamil Kuca, Jiri Cabal, Daniel Jun & Martina Hrabinova. (2007) Potency of Five Structurally Different Acetylcholinesterase Reactivators to Reactivate Human Brain Cholinesterases Inhibited by Cyclosarin. Clinical Toxicology 45:5, pages 512-515.
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Kamil Musilek, Ondrej Holas, Kamil Kuca, Daniel Jun, Vlastimil Dohnal & Martin Dolezal. (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. Journal of Enzyme Inhibition and Medicinal Chemistry 22:4, pages 425-432.
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Kamil Kuca, Jiri Cabal, Daniel Jun, Jiri Bajgar & Martina Hrabinova. (2006) Potency of new structurally different oximes to reactivate cyclosarin-inhibited human brain acetylcholinesterases. Journal of Enzyme Inhibition and Medicinal Chemistry 21:6, pages 663-666.
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Martina Hrabinova, Kamil Musilek, Daniel Jun & Kamil Kuca. (2006) New group of xylene linker-containing acetylcholinesterase reactivators as antidotes against the nerve agent cyclosarin. Journal of Enzyme Inhibition and Medicinal Chemistry 21:5, pages 515-519.
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Articles from other publishers (37)

Ashima Thakur, Jayant Patwa, Abha Sharma & Swaran Jeet Singh Flora. (2022) Synthesis, Molecular Docking, BSA, and In Vitro Reactivation Study of Imidazopyridine Oximes Against Paraoxon Inhibited Acetylcholinesterase. Medicinal Chemistry 18:2, pages 273-287.
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Miloš P. Stojiljković, Milan Jokanović, Dragana Lončar-Stojiljković & Ranko Škrbić. 2020. Handbook of Toxicology of Chemical Warfare Agents. Handbook of Toxicology of Chemical Warfare Agents 1103 1119 .
Shibaji Ghosh, Nellore Bhanu Chandar, Kalyanashis Jana & Bishwajit Ganguly. (2017) Revealing the importance of linkers in K-series oxime reactivators for tabun-inhibited AChE using quantum chemical, docking and SMD studies. Journal of Computer-Aided Molecular Design 31:8, pages 729-742.
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Lukas Gorecki, Jan Korabecny, Kamil Musilek, David Malinak, Eugenie Nepovimova, Rafael Dolezal, Daniel Jun, Ondrej Soukup & Kamil Kuca. (2016) SAR study to find optimal cholinesterase reactivator against organophosphorous nerve agents and pesticides. Archives of Toxicology 90:12, pages 2831-2859.
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Michael Winter, Timo Wille, Kamil Musilek, Kamil Kuca, Horst Thiermann & Franz Worek. (2016) Investigation of the reactivation kinetics of a large series of bispyridinium oximes with organophosphate-inhibited human acetylcholinesterase. Toxicology Letters 244, pages 136-142.
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J. Janockova, E. Zilecka, J. Kasparkova, V. Brabec, O. Soukup, K. Kuca & M. Kozurkova. (2016) Assessment of DNA-binding affinity of cholinesterase reactivators and electrophoretic determination of their effect on topoisomerase I and II activity. Molecular BioSystems 12:9, pages 2910-2920.
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Gabriele Horn, Timo Wille, Kamil Musilek, Kamil Kuca, Horst Thiermann & Franz Worek. (2014) Reactivation kinetics of 31 structurally different bispyridinium oximes with organophosphate-inhibited human butyrylcholinesterase. Archives of Toxicology 89:3, pages 405-414.
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Kamil Musilek, Jan Korabecny, Daniel Jun, Jiri Kassa & Kamil Kuca. 2015. Handbook of Toxicology of Chemical Warfare Agents. Handbook of Toxicology of Chemical Warfare Agents 1071 1087 .
Christina M. Wilhelm, Thomas H. Snider, Michael C. Babin, David A. Jett, Gennady E. PlatoffJr.Jr. & David T. Yeung. (2014) A comprehensive evaluation of the efficacy of leading oxime therapies in guinea pigs exposed to organophosphorus chemical warfare agents or pesticides. Toxicology and Applied Pharmacology 281:3, pages 254-265.
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Konstantis F. Konidaris, Georgios A. Dalkas, Eugenia Katsoulakou, George Pairas, Catherine P. Raptopoulou, Fotini N. Lamari, Georgios A. Spyroulias & Evy Manessi-Zoupa. (2014) ZnII/pyridyloxime complexes as potential reactivators of OP-inhibited acetylcholinesterase: In vitro and docking simulation studies. Journal of Inorganic Biochemistry 134, pages 12-19.
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Nadezhda Shchepina, Viktor Avrorin, Gennadii Badun, Galina Alexandrova, Irina Agafonova & Nina Popova. (2014) Quinolinium Structure as Labeled Biomarkers. Open Journal of Synthesis Theory and Applications 03:03, pages 21-26.
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Jana Janockova, Zuzana Gulasova, Kamil Musilek, Kamil Kuca & Maria Kozurkova. (2013) Novel cholinesterase modulators and their ability to interact with DNA. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 115, pages 364-369.
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Kamil Musilek, Martin Dolezal, Frank Gunn‐Moore & Kamil Kuca. (2011) Design, evaluation and structure—Activity relationship studies of the AChE reactivators against organophosphorus pesticides. Medicinal Research Reviews 31:4, pages 548-575.
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Daniel Jun, Lucie Musilova, Kamil Musilek & Kamil Kuca. (2011) In Vitro Ability of Currently Available Oximes to Reactivate Organophosphate Pesticide-Inhibited Human Acetylcholinesterase and Butyrylcholinesterase. International Journal of Molecular Sciences 12:3, pages 2077-2087.
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Kamil Musilek, Marketa Komloova, Ondrej Holas, Anna Horova, Miroslav Pohanka, Frank Gunn-Moore, Vlastimil Dohnal, Martin Dolezal & Kamil Kuca. (2011) Mono-oxime bisquaternary acetylcholinesterase reactivators with prop-1,3-diyl linkage—Preparation, in vitro screening and molecular docking. Bioorganic & Medicinal Chemistry 19:2, pages 754-762.
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O. Soukup, Z. Kristofikova, J. Proska, G. Tobin, J. Patocka, J. Marek, D. Jun, J. Fusek, D. Ripova & K. Kuca. (2010) Novel acetylcholinesterase reactivator K112 and its cholinergic properties. Biomedicine & Pharmacotherapy 64:8, pages 541-545.
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Kamil Kuca, Jiri Cabal, Daniel Jun, Kamil Musilek, Ondrej Soukup, Miroslav Pohanka, Jaroslav Pejchal, Kyung-Ae Oh, Garp Yeol Yang & Young-Sik Jung. (2010) Reactivation of VX-inhibited AChE by novel oximes having two oxygen atoms in the linker. Environmental Toxicology and Pharmacology 30:1, pages 85-87.
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Agnieszka Skórska-Stania, Magdalena Śliwa, Kamil Musilek, Kamil Kuca, Josef Jampilek, Robert Musiol, Barbara J. Oleksyn & Jiri Dohnal. (2010) Selected AChE reactivators in different crystalline environment: salts and enzyme. Structural Chemistry 21:3, pages 495-501.
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Kamil Musilek, Marketa Komloova, Vlasta Zavadova, Ondrej Holas, Martina Hrabinova, Miroslav Pohanka, Vlastimil Dohnal, Florian Nachon, Martin Dolezal, Kamil Kuca & Young-Sik Jung. (2010) Preparation and in vitro screening of symmetrical bispyridinium cholinesterase inhibitors bearing different connecting linkage—initial study for Myasthenia gravis implications. Bioorganic & Medicinal Chemistry Letters 20:5, pages 1763-1766.
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Kamil Musilek, Ondrej Holas, Jan Misik, Miroslav Pohanka, Ladislav Novotny, Vlastimil Dohnal, Veronika Opletalova & Kamil Kuca. (2010) Monooxime-monocarbamoyl Bispyridinium Xylene-Linked Reactivators of Acetylcholinesterase-Synthesis, In vitro and Toxicity Evaluation, and Docking Studies. ChemMedChem 5:2, pages 247-254.
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Jiří Bajgar. (2010) Optimal Choice of Acetylcholinesterase Reactivators for Antidoral Treatment of Nerve Agent Intoxication. Acta Medica (Hradec Kralove, Czech Republic) 53:4, pages 207-211.
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Kamil Kuca, Jiri Cabal, Yung Sik Jung, Kamil Musilek, Ondrej Soukup, Daniel Jun, Miroslav Pohanka, Lucie Musilova, Jana Karasová, Ladislav Novotný & Martina Hrabinova. (2009) Reactivation of Human Brain Homogenate Cholinesterases Inhibited by Tabun using Newly Developed Oximes K117 and K127. Basic & Clinical Pharmacology & Toxicology 105:3, pages 207-210.
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Kamil Kuca, Kamil Musilek, Daniel Jun, Jiri Bajgar & Jiri Kassa. 2009. Handbook of Toxicology of Chemical Warfare Agents. Handbook of Toxicology of Chemical Warfare Agents 997 1021 .
Kamil Musilek, Jiri Kucera, Daniel Jun, Vlastimil Dohnal, Veronika Opletalova & Kamil Kuca. (2008) Monoquaternary pyridinium salts with modified side chain—synthesis and evaluation on model of tabun- and paraoxon-inhibited acetylcholinesterase. Bioorganic & Medicinal Chemistry 16:17, pages 8218-8223.
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D. E. Lorke, M. Y. Hasan, K. Arafat, K. Kuča, K. Musilek, A. Schmitt & G. A. Petroianu. (2008) In vitro oxime protection of human red blood cell acetylcholinesterase inhibited by diisopropyl‐fluorophosphate . Journal of Applied Toxicology 28:4, pages 422-429.
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Kamil Musilek, Daniel Jun, Jiri Cabal, Jiri Kassa, Frank Gunn-Moore & Kamil Kuca. (2007) Design of a Potent Reactivator of Tabun-Inhibited AcetylcholinesteraseSynthesis and Evaluation of ( E )-1-(4-Carbamoylpyridinium)-4-(4-hydroxyiminomethylpyridinium)-but-2-ene Dibromide (K203) . Journal of Medicinal Chemistry 50:22, pages 5514-5518.
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Kamil Musilek, Ondrej Holas, Daniel Jun, Vlastimil Dohnal, Frank Gunn-Moore, Veronika Opletalova, Martin Dolezal & Kamil Kuca. (2007) Monooxime reactivators of acetylcholinesterase with (E)-but-2-ene linker—Preparation and reactivation of tabun- and paraoxon-inhibited acetylcholinesterase. Bioorganic & Medicinal Chemistry 15:21, pages 6733-6741.
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Kamil Kuca, Kamil Musilek, Martin Paar, Daniel Jun, Petr Stodulka, Martina Hrabinova & Jan Marek. (2007) Targeted Synthesis of 1-(4-Hydroxyiminomethylpyridinium)-3-pyridiniumpropane Dibromide – A New Nerve Agent Reactivator. Molecules 12:8, pages 1964-1972.
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Kamil Musilek, Ondrej Holas, Kamil Kuca, Daniel Jun, Vlastimil Dohnal, Veronika Opletalova & Martin Dolezal. (2007) 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. Bioorganic & Medicinal Chemistry Letters 17:11, pages 3172-3176.
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Kamil Kuca, Jiri Cabal, Daniel Jun & Kamil Musilek. (2007) In vitro reactivation potency of acetylcholinesterase reactivators — K074 and K075 — to reactivate tabun-inhibited human brain cholinesterases. Neurotoxicity Research 11:2, pages 101-106.
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Kamil Musílek, Kamil Kuča, Daniel Jun & Martin Doležal. (2007) In vitro reactivation potency of bispyridinium (E)-but-2-ene linked acetylcholinesterase reactivators against tabun-inhibited acetylcholinesterase. Journal of Applied Biomedicine 5:1, pages 25-30.
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K. Kuča, V. Račáková & D. Jun. (2007) Structure—activity relationships for in vitro oxime reactivation of chlorpyrifos-inhibited acetylcholinesterase. Chemical Papers 61:4.
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Kamil Musílek, Kamil Kuča & Daniel Jun. (2007) Evaluation of Potency of Known Oximes (Pralidoxime, Trimedoxime, HI-6, Methoxime, Obidoxime) to in vitro Reactivate Acetylcholinesterase Inhibited by Pesticides (Chlorpyrifos and Methylchlorpyrifos and Nerve Agent (Russian VX). Acta Medica (Hradec Kralove, Czech Republic) 50:3, pages 203-206.
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Kamil Musilek, Ondrej Holas, Kamil Kuca, Daniel Jun, Vlastimil Dohnal & Martin Dolezal. (2006) Synthesis of asymmetrical bispyridinium compounds bearing cyano-moiety and evaluation of their reactivation activity against tabun and paraoxon-inhibited acetylcholinesterase. Bioorganic & Medicinal Chemistry Letters 16:21, pages 5673-5676.
Crossref
. (2006) Potency of Several Structurally Different Acetylcholinesterase Reactivators to Reactivate House Fly and Bovine Acetylcholinesterases Inhibited by Paraoxon and DFP. Bulletin of the Korean Chemical Society 27:9, pages 1401-1404.
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Kyung-Ae Oh, Garp Yeol Yang, Daniel Jun, Kamil Kuca & Young-Sik Jung. (2006) Bis-pyridiumaldoxime reactivators connected with CH2O(CH2) OCH2 linkers between pyridinium rings and their reactivity against VX. Bioorganic & Medicinal Chemistry Letters 16:18, pages 4852-4855.
Crossref
Veronika Račáková, Daniel Jun, Veronika Opletalová & Kamil Kuča. (2006) Reactivation of acetycholinesterase inhibited by the pesticide chlorpyrifos. Journal of Applied Biomedicine 4:3, pages 147-151.
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