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Research Article

Synthesis of monooxime-monocarbamoyl bispyridinium compounds bearing (E)-but-2-ene linker and evaluation of their reactivation activity against tabun- and paraoxon-inhibited acetylcholinesterase

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Pages 70-76 | Received 22 Dec 2006, Accepted 15 Feb 2007, Published online: 04 Oct 2008

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Arvind Kumar Sahu, Rahul Sharma, Bhanushree Gupta, Kamil Musilek, Kamil Kuca, Jyotiranjan Acharya & Kallol K. Ghosh. (2016) Oxime-mediated in vitro reactivation kinetic analysis of organophosphates-inhibited human and electric eel acetylcholinesterase. Toxicology Mechanisms and Methods 26:5, pages 319-326.
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Juliana O.S. Giacoppo, Tanos C.C. França, Kamil Kuča, Elaine F.F. da Cunha, Ruben Abagyan, Daiana T. Mancini & Teodorico C. Ramalho. (2015) Molecular modeling and in vitro reactivation study between the oxime BI-6 and acetylcholinesterase inhibited by different nerve agents. Journal of Biomolecular Structure and Dynamics 33:9, pages 2048-2058.
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Jiri Kassa, Jana Zdarova Karasova & Vendula Sepsova. (2013) A comparison of the reactivating efficacy of a novel bispyridinium oxime K203 with currently available oximes in VX agent-poisoned rats. Journal of Enzyme Inhibition and Medicinal Chemistry 28:4, pages 753-757.
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Jiri Kassa, Jana Zdarova Karasova & Sandra Tesarova. (2011) A comparison of the neuroprotective efficacy of individual oxime (HI-6) and combinations of oximes (HI-6+trimedoxime, HI-6+K203) in soman-poisoned rats. Drug and Chemical Toxicology 34:3, pages 233-239.
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Kamil Musilek, Ruzena Pavlikova, Jan Marek, Marketa Komloova, Ondrej Holas, Martina Hrabinova, Miroslav Pohanka, Vlastimil Dohnal, Martin Dolezal, Frank Gunn-Moore & Kamil Kuca. (2011) The preparation, in vitro screening and molecular docking of symmetrical bisquaternary cholinesterase inhibitors containing a but-(2E)-en-1,4-diyl connecting linkage. Journal of Enzyme Inhibition and Medicinal Chemistry 26:2, pages 245-253.
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Jiri Kassa, Jana Zdarova Karasova, Ruzena Pavlikova, Kamil Musilek, Kamil Kuca, Jiri Bajgar & Young-Sik Jung. (2011) A comparison of reactivating and therapeutic efficacy of bispyridinium acetylcholinesterase reactivator KR-22934 with the oxime K203 and commonly used oximes (obidoxime, trimedoxime, HI-6) in tabun-poisoned rats and mice. Toxicology Mechanisms and Methods 21:3, pages 241-245.
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Jiri Bajgar, Petr Hajek, Jana Karasova Zdarova, Jiri Kassa, Antonin Paseka, Dasa Slizova, Otakar Krs, Kamil Kuca, Daniel Jun, Josef Fusek & Lukas Capek. (2010) A comparison of tabun-inhibited rat brain acetylcholinesterase reactivation by three oximes (HI-6, obidoxime, and K048) in vivo detected by biochemical and histochemical techniques. Journal of Enzyme Inhibition and Medicinal Chemistry 25:6, pages 790-797.
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Jiri Kassa, Jana Zdarova Karasova, Sandra Tesarova, Kamil Kuca & Kamil Musilek. (2010) A comparison of the ability of newly-developed bispyridinium oxime K203 and currently available oximes (trimedoxime, obidoxime, HI-6) to counteract the acute neurotoxicity of soman in rats. Toxicology Mechanisms and Methods 20:8, pages 445-451.
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Kamil Kuca, Kamil Musilek, Daniel Jun, Miroslav Pohanka, Kallol Kumar Ghosh & Martina Hrabinova. (2010) Oxime K027: novel low-toxic candidate for the universal reactivator of nerve agent- and pesticide-inhibited acetylcholinesterase. Journal of Enzyme Inhibition and Medicinal Chemistry 25:4, pages 509-512.
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Jiri Kassa, Jana Zdarova Karasova, Filip Caisberger, Kamil Musilek, Kamil Kuca & Young-Sik Jung. (2010) A comparison of reactivating and therapeutic efficacy of the oxime K203 and its fluorinated analog (KR-22836) with currently available oximes (obidoxime, trimedoxime, HI-6) against tabun in rats and mice. Journal of Enzyme Inhibition and Medicinal Chemistry 25:4, pages 480-484.
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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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Huba Kalász, Emil Mincsovics, Nazila Ram & Kamil Kuca. (2010) THIN-LAYER CHROMATOGRAPHY OF PYRIDINIUM ALDOXIMES USING DISTINCT TECHNIQUES FOR DEVELOPMENT. Journal of Liquid Chromatography & Related Technologies 33:7-8, pages 922-935.
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Jiri Kassa, Jana Zdarova Karasova, Filip Caisberger & Jiri Bajgar. (2009) The influence of combinations of oximes on the reactivating and therapeutic efficacy of antidotal treatment of soman poisoning in rats and mice. Toxicology Mechanisms and Methods 19:9, pages 547-551.
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Jiri Kassa, Jana Karasova, Jiri Bajgar, Kamil Kuca, Kamil Musilek & Irena Kopelikova. (2009) A comparison of the reactivating and therapeutic efficacy of newly developed bispyridinium oximes (K250, K251) with commonly used oximes against tabun in rats and mice. Journal of Enzyme Inhibition and Medicinal Chemistry 24:4, pages 1040-1044.
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Jiri Kassa, Jana Zdarova Karasova, Kamil Musilek & Kamil Kuca. (2009) A comparison of reactivating and therapeutic efficacy of newly-developed oximes (K156, K203) and commonly used oximes (obidoxime, HI-6) in cyclosarin-poisoned rats and mice. Toxicology Mechanisms and Methods 19:5, pages 346-350.
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Miroslav Pohanka, Daniel Jun & Kamil Kuca. (2009) In vitro reactivation of trichlorfon-inhibited butyrylcholinesterase using HI-6, obidoxime, pralidoxime and K048. Journal of Enzyme Inhibition and Medicinal Chemistry 24:3, pages 680-683.
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Jiri Kassa, Jana Karasova, Libor Vasina, Jiri Bajgar, Kamil Kuca & Kamil Musilek. (2009) A Comparison of neuroprotective efficacy of newly developed oximes (K203, K206) and commonly used oximes (obidoxime, HI-6) in tabun-poisoned rats. Drug and Chemical Toxicology 32:2, pages 128-138.
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José Daniel Figueroa-Villar, Elaine C. Petronilho, Kamil Kuca & Tanos C.C. Franca. (2021) Review about Structure and Evaluation of Reactivators of Acetylcholinesterase Inhibited with Neurotoxic Organophosphorus Compounds. Current Medicinal Chemistry 28:7, pages 1422-1442.
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Evica Antonijevic, Kamil Musilek, Kamil Kuca, Danijela Djukic-Cosic, Milena Andjelkovic, Aleksandra Buha Djordjevic & Biljana Antonijevic. (2019) Comparison of oximes K203 and K027 based on Benchmark dose analysis of rat diaphragmal acetylcholinesterase reactivation. Chemico-Biological Interactions 308, pages 385-391.
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Evica Antonijevic, Kamil Musilek, Kamil Kuca, Danijela Djukic-Cosic, Marijana Curcic, Dejana Cupic Miladinovic, Zorica Bulat & Biljana Antonijevic. (2018) Dose-response modeling of reactivating potency of oximes K027 and K203 against a direct acetylcholinesterase inhibitor in rat erythrocytes. Food and Chemical Toxicology 121, pages 224-230.
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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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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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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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Jiří Kassa, Jana Žďárová Karasová & Markéta Krejčiová. (2013) Therapeutic efficacy of a novel bispyridinium oxime K203 and commonly used oximes (HI-6, obidoxime, trimedoxime, methoxime) in soman-poisoned male rats and mice. Journal of Applied Biomedicine 11:1, pages 7-13.
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Jiri Kassa, Jan Misik & Jana Zdarova Karasova. (2012) 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 & Clinical Pharmacology & Toxicology 111:5, pages 333-338.
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Junfeng Dou, Aizhong Ding, Lirong Cheng, Raju Sekar, Hongting Wang & Shuairan Li. (2012) A screen-printed, amperometric biosensor for the determination of organophosphorus pesticides in water samples. Journal of Environmental Sciences 24:5, pages 956-962.
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Jiří Kassa, Jana Zdarová Karasová, Růžena Pavlíková, Filip Caisberger & Jiří Bajgar. (2012) The Ability of Oxime Mixtures to Increase the Reactivating and Therapeutic Efficacy of Antidotal Treatment of Cyclosarin Poisoning in Rats and Mice. Acta Medica (Hradec Kralove, Czech Republic) 55:1, pages 27-31.
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Jiří Kassa, Jana Žďárová Karasová, Vendula Šepsová & Jiří Bajgar. (2011) A comparison of the reactivating and therapeutic efficacy of the newly developed bispyridinium oxime K203 with currently available oximes, in sarin poisoned rats and mice. Journal of Applied Biomedicine 9:4, pages 225-230.
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Sandip B. Bharate, Lilu Guo, Tony E. Reeves, Douglas M. Cerasoli & Charles M. Thompson. (2009) New series of monoquaternary pyridinium oximes: Synthesis and reactivation potency for paraoxon-inhibited electric eel and recombinant human acetylcholinesterase. Bioorganic & Medicinal Chemistry Letters 19:17, pages 5101-5104.
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