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Research Article

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

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Pages 425-432 | Received 16 Oct 2006, Accepted 21 Nov 2006, Published online: 04 Oct 2008

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Read on this site (10)

Jiri Kassa, Jan Misik, Jana Hatlapatkova & Jana Zdarova Karasova. (2017) A comparison of neuroprotective efficacy of two novel reactivators of acetylcholinesterase called K920 and K923 with the oxime K203 and trimedoxime in tabun-poisoned rats. Toxicology Mechanisms and Methods 27:3, pages 236-243.
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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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Jiri Kassa, Vendula Sepsova, Martina Tumova, Kamil Musilek & Anna Horova. (2014) The evaluation of the reactivating and therapeutic efficacy of two novel oximes (K361 and K378) in comparison with the oxime K203 and trimedoxime in tabun-poisoned rats and mice. Toxicology Mechanisms and Methods 24:3, pages 173-178.
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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, 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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Kamil Kuca, Gupta RC, Kamil Musilek, Daniel Jun & Miroslav Pohanka. (2009) In vitro identification of novel acetylcholinesterase reactivators. Toxin Reviews 28:4, pages 238-244.
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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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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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Jiri Kassa, Jana Karasova, Jiri Bajgar, Kamil Kuca & Kamil Musilek. (2008) A comparison of the therapeutic and reactivating efficacy of newly developed bispyridinium compounds (K206, K269) with currently available oximes against tabun in rats and mice. Journal of Enzyme Inhibition and Medicinal Chemistry 23:6, pages 776-780.
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Cecilia Lindgren, Nina Forsgren, Norman Hoster, Christine Akfur, Elisabet Artursson, Lotta Edvinsson, Richard Svensson, Franz Worek, Fredrik Ekström & Anna Linusson. (2022) Broad‐Spectrum Antidote Discovery by Untangling the Reactivation Mechanism of Nerve‐Agent‐Inhibited Acetylcholinesterase. Chemistry – A European Journal 28:40.
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Sandip B. Bharate, Chih-Kai Chao & Charles M. Thompson. (2019) Comparison of the reactivation rates of acetylcholinesterase modified by structurally different organophosphates using novel pyridinium oximes. Environmental Toxicology and Pharmacology 71, pages 103218.
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Dietrich E. Lorke & Georg A. Petroianu. (2019) Treatment of Organophosphate Poisoning with Experimental Oximes: A Review. Current Organic Chemistry 23:5, pages 628-639.
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Dietrich E. Lorke & Georg A. Petroianu. (2019) The Experimental Oxime K027—A Promising Protector From Organophosphate Pesticide Poisoning. A Review Comparing K027, K048, Pralidoxime, and Obidoxime. Frontiers in Neuroscience 13.
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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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K. Kuca, J. Korabecny, R. Dolezal, E. Nepovimova, O. Soukup, L. Gorecki & K. Musilek. (2017) Tetroxime: reactivation potency – in vitro and in silico study. RSC Advances 7:12, pages 7041-7045.
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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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Jiri Kassa, Vendula Sepsova, Anna Horova & Kamil Musilek. (2015) A comparison of the reactivating and therapeutic efficacy of two novel bispyridinium oximes (K920, K923) with the oxime K203 and trimedoxime in tabun-poisoned rats and mice. Journal of Applied Biomedicine 13:4, pages 299-304.
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Namrata Singh, Ondřej Soukup, Rafael Doležal, Zdeněk Fišar, Bhanushree Gupta, Kallol K. Ghosh & Kamil Kuča. (2015) ACID DISSOCIATION CONSTANTS AND MOLECULAR DESCRIPTORS OF SOME XYLENE LINKED BISPYRIDINIUM OXIMES. Military Medical Science Letters 84:3, pages 94-103.
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Jiri Kassa, Vendula Sepsova, Martina Tumova, Anna Horova & Kamil Musilek. (2015) A Comparison of the Reactivating and Therapeutic Efficacy of Two Newly Developed Oximes (K727 and K733) with Oxime K203 and Trimedoxime in Tabun-Poisoned Rats and Mice. Basic & Clinical Pharmacology & Toxicology 116:4, pages 367-371.
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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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Jiri Kassa, Jan Misik & Jana Zdarova Karasova. (2015) Neuroprotective efficacy of newly developed oximes in comparison with currently available oximes in tabun-poisoned rats. Journal of Applied Biomedicine 13:1, pages 39-46.
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Jiří Kassa, Jana Hatlapatková & Jana Žďárová Karasová. (2015) The Evaluation of the Potency of Newly Developed Oximes (K727, K733) and Trimedoxime to Counteract Acute Neurotoxic Effects of Tabun in Rats. Acta Medica (Hradec Kralove, Czech Republic) 58:4, pages 135-143.
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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 .
Jiri Kassa, Vendula Sepsova & Martina Tumova. (2014) A comparison of the reactivating and therapeutic efficacy of two novel oximes K378 and K458 with currently available oximes in rats and mice poisoned with sarin. Journal of Applied Biomedicine 12:3, pages 155-160.
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Jyotiranjan Acharya, Hemlata Rana & M.P. Kaushik. (2011) Synthesis and in vitro evaluation of xylene linked carbamoyl bis-pyridinium monooximes as reactivators of organophosphorus (OP) inhibited electric eel acetylcholinesterase (AChE). European Journal of Medicinal Chemistry 46:9, pages 3926-3933.
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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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Kamil Kuča, Kamil Musílek, Jana Karasová, Daniel Jun, Ondřej Soukup, Miroslav Pohanka, Kallol Kumar Ghosh & Martina Hrabinová. (2011) ON THE UNIVERSALITY OF OXIME HLö-7 - ANTIDOTE FOR CASE OF THE NERVE AGENT POISONING. Military Medical Science Letters 80:2, pages 80-84.
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Kamil Musilek, Jan Roder, Marketa Komloova, Ondrej Holas, Martina Hrabinova, Miroslav Pohanka, Vlastimil Dohnal, Veronika Opletalova, Kamil Kuca & Young-Sik Jung. (2011) Preparation, in vitro screening and molecular modelling of symmetrical 4-tert-butylpyridinium cholinesterase inhibitors—Analogues of SAD-128. Bioorganic & Medicinal Chemistry Letters 21:1, pages 150-154.
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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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Ondrej Holas, Kamil Musilek, Miroslav Pohanka, Kamil Kuca, Veronika Opletalova & Young-Sik Jung. (2010) In vitro Screening of Oxime Reactivators on the Model of Paraoxon-inhibited Acetylcholinesterase-SAR Study. Bulletin of the Korean Chemical Society 31:6, pages 1609-1614.
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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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Sandip B. Bharate, Lilu Guo, Tony E. Reeves, Douglas M. Cerasoli & Charles M. Thompson. (2010) Bisquaternary pyridinium oximes: Comparison of in vitro reactivation potency of compounds bearing aliphatic linkers and heteroaromatic linkers for paraoxon-inhibited electric eel and recombinant human acetylcholinesterase. Bioorganic & Medicinal Chemistry 18:2, pages 787-794.
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Kamil Kuca, Kamil Musilek, Miroslav Pohanka, Vlastimil Dohnal & Jiri Patocka. (2009) REACTIVATION POTENCY OF THE ACETYLCHOLINESTERASE REACTIVATOR OBIDOXIME IS LIMITED. Biomedical Papers 153:4, pages 259-262.
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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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D. E. Lorke & G. A. Petroianu. (2009) Minireview: does in‐vitro testing of oximes help predict their in‐vivo action after paraoxon exposure? . Journal of Applied Toxicology 29:6, pages 459-469.
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S. M. Nurulain, D. E. Lorke, M. Y. Hasan, M. Shafiullah, K. Kuča, K. Musilek & G. A. Petroianu. (2009) Efficacy of Eight Experimental Bispyridinium Oximes Against Paraoxon-Induced Mortality: Comparison with the Conventional Oximes Pralidoxime and Obidoxime. Neurotoxicity Research 16:1, pages 60-67.
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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 .
D. E. Lorke, S. M. Nurulain, M. Y. Hasan, K. Kuča, K. Musilek & G. A. Petroianu. (2008) Eight new bispyridinium oximes in comparison with the conventional oximes pralidoxime and obidoxime: in vivo efficacy to protect from diisopropylfluorophosphate toxicity . Journal of Applied Toxicology 28:7, pages 920-928.
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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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Jiri Kassa, Jana Karasova, Kamil Musilek & Kamil Kuca. (2008) An evaluation of therapeutic and reactivating effects of newly developed oximes (K156, K203) and commonly used oximes (obidoxime, trimedoxime, HI-6) in tabun-poisoned rats and mice. Toxicology 243:3, pages 311-316.
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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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