The preparation, in vitro screening and molecular docking of symmetrical bisquaternary cholinesterase inhibitors containing a but-(2E)-en-1,4-diyl connecting linkage

References

• Marlatt MW, Webber KM, Moreira PI, Lee HG, Casadesus G, Honda K, Zhu XW, Perry G, Smith MA. Therapeutic opportunities in Alzheimer disease: One for all or all for one? Curr Med Chem 2005;12:1137–1147.
   PubMed Web of Science ®Google Scholar
• Garcia-Carrasco M, Escarcega RO, Fuentes-Alexandro S, Riebeling C, Cervera R. Therapeutic options in autoimmune myasthenia gravis. Autoimmun Rev 2007;6:373–378.
   PubMed Web of Science ®Google Scholar
• Patocka J, Kuca K, Jun D. Acetylcholinesterase and butyrylcholinesterase–important enzymes of human body. Acta Medica 2004;47:215–228.
   Google Scholar
• Marrs TC. Organophosphate poisoning. Pharmacol Therap 1993;58:51–66.
   PubMed Web of Science ®Google Scholar
• Bajgar J. Organophosphates/nerve agent poisoning: mechanism of action, diagnosis, prophylaxis, and treatment. Adv Clin Chem 2004;38:151–216.
   PubMed Web of Science ®Google Scholar
• Doctor BP, Raveh L, Wolfe AD, Maxwell DM, Ashani Y. Enzymes as pretreatment drugs for organophosphate toxicity. Neurosci Biobehav Rev 1991;15:123–128.
   PubMed Web of Science ®Google Scholar
• Bajgar J, Fusek J, Kassa J, Kuca K, Jun D. Chemical aspects of pharmacological prophylaxis against nerve agent poisoning. Curr Med Chem 2009;16:2977–2986.
   PubMed Web of Science ®Google Scholar
• Sultatos LG. Interactions of organophosphorus and carbamate compounds with cholinesterases, In: Gupta RC, ed. Toxicology of Organophosphate and Carbamate Compounds. London: Elsevier Academic Press; 2006:209–218.
   Google Scholar
• Beck KD, Zhu G, Beldowicz D, Brennan FX, Ottenweller JE, Moldow RL, Servatius RJ. Central nervous system effects from a peripherally acting cholinesterase inhibiting agent: interaction with stress or genetics. Ann N Y Acad Sci 2001;933:310–314.
   PubMed Web of Science ®Google Scholar
• Peden-Adams MM, Dudley AC, EuDaly JG, Allen TC, Gilkeson GS, Keil DE. Pyridostigmine bromide (PYR) alters immune function in B6C3F1 mice. Immunopharm Immunot 2004;26:1–15.
   PubMed Web of Science ®Google Scholar
• Bajgar J. Complex view on poisoning with nerve agents and organophosWphates. Acta Medica 2005;48:3–21.
   Google Scholar
• Soukup O, Tobin G, Kumar UK, Binder J, Proska J, Jun D, Fusek J, Kuca K. Interaction of nerve agent antidotes with cholinergic systems. Curr Med Chem 2010;17:1708–1718.
   PubMed Web of Science ®Google Scholar
• Musilek K, Kuca K, Jun D, Dohnal V, Dolezal M. Synthesis of the novel series of bispyridinium compounds bearing (E)-but-2-ene linker and evaluation of their reactivation activity against chlorpyrifos-inhibited acetylcholinesterase. Bioorg Med Chem Lett 2006;16:622–627.
   PubMed Web of Science ®Google Scholar
• Musilek K, Jun D, Cabal J, Kassa J, Gunn-Moore F, Kuca K. Design of a potent reactivator of tabun-inhibited acetyleholinesterase-synthesis and evaluation of (E)-1-(4-carbamoylpyridinium)-4-(4-hydroxyiminomethylpyridinium)-but-2-ene dibromide (K203). J Med Chem 2007;50:5514–5518.
   PubMed Web of Science ®Google Scholar
• Musilek K, Holas O, Kuca K, Jun D, Dohnal V, Opletalova V, Dolezal M. Synthesis of monooxime-monocarbamoyl bispyridinium compounds bearing (E)-but-2-ene linker and evaluation of their reactivation activity against tabun- and paraoxon-inhibited acetylcholinesterase. J Enzyme Inhib Med Chem 2008;23:70–76.
   PubMed Web of Science ®Google Scholar
• Musilek K, Holas O, Jun D, Dohnal V, Gunn-Moore F, Opletalova V, Dolezal M, Kuca K. Monooxime reactivators of acetylcholinesterase with (E)-but-2-ene linker - Preparation and reactivation of tabun- and paraoxon-inhibited acetylcholinesterase. Bioorg Med Chem 2007;15:6733–6741.
   PubMed Web of Science ®Google Scholar
• Sussman JL, Harel M, Frolow F, Oefner C, Goldman A, Toker L, Silman I. Atomic-structure of acetylcholinesterase from Torpedo-californica -A prototypic acetylcholine-binding protein. Science 1991;253:872–879.
   PubMed Web of Science ®Google Scholar
• Musilek K, Komloova M, Zavadova V, Holas O, Hrabinova M, Pohanka M, Dohnal V, Nachon F, Dolezal M, Kuca K, Jung Y-S. Preparation and in vitro screening of symmetrical bispyridinium cholinesterase inhibitors bearing different connecting linkage – initial study for Myasthenia gravis implications. Bioorg Med Chem Lett 2010;20:1763–1766.
   PubMed Web of Science ®Google Scholar
• Musilek K, Holas O, Kuca K, Jun D, Dohnal V, Dolezal M. 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. J Enzyme Inhib Med Chem 2007;22:425–432.
   PubMed Web of Science ®Google Scholar
• Kuca K, Cabal J, Musilek K, Jun D, Bajgar J. Effective bisquaternary reactivators of tabun-inhibited AChE. J Appl Toxicol 2005;25:491–495.
   PubMed Web of Science ®Google Scholar
• Pohanka M, Jun D, Kuca K. Improvement of acetylcholinesterase-based assay for organophosphates in way of identification by reactivators. Talanta 2008;77:451–454.
   PubMed Web of Science ®Google Scholar
• Pohanka M, Hrabinova M., Kuca K. Diagnosis of intoxication by the organophosphate VX: Comparison between an electrochemical sensor and Ellman’s photometric method. Sensors 2008;8:5229–5237.
   PubMed Web of Science ®Google Scholar
• Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK, Olson AJ. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J Comput Chem 1998;19:1639–1662.
   Web of Science ®Google Scholar
• Pettersen EF, Goddard TD, Huang CC, Couch GS, Greenblatt DM, Meng EC, Ferrin TE. UCSF chimera - A visualization system for exploratory research and analysis. J Comput Chem 2004;25:1605–1612.
   PubMed Web of Science ®Google Scholar
• DeLano WL. The PyMOL Molecular Graphics System (2002) on the World Wide Web http://www.pymol.org
   Google Scholar
• Masson P, Carletti E, Nachon F. Structure, activities and biomedical applications of human butyrylcholinesterase. Prot Pept Lett 2009;16:1215–1224.
   PubMed Web of Science ®Google Scholar
• Petroianu GA, Arafat K, Kuca K, Kassa J. Five oximes (K-27, K-33, K-48, BI-6 and methoxime) in comparison with pralidoxime: in vitro reactivation of red blood cell acetylcholinesterase inhibited by paraoxon. J Appl Toxicol 2006;26:64–71.
   PubMed Web of Science ®Google Scholar
• Lorke DE, Hasan MY, Arafat K, Kuca K, Musilek K, Schmitt A, Petroianu GA. In vitro oxime protection of human red blood cell acetylcholinesterase inhibited by diisopropyl-fluorophosphate. J Appl Toxicol 2008;28:422–9.
   PubMed Web of Science ®Google Scholar
• Leonetti F, Catto M, Nicolotti O, Pisani L, Cappa A, Stefanachi A, Carotti A. Homo- and hetero-bivalent edrophonium-like ammonium salts as highly potent, dual binding site AChE inhibitors. Bioorg Med Chem 2008;16:7450–7456.
   PubMed Web of Science ®Google Scholar
• www.pdb.org
   Google Scholar
• Johnson G, Moore SW. The peripheral anionic site of acetylcholinesterase: structure, functions and potential role in rational drug design. Curr Pharm Des 2006;12:217–225.
   PubMed Web of Science ®Google Scholar
• Kuca K, Jun D, Musilek K. Structural requirements of acetylcholinesterase reactivators. Mini Rev Med Chem 2006;6:269–277.
   PubMed Web of Science ®Google Scholar
• Ma JC, Dougherty DA. The cation-pi interaction. Chem Rev 1997; 97:1303–1324.
   PubMed Web of Science ®Google Scholar
• Wiesner J, Kriz Z, Kuca K, Jun, D, Koca J. Why acetylcholinesterase reactivators do not work in butyrylcholinesterase. J Enzyme Inhib Med Chem 2010;25:318–322.
   PubMed Web of Science ®Google Scholar