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

References

• 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
• Francotte P, Graindorge E, Boverie S, de Tullio P, Pirotte B. New trends in the design of drugs against Alzheimer's disease. Curr Med Chem 2004; 11: 1757–1778
   PubMed Web of Science ®Google Scholar
• Patocka J, Kuca K, Dohnal V, Jun D. Chemical terrorism. Kontakt 2006; 4: 123–127, (in Czech).
   Google Scholar
• Satoh T, Hosokawa M. Organophosphates and their impact on the global environment. Neurotoxicology 2000; 21: 223–227
   PubMed Web of Science ®Google Scholar
• Krivoy A, Layish I, Rotman E, Goldberg A, Yehezkelli Y. OP or not OP: The medical challenge at the chemical terrorism scene. Prehospital Disaster Med 2005; 20: 155–158
   PubMedGoogle Scholar
• Marrs TC. Organophosphate poisoning. Pharmacol Therapeut 1993; 58: 51–66
   PubMed Web of Science ®Google Scholar
• Marklund A, Andersson B, Haglund P. Organophosphorus flame retardants and plasticizers in air from various indoor environments. J Environ Monit 2005; 7: 814–819
   PubMedGoogle Scholar
• Gupta R. In Toxicology of organophosphate & carbamate compounds. Elsevier Academic Press, London 2006; 1: 5–69
   Google Scholar
• Hodgson E, Rose RL. Organophosphorus chemicals: Potent inhibitors of the human metabolism of steroid hormones and xenobiotics. Drug Metab Rev 2006; 38: 149–162
   PubMed Web of Science ®Google Scholar
• Costa LG. Current issues in organophosphate toxicology. Clin Chim Acta 2006; 366: 1–13
   PubMed Web of Science ®Google Scholar
• Saxena A, Fedorko JM, Vinayaka CR, Medhekar R, Radic Z, Taylor P, Lockridge O, Doctor BP. Aromatic amino-acid residues at the active and peripheral anionic sites control the binding of E2020 (Aricept) to cholinesterases. Eur J Biochem 2003; 270: 4447–4458
   PubMedGoogle Scholar
• Rosenberry TL, Johnson JL, Cusack B, Thomas JL, Emani S, Venkatasubban KS. Interactions between the peripheral site and the acylation site in acetylcholinesterase. Chem-Biol Inter 2005; 157–158: 181–189
   PubMed Web of Science ®Google Scholar
• Radic Z, Manetsch R, Krasinski A, Raushel J, Yamauchi J, Garcia C, Kolb H, Sharpless KB, Taylor P. Molecular basis of interactions of cholinesterases with tight binding inhibitors. Chem-Biol Inter 2005; 157–158: 133–141
   PubMed Web of Science ®Google Scholar
• Axelsen PH, Harel M, Silman I, Sussman J. Structure and dynamics of the active site gorge of acetylcholinesterase: Synergistic use of molecular dynamics simulation and X-ray crystallography. Protein Sci 1994; 3: 188–197
   PubMed Web of Science ®Google Scholar
• Ashani Y, Radic Z, Tsilgeny I, Vellom DC, Pickering NA, Quinn DM, Doctor BP, Taylor P. Amino acid residues controlling reactivation of organophosphonyl conjugates of acetylcholinesterase by mono- and bisquaternary oximes. J Biol Chem 1995; 270: 6370–6380
   PubMed Web of Science ®Google Scholar
• Ekstrom F, Akfur C, Tunemalm AK, Lundberg S. Structural changes of phenylalanine 338 and histidine 447 revealed by the crystal structures of tabun-inhibited murine acetylcholinesterase. Biochemistry 2006; 45: 74–81
   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
• Cabal J, Kuca K, Kassa J. Specification of the structure of oximes able to reactivate tabun-inhibited acetylcholinesterase. Basic Clin Pharmacol Toxicol 2004; 95: 81–86
   PubMed Web of Science ®Google Scholar
• Ekstrom F, Pang YP, Boman M, Artursson E, Akfur C, Borjegren S. Crystal structures of acetylcholinesterase in complex with HI-6, Ortho-7 and obidoxime: Structural basis for differences in the ability to reactivate tabun conjugates. Biochem Pharmacol 2006; 72: 597–607
   PubMed Web of Science ®Google Scholar
• Kuca K, Bielavsky J, Cabal J, Kassa J. Synthesis of a new reactivator of tabun-inhibited acetylcholinesterase. Bioorg Med Chem Lett 2003; 13: 3545–3547
   PubMed Web of Science ®Google Scholar
• Kuca K, Kassa J. A comparison of the ability of a new bispyridinium oxime–1-(4-hydroxyiminomethylpyridinium)-4-(4-carbamoylpyridinium)butane dibromide and currently used oximes to reactivate nerve agent-inhibited rat brain acetylcholinesterase by in vitro methods. J Enz Inhib Med Chem 2003; 18: 529–535
   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
• Musilek K, Kuca K, Jun D, Dohnal V, Dolezal M. Synthesis of a novel series of bispyridinium compounds bearing a xylene linker and evaluation of their reactivation activity against chlorpyrifos-inhibited acetylcholinesterase. J Enz Inhib Med Chem 2005; 20: 409–415
   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, Holas O, Kuca K, Jun D, Dohnal V, Dolezal M. Synthesis of asymmetrical bispyridinium compounds bearing cyano-moiety and evaluation of their reactivation activity against tabun and paraoxon-inhibited acetylcholinesterase. Bioorg Med Chem Lett 2006; 16: 5673–5676
   PubMed Web of Science ®Google Scholar
• Bielavsky J, Kassa J, Elsnerova I, Dejmek L. Cholinesterase reactivators derived from pyridine-2-carboxaldehyde. Coll Czech Chem C 1998; 63: 199–204
   Google Scholar
• Kuca K, Cabal J. Evaluation of newly synthesized reactivators of the brain cholinesterase inhibited by sarin nerve agent. Toxicol Mech Method 2005; 15: 247–252
   PubMed Web of Science ®Google Scholar
• Tattersall JE. Ion channel blockade by oximes and recovery of diaphragm muscle from soman poisoning in vitro. Br J Pharmacol 1993; 108: 1006–1015
   PubMed Web of Science ®Google Scholar
• Worek F, Thiermann H, Szinicz L, Eyer P. Kinetic analysis of interactions between human acetylcholinesterase, structurally different organophosphorus compounds and oximes. Biochem Pharmacol 2004; 68: 2237–2248
   PubMed Web of Science ®Google Scholar
• Racakova V, Jun D, Opletalova V, Kuca K. Reactivation of acetycholinesterase inhibited by the pesticide chlorpyrifos. J Appl Biomed 2006; 4: 147–151
   Google Scholar
• Bartosova L, Kuca K, Kunesova G, Jun D. The acute toxicity of acetylcholinesterase reactivators in mice in relation to their structure. Neurotox Res 2006; 9: 291–296
   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
• Hrabinova M, Musilek K, Jun D, Kuca K. New group of xylene linker-containing acetylcholinesterase reactivators as antidotes against the nerve agent cyclosarin. J Enz Inhib Med Chem 2006; 21: 515–519
   PubMed Web of Science ®Google Scholar
• Kuca K, Cabal J, Jun D, Bajgar J, Hrabinova M. Potency of new structurally different oximes to reactivate cyclosarin-inhibited human brain acetylcholinesterases. J Enz Inhib Med Chem 2006; 21: 663–666
   PubMed Web of Science ®Google Scholar
• Picha J, Kuca K, Kivala M, Kohout M, Cabal J, Liska F. A new group of monoquaternary reactivators of acetylcholinesterase inhibited by nerve agents. J Enz Inhib Med Chem 2005; 20: 233–237
   PubMed Web of Science ®Google Scholar
• Chennamaneni SR, Vobalaboina V, Garlapati A. Quaternary salts of 4,3′ and 4,4′ bis-pyridinium monooximes: Synthesis and biological activity. Bioorg Med Chem Lett 2005; 15: 3076–3080
   PubMed Web of Science ®Google Scholar
• Srinivas Rao C, Venkateswarlu V, Achaiah G. Quaternary salts of 4,3′ and 4,4′ bis-pyridinium monooximes. Part 2: Synthesis and biological activity. Bioorg Med Chem Lett 2006; 16: 2134–2138
   PubMed Web of Science ®Google Scholar
• Pang YP, Kollmeyer TM, Hong F, Lee JC, Hammond PI, Haugabouk SP, Brimijoin S. Rational design of alkylene-linked bis-pyridiniumaldoximes as improved acetylcholinesterase reactivators. Chem Biol 2003; 10: 491–502
   PubMed Web of Science ®Google Scholar