Oximes acetylcholinesterase reactivation

Maurizis JC, Olher M, Nicolas C et al. (1992). In vitro binding of oxime acetylcholinesterase reactivators to proteoglycans synthesized by cultured chondrocytes and fibroblasts. Biochem Pharmacol, 44, 1927-1933. 

Jun, D., Musilova, L., Lazenska, H., Kuca, K., Kassa, J., Bajgar, J. (2007). Potency of several oximes to reactivate human acetylcholinesterase and hutyrylcholinesterase inWhited by paraoxon and methyl-paraoxon in vitro. The IXth International Meeting on Cholinesterases. Suzhou, CWna, May 6-10, 2007. Program Book, p. 140. 

Stojiljkovic, M.P., Pantelic, D., Maksimovic, M. (2001). Tabun, sarin, soman and VX poisoning in rats kinetics of inhibition of central and peripheral acetylcholinesterase, ageing, spontaneous and oxime-facilitated reactivation. Vll International Symposium on Protection against Chemical and Biological Agents. Stockholm, Sweden, June 15-19,... 

Acharya, J., Gupta, A.K., Dubey, D.K., Raza, S.K. (2008b). Synthesis and evaluation of novel bis-pyridinium oximes as reactivators of DFP-inhibited acetylcholinesterase. Eur. J. Med. Chem. doi 10.1016/jejmech.2008.02.029. 

Kim, T.H., Kuca, K., Jun, D., Jung, Y.S. (2005). Design and synthesis of new bis-pyridinium oximes as cyclosarin-inhibited acetylcholinesterase reactivators. Bioorg. Med. Chem. Lett. 15 2914-17. 

Kuca, K., Kassa, J. (2003). A comparison of the ability of a new bispyridinium oxime-l-(4-hydroxyiminomethylpyridinium)-4-(4-carbamoylpyridinium)butane dibromide and currently used oximes to reactivate nerve agent-inhibited rat brain acetylcholinesterase by in vitro methods. J. Enzyme Inhib. Med. Chem. 18 529-35. 

Clement, J.G. and Erhardt, N. In vitro oxime-induced reactivation of various molecular forms of soman-inhibited acetylcholinesterase in striated muscle from rat, monkey and human. Arch. Toxicol., 68, 648, 1994. 

Hanke, D.W. and Overton, M.A. 1991, Phosphylation kinetic constants and oxime-induced reactivation in acetylcholinesterase from fetal bovine serum, bovine caudate nucleus, and electric eel, J. Toxicol Environ. Health, vol. 34, no. 1, pp. 141-156. 

L35. Loomis, T. A., Welsh, M. J., Jr., and Miller, G. T., A comparative study of some pyridinium oximes as reactivators of phosphorylated acetylcholinesterase and as antidotes in sarin poisoning. Toxicol. Appl. Pharmacol. 5, 588-598 (1963). 

Jokanovic, M., Maksimovic, M., Kilibarda, V., Jovanovic, D., and Savic, D. Oxime-induced reactivation of acetylcholinesterase inhibited by phosphoramidates, Toxicol. Lett., 85,35-39, 1996. 

Busker RW, Zijlstra JJ, van der Wiel HJ et al. (1991). Organophosphate poisoning a method to test therapeutic effects of oximes other than acetylcholinesterase reactivation in the rat. Toxicology, 69, 331-344. 

Harris LW, Anderson DR, Lennox WJ et al. (1990). Evaluation of several oximes as reactivators of unaged soman-inhibited whole blood acetylcholinesterase in rabbits. Biochem Pharmacol, 40, 2677-2682. 

Luo C, Ashani Y and Doctor BP (1998a). Acceleration of oxime-induced reactivation of organophosphate -inhibited fetal bovine serum acetylcholinesterase by monoquaternary and bisquaternary ligands. Mol Pharmacol, 53, 718-726. 

Su C-T, Wang P-H, Liu R-F et al. (1986). Kinetic studies and structure-activity relationships of bispyridinium oximes as reactivators of acetylcholinesterase inhibited by organophosphorus compounds. Fund Appl Toxicol, 6, 506-524. 

V-Alkylation of p)ridazine is achieved using alkyl bromides the access via iV-alkylation to new mono-oxime bis-quaternary acetylcholinesterase reactivators used in the treatment of organophosphorous poisoning has been reported (eq 4). The alkylation takes place in DMF at 60 °C and provides the bis-quaternary salt in very good yield (92%). 

Jun, D., Musilova, L., Musilek, K., et al., 2011. In vitro ability of currently available oximes to reactivate organophosphate pesticide-inhibited human acetylcholinesterase and butyrylcholinesterase. Int. J. Mol. Sci. 12, 2077-2087. 

Musilek, K., Komloova, M., Holas, O., et al., 2011b. Mono-oxime bisquaternary acetylcholinesterase reactivators with prop-l,3-diyl linkage-preparation, in vitro screening and molecular docking. Bioorg. Med. Chem. 19, 754-762. 

C. L. Cadieux, C. A. Broomfield, M. G. Kirkpatrick, M. E. Kazanski, D. E. Lenz and D. M. Cerasoli, Comparison of human and guinea pig acetylcholinesterase sequences and rates of oxime-assisted reactivation, Chem.-Biol Interact., 2010,187, 229-233. 

Hansen ME, Wilson BW. 1999. Oxime reactivation of RBC acetylcholinesterases for biomonitoring. Arch Environ Contam Toxicol 37 283-289. 

---