Monooxime-monocarbamoyl bispyridinium xylene-linked reactivators of acetylcholinesterase - synthesis, in vitro and toxicity evaluation, and docking studies

ChemMedChem

Volumn 5, Issue 2, 2010, Pages 247-254

  Musilek, Kamil ^a,d   Holas, Ondrej ^b   Misik, Jan ^a   Pohanka, Miroslav ^c   Novotny, Ladislav ^c   Dohnal, Vlastimil ^d   Opletalova, Veronika ^b   Kuca, Kamil ^a,c,d  

^a UNIVERSITY OF DEFENCE   (Czech Republic)

^b Charles University in Prague Faculty of Pharmacy   (Czech Republic)

^c UNIVERSITY OF DEFENCE   (Czech Republic)

^d J E PURKINJE UNIVERSITY   (Czech Republic)

Author keywords

Acetylcholinesterases; Molecular modeling; Organophosphates; Reactivators; Tabun

Indexed keywords

1 (4 CARBAMOYLPYRIDINIO) 1' (2 HYDROXYIMINOMETHYLPYRIDINIO)DIMETHYL ETHER; 2 CARBAMOYL 2' HYDROXYIMINOMETHYL 1,1' (1,2 PHENYLENEDIMETHYL)DIBROMIDE; 2 CARBAMOYL 2' HYDROXYIMINOMETHYL 1,1' (1,3 PHENYLENEDIMETHYL)DIBROMIDE; 2 CARBAMOYL 2' HYDROXYIMINOMETHYL 1,1' (1,4 PHENYLENEDIMETHYL)DIBROMIDE; CHOLINESTERASE REACTIVATOR; K 107; K 108; K 203; METHOXIME; PRALIDOXIME; PYRIDINIUM DERIVATIVE; TRIMEDOXIME; UNCLASSIFIED DRUG; XYLENE;

ACUTE TOXICITY; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; ERYTHROCYTE; FEMALE; MOLECULAR DOCKING; MOUSE; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; TOXICITY TESTING;

ACETYLCHOLINESTERASE; ANIMALS; BINDING SITES; CARBAMATES; CHOLINESTERASE REACTIVATORS; COMPUTER SIMULATION; DRUG DESIGN; ERYTHROCYTES; HUMANS; MICE; OXIMES; PYRIDINIUM COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP; XYLENES;

EID: 75749143050     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.200900455     Document Type: Article

References (42)

1. Cholinesterases and Cholinesterase Inhibitors, (Ed.: E. Giacobini), Martin Dunitz, London, 2000.
2. E. Giacobini, Pharmacol. Res. 2004, 50, 433-440.
3. J. Bajgar, Adv. Clin. Chem. 2004, 38, 151-216.
4. T. C. Marrs, Pharmacol. Ther. 1993, 58, 51-66.
5. Toxicology of organophosphate & carbamate compounds, (Ed.: R. C. Gupta), Elsevier Academic Press, London, 2006; pp. 5-69, 703-714.
6. A. Saxena, W. Sun, C. Luo, T. M. Myers, I. Koplovitz, D. E. Lenz, B. P. Doctor, J. Mol. Neurosci. 2006, 30, 145-148.
7. A. Lucic, B. Radic, M. Peraica, M. Mesic, I. Primozic, Z. Binenfeld, Arch. Toxicol. 1997, 71, 467- 470.
8. A. Lucić Vrdoljak, M. Ć alić, B. Radić, S. Berend, D. Jun, K. Kuća, Z. Kovarik, Toxicology 2006, 228, 41-50.
9. E. J. Poziomek, B. E. Hackley, G. M. Steinberg, J. Org. Chem. 1958, 23, 714-717.
10. A. Lüttringhaus, I. Hagedorn, Arzneim. Forsch. 1964, 14, 1-5.
11. I. Hagedorn, W. H. Gündel, K. Schoene, Arzneim. Forsch. 1969, 19, 603-606.
12. F. Worek, P. Eyer, N. Aurbek, L. Szinicz, H. Thiermann, Toxicol. Appl. Pharmacol. 2007, 219, 226-234.
13. A. Hörnberg, A.-K. Tunemalm, F. Ekstrom, Biochemistry 2007, 46, 4815-4825.
14. N.-J. Park, Y.-S. Jung, K. Musilek, D. Jun, K. Kuca, Bull. Korean Chem. Soc. 2006, 27, 1401-1404.
15. H. Kalász, M. Y. Hasan, R. Sheen, K. Kuca, G. Petroianu, K. Ludanyi, A. Gergely, K. Tekes, Anal. Bioanal. Chem. 2006, 385, 1062-1067.
16. R. Odzak, M. Calic, T. Hrenar, I. Primozic, Z. Kovarik, Toxicology 2007, 233, 85-96.
17. G. A. Petroianu, K. Arafat, K. Kuca, J. Kassa, J. Appl. Toxicol. 2006, 26, 64-71.
18. D. E. Lorke, M. Y. Hasan, K. Arafat, K. Kuca, K. Musilek, A. Schmitt, G. A. Petroianu, J. Appl. Toxicol. 2008, 28, 422-429.
19. K. Musilek, K. Kuca, D. Jun, V. Dohnal, M. Dolezal, J. Enzyme Inhib. Med. Chem. 2005, 20, 409-415.
20. K. Musilek, K. Kuca, D. Jun, V. Dohnal, M. Dolezal, J. Enzyme Inhib. Med. Chem. 2007, 22, 425-432.
21. D. E. Lorke, S. M. Nurulain, M. Y. Hasan, K. Kuca, K. Musilek, G. A. Petroianu, J. Appl. Toxicol. 2008, 28, 920-928.
22. K. Musilek, D. Jun, J. Cabal, J. Kassa, F. Gunn-Moore, K. Kuca, J. Med. Chem. 2007, 50, 5514-5518.
23. K. Kuca, J. Bielavsky, J. Cabal, M. Bielavska, Tetrahedron Lett. 2003, 44, 3123-3125.
24. K. Kuca, J. Bielavsky, J. Cabal, J. Kassa, Bioorg. Med. Chem. Lett. 2003, 13, 3545-3547.
25. J. Kassa, J. Karasova, K. Musilek, K. Kuca, Toxicology 2008, 243, 311-316.
26. K. Musilek, O. Holas, K. Kuca, D. Jun, V. Dohnal, V. Opletalova, M. Dolezal, Bioorg. Med. Chem. Lett. 2007, 17, 3172-3176.
27. K. Musilek, K. Kuca, D. Jun, V. Dohnal, M. Dolezal, Bioorg. Med. Chem. Lett. 2006, 16, 622 -627.
28. K. Musilek, O. Holas, D. Jun, V. Dohnal, F. Gunn-Moore, V. Opletalova, M. Dolezal, K. Kuca, Bioorg. Med. Chem. 2007, 15, 6733-6741.
29. M. Pohanka, D. Jun, K. Kuca, Talanta 2008, 77, 451-454.
30. J. E. Tattersall, Br. J. Pharmacol. 1993, 108, 1006-1015.
31. K. Musilek, O. Holas, J. Hambalek, K. Kuca, D. Jun, V. Dohnal, M. Dolezal, Lett. Org. Chem. 2006, 3, 831-835.
32. G. Sinko, M. Calic, A. Bosak, Z. Kovarik, Anal. Biochem. 2007, 370, 223-227.
33. J. Kassa, D. Jun, K. Kuca, Int. J. Toxicol. 2006, 25, 397-401.
34. J. Kassa, Neurotoxic. Res. 2006, 9, 59-62.
35. J. Kassa, Acta Med. (Hradec Kralove, Czech Repub.) 1998, 41, 19-21.
36. S. M. Nurulain, D. E. Lorke, M. Y. Hasan, M. Shafiullah, K. Kuca, K. Musilek, G. A. Petroianu, Neurotoxic. Res. 2009, 16, 60-67.
37. K. Kuca, D. Jun, K. Musilek, Mini-Rev. Med. Chem. 2006, 6, 269-277.
38. R. J. Tallarida, R. B. Murray, Manual of Pharmacologic Calculation with Computer Programs, Springer-Verlag, New York, 1987, p. 145.
39. G. M. Morris, D. S. Goodsell, R. S. Halliday, R. Huey, W. E. Hart, R. K. Belew, A. J. Olson, J. Comput. Chem. 1998, 19, 1639-1662.
40. available online via the Protein Data Bank: http://www.pdb.org.
41. E. F. Pettersen, T. D. Goddard, C. C. Huang, G. S. Couch, D. M. Greenblatt, E. C. Meng, T. E. Ferrin, J. Comput. Chem. 2004, 25, 1605-1612.
42. W. L.DeLano, The PyMOL Molecular Graphics System, 2002: http:// www.pymol.org.