Monooxime reactivators of acetylcholinesterase with (E)-but-2-ene linker-Preparation and reactivation of tabun- and paraoxon-inhibited acetylcholinesterase

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 21, 2007, Pages 6733-6741

  Musilek, Kamil ^a,b   Holas, Ondrej ^a   Jun, Daniel ^b,c   Dohnal, Vlastimil ^d   Gunn Moore, Frank ^e   Opletalova, Veronika ^a   Dolezal, Martin ^a   Kuca, Kamil ^b,c  

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

^b UNIVERSITY OF DEFENCE   (Czech Republic)

^c UNIVERSITY OF DEFENCE   (Czech Republic)

^d MENDEL UNIVERSITY IN BRNO   (Czech Republic)

^e UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

Acetylcholinesterase; Nerve agent; Oxime; Paraoxon; Pesticide; Reactivation; Reactivator; Tabun

Indexed keywords

1 (4 BENZYLPYRIDINIUM) 4 (4 HYDROXYIMINOMETHYLPYRIDINIUM)BUT 2 ENE DIBROMIDE; 1 (4 CARBAMOYLPYRIDINIO) 1' (2 HYDROXYIMINOMETHYLPYRIDINIO)DIMETHYL ETHER; 1 (4 CARBONITRILEPYRIDINIUM) 4 (4 HYDROXYIMINOMETHYLPYRIDINIUM)BUT 2 ENE DIBROMIDE; 1 (4 CARBOXYPYRIDINIUM) 4 (4 HYDROXYIMINOMETHYLPYRIDINIUM)BUT 2 ENE DIBROMIDE; 1 (4 ETHYLCARBOXYPYRIDINIUM) 4 (4 HYDROXYIMINOMETHYPYRIDINIUM)BUT 2 ENE DIBROMIDE; 1 (4 HYDROXYIMINOMETHYLPYRIDINIUM) 4 (4 HYDROXYMETHYLPYRIDINIUM)BUT 2 ENE DIBROMIDE; 1 (4 HYDROXYIMINOMETHYLPYRIDINIUM) 4 (4 METHYLCARBONYLPYRIDINIUM)BUT 2 ENE DIBROMIDE; 1 (4 HYDROXYIMINOMETHYLPYRIDINIUM) 4 (4 METHYLPYRIDINIUM)BUT 2 ENE DIBROMIDE; 1 (4 HYDROXYIMINOMETHYLPYRIDINIUM) 4 (4 PHENYLPYRIDINIUM)BUT 2 ENE DIBROMIDE; 1 (4 HYDROXYIMINOMETHYLPYRIDINIUM) 4 (4 TERT BUTYLPYRIDINIUM)BUT 2 ENE DIBROMIDE; 1 (4 HYDROXYIMINOMETHYLPYRIDINIUM) 4 [4 (1 THIA 2 CARBOXYETHYL)PYRIDINIUM]BUT 2 ENE DIBROMIDE; 1 (4 HYDROXYIMINOMETHYLPYRIDINIUM) 4 ISOQUINOLINIUM BUT 2 ENE DIBROMIDE; 1 (4 HYDROXYIMINOMETHYLPYRIDINIUM) 4 PYRIDINIUM BUT 2 ENE DIBROMIDE; 1 (4 HYDROXYIMINOMETHYLPYRIDINIUM) 4 PYRIIAZINIUM BUT 2 ENE DIBROMIDE; 1 (4 HYDROXYIMINOMETHYLPYRIDINIUM) 4 QUINOLINIUM BUT 2 ENE DIBROMIDE; 1 [4 (1 AMINOHYDROXYIMINOMETHYL)PYRIDINIUM] 4 (4 HYDROXYIMINOMETHYLPYRIDINIUM)BUT 2 ENE DIBROMIDE; ACETYLCHOLINESTERASE; K 075; K 203; OBIDOXIME; OXIME DERIVATIVE; PARAOXON; PRALIDOXIME; TABUN; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CONTROLLED STUDY; COVALENT BOND; ENZYME INHIBITION; INTOXICATION; LIPOPHILICITY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; STRUCTURE ACTIVITY RELATION;

ACETYLCHOLINESTERASE; ANIMALS; ANTIDOTES; CHOLINESTERASE INHIBITORS; CHOLINESTERASE REACTIVATORS; DRUG DESIGN; OXIMES; PARAOXON; PHOSPHORIC ACID ESTERS; RATS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34548524594     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.08.002     Document Type: Article

References (38)

1. Giacobini E. In: Giacobini E. (Ed). Cholinesterases and Cholinesterase Inhibitors (2000), Martin Dunitz, London 1-226
2. Giacobini E. Pharmacol. Res. 50 (2004) 433
3. Bajgar J. Adv. Clin. Chem. 38 (2004) 151
4. Marrs T.C. Pharmacol. Ther. 58 (1993) 51
5. Gupta R. Toxicology of Organophosphate & Carbamate Compounds (2006), Elsevier Academic Press, London 5-69 703-714
6. Saxena A., Sun W., Luo C., Myers T.M., Koplovitz I., Lenz D.E., and Doctor B.P. J. Mol. Neurosci. 30 (2006) 145
7. Lucic A., Radic B., Peraica M., Mesic M., Primozic I., and Binenfeld Z. Arch. Toxicol. 71 (1997) 467
8. Lucic-Vrdoljak A., Calic M., Radic B., Berend S., Jun D., Kuca K., and Kovarik Z. Toxicology 228 (2006) 41
9. Poziomek E.J., Hackley B.E., and Steinberg G.M. J. Org. Chem. 23 (1958) 714
10. Lüttringhaus A., and Hagedorn I. Arzneimittelforschung 14 (1964) 1
11. Hagedorn I., Gündel W.H., and Schoene K. Arzneimittelforschung 19 (1969) 603
12. Bajgar J., Fusek J., Kuca K., Bartosova L., and Jun D. Mini-Rev. Med. Chem. 7 (2007) 461
13. Lundy P.M., Raveh L., and Amitai G. Toxicol. Rev. 25 (2006) 231
14. Ekstrom F., Akfur C., Tunemalm A.K., and Lundberg S. Biochemistry 45 (2006) 74
15. Ekstrom F., Pang Y.P., Boman M., Artursson E., Akfur C., and Borjegren S. Biochem. Pharmacol. 72 (2006) 597
16. Calic M., Lucic A., Radic B., Jelic D., Jun D., Kuca K., and Kovarik Z. Toxicology 219 (2006) 85
17. Park N.-J., Jung Y.-S., Musilek K., Jun D., and Kuca K. Bull. Korean Chem. Soc. 27 (2006) 1401
18. Kalasz H., Hasan M.Y., Sheen R., Kuca K., Petroianu G., Ludanyi K., Gergely A., and Tekes K. Anal. Bioanal. Chem. 385 (2006) 1062
19. Odzak R., Calic M., Hrenar T., Primozic I., and Kovarik Z. Toxicology 233 (2007) 85
20. Kuca K., Bielavsky J., Cabal J., and Bielavska M. Tetrahedron Lett. 44 (2003) 3123
21. Kuca K., Bielavsky J., Cabal J., and Kassa J. Bioorg. Med. Chem. Lett. 13 (2003) 3545
22. Pang Y.-P., Kollmeyer T.M., Hong F., Lee J.-C., Hammond P.I., Haugabouk S.P., and Brimijoin S. Chem. Biol. 10 (2003) 491
23. Kuca K., Cabal J., Musilek K., Jun D., and Bajgar J. J. Appl. Toxicol. 25 (2005) 491
24. Musilek, K.; Holas, O.; Kuca, K.; Jun, D.; Dohnal, V.; Opletalova, V.; Dolezal, M. J. Enzyme Inhib. Med. Chem. 2007, MS 238287.
25. Musilek, K.; Jun, D.; Cabal, J.; Kassa, J.; Gunn-Moore, F.; Kuca, K. J. Med. Chem. MS JM070653R.
26. Musilek K., Kuca K., Jun D., and Dolezal M. Curr. Org. Chem. 11 (2007) 229
27. Musilek K., Holas O., Hambalek J., Kuca K., Jun D., Dohnal V., and Dolezal M. Lett. Org. Chem. 3 (2006) 831
28. Kuca K., Jun D., and Musilek K. Mini-Rev. Med. Chem. 6 (2006) 269
29. Musilek K., Kuca K., Jun D., Dohnal V., and Dolezal M. Bioorg. Med. Chem. Lett. 16 (2006) 622
30. Musilek K., Holas O., Kuca K., Jun D., Dohnal V., and Dolezal M. Bioorg. Med. Chem. Lett. 16 (2006) 5673
31. Kuca K., and Cabal J. Toxicol. Mech. Method 15 (2005) 247
32. Jokanovic M., and Stojiljkovic M.P. Eur. J. Pharmacol. 553 (2006) 10
33. Tattersall J.E. Br. J. Pharmacol. 108 (1993) 1006
34. Musilek K., Kuca K., Jun D., Dohnal V., and Dolezal M. J. Enzyme Inhib. Med. Chem. 20 (2005) 409
35. Musilek K., Kuca K., Jun D., Dohnal V., and Dolezal M. J. Enzyme Inhib. Med. Chem. 22 (2007) 425
36. Kuca K., Patocka J., and Cabal J. J. Appl. Biomed. 1 (2003) 207
37. Carey F.A., and Sundberg R.J. The Structure and Mechanisms. 4th ed. (2000), Plenum Publishers, New York 13
38. Musilek K., Holas O., Kuca K., Jun D., Dohnal V., Opletalova V., and Dolezal M. Bioorg. Med. Chem. Lett. 17 (2007) 3172