Monoquaternary pyridinium salts with modified side chain-synthesis and evaluation on model of tabun- and paraoxon-inhibited acetylcholinesterase

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 17, 2008, Pages 8218-8223

  Musilek, Kamil ^a,b   Kucera, Jiri ^b   Jun, Daniel ^a,c   Dohnal, Vlastimil ^d   Opletalova, Veronika ^b   Kuca, Kamil ^a,c  

^a UNIVERSITY OF DEFENCE   (Czech Republic)

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

^c UNIVERSITY OF DEFENCE   (Czech Republic)

^d MENDEL UNIVERSITY IN BRNO   (Czech Republic)

Author keywords

Acetylcholinesterase; Monoquaternary; Oxime; Paraoxon; Reactivator; Tabun

Indexed keywords

1 (4 CARBAMOYLPYRIDINIO) 1' (2 HYDROXYIMINOMETHYLPYRIDINIO)DIMETHYL ETHER; ACETYLCHOLINESTERASE; CHOLINESTERASE REACTIVATOR; OBIDOXIME; PARAOXON; PRALIDOXIME; PYRIDINIUM DERIVATIVE; TABUN; TRIMEDOXIME;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DESIGN; DRUG PURIFICATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; IN VITRO STUDY; INTOXICATION; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

ACETYLCHOLINESTERASE; ANIMALS; BRAIN; CHOLINESTERASE INHIBITORS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; ENZYME ACTIVATION; ENZYME ACTIVATORS; MODELS, BIOLOGICAL; MOLECULAR STRUCTURE; PARAOXON; PHOSPHORIC ACID ESTERS; PYRIDINIUM COMPOUNDS; RATS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 50349087692     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.07.036     Document Type: Article

References (37)

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. Marrs T.C. Pharmacol. Therap. 58 (1993) 51
4. Bajgar J. Adv. Clin. Chem. 38 (2004) 151
5. Saxena A., Sun W., Luo C., Myers T.M., Koplovitz I., Lenz D.E., and Doctor B.P. J. Mol. Neurosci. 30 (2006) 145
6. Hagedorn I., Gündel W.H., and Schoene K. Arzneimittelforschung 19 (1969) 603
7. Lüttringhaus A., and Hagedorn I. Arzneimittelforschung 14 (1964) 1
8. Poziomek E.J., Hackley B.E., and Steinberg G.M. J. Org. Chem. 23 (1958) 714
9. Ekstrom F., Akfur C., Tunemalm A.K., and Lundberg S. Biochemistry 45 (2006) 74
10. Ekstrom F., Pang Y.P., Boman M., Artursson E., Akfur C., and Borjegren S. Biochem. Pharmacol. 72 (2006) 597
11. de Jong L.P.A., Benschop H.P., van den Berg G.R., Wolring G.Z., and de Korte D.C. Eur. J. Med. Chem. 16 (1981) 257
12. Odzak R., Calic M., Hrenar T., Primozic I., and Kovarik Z. Toxicology 233 (2007) 85
13. Okuno S., Sakurada K., Ohta H., Ikegaya H., Kazui Y., Akutsu T., Takatori T., and Iwadate K. Toxicol. Appl. Pharmacol. 227 (2008) 8
14. Bajgar J., Fusek J., Kuca K., Bartosova L., and Jun D. Mini-Rev. Med. Chem. 7 (2007) 461
15. Luo C., Tong M., Chilukuri N., Brecht K., Maxwell D.M., and Saxena A. Biochemistry 46 (2007) 11771
16. Thiermann H., Mast U., Klimmek R., Eyer P., Hibler A., Pfab R., Felgenhauer N., and Zilker T. Hum. Exp. Toxicol. 16 (1997) 473
17. Szinicz L., Worek F., Thiermann H., Kehe K., Eckert S., and Eyer P. Toxicology 233 (2007) 23
18. Musilek K., Jampilek J., Dohnal J., Jun D., Gunn-Moore F., Dolezal M., and Kuca K. Anal. Bioanal. Chem. 391 (2008) 367
19. Sakurada K., Matsubara K., Shimizu K., Shiono H., Seto Y., Tsuge K., Yoshino M., Sakai I., Mukoyama H., and Takatori T. Neurochem. Res. 28 (2003) 1401
20. Lorke D.E., Kalasz H., Petroianu G.A., and Tekes K. Curr. Med. Chem. 15 (2008) 743
21. Musilek K., Kuca K., Jun D., Dohnal V., and Dolezal M. J. Enzym. Inhib. Med. Chem. 20 (2005) 409
22. Musilek K., Kuca K., Jun D., Dohnal V., and Dolezal M. Bioorg. Med. Chem. Lett. 16 (2006) 622
23. Musilek K., Kuca K., Jun D., Dohnal V., and Dolezal M. J. Enzym. Inhib. Med. Chem. 22 (2007) 425
24. Musilek K., Holas O., Kuca K., Jun D., Dohnal V., Opletalova V., and Dolezal M. Bioorg. Med. Chem. Lett. 17 (2007) 3172
25. Chennamaneni S.R., Vobalaboina V., and Garlapati A. Bioorg. Med. Chem. Lett. 15 (2005) 3076
26. Srinivas R.C., Venkateswarlu V., and Achaiah G. Bioorg. Med. Chem. Lett. 16 (2006) 2134
27. Musilek K., Holas O., Jun D., Dohnal V., Gunn-Moore F., Opletalova V., Dolezal M., and Kuca K. Bioorg. Med. Chem. 15 (2007) 6733
28. Musilek K., Lipka L., Racakova V., Kuca K., Jun D., Dohnal V., and Dolezal M. Chem. Pap. 60 (2006) 48
29. Musilek K., Kuca K., Jun D., and Dolezal M. Lett. Org. Chem. 3 (2006) 831
30. Kuca K., and Cabal J. Toxicol. Mech. Method 15 (2005) 247
31. Bajgar J., Kuca K., Jun D., Bartosova L., and Fusek J. Curr. Drug Metab. 8 (2007) 803
32. Lundy P.M., Raveh L., and Amitai G. Toxicol. Rev. 25 (2006) 231
33. Jokanovic M., and Stojiljkovic M.P. Eur. J. Pharmacol. 553 (2006) 10
34. Musilek K., Jun D., Cabal J., Kassa J., Gunn-Moore F., and Kuca K. J. Med. Chem. 50 (2007) 5514
35. Tattersall J.E. Br. J. Pharmacol. 108 (1993) 1006
36. Kuca K., Jun D., and Musilek K. Mini-Rev. Med. Chem. 6 (2006) 269
37. Kuca K., Jun D., Musilek K., and Bajgar J. Front. Drug Des. Discov. 3 (2007) 381