para- and ortho-Pyridinium aldoximes in reaction with acetylthiocholine

FEBS Letters

Volumn 580, Issue 13, 2006, Pages 3167-3172

  Šinko, Goran ^a   Čalić, Maja ^a   Kovarik, Zrinka ^a  

^a INSTITUTE FOR MEDICAL RESEARCH AND OCCUPATIONAL HEALTH   (Croatia)

Author keywords

Conformational analysis; Dissociation constants; Oximolysis; Pyridinium aldoxime; Spectrophotometry; Titration

Indexed keywords

ACETYLTHIOCHOLINE; ALDOXIME; OXIME DERIVATIVE; PYRIDINIUM DERIVATIVE;

ABSORPTION SPECTROPHOTOMETRY; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; SPECTROPHOTOMETRY; STEREOSPECIFICITY; THERMODYNAMICS;

ACETYLTHIOCHOLINE; OXIMES; PYRIDINIUM COMPOUNDS; THERMODYNAMICS; TRIMEDOXIME;

EID: 33646545038     PISSN: 00145793     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.febslet.2006.04.070     Document Type: Article

References (23)

1. Gray A.P. Design and structure-activity relationships of antidotes to organophosphorus anticholinesterase agents. Drug Metab. Rev. 15 (1984) 557-589
2. Dawson R.M. Review of oximes available for treatment of nerve agent poisoning. J. Appl. Toxicol. 14 (1994) 317-331
3. Kassa J. Review of oximes in the antidotal treatment of poisoning by organophosphorus nerve agents. J. Toxicol.- Clin. Toxic. 40 (2002) 803-816
4. Schoene K., and Strake E.-M. Reaktivierung von diäthylphosphoryl-acetylcholinestrase Affinität und reaktivität einiger pyridiniumoxime. Biochem. Pharmacol. 20 (1971) 1041-1051
5. Bunton C.A., Gillitt N.D., and Kumar A. Solvent effects on reactions of hydroxide and oximate ions with phosphorus(V) esters. J. Phys. Org. Chem. 10 (1997) 221-228
6. Lovrić J., Burger N., Deljac V., and Mihalić Z. Spectrophotometric studies of some novel derivates of pyridinium chloride. Croat. Chem. Acta 72 (1999) 123-133
7. Castro A.T., and Figueroa-Villar J.D. Molecular structure, conformational analysis and charge distribution of pralidoxime: Ab initio and DFT studies. Int. J. Quantum Chem. 89 (2002) 135-146
8. Mager P.P., and Weber A. Structural bioinformatics and QSAR analysis applied to the acetylcholinesterase and bispyridinium aldoximes. Drug Des. Discov. 18 (2003) 127-150
9. Čalić M., Lucić Vrdoljak A., Radić B., Jelić D., Jun D., Kuča K., and Kovarik Z. In vitro and in vivo evaluation of pyridinium oximes: mode of interaction with acetylcholinesterase, effect on tabun- and soman-poisoned mice and their cytotoxicity. Toxicology 219 (2006) 85-96
10. Petroianu G.A., Arafat K., Kuča K., and Kassa J. Five oximes (K-27, K-33, K-48, BI-6 and methoxime) in comparison with pralidoxime: in vitro reactivation of red blood cell acetylcholinesterase inhibited by paraoxon. J. Appl. Toxicol. 26 (2006) 64-71
11. Kovarik Z., Bosak A., Šinko G., and Latas T. Exploring active sites of cholinesterases by inhibition with bambuterol and haloxon. Croat. Chem. Acta 76 (2003) 63-67
12. Šinko G., Bosak A., Kovarik Z., and Simeon-Rudolf V. Structure-inhibition relationships in the interaction of butyrylcholinesterase with bambuterol, haloxon and their leaving groups. Chem.-Biol. Interact. 157-158 (2005) 421-423
13. Foretić B., and Burger N. The dissociation constants of 1,1′-bis(pyridinium-4-aldoxime)trimethylene dibromide. Monatsh. Chem. 135 (2004) 261-267
14. Čakar M.M., Vasić V.M., Petkovska Lj.T., Stojić D.Lj., Avramov-Ivić M., and Milovanović G.A. Spectrophotometric and electrochemical study of protolytic equilibria of some oximes-acetylcholinesterase reactivators. J. Pharm. Biomed. 20 (1999) 655-662
15. Stojan J., and Pavlič M.R. Velocity of Ellman's reaction and its implication for kinetic studies in the millisecond time range. Neurochem. Res. 17 (1992) 1207-1210
16. Goličnik M., Šinko G., Simeon-Rudolf V., Grubič Z., and Stojan J. Kinetic model of ethopropazine interaction with horse serum butyrylcholinesterase and its docking into the active site. Arch. Biochem. Biophys. 398 (2002) 23-31
17. Fersht A. Structure and Mechanism in Protein Science: A Guide to Enzyme Catalysis and Protein Folding (1998), W.H. Freeman and Company, New York
18. Stern E.S., and Timmons C.J. Gillam and Stern's Introduction to Electronic Absorption Spectroscopy in Organic Chemistry (1970), Edward Arnold Ltd., London p. 149
19. Kovarik Z., Radić Z., Simeon-Rudolf V., Reiner E., and Taylor P. Acetylcholinesterase mutants: oxime-assisted catalytic scavengers of organophosphonates. Chem.-Biol. Interact. 157-158 (2005) 388-390
20. Petroianu G.A., Missler A., Zuleger K., Thyes C., Ewald V., and Maleck W.H. Enzyme reactivator treatment in organophosphate exposure: clinical relevance of thiocholinesteratic activity of pralidoxime. J. Appl. Toxicol. 24 (2004) 429-435
21. Pannbacker R.G., and Oehme F.W. Pralidoxime hydrolysis of thiocholine esters. Vet. Human Toxicol. 45 (2003) 39-40
22. Worek F., Thiermann H., Szinicz L., and Eyer P. Kinetic analysis of interactions between human acetylcholinesterase, structurally different organophosphorus compounds and oximes. Biochem. Pharmacol. 68 (2004) 2237-2248
23. Kovarik Z., Radić Z., Berman H.A., Simeon-Rudolf V., Reiner E., and Taylor P. Mutant cholinesterases possessing enhanced capacity for reactivation of their phosphonylated conjugates. Biochemistry 43 (2004) 3222-3229