In vitro reactivation potency of novel symmetrical bis-pyridinium oximes for electric eel acetylcholinesterase inhibited by nerve agent sarin

Toxicology in Vitro

Volumn 25, Issue 8, 2011, Pages 2135-2139

  Acharya, Jyotiranjan ^a   Dubey, Devendra Kumar ^a   Kaushik, M P ^a  

^a DEFENCE RESEARCH AND DEVELOPMENT ESTABLISHMENT   (India)

Author keywords

2 PAM; Acetylcholinesterase; Bis pyridinium oximes; Obidoxime; Reactivators; Sarin

Indexed keywords

1,3 DIMETHOXY BENZENE BIS[3,3' (HYDROXYIMINOMETHYL)PYRIDINIUM]DICHLORIDE; 1,4 BIS METHOXYMETHYL CIS BUT 2 ENE; 1,4 BIS METHOXYMETHYL CIS BUT 2 YNE; 1,4 DIMETHOXY BENZENE BIS[3,3' (HYDROXYAMINO METHYL)PYRIDINIUM]DICHLORIDE; 1,4 DIMETHOXY CIS BUT 2 ENE BIS[4,4' (HYDROXYAMINO METHYL)PYRIDINIUM]DICHLORIDE; ACETYLCHOLINESTERASE; BENZENE DERIVATIVE; BIS PYRIDINIUM OXIME DERIVATIVE; OBIDOXIME; OXIME DERIVATIVE; SARIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DISSOCIATION CONSTANT; DRUG EFFICACY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; EEL; ELECTRIC EEL; ENZYME REACTIVATION; IN VITRO STUDY; NONHUMAN;

ANIMALS; CHEMICAL WARFARE AGENTS; CHOLINESTERASE INHIBITORS; CHOLINESTERASE REACTIVATORS; ELECTROPHORUS; OXIMES; PYRIDINIUM COMPOUNDS; SARIN;

ELECTROPHORUS ELECTRICUS;

EID: 82655162182     PISSN: 08872333     EISSN: 18793177     Source Type: Journal    
DOI: 10.1016/j.tiv.2011.06.014     Document Type: Article

References (37)

1. Acharya J., Dubey D.K., Raza S.K. In-vitro evaluation of bis-pyridinium oximes bearing methoxy alkane linker as reactivators of sarin inhibited human acetylcholinesterase. Toxicology in Vitro 2010, 24:1797-1802.
2. Acharya J., Gupta A.K., Dubey D.K., Raza S.K. Synthesis and evaluation of novel bis-pyridinium oximes as reactivators of DFP-inhibited acetylcholinesterase. European Journal of Medicinal Chemistry 2009, 44:1335-1340.
3. Acharya J., Gupta A.K., Mazumder A., Dubey D.K. In-vitro regeneration of sarin inhibited electric eel acetylcholinesterase by bis-pyridinium oximes bearing xylene linker. European Journal of Medicinal Chemistry 2009, 44:1326-1330.
4. Acharya J., Gupta A.K., Mazumder A., Dubey D.K. In-vitro reactivation of sarin inhibited electric eel acetylcholinesterase by bis-pyridinium oximes bearing methoxy ether linkages. Toxicology in Vitro 2008, 22:525-530.
5. Albert A., Sergeant E.P. The Determinations of ionization Constants: A Laboratory Manual 1971, Chapman and Hall, London.
6. Aldridge W.N., Reiner E. Enzyme Inhibitors as Substrates: Interactions of Esterases with Esters of Organophosphorus and Carbamic Acids 1972, North-Holland, Amsterdam.
7. Bajgar J. Organophosphates/nerve agent poisoning: mechanism of action, diagnosis, prophylaxis, and treatment. Advances in Clinical Chemistry 2004, 38:151-216.
8. Bismuth C., Inns R.H., Marrs T.C. Efficacy, toxicity and clinical use of oximes in anticholinesterase poisoning. Clinical and Experimental Toxicology of Organophosphates and Carbamates 1992, 555. Butterworth and Heinemann, Oxford. B. Ballantyne, T.C. Marrs (Eds.).
9. Cabal J., Kassa J., Patocka J. Inhibition of plasma cholinesterase by O -alkylfluorophosphonates. Collection of Czechoslovak Chemical Communications 1997, 62:521-526.
10. Chennamaneni S.R., Venkateshwarulu V., Achaiah G. Quaternary salts of 4,3′ and 4,4′bis-pyridinium monooximes: synthesis and biological activity. Bioorganic and Medicinal Chemistry Letters 2005, 15:3076-3080.
11. Ellman G.L., Courtny K.D., Andres V., Featherstone R.M. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochemical Pharmacology 1961, 16:88-95.
12. Eto M. Organophosphorus Pesticides: Organic and Biological Chemistry 1974, CRC press, USA, p. 139.
13. Eyer P. The role of oximes in the management of organophosphorus pesticide poisoning. Toxicological Reviews 2003, 22:165-190.
14. Farren J.W., Fife H.R., Clark F.E., Garland C.E. Chloroethers II. Preparation of some new chloroethers and alkoxy methyl esters. Journal of the American Chemical Society 1925, 47:2419-2423.
15. Ginsburg S., Wilson I.B. Oximes of the pyridine series. Journal of the American Chemical Society 1957, 79:481-485.
16. Gomori G. Preparation of buffers for use in enzyme studies. Methods in Enzymology 1955, vol. I:138-146. Academic Press Inc., New York.
17. Gray A.P. Design and structure activity relationship of antidotes to organophosphorus anticholinesterase agents. Drug Metabolism Reviews 1984, 15:557-589.
18. Hegedorn I., Stark I., Lorenz H.P. Reactivation of phosphorylated acetylcholinesterase-dependence upon activator acidity. Angewandte Chemie International Edition in English 1972, 11:307-309.
19. Krejcova G., Kassa J. Neuroprotective efficacy of pharmacological pretreatment and antidotal treatment in tabun-poisoned rats. Toxicology 2003, 185:129-139.
20. Kuca K., Cabal J. Reactivation of cyclosarin-inhibited acetylcholinesterase. Chemicke Listy 2002, 11:951.
21. Kuca K., Jun D., Musilek K. Structural requirements of acetylcholinesterase reactivators. Mini Reviews in Medicinal Chemistry 2006, 6(3):269-277.
22. Kuca K., Bielavsky J., Cabal J., Kassa J. Synthesis of a new reactivator of tabun-inhibited acetylcholinesterase. Bioorganic and Medicinal Chemistry Letters 2003, 13:3545-3547.
23. Leadbeater L., Inns R.H., Rylands J.M. Treatment of poisoning by soman. Fundamental and Applied Toxicology 1985, 5:S225-S231.
24. MacIlwain C. Study proves Iraq used nerve gas. Nature 1993, 363:3.
25. 2-terminal and active centre sequences. The Journal of Biological Chemistry 1985, 260:12185-12189.
26. Musilek K., Kuca K., Jun D., Dehnal V., Dolezal M. Synthesis of the novel series of bispyridinium compounds bearing (E)-but-2-ene linker and evaluation of their reactivation activity against chloropyrifos-inhibited acetylcholinesterase. Bioorganic and Medicinal Chemistry Letters 2006, 16:662.
27. Musilek K., Kuca K., Dolezal M. Progress in synthesis of new acetylcholinesterase reactivators during the period 1990-2004. Current Organic Chemistry 2007, 11:229-238.
28. Nagao M., Takatori T., Matsuda Y., Nakajima M., Iwase H., Iwadate K. Definitive evidence for the acute sarin poisoning diagnosis in the Tokyo subway. Toxicology and Applied Pharmacology 1997, 144:198-203.
29. Odzak R., Calic M., Hrenar T., Primozic I., Kovarik Z. Evaluation of monoquaternary pyridinium oximes potency to reactivate tabun-inhibited human acetylcholinesterase. Toxicology 2007, 233:85-96.
30. Okumura T., Hisaoka T., Yamada A., Naito T., Isonuma H., Okumura S., Miura K., Sakurada M., Maekawa H., Ishimatsu S., Takasu N., Suzuki K. Toxicology and Applied Pharmacology 2005, 207:471-476.
31. Pang Y.P., Kollmeyer T.M., Hong F., Lee J.C., Hammond P.I., Haugabouk S.P., Brimijoin S. Rational design of alkylene-linked bis-pyridiniumaldoximes as improved acetylcholinesterase reactivators. Chemistry and Biology 2003, 10:491-502.
32. Rao C.S., Venkateswahlu V., Achaiah G. Quaternary salts of 4,3' and 4,4' bis-pyridinium monooximes. Part 2: synthesis and biological activity. Bioorganic and Medicinal Chemistry Letters 2006, 16:2134-2138.
33. Shafferman A., Ordentlich A., Barak D., Stein D., Ariel N., Velan B. Aging of phosphylated human acetylcholinesterase: catalytic processes mediated by aromatic and polar residues of the active centre. Biochemistry Journal 1996, 318:833-840.
34. Sinko G., Calic M., Kovarik Z. Para- and ortho-pyridinium aldoximes in reaction with acetylthiocholine. FEBS Letters 2006, 580:3167.
35. Stern E.S., Timmons C.J. Gillam and Stern's: Introduction to Electronic Absorption Spectroscopy in Organic Chemistry 1970, Edward Arnold Ltd., London, p. 149.
36. Volans A.P. Sarin: guidelines on the management of vicuims of a nerve gas attack. Journal of accident and Emergency Medicine 1996, 13:202-206.
37. Worek F., Reiter G., Eyer P., Szinicz L. Reactivation kinetics of acetylcholinesterase from different species inhibited by highly toxic organophosphates. Archives of Toxicology 2002, 76:523-529.