Structure-activity approach in the reactivation of tabun-phosphorylated human acetylcholinesterase with bispyridinium para-aldoximes

Arhiv za Higijenu Rada i Toksikologiju

Volumn 58, Issue 2, 2007, Pages 201-209

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

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

Author keywords

Antidotes; Nerve agents; Organophosphorus compounds

Indexed keywords

1,1' METHYLENEBIS(4 HYDROXYIMINOMETHYLPYRIDINIUM) DICHLORIDE; ACETYLCHOLINESTERASE; ALDOXIME; BISPYRIDINIUM 4 ALDOXIME DERIVATIVE; DMB 4; N,N' (ETHANO)BIS(4 HYDROXYIMINOMETHYL)PYRIDINIUM METHANOSULPHONATE; TABUN; TRIMEDOXIME; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CONTROLLED STUDY; DISSOCIATION CONSTANT; DRUG CONFORMATION; DRUG PROTEIN BINDING; ENZYME ACTIVE SITE; ENZYME INACTIVATION; ENZYME INHIBITION; ENZYME PHOSPHORYLATION; ENZYME REACTIVATION; ERYTHROCYTE; HUMAN; HUMAN CELL; STRUCTURE ACTIVITY RELATION;

ACETYLCHOLINESTERASE; CHEMICAL WARFARE AGENTS; CHOLINESTERASE INHIBITORS; CHOLINESTERASE REACTIVATORS; ENZYME ACTIVATION; ERYTHROCYTES; HUMANS; OXIMES; PHOSPHORIC ACID ESTERS; PHOSPHORYLATION; STRUCTURE-ACTIVITY RELATIONSHIP; TRIMEDOXIME;

EID: 34250375666     PISSN: 00041254     EISSN: None     Source Type: Journal    
DOI: 10.2478/v10004-007-0013-7     Document Type: Article

References (25)

1. Gray AP. Design and structure-activity relationships of antidotes to organophosphorus anticholinesterase agents. Drug Metab Rev 1984;15, 557-89.
2. Stojiljković MP, Jokanovic M. Pyridinium oximes: rationale for their selection as causal antidotes against organophosphate poisonings and current solutions for auto-injectors. Arh Hig Rada Toksikol 2006;57:435-43.
3. Čalić M, Lucić Vrdoljak A, Radić B, Jelić D, Jun D, Kuča K, Kovarik Z. In vitro and in vivo evaluation of pyridinium aldoximes: mode of interaction with acetylcholinesterase, effect on tabun- and somanpoisoned mice and their cytotoxicity. Toxicology 2006;219:85-96.
4. Lucić Vrdoljak A, Čalić M, Radić B, Berend S, Jun D, Kuča K, Kovarik Z. Pretreatment with pyridinium aldoximes improves antidotal therapy against tabun poisoning. Toxicology 2006;228:41-50.
5. Simeon-Rudolf V, Reiner E, Škrinjarić-Špoljar M, Radić B, Lucić A, Primožič I, Tomić S. Quinuclidinium-imidazolium compounds: synthesis, mode of interaction with acetylcholinesterase and effect upon soman intoxicated mice. Arch Toxicol 1998;72:289-95.
6. Škrinjarić-Špoljar M, Burger N, Lovrić J. Inhibition of acetylcholinesterase by three new pyridinium compounds and their effect on phosphonylation of the enzyme. J Enzym Inhib 1999;14:331-41.
7. Kovarik Z, Bosak A, Šinko G, Latas T. Exploring active sites of cholinesterases by inhibition with bambuterol and haloxon. Croat Chem Acta 2003;76:63-7.
8. Šinko G, Bosak A, Kovarik Z, Simeon-Rudolf V. Structure-inhibition relationships in the interaction of butyrylcholinesterase with bambuterol, haloxon and their leaving groups. Chem-Biol Interact 2005;157-158:421-3.
9. Ellman GL, Courtney KD, Andres VJr, Featherstone RM. New and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1961;7:88-95.
10. Eyer P, Worek F, Kiderlen D, Šinko G, Štuglin A, Simeon-Rudolf V, Reiner E. Molar absorption coefficients for the reduced Ellman reagent: reassessment. Anal Biochem 2003;312:224-7.
11. Šinko G, Čalić M, Kovarik Z. para- and ortho-Pyridinium aldoximes in reaction with acetylthiocholine. FEBS Lett 2006;580:3167-72.
12. Odžak R, Čalić M, Hrenar T, Primožič I, Kovarik Z. Evaluation of monoquaternary pyridinium aldoximes potency to reactivate tabun-inhibited human acetylcholinesterase. Toxicology 2006;233:85-96.
13. Kovarik Z, Radić Z, Berman HA, Simeon-Rudolf V, Reiner E, Taylor P. Mutant cholinesterases possessing enhanced capacity for reactivation of their phosphonylated conjugates. Biochemistry 2004;43:3222-9.
14. Heilbronn E. In vitro reactivation and "aging" of tabun-inhibited blood cholinesterases studied with N-methyl-pyridinium-2- aldoxime methane sulphonate and N,N′-trimethylene bis (pyridinium-4- aldoxime) dibromide. Biochem Pharmacol 1963;12:25-36.
15. Ashani Y, Bhattacharjee AK, Leader H, Saxena A, Doctor BP. Inhibition of cholinesterase with cationic phosphonyl oximes highlights distinctive properties of the charged pyridine groups of quaternary oxime reactivators. Biochem Pharmacol 2003;33:191-202.
16. Francisković L, Škrinjarić-Špoljar M, Reiner E. Interaction of imidazolium and pyridinium dioximes with human erythrocyte acetylcholinesterase. Chem-Biol Interact 1993;87:323-8.
17. Kuča K, Patočka J, Cabal J. Reactivation of organophosphate inhibited acetylcholinesterase activity by α, ω-bis- (hydroxyiminomethylpyridinium)alkanes in vitro. J Appl Biomed 2003;1:207-11.
18. Worek F, Thiermann H, Szinicz L, Eyer P. Kinetic analysis of interactions between human acetylcholineserase, structurally different organophosphorous compounds and aldoximes. Biochem Pharmacol 2004;68:2237-48.
19. Pang Y-P, Kollmeyer TM, Hong F, Lee J, Hammond PI, Haugabouk SP, Brimijoin S. Rational design of alkylene-linked bis-pyridiniumaldoximes as improved acetylcholinesterase reactivators. Chem Biol 2003;10:491-502.
20. Ekström F, Pang Y-P, Boman M, Artursson E, Akfur C, Börjegren S. Crystal structures of acetylcholinesterase in complex with HI-6, Ortho-7 and obidoxime: Structural basis for differences in the ability to reactivate tabun conjugates. Biochem Pharmacol 2006;72:597-607.
21. Bosak A, Primožič I, Oršulić M, Tomić S, Simeon-Rudolf V. Enantiomers of quinuclidin-3-ol derivates: resolution and interactions with human cholinesterases. Croat Chem Acta 2005;78:121-8.
22. Simeon V, Radić Z, Reiner E. Inhibition of cholinesterase by the aldoximes P2AM and toxogonin. Croat Chem Acta 1981;54:473-80.
23. Škrinjarić-Špoljar M, Simeon V, Reiner E, Krauthacker B. Bispyridinium compounds: inhibition of human erythrocyte acetylcholinesterase and protection of the enzyme against phosphylation. Acta Pharm Jugosl 1988;38:101-9.
24. Kovarik Z, Ciban N, Radić Z, Simeon-Rudolf V, Taylor P. Active site mutant acetylcholinesterase interactions with 2-PAM, HI-6, and DDVR Biochem Biophys Res Commun 2006;342:973-8.
25. Reiner E. Inhibition of acetylcholinesterase by 4,4′-bipyridine and its effect upon phosphylation of the enzyme. Croat Chem Acta 1986;59:925-31.