Pseudo-catalytic scavenging: Searching for a suitable reactivator of phosphorylated butyrylcholinesterase

Chemico-Biological Interactions

Volumn 187, Issue 1-3, 2010, Pages 167-171

  Kovarik, Zrinka ^a   Katalinić, Maja ^a   Šinko, Goran ^a   Binder, Jiri ^b   Holas, Ondrej ^b   Jung, Young Sik ^c   Musilova, Lucie ^b   Jun, Daniel ^d,e,f   Kuča, Kamil ^d,e  

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

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

^c Korea Research Institute of Chemical Technology   (South Korea)

^d UNIVERSITY OF DEFENCE   (Czech Republic)

^e UNIVERSITY OF DEFENCE   (Czech Republic)

^f CZECH UNIVERSITY OF LIFE SCIENCES PRAGUE   (Czech Republic)

Author keywords

Bioscavenger; Cholinesterase; Molecular modelling; Paraoxon; Reactivation; Tabun

Indexed keywords

1 (4 HYDROXYIMINOMETHYLPYRIDINIUM) 3 (4 CARBAMOYLPYRIDINIUM)PROPANE BROMIDE; 1,1' (BUT 2 ENE 1,4 DIYL)BIS[4 (HYDROXYIMINOMETHYLPYRIDINIUM)BROMIDE]; 1,1' (BUTANE 1,4 DIYL)BIS[4 (HYDROXYIMINOMETHYL)PYRIDINIUM]BROMIDE; 1,1' [2,2' OXYBIS(ETHANE 2,1 DIYL)]BIS(4 HYDROXYIMINOMETHYLPYRIDINIUM)BROMIDE; 3 (N' HYDROXYCARBAMIMIDOYL) 1 [4 [4 [(HYDROXYIMINO)METHYL]PYRIDINIUM 1 YL]BUT 2 ENYL]PYRIDINIUM BROMIDE; 3 CARBAMOYL 1 [4 [4 [(HYDROXYIMINO)METHYL]PYRIDINIUM 1 YL]BUT 2 ENYL]PYRIDINIUM BROMIDE; 4 CARBAMOYL 1 [2 [2 [4 (HYDROXYIMINOMETHYL)PYRIDINIUM 1 YL]ETHOXY]ETHYL]PYRIDINIUM BROMIDE; 4 CARBAMOYL 1 [4 [4 [(HYDROXYIMINO)METHYL]PYRIDINIUM 1 YL]BUT 2 ENYL]PYRIDINIUM BROMIDE; BIS(PYRIDINIUM OXIME) DERIVATIVE; CHOLINESTERASE; K 027; K 074; K 075; K 117; K 127; K 203; K 269; OBIDOXIME; PARAOXON; TABUN; TIPINDOLE METHIODIDE; TRIMEDOXIME; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHOLINESTERASE INHIBITION; CONTROLLED STUDY; DRUG POTENCY; DRUG STRUCTURE; ENZYME REACTIVATION; IN VITRO STUDY; MOLECULAR DOCKING;

EID: 77955516543     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2010.02.023     Document Type: Article

References (22)

1. Thiermann H., Szinicz L., Eyer F., Worek F., Eyer P., Felgenhauer N., Zilker T. Modern strategies in therapy of organophosphate poisoning. Toxicol. Lett. 1999, 107:233-239.
2. Lenz D.E., Yeung D., Smith J.R., Sweeney R.E., Lumley L.A., Cerasoli D.M. Stoichiometric and catalytic scavengers as protection against nerve agent toxicity: A mini review. Toxicology 2007, 233:31-39.
3. Taylor P., Kovarik Z., Reiner E., Radić Z. Acetylcholinesterase: converting a vulnerable target to a template for antidotes and detection of inhibitor exposure. Toxicology 2007, 233:70-78.
4. Masson P., Nachon F., Broomfield C.A., Lenz D.E., Verdier L., Schopfer L.M., Lockridge O. A collaborative endeavour to design cholinesterase-based catalytic scavengers against toxic organophosphorus esters. Chem. Biol. Interact. 2008, 175:273-280.
5. Cerasoli D.M., Griffiths E.M., Doctor B.P., Saxena A., Fedorko J.M., Greig N.H., Yu Q.S., Huang Y., Wilgus H., Karatzas C.N., Koplovitz I., Lenz D.E. In vitro and in vivo characterization of recombinant human butyrylcholinesterase (Protexia) as a potential nerve agent bioscavenger. Chem. Biol. Interact. 2005, 157-158:363-365.
6. Kovarik Z., Radić Z., Berman H.A., Taylor P. Mutation of acetylcholinesterase to enhance oxime-assisted catalytic turnover of methylphosphonates. Toxicology 2007, 233:79-84.
7. Ellman G.L., Courtney K.D., Andres V., Featherstone R.M. New and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 1961, 7:88-95.
8. Čalić M., Lucić Vrdoljak A., Radić B., Jelić D., Jun D., Kuča K., 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 2006, 219:85-96.
9. Kovarik Z., Čalić M., Bosak A., Šinko G., Jelić D. In vitro evaluation of aldoxime interactions with human acetylcholinesterase. Croat. Chem. Acta 2008, 81:47-57.
10. Carletti E., Li H., Li B., Ekström F., Nicolet Y., Loiodice M., Gillon E., Froment M.T., Lockridge O., Schopfer L.M., Masson P., Nachon F. Aging of cholinesterases Phosphorylated by tabun proceeds through O-dealkylation. J. Am. Chem. Soc. 2008, 130:16011-16020.
11. Ekström F.J., Astot C., Pang Y.P. Novel nerve-agent antidote design based on crystallographic and mass spectrometric analyses of tabun-conjugated acetylcholinesterase in complex with antidotes. Clin. Pharmacol. Ther. 2007, 82:282-293.
12. Aurbek N., Thiermann H., Eyer F., Eyer P., Worek F. Suitability of human butyrylcholinesterase as therapeutic marker and pseudo catalytic scavenger in organophosphate poisoning: A kinetic analysis. Toxicology 2009, 259:133-139.
13. Lucić Vrdoljak A., Čalić M., Radić B., Berend S., Jun D., Kuča K., Kovarik Z. Pretreatment with pyridinium oximes improves antidotal therapy against tabun poisoning. Toxicology 2006, 228:41-50.
14. Čalić M., Bosak A., Kuča K., Kovarik Z. Interactions of butane, but-2-ene or xylene-like linked bispyridinium para-aldoximes with native and tabun-inhibited human cholinesterases. Chem. Biol. Interact. 2008, 175:305-308.
15. Kovarik Z., Lucić Vrdoljak A., Berend S., Čalić M., Kuča K., Musilek K., Radić B. Evaluation of oxime K203 as antidote in tabun poisoning. Arh. Hig. Rada Toksikol. 2009, 60:19-26.
16. Luo C., Saxena A., Ashani Y., Leader H., Radić Z., Taylor P., Doctor B.P. Role of edrophonium in prevention of the re-inhibition of acetylcholinesterase by phosphorylated oxime. Chem. Biol. Interact. 1999, 119-120:129-135.
17. Ashani Y., Bhattacharjee A.K., Leader H., Saxena A., Doctor B.P. Inhibition of cholinesterases with cationic phosphonyl oximes highlights distinctive properties of the charged pyridine groups of quaternary oxime reactivators. Biochem. Pharmacol. 2003, 66:191-202.
18. Ashani Y., Radić Z., Tsigelny I., Vellom D.C., Pickering N.A., Quinn D.M., Doctor B.P., Taylor P. Amino acid residues controlling reactivation of organophophonyl conjugates of acetylcholinesterase by mono- and bisquaternary oximes. J. Biol. Chem. 1995, 270:6370-6380.
19. Jun D., Musilova L., Kuca K., Kassa J., Bajgar J. Potency of several oximes to reactivate human acetylcholinesterase and butyrylcholinesterase inhibited by paraoxon in vitro. Chem. Biol. Interact. 2008, 175:421-424.
20. Carletti E., Aurbek N., Gillon E., Loiodice M., Nicolet Y., Fontecilla-Camps J.-C., Masson P., Thiermann H., Nachon F., Worek F. Structure-activity analysis of aging and reactivation of human butyrylcholinesterase inhibited by analogues of tabun. Biochem. J. 2009, 421:97-106.
21. Kovarik Z., Radić Z., Grgas B., Škrinjarić-Špoljar M., Reiner E., Simeon-Rudolf V. Amino acid residues involved in the interaction of acetylcholinesterase and butyrylcholinesterase with the carbamates Ro 02-0683 and bambuterol, and with terbutaline. BBA-Protein Struct. M 1999, 1433:261-271.
22. Katalinić M., Rusak G., Domaćinović Barović J., Šinko G., Jelić D., Antolović R., Kovarik Z. Structural aspects of flavonoids as inhibitors of human butyrylcholinesterase. Eur. J. Med. Chem. 2010, 45:186-192.