A common mechanism for resistance to oxime reactivation of acetylcholinesterase inhibited by organophosphorus compounds

Chemico-Biological Interactions

Volumn 203, Issue 1, 2013, Pages 72-76

  Maxwell, Donald M ^a   Brecht, Karen M ^a   Sweeney, Richard E ^a  

^a US ARMY MEDICAL RESEARCH INSTITUTE OF CHEMICAL DEFENSE   (United States)

Author keywords

Acetylcholinesterase; Organophosphorus; Oxime; Reactivation; Structure activity

Indexed keywords

1 (4 CARBAMOYLPYRIDINIO) 1' (2 HYDROXYIMINOMETHYLPYRIDINIO)DIMETHYL ETHER; ACETYLCHOLINESTERASE; CYCLOSARIN; METHYLPHOSPHONOTHIOIC ACID S (2 DIISOPROPYLAMINOETHYL) O ETHYL ESTER; O ETHYLISOPROPYLPHOSPHONOFLUORIDATE; O METHYLCYCLOHEXYLPHOSPHONOFLUORIDATE; O METHYLISOPROPYLPHOSPHONOFLUORIDATE; OBIDOXIME; ORGANOPHOSPHORUS COMPOUND; RECOMBINANT ENZYME; SARIN; TABUN; UNCLASSIFIED DRUG;

ANIMAL CELL; CHOLINESTERASE INHIBITION; CONFERENCE PAPER; CONTROLLED STUDY; DRUG RESISTANCE; DRUG SPECIFICITY; ENZYME REACTIVATION; NONHUMAN; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ACETYLCHOLINESTERASE; CHOLINESTERASE INHIBITORS; CHOLINESTERASE REACTIVATORS; GPI-LINKED PROTEINS; HUMANS; KINETICS; OBIDOXIME CHLORIDE; ORGANOPHOSPHORUS COMPOUNDS; OXIMES; PYRIDINIUM COMPOUNDS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RECOMBINANT PROTEINS; SARIN;

EID: 84875806551     PISSN: 00092797     EISSN: 18727786     Source Type: Journal    
DOI: 10.1016/j.cbi.2012.08.024     Document Type: Conference Paper

References (20)

1. T.C. Marrs Clinical and Experimental Toxicology of Organophosphates and Carbamates 1992 Butterworth & Heinemann Oxford pp. 555-577
2. P. Taylor Anticholinesterase agents L.L. Brunton, J.S. Lazo, K.L. Parker, Goodman & Gilman's Pharmacological Basis of Therapeutics 2006 McGraw-Hill New York 201 216
3. F. Worek, H. Thiermann, L. Szinicz, and P. Eyer Kinetic analysis of interactions between human acetylcholinesterase, structurally different organophosphorus compounds and oximes Biochem. Pharmacol. 68 2004 2237 2248
4. F. Worek, N. Aurbek, M. Koller, C. Becker, P. Eyer, and H. Thiermann Kinetic analysis of reactivation and aging of human acetylcholinesterase inhibited by different phosphoramidates Biochem. Pharmacol. 73 2007 1807 1817
5. A. Bartling, F. Worek, L. Szinicz, and H. Thiermann Enzyme-kinetic investigations of different sarin analogues reacting with human acetylcholinesterase and butyrylcholinesterase Toxicology 233 2007 166 172
6. F. Worek, P. Eyer, N. Aurbek, L. Szinicz, and H. Thiermann Recent advances in evaluation of oxime efficacy in nerve agent poisoning by in vitro analysis Toxicol. Appl. Pharmacol. 219 2007 226 234
7. A. Ashani, Z. Radic, I. Tsigelny, D.C. Vellom, N.A. Pickering, D.M. Quinn, B.P. Doctor, and P. Taylor Amino acid residues controlling reactivation of organophosphonyl conjugates of acetylcholinesterase by mono- and bisquaternary oximes J. Biol. Chem. 270 1995 6370 6380
8. L. Wong, Z. Radic, R.J. Bruggemann, N. Hosea, H.A. Berman, and P. Taylor Mechanism of oxime reactivation of acetylcholinesterase analyzed by chirality and mutagenesis Biochemistry 39 2000 5750 5757
9. K. Kuca, D. Jun, and K. Musilek Structural requirements of acetylcholinesterase reactivators Mini Rev. Med. Chem. 6 2006 269 277
10. Y.P. Pang, T.M. Kollmeyer, F. Hong, J.-C. Lee, P.I. Hammond, S.P. Haugabouk, and S. Brimijoin Rational design of alkylene-linked bis-pyridiniumaldoximes as improved acetylcholinesterase reactivators Chem. Biol. 10 2003 2003 491 502
11. G.I. Ellman, K.D. Courtney, V. Andres, and R.M. Featherstone A new and rapid colorimetric determination of acetylcholinesterase activity Biochem. Pharmacol. 7 1961 88 95
12. ph in the chemistry of organophosphorus compounds Russ. Chem. Rev. 38 1969 795 811
13. M.L. Connolly Computation of molecular volume J. Am. Chem. Soc. 107 1985 1118 1124
14. C.B. Millard, G. Koellner, A. Ordentlich, A. Shafferman, I. Silman, and J.L. Sussman Reaction products of acetylcholinesterase and VX reveal a mobile histidine in the catalytic triad J. Am. Chem. Soc. 121 1999 9883 9884
15. A. Hornberg, A.K. Tunemalm, and F. Ekstrom Crystal structures of acetylcholinesterase in complex with organophosphorus compounds suggest that the acyl pocket modulates the aging reaction by precluding the formation of the trigonal bipyramidal transition state Biochemistry 46 2007 4815 4825
16. F. Ekstrom, C. Akfur, A.K. Tunemalm, and S. Lundberg Structural changes of phenylalanine 338 and histidine 447 revealed by the crystal structures of tabun-inhibited murine acetylcholinesterase Biochemistry 45 2006 74 81
17. Y. Ashani, A.K. Bhattacharjee, H. Leader, A. Saxena, and B.P. Doctor Inhibition of cholinesterases with cationic phosphonyl oximes highlights distinctive properties of the charged pyridine groups of quaternary oxime reactivators Biochem. Pharmacol. 66 2003 191 202
18. C. Luo, Y. Ashani, and B.P. Doctor Acceleration of oxime-induced reactivation of organophosphate-inhibited fetal bovine serum acetylcholinesterase by monoquaternary and bisquaternary ligands Mol. Pharmacol. 55 1998 718 726
19. Z. Kovarik, Z. Radic, H.A. Berman, V. Simeon-Rudolf, E. Reiner, and P. Taylor Acetylcholinesterase active centre and gorge conformations analyzed by combinatorial mutations and enantiomeric phosphonates Biochem. J. 373 2003 33 40
20. Z. Kovarik, Z. Radic, H.A. Berman, V. Simeon-Rudolf, E. Reiner, and P. Taylor Mutant cholinesterases possessing enhanced capacity for reactivation of their phosphonylated conjugates Biochemistry 43 2004 3222 3229