Acceleration of oxime-induced reactivation of organophosphate-inhibited fetal bovine serum acetylcholinesterase by monoquaternary and bisquaternary ligands

Molecular Pharmacology

Volumn 53, Issue 4, 1998, Pages 718-726

  Luo, Chunyuan ^a,b   Ashani, Yacov ^c   Doctor, Bhupendra P ^b  

^a Beijing Institute of Toxicology and Pharmacology   (China)

^b WALTER REED ARMY INSTITUTE OF RESEARCH   (United States)

^c ISRAEL INSTITUTE FOR BIOLOGICAL RESEARCH   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 HYDROXYIMINOMETHYL 1 PYRIDINIUM) 1 (4 CARBOXYAMINOPYRIDINIUM)DIMETHYL ETHER; ACETYLCHOLINESTERASE; DECAMETHONIUM; EDROPHONIUM; LIGAND; ORGANOPHOSPHATE PESTICIDE; OXIME; PROPIDIUM IODIDE; UNCLASSIFIED DRUG;

ARTICLE; CATTLE; CONJUGATE; ENZYME ASSAY; ENZYME INHIBITION; ENZYME KINETICS; ENZYME REACTIVATION; FETUS; INTOXICATION; NEUROTOXICITY; NEUROTRANSMISSION; NONHUMAN; PRIORITY JOURNAL; SERUM;

EID: 0031977239     PISSN: 0026895X     EISSN: None     Source Type: Journal    
DOI: 10.1124/mol.53.4.718     Document Type: Article

References (39)

1. Ashani Y, Gentry MK, and Doctor BP (1990) Difference in the conformational stability between native and phosphorylated acetylcholinesterase as evidenced by a monoclonal antibody. Biochemistry 29:2456-2463.
2. Ashani Y. Leader H, Rothschild N, and Dosoretz C (1998) Combined effect of organo-phosphorous hydrolase and oxime on the rate of reactivation of diethyphosphoryl- acetylcholinesterase conjugates. Biochem Pharmacol 55:159-168.
3. Ashani Y, Radić Z, Tsigelny I, Vellom DC, Pickering N, Quinn DM, Doctor BP, and Taylor P (1995) Amino acid residues controlling reactivation of organophosphonyl conjugates of acetylcholinesterase by mono- and bisquaternary oximes. J Biol Chem 270:6370-6380.
4. Barak D. Kronman C, Ordentlich A, Ariel N, Bromberg A, Marcus D, Lazar A, Velan B, and Shafferman A (1994) Acetylcholinesterase peripheral anionic site degeneracy conferred by amino acid arrays sharing a common core. J Biol Chem 264:6296-6306.
5. Barak D. Ordentlich A, Bromberg A, Kronman C, Marcus D, Lazar A, Ariel N, Velan B, and Shafferman A (1995) Allosteric modulation of acetylcholinesterase activity by peripheral ligands involves a conformational transition of the anionic subsite. Biochemistry 34:15444-15452.
6. Bencsura A, Enyedy I, and Kovach IM (1995) Origins and diversity of the aging reaction in phosphate adduct of serine hydrolase enzymes: what characteristics of the active site do they probe? Biochemistry 34:8989-8999.
7. Berman HA and Decker MM (1986a) Kinetic, equilibrium, and spectroscopic studies on dealkylation ('aging') of alkyl organophosphonyl acetylcholinesterase: electrostatic control of enzyme topography. J Biol Chem 261:10646-10652.
8. Berman HA and Decker MM (1986b) Kinetic, equilibrium, and spectroscopic studies on cation association at the active center of acetylcholinesterase: topographic distinction between trimethyl and trimethylammonium sites. Biochim Biophys Acta 872:125-133.
9. Cygler M, Schrag JD, Sussman JL, Harel M, Silman I, Gentry MK, and Doctor BP (1993) Relationship between sequence conservation and three-dimensional structure in a large family of esterases. lipases, and related proteins. Prot Sci 2:366-382.
10. De Jong LPA and Wolring GZ (1980) Reactivation of acetylcholinesterase inhibited by l,2,2′-trimethylpropyl methylphosphonofluoridate (soman) with HI-6 and related oximes. Biochem Pharmacol 29:2379-2387.
11. De La Hoz D, Doctor BP, Ralston JS, Rush RS, and Wolfe AD (1986) A simplified procedure for the purification of large quantities of fetal bovine serum acetylcholinesterase. Life Sci 39:1295-199
12. Ellman GL, Courtney KD, Andres V, and Featherstone RM (1961) A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 7:88-95.
13. Galli A, Mori F, Benini L, and Caccaiarelli N (1994) Acetylcholinesterase protection and anti-diisopropylfhiorophosphate efficacy of E2020. Eur J Pharmacol Environ Toxicol 270:189-193.
14. Gray AP (1984) Design and structure-activity relationships of antidotes to organophosphorus anticholinesterase agents. Drug Metab Rev 15:557-589.
15. Grosfeld H, Barak D, Ordentlich A, Velan B, and Shafferman A (1996) Interactions of oxime reactivators with diethylphosphoryl adducts of human acetylcholinesterases and its mutant derivatives. Mol Pharmacol 50:639-649.
16. Grubič Z and Tomazič (1989) A mechanism of action of HI-6 on soman inhibition of acetylcholinesterase in preparations of rat and human skeletal muscle; comparison to SAD-128 and PAM-2. Arch Toxicol 63:68-71.
17. Grunwald J, Raveh L, Doctor BP, and Ashani Y (1994) Huperzine A as a pretreatment candidate drug against nerve agent toxicity. Life Sci 54:991-997.
18. Harel M, Schalk L, Ehret-Sabatier L, Bouet F, Goeldner M, Hirth C, Axelsen PH, Silman I, and Sussman JL (1993) Quaternary ligand binding to aromatic residues in the active-site gorge of acetylcholinesterase. Proc Nat Acad Sci USA 90:9031-9035.
19. Hackley BE Jr, Sternberg GM, and Lamb JC (1959) Formation of potent inhibitors of AChE by reaction of pyridinaldoximes with isopropyl methylphosphonofluoridate (GB). Biochim Biophys Acta 80:211-214.
20. Harris LW, Heyl WC, Stitcher DL, and Broomfield CA (1978) Effects of 1,1′-oxydimethylene bis-(4-tert-butylpyridinium chloride) (SAD-128) and decamethonium on reactivation of soman- and sarin -inhibited cholinesterase by oximes. Biochem Pharmacol 27:757-761.
21. Harvey B, Scott RP, Sellers DJ, and Watts P (1986a) In vitro studies on the reactivation by oximes of phosphorylated acetylcholinesterase: I. On the reactions of P2S with various organophosphates and the properties of the resultant phosphorylated oximes. Biochem Pharmacol 35:737-744.
22. Harvey B, Scott RP, Sellers DJ, and Watts P (1986b) In vitro studies on the reactivation by oximes of phosphorylated acetylcholinesterase: II. On the formation of O,O-diethyl phosphorylated AChE and O-ethyl methylphosphonylated AChE and their reactivation by P2S. Biochem Pharmacol 35:745-751.
23. Kitz R and Wilson IB (1963) Acceleration of the rate of reaction of methanesulfonyl fluoride and acetylcholinesterase by substituted ammonium ions. J Biol Chem 238:745-748.
24. LeJeune KE, Frazier DS, Caranto GR, Maxwell DM, Amitai G, Russell AJ, and Doctor BP (1996) Covalent linkage of mammalian cholinesterase within polyurethane foams, in Proceedings of the 1996 Medical Defense Bioscience Review; 1996 May 12-16; Baltimore, MD. pp 223-230, U.S. Army Medical Research and Material Command.
25. Levy D and Ashani Y (1986) Synthesis and in vitro properties of a powerful quaternary methylphosphonate inhibitor of acetylcholinesterase: a new marker in the blood-brain barrier research. Biochem Pharmacol 35:1079-1085.
26. Luo C, Li Z, Xia S, Sun M, and Yang J (1995) Studies on the conformational differences in the active center of phosphorylated acetylcholinesterases. Prog Biochem Biophys (China) 22:141-146.
27. Luo C, Sun M, Yang J, and Zhu M (1994) Inhibition of affinity-purified human brain acetyl-cholinesterase by organophosphates and its reactivation. Chin J Pharmacol Toxicol 8:151-152.
28. Masson P, Froment MT, Bartels CF, and Lockridge O (1997) Importance of aspartate 70 in organophosphate inhibition, oxime reactivation and aging of human butyrylcholinesterase. Biochem J 325:53-61.
29. Ordentlich A, Barak D, Kronman C, Ariel N, Segall Y, Velan B, and Shafferman A (1995) Contribution of aromatic moieties of tyrosine 133 and of the anionic subsite tryptophan 86 to catalytic efficiency and allosteric modulation of acetylcholinesterase. J Biol Chem 270:2082-2091.
30. Radić Z, Reiner E, and Taylor P (1991) Role of the peripheral anionic site on acetylcholine-esterase: inhibition by substrate and coumarin derivatives. Mol Pharmacol 39:98-104.
31. Saxena A, Doctor BP, Maxwell DM, Lenz DE, Radie Z, and Taylor P (1993) The role of glutamate-199 in the aging of cholinesterase. Biochem Biophys Res Commun 197:343-349.
32. Saxena A, Redman AMG, Jiang X, Lockridge O, and Doctor BP (1997) Differences in the active-site gorge dimension of cholinesterases revealed by binding of inhibitor to human butyrylcholinesterase. Biochemistry 36:14642-14651.
33. Schoene K (1972) Reaktivierung von O,O-diäthylphosphoryl-acetylcholinesterase: Reaktivierungs-rephosphorylierungs-gleichgewicht. Biochem Pharmacol 21:163-170.
34. Schwarz IM, Loewenstein Y, Click D, Liao J, Norgaard-Pederson B, and Soreq H (1972) Successive organophosphate inhibition and oxime reactivation reveals distinct responses of recombinant human cholinesterase variants. Mol Brain Res 31:101-110.
35. Štale A and Šentjurc MA (1990) Contribution to the mechanism of action of SAD-128. Biochem Pharmacol 40:2511-2517.
36. Szinicz L and Hallek M (1988) Effects of some mono- and bisquaternary ammonium compounds on the reactivatability of soman-inhibited human acetylcholinesterase in vitro. Biochem Pharmacol 37:819-825.
37. Taylor P and Jacob NM (1974) Interaction of bisquaternary ammonium ligands and acetylcholinesterase: complex formation studied by fluorescent quenching. Mol Pharmacol 10:93-107.
38. Taylor P and Lappi S (1975) Interaction of fluorescence probes with acetylcholinesterase: the site and specificity of propidium. Biochemistry 14:1989-1997.
39. Wolfe AD, Chiang PK, Doctor BP, Fryar N, Rhee JP, and Saeed M (1994) Monoclonal antibody AE-2 modulates carbamate and organophosphonate inhibition of fetal bovine serum acetylcholinesterase. Mol Pharmacol 44:1152-1157.