Comparison of polyethylene glycol-conjugated recombinant human acetylcholinesterase and serum human butyrylcholinesterase as bioscavengers of organophosphate compounds

Molecular Pharmacology

Volumn 70, Issue 3, 2006, Pages 1121-1131

  Cohen, Ofer ^a   Kronman, Chanoch ^a   Raveh, Lily ^a   Mazor, Ohad ^a   Ordentlich, Arie ^a   Shafferman, Avigdor ^a  

^a ISRAEL INSTITUTE FOR BIOLOGICAL RESEARCH   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLINESTERASE; CHOLINESTERASE REACTIVATOR; MACROGOL DERIVATIVE; ORGANOPHOSPHATE; RECOMBINANT ENZYME; RECOMBINANT HUMAN ACETYLCHOLINESTERASE; SARIN; SCAVENGER; SOMAN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CELL PROTECTION; CELL STRAIN HEK293; CELL SURVIVAL; DRUG ACTIVITY; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG DISTRIBUTION; DRUG EFFICACY; DRUG INTOXICATION; ENANTIOMER; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; LETHAL DOSE; MONKEY; MOUSE; NONHUMAN; PRIORITY JOURNAL; STEREOCHEMISTRY; TITRIMETRY;

ACETYLCHOLINESTERASE; ANIMALS; BINDING SITES; BUTYRYLCHOLINESTERASE; HUMANS; LETHAL DOSE 50; MALE; MICE; ORGANOPHOSPHORUS COMPOUNDS; ORGANOTHIOPHOSPHORUS COMPOUNDS; POLYETHYLENE GLYCOLS; RECOMBINANT PROTEINS; SARIN; SOMAN; SURVIVAL ANALYSIS; TISSUE DISTRIBUTION;

EID: 33747617345     PISSN: 0026895X     EISSN: 15210111     Source Type: Journal    
DOI: 10.1124/mol.106.026179     Document Type: Article

References (40)

1. Ashani Y, Grauer E, Grunwald J, Allon N, and Raveh L (1998) Current capabilities in extrapolating from animal to human the capacity of human butyrylcholinesterase to detoxify organophosphates, in Structure and Function of Cholinesterases and Related Proteins (Doctor BP, Quinn DM, Rotundo RL, and Taylor P eds) pp 255-260, Plenum Press, New York.
2. Benschop HP and de Jong LPA (1988) Nerve agent stereoisomers: analysis, isolation and toxicology. Acc Chem Res 21:368-374.
3. Benschop HP and de Jong LPA (1991) Toxicokinetics of soman: species variation and stereospecificity in elimination pathways. Neurosci Biobehav Rev 15:73-77.
4. Benschop HP, Konings CAG, Van Genderen J, and de Jong LPA (1984) Isolation, anticholinesterase properties, and acute toxicity in mice of the four stereoisomers of the nerve agent soman. Toxicol Appl Pharmacol 72:61-74.
5. Chitlaru T, Kronman C, Velan B, and Shafferman A (2001) Effect of human acetylcholinesterase subunit assembly on its circulatory residence. Biochem J 354:613-625.
6. Chitlaru T, Kronman C, Velan B, and Shafferman A (2002) Overloading and removal of N-glycosylation targets on human acetylcholinesterase: effects on glycan composition and circulatory residence time. Biochem J 363:619-631.
7. Chitlaru T, Kronman C, Zeevi M, Kam M, Harel A, Ordentlich A, Velan B, and Shafferman A (1998) Modulation of circulatory residence of recombinant acetylcholinesterase through biochemical or genetic manipulation of sialylation levels. Biochem J 336:647-658.
8. Chilukuri N, Parikh K, Sun W, Naik R, Tipparaju P, Doctor BP, and Saxena A (2005) Polyethylene glycosylation prolongs the circulatory stability of recombinant human butyrylcholinesterase. Chem Biol Interact 157-158:115-121.
9. Clement JG (1984) Importance of aliesterase as a detoxification mechanism for soman (pinacolyl methylphosphonofluoridate) in mice. Biochem Pharmacol 33:3807-3811.
10. Cohen O, Kronman C, Chitlaru T, Ordentlich A, Velan B, and Shafferman A (2001) Effect of chemical modification of recombinant human acetylcholinesterase by polyethylene glycol on its circulatory longevity. Biochem J 357:795-802.
11. Cohen O, Kronman C, Velan B, and Shafferman A (2004) Amino acid domains control the circulatory residence time of primate acetylcholinesterases in rhesus macaques. Biochem J 378:117-128.
12. De Bisschop HCJV, Michiels KW, Vlaminck LBC, Vansteenkiste SO, and Schacht EH (1991) Phosphonylation of purified human canine and porcine cholinesterase by soman. Biochem Pharmacol 41:955-959.
13. de Jong LPA, Van Dijk C, and Benschop HP (1988) Hydrolysis of the four stereoisomers of soman catalyzed by liver homogenate and plasma from rat, guinea pig and marmoset and by human plasma. Biochem Pharmacol 37:2939-2948.
14. Duysen EG, Bartles CF, and Lockridge O (2002) Wild-type and A328W mutant human butyrylcholinesterase tetramers expressed in Chinese hamster ovary cells have a 16-h half-life in the circulation and protect mice from cocaine toxicity. J Pharmacol Exp Ther 302:751-758.
15. Ellman GL, Courtney KD, Andres V, and Featherstone RM (1961) A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 7:88-95.
16. Eto M, Casida JE, and Eto T (1962) Hydroxylation and cyclization reactions involved in the metabolism of tri-o-cresyl phosphate. Biochem Pharmacol 11:337-352.
17. Finney DJ (1964) The Spearman-Karber method, in Statistical Methods in Biological Assay, pp 524-530, Charles Griffin, London.
18. Fischer M, Ittah A, Liefer I, and Gorecki M (1993) Expression and reconstitution of biologically active human acetylcholinesterase from E. coli. Cell Mol Neurobiol 13:25-38.
19. Harris JM and Chess RB (2003) Effect of PEGylation on pharmaceuticals. Nat Rev Drug Discov 2:214-221.
20. Kronman C, Velan B, Gozes Y, Leitner M, Flashner Y, Lazar A, Marcus D, Sery T, Grosfeld H, Cohen S, et al. (1992) Production and secretion of high levels of recombinant human acetylcholine esterase in cultured cell lines: microheterogeneity of the catalytic subunit. Gene 121:295-304.
21. Jimmerson VR, Shih TM, and Mailman RB (1989) Variability in soman toxicity in the rat: correlation with biochemical and behavioral measures. Toxicology 57:241-254.
22. Kronman C, Velan B, Marcus D, Ordentlich A, Reuveny S, and Shafferman A (1995) Involvement of oligomerization, N-glycosylation and sialylation in the clearance of cholinesterases from circulation. Biochem J 311:959-967.
23. Kronman C, Chitlaru T, Elhanay E, Velan B, and Shafferman A (2000) Hierarchy of post-translational modifications involved in the circulatory longevity of glycoproteins. J Biol Chem 275:29488-29502.
24. Lenz DE, Maxwell DM, Koplovits I, Clark CR, Capacio BR, Cerasoli DM, Federko JM, Luo C, Saxena A, Doctor BP, et al. (2005) Protection against soman or VX poisoning by human butyrylcholinesterse in guinea pigs and cynomolgus monkeys. Chem Biol Interact 157-158:205-210.
25. Levy D and Ashani Y (1986) Synthesis and in vitro properties of a powerful quaternary methylphosphonate inhibitor of acetylcholinesterase. A new marker in blood-brain barrier research. Biochem Pharmacol 35:1079-1085.
26. Li B, Sedlacek M, Manoharan I, Boopathy R, Duysen EG, Masson P, and Lockridge O (2005) Butyrylcholinesterase, paraoxonase and albumin esterase, but not carboxylesterase, are present in human plasma. Biochem Pharmacol 70:1673-1684.
27. Li B, Stribley JA, Ticu A, Xie W, Schopfer LM, Hammond P, Brimijoin S, Hinrichs SH, and Lockridge O (2000) Abundant tissue butyrylcholinesterase and its possible function in the acetylcholinesterase knockout mouse. J Neurochem 75:1320-1331.
28. Massoulie J, Bon S, Perrier N, and Falasca C (2005) The C-terminal peptides of acetylcholinesterase: cellular trafficking, oligomerization and functional anchoring. Chem Biol Interact 157-158:3-14.
29. Maxwell DM (1992) The specificity of carboxylesterase protection against the toxicity of organophosphorous compounds. Toxicol Appl Pharmacol 114:306-312.
30. Maxwell DM, Brecht KM, and O'Neill BL (1987) The effect of carboxylesterase inhibition on interspecies differences in soman toxicity. Toxicol Lett 39:35-42.
31. Millard CB, Lockridge O, and Broomfield CA (1998) Organophosphorus acid anhydride hydrolase activity in human butyrylcholinesterase: synergy results in a somanase. Biochemistry 37:237-247.
32. Ordentlich A, Barak D, Kronman C, Ariel N, Segall Y, Velan B, and Shafferman A (1996) The architecture of human acetylcholinesterase active center probed by interactions with selected organophosphate inhibitors. J Biol Chem 271:11953-11962.
33. Ordentlich A, Barak D, Kronman C, Benschop HP, de Jong LPA, Ariel N, Barak R, Segall Y, Velan B, and Shafferman A (1999) Exploring the active center of human acetylcholinesterase with stereomers of an organophosphorus inhibitor with two chiral centers. Biochemistry 38:3055-3066.
34. Ordentlich A, Barak D, Sod-Moriah G, Kaplan D, Mizrahi D, Segall Y, Kronman C, Karton Y, Lazar A, Marcus D, et al. (2004) Stereoselectivity toward VX is determined by interactions with residues of the acyl pocket as well as of the peripheral anionic site of AChE. Biochemistry 43:11255-11265.
35. Raveh L, Grauer E, Grunewald J, Cohen E, and Ashani Y (1997) The stoichiometry of protection against soman and VX toxicity in monkeys pretreated with human butyrylcholinesterase. Toxicol Appl Pharmacol 145:43-53.
36. Raveh L, Grunwald J, Marcus D, Papier Y, Cohen E, and Ashani Y (1993) Human butyrylcholinesterase as a general prophylactic antidote for nerve agent toxicity. Biochem Pharmacol 45:37-41.
37. Saxena A, Ashani Y, Raveh L, Stevenson D, Patel T, and Doctor BP (1998) Role of oligosaccharides in the pharmacokinetics of tissue-derived and genetically engineered cholinesterases. Mol Pharmacol 53:112-122.
38. Shafferman A, Ordentlich A, Barak D, Stein D, Ariel N, and Velan B (1996) Aging of phosphylated human acetylcholinesterase: catalytic processes mediated by aromatic and polar residues of the active center. Biochem J 318:833-840.
39. Shafferman A, Velan B, Ordentlich A, Kronman C, Grosfeld H, Leitner M, Flashner Y, Cohen S, Barak D, and Ariel N (1992) Substrate inhibition of acetylcholinesterase: residues affecting signal transduction from the surface to the catalytic center. EMBO (Eur Mol Biol Organ) J 11:3561-3568.
40. 3H]-soman in mice. Arch Toxicol 64:663-668.