Abstract
In 1946 there was published both the synthesis of the archetypal organophosphorus cholinesterase inhibitor, DFP,1 and the finding of an enzyme that hydrolyzes and thus detoxifies this compound.2 In 1963, in the same landmark volume to which Karczmar contributed two chapters on particular aspects of the acetylcholine system often elucidated by the use of DFP,3,4 Mounter5 reviewed the subject that has come to be known as “DFPase”. While a relationship of a compound that is an inhibitor of cholinesterase to an enzyme that hydrolyzes that compound will be self-evident, every imaginable aspect of the one enzyme is either understood or under study, whereas the other enzyme, seemingly without natural substrate or physiological role, may require some introduction.
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References
H. McCombie and B.C. Saunders, Alkyl fluorophosphonates: Preparation and physiological properties, Nature (London) 157: 287 (1946).
A. Mazur, An enzyme in animal tissue capable of hydrolyzing the phosphorus-fluorine bond of alkyl fluorophosphates, J. Biol. Chem. 164: 271 (1946).
A.G. Karczmar, Ontogenesis of cholinesterases, in: “Handbuch der Experimentellen Pharmakologie: Cholinesterases and Anticholinesterase Agents”, G.B. Koelle, ed., Springer-Verlag, Berlin (1963).
A.G. Karczmar, Ontogenetic effects, in: “Handbuch der Experimentellen Pharmakologie: Cholinesterases and Anticholinesterase Agents”, G.B. Koelle, ed., Springer-Verlag, Berlin (1963).
L.A. Mounter, Metabolism of organophosphorus agents, in: “Handbuch der Experimentellen Pharmakologie: Cholinesterases and Anticholinesterase Agents”, G.B. Koelle, ed., Springer-Verlag, Berlin (1963).
F.C.G. Hoskin, M.A. Kirkish, and K.E. Steinmann, Two enzymes for the detoxication of organophosphorus compounds - sources, similarities and significance, Fundam. Appl. Toxicol. 4: S165 (1984).
F.C.G. Hoskin, P. Rosenberg, and M. Brzin, Re-examination of the effect of DFP on electrical and cholinesterase activity of squid giant axon, Proc. Nat. Acad. Sci. USA 55: 1231 (1966).
F.C.G. Hoskin, Diisopropylphosphorofluoridate and Tabun: Enzymatic hydrolysis and nerve function, Science 172: 1243 (1971).
J.M. Garden, S.K. Hause, F.C.G. Hoskin, and A.H. Roush, Comparison of DFP-hydrolyzing enzyme purified from head ganglia and hepatopancreas of squid (Loligo pealei) by means of isoelectric focusing, Comp. Biochem. Physiol. 52C: 95 (1975).
F.C.G. Hoskin and R.D. Prusch, Characterization of a DFP-hydrolyzing enzyme in squid posterior salivary gland by use of Soman, DFP and manganous ion, Comp. Biochem. Physiol. 75C: 17 (1983).
F.C.G. Hoskin and K.E. Steinmann, The detoxication of organophosphorus compounds: A tale of two enzymes — or are there more? in “Proceedings of the International Conference on Environmental Hazards of Agrochemicals in Developing Countries”, A.H. El Sebae, ed., University of Alexandria, Egypt (1983).
F.C.G. Hoskin, Inhibition of a Soman- and diisopropyl phosphorofluoridate (DFP)-detoxifying enzyme by Mipafox, Biochem. Pharmacol. 34: 2069 (1985).
W.N. Aldridge, The differentiation of true and pseudo cholinesterase by organophosphorus compounds, Biochem. J. 53: 62 (1953).
M.K. Johnson, The primary biochemical lesion leading to the delayed neurotoxic effects of some organophosphorus esters, J. Neurochem. 23: 785 (1974).
R.J. Richardson, C.S. Davis, and M.K. Johnson, Subcellular distribution of marker enzymes and of neurotoxic esterase in adult hen brain, J. Neurochem. 32: 607 (1979).
R.C. Gupta and W.-D. Dettbarn, Iso-OMPA and Mipafox induced potentiation of toxicity and prevention of tolerance development to subchronic DFP administration, Fed. Proc. 44:1628, Abstr. No. 7123 (1985).
E.T. Reese, J.E. Walker, and D.H. Ball, Extracellular phosphodiesterase of Penicillium funiculosum, ms. submitted, personal communication.
F.C.G. Hoskin and A.H. Roush, Hydrolysis of nerve gas by squid-type diisopropyl phosphorofluoridate hydrolyzing enzyme on agarose resin, Science 215: 1255 (1982).
F.C.G. Hoskin and R.J. Long, Purification of a DFP-hydrolyzing enzyme from squid head ganglion, Arch. Biochem. Biophys. 150: 548 (1972).
M. Dixon and E.G. Webb, “Enzymes”, Academic Press, New York (1979).
D.R. Davies, Neurotoxicity of organophosphorus compounds, in: “Handbuch der Experimentellen Pharmakologie: Cholinesterases and Anticholinesterase Agents”, G.B. Koelle, ed., Springer-Verlag, Berlin (1963).
D.F. Heath, The effects of substituents on the rates of hydrolysis of some organophosphorus compounds. Part I. Rates in alkaline solution, J. Chem. Soc. 3796 (1956).
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© 1987 Plenum Press, New York
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Hoskin, F.C.G., Reese, E.T., Smith, W.J. (1987). Mipafox — Inhibitor of Cholinesterase, Neurotoxic Esterase, and DFP-ase: Is there a “Mipafox-ase”?. In: Dun, N.J., Perlman, R.L. (eds) Neurobiology of Acetylcholine. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-5266-2_36
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DOI: https://doi.org/10.1007/978-1-4684-5266-2_36
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