Abstract
We studied the anticholinesterase and anticarboxylesterase effects of 1,3,2-oxazaphosphorynane derivatives and certain cyclic and acyclic analogs on the two enzymes of homoiotherms (ACE from human erythrocytes and BuCE from horse serum) as well as the enzymes from insect tissues (the nerve cord of the American cockroach and the cephalic region of the domestic fly). The differences in in vitro antiesterase activity of cyclic thionic and the corresponding oxo derivatives of phosphorinane were revealed. The mechanism of the esterase active center phosphorylation not only splitting off the outgoing group (in vivo) but also opening the cycle by P–O bond (in vitro and possibly in vivo) is usually proposed to explain the higher inhibiting activity of the thionic compounds compared to the oxonic ones. The possible involvement of this phosphorylation mechanism in the synergistic activity of the studied compounds is discussed.
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REFERENCES
Brestkin, A.-P., Brik, I.L., Volkova, R.I., et al., Combined Inhibition of Cholinesterase from Horse Serum by Ethers of Diphenylsulfonic and Diphenylthiosulfonic Acids, Dokl. Akad. Nauk SSSR, 1971, vol. 200, no. 1, pp. 103-106.
Brestkin, A.P., Kuznetsova, L.P., Moralev, S.M., et al., Cholinesterases of Terrestrial Animals and Hydrobionts, Vladivostok: TINRO-pentr., 1997.
Brestkin, A.P., Vinyar, G.N., and Rozengart, E.V., Interaction between Brain Cholinsterase and Certain Reversible Ammonium Inhibitors, Biokhimiya, 1981, vol. 46, no. 6, pp. 1042-1048.
Casida, J.E., Oxidative Bioactivation of the Acetylcholinesterase Inhibitors with Emphasis on S-Alkylphosphorothiolate Pesticides, Cholinesterases. Fundamental and Applied Aspects. Proceedings of the 2-th Intern. Meeting on Cholinesterases. Bled, Yugoslavia, De Gruyter, W., Ed., Berlin, 1984, pp. 427-440.
Dikson, M. and Uebb, E., Fermenty (Enzymes), Moscow: Mir, 1966.
Ellman, G.L., Courtney, K.D., Anders, V., and Featherstone, R.M., A New and Rapid Colorimetric Determination of Acetylcholinesterase Activity, Biochem. Pharmacol., 1961, vol. 7, no. 1, pp. 88-95.
Eremina, O.Yu., Bakanova, E.I., Roslavtseva, S.A., Shipov, A.E., Genkina, G.K., Artyushin, O.I., Mndzhoyan, Z.O., Volkova, R.I., Mastryukova, T.A., and Kabachnik, M.I., On the Mechanism of 1,3,2-Oxazaphosphorynane Effect on Insects, Izv. Ross. Akad. Nauk. Ser biol., 1996, no. 6, pp. 664-675.
Karnovsky, M.J. and Roots, Z., A "Direct-Coloring" Thiocholine Method for Cholinesterases, J. Histochem. Cytochem., 1964, vol. 12, pp. 219-222.
Kornish-Bouden, E., Osnovy fermentativnoi kinetiki (Bases of Enzymatic Kinetics), Moscow: Mir, 1979, pp. 43-49.
Maurer, G., Disk-elektroforez. Teoriya i praktika elektroforeza v poliakrilamidnom gele (Disc Electrophoresis. Theory and Practice of Electrophoresis in Polyacrylamide Gel), Moscow: Mir, 1971.
Moralev, S.N., Assays for Kinetic Indices of Interaction between Insect Cholinesterases and the Substrates as well as Irreversible Inhibitors, Biokhimicheskie metody issledovanii v entomologii. Sb. Nauch. Trudov VIZR (Biochemical Methods in Entomology. Collection of VIZR Scientific Papers), Leningrad, 1986, pp. 68-75.
Popov, P.V., Calculation of a Mixture Dose for Fully Additive and Independent Biological Effects of the Components, Khimiya v s.-kh., 1965a, no. 8, pp. 73-75.
Popov, P.V., Statistical Analysis of Experimental Data Using "Pesticide Dose-Activity" Regression Line, Khimiya v s.-kh., 1965b, no. 10, pp. 72-74.
Sharov, A. A., Statisticheskaya obrabotka ekologicheskikh dannykh (Statistical Processing of Ecological Data), Moscow: MGU, 1984, no. 92, p. 86.
Shestakova, N.N., Rozengart, E.V., and Zhorov, B.S., Relationship between Anticholinesterase Efficiency of Ogranophosphorous Inhibitors and Availability of Phosphorus Atoms, Bioorgan. khimiya, 1992, vol. 18, pp. 596-603.
Shipov, A.E., Genkina, G.K., Artyushin, O.I., Mndzhoyan, Z.O., Gushchin, B.E., Chumakova, E.I., Roslavtseva, S.A., Eremina, O.Yu., Bakanova, E.I., Kagan, Yu.S., Ershova, E.A, Mastryukova, T. A., and Kabachnik, M.I., Syntesis and Physiological Activity of New Organophosphorous Pesticides—Analogs of 1,3,2-Oxazaphosphorynane, Izv. Ross. Akad. Nauk. Ser. khim., 1995, no. 11, pp. 2241-2249.
Shipov, A.E., Genkina, G.K., Makhaeva, G.F., Malygin, V.V., Volkova, R.I., Roslavtseva, S.A., Eremina, O.Yu., Bakanova, E.I., Mastryukova, T.A., and Kabachnik, M.I., Investigation of Action Mechanism of Pesticides—Analogs of 2-Aryloxy-2-thio-1,3,2-oxazaphosphorynane, Bioorgan. khimiya, 1999, vol. 25, no. 1, pp. 14-19.
Tawata, S., Kuwano, E., and Eto, M., Studies on Oxazaphospholidines with Pesticidal Activity, Synthesis and Chemical Properties of Insecticidal 2-Alkoxy-4-alkyl-1,3,2-oxazaphospholidine-2-sulfides Derived from Optically Active Amino Acids, Nippor Noyaku Gakkaishi, 1978, vol. 3, no. 2, pp. 161-163.
Van Asperen, K., A Study of Housefly Esterase by Means of Sensitive Colorimetric Method, J. Insect. Physiol., 1962, vol. 8, no. 3, pp. 401-416.
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Khrunin, A.V., Eremina, O.Y., Bakanova, E.I. et al. Specific Interaction between Esterases and 2-Butylthio-2-thio-1,3,2-oxazaphosphorynane and Its Cyclic and Acyclic Analogs. Biology Bulletin 29, 80–87 (2002). https://doi.org/10.1023/A:1013250120785
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DOI: https://doi.org/10.1023/A:1013250120785