Isotope effects of deuteriated methoxychlor on insecticidal and nerve activities

Okimoto Hiroshi1, Nishimura Keiichiro1, Ueno Tamio1, Fujita Toshio1, Hirano Masachika2, Kurihara Norio3
1Department of Agricultural Chemistry, Kyoto University, Kyoto 606-01, Japan (Fax 81-75-753-6128)
2Takarazuka Research Center, Sumitomo Chemical Co., Ltd., Takarazuka, Hyogo 665, Japan
3Radioisotope Research Center, Kyoto University, Kyoto 606-01, Japan

Tài liệu tham khảo

Hille, 1968, Pharmacological modifications of the sodium channels of frog nerve, J. Gen. Physiol., 51, 199, 10.1085/jgp.51.2.199 Ichinose, 1986, Deuterium and tritium isotope effects on the oxidative demethylation rate of methoxychlor in rat liver microsomes, J. Pestic. sci., 11, 231, 10.1584/jpestics.11.231 Ichinose, 1987, Intramolecular deuterium isotope effect and enantiotopic differentiation in oxidative demethylation of chiral [monomethyl-d3]-methoxychlor in rat liver microsomes, Biochem. Pharmac., 36, 3751, 10.1016/0006-2952(87)90030-X Ichinose, 1986, Synthesis of chiral [monomethyl-d3]methoxychlor and related deuterium-labeled compounds, Agr. Biol. Chem., 50, 1331, 10.1271/bbb1961.50.1331 Julian, 1962, Membrane potentials of the lobster giant axon obtained by use of the sucrose-gap technique, J. Gen. Physiol., 45, 1195, 10.1085/jgp.45.6.1195 Kobayashi, 1989, Quantitative structure-activity studies of pyrethroids. 16. Physicochemical and structural effects of tetramethrin and related compounds on the decay of sodium tail currents in crayfish giant axons, Pestic. Biochem. Physiol., 35, 58, 10.1016/0048-3575(89)90103-X Kobayashi, 1988, Quantitative structure-activity studies of pyrethroids. 13. Physicochemical properties and the rate of development of the residual and tail sodium currents in crayfish giant axon, Pestic. Biochem. Physiol., 30, 251, 10.1016/0048-3575(88)90039-9 Lund, 1981, Modification of sodium channel kinetics by the insecticide tetramethrin in crayfish giant axons, Neurotoxicology, 2, 213 Lund, 1981, Kinetics of sodium channel modification by insecticide tetramethrin in squid axon membranes, J. Pharmac. exp. Ther., 219, 464 Metcalf, 1968, The comparative toxicity of DDT and analogues to susceptible and resistant houseflies and mosquitos, Bull. WHO, 38, 633 Narahashi, 1976, Effects of insecticides on nervous conduction and synaptic transmission, 327 Narahashi, 1967, DDT: Interaction with nerve membrane conductance changes, Science, 157, 1438, 10.1126/science.157.3795.1438 Narahashi, 1960, Mechanism of increase in negative after-potential by dicophanum (DDT) in the giant axons of the cockroach, J. Physiol., 152, 122, 10.1113/jphysiol.1960.sp006475 Nishimura, 1983, Quantitative structureactivity relationships of DDT and its related compounds, J. Pestic. sci., 8, 69, 10.1584/jpestics.8.69 Nishimura, 1986, Symptomatic and neurophysiological activities of new synthetic non-ester pyrethroids, ethofenprox, MTI-800, and related compounds, Pestic. Biochem. Physiol., 25, 387, 10.1016/0048-3575(86)90013-1 Nishimura, 1991, Quantitative structure-activity studies of pyrethroids. 23. Rate of decrease in sodium tail currents induced by substituted benzyl chrysanthemates and pyrethrates in crayfish giant axons, Pestic. Biochem. Physiol., 40, 99, 10.1016/0048-3575(91)90104-T Nishimura, 1992, Comparison of symptomatic and neurophysiological activities of enantiomers of the insecticide 3-phenoxybenzyl 1-(4-ethoxyphenyl)-2,2-dichlorocyclopropane-1-carboxylate, Pestic. sci., 34, 249, 10.1002/ps.2780340310 Omatsu, 1988, Effect of substituted benzyl chrysanthemates on sodium and potassium currents in the crayfish giant axon, Pestic. Biochem. Physiol., 30, 125, 10.1016/0048-3575(88)90046-6 Perry, 1967, Comparative toxicity and metabolism of p,p'-DDT and various substituted DDT-derivatives by houseflies, J. Econ. Entomol., 60, 568, 10.1093/jee/60.2.568 Tanaka, 1976, Comparative insecticidal activities and metabolic rates of lindane and its hexadeuterio-analog, Pestic. Biochem. Physiol., 6, 386, 10.1016/0048-3575(76)90049-3 Tanaka, 1981, The mechanism of resistance to lindane and hexadeuterated lindane in the Third Yumenoshima strain of housefly, Pestic. Biochem. Physiol., 16, 149, 10.1016/0048-3575(81)90048-1 Uchida, 1974, Insecticidal and neuroexciting actions of DDT analogs, Pestic. Biochem. Physiol., 4, 451, 10.1016/0048-3575(74)90069-8 Vijverberg, 1982, Similar mode of action of pyrethroids and DDT on sodium channel gating in myelinated nerves, Nature, Lond., 295, 601, 10.1038/295601a0 Whalen, 1966, Deuterium isotope studies on selected pesticides and synergists, 1