Chlorocyclohexane insecticides and male medfly attractants: similar stereospecificity for neuroactivity and interactions with a housefly [35S]t-butylbicyclophosphorothionate binding site.
[35S]t-Butylbicyclophosphorothionate [( 35S]TBPS) undergoes saturable specific binding to a membrane preparation from housefly thoraxes and abdomens with apparent Kd and Bmax values at equilibrium of 0.17 microM and 2.2 pmol/mg protein at 20 degrees C. Lindane is more potent than three other isomers of hexachlorocyclohexane as a toxicant for houseflies and in displacing [35S]TBPS from this housefly membrane preparation. This correlation of similar stereospecificity for neuroactivity and interaction with the TBPS receptor extends to the Mediterranean fruit fly male attractant trimedlure and its components and analogs. The relative attractancy of t-butyl cis-4-chloro-trans-2-methylcyclohexanecarboxylate and of three less active isomers of this trans-chlorocyclohexane-carboxylate parallel their potency in the [35S]TBPS binding assay. With both trimedlure and the related cyclohexene attractant siglure the trans-isomers are more potent than the cis-isomers as attractants and in displacing [35S]TBPS. Scatchard analyses indicate that lindane binds at the same site as [35S]TBPS. The hexachlorocyclohexane isomers and trimedlure components are much more potent inhibitors with membrane preparations from houseflies than from rat brain. The housefly TBPS receptor possibly serves as a model for the primary target sites, thereby suggesting that both the insecticide and the attractant may interact with some component of the putative GABAergic nervous or neuromuscular system.
Cohen
E
E
Casida
J E
JE
D000818:Animals; D001921:Brain / Q000378:metabolism; D001643:Bridged Bicyclo Compounds / Q000378:metabolism*; D019086:Bridged Bicyclo Compounds, Heterocyclic; D001952:Bridged-Ring Compounds / Q000378:metabolism*; D003509:Cyclohexanecarboxylic Acids / Q000378:metabolism*; D053138:Cyclohexenes; D004175:Diptera; D005260:Female; D001556:Hexachlorocyclohexane / Q000378:metabolism* / Q000633:toxicity; D006793:Houseflies / Q000378:metabolism*; D007928:Lethal Dose 50; D008297:Male; D051379:Mice; D010675:Pheromones / Q000378:metabolism*; D051381:Rats; D011963:Receptors, GABA-A / Q000378:metabolism*; D012724:Sex Attractants / Q000378:metabolism*; D013237:Stereoisomerism
D001643:Bridged Bicyclo Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D001952:Bridged-Ring Compounds; D003509:Cyclohexanecarboxylic Acids; D053138:Cyclohexenes; D010675:Pheromones; D011963:Receptors, GABA-A; D012724:Sex Attractants; C045211:trimedlure; C045212:siglure; D001556:Hexachlorocyclohexane; C037476:tert-butylbicyclophosphorothionate