Action of Insecticidal N-Alkylamides at Site 2 of the Voltage-Sensitive Sodium Channel

Document Type

Article

Publication Date

1-1-1990

Abstract

Nine synthetic N-alkylamides were examined as inhibitors of the specific binding of [3H]- batrachotoxinin,A 20α-benzoate ([3H]BTX-B) to sodium channels and as activators of sodium uptake in mouse brain synaptoneurosomes. In the presence of scorpion (Leiurus quinquestriatus) venom, the six insecticidal analogues were active as both inhibitors of [3H]BTX-B binding and stimulators of sodium uptake. These findings are consistent with an action of these compounds at the alkaloid activator recognition site (site 2) of the voltage-sensitive sodium channel. The three noninsecticidal N-alkylamides also inhibited [3H]BTX-B binding but were ineffective as activators of sodium uptake. Concentration-response studies revealed that some of the insecticidal amides also enhanced sodium uptake through a second, high-affinity interaction that does not involve site 2, but this secondary effect does not appear to be correlated with insecticidal activity. The activities of N-alkylamides as sodium channel activators were influenced by the length of the alkenyl chain and the location of unsaturation within the molecule. These results further define the actions of N-alkylamides on sodium channels and illustrate the significance of the multiple binding domains of the sodium channel as target sites for insect control agents. © 1990, American Chemical Society. All rights reserved.

Publication Source (Journal or Book title)

Journal of Agricultural and Food Chemistry

First Page

1724

Last Page

1728

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