Pyrethroid insecticides: stereospecific allosteric interaction with the batrachotoxinin-A benzoate binding site of mammalian voltage-sensitive sodium channels.

Pyrethroid insecticides are synthetic neurotoxins patterned after the naturally occurring pyrethrins. Their mechanism of action is thought to involve effects primarily at the voltage-sensitive sodium channel of both insect and mammalian neurons, although recent studies have raised the possibility that these compounds may also act at the gamma-aminobutyric acid receptor-chloride ionophore complex. Here we show that active pyrethroids of the alpha-cyano-3-phenoxybenzyl class allosterically enhance the binding of [3H]batrachotoxinin-A 20-alpha-benzoate to voltage-sensitive sodium channels of rat brain in a dose-dependent and stereospecific manner. Comparison of the rank order of potency for enhancement of [3H]batrachotoxinin-A 20-alpha-benzoate binding and insecticidal activity in a series of toxic stereoisomers of cypermethrin, representative of the class, reveals a correlation between the two measures. These results support a sodium channel site model for pyrethroid action and suggest a useful and practical method to help evaluate the relationship between effects at the sodium channel and insecticidal potency for members of this class of compounds.

• Publication year

  1988

• Venue

  Molecular Pharmacology

• Publication date

  1988-07-01

• Fields of study

  Biology, Medicine, Chemistry

• Identifiers
  DOI 10.1016/s0026-895x(25)08639-0PMID 2455860
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• The findings support a sodium channel site model for pyrethroid action and indicate that binding enhancement at the sodium channel can serve as a practical assay for relating channel effects to insecticidal potency.

  Confidence 0.91

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewAK (4715169a40) reviewq (76h6bfydm6) review
• Across toxic stereoisomers of cypermethrin, the rank order of potency for enhancing [3H]batrachotoxinin-A 20-alpha-benzoate binding correlates with insecticidal activity.

  Confidence 0.95

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewAK (4715169a40) reviewq (76h6bfydm6) review
• Active alpha-cyano-3-phenoxybenzyl pyrethroids allosterically enhance binding of [3H]batrachotoxinin-A 20-alpha-benzoate to rat brain voltage-sensitive sodium channels in a dose-dependent and stereospecific manner.

  Confidence 0.98

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewAK (4715169a40) reviewq (76h6bfydm6) review

• [3h]batrachotoxinin-a 20-alpha-benzoate

  ligand

  A radiolabeled ligand used to measure binding at the batrachotoxinin-A benzoate site on sodium channels.

  Aliases: BTX-B

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewAK (4715169a40) reviewq (76h6bfydm6) review
• alpha-cyano-3-phenoxybenzyl pyrethroids

  compound class

  A pyrethroid subclass containing the alpha-cyano-3-phenoxybenzyl structural motif examined for sodium-channel interactions.

  Aliases: alpha-cyano-3-phenoxybenzyl class

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewAK (4715169a40) reviewq (76h6bfydm6) review
• cypermethrin toxic stereoisomers

  compound group

  Toxic stereoisomeric forms of cypermethrin used as representative pyrethroid compounds in the potency comparison.

  Aliases: toxic stereoisomers of cypermethrin

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewAK (4715169a40) reviewq (76h6bfydm6) review
• insecticidal activity

  activity measure

  The insect-killing potency used as the biological activity measure for comparing pyrethroid stereoisomers.

  Aliases: insecticidal potency

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewAK (4715169a40) reviewq (76h6bfydm6) review
• pyrethroid insecticides

  compound class

  Synthetic neurotoxic insecticides patterned after naturally occurring pyrethrins.

  Aliases: pyrethroids

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewAK (4715169a40) reviewq (76h6bfydm6) review
• sodium channel site model

  model

  A mechanistic model in which pyrethroid action is explained through interaction at a sodium-channel site.

  Aliases: sodium channel model

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewAK (4715169a40) reviewq (76h6bfydm6) review
• voltage-sensitive sodium channels

  protein target

  Membrane ion channels in rat brain neurons that serve as the binding target measured in this assay.

  Aliases: voltage-gated sodium channels, sodium channels

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewAK (4715169a40) reviewq (76h6bfydm6) review

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