Sulfone metabolite of fipronil blocks γ-aminobutyric acid- and glutamate-activated chloride channels in mammalian and insect neurons

Journal of Pharmacology and Experimental Therapeutics

Volumn 314, Issue 1, 2005, Pages 363-373

  Zhao, Xilong ^a   Yeh, Jay Z ^a   Salgado, Vincent L ^a   Narahashi, Toshio ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBUTYRIC ACID; 4 AMINOBUTYRIC ACID A RECEPTOR; CHLORIDE CHANNEL; DRUG METABOLITE; FIPRONIL; GLUTAMIC ACID; SULFONE;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; COCKROACH; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; INSECT CELL; INSECTICIDAL ACTIVITY; MAMMAL CELL; NERVE CELL; NEWBORN; NONHUMAN; PATCH CLAMP; PRIORITY JOURNAL; RAT; SPINAL GANGLION; WHOLE CELL;

ANIMALS; ANIMALS, NEWBORN; CHLORIDE CHANNELS; COCKROACHES; GAMMA-AMINOBUTYRIC ACID; GANGLIA, SPINAL; GLUTAMIC ACID; INSECTICIDES; INSECTS; KINETICS; MEMBRANE POTENTIALS; NEURONS; PATCH-CLAMP TECHNIQUES; PYRAZOLES; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, GABA; RECEPTORS, GABA-A; SULFONES;

EID: 23044456538     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: 10.1124/jpet.104.077891     Document Type: Article

References (31)

1. Bobe A, Meallier P, Cooper J-F, and Coste CM (1998) Kinetics and mechanisms of abiotic degradation of fipronil (hydrolysis and photolysis). J Agric Food Chem 46:2834-2839.
2. Buckingham SD, Hosie AM, Roush RL, and Sattelle DB (1994) Action of agonists and convulsants antagonists on a Drosophila melanogaster GABA receptor (Rdl) homooligomer expressed in Xenopus oocytes. Neurosci Lett 181:137-140.
3. Caboni P, Sammelson E, and Casida JE (2003) Phenylpyrazole insecticide photochemistry, metabolism and GABAergic action: ethiprole compared with fipronil. J Agric Food Chem 51:7055-7061.
4. Casida JE (1993) Insecticide action at the GABA-gated chloride channel: recognition, progress and prospects. Arch Insect Biochem Physiol 22:13-23.
5. Cleland TA (1996) Inhibitory glutamate receptor channels. Mol Neurobiol 13:97-136.
6. Cole LM, Nicholson RA, and Casida JE (1993) Action of phenylpyrazole insecticides at the GABA-gated chloride channel. Pestic Biochem Physiol 46:47-54.
7. Cully DF, Paress PS, Liu KK, Schaeffer JS, and Arena JP (1996) Identification of a Drosophila melanogaster glutamate-gated chloride channel sensitive to the antiparasitic agent avermectin. J Biol Chem 271:20187-20191.
8. Cully DF, Vassilatis DK, Liu KK, Paress PS, Van der Ploeg LHT, Schaeffer JS, and Arena JP (1994) Cloning of an avermectin-sensitive glutamate-gated chloride channel from Caenorhabditis elegans. Nature (Lond) 371:707-711.
9. Durham EW, Siegfried BD, and Scharf ME (2002) In vivo and in vitro metabolism of fipronil by larvae of the European corn borer Ostrinia nubilalis. Pest Manag Sci 58:799-804.
10. Environmental Protection Agency (1996) New Pesticide Fact Sheet, EPA-737-F-96-005, Office of Pesticide Programs, Washington, DC.
11. Fenet H, Beltran E, Gadji B, Cooper JF, and Coste CM (2001) Fate of a phenylpyrazole in vegetation and soil under tropical field conditions. J Agric Food Chem 49:1293-1297.
12. Forrester SG, Hamdan FF, Prichard RK, and Beech RN (1999) Cloning, sequencing and developmental expression levels of a novel glutamate-gated chloride channel homologue in the parasitic nematode Haemonchus contortus. Biochem Biophys Res Commun 254:529-534.
13. Gant DB, Chalmers AE, Wolff MA, Hoffman HB, and Bushey DF (1998) Fipronil: action at the GABA receptor. Rev Toxicol 2:147-156.
14. Hainzl D and Casida JE (1996) Fipronil insecticide: novel photochemical desulfinylation with retention of neurotoxicity. Proc Natl Acad Sci USA 93:12764-12767.
15. Hainzl D, Cole LM, and Casida JE (1998) Mechanisms for selective toxicity of fipronil insecticide and its sulfone metabolite and desulfinyl photoproduct. Chem Res Toxicol 11:1529-1535.
16. Horoszok L, Raymond V, Sattelle DB, and Wolstenholme AJ (2001) GLC-3: a novel fipronil and BIDN-sensitive, but picrotoxin-insensitive, L-glutamate-gated chloride channel subunit from Caenorhabditis elegans. Br J Pharmacol 132:1247-1254.
17. Ikeda T, Zhao X, Kono Y, Yeh JZ, and Narahashi T (2003) Fipronil modulation of glutamate-induced chloride currents in cockroach thoracic ganglion neurons. Neurotoxicology 24:807-815.
18. A receptors in rat dorsal root ganglion neurons. J Pharmacol Exp Ther 296:914-921.
19. Lees G, Beadle DJ, Neumann R, and Benson JA (1987) Responses to GABA by isolated insect neuronal somata: pharmacology and modulation by a benzodiazepines and a barbiturate. Brain Res 401:267-278.
20. Moffat AS (1993) New chemicals seek to outwit insect pests. Science (Wash DC) 261:550-551.
21. Ngim KK, Mabury SA, and Crosby DG (2000) Elucidation of fipronil photodegradation pathways. J Agric Food Chem 48:4661-4665.
22. Raymond V and Sattelle DB (2002) Novel animal-health drug targets from ligandgated chloride channels. Nature Rev Drug Discov 1:427-436.
23. Raymond V, Sattelle DB, and Lapied B (2000) Co-existence in DUM neurons of two GluCl channels that differ in their picrotoxin sensitivity. Neuroreport 11:2695-2701.
24. Sattelle DB, Lummis SCR, Woong JFH, and Rauh JJ (1991) Pharmacology of insect GABA receptors. Neurochem Res 16:363-374.
25. Scharf ME and Siegfried BD (1999) Toxicity and neurophysiological effects of fipronil and fipronil sulfone on the western corn rootworm (Coleoptera: chrysomelidae). Arch Insect Biochem Physiol 40:150-156.
26. Schlenk D, Huggett DB, Allgood J, Bennett E, Rimoldi J, Beeler AB, Block D, Holder AW, Hovinga R, and Bedient P (2001) Toxicity of fipronil and its degradation products to Procambarus sp.: field and laboratory studies. Arch Environ Contam Toxicol 41:325-332.
27. Tingle CC, Rother JA, Dewhurst CF, Lauer S, and King WJ (2003) Fipronil: environmental fate, ecotoxicology and human health concerns. Rev Environ Contam Toxicol 176:1-66.
28. Valles SM, Koehler PG, and Brenner RJ (1997) Antagonism of fipronil toxicity by piperonyl butoxide and S,S,S-tributyl phosphorotrithioate in the German cockroach (Dictyoptera: Blattellidae). J Econ Entomol 90:1254-1258.
29. Zhao X, Salgado VL, Yeh JZ, and Narahashi T (2003) Differential actions of fipronil and dieldrin insecticides on GABA-gated chloride channels in cockroach neurons. J Pharmacol Exp Ther 306:914-924.
30. Zhao X, Salgado VL, Yeh JZ, and Narahashi T (2004a) Kinetic and pharmacological characterization of desensitizing and non-desensitizing glutamate-gated chloride channels in cockroach neurons. Neurotoxicology 25:967-980.
31. Zhao X, Yeh JZ, Salgado VL, and Narahashi T (2004b) Fipronil is a potent open channel blocker of glutamate-activated chloride channels in cockroach neurons. J Pharmacol Exp Ther 310:192-201.