Blockage of chloride channels and anion transporters with pesticidal natural products and their synthetic analogs

Asmild M, Willumsen N (2000) Chloride channels in the plasma membrane of a foetal Drosophila cell line, S2. Pflug Arch Eur J Physiol 439:759–764 Bloomquist JR (1994) Cyclodiene resistance at the insect GABA receptor/chloride channel complex confers broad cross resistance to convulsants and experimental phenylpyrazole insecticides. Arch Insect Biochem Physiol 26(1):69–79 Bloomquist JR (2001) GABA and glutamate receptors as biochemical sites for insecticide action. In: Ishaaya I (ed) Biochemical sites of insecticide action and resistance. Springer, Berlin, pp 17–41 Bloomquist JR (2003) Chloride channels as tools for developing selective insecticides. Arch Insect Biochem Physiol 54:145–156 Bloomquist JR, Boina D, Chow E, Carlier PR, Reina M, Gonzalez-Coloma A (2008) Mode of action of the plant-derived silphinenes on insect and mammalian GABAA receptor/chloride channel complex. Pestic Biochem Physiol 91:17–23 Boina D, Bloomquist JR (2009) Toxicity and disruption of midgut physiology in larvae of the European corn borer, Ostrinia nubilalis, by anion transporter blockers. Arch Insect Biochem Physiol 70:151–161 Boina D, Bloomquist JR (2010) Reduced expression of voltage-gated chloride channel genes in Caenorhabditis elegans: Implications for the mode of action of chloride channel-directed nematicides. Pestic Biochem Physiol (in press) Boina D, Lewis EE, Bloomquist JR (2008) Nematicidal activity of anion transport blockers against Meloidogyne incognita, Caenorhabditis elegans, and Heterorhabditis bacteriophora. Pest Manag Sci 64:646–653 Boudko DY, Moroz LL, Harvey WR, Linser PJ (2001) Alkalinization by chloride/bicarbonate pathway in larval mosquito midgut. Proc Natl Acad Sci USA 98:15354–15359 Cabantchik ZI, Greger R (1992) Chemical probes for anion transporters of mammalian cell membranes. Am J Physiol 262:C803–C827 Casida JE (2009) Pest toxicology: the primary mechanisms of pesticide action. Chem Res Toxicol 22:609–619 Chao AC, Koch AR, Moffett DF (1989) Active chloride transport in isolated posterior midgut of tobacco hornworm (Manduca sexta). Am J Physiol 257:R752–R761 Ciche TA, Ensign JA (2003) For the insect pathogen Photorhabdus luminiscens, which end of a nematode is out? Appl Environ Microbiol 69:1890–1897 Cleland TA, Selverston AI (1995) Glutamate-gated inhibitory currents of central pattern generator neurons in the lobster stomatogastric ganglion. J Neurosci 15(10):6631–6639 Cully DF, Paress PF, Liu KK, Schaeffer JM, Arena JP (1996) Identification of a Drosophila melanogaster glutamate-gated chloride channel sensitive to the antiparasitic agent avermectin. J Biol Chem 271:20187–20191 El Hassani AK, Giurfa M, Gauthier M, Armengaud C (2008) Inhibitory neurotransmission and olfactory memory in honeybees. Neurobiol Learn Mem 90:585–590 Fahlke C (2001) Ion permeation and selectivity in ClC-type chloride channels. Am J Physiol Renal Physiol 280:F748–F757 Ferroni S, Marchini C, Nobile M, Rapisarda C (1997) Characterization of an inwardly rectifying chloride conductance expressed by cultured rat cortical astrocytes. Glia 21:217–227 ffrench-Constant R, Steichen J, Rocheleau T, Aronstein K, Roush R (1993) A single-amino acid substitution in a γ-aminobutyric acid subtype A receptor locus is associated with cyclodiene insecticide resistance in Drosophila populations. Proc Natl Acad Sci USA 90:1957–1961 Forst S, Dowds B, Boemare N, Stackebrandt E (1997) Xenorhabdus and Photorhabdus spp.: bugs that kill bugs. Annu Rev Microbiol 51:47–72 Gengs C, Leung H-T, Skingsley D, Iovchev M, Yin Z, Semenev E, Burg M, Hardie R, Pak W (2002) The target of Drosophila photoreceptor synaptic transmission is a histamine-gated chloride channel encoded by ort (hclA). J Biol Chem 277:42113–42120 Gonzalez-Coloma A, Reina M, Cabrera R, Castanera P, Gutierrez C (1995) Antifeedant and toxic effects of sesquiterpenes from Senecio palmensis to Colorado potato beetle. J Chem Ecol 21:1255–1270 Gonzalez-Coloma A, Gutierrez C, Cabrera R, Reina M (1997) Silphinene derivatives: their effects and mode of action on Colorado potato beetle. J Agric Food Chem 45:946–950 Gonzalez-Coloma A, Valencia F, Martin N, Hoffmann JJ, Hutter L, Marco JA, Reina M (2002) Silphinene sesquiterpenes as model insect antifeedants. J Chem Ecol 28:117–129 Hu K, Webster JM (2000) Antibiotic production in relation to bacterial growth and nematode development in Photorhabdus-Heterorhabditis infected Galleria mellonella larvae. FEMS Microbiol Lett 189:219–223 Hu K, Li J, Webster JM (1999) Nematicidal metabolites produced by Photorhabdus luminescens (Enterobacteriaceae), bacterial symbiont of entomopathogenic nematodes. Nematology 1:457–469 Jentsch TJ, Stein V, Weinreich F, Zdebik AA (2002) Molecular structure and physiological function of chloride channels. Physiol Rev 82:503–568 Ludmerer SW, Warren VA, Williams BS, Zheng Y, Hunt DC, Ayer MB, Wallace MA, Chaudhary AG, Egan MA, Meinke PT, Dean DC, Garcia ML, Cully DF, Smith MM (2002) Ivermectin and nodulisporic acid receptors in Drosophila melanogaster contain both gamma-aminobutyric acid-gated Rdl and glutamate-gated GluCl alpha chloride channel subunits. Biochemistry 41:6548–6560 Lummis S (1990) GABA receptors in insects. Comp Biochem Physiol 95C:1–8 Machaca K, Defelice LJ, Hernault SWL (1996) A novel chloride channel localizes to Caenorhabditis elegans spermatids and chloride channel blockers induce spermatid differentiation. Dev Biol 176:1–16 Malekova L, Tomaskova J, Novakova M, Stefanik P, Kopacek J, Lokatos B, Pastorekova S, Krizanova O, Breier A, Ondrias K (2007) Inhibitory effect of DIDS, NPPB, and phloretin on intracellular chloride channels. Pflugers Arch Eur J Physiol 455:349–357 Mullin CA, Chyb S, Eichenseer H, Hollister B, Frazier JL (1994) Neuroreceptor mechanisms in insect gestation: a pharmacological approach. J Insect Physiol 40:913–931 Mullin CA, Gonzalez-Coloma A, Gutierrez C, Reina M, Eichenseer H, Hollister B, Chyb S (1997) Antifeedant effects of some novel terpenoids on chrysomelidae beetles: comparisons with alkaloids on an alkaloid-adapted and nonadapted species. J Chem Ecol 23:1851–1866 Nagel W, Somieski P, Katz U (2001) Selective inhibition of Cl− conductance in toad skin by blockers of Cl− channels and transporters. Am J Physiol Cell Physiol 281:C1223–C1232 Pedersen TH, Paoli FD, Nielsen OB (2005) Increased excitability of acidified skeletal muscle: role of chloride conductance. J Gen Physiol 125:237–246 Pusch M, Accardi A, Liantonio A, Guida P, Traverso S, Camerino DC, Conti F (2002) Mechanisms of block of muscle type CLC chloride channels (Review). Mol Mem Biol 19:285–292 Raymond V, Sattelle DB (2002) Novel animal-health drug targets from ligand-gated chloride channels. Nat Rev 1:427–436 Raymond V, Sattelle DB, Lapied B (2000) Co-existence in DUM neurons of two GluCl channels that differ in their picrotoxin sensitivity. NeuroReport 11:2695–2701 Reina M, Nold M, Santana O, Orihuela JC, Gonzalez-Coloma A (2002) C-5-Substituted antifeedant silphinene sesquiterpenes from Senecio palmensis. J Nat Prod 65:448–453 Rohrer S, Arena J (1995) Structural and functional characterization of insect genes encoding ligand-gated chloride channel subunits. In: Clark JM (ed) Molecular action of insecticides on ion channels Amer Chem Soc Symp Ser 591, Washington, DC, pp 264–283 Shanbhag S, Tripathi S (2005) Electrogenic H+ transport and pH gradients generated by a V-H+-ATPase in the isolated perfused larval Drosophila midgut. J Membr Biol 206:61–72 Sterling D, Casey JR (2002) Bicarbonate transport proteins. Biochem Cell Biol 80:483–497 Wang Y, Telfer WH (1998) Cyclic-AMP-induced water uptake in a moth ovary: inhibition by bafilomycin and anthracene-9-carboxylic acid. J Exp Biol 201:1627–1635 Yamamoto D, Suzuki N (1987) Single-channel recordings of chloride currents in primary cultured Drosophila neurons. Arch Insect Biochem Physiol 6:151–158 Zhao X, Yeh JG, Salgado VL, Narahashi T (2004) Fipronil is a potent open channel blocker of glutamate-activated chloride channels in cockroach neurons. J Pharmacol Exp Ther 310:192–201