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Structure and Function of Insect Nicotinic Acetylcholine Receptors Studied with Nicotinoid Insecticide Affinity Probes

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Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor

Abstract

The insect nicotinic acetylcholine (ACh) receptor (nAChR) is the target not only for the botanical insecticide nicotine but also for the synthetic nicotinoid insecticides such as imidacloprid (IMI) (Bai et al. 1991; Tomizawa and Yamamoto 1992, 1993; Liu and Casida 1993; Liu et al. 1993, 1995; Tomizawa et al. 1995a; Matsuo et al. 1998). Knowledge of the structure-activity relationship (SAR) of nicotinoids contributes to an understanding of the functional architecture of the nicotinic acetylcholine receptor (nAChR), a generic interrelationship of SAR and target site research applicable to any agrochemical or pharmaceutical. This approach has helped us to understand the action and selectivity of the new and increasingly important synthetic nicotinoid insecticides useful in controlling important pests and in resistance management programs (Casida and Quistad 1998).

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References

  • Amar M, Thomas P, Wonnacott S, Lunt GG (1995) A nicotinic acetylcholine receptor subunit from insect brain forms a non-desensitising homo-oligomeric nicotinic acetylcholine receptor when expressed in Xenopus oocytes. Neurosci Lett 199:107–110

    Article  PubMed  CAS  Google Scholar 

  • Arias HR (1997) Topology of ligand binding sites on the nicotinic acetylcholine receptor. Brain Res Rev 25:133–191

    Article  PubMed  CAS  Google Scholar 

  • Bai D, Lummis SCR, Leicht W, Breer H, Sattelle DB (1991) Actions of imidacloprid and a related nitromethylene on cholinergic receptors of an identified insect motor neurone. Pestic Sci 33:197–204

    Article  CAS  Google Scholar 

  • Bertrand D, Ballivet M, Gomez M, Bertrand S, Phannavong B, Gundelfinger ED (1994) Physiological properties of neuronal nicotinic receptors reconstituted from the vertebrate β2 subunit and Drosophila α subunits. Eur J Neurosci 6:869–875

    Article  PubMed  CAS  Google Scholar 

  • Bossy B, Ballivet M, Spierer P (1988) Conservation of neuronal nicotinic acetylcholine receptors from Drosophila to vertebrate central nervous systems. EMBO J 7:611–618

    PubMed  CAS  Google Scholar 

  • Breer H, Kleene R, Hinz G (1985) Molecular forms and subunit structure of the acetylcholine receptor in the central nervous system of insects. J Neurosci 5:3386–3392

    PubMed  CAS  Google Scholar 

  • Buckingham SD, Lapied B, Corronc HL, Grolleau F, Sattelle DB (1997) Imidacloprid actions on insect neuronal acetylcholine receptors. J Exp Biol 200:2685–2692

    PubMed  CAS  Google Scholar 

  • Casida JE (1970) Mixed-function oxidase involvement in the biochemistry of insecticide synergists. J Agrie Food Chem 18:753–772

    Article  CAS  Google Scholar 

  • Casida JE, Quistad GB (1998) Golden age of insecticide research: past, present, or future? Annu Rev Entomol 43:1–16

    Article  PubMed  CAS  Google Scholar 

  • Chao SL, Casida JE (1997) Interaction of imidacloprid metabolites and analogs with the nicotinic acetylcholine receptor of mouse brain in relation to toxicity. Pestic Biochem Physiol 58:77–88

    Article  CAS  Google Scholar 

  • Chao SL, Dennehy TJ, Casida JE (1997) Whitefly (Hemiptera: Aleyrodidae) binding site for imidacloprid and related insecticides: a putative nicotinic acetylcholine receptor. J Econ Entomol 90:879–882

    PubMed  CAS  Google Scholar 

  • David JA, Sattelle DB (1984) Actions of cholinergic pharmacological agents on the cell body membrane of the fast coxal depressor motorneuron of the cockroach (Periplaneta americana). J Exp Biol 108:119–136

    CAS  Google Scholar 

  • Hanke W, Breer H (1986) Channel properties of an insect neuronal acetylcholine receptor protein reconstituted in planar lipid bilayers. Nature 321:171–174

    Article  PubMed  CAS  Google Scholar 

  • Hermans-Borgmeyer I, Zopf D, Ryseck R-P, Hovemann B, Betz H, Gundelfinger ED (1986) Primary structure of a developmentally regulated nicotinic acetylcholine receptor protein from Drosophila. EMBO J 5:1503–1508

    PubMed  CAS  Google Scholar 

  • Jonas P, Baumann A, Merz B, Gundelfinger ED (1990) Structure and developmental expression of the Dα2 gene encoding a novel nicotinic acetylcholine receptor protein of Drosophila melanogaster. FEBS Lett 269:264–268

    Article  PubMed  CAS  Google Scholar 

  • Jonas PE, Phannavong B, Schuster R, Schröder C, Gundelfinger ED (1994) Expression of the ligand-binding nicotinic acetylcholine receptor subunit Dα2 in the Drosophila central nervous system. J Neurobiol 25:1494–1508

    Article  PubMed  CAS  Google Scholar 

  • Kagabu S, Moriya K, Shibuya K, Hattori Y, Tsuboi S, Shiokawa K (1992) l-(6-Halonicotinyl)-2-nitromethylene imidazolidines as potential new insecticides. Biosci Biotechnol Biochem 56:362–363

    Article  CAS  Google Scholar 

  • Karlin A, Akabas MH (1995) Toward a structural basis for the function of nicotinic acetylcholine receptors and their cousins. Neuron 15:1231–1244

    Article  PubMed  CAS  Google Scholar 

  • Kishida H, Sakamoto N, Umeda K, Fujimoto H (1992) Preparation of nitropyrimidine derivatives as insecticides. Jpn Kokai Tokkyo Koho JP04,173,788; Chem Abstr 118, 22251q

    Google Scholar 

  • Kotzyba-Hibert F, Kapfer I, Goeldner M (1995) Recent trends in photoaffinity labeling. Angew Chem Int Ed Engl 34:1296–1312

    Article  CAS  Google Scholar 

  • Lansdell S J, Schmitt B, Betz H, Sattelle DB, Millar NS (1997) Temperature-sensitive expression of Drosophila neuronal nicotinic acetylcholine receptors. J Neurochem 68:1812–1819

    Article  PubMed  CAS  Google Scholar 

  • Lapied B, Corronc HL, Hue B (1990) Sensitive nicotinic and mixed nicotinic-muscarinic receptors in insect neurosecretory cells. Brain Res 533:132–136

    Article  PubMed  CAS  Google Scholar 

  • Latli B, Casida JE (1992) [3H]Imidacloprid: synthesis of a candidate radioligand for the nicotinic acetylcholine receptor. J Labelled Compd Radiopharm 31:609–613

    Google Scholar 

  • Latli B, Than C, Morimoto H, Williams PG, Casida JE (1996) [6-Chloro-3-pyridylmethyl-[3H]neonicotinoids as high-affinity radioligands for the nicotinic acetylcholine receptor: preparation using NaB3H4 and LiB3H4. J Labelled Comp Radiopharm 38:971–978

    Article  CAS  Google Scholar 

  • Latli B, Tomizawa M, Casida JE (1997) Synthesis of a novel [125]neonicotinoid photoaffinity probe for the Drosophila nicotinic acetylcholine receptor. Bioconjugate Chem 8:7–14

    Article  CAS  Google Scholar 

  • Lindstrom J (1997) Nicotinic acetylcholine receptors in health and disease. Mol Neurobiol 15:193–222

    Article  PubMed  CAS  Google Scholar 

  • Liu M-Y, Casida JE (1993) High affinity binding of [3H] imidacloprid in the insect acetylcholine receptor. Pestic Biochem Physiol 46:40–46

    Article  CAS  Google Scholar 

  • Liu M-Y, Lanford J, Casida JE (1993) Relevance of [3H] imidacloprid binding site in house fly head acetylcholine receptor to insecticidal activity of 2-nitromethylene-and 2-nitroimino-imidazolidines. Pestic Biochem Physiol 46:200–206

    Article  CAS  Google Scholar 

  • Liu M-Y, Latli B, Casida JE (1994) Nitomethyleneimidazolidine radioligand ([3H]NMI): high affinity and cooperative binding for house fly acetylcholine receptor. Pestic Biochem Physiol 50:171–182

    Article  CAS  Google Scholar 

  • Liu M-Y, Latli B, Casida JE (1995) Imidacloprid binding site in Musca nicotinic acetylcholine receptor: interactions with physostigmine and a variety of nicotinic agonists with chloropyridyl and chlorothiazolyl substituents. Pestic Biochem Physiol 52:170–181

    Article  CAS  Google Scholar 

  • March CS, Cattell KJ, Donnellan JF (1982) Pharmacologicaal characteristics of a putative nicotinic acetylcholine receptor from Musca domestica. In: Evered D, O’Connor M, Whelan J (eds) Ciba Foundation Symposium 88: Neuropharmacology of Insects. Pitman, London, pp 118–136

    Google Scholar 

  • Marshall J, Buckingham SD, Shingai R, Lunt GG, Goosey MW, Darlison MG, Sattelle DB, Barnard EA (1990) Sequence and functional expression of a single a subunit of an insect nicotinic acetylcholine receptor. EMBO J 9:4391–4398

    PubMed  CAS  Google Scholar 

  • Matsuo H, Tomizawa M, Yamamoto I (1998) Structure-activity relationships of acyclic nicotinoids and neonicotinoids for insect nicotinic acetylcholine receptor/ion channel complex. Arch Insect Biochem Physiol 37:17–23

    Article  CAS  Google Scholar 

  • Mebs D, Narita K, Iwanaga S, Samejima Y, Lee CY (1971) Amino acid sequence of α bungarotoxin from the venom of Bungarus multicinctus. Biochem Biophys Res Commun 44:711–716

    Article  PubMed  CAS  Google Scholar 

  • Minamida I, Iwanaga K, Tabuchi T, Uneme H, Dantsuji H, Okauchi T (1993) Synthesis and insecticidal activity of acyclic nitroethene compounds containing a 3-pyridyl-methylamino group. J Pestic Sci 18:31–40

    Article  Google Scholar 

  • Moriya K, Shibuya K, Hattori Y, Tsuboi S, Shiokawa K, Kagabu S (1992) l-(6-Chloronicotinyl)-2-nitroimino-imidazolidines and related compounds as potential new insecticides. Biosci Biotechnol Biochem 56:364–365

    Article  CAS  Google Scholar 

  • Nishimura K, Kanda Y, Okazawa A, Ueno T (1994) Relationship between insecticidal and neurophysiological activities of imidacloprid and related compounds. Pestic Biochem Physiol 50:51–59

    Article  CAS  Google Scholar 

  • Ohana B, Gershoni JM (1990) Comparison of the toxin binding sites of the nicotinic acetylcholine receptor from Drosophila to human. Biochemistry 29:6409–6415

    Article  PubMed  CAS  Google Scholar 

  • Papke RL (1993) The kinetic properties of neuronal nicotinic receptors: genetic basis of functional diversity. Prog Neurobiol 41:509–531

    Article  PubMed  CAS  Google Scholar 

  • Pedersen SE, Cohen JB (1990) d-Tubocurarine binding sites are located at α-γ and α-δ subunit interfaces of the nicotinic acetylcholine receptor. Proc Natl Acad Sci USA 87:2785–2789

    Article  PubMed  CAS  Google Scholar 

  • Sargent PB (1993) The diversity of neuronal nicotinic acetylcholine receptors. Annu Rev Neurosci 16:403–443

    Article  PubMed  CAS  Google Scholar 

  • Sattelle DB, Breer H (1985) Purification by affinity-chromatography of a nicotinic acetylcholine receptor from the CNS of the cockroach Periplaneta americana. Comp Biochem Physiol [C] 82:349–352

    Article  Google Scholar 

  • Sawruk E, Schloss P, Betz H, Schmitt B (1990a) Heterogeneity of Drosophila nicotinic acetylcholine receptors: SAD, a novel developmentally regulated α-subunit. EMBO J 9:2671–2677

    PubMed  CAS  Google Scholar 

  • Sawruk E, Udri C, Betz H, Schmitt B (1990b) SBD, a novel structural subunit of the Drosophila nicotinic acetylcholine receptor, shares its genomic localization with two α-subunits. FEBS Lett 273:177–181

    Article  PubMed  CAS  Google Scholar 

  • Schloss P, Hermans-Borgmeyer I, Betz H, Gundelfinger ED (1988) Neuronal acetylcholine receptors in Drosophila: the ARD protein is a component of a high-affinity α-bungarotoxin binding complex. EMBO J 7:2889–2894

    PubMed  CAS  Google Scholar 

  • Schloss P, Betz H, Schröder C, Gundelfinger ED (1991) Neuronal nicotinic acetylcholine receptors in Drosophila: antibodies against an α-like and a non-a-subunit recognize the same high-affinity α-bungarotoxin binding complex. J Neurochem 57:1556–1562

    Article  PubMed  CAS  Google Scholar 

  • Schloss P, Mayser W, Gundelfinger ED, Betz H (1992) Cross-linking of 125I-α-bungarotoxin to Drosophila head membranes identifies a 42 kDa toxin binding polypeptide. Neurosci Lett 145:63–66

    Article  PubMed  CAS  Google Scholar 

  • Schuster R, Phannavong B, Schröder C, Gundelfinger ED (1993) Immunohistochemical localization of a ligand-binding and a structural subunit of nicotinic acetylcholine receptors in the central nervous system of Drosophila melanogaster. J Comp Neurol 335:149–162

    Article  PubMed  CAS  Google Scholar 

  • Sgard F, Obosi LA, King LA, Windass JD (1993) ALS and SAD-like nicotinic acetylcholine receptor subunit genes are widely distributed in insects. Insect Mol Biol 2:215–223

    Article  PubMed  CAS  Google Scholar 

  • Takahashi H, Mitsui J, Takakusa N, Matsuda M, Yoneda H, Suzuki J, Ishimitsu K, Kishimoto T (1992) NI-25, a new type of systemic and broad spectrum insecticide. Brighton Crop Prot Conf Pests Dis 1:89–96

    Google Scholar 

  • Tomizawa M (1994) Structure-activity relationships of nicotinoids and the related compounds. J Pestic Sci 19:S229-S240

    Google Scholar 

  • Tomizawa M, Casida JE (1997) [125I]Azidonicotinoid photoaffinity labeling of insecticide-binding subunit of Drosophila nicotinic acetylcholine receptor. Neurosci Lett 237:61–64

    Article  PubMed  CAS  Google Scholar 

  • Tomizawa M, Yamamoto I (1992) Binding of nicotinoids and the related compounds to the insect nicotinic acetylcholine receptor. J Pestic Sci 17:231–236

    Article  CAS  Google Scholar 

  • Tomizawa M, Yamamoto I (1993) Structure-activity relationships of nicotinoids and imidacloprid analogs. J Pestic Sci 18:91–98

    Article  Google Scholar 

  • Tomizawa M, Otsuka H, Miyamoto T, Eldefrawi ME, Yamamoto I (1995a) Pharmacological characteristics of insect nicotinic acetylcholine receptor with its ion channel and the comparison of the effect of nicotinoids and neonicotinoids. J Pestic Sci 20:57–64

    Article  CAS  Google Scholar 

  • Tomizawa M, Otsuka H, Miyamoto T, Yamamoto I (1995b) Pharmacological effects of imidacloprid and its related compounds on the nicotinic acetylcholine receptor with its ion channel from the Torpedo electric organ. J Pestic Sci 20:49–56

    Article  CAS  Google Scholar 

  • Tomizawa M, Latli B, Casida JE (1996) Novel neonicotinoid-agarose affinity column for Drosophila and Musca nicotinic acetylcholine receptors. J Neurochem 67:1669–1676

    Article  PubMed  CAS  Google Scholar 

  • Unwin N (1995) Acetylcholine receptor channel imaged in the open state. Nature 373:37–43

    Article  PubMed  CAS  Google Scholar 

  • Yamamoto I, Yabuta G, Tomizawa M, Saito T, Miyamoto T, Kagabu S (1995) Molecular mechanism for selective toxicity ofnicotinoids and neonicotinoids. J Pestic Sci 20:33–40

    Article  CAS  Google Scholar 

  • Yamamoto I, Tomizawa M, Saito T, Miyamoto T, Walcott EC, Sumikawa K (1998) Structural factors contributing to insecticidal and selective actions of neonicotinoids. Arch Insect Biochem Physiol 37:24–32

    Article  PubMed  CAS  Google Scholar 

  • Zwart R, Oortgiesen M, Vijverberg HPM (1994) Nitromethylene heterocycles: selective agonists of nicotinic receptors in locust neurons compared to mouse N1E-115 and BC3Hl cells. Pestic Biochem Physiol 48:202–213

    Article  Google Scholar 

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Authors and Affiliations

  1. Environmental Chemistry and Toxicology Laboratory, Department of Environmental Science, Policy and Management, University of California, Berkeley, CA, 94720-3112, USA

    Motohiro Tomizawa, Bachir Latli & John E. Casida

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  1. Motohiro Tomizawa
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  2. Bachir Latli
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  3. John E. Casida
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Editors and Affiliations

  1. Tokyo University of Agriculture, 1-1 Sakuragaoka 1, Setagaya-ku, Tokyo, 156-8502, Japan

    Izuru Yamamoto (Professor Emeritus) (Professor Emeritus)

  2. University of California, Berkeley, California, 94720-3112, USA

    John E. Casida (Professor of Entomology and Director of Environmental Chemistry and Toxicology Laboratory) (Professor of Entomology and Director of Environmental Chemistry and Toxicology Laboratory)

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© 1999 Springer Japan

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Tomizawa, M., Latli, B., Casida, J.E. (1999). Structure and Function of Insect Nicotinic Acetylcholine Receptors Studied with Nicotinoid Insecticide Affinity Probes. In: Yamamoto, I., Casida, J.E. (eds) Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor. Springer, Tokyo. https://doi.org/10.1007/978-4-431-67933-2_13

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  • DOI: https://doi.org/10.1007/978-4-431-67933-2_13

  • Publisher Name: Springer, Tokyo

  • Print ISBN: 978-4-431-68011-6

  • Online ISBN: 978-4-431-67933-2

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