Cited by 945Nicotinic Acetylcholine Receptors StudyPesticide Exposure and ToxicityInsect Resistance and Genetics

The DOI matches its Crossref record.

Neonicotinoids: insecticides acting on insect nicotinic acetylcholine receptors

Abstract

Imidacloprid is increasingly used worldwide as an insecticide. It is an agonist at nicotinic acetylcholine receptors (nAChRs) and shows selective toxicity for insects over vertebrates. Recent studies using binding assays, molecular biology and electrophysiology suggest that both alpha- and non-alpha-subunits of nAChRs contribute to interactions of these receptors with imidacloprid. Electrostatic interactions of the nitroimine group and bridgehead nitrogen in imidacloprid with particular nAChR amino acid residues are likely to have key roles in determining the selective toxicity of imidacloprid. Chemical calculation of atomic charges of the insecticide molecule and a site-directed mutagenesis study support this hypothesis.

Overview

Integrity signals

Registry

Crossref · 10.1016/s0165-6147(00)01820-4

Cites

Statistics

Recomputing p-values needs the paper’s full text.

Verification

Claims the paper makes

We couldn’t retrieve this paper’s full text, so its claims and self-check weren’t run. The registry and citation checks still apply.

Claims other papers make about this one

Each is checked against this paper’s own text: does it say what the citing paper says it does?

Citations

Cites

No references could be resolved yet.

Research works printed but not linked: 56

  1. Mullins, 1993, Imidacloprid: a new nitroguanidine insecticide, ACS Symposium Series, 254, 183, 10.1021/bk-1993-0524.ch013 · DOI
  2. Kagabu, 1995, Stability comparison of imidacloprid and related compounds under simulated sunlight, hydrolysis conditions, and to oxygen, Biosci. Biotechnol. Biochem., 59, 980, 10.1271/bbb.59.980 · DOI
  3. Kagabu, 1997, Chloronicotinyl insecticides – discovery, application and future perspective, Rev. Toxicol., 1, 75
  4. Liu, 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, 10.1006/pest.1993.1051 · DOI
  5. Buckingham, 1995, Actions of nitromethylenes on an α-bungarotoxin-sensitive neuronal nicotinic acetylcholine receptor, Neuropharmacology, 34, 591, 10.1016/0028-3908(95)00024-Z · DOI
  6. McGehee, 1995, Physiological diversity of nicotinic acetylcholine receptors expressed by vertebrate neurons, Annu. Rev. Physiol., 57, 521, 10.1146/annurev.ph.57.030195.002513 · DOI · Paper page
  7. Elgoyhen, 1994, α9: an acetylcholine receptor with novel pharmacological properties expressed in rat cochlear hair cells, Cell, 79, 705, 10.1016/0092-8674(94)90555-X · DOI
  8. Elgoyhen, 2001, α10: a determinant of nicotinic cholinergic receptor function in mammalian vestibular and cochlear mechanosensory hair cells, Proc. Natl. Acad. Sci. U. S. A., 98, 3501, 10.1073/pnas.051622798 · DOI
  9. Breer, 1987, Molecular properties and functions of insect acetylcholine receptors, J. Insect Physiol., 33, 771, 10.1016/0022-1910(87)90025-4 · DOI
  10. Sattelle, 1990, Cholinergic nerve terminals in the central nervous system of insects. Molecular aspects of structure, function and regulation, J. Neuroendocrinol., 2, 241, 10.1111/j.1365-2826.1990.tb00400.x · DOI
  11. Gundelfinger, 1992, How complex is the nicotinic receptor system of insects?, Trends Neurosci., 15, 206, 10.1016/0166-2236(92)90035-7 · DOI
  12. Littleton, 2000, Ion channels and synaptic organization: analysis of the Drosophila genome, Neuron, 26, 35, 10.1016/S0896-6273(00)81135-6 · DOI
  13. Schroeder, 1984, The mode of action and neurotoxic properties of the nitromethylene heterocycle insecticides, Pestic. Biochem. Physiol., 22, 148, 10.1016/0048-3575(84)90084-1 · DOI
  14. Bai, 1991, Actions of imidacloprid and a related nitromethylene on cholinergic receptors of an identified insect motor neurone, Pestic. Sci., 33, 197, 10.1002/ps.2780330208 · DOI
  15. Tomizawa, 1992, Binding of nicotinoids and the related compounds to the insect nicotinic acetylcholine receptor, J. Pestic. Sci., 17, 231, 10.1584/jpestics.17.4_231 · DOI
  16. Tomizawa, 1993, Structure–activity relationships of nicotinoids and imidacloprid analogs, J. Pestic. Sci., 18, 91, 10.1584/jpestics.18.91 · DOI
  17. Liu, 1993, High affinity binding of [3H]imidacloprid in the insect acetylcholine receptor, Pestic. Biochem. Physiol., 46, 40, 10.1006/pest.1993.1034 · DOI
  18. Tomizawa, 1996, Novel neonicotinoid-agarose affinity column for Drosophila and Musca nicotinic acetylcholine receptors, J. Neurochem., 67, 1669, 10.1046/j.1471-4159.1996.67041669.x · DOI
  19. Buckingham, 1997, Imidacloprid actions on insect neuronal acetylcholine receptors, J. Exp. Biol., 200, 2685, 10.1242/jeb.200.21.2685 · DOI
  20. Sattelle, 1989, Actions of the insecticide 2 (nitromethylene) tetrahydro-1,3-thiazine on insect and vertebrate nicotinic acetylcholine receptors, Proc. R. Soc. London Ser. B Biol. Sci., 237, 501, 10.1098/rspb.1989.0062 · DOI
  21. Benson, 1992, Electrophysiological pharmacology of the nicotinic and muscarinic cholinergic responses of isolated neuronal somata from locust thoracic ganglia, J. Exp. Biol., 170, 203, 10.1242/jeb.170.1.203 · DOI
  22. Leech, 1991, Nitromethylene actions on in situ and expressed insect nicotinic acetylcholine receptors, FEBS Lett., 290, 90, 10.1016/0014-5793(91)81233-X · DOI
  23. Cheung, 1992, A patch-clamp study of the action of a nitromethylene heterocycle insecticide on cockroach neurones growing in vitro, Pestic. Sci., 34, 187, 10.1002/ps.2780340302 · DOI
  24. Nagata, 1996, Subconductance-state currents generated by imidacloprid at the nicotinic acetylcholine receptor in PC 12 cells, NeuroReport, 7, 1025, 10.1097/00001756-199604100-00014 · DOI
  25. Nagata, 1998, Modulation of the neuronal nicotinic acetylcholine receptor-channel by the nitromethylene heterocycle imidacloprid, J. Pharmacol. Exp. Ther., 285, 731
  26. Zwart, 1992, The nitromethylene heterocycle 1-(pyridin-3-yl-methyl)-2-nitromethylene-imidazolidine distinguishes mammalian from insect nicotinic receptor subtypes, Eur. J. Pharmacol., 228, 165
  27. Zwart, 1994, Nitromethylene heterocycles: selective agonists of nicotinic receptors in locust neurons compared to mouse N1E-115 and BC3H1 cells, Pestic. Biochem. Physiol., 48, 202, 10.1006/pest.1994.1021 · DOI
  28. Yamamoto, 1995, Molecular mechanism for selective toxicity of nicotinoids and neonicotinoids, J. Pestic. Sci., 20, 33, 10.1584/jpestics.20.33 · DOI
  29. Marshall, 1990, Sequence and functional expression of a single α subunit of an insect nicotinic acetylcholine receptor, EMBO J., 9, 4391, 10.1002/j.1460-2075.1990.tb07889.x · DOI
  30. Hermsen, 1998, Neuronal nicotinic receptors in the locust Locusta migratoria, J. Biol. Chem., 273, 18394, 10.1074/jbc.273.29.18394 · DOI
  31. Bossy, 1988, Conservation of neural nicotinic acetylcholine receptors from Drosophila to vertebrate central nervous systems, EMBO J., 7, 611, 10.1002/j.1460-2075.1988.tb02854.x · DOI
  32. Baumann, 1990, Sequence of Dα2, a novel α-like subunit of Drosophila nicotinic acetylcholine receptors, Nucleic Acids Res., 18, 3640, 10.1093/nar/18.12.3640 · DOI
  33. Sawruk, 1990, Heterogeneity of Drosophila nicotinic acetylcholine receptors: SAD, a novel developmentally regulated α-subunit, EMBO J., 9, 2671, 10.1002/j.1460-2075.1990.tb07452.x · DOI
  34. Schulz, 1998, Dα3, a new functional α subunit of nicotinic acetylcholine receptors from Drosophila, J. Neurochem., 71, 853, 10.1046/j.1471-4159.1998.71020853.x · DOI
  35. Lansdell, 2000, Cloning and heterologous expression of Dα4, a Drosophila neuronal nicotinic acetylcholine receptor subunit: identification of an alternative exon influencing the efficiency of subunit assembly, Neuropharmacology, 39, 2604, 10.1016/S0028-3908(00)00111-8 · DOI
  36. Hermans-Borgmeyer, 1986, Primary structure of a developmentally regulated nicotinic acetylcholine receptor protein from Drosophila, EMBO J., 5, 1503, 10.1002/j.1460-2075.1986.tb04389.x · DOI
  37. Sawruk, 1990, SBD, a novel structural subunit of the Drosophila nicotinic acetylcholine receptor, shares its genomic localization with two α-subunits, FEBS Lett., 273, 177, 10.1016/0014-5793(90)81078-3 · DOI
  38. Eastham, 1998, Characterization of a nicotinic acetylcholine receptor from the insect Manduca sexta, Eur. J. Neurosci., 10, 879, 10.1046/j.1460-9568.1998.00095.x · DOI
  39. Sgard, 1998, Cloning and functional characterisation of two novel nicotinic acetylcholine receptor α subunits from the insect pest Myzus persicae, J. Neurochem., 71, 903, 10.1046/j.1471-4159.1998.71030903.x · DOI
  40. Huang, 1999, Molecular characterization and imidacloprid selectivity of nicotinic acetylcholine receptor subunits from the peach-potato aphid Myzus persicae, J. Neurochem., 73, 380, 10.1046/j.1471-4159.1999.0730380.x · DOI
  41. Huang, 2000, Cloning, heterologous expression and co-assembly of Mpβ1, a nicotinic acetylcholine receptor subunit from the aphid Myzus persicae, Neurosci. Lett., 284, 116, 10.1016/S0304-3940(00)00969-1 · DOI
  42. Bertrand, 1994, Physiological properties of neuronal nicotinic acetylcholine receptors reconstituted from the vertebrate β2 subunit and Drosophila α subunits, Eur. J. Neurosci., 6, 869, 10.1111/j.1460-9568.1994.tb00997.x · DOI
  43. Matsuda, 1998, Effects of the α subunit on imidacloprid sensitivity of recombinant nicotinic acetylcholine receptors, Br. J. Pharmacol., 123, 518, 10.1038/sj.bjp.0701618 · DOI
  44. Lansdell, 2000, The influence of nicotinic receptor subunit composition upon agonist, α-bungarotoxin and insecticide (imidacloprid) binding affinity, Neuropharmacology, 39, 671, 10.1016/S0028-3908(99)00170-7 · DOI
  45. Karlin, 1995, Toward a structural basis for the function of nicotinic acetylcholine receptors and their cousins, Neuron, 15, 1231, 10.1016/0896-6273(95)90004-7 · DOI
  46. Couturier, 1990, A neuronal nicotinic acetylcholine receptor subunit (α7) is developmentally regulated and forms a homo-oligomeric channel blocked by α-BTX, Neuron, 5, 847, 10.1016/0896-6273(90)90344-F · DOI
  47. Matsuda, 2000, Role of loop D of the α7 nicotinic acetylcholine receptor in its interaction with the insecticide imidacloprid and related neonicotinoids, Br. J. Pharmacol., 130, 981, 10.1038/sj.bjp.0703374 · DOI
  48. Arias, 1997, Topology of ligand binding sites on the nicotinic acetylcholine receptor, Brain Res. Rev., 25, 133, 10.1016/S0165-0173(97)00020-9 · DOI
  49. Corringer, 2000, Nicotinic receptors at the amino acid level, Annu. Rev. Pharmacol. Toxicol., 40, 431, 10.1146/annurev.pharmtox.40.1.431 · DOI
  50. Brejc, 2001, Crystal structure of an ACh-binding protein reveals the ligand-binding domain of nicotinic receptors, Nature, 411, 269, 10.1038/35077011 · DOI
  51. Smit, 2001, A glia-derived acetylcholine-binding protein that modulates synaptic transmission, Nature, 411, 261, 10.1038/35077000 · DOI
  52. Tomizawa, 2000, Neonicotinoid insecticides: molecular features conferring selectivity for insect versus mammalian nicotinic receptors, J. Agric. Food Chem., 48, 6016, 10.1021/jf000873c · DOI
  53. Kagabu, 1996, Studies on the synthesis and insecticidal activity of neonicotinoid compounds, J. Pestic. Sci., 21, 237, 10.1584/jpestics.21.231 · DOI
  54. Adams, 2000, The genome sequence of Drosophila melanogaster, Science, 287, 2185, 10.1126/science.287.5461.2185 · DOI
  55. Tsao, 1989, Chemical and photochemical transformation of the insecticide cartap hydrochloride into nereistoxin, J. Pestic. Sci., 14, 47, 10.1584/jpestics.14.47 · DOI
  56. Narahashi, 2000, Neuroreceptors and ion channels as the basis for drug action: past, present, and future, J. Pharmacol. Exp. Ther., 294, 1

Cited by

Sorted by citations

See all 945

Metadata

Authors
Matsuda, K., Buckingham, S. D., Kleier, D., Rauh, J. J., Grauso, M., & Sattelle, D. B.
Affiliations
  • Kindai University (JP)
  • Babraham Institute (GB)
  • DuPont (United States) (US)
  • University of Oxford (GB)
Corresponding author
Sattelle, David B.
Venue
Trends in Pharmacological Sciences
Publisher
Elsevier BV
Published
2001-11
Volume
22
Issue
11
Pages
573-580
ISSN
0165-6147 (ISSN-L)
OpenAlex
W2026963422
Cited by
945
References
0
Citations by year
2026: 39 · 2025: 37 · 2024: 50 · 2023: 46 · 2022: 52 · 2021: 65 · 2020: 73 · 2019: 61 · 2018: 54 · 2017: 51 · 2016: 58 · 2015: 40 · 2014: 44 · 2013: 28 · 2012: 43
FWCI
0.96
Type
journal article
Language
en
Open access
closed
Locations
  • Trends in Pharmacological Sciences (publishedVersion)
  • PubMed (publishedVersion)
  • Research Explorer (The University of Manchester) (publishedVersion)
  • HAL (submittedVersion)
  • UCL Discovery (University College London) (submittedVersion)
Topics
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Nicotinic Acetylcholine Receptors Study
  • Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Toxicology › Pesticide Exposure and Toxicity
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Insect Resistance and Genetics
Keywords
neonicotinoids, imidacloprid, nicotinic acetylcholine receptors, insecticide selectivity, alpha subunit, electrostatic interactions, site-directed mutagenesis, insecticide binding
MeSH terms
Animals, Humans, Insecticides, Receptors, Nicotinic, Structure-Activity Relationship, Cholinergic Agents

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review