Selective Toxicity of Neonicotinoids Attributable to Specificity of Insect and Mammalian Nicotinic Receptors

Annual Review of Entomology

Volumn 48, Issue , 2003, Pages 339-364

  Tomizawa, Motohiro ^a   Casida, John E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Imidacloprid; Molecular features conferring selectivity; Neonicotinoid insecticides; Nicotine; Nicotinic acetylcholine receptor

Indexed keywords

CHEMICAL CONTROL; INSECTICIDE;

ANIMALIA; HEXAPODA; INSECTA; MAMMALIA;

ALKALOID; INSECTICIDE; NICOTINE; NICOTINIC RECEPTOR;

ANIMAL; BINDING SITE; CENTRAL NERVOUS SYSTEM; CHEMISTRY; DRUG EFFECT; DRUG RESISTANCE; IN VITRO STUDY; INSECT; MAMMAL; METABOLISM; PLANT; REVIEW; SPECIES DIFFERENCE;

ALKALOIDS; ANIMALS; BINDING SITES; CENTRAL NERVOUS SYSTEM; DRUG RESISTANCE; INSECTICIDES; INSECTS; MAMMALS; NICOTINE; PLANTS; RECEPTORS, NICOTINIC; SPECIES SPECIFICITY;

EID: 0037209233     PISSN: 00664170     EISSN: None     Source Type: Book Series    
DOI: 10.1146/annurev.ento.48.091801.112731     Document Type: Review

References (132)

1. Arias HR. 1997. Topology of ligand binding sites on the nicotinic acetylcholine receptor. Brain Res. Rev. 25:133-91
2. Arias HR. 2000. Localization of agonist and competitive antagonist binding sites on nicotinic acetylcholine receptors. Neurochem. Int. 36:595-645
3. Badio B, Daly JW. 1994. Epibatidine, a potent analgesic and nicotinic agonist. Mol. Pharmacol. 45:563-69
4. 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
5. 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. 6:869-75
6. Boëlle J, Schneider R, Gérardin P, Loubinoux B, Maienfisch P, Rindlisbacher A. 1998. Synthesis and insecticidal evaluation of imidacloprid analogs. Pestic. Sci. 54:304-7
7. Bossy B, Ballivet M, Spierer P. 1988. Conservation of neural nicotinic acetylcholine receptors from Drosophila to vertebrate central nervous systems. EMBO J. 7:611-18
8. Buckingham SD, Lapied B, Le Corronc H, Grolleau F, Sattelle DB. 1997. Imidacloprid actions on insect neuronal acetylcholine receptors. J. Exp. Biol. 200:2685-92
9. Cahill M, Denholm I. 1999. Managing resistance to the chloronicotinyl insecticides - rhetoric or reality? See Ref. 125, pp. 253-70
10. Cahill M, Gorman K, Day S, Denholm I, Elbert A, Nauen R. 1996. Baseline determination and detection of resistance to imidacloprid in Bemisia tabaci (Homoptera: Aleyrodidae). Bull. Entomol. Res. 86:343-49
11. Casida JE, Quistad GB. 1998. Golden age of insecticide research: past, present, or future? Annu. Rev. Entomol. 43:1-16
12. Chamaon K, Schulz R, Smalla K-H, Seidel B, Gundelfinger ED. 2000. Neuronal nicotinic acetylcholine receptors of Drosophila melanogaster: the α-subunit Dα3 and the β-subunit ARD co-assemble within the same receptor complex. FEBS Lett. 482:189-92
13. Chamaon K, Smalla K-H, Thomas U, Gundelfinger ED. 2002. Nicotinic acetylcholine receptors of Drosophila: three subunits encoded by genomically linked genes can co-assemble into the same receptor complex. J. Neurochem. 80:149-57
14. Chao S-L, 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
15. Chao S-L, Dennehy TJ, Casida JE. 1997. Whitefly (Hemiptera: Aleyrodidae) binding site for imidacloprid and related insecticides: a putative nicotinic acetylcholine receptor. J. Econ. Entomol. 90:879-82
16. Cordero-Erausquin M, Marubio LM, Klink R, Changeux J-P. 2000. Nicotinic receptor function: new perspectives from knockout mice. Trends Pharmacol. Sci. 21:211-17
17. Corringer J-P, Le Novère N, Changeux J-P. 2000. Nicotinic receptors at the amino acid level. Annu. Rev. Pharmacol. Toxicol. 40:431-58
18. Courjaret R, Lapied B. 2001. Complex intracellular messenger pathways regulate one type of neuronal α-bungarotoxin-resistant nicotinic acetylcholine receptors expressed in insect neurosecretory cells (dorsal unpaired median neurons). Mol. Pharmacol. 60:80-91
19. Daborn P, Boundy S, Yen J, Pittendrigh B, ffrench-Constant R. 2001. DDT resistance in Drosophila correlates with Cyp6g1 over-expression and confers cross-resistance to the neonicotinoid imidacloprid. Mol. Genet. Genomics 266:556-63
20. D'Amour KA, Casida JE. 1999. Desnitroimidacloprid and nicotine binding site in rat recombinant α4β2 neuronal nicotinic acetylcholine receptor. Pestic. Biochem. Physiol. 64:55-61
21. Eastham HM, Lind RJ, Eastlake JL, Clarke BS, Towner P, et al. 1998. Characterization of a nicotinic acetylcholine receptor from the insect Manduca sexta. Eur. J. Neurosci. 10:879-89
22. Elbert A, Buchholz A, Ebbinghaus-Kintscher U, Erdelen C, Nauen R, Schnorbach H-J. 2001. The biological profile of thiacloprid - a new chloronicotinyl insecticide. Pflanzenschutz-Nachr. Bayer 54:185-208
23. Eldefrawi AT, Bakry NM, Eldefrawi ME, Tsai M-C, Albuquerque AX. 1980. Nereistoxin interaction with the acetylcholine receptor-ionic channel complex. Mol. Pharmacol. 17:172-79
24. Elgoyhen AB, Vetter DE, Katz E, Rothlin CV, Heinemann SF, Boulter J. 2001. α10: a determinant of nicotinic cholinergic receptor function in mammalian vestibular and cochlear mechanosensory hair cells. Proc. Natl. Acad. Sci. USA 98:3501-6
25. Feuer H, Lawrence JP. 1969. The alkyl nitrate nitration of active methylene compounds. VI. A new synthesis of α-nitroalkyl heterocyclics. J. Am. Chem. Soc. 91:1856-57
26. Gundelfinger ED, Schulz R. 2000. Insect nicotinic acetylcholine receptors: genes, structure, physiological and pharmacological properties. In Handbook of Experimental Pharmacology. Vol. 144: Neuronal Nicotinic Receptors, ed. F Clementi, D Fornasari, C Gotti, pp. 497-521. Berlin: Springer
27. 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. 5:1503-8
28. Hermsen B, Stetzer E, Thees R, Heiermann R, Schrattenholz A, et al. 1998. Neuronal nicotinic receptors in the locust Locusta migratoria. J. Biol. Chem. 273:18394-404
29. Huang Y, Williamson MS, Devonshire AL, Windass JD, Lansdell SJ, Millar NS. 1999. Molecular characterization and imidacloprid sensitivity of nicotinic acetylcholine receptor subunits from the peachpotato aphid Myzus persicae. J. Neurochem. 73:380-89
30. Huang Y, Williamson MS, Devonshire AL, Windass JD, Lansdell SJ, Millar NS. 2000. Cloning, heterologous expression and co-assembly of Mpα1, a nicotinic acetylcholine receptor subunit from the aphid Myzus persicae. Neurosci. Lett. 284:116-20
31. Itier V, Bertrand D. 2001. Neuronal nicotinic receptors: from protein structure to function. FEBS Lett. 504:118-25
32. 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. 269:264-68
33. 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. 25:1494-508
34. Kagabu S. 1997. Chloronicotinyl insecticides - discovery, application and future perspective. Rev. Toxicol. 1:75-129
35. Kagabu S, Akagi T. 1997. Quantum chemical consideration of photostability of imidacloprid and related compounds. J. Pestic. Sci. 22:84-89
36. Kagabu S, Maienfisch P, Zhang A, Granda-Minones J, Haettenschwiler J, et al. 2000. 5-Azidoimidacloprid and an acyclic analogue as candidate photoaffinity probes for mammalian and insect nicotinic acetylcholine receptors. J. Med. Chem. 43:5003-9
37. Kagabu S, Matsuno H. 1997. Chloronicotinyl insecticides. 8. Crystal and molecular structures of imidacloprid and analogous compounds. J. Agric. Food Chem. 45:276-81
38. Kagabu S, Medej S. 1995. Stability comparison of imidacloprid and related compounds under simulated sunlight, hydrolysis conditions, and to oxygen. Biosci. Biotechnol. Biochem. 59:980-85
39. Kagabu S, Moriya K, Shibuya K, Hattori Y, Tsuboi S, Shiokawa K. 1992. 1-(6-Halonicotinyl)-2-nitromethylene-imidazolidines as potential new insecticides. Biosci. Biotechnol. Biochem. 56:362-63
40. Karlin A, Akabas MH. 1995. Toward a structural basis for the function of nicotinic acetylcholine receptors and their cousins. Neuron 15:1231-44
41. Kleier D, Holden I, Casida JE, Ruzo LO. 1985. Novel photoreactions of an insecticidal nitromethylene heterocycle. J. Agric. Food Chem. 33:998-1000
42. Klein O. 2001. Behaviour of thiacloprid (YRC 2894) in plants and animals. Pflanzenschutz-Nachr. Bayer 54:209-40
43. Kodaka K, Kinoshita K, Wakita T, Yamada E, Kawahara N, Yasui N. 1998. MTI-446: a novel systemic insect control compound. Proc. Brighton Crop Prot. Conf. Pests Dis. 1:21-26
44. Kollmeyer WD, Flattum RF, Foster JP, Powell JE, Schroeder ME, Soloway SB. 1999. Discovery of the nitromethylene heterocycle insecticides. See Ref. 125, pp. 71-89
45. Lansdell SJ, Millar NS. 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 39:2604-14
46. Lansdell SJ, Millar NS. 2000. The influence of nicotinic receptor subunit composition upon agonist, α-bungarotoxin and insecticide (imidacloprid) binding affinity. Neuropharmacology 39:671-79
47. Lansdell SJ, Schmitt B, Betz H, Sattelle DB, Millar NS. 1997. Temperature-sensitive expression of Drosophila neuronal nicotinic acetylcholine receptors. J. Neurochem. 68:1812-19
48. 3H]Imidacloprid: synthesis of a candidate radioligand for the nicotinic acetylcholine receptor. J. Label. Compd. Radiopharm. 31:609-13
49. Latli B, D'Amour KA, Casida JE. 1999. Novel and potent 6-chloro-3-pyridinyl ligands for the α4β2 neuronal nicotinic acetylcholine receptor. J. Med. Chem. 42:2227-34
50. 125I]neonicotinoid photoaffinity probe for the Drosophila nicotinic acetylcholine receptor. Bioconjug. Chem. 8:7-14
51. 3H] Imidacloprid labels high-and low-affinity nicotinic acetylcholine receptor-like binding sites in the aphid Myzus persicae (Hemiptera: Aphididae). Pestic. Biochem. Physiol. 62:3-14
52. Lindstrom J. 1997. Nicotinic acetylcholine receptors in health and disease. Mol. Neurobiol. 15:193-222
53. Littleton JT, Ganetzky B. 2000. Ion channels and synaptic organization: analysis of the Drosophila genome. Neuron 26:35-43
54. 3H] imidacloprid in the insect acetylcholine receptor. Pestic. Biochem. Physiol. 46:40-46
55. 3H] imidacloprid binding site in house fly head acetylcholine receptor to insecticidal activity of 2-nitromethylene-and 2-nitroimino-imidazolidines. Pestic. Biochem. Physiol. 46:200-6
56. Lloyd GK, Williams M. 2000. Neuronal nicotinic acetylcholine receptors as novel drug targets. J. Pharmacol. Exp. Ther. 292:461-67
57. Maienfisch P, Angst M, Brandl F, Fischer W, Hofer D, et al. 2001. Chemistry and biology of thiamethoxam: a second generation neonicotinoid. Pest Manage. Sci. 57:906-13
58. Maienfisch P, Brandi F, Kobel W, Rindlisbacher A, Senn R. 1999. CGA 293'343: a novel, broad-spectrum neonicotinoid insecticide. See Ref. 125, pp. 177-209
59. Marshall J, Buckingham SD, Shingai R, Lunt GG, Goosey MW, et al. 1990. Sequence and functional expression of a single α subunit of an insect nicotinic acetylcholine receptor. EMBO J. 9:4391-98
60. Matsuda K, Buckingham SD, Freeman JC, Squire MD, Baylis HA, Sattelle DB. 1998. Effects of the α subunit on imidacloprid sensitivity of recombinant nicotinic acetylcholine receptors. Br. J. Pharmacol. 123:518-24
61. Matsuda K, Buckingham SD, Kleier D, Rauh JJ, Grauso M, Sattelle DB. 2001. Neonicotinoids: insecticides acting on insect nicotinic acetylcholine receptors. Trends Pharmacol. Sci. 22:573-80
62. Minamida I, Iwanaga K, Tabuchi T, Aoki I, Fusaka T, et al. 1993. Synthesis and insecticidal activity of acyclic nitroethene compounds containing a heteroarylmethylamino group. J. Pestic. Sci. 18:41-48
63. Mitsui Toatsu Kagaku. 1996. Jpn. Kokai Tokkyo Koho JP8-48683
64. Mori K, Okumoto T, Kawahara N, Ozoe Y. 2002. Interaction of dinotefuran and its analogues with nicotinic acetylcholine receptors of cockroach nerve cords. Pest Manage. Sci. 58:190-96
65. Moriya K, Shibuya K, Hattori Y, Tsuboi S, Shiokawa K, Kagabu S. 1992. 1-(6-Chloronicotinyl)-2-nitroimino-imidazolidines and related compounds as potential new insecticides. Biosci. Biotechnol. Biochem. 56:364-65
66. Nagata K, Aistrup GL, Song JH, Narahashi T. 1996. Subconductance-state currents generated by imidacloprid at the nicotinic acetylcholine receptor of PC 12 cells. NeuroReport 7:1025-28
67. Nakayama A, Sukekawa M. 1998. Quantitative correlation between molecular similarity and receptor-binding activity of neonicotinoid insecticides. Pestic. Sci. 52:104-10
68. Nauen R, Ebbinghaus-Kintscher U, Elbert A, Jeschke P, Tietjen K. 2001. Acetylcholine receptors as sites for developing neonicotinoid insecticides. In Biochemical Sites of Insecticide Action and Resistance, ed. I Ishaaya, pp. 77-105. Berlin: Springer-Verlag
69. Nauen R, Ebbinghaus-Kintscher U, Schmuck R. 2001. Toxicity and nicotinic acetylcholine receptor interaction of imidacloprid and its metabolites in Apis mellifera (Hymenoptera: Apidae). Pest Manage. Sci. 57:577-86
70. Nauen R, Elbert A. 1997. Apparent tolerance of a field-collected strain of Myzus nicotianae to imidacloprid due to strong antifeeding responses. Pestic. Sci. 49:252-58
71. Nauen R, Hungenberg H, Tollo B, Tietjen K, Elbert A. 1998. Antifeedant effect, biological efficacy and high affinity binding of imidacloprid to acetylcholine receptors in Myzus persicae and Myzus nicotianae. Pestic. Sci. 53:133-40
72. Nauen R, Reckmann U, Armborst S, Stupp H-P, Elbert A. 1999. Whitefly-active metabolites of imidacloprid: biological efficacy and translocation in cotton plants. Pestic. Sci. 55:265-71
73. Nauen R, Strobel J, Tietjen K, Otsu Y, Erdelen C, Elbert A. 1996. Aphicidal activity of imidacloprid against a tobacco feeding strain of Myzus persicae (Homoptera: Aphididae) from Japan closely related to Myzus nicotianae and highly resistant to carbamates and organophosphates. Bull. Entomol. Res. 86:165-71
74. Nauen R, Tietjen K, Wagner K, Elbert A. 1998. Efficacy of plant metabolites of imidacloprid against Myzus persicae and Aphis gossypii (Homoptera: Aphididae). Pestic. Sci. 52:53-57
75. 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
76. O'Brien RD. 1967. Insecticides: Action and Metabolism. New York: Academic. 332pp.
77. Okazawa A, Akamatsu M, Ohoka A, Nishiwaki H, Cho W-J, et al. 1998. Prediction of the binding mode of imidacloprid and related compounds to house-fly head acetylcholine receptors using three-dimensional QSAR analysis. Pestic. Sci. 54:134-44
78. Olson ER, Dively GP, Nelson JO. 2000. Baseline susceptibility to imidacloprid and cross resistance patterns in Colorado potato beetle (Coleptera: Chrysomelidae) populations. J. Econ. Entomol. 93:447-58
79. Paterson D, Nordberg A. 2000. Neuronal nicotinic receptors in the human brain. Prog. Neurobiol. 61:75-111
80. Prabhaker N, Toscano NC, Castle SJ, Henneberry TJ. 1997. Selection of imidacloprid resistance in silverleaf whiteflies from the Imperial Valley and development of a hydroponic bioassay for resistance monitoring. Pestic. Sci. 51:419-28
81. Reed WT, Erlam GJ. 1978. The house fly metabolism of nitromethylene insecticides. See Ref. 93a, pp. 159-169
82. Roberts TR, Hutson DH, eds. 1999. Metabolic Pathways of Agrochemicals. Pt. 2: Insecticides and Fungicides. Cambridge, UK: R. Soc. Chem. 1475 pp.
83. Sakai M. 1967. Studies on the insecticidal action of nereistoxin, 4-N,N,-dimethylamino-1,2,-dithiolane. V. Blocking action on the cockroach ganglion. Botyu-Kagaku 32:21-33
84. Sattelle DB, Buckingham SD, Wafford KA, Sherby SM, Bakry NM, et al. 1989. Actions of the insecticide 2(nitromethylene)tetrahydro-1,3-thiazine on insect and vertebrate nicotinic acetylcholine receptors. Proc. R. Soc. London Ser. B 237:501-14
85. Sawruk E, Schloss P, Betz H, Schmitt B. 1990. Heterogeneity of Drosophila nicotinic acetylcholine receptors: SAD, a novel developmentally regulated α-subunit. EMBO J. 9:2671-77
86. Sawruk E, Udri C, Betz H, Schmitt B. 1990. SBD, a novel structural subunit of the Drosophila nicotinic acetylcholine receptor, shares its genomic localization with two α-subunits. FEBS Lett. 273:177-81
87. Schroeder ME, Flattum RF. 1984. The mode of action and neurotoxic properties of the nitromethylene heterocycle insecticides. Pestic. Biochem. Physiol. 22:148-60
88. Schulz R, Bertrand S, Chamaon K, Smalla K-H, Gundelfinger ED, Bertrand D. 2000. Neuronal nicotinic acetylcholine receptors from Drosophila: two different types of α subunits coassemble within the same receptor complex. J. Neurochem. 74:2537-46
89. Schulz R, Sawruk E, Mülhardt C, Bertrand S, Baumann A, et al. 1998. Dα3, a new functional α subunit of nicotinic acetylcholine receptors from Drosophila. J. Neurochem. 71:853-62
90. Schulz-Jander D, Casida JE. 2002. Imidacloprid insecticide metabolism: human cytochrome P450 isozymes differ in selectivity for imidazolidine oxidation versus nitroimine reduction. Toxicol. Lett. 132:65-70
91. Schulz-Jander DA, Leimkuehler WM, Casida JE. 2002. Neonicotinoid insecticides: reduction and cleavage of imidacloprid nitroimine substituent by liver microsomal and cytosolic enzymes. Chem. Res. Toxicol. 15:1158-65
92. 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. 335:149-62
93. Sgard F, Fraser SP, Katkowska MJ, Djamgoz MBA, Dunbar SJ, Windass JD. 1998. Cloning and functional characterization of two novel nicotinic acetylcholine receptor a subunits from the insect pest Myzus persicae. J. Neurochem. 71:903-12
94. Shankland DL, Hollingworth RM, Smyth T Jr, eds. 1978. Pesticide and Venom Neurotoxicity. New York: Plenum
95. Sheets LP. 2001. Imidacloprid: a neonicotinoid insecticide. In Handbook of Pesticide Toxicology, Vol. 2, ed. R Krieger, pp. 1123-30. San Diego: Academic
96. Sheets LP. 2002. The neonicotinoid insecticides. In Handbook of Neurotoxicology, Vol. 1, ed. EJ Massaro, pp. 79-87. Totowa, NJ: Humana
97. Sherby SM, Eldefrawi AT, David JA, Sattelle DB, Eldefrawi ME. 1986 Interactions of charatoxins and nereistoxin with the nicotinic acetylcholine-receptors of insect CNS and Torpedo electric organ. Arch. Insect Biochem. Physiol. 3:431-45
98. Shiokawa K, Moriya K, Shibuya K, Hattori Y, Tsuboi S, Kagabu S. 1992. 3-(-6-Chloronicotinyl)-2-nitromethylenethiazolidine as a new class of insecticide acting against Lepidoptera species. Biosci. Biotechnol. Biochem. 56:1364-65
99. Shiokawa K, Tsuboi S, Kagabu S, Sasaki S, Moriya K, Hattori Y. 1987. Jpn. Kokai Tokkyo Koho JP62-207266
100. Soloway SB, Henry AC, Kollmeyer WD, Padgett WM, Powell JE, et al. 1978. Nitromethylene heterocycles as insecticides. See Ref. 93a, pp. 153-58
101. Soloway SB, Henry AC, Kollmeyer WD, Padgett WM, Powell JE, et al. 1979. Nitromethylene insecticides. In Advances in Pesticide Science, Vol. 2, ed. H Geissbüehler, pp. 206-17. Oxford: Pergamon
102. Spande TF, Garraffo HM, Edwards MW, Yeh HJC, Pannell L, Daly JW. 1992. Epibatidine: a novel (chloropyridyl)azabicycloheptane with potent analgesic activity from Ecuadorean poison frog. J. Am. Chem. Soc. 114:3475-78
103. Takahashi H, Mitsui J, Takakusa N, Matsuda M, Yoneda H, et al. 1992. NI-25, a new type of synthetic and broad spectrum insecticide. Proc. Brighton Crop Prot. Conf. Pest Dis. 1:89-96
104. Tassonyi E, Charpantier E, Muller D, Dumont L, Bertrand D. 2002. The role of nicotinic acetylcholine receptors in the mechanisms of anesthesia. Brain Res. Bull. 57:133-50
105. 125I]Azidonicotinoid photoaffinity labeling of insecticide-binding subunit of Drosophila nicotinic acetylcholine receptor. Neurosci. Lett. 237:61-64
106. Tomizawa M, Casida JE. 1999. Minor structural changes in nicotinoid insecticides confer differential subtype selectivity for mammalian nicotinic acetylcholine receptors. Br. J. Pharmacol. 127:115-22
107. Tomizawa M, Casida JE. 2000. Imidacloprid, thiacloprid, and their imine derivatives up-regulate the α4β2 nicotinic acetylcholine receptor in M10 cells. Toxicol. Appl. Pharmacol. 169:114-20
108. Tomizawa M, Casida JE. 2001. Structure and diversity of insect nicotinic acetylcholine receptors. Pest Manage. Sci. 57:914-22
109. Tomizawa M, Cowan A, Casida JE. 2001. Analgesic and toxic effects of neonicotinoid insecticides in mice. Toxicol. Appl. Pharmacol. 177:77-83
110. Tomizawa M, Latli B, Casida JE. 1996. Novel neonicotinoid-agarose affinity column for Drosophila and Musca nicotinic acetylcholine receptors. J. Neurochem. 67:1669-76
111. Tomizawa M, Latli B, Casida JE. 1999. Structure and function of insect nicotinic acetylcholine receptors studied with nicotinoid insecticide affinity probes. See Ref. 125, pp. 271-92
112. Tomizawa M, Lee DL, Casida JE. 2000. Neonicotinoid insecticides: molecular features conferring selectivity for insect versus mammalian nicotinic receptors. J. Agric. Food. Chem. 48:6016-24
113. Tomizawa M, Otsuka H, Miyamoto T, Eldefrawi ME, Yamamoto I. 1995. Pharmacological characteristics of insect nicotinic acetylcholine receptor with its ion channel and comparison of the effect of nicotinoids and neonicotinoids. J. Pestic. Sci. 20:57-64
114. Tomizawa M, Otsuka H, Miyamoto T, Yamamoto I. 1995. 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
115. 3H]azidoneonicotinoid. J. Neurochem. 78:1359-66
116. Tomizawa M, Yamamoto I. 1992. Binding of nicotinoids and the related compounds to the insect nicotinic acetylcholine receptor. J. Pestic. Sci. 17:231-36
117. Tomizawa M, Yamamoto I. 1993. Structure-activity relationships of nicotinoids and imidacloprid analogs. J. Pestic. Sci. 18:91-98
118. Ujiváry I. 1999. Nicotine and other insecticidal alkaloids. See Ref. 125, pp. 29-69
119. Ujiváry I. 2001. Pest control agents from natural products. In Handbook of Pesticide Toxicology. Vol. 1: Principles, ed. RI Krieger, pp. 109-79. San Diego: Academic
120. Uneme H, Iwanaga K, Higuchi N, Kando Y, Okauchi T, et al. 1998. Synthesis and insecticidal activity of nitroguanidine derivatives. 9th IUPAC Congr. Pestic. Chem. 1:ID-009 (Abstr.)
121. Wen Z, Scott JG. 1997. Cross-resistance to imidacloprid in strains of German cockroach (Blattella germanica) and house fly (Musca domestica). Pestic. Sci. 49:367-71
122. Wiesner P, Kayser H. 2000. Characterization of nicotinic acetylcholine receptors from the insects Aphis craccivora, Myzus persicae and Locusta migratoria by radioligand binding assays: relation to thiamethoxam action. J. Biochem. Mol. Toxicol. 14:221-30
123. Yamada T, Takahashi H, Hatano R. 1999. A novel insecticide, acetamiprid. See Ref. 125, pp. 149-76
124. Yamamoto I. 1965. Nicotinoids as insecticides. In Advances in Pest Control Research, Vol. 6, ed. RL Metcalf, pp. 231-60. New York: Wiley
125. Yamamoto I. 1999. Nicotine to nicotinoids: 1962 to 1997. See Ref. 125, pp. 3-27
126. Yamamoto I, Casida JE, eds. 1999. Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor. Tokyo: Springer-Verlag. 300 pp.
127. 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
128. Yamamoto I, Yabuta G, Tomizawa M, Saito T, Miyamoto T, Kagabu S. 1995. Molecular mechanism for selective toxicity of nicotinoids and neonicotinoids. J. Pestic. Sci. 20:33-40
129. 3H]imidacloprid binding site. J. Neurochem. 75:1294-303
130. Zhao J-Z, Bishop BA, Grafius EJ. 2000. Inheritance and synergism of resistance to imidacloprid in the Colorado potato beetle (Coleoptera: Chrysomelidae). J. Econ. Entomol. 93:1508-14
131. Zhong W, Gallivan JP, Zhang Y, Li L, Lester HA, Dougherty DA. 1998. From ab initio quantum mechanics to molecular neurobiology: a cation-π binding site in the nicotinic receptor. Proc. Natl. Acad. Sci. USA 95:12088-93
132. Zwart R, Oortgiesen M, Vijverberg HPM. 1994. Nitromethylene heterocycles: selective agonists of nicotinic receptors in locust neurons compared to mouse N1E-115 and BC3H1 cells. Pestic. Biochem. Physiol. 48:202-13