Insecticidal and neural activities of candidate photoaffinity probes for neonicotinoid binding sites

Bioscience, Biotechnology and Biochemistry

Volumn 65, Issue 7, 2001, Pages 1534-1541

  Matsuda, Kazuhiko ^a   Ihara, Makoto ^a   Nishimura, Keiichiro ^b   Sattelle, David B ^c   Komai, Koichiro ^a  

^a KINKI UNIVERSITY   (Japan)

^b Osaka Prefecture University   (Japan)

^c UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Imidacloprid; Neonicotinoid; Nicotinic acetylcholine receptor; Photoaffinity probe; Trifluoromethyldiazirine

Indexed keywords

BLATTARIA; BLATTIDAE; GALLUS GALLUS; INSECTA;

ANABASINE; INSECTICIDE; NICOTINIC RECEPTOR;

ANIMAL; ARTICLE; BINDING SITE; CHEMISTRY; DROSOPHILA; DRUG EFFECT; FEMALE; GENETICS; IN VITRO STUDY; METABOLISM; NERVOUS SYSTEM; OOCYTE; PERIPLANETA; PHOTOAFFINITY LABELING; SYNTHESIS; XENOPUS LAEVIS;

ANABASINE; ANIMALS; BINDING SITES; DROSOPHILA; FEMALE; INSECTICIDES; NERVOUS SYSTEM; OOCYTES; PERIPLANETA; PHOTOAFFINITY LABELS; RECEPTORS, NICOTINIC; XENOPUS LAEVIS;

EID: 0035408664     PISSN: 09168451     EISSN: None     Source Type: Journal    
DOI: 10.1271/bbb.65.1534     Document Type: Article

References (32)

1. Kagabu, S., Chloronicotinyl insecticides - discovery, application and future perspective. Rev. Toxicol., 1, 75-129 (1997).
2. 3H]imidacloprid in the insect acetylcholine receptor. Pestic. Biochem. Physiol., 46, 40-46 (1993).
3. Zwart, R., Oortgiesen, M., and Vijverberg, H. P. M., Nitromethylene heterocycles: Selective agonists of nicotinic receptors in locust neurons compared to mouse N1E-115 and BC3H1 cells. Pestic. Biochem. Physiol., 48, 202-213 (1994).
4. Arias, H. R., Topology of ligand binding sites on the nicotinic acetylcholine receptor. Brain Res. Rev., 25, 13-191 (1997).
5. Karlin, A., and Akabas, M. H., Toward a structural basis for the function of nicotinic acetylcholine receptors and their cousins. Neuron, 15, 1231-1244 (1995).
6. Tomizawa, M., and Yamamoto I., Structure-activity relationships of neonicotinoids and imidacloprid analogues. J. Pestic. Sci., 18, 91-98 (1993).
7. Tomizawa, M., and Casida, J. E., Minor structural changes in nicotinoid insecticides confer differential subtype selectivity for mammalian nicotinic acetylcholine receptors. Br. J. Pharmacol., 127, 115-122 (1999).
8. Okazawa, A., Akamatsu, M., Ohoka, A., Nishiwaki, H., Cho, W.-J., Nakagawa, Y., Nishimura, K., and Ueno, T., Prediction of the binding mode of imidaloprid and related compounds to house-fly head acetylcholine receptors using three-dimensional QSAR analysis. Pestic. Sci., 54, 134-144 (1998).
9. Hermans-Borgmeyer, I., Zopf, D., Ryseck, R.-P., Hovemann, B., Betz, H., and Gundelfinger, E. D., Primary structure of a developmentally regulated nicotinic acetylcholine receptor protein from Drosophila. EMBO J., 5, 1503-1508 (1986).
10. Bossy, B., Ballivet, M., and Spierer, P., Conservation of neuronal nicotinic acetylcholine receptors from Drosophila to vertebrate central nervous systems. EMBO J., 7, 611-618 (1988).
11. Sawruk, E. Schloss, P., Betz, H., and Schmitt, B., Heterogeneity of Drosophila nicotinic acetylcholine receptors: SAD, a novel developmentally regulated α-subunit. EMBO J., 9, 2671-2677 (1990).
12. Sawruk, E., Udri, C., Betz, H., and Schmitt, B., SBD, a novel structural subunit of the Drosophila nicotinic acetylcholine receptor shares its genomic localization with two α-subunits. FEBS Lett., 273, 177-181 (1990).
13. Schulz, R., Sawruk, E., Mulhardt, C., Bertrand, S., Baumann, A., Phannavong, B., Betz, H., Bertrand, D., Gundelfinger, E. D., and Schmitt, B., Dα3, a new functional a subunit of nicotinic acetylcholine receptors from Drosophila. J. Neurochem., 71, 853-862 (1998).
14. Marshall, J., Buckingham, S. D., Shingai, R., Lunt, G. G., Goosey, M. W., Darlison, M. G., Sattelle, D. B., and Barnard, E. A., Sequence and functional expression of a single a subunit of an insect nicotinic acetylcholine receptor. EMBO J., 9, 4391-4398 (1990).
15. Hermsen, B., Stetzer, E., Thees, R., Heiermann, R., Schrattenholz, A., Ebbinghaus, U., Kretschmer, A., Methfessel, C., Reinhardt, S., and Maelicke, A., Neuronal nicotinic receptors in the locust Locusta migratoria. J. Biol. Chem., 273, 18394-18404 (1998).
16. Sgard, F., Fraser, S. P., Katkowska, M. J., Diamgoz, M. B. A., Dunbar, S. J., and Windass, J. D., Cloning and functional characterization of two novel nicotinic acetylcholine receptor a subunits from the insect Myzus persicae. J. Neurochem., 71, 903-912 (1998).
17. Huang Y., Williamson, M. S., Devonshire, A. L., Windass, J. D., Lansdell, S. J., and Millar, N. S., Molecular characterization and imidacloprid selectivity of nicotinic acetylcholine receptor subunits from the peach-potato aphid Myzus persicae. J. Neurochem., 73, 380-389 (1999).
18. Huang, Y., Williamson, M. S., Devonshire, A. L., Windass, J. D., Lansdell, S. J., and Millar, N. S., Cloning, heterologous expression and co-assembly of Mpβ1, a nicotinic acetylcholine receptor subunit from the aphid Myzus persicae. Neurosci. Lett., 284, 116-120 (2000).
19. Eastham, H. M., Lind, R. J., Eastlak, J. L., Clarke, B. S., Towner, P., Reynolds, S. E., Wolstenholme, A. J., and Wonnacott, S., Characterization of a nicotinic acetylcholine receptor from the insect Manduca sexta. Eur. J. Neurosci., 10, 879-889 (1998).
20. Bertrand, D., Ballivet, M., Gomez, M., Bertrand, S., Phannavong, B., and Gundelfinger, E. D., Physiological properties of neuronal nicotinic acetylcholine receptors reconstituted from the vertebrate β2 subunit and Drosophila α subunits. Eur. J. Neurosci., 6, 869-875 (1993).
21. Matsuda, K., Buckingham, S. D., Freeman, J. C., Squire, M. D., Baylis, H. A., and Sattelle, D. B., Effects of the a subunit on imidacloprid sensitivity of recombinant nicotinic acetylcholine receptors. Br. J. Pharmacol., 123, 518-524 (1998).
22. Lansdell, S. J., and Millar, N. S., The influence of nicotinic receptor subunit composition upon agonist, α-bungarotoxin and insecticide (imidacloprid) binding affinity. Neuropharmacology, 39, 671-679 (2000).
23. Matsuda, K., Shimomura, M., Kondo, Y., Ihara, M., Hashigami, K., Yoshida, N., Raymond, V., Mongan, N. P., Freeman, J. C., Komai, K., and Sattelle, D. B., Role of loop D of the α7 nicotinic acetylcholine receptor in its interaction with the insecticide imidacloprid and related neonicotinoids. Br. J. Pharmacol., 130, 981-986 (2000).
24. Nassal, M., 4′-(1-Azi-2,2,2-trifluoroethyl)phenylalanine, a photolabile carbene-generating analogue of phenylalanine. J. Am. Chem. Soc., 106, 7540-7545 (1984).
25. Matsuda, K., Hamada, M., Nishimura, K., and Fujita, T., Quantitative structure-activity studies of pyrethroids. 17. Physicochemical substituent effects of substituted benzyl esters of "kadethric" acid on symptomatic and neurophysiological activities. Pestic. Biochem, Physiol., 35, 300-314 (1989).
26. Nishimura, K., Kanda, Y., Okazawa, A., and Ueno, T., Relationship beween insecticidal and neurophysiological activities of imidacloprid and related compounds. Pestic. Biochem. Physiol., 50, 51-59 (1994).
27. Nishimura, K., Tanaka, M., Iwaya, K., and Kagabu, S., Relationship between insecticidal and nerve-excitatory activities of imidacloprid and its alkylated congeners at the imidazolidine NH site. Pestic. Biochem. Physiol., 62, 172-178 (1998).
28. Kiriyama, K., Iwaya, K., Kagabu, S., and Nishimura, K., Relationship between insecticidal and nerve activities of an imidacloprid-related nitromethylene compound and its N-substituted congeners. J. Pestic. Sci., 26, 55-59 (2001).
29. Buckingham, S. D., Hosie, A. M., Roush, R. T., and Sattelle, D. B., Actions of agonists and convulsant antagonists on a Drosophila melanogaster GABA receptor (Rdl) homo-oligomer expressed in Xenopus oocytes. Neurosci. Lett., 181, 137-140 (1994).
30. 125I]neonicotinoid photoaffinity probe for the Drosophila nicotinic acetylcholine receptor. Bioconjug. Chem., 8, 7-14 (1997).
31. 125I]Azidonicotinoid photoaffinity labeling of insecticide-binding subunit of Drosophila nicotinic acetylcholine receptor. Neurosci. Lett., 237, 61-64 (1997).
32. Bayley, H., Photogenerated reagents in biochemistry and molecular biology. In "Laboratory Techniques in Biochemistry and Molecular Biology," eds. Work, T. S., and Burdon, R. H., Elsevier, Amsterdam, pp. 25-44 (1983).