Modelling insecticide-binding sites in the voltage-gated sodium channel

Biochemical Journal

Volumn 396, Issue 2, 2006, Pages 255-263

  O'Reilly, Andrias O ^a   Khambay, Bhupinder P S ^b   Williamson, Martin S ^b   Field, Linda M ^b   Wallace, B A ^a   Davies, T G Emyr ^b  

^a UNIVERSITY OF LONDON   (United Kingdom)

^b ROTHAMSTED RESEARCH   (United Kingdom)

Author keywords

1,1,1 Trichloro 2,2 bis(p chlorophenyl)ethane(DDT); Docking; Knockdown resistance (kdr); Molecular modelling; Pyrethroids; Sodium channel

Indexed keywords

BINDING ENERGY; CONFORMATIONS; HYDROPHOBICITY; MATHEMATICAL MODELS; MUTAGENESIS; SODIUM COMPOUNDS;

1,1,1-TRICHLORO-2,2-BIS(P-CHLOROPHENYL)ETHANE(DDT); KNOCKDOWN RESISTANCE (KDR); MOLECULAR MODELING; PYRETHROIDS; SODIUM CHANNEL;

INSECTICIDES;

CHLORPHENOTANE; FENVALERATE; INSECTICIDE; ORGANOCHLORINE DERIVATIVE; PYRETHROID; VOLTAGE GATED SODIUM CHANNEL;

AMINO ACID SEQUENCE; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARACHNID; ARTHROPOD; ARTICLE; BINDING SITE; CHEMICAL MODEL; DNA TEMPLATE; HOUSE FLY; HYDROPHOBICITY; LIPID BILAYER; MUTATION; NONHUMAN; PRIORITY JOURNAL; PROTEIN CONFORMATION; PROTEIN DOMAIN; RAT; RESIDUE ANALYSIS; SEQUENCE ALIGNMENT; SEQUENCE ANALYSIS; SODIUM CURRENT; SPECIES COMPARISON; STRUCTURE ACTIVITY RELATION;

AMINO ACID SEQUENCE; ANIMALS; ARACHNIDA; BINDING SITES; DDT; HOUSEFLIES; HUMANS; INSECTICIDE RESISTANCE; INSECTICIDES; KV1.2 POTASSIUM CHANNEL; LIGANDS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; MUTATION; NITRILES; PROTEIN CONFORMATION; PYRETHRINS; SEQUENCE ALIGNMENT; SODIUM CHANNELS; STRUCTURE-ACTIVITY RELATIONSHIP;

ARTHROPODA;

EID: 33744809781     PISSN: 02646021     EISSN: None     Source Type: Journal    
DOI: 10.1042/BJ20051925     Document Type: Article

References (47)

1. Wang, S. Y. and Wang, G. K. (2003) Voltage-gated sodium channels as primary targets of diverse lipid-soluble neurotoxins. Cell. Signalling 15, 151-159
2. Catterall, W. A. (1980) Neurotoxins that act on voltage-sensitive sodium-channels in excitable-membranes. Annu. Rev. Pharmacol. Toxicol. 20, 15-43
3. Trainer, V. L., McPhee, J. C., Boutelet-Bochan, H., Baker, C., Scheuer, T., Babin, D., Demoute, J. P., Guedin, D. and Catterall, W. A. (1997) High affinity binding of pyrethroids to the α-subunit of brain sodium channels. Mol. Pharmacol. 51, 651-657
4. Leibowitz, M. D., Schwarz, J. R., Holan, G. and Hille, B. (1986) Distinct modifications of sodium channels by alkaloids and insecticides. Biophys. J. 49, A43
5. Salgado, V. L. and Narahashi, T. (1993) Immobilization of sodium-channel gating charge in crayfish giant-axons by the insecticide fenvalerate. Mol. Pharmacol. 43, 626-634
6. Vijverberg, H. P. and van den Bercken, J. (1990) Neurotoxicological effects and the mode of action of pyrethroid insecticides. Crit. Rev. Toxicol. 21, 105-126
7. Bloomquist, J. R. (1996) Ion channels as targets for insecticides. Annu. Rev. Entomol. 41, 163-190
8. Vais, H., Williamson, M. S., Devonshire, A. L. and Usherwood, P. N. R. (2001) The molecular interactions of pyrethroid insecticides with insect and mammalian sodium channels. Pest Manag. Sci. 57, 877-888
9. Soderlund, D. M. and Knipple, D. C. (2003) The molecular biology of knockdown resistance to pyrethroid insecticides. Insect Biochem. Mol. Biol. 33, 563-577
10. Williamson, M. S., Martinez-Torres, D., Hick, C. A. and Devonshire, A. L. (1996) Identification of mutations in the housefly para-type sodium channel gene associated with knockdown resistance (kdr) to pyrethroid insecticides. Mol. Gen. Genet. 252, 51-60
11. Park, Y. and Taylor, M. F. J. (1997) A novel mutation L1029H in sodium channel gene hscp associated with pyrethroid resistance for Heliothis virescens (Lepidoptera: Noctuidae). Insect Biochem. Mol. Biol. 27, 9-13
12. Ranson, H., Jensen, B., Vulule, J. M., Wang, X., Hemingway, J. and Collins, F. H. (2000) Identification of a point mutation in the voltage-gated sodium channel gene of Kenyan Anopheles gambiae associated with resistance to DDT and pyrethroids. Insect Mol. Biol. 9, 491-497
13. Morin, S., Williamson, M. S., Goodson, S. J., Brown, J. K., Tabashnik, B. E. and Dennehy, T. J. (2002) Mutations in the Bemisia tabaci para sodium channel gene associated with resistance to a pyrethroid plus organophosphate mixture. Insect Biochem. Mol. Biol. 32, 1781-1791
14. Lee, S. H., Yoon, K. S., Williamson, M. S., Goodson, S. J., Takano-Lee, M., Edman, J. D., Devonshire, A. L. and Clark, J. M. (2000) Molecular analysis of kdr-like resistance in permethrin-resistant strains of head lice, Pediculus capitis. Pest. Biochem. Physiol. 66, 130-143
15. Schuler, T. H., Martinez-Torres, D., Thompson, A. J., Denholm, I., Devonshire, A. L., Duce, I. R. and Williamson, M. S. (1998) Toxicological, electrophysiological, and molecular characterisation of knockdown resistance to pyrethroid insecticides in the diamondback moth, Plutella xylostella (L.). Pest. Biochem. Physiol. 59, 169-182
16. Bass, C., Schroeder, I., Turberg, A., Field, L. M. and Williamson, M. S. (2004) Identification of mutations associated with pyrethroid resistance in the para-type sodium channel of the cat flea, Ctenocephalides felis. Insect Biochem. Mol. Biol. 34, 1305-1313
17. Usherwood, P. N. R., Vais, H., Khambay, B. P. S., Davies, T. G. E. and Williamson, M. S. (2005) Sensitivity of the Drosophila para sodium channel to DDT is not lowered by the super-kdr mutation M918T on the IIS4-S5 linker that profoundly reduces sensitivity to permethrin and deltamethrin. FEBS Lett. 579, 6317-6325
18. Vais, H., Atkinson, S., Eldursi, N., Devonshire, A. L., Williamson, M. S. and Usherwood, P. N. R. (2000) A single amino acid change makes a rat neuronal sodium channel highly sensitive to pyrethroid insecticides. FEBS Lett. 470, 135-138
19. Lee, S. H. and Soderlund, D. M. (2001) The V410M mutation associated with pyrethroid resistance in Heliothis virescens reduces the pyrethroid sensitivity of housefly sodium channels expressed in Xenopus oocytes. Insect Biochem. Mol. Biol. 31, 19-29
20. Tan, J. G., Liu, Z. Q., Wang, R. W., Huang, Z. Y., Chen, A. C., Gurevitz, M. and Dong, K. (2005) Identification of amino acid residues in the insect sodium channel critical for pyrethroid binding. Mol. Pharmacol. 67, 513-522
21. Cronin, N. B., O'Reilly, A., Duclohier, H. and Wallace, B. A. (2003) Binding of the anticonvulsant drug lamotrigine and the neurotoxin batrachotoxin to voltage-gated sodium channels induces conformational changes associated with block and steady-state activation. J. Biol. Chem. 278, 10675-10682
22. Long, S. B., Campbell, E. B. and MacKinnon, R. (2005) Crystal structure of a mammalian voltage-dependent Shaker family K+ channel. Science (Washington, DC) 309, 897-903
23. Long, S. B., Campbell, E. B. and MacKinnon, R. (2005) Voltage sensor of Kv1.2: Structural basis of electromechanical coupling. Science (Washington, DC) 309, 903-908
24. + channel. Nature (London) 423, 33-41
25. CCP4 (1994) The CCP4 suite: programs for protein crystallography. Acta Crystallogr. Sect. D Biol. Crystallogr. 50, 760-763
26. Thompson, J. D., Higgins, D. G. and Gibson, T. J. (1994) CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res. 22, 4673-4680
27. Clark, M., Cramer, R. D. and Van Opdenbosch, N. (1989) Validation of the general-purpose Tripos 5.2 force-field. J. Comput. Chem. 10, 982-1012
28. Gasteiger, J. and Marsili, M. (1980) Iterative partial equalization of orbital electronegativity - a rapid access to atomic charges. Tetrahedron 36, 3219-3228
29. Goodsell, D. S., Morris, G. M. and Olson, A. J. (1996) Automated docking of flexible ligands: Applications of AutoDock. J. Mol. Recognit. 9, 1-5
30. Morris, G. M., Goodsell, D. S., Halliday, R. S., Huey, R., Hart, W. E., Belew, R. K. and Olson, A. J. (1998) Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J. Comput. Chem. 19, 1639-1662
31. Aggarwal, S. K. and MacKinnon, R. (1996) Contribution of the S4 segment to gating charge in the Shaker K+ channel. Neuron 16, 1169-1177
32. Ding, S. H., Ingleby, L., Ahern, C. A. and Horn, R. (2005) Investigating the putative glycine hinge in Shaker potassium channel. J. Gen. Physiol. 126, 213-226
33. Sali, D., Bycroft, M. and Fersht, A. R. (1988) Stabilization of protein structure by interaction of alpha-helix dipole with a charged side-chain. Nature (London) 335, 740-743
34. Doyle, D. A., Cabral, J. M., Pfuetzner, R. A., Kuo, A. L., Gulbis, J. M., Cohen, S. L., Chait, B. T. and MacKinnon, R. (1998) The structure of the potassium channel: Molecular basis of K+ conduction and selectivity. Science (Washington, DC) 280, 69-77
35. Yamagishi, T., Li, R. A., Hsu, K., Marban, E. and Tomaselli, G. F. (2001) Molecular architecture of the voltage-dependent sodium channel: Functional evidence for α-helices in the pore. J. Gen. Physiol. 118, 171-181
36. Elliott, M., Farnham, H., Janes, N. F., Needham, P. H. and Pulman, D. A. (1974) Insecticidally active conformations of pyrethroids. In Mechanisms of Pesticide Action (Kohn, G. K., ed.), pp. 81-91. American Chemical Society, Washington DC
37. Meyer, E. A., Castellano, R. K. and Diederich, F. (2003) Interactions with aromatic rings in chemical and biological recognition. Angew. Chem.-Int. Edit. 42, 1210-1250
38. Atkinson, S. E. (2002) Interaction of pyrethroids with the voltage-gated sodium channel. Ph.D. dissertation, University of Nottingham, U.K.
39. Elliott, M. (1980) Development of synthetic pyrethroids. In Pyrethroid Insecticides. Chemistry and Action, pp. 1-4, Table Ronde Rousell UCLAF
40. Mullaley, A. and Taylor, R. (1994) Conformational properties of pyrethroids. J. Comput. Aided Mol. Des. 8, 135-152
41. Jiang, Y. X., Lee, A., Chen, J. Y., Cadene, M., Chait, B. T. and MacKinnon, R. (2002) The open pore conformation of potassium channels. Nature (London) 417, 523-526
42. Chanda, B. and Bezanilla, F. (2002) Tracking voltage-dependent conformational changes in skeletal muscle sodium channel during activation. J. Gen. Physiol. 120, 629-645
43. Smith, M. R. and Goldin, A. L. (1997) Interaction between the sodium channel inactivation linker and domain III S4-S5. Biophys. J. 73, 1885-1895
44. Park, Y., Taylor, M. F. J. and Feyereisen, R. (1997) A valine 421 to methionine mutation in IS6 of the hscp voltage-gated sodium channel associated with pyrethroid resistance in Heliothis virescens F. Biochem. Biophys. Res. Commun. 239, 688-691
45. Vais, H., Williamson, M. S., Goodson, S. J., Devonshire, A. L., Warmke, J. W., Usherwood, P. N. R. and Cohen, C. J. (2000) Activation of Drosophila sodium channels promotes modification by deltamethrin - reductions in affinity caused by knock-down resistance mutations. J. Gen. Physiol. 115, 305-318
46. Zhou, Y. Y., Jiang, R., Ling, S. and Tseng, G. N. (1998) Stabilization of a channel's open state by a hydrophobic residue in the sixth membrane-spanning segment (S6) of rKv1.4. Pflugers Arch. Eur. J. Physiol. 437, 114-122
47. McDonald, I. K. and Thornton, J. M. (1994) Satisfying hydrogen-bonding potential in proteins. J. Mol. Biol. 238, 777-793