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Volumn 42, Issue 25, 2003, Pages 7819-7827

The neonicotinoid electronegative pharmacophore plays the crucial role in the high affinity and selectivity for the Drosophila nicotinic receptor: An anomaly for the nicotinoid cation-π interaction model

Author keywords

[No Author keywords available]

Indexed keywords

POSITIVE IONS; QUANTUM THEORY; TOPOLOGY; X RAY CRYSTALLOGRAPHY;

EID: 0038338722     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi0300130     Document Type: Article
Times cited : (128)

References (47)
  • 1
    • 0000679333 scopus 로고    scopus 로고
    • Insect nicotinic acetylcholine receptors: Genes, structure, physiological and pharmacological properties
    • Clementi, F., Fornasari, D., and Gotti, C., Eds., Springer-Verlag, Berlin
    • Gundelfinger, E. D., and Schultz, R. (2000) Insect nicotinic acetylcholine receptors: genes, structure, physiological and pharmacological properties in Handbook of Experimental Pharmacology, Volume 144: Neuronal Nicotinic Receptors (Clementi, F., Fornasari, D., and Gotti, C., Eds.) pp 497-521, Springer-Verlag, Berlin.
    • (2000) Handbook of Experimental Pharmacology Volume 144, Neuronal Nicotinic Receptors , vol.144 , pp. 497-521
    • Gundelfinger, E.D.1    Schultz, R.2
  • 2
    • 0033694834 scopus 로고    scopus 로고
    • Ion channels and synaptic organization: Analysis of the Drosophila genome
    • Littleton, J. T., and Ganetzky, B. (2000) Ion channels and synaptic organization: analysis of the Drosophila genome, Neuron 26, 35-43.
    • (2000) Neuron , vol.26 , pp. 35-43
    • Littleton, J.T.1    Ganetzky, B.2
  • 3
    • 0034765784 scopus 로고    scopus 로고
    • Structure and diversity of insect nicotinic acetylcholine receptors
    • Tomizawa, M., and Casida, J. E. (2001) Structure and diversity of insect nicotinic acetylcholine receptors, Pest Manag. Sci. 57, 914-922.
    • (2001) Pest Manag. Sci. , vol.57 , pp. 914-922
    • Tomizawa, M.1    Casida, J.E.2
  • 4
    • 0037209233 scopus 로고    scopus 로고
    • Selective toxicity of neonicotinoids attributable to specificity of insect and mammalian nicotinic receptors
    • Tomizawa, M., and Casida, J. E. (2003) Selective toxicity of neonicotinoids attributable to specificity of insect and mammalian nicotinic receptors, Annu. Rev. Entomol. 48, 339-364.
    • (2003) Annu. Rev. Entomol. , vol.48 , pp. 339-364
    • Tomizawa, M.1    Casida, J.E.2
  • 5
    • 0036275679 scopus 로고    scopus 로고
    • Nicotinic acetylcholine receptors of Drosophila: Three subunits encoded by genomically linked genes can co-assemble into the same receptor complex
    • Chamaon, K., Smalla, K.-H., Thomas, U., and Gundelfinger, E. D. (2002) Nicotinic acetylcholine receptors of Drosophila: three subunits encoded by genomically linked genes can co-assemble into the same receptor complex, J. Neurochem. 80, 149-157.
    • (2002) J. Neurochem. , vol.80 , pp. 149-157
    • Chamaon, K.1    Smalla, K.-H.2    Thomas, U.3    Gundelfinger, E.D.4
  • 6
    • 0036021457 scopus 로고    scopus 로고
    • Dβ3, an atypical nicotinic acetylcholine receptor subunit from Drosophila: Molecular cloning, heterologous expression and coassembly
    • Lansdell, S. J., and Millar, N. S. (2002) Dβ3, an atypical nicotinic acetylcholine receptor subunit from Drosophila: molecular cloning, heterologous expression and coassembly, J. Neurochem. 80, 1009-1018.
    • (2002) J. Neurochem. , vol.80 , pp. 1009-1018
    • Lansdell, S.J.1    Millar, N.S.2
  • 7
    • 0029789274 scopus 로고    scopus 로고
    • Novel neonicotinoid-agarose affinity column for Drosophila and Musca nicotinic acetylcholine receptors
    • Tomizawa, M., Latli, B., and Casida, J. E. (1996) Novel neonicotinoid-agarose affinity column for Drosophila and Musca nicotinic acetylcholine receptors, J. Neurochem. 67, 1669-1676.
    • (1996) J. Neurochem. , vol.67 , pp. 1669-1676
    • Tomizawa, M.1    Latli, B.2    Casida, J.E.3
  • 8
    • 0034110016 scopus 로고    scopus 로고
    • Neuronal nicotinic acetylcholine receptors from Drosophila: Two different types of α subunits coassemble within the same receptor complex
    • Schulz, R., Bertrand, S., Chamaon, K., Smalla, K.-H., Gundelfinger, E. D., and Bertrand, D. (2000) Neuronal nicotinic acetylcholine receptors from Drosophila: two different types of α subunits coassemble within the same receptor complex, J. Neurochem. 74, 2537-2546.
    • (2000) J. Neurochem. , vol.74 , pp. 2537-2546
    • Schulz, R.1    Bertrand, S.2    Chamaon, K.3    Smalla, K.-H.4    Gundelfinger, E.D.5    Bertrand, D.6
  • 9
    • 0031283072 scopus 로고    scopus 로고
    • 125]Azidonicotinoid photoaffinity labeling of insecticide-binding subunit of Drosophila nicotinic acetylcholine receptor
    • 125]Azidonicotinoid photoaffinity labeling of insecticide-binding subunit of Drosophila nicotinic acetylcholine receptor, Neurosci. Lett. 237, 61-64.
    • (1997) Neurosci. Lett. , vol.237 , pp. 61-64
    • Tomizawa, M.1    Casida, J.E.2
  • 11
    • 0030043489 scopus 로고    scopus 로고
    • Cation-π interactions in chemistry and biology: A new view of benzene, Phe, Tyr, and Trp
    • Dougherty, D. A. (1996) Cation-π interactions in chemistry and biology: a new view of benzene, Phe, Tyr, and Trp, Science 271, 163-168.
    • (1996) Science , vol.271 , pp. 163-168
    • Dougherty, D.A.1
  • 12
    • 0032514762 scopus 로고    scopus 로고
    • From ab initio quantum mechanics to molecular neurobiology: A cation-π binding site in the nicotinic receptor
    • Zhong, W., Gallivan, J. P., Zhang, Y., Li, L., Lester, H. A., and Dougherty, D. A. (1998) From ab initio quantum mechanics to molecular neurobiology: a cation-π binding site in the nicotinic receptor, Proc. Natl. Acad. Sci. U.S.A. 95, 12088-12093.
    • (1998) Proc. Natl. Acad. Sci. U.S.A. , vol.95 , pp. 12088-12093
    • Zhong, W.1    Gallivan, J.P.2    Zhang, Y.3    Li, L.4    Lester, H.A.5    Dougherty, D.A.6
  • 13
    • 0032904374 scopus 로고    scopus 로고
    • Minor structural changes in nicotinoid insecticides confer differential subtype selectivity for mammalian nicotinic acetylcholine receptors
    • Tomizawa, M., and Casida, J. E. (1999) Minor structural changes in nicotinoid insecticides confer differential subtype selectivity for mammalian nicotinic acetylcholine receptors, Br. J. Pharmacol. 127, 115-122.
    • (1999) Br. J. Pharmacol. , vol.127 , pp. 115-122
    • Tomizawa, M.1    Casida, J.E.2
  • 14
    • 0034569643 scopus 로고    scopus 로고
    • Neonicotinoid insecticides: Molecular features conferring selectivity for insect versus mammalian nicotinic receptors
    • Tomizawa, M., Lee, D. L., and Casida, J. E. (2000) Neonicotinoid insecticides: molecular features conferring selectivity for insect versus mammalian nicotinic receptors, J. Agric. Food Chem. 48, 6016-6024.
    • (2000) J. Agric. Food Chem. , vol.48 , pp. 6016-6024
    • Tomizawa, M.1    Lee, D.L.2    Casida, J.E.3
  • 15
    • 0035891562 scopus 로고    scopus 로고
    • Analgesic and toxic effects of neonicotinoid insecticides in mice
    • Tomizawa, M., Cowan, A., and Casida, J. E. (2001) Analgesic and toxic effects of neonicotinoid insecticides in mice, Toxicol. Appl. Pharmacol. 177, 77-83.
    • (2001) Toxicol. Appl. Pharmacol. , vol.177 , pp. 77-83
    • Tomizawa, M.1    Cowan, A.2    Casida, J.E.3
  • 16
    • 0037142378 scopus 로고    scopus 로고
    • Structural features of azidopyridinyl neonicotinoid probes conferring high affinity and selectivity for mammalian α4β2 and Drosophila nicotinic receptors
    • Zhang, N., Tomizawa, M., and Casida, J. E. (2002) Structural features of azidopyridinyl neonicotinoid probes conferring high affinity and selectivity for mammalian α4β2 and Drosophila nicotinic receptors, J. Med. Chem. 45, 2832-2840.
    • (2002) J. Med. Chem. , vol.45 , pp. 2832-2840
    • Zhang, N.1    Tomizawa, M.2    Casida, J.E.3
  • 18
    • 0032833362 scopus 로고    scopus 로고
    • Synthesis of iodoaminoimidazole arabinoside (IAIA): A potential reductive metabolite of the spect imaging agent, iodoazomycin arabinoside (IAZA)
    • Lee, H. C., Kumar, P., Wiebe, L. I., McDonald, R., Mercer, J. R., Ohkura, K., and Seki, K.-i. (1999) Synthesis of iodoaminoimidazole arabinoside (IAIA): a potential reductive metabolite of the spect imaging agent, iodoazomycin arabinoside (IAZA), Nucleosides Nucleotides 18, 1995-2016.
    • (1999) Nucleosides Nucleotides , vol.18 , pp. 1995-2016
    • Lee, H.C.1    Kumar, P.2    Wiebe, L.I.3    McDonald, R.4    Mercer, J.R.5    Ohkura, K.6    Seki, K.I.7
  • 19
    • 0037867320 scopus 로고    scopus 로고
    • (1993) Preparation of nitroguanidines as agrochemicals, Jpn. Kokai Tokkyo Koho JP 05112521
    • Isao, A., and Isao, M. (1993) Preparation of nitroguanidines as agrochemicals, Jpn. Kokai Tokkyo Koho JP 05112521.
    • Isao, A.1    Isao, M.2
  • 21
    • 0033577991 scopus 로고    scopus 로고
    • Novel and potent 6-chloro-3-pyridinyl ligands for the α4β2 neuronal acetylcholine receptor
    • Latli, B., D'Amour, K., and Casida, J. E. (1999) Novel and potent 6-chloro-3-pyridinyl ligands for the α4β2 neuronal acetylcholine receptor, J. Med. Chem. 42, 2227-2234.
    • (1999) J. Med. Chem. , vol.42 , pp. 2227-2234
    • Latli, B.1    D'Amour, K.2    Casida, J.E.3
  • 22
    • 4243553426 scopus 로고
    • Density-functional exchange-energy approximation with correct asymptotic-behavior
    • Becke, A. D. (1988) Density-functional exchange-energy approximation with correct asymptotic-behavior, Phys. Rev. A 38, 3098-3100.
    • (1988) Phys. Rev. A , vol.38 , pp. 3098-3100
    • Becke, A.D.1
  • 23
    • 0345491105 scopus 로고
    • Development of the Colle-Salvetti correlation-energy formula into a functional of the electron-density
    • Lee, C. T., Yang, W. T., and Parr, R. G. (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron-density, Phys. Rev. B 37, 785-789.
    • (1988) Phys. Rev. B , vol.37 , pp. 785-789
    • Lee, C.T.1    Yang, W.T.2    Parr, R.G.3
  • 24
    • 0038596731 scopus 로고
    • Results obtained with the correlation-energy density functionals of Becke and Lee, Yang and Parr
    • Miehlich, B., Savin, A., Stoll, H., and Preuss, H. (1989) Results obtained with the correlation-energy density functionals of Becke and Lee, Yang and Parr, Chem. Phys. Lett. 157, 200-206.
    • (1989) Chem. Phys. Lett. , vol.157 , pp. 200-206
    • Miehlich, B.1    Savin, A.2    Stoll, H.3    Preuss, H.4
  • 25
    • 0033975523 scopus 로고    scopus 로고
    • A computational study of nicotine conformations in the gas phase and in water
    • Elmore, D. E., and Dougherty, D. A. (2000) A computational study of nicotine conformations in the gas phase and in water, J. Org. Chem. 65, 742-747.
    • (2000) J. Org. Chem. , vol.65 , pp. 742-747
    • Elmore, D.E.1    Dougherty, D.A.2
  • 26
    • 0000304948 scopus 로고
    • Accurate first principles calculation of molecular charge-distributions and solvation energies from ab initio quantum-mechanics and continuum dielectric theory
    • Tannor, D. J., Marten, B., Murphy, R., Friesner, R. A., Sitkoff, D., Nicholls, A., Ringnalda, M., Goddard, W. A., and Honig, B. (1994) Accurate first principles calculation of molecular charge-distributions and solvation energies from ab initio quantum-mechanics and continuum dielectric theory, J. Am. Chem. Soc. 116, 11875-11882.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 11875-11882
    • Tannor, D.J.1    Marten, B.2    Murphy, R.3    Friesner, R.A.4    Sitkoff, D.5    Nicholls, A.6    Ringnalda, M.7    Goddard, W.A.8    Honig, B.9
  • 27
    • 0030180875 scopus 로고    scopus 로고
    • New model for calculation of solvation free energies: Correction of self-consistent reaction field continuum dielectric theory for shortrange hydrogen-bonding effects
    • Marten, B., Kim, K., Cortis, C., Friesner, R. A., Murphy, R. B., Ringnalda, M. N., Sitkoff, D., and Honig, B. (1996) New model for calculation of solvation free energies: correction of self-consistent reaction field continuum dielectric theory for shortrange hydrogen-bonding effects, J. Phys. Chem. 100, 11775-11788.
    • (1996) J. Phys. Chem. , vol.100 , pp. 11775-11788
    • Marten, B.1    Kim, K.2    Cortis, C.3    Friesner, R.A.4    Murphy, R.B.5    Ringnalda, M.N.6    Sitkoff, D.7    Honig, B.8
  • 28
    • 0026590397 scopus 로고
    • A graphics program for the analysis and display of molecular dynamics trajectories
    • Laaksonen, L. (1992) A graphics program for the analysis and display of molecular dynamics trajectories, J. Mol. Graphics 10, 33-34.
    • (1992) J. Mol. Graphics , vol.10 , pp. 33-34
    • Laaksonen, L.1
  • 29
    • 0034669057 scopus 로고    scopus 로고
    • Imidacloprid, thiacloprid, and their imine derivatives up-regulate the α4β2 nicotinic acetylcholine receptor in M10 cells
    • Tomizawa, M., and Casida, J. E. (2000) Imidacloprid, thiacloprid, and their imine derivatives up-regulate the α4β2 nicotinic acetylcholine receptor in M10 cells, Toxicol. Appl. Pharmacol. 169, 114-120.
    • (2000) Toxicol. Appl. Pharmacol. , vol.169 , pp. 114-120
    • Tomizawa, M.1    Casida, J.E.2
  • 30
    • 0001270581 scopus 로고
    • 3H]imidacloprid binding site in house fly head acetylcholine receptor to insecticidal activity of 2-nitromethylene- and 2-nitroimino-imidazolidines
    • 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.
    • (1993) Pestic. Biochem. Physiol. , vol.46 , pp. 200-206
    • Liu, M.-Y.1    Lanford, J.2    Casida, J.E.3
  • 32
    • 0000602517 scopus 로고    scopus 로고
    • Chloronicotinyl insecticides. 8. Crystal and molecular structures of imidacloprid and analogous compounds
    • Kagabu, S., and Matsuno, H. (1997) Chloronicotinyl insecticides. 8. Crystal and molecular structures of imidacloprid and analogous compounds, J. Agric. Food Chem. 45, 276-281.
    • (1997) J. Agric. Food Chem. , vol.45 , pp. 276-281
    • Kagabu, S.1    Matsuno, H.2
  • 33
    • 0030614376 scopus 로고    scopus 로고
    • 125I]neonicotinoid photoaffinity probe for the Drosophila nicotinic acetylcholine receptor
    • 125I]neonicotinoid photoaffinity probe for the Drosophila nicotinic acetylcholine receptor, Bioconjugate Chem. 8, 7-14.
    • (1997) Bioconjugate Chem. , vol.8 , pp. 7-14
    • Latli, B.1    Tomizawa, M.2    Casida, J.E.3
  • 34
    • 0000992611 scopus 로고
    • Stability comparison of imidacloprid and related compounds under simulated sunlight, hydrolysis conditions, and to oxygen
    • Kagabu, S., and Medej, S. (1995) Stability comparison of imidacloprid and related compounds under simulated sunlight, hydrolysis conditions, and to oxygen, Biosci., Biotechnol., Biochem. 59, 980-985.
    • (1995) Biosci., Biotechnol., Biochem. , vol.59 , pp. 980-985
    • Kagabu, S.1    Medej, S.2
  • 36
    • 85008520360 scopus 로고
    • Structure-activity relationships of nicotinoids and imidacloprid analogs
    • Tomizawa, M., and Yamamoto, I. (1993) Structure-activity relationships of nicotinoids and imidacloprid analogs, J. Pestic. Sci. 18, 91-98.
    • (1993) J. Pestic. Sci. , vol.18 , pp. 91-98
    • Tomizawa, M.1    Yamamoto, I.2
  • 38
    • 0031741696 scopus 로고    scopus 로고
    • Prediction of the binding mode of imidacloprid and related compounds to house-fly head acetylcholine receptors using three-dimensional QSAR analysis
    • Okazawa, A., Akamatsu, M., Ohoka, A., Nishiwaki, H., Cho, W.-J., Nakagawa, Y., Nishimura, K., and Ueno, T. (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, 134-144.
    • (1998) Pestic. Sci. , vol.54 , pp. 134-144
    • Okazawa, A.1    Akamatsu, M.2    Ohoka, A.3    Nishiwaki, H.4    Cho, W.-J.5    Nakagawa, Y.6    Nishimura, K.7    Ueno, T.8
  • 39
    • 0031911045 scopus 로고    scopus 로고
    • Quantitative correlation between molecular similarity and receptor-binding activity of neonicotinoid insecticides
    • Nakayama, A., and Sukekawa, M. (1998) Quantitative correlation between molecular similarity and receptor-binding activity of neonicotinoid insecticides, Pestic. Sci. 52, 104-110.
    • (1998) Pestic. Sci. , vol.52 , pp. 104-110
    • Nakayama, A.1    Sukekawa, M.2
  • 44
    • 0026452097 scopus 로고
    • Nicotinic acetylcholine receptors of the central nervous system of Drosophila
    • Gundelfinger, E. D., and Hess, N. (1992) Nicotinic acetylcholine receptors of the central nervous system of Drosophila, Biochim. Biophys. Acta 1137, 299-308.
    • (1992) Biochim. Biophys. Acta , vol.1137 , pp. 299-308
    • Gundelfinger, E.D.1    Hess, N.2
  • 47
    • 0035902009 scopus 로고    scopus 로고
    • Crystal structure of an ACh-binding protein reveals the ligand-binding domain of nicotinic receptors
    • Brejc, K., van Dijk, W. J., Klaassen, R. V., Schuurmans, M., van der Oost, J., Smit, A. B., and Sixma, T. K. (2001) Crystal structure of an ACh-binding protein reveals the ligand-binding domain of nicotinic receptors, Nature 411, 269-276.
    • (2001) Nature , vol.411 , pp. 269-276
    • Brejc, K.1    Van Dijk, W.J.2    Klaassen, R.V.3    Schuurmans, M.4    Van der Oost, J.5    Smit, A.B.6    Sixma, T.K.7


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