메뉴 건너뛰기




Volumn 3, Issue 2-3, 1997, Pages 261-268

Polycyclic dinitriles: A novel class of potent GABAergic insecticides provides a new radioligand, [3H]BIDN

Author keywords

BIDN; Convulsants; GABA receptors; Insecticides; Insects; Polycyclic dinitriles

Indexed keywords

3,3 BIS TRIFLUOROMETHYL BICYCLO[2,2,1]HEPTANE 2,2 DICARBONITRILE; 4 AMINOBUTYRIC ACID RECEPTOR BLOCKING AGENT; INSECTICIDE; POLYCYCLIC DINITRILE; RADIOLIGAND; UNCLASSIFIED DRUG;

EID: 17644431915     PISSN: 13542516     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02480383     Document Type: Conference Paper
Times cited : (10)

References (45)
  • 1
    • 0030901517 scopus 로고    scopus 로고
    • Sites of action of noncompetitive GABA antagonists in houseflies and rats: Three-dimensional QSAR analysis
    • Akamatsu, M., Ozoe, Y., Ueno, T., Fujita, T., Mochida, K., Nakamura, T. and Matsumura, F. (1997) Sites of action of noncompetitive GABA antagonists in houseflies and rats: Three-dimensional QSAR analysis. Pestic. Sci., 49, 319-332.
    • (1997) Pestic. Sci. , vol.49 , pp. 319-332
    • Akamatsu, M.1    Ozoe, Y.2    Ueno, T.3    Fujita, T.4    Mochida, K.5    Nakamura, T.6    Matsumura, F.7
  • 2
    • 0030474063 scopus 로고
    • Wild-type and insecticide resistant homo-oligomeric GABA receptors of Drosophila melanogaster stably expressed in a Drosophila cell line
    • Buckingham, S. D., Matsuda, K. A., Hosie, A. M., Baylis, H. A., Squire, M. D., Lansdell, S. J., Millar, N. S. and Sattelle, D. B. (1995) Wild-type and insecticide resistant homo-oligomeric GABA receptors of Drosophila melanogaster stably expressed in a Drosophila cell line. Neuropharmacol., 35, 1393-1401.
    • (1995) Neuropharmacol. , vol.35 , pp. 1393-1401
    • Buckingham, S.D.1    Matsuda, K.A.2    Hosie, A.M.3    Baylis, H.A.4    Squire, M.D.5    Lansdell, S.J.6    Millar, N.S.7    Sattelle, D.B.8
  • 3
    • 0027551098 scopus 로고
    • CoMFA validation of the superposition of 6 classes of compounds which block GABA receptors non-competitively
    • Calder, J. A. Wyatt, J. A., Frenkel, D. A. and Casida, J. E. (1993) CoMFA validation of the superposition of 6 classes of compounds which block GABA receptors non-competitively. J. Comput. Aided Molec. Design, 7, 45-60.
    • (1993) J. Comput. Aided Molec. Design , vol.7 , pp. 45-60
    • Calder, J.A.1    Wyatt, J.A.2    Frenkel, D.A.3    Casida, J.E.4
  • 4
    • 0022272063 scopus 로고
    • Structure-activity correlations for interactions of bicyclophosphorous esters and some polychlorocycloalkane and pyrethroid insecticides with the brain-specific t-butylbicyclophosphorothionate receptor
    • Casida, J. E. and Lawrence, L. J. (1985) Structure-activity correlations for interactions of bicyclophosphorous esters and some polychlorocycloalkane and pyrethroid insecticides with the brain-specific t-butylbicyclophosphorothionate receptor. Environ. Health Perspect., 61, 123-132.
    • (1985) Environ. Health Perspect. , vol.61 , pp. 123-132
    • Casida, J.E.1    Lawrence, L.J.2
  • 5
    • 0021966858 scopus 로고
    • Bicycloorthocarboxylate convulsants: Potent GABA receptor antagonists
    • Casida, J. E., Palmer, C. J. and Cole, L. M. (1985) Bicycloorthocarboxylate convulsants: potent GABA receptor antagonists. Mol. Pharmacol., 28, 246-253.
    • (1985) Mol. Pharmacol. , vol.28 , pp. 246-253
    • Casida, J.E.1    Palmer, C.J.2    Cole, L.M.3
  • 6
    • 0027344016 scopus 로고
    • Insecticide action at the GABA-gated chloride channel: Recognition, progress, and prospects
    • Casida, J. E. (1993) Insecticide action at the GABA-gated chloride channel: Recognition, progress, and prospects. Arch. Insect Biochem. Physiol., 22, 13-23.
    • (1993) Arch. Insect Biochem. Physiol. , vol.22 , pp. 13-23
    • Casida, J.E.1
  • 8
    • 0028816129 scopus 로고
    • 3H]EBOB binding site associated with Ala→Ser or Gly mutants of Rdl subunit
    • 3H]EBOB binding site associated with Ala→Ser or Gly mutants of Rdl subunit. Life Sci., 56, 757-767.
    • (1995) Life Sci. , vol.56 , pp. 757-767
    • Cole, L.M.1    Roush, R.T.2    Casida, J.E.3
  • 10
    • 0003137308 scopus 로고
    • House fly brain γ-aminobutyric acid-gated chloride channel: Target for multiple classes of insecticide
    • Deng, Y., Palmer, C. J. and Casida, J. E. (1991) House fly brain γ-aminobutyric acid-gated chloride channel: target for multiple classes of insecticide. Pestic. Biochem. Physiol., 41, 60-65.
    • (1991) Pestic. Biochem. Physiol. , vol.41 , pp. 60-65
    • Deng, Y.1    Palmer, C.J.2    Casida, J.E.3
  • 11
    • 0027280680 scopus 로고
    • A point mutation in a Drosophila GABA receptor confers insecticide resistance
    • Ffrench-Constant, R. H., Rocheleau, T. A., Steichen, J. C. and Chalmers, A. E. (1993a) A point mutation in a Drosophila GABA receptor confers insecticide resistance. Nature, 363, 449-451.
    • (1993) Nature , vol.363 , pp. 449-451
    • Ffrench-Constant, R.H.1    Rocheleau, T.A.2    Steichen, J.C.3    Chalmers, A.E.4
  • 12
    • 0009062235 scopus 로고
    • Cyclodiene insecticide resistance in Drosophila melanogaster (Meigen) is associated with a temperature sensitive phenotype. Pestic
    • Ffrench-Constant, R. H., Steichen, J. and Ode, P. (1993b) Cyclodiene insecticide resistance in Drosophila melanogaster (Meigen) is associated with a temperature sensitive phenotype. Pestic. Biochem. Physiol., 46, 73-77.
    • (1993) Biochem. Physiol. , vol.46 , pp. 73-77
    • Ffrench-Constant, R.H.1    Steichen, J.2    Ode, P.3
  • 14
    • 0029082012 scopus 로고
    • Actions of the insecticide fipronil on dieldrin-sensitive and -resistant GABA receptors of Drosophila melanogaster
    • Hosie, A. M., Baylis, H. A., Buckingham, S. D. and Sattelle, D. B. (1995a) Actions of the insecticide fipronil on dieldrin-sensitive and -resistant GABA receptors of Drosophila melanogaster. Br. J. Pharmacol., 115, 909-912.
    • (1995) Br. J. Pharmacol. , vol.115 , pp. 909-912
    • Hosie, A.M.1    Baylis, H.A.2    Buckingham, S.D.3    Sattelle, D.B.4
  • 15
    • 0029121446 scopus 로고
    • Blocking actions of BIDN, a bicyclic dinitrile convulsant compound, on wild-type and dieldrin-resistant GABA receptor homo-oligomers of Drosophila melanogaster expressed in Xenopus oocytes
    • Hosie, A. M., Shirai, Y., Buckingham, S. D., Rauh, J. J., Roush, R. T., Baylis, H. A. and Sattelle, D. B. (1995b) Blocking actions of BIDN, a bicyclic dinitrile convulsant compound, on wild-type and dieldrin-resistant GABA receptor homo-oligomers of Drosophila melanogaster expressed in Xenopus oocytes. Brain Res., 693, 257-260.
    • (1995) Brain Res. , vol.693 , pp. 257-260
    • Hosie, A.M.1    Shirai, Y.2    Buckingham, S.D.3    Rauh, J.J.4    Roush, R.T.5    Baylis, H.A.6    Sattelle, D.B.7
  • 16
    • 0014311141 scopus 로고
    • Structural aspects of picrotoxinin action
    • Jarboe C. H., Porter, L. A. and Buckler, R. T. (1968) Structural aspects of picrotoxinin action. J. Med. Chem., 11, 729-731.
    • (1968) J. Med. Chem. , vol.11 , pp. 729-731
    • Jarboe, C.H.1    Porter, L.A.2    Buckler, R.T.3
  • 17
    • 0020641534 scopus 로고
    • Computer-assisted modeling of the picrotoxinin and γ-butyrolactone receptor site
    • Klunk, W. E., Kalman, B. L., Ferrendelli, J. A. and Covey, D. F. (1983) Computer-assisted modeling of the picrotoxinin and γ-butyrolactone receptor site. Mol. Pharmacol., 23, 511-518.
    • (1983) Mol. Pharmacol. , vol.23 , pp. 511-518
    • Klunk, W.E.1    Kalman, B.L.2    Ferrendelli, J.A.3    Covey, D.F.4
  • 18
    • 0021247486 scopus 로고
    • Interactions of lindane, toxaphene and cyclodienes with brain specific t-butylbicyclophosphorothionate receptor
    • Lawrence, L. J. and Casida, J. E. (1984) Interactions of lindane, toxaphene and cyclodienes with brain specific t-butylbicyclophosphorothionate receptor. Life Sci., 35, 171-178.
    • (1984) Life Sci. , vol.35 , pp. 171-178
    • Lawrence, L.J.1    Casida, J.E.2
  • 19
    • 0027363790 scopus 로고
    • Expression of a Drosophila GABA receptor in a baculovirus-insect cell system - Functional expression of insecticide susceptible and resistant GABA receptors from the cyclodiene resistant gene Rdl
    • Lee, H. J., Rocheleau, T., Zhang, H. G., Jackson, M. B. and Ffrench-Constant, R. H. (1993) Expression of a Drosophila GABA receptor in a baculovirus-insect cell system - functional expression of insecticide susceptible and resistant GABA receptors from the cyclodiene resistant gene Rdl. FEBS Letts., 335, 315-318.
    • (1993) FEBS Letts. , vol.335 , pp. 315-318
    • Lee, H.J.1    Rocheleau, T.2    Zhang, H.G.3    Jackson, M.B.4    Ffrench-Constant, R.H.5
  • 20
    • 0030135608 scopus 로고    scopus 로고
    • Interaction of lindane isomers with chloride currents in insect membranes: Steric requirements for channel modulation and block
    • Lees, G. and Calder, J. (1996) Interaction of lindane isomers with chloride currents in insect membranes: Steric requirements for channel modulation and block. Pestic. Biochem. Physiol., 55, 40-48.
    • (1996) Pestic. Biochem. Physiol. , vol.55 , pp. 40-48
    • Lees, G.1    Calder, J.2
  • 22
    • 0020697489 scopus 로고
    • Evidence for similarities between cyclodiene type insecticides and picrotoxinin in their action mechanisms
    • Matsumura, F. and Ghiasuddin, S. M. (1983) Evidence for similarities between cyclodiene type insecticides and picrotoxinin in their action mechanisms. J. Environ. Sci. Health, B18, 1-14.
    • (1983) J. Environ. Sci. Health , vol.B18 , pp. 1-14
    • Matsumura, F.1    Ghiasuddin, S.M.2
  • 23
    • 7144248819 scopus 로고
    • GABA-related systems as targets for insecticides
    • Sites of Action of Neurotoxic Pesticides, ed. R. M. Hollingworth and M. B. Green, Washington, DC: American Chemical Society
    • Matsumura, F., Tanaka, K. and Ozoe, Y. (1987) GABA-related systems as targets for insecticides. In: Sites of Action of Neurotoxic Pesticides, ACS Symposium Series 356, ed. R. M. Hollingworth and M. B. Green, p 52. Washington, DC: American Chemical Society.
    • (1987) ACS Symposium Series 356 , pp. 52
    • Matsumura, F.1    Tanaka, K.2    Ozoe, Y.3
  • 24
    • 0000181498 scopus 로고
    • 1,1-Dicyano-2,2-bis(trifluoromethyl)ethylene
    • Middleton, W. J. (1965) 1,1-Dicyano-2,2-bis(trifluoromethyl)ethylene. J. Org. Chem., 30, 1402-1407.
    • (1965) J. Org. Chem. , vol.30 , pp. 1402-1407
    • Middleton, W.J.1
  • 25
    • 0000548088 scopus 로고
    • Fluorine-containing 1,1-dicyanoethylenes: Their preparation, Diels-Alder reactions and derived norbornenes and norbornanes
    • Middleton, W. J. and Bingham, E. M. (1982) Fluorine-containing 1,1-dicyanoethylenes: their preparation, Diels-Alder reactions and derived norbornenes and norbornanes. J. Fluorine Chem., 20, 397-418.
    • (1982) J. Fluorine Chem. , vol.20 , pp. 397-418
    • Middleton, W.J.1    Bingham, E.M.2
  • 26
  • 28
    • 33751499991 scopus 로고
    • Feeding and toxic effects of floral sesquiterpene lactones, diterpenes and phenolics from sunflower on western corn rootworm
    • Mullin, C. A., Alfatafta, A. A., Harman, J. L., Everett, S. L. and Serino, A. A. (1991) Feeding and toxic effects of floral sesquiterpene lactones, diterpenes and phenolics from sunflower on western corn rootworm. J. Agric. Food Chem., 39, 2293.
    • (1991) J. Agric. Food Chem. , vol.39 , pp. 2293
    • Mullin, C.A.1    Alfatafta, A.A.2    Harman, J.L.3    Everett, S.L.4    Serino, A.A.5
  • 30
    • 0000947873 scopus 로고
    • Structural requirements for bridged bicyclic compounds acting on the picrotoxinin receptor
    • Ozoe, Y. and Matsumura, F. (1986) Structural requirements for bridged bicyclic compounds acting on the picrotoxinin receptor. J. Agric. Food Chem., 34, 126-134.
    • (1986) J. Agric. Food Chem. , vol.34 , pp. 126-134
    • Ozoe, Y.1    Matsumura, F.2
  • 31
    • 0001448711 scopus 로고
    • Structure-activity relationships in a new series of insecticidally active dioxatricycloalkenes derived by structural comparison of the GABA antagonists bicycloorthocarboxylates and endosulfan
    • Ozoe, Y., Sawada, Y., Mochida, K., Nakamura, T. and Matsumura, F. (1990) Structure-activity relationships in a new series of insecticidally active dioxatricycloalkenes derived by structural comparison of the GABA antagonists bicycloorthocarboxylates and endosulfan. J. Agric. Food Chem., 38, 1264-1268.
    • (1990) J. Agric. Food Chem. , vol.38 , pp. 1264-1268
    • Ozoe, Y.1    Sawada, Y.2    Mochida, K.3    Nakamura, T.4    Matsumura, F.5
  • 32
    • 0025690774 scopus 로고
    • Bioactivity is the function of structure. 16. in vitro models of bicyclic insecticides
    • Paramonov, A. L., Potashnikov, P. F. and Sokol'skii, G. A. (1990) Bioactivity is the function of structure. 16. In vitro models of bicyclic insecticides. Khim. Farm. Zh., 24, 43-46.
    • (1990) Khim. Farm. Zh. , vol.24 , pp. 43-46
    • Paramonov, A.L.1    Potashnikov, P.F.2    Sokol'Skii, G.A.3
  • 34
    • 0025316332 scopus 로고
    • Pharmacological and biochemical properties of insect GABA receptors
    • Rauh, J. J., Lummis, S. C. R. and Sattelle, D. B. (1990) Pharmacological and biochemical properties of insect GABA receptors. Trends Pharmacol. Sci., 11, 325-329.
    • (1990) Trends Pharmacol. Sci. , vol.11 , pp. 325-329
    • Rauh, J.J.1    Lummis, S.C.R.2    Sattelle, D.B.3
  • 35
    • 0027466773 scopus 로고
    • Steroids reveal differences between GABA-operated chloride channels of insects and vertebrates
    • Rauh, J. J., Vassallo, J. G., Lummis, S. C. R., Wafford, K. A. and Sattelle, D. B. (1993) Steroids reveal differences between GABA-operated chloride channels of insects and vertebrates. Mol. Neuropharmacol., 3, 1-9.
    • (1993) Mol. Neuropharmacol. , vol.3 , pp. 1-9
    • Rauh, J.J.1    Vassallo, J.G.2    Lummis, S.C.R.3    Wafford, K.A.4    Sattelle, D.B.5
  • 36
    • 0002248977 scopus 로고
    • GABA receptors of insects
    • Sattelle, D. B. (1990) GABA receptors of insects. Adv. Insect Physiol., 22, 1-113.
    • (1990) Adv. Insect Physiol. , vol.22 , pp. 1-113
    • Sattelle, D.B.1
  • 38
    • 0000152667 scopus 로고
    • Cycloaddition reactions of 'quadricyclanes'
    • Smith, C. D. (1966) Cycloaddition reactions of 'quadricyclanes'. J. Am. Chem. Soc., 88, 4273-4274.
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 4273-4274
    • Smith, C.D.1
  • 39
    • 0002751083 scopus 로고
    • Correlation between biological activity and molecular structure of cyclodiene insecticides
    • Soloway, S. B. (1965) Correlation between biological activity and molecular structure of cyclodiene insecticides. Adv. Pest Control Res., 6, 85-126.
    • (1965) Adv. Pest Control Res. , vol.6 , pp. 85-126
    • Soloway, S.B.1
  • 40
    • 33947088328 scopus 로고
    • Regio- and stereospecific [2π +, 2σ + 2σ] cycloaddition reaction of quadricyclane
    • Tabushi, I., Yamamura, K. and Yoshida, Z.-I. (1972) Regio- and stereospecific [2π +, 2σ + 2σ] cycloaddition reaction of quadricyclane. J. Am. Chem. Soc., 94, 787-792.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 787-792
    • Tabushi, I.1    Yamamura, K.2    Yoshida, Z.-I.3
  • 41
    • 0021073994 scopus 로고
    • Convulsant/depressant site of action at the allosteric benzodiazepine-GABA receptor complex
    • Ticku, M. R. and Maksay, G. (1983) Convulsant/depressant site of action at the allosteric benzodiazepine-GABA receptor complex. Life Sci., 33, 2363.
    • (1983) Life Sci. , vol.33 , pp. 2363
    • Ticku, M.R.1    Maksay, G.2
  • 42
    • 0024323580 scopus 로고
    • Block of an insect Central nervous-system GABA receptor by cyclodiene and cyclohexane insecticides
    • Wafford, K. A., Lummis, S. C. R. and Sattelle, D. B. (1989) Block of an insect Central nervous-system GABA receptor by cyclodiene and cyclohexane insecticides. Proc. R. Soc. B., 237, 53-61.
    • (1989) Proc. R. Soc. B. , vol.237 , pp. 53-61
    • Wafford, K.A.1    Lummis, S.C.R.2    Sattelle, D.B.3
  • 43
    • 0025082544 scopus 로고
    • Two insecticidal monoterpenes, telfairine and aplysiaterpenoid A, from the red alga Plocamium telfairiae: Structure elucidation, biological activity and molecular topographical consideration by a semiempirical molecular orbital study
    • Watanabe, K., Umeda, K., Kurita, Y., Takayama, C. and Miyakado, M. (1990) Two insecticidal monoterpenes, telfairine and aplysiaterpenoid A, from the red alga Plocamium telfairiae: Structure elucidation, biological activity and molecular topographical consideration by a semiempirical molecular orbital study. Pestic. Biochem. Physiol., 37, 275-286.
    • (1990) Pestic. Biochem. Physiol. , vol.37 , pp. 275-286
    • Watanabe, K.1    Umeda, K.2    Kurita, Y.3    Takayama, C.4    Miyakado, M.5
  • 44
    • 0024435345 scopus 로고
    • Conformational requirements for convulsant compounds
    • Wong, M. G., and Andrews, P. R. (1989) Conformational requirements for convulsant compounds. Eur. J. Med. Chem., 24, 323-334.
    • (1989) Eur. J. Med. Chem. , vol.24 , pp. 323-334
    • Wong, M.G.1    Andrews, P.R.2
  • 45
    • 0027956644 scopus 로고
    • A unique amino acid of the Drosophila GABA receptor with influence on drug sensitivity by two mechanisms
    • Zhang, H-G., Ffrench-Constant, R. H. and Jackson, M. B. (1994) A unique amino acid of the Drosophila GABA receptor with influence on drug sensitivity by two mechanisms. J. Physiol. (Lond.), 479, 65-75.
    • (1994) J. Physiol. (Lond.) , vol.479 , pp. 65-75
    • Zhang, H.-G.1    Ffrench-Constant, R.H.2    Jackson, M.B.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.