Synthesis and structure-activity relationship analysis of bicyclophosphorothionate blockers with selectivity for housefly γ-aminobutyric acid receptor channels

Pest Management Science

Volumn 66, Issue 9, 2010, Pages 1002-1010

  Ju, Xiu Lian ^a   Fusazaki, Sayaka ^b   Hishinuma, Hiroyuki ^b   Qiao, Xiaomu ^b   Ikeda, Izumi ^b   Ozoe, Yoshihisa ^b  

^a WUHAN INSTITUTE OF TECHNOLOGY   (China)

^b SHIMANE UNIVERSITY   (Japan)

Author keywords

aminobutyric acid receptors; Bicyclophosphorothionates; Blockers; Selectivity

Indexed keywords

1 (4 ETHYNYLPHENYL) 4 PROPYL 2,6,7 TRIOXABICYCLO(2.2.2)OCTANE; 1-(4-ETHYNYLPHENYL)-4-PROPYL-2,6,7-TRIOXABICYCLO(2.2.2)OCTANE; 2,6,7 TRIOXA 1 PHOSPHABICYCLO(2.2.2)OCTANE; 2,6,7-TRIOXA-1-PHOSPHABICYCLO(2.2.2)OCTANE; 4 AMINOBUTYRIC ACID RECEPTOR; 4 AMINOBUTYRIC ACID RECEPTOR BLOCKING AGENT; FUSED HETEROCYCLIC RINGS; PHOSPHITE;

BIOASSAY; DESIGN; FLY; INSECTICIDE; ORGANIC ACID; ORGANIC COMPOUND; RODENT; THREE-DIMENSIONAL MODELING;

AMINO ACID SEQUENCE; ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYTOLOGY; DRUG EFFECT; ELECTROPHYSIOLOGY; ENZYME SPECIFICITY; HOUSE FLY; HUMAN; METABOLISM; MOLECULAR GENETICS; NERVE CELL; PHYSIOLOGY; PROTEIN CONFORMATION; RAT; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AMINO ACID SEQUENCE; ANIMALS; BICYCLO COMPOUNDS, HETEROCYCLIC; ELECTROPHYSIOLOGICAL PROCESSES; GABA ANTAGONISTS; HOUSEFLIES; HUMANS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; NEURONS; PHOSPHITES; PROTEIN CONFORMATION; RATS; RECEPTORS, GABA; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

HEXAPODA; MAMMALIA; MUSCA DOMESTICA; RATTUS;

EID: 77955992957     PISSN: 1526498X     EISSN: 15264998     Source Type: Journal    
DOI: 10.1002/ps.1973     Document Type: Article

References (28)

1. Enna SJ, The GABA receptors, in The GABA Receptors, 3rd edition, ed. By Enna SJ and Mohler H. Humana Press, Totowa, NJ, pp. 1-21 (2007).
2. Buckingham SD and Sattelle DB, GABA receptors of insects, in Comprehensive Molecular Insect Science, Vol. 5, ed. by Gilbert LI, Iatrou K and Gill SS. Elsevier Pergamon, Amsterdam, The Netherlands, pp. 107-142 (2004).
3. Ozoe Y, Takeda M, and Matsuda K, γ-Aminobutyric acid receptors: a rationale for developing selective insect pest control chemicals, in Biorational Control of Arthropod Pests-Application and Resistance Management, ed. by Ishaaya I and Horowitz AR. Springer, Heidelberg, Germany, pp. 131-162 (2009).
4. Eto M, Ozoe Y, Fujita T, and Casida JE, Significance of branched bridge-head substituent in toxicity of bicyclic phosphate esters. Agric Biol Chem 40:2113-2115 (1976).
5. Bowery NG, Collins JF and Hill RG, Bicyclic phosphorus esters that are potent convulsants and GABA antagonists. Nature 261:601-603 (1976).
6. 35S]t-Butylbicyclophosphorothionate binds with high affinity to brain-specific sites coupled to y-aminobutyric acid-A and ion recognition sites.Mol Pharmacol 23:326-336 (1983).
7. Van Renterghem C, Bilbe G, Moss S, Smart TG, Constanti A, Brown DA, etal, GABA receptors induced in Xenopus oocytes by chick brain mRNA: evaluation of TBPS as a use-dependent channel-blocker. Mol Brain Res 2:21-31 (1987).
8. Ju X-L and Ozoe Y, Bicyclophosphorothionate antagonists exhibiting selectivity for housefly GABA receptors. Pestic Sci 55:971-982 (1999).
9. Deng Y, Palmer CJ and Casida JE, House fly brain γ-aminobutyric acid-gated chloride channel: target for multiple classes of insecticides. PesticBiochem Physiol 41:60-65 (1991).
10. 3H]EBOB) in vertebrate brain and insect head. Pestic Biochem Physiol 44:1-8 (1992).
11. Palmer CJ and Casida JE, 1-(4-Ethynylphenyl)-2,6,7-trioxabicyclo[2.2.2]octanes: a new order of potency for insecticides acting at the GABA-gated chloride channel. J Agric Food Chem 37:213-216 (1989).
12. Zhao X, Salgado VL, Yeh JZ and Narahashi T, Differential actions of fipronil and dieldrin insecticides on GABA-gated chloride channels in cockroach neurons. J Pharmacol ExpTher 306:914-924 (2003).
13. Ihara M, Ishida C, Okuda H, Ozoe Y and Matsuda K, Differential blocking actions of 4'-ethynyl-4-n-propylbicycloorthobenzoate (EBOB) and γ-hexachlorocyclohexane (γ-HCH) on y-aminobutyric acid-and glutamate-induced responses of American cockroach neurons. InvertNeurosci 5:157-164 (2005).
14. Narusuye K, Nakao T, Abe R, Nagatomi Y, Hirase K and Ozoe Y, Molecular cloning of a GABA receptor subunit from Laodelphax striatella (Fallen) and patch clamp analysis of the homo-oligomeric receptors expressed in a Drosophila cell line. Insect Mol Biol 16:723-733 (2007).
15. Finney DJ, Probit Analysis, 3rd edition. Cambridge University Press, London, UK (1971).
16. Bradford MM, A rapid sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248-254 (1976).
17. Miyazawa A, Fujiyoshi Y, and Unwin N, Structure and gating mechanism of the acetylcholine receptor pore. Nature 423:949-955 (2003).
18. Halgren TA, Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94. J Comput Chem 17:490-519 (1996).
19. Nimrod DM, Fitzwater DR and Verkade JG, The crystal structure of the bicyclic phosphate OP(OCH2)3CCH3. J Am Chem Soc 90:2780-2784 (1968).
20. Ratra GS and Casida JE, GABA receptor subunit composition relative to insecticide potency and selectivity. Toxicol Lett 122:215-222 (2001).
21. Alam MS, Kajiki R, Hanatani H, Kong X, Ozoe F, Matsui Y, et al, Synthesis and structure-activity relationships of 1-phenyl-1H-1,2,3-triazoles as selective insect GABA receptor antagonists. J Agric Food Chem 54:1361-1372 (2006).
22. Alam MS, Huang J, Ozoe F, Matsumura F and Ozoe Y, Synthesis, 3D-QSAR, and docking studies of 1-phenyl-1H-1,2,3-triazoles as selective antagonists for β3 over α1β2γ2 GABA receptors. Bioorg Med Chem 15:5090-5104 (2007).
23. Sieghart W and Sperk G, Subunit composition, distribution and function of GABAa receptor subtypes. CurrTopMedChem 2:795-816 (2002).
24. Zhorov BS and Bregestovski PD, Chloride channels of glycine and GABA receptors with blockers: Monte Carlo minimization and structure-activity relationships. Biophys J 78:1786-1803 (2000).
25. Jursky F, Fuchs K, Buhr A, Tretter V, Sigel E and Sieghart W, Identification of amino acid residues of GABAa receptor subunits contributing to the formation and affinity of the tert-butylbicyclophosphorothionate binding site. J Neurochem 74:1310-1316 (2000).
26. Buckingham SD, Biggin PC, Sattelle BM, Brown LA and Sattelle DB, Insect GABA receptors: splicing, editing, and targeting by antiparasitics and insecticides. Mol Pharmacol 68:942-951 (2005).
27. Thompson M, Steichen JC and ffrench-Constant RH, Conservation of cyclodiene insecticide resistance-associated mutations in insects. Insect Mol Biol 2:149-154 (1993).
28. Ozoe Y, Ishikawa S, Tomiyama S, Ozoe F, Kozaki T, and Scott JG, Antagonism of the GABA receptor of dieldrin-resistant houseflies by fipronil and its analogues, in Synthesis and Chemistry of Agrochemicals VII, ed. by LygaJW and TheodoridisG. ACS Symposium Series 948, American Chemical Society, Washington, DC, pp. 39-50 (2007).