Competitive antagonism of insect GABA receptors by iminopyridazine derivatives of GABA

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 19, 2012, Pages 5957-5964

  Rahman, Mohammad Mostafizur ^a   Akiyoshi, Yuki ^b   Furutani, Shogo ^c   Matsuda, Kazuhiko ^c   Furuta, Kenjiro ^b   Ikeda, Izumi ^a,b   Ozoe, Yoshihisa ^a,b  

^a TOTTORI UNIVERSITY   (Japan)

^b SHIMANE UNIVERSITY   (Japan)

^c KINKI UNIVERSITY   (Japan)

Author keywords

Competitive antagonism; GABA receptor; GABA gated chloride channel; Iminopyridazine; Insect; Insecticide

Indexed keywords

2 NAPHTHYL DERIVATIVE; 3 THIENYL DERIVATIVE; 3,4 METHYLENEDIOXYPHENYL; 4 AMINOBUTYRIC ACID DERIVATIVE; 4 AMINOBUTYRIC ACID RECEPTOR; 4 AMINOBUTYRIC ACID RECEPTOR BLOCKING AGENT; 4 BIPHENYL DERIVATIVE; 4 PHENOXYPHENYL DERIVATIVE; BUTYRIC ACID DERIVATIVE; IMINOPYRIDAZINE DERIVATIVE; INSECT PROTEIN; LIGAND; PESTICIDE; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; COCKROACH; CONTROLLED STUDY; FLUORESCENCE ANALYSIS; GABAERGIC SYSTEM; LIGAND BINDING; MEMBRANE POTENTIAL; MOLECULAR DOCKING; NONHUMAN; PATCH CLAMP; RECEPTOR BLOCKING; SYNTHESIS;

ANIMALS; GABA ANTAGONISTS; GAMMA-AMINOBUTYRIC ACID; INSECT PROTEINS; INSECTICIDES; INSECTS; MOLECULAR DOCKING SIMULATION; PYRIDAZINES; RECEPTORS, GABA;

BLATTARIA; HEXAPODA; LAODELPHAX STRIATELLUS; PERIPLANETA AMERICANA;

EID: 84866355359     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.07.049     Document Type: Article

References (37)

1. W. Hevers, and H. Lüddens Mol. Neurobiol. 18 1998 35
2. B. Bettler, K. Kaupmann, J. Mosbacher, and M. Gassmann Physiol. Rev. 84 2004 835
3. S.M. Sine, and A.G. Engel Nature 440 2006 448
4. P.J. Whiting, T.P. Bonnert, R.M. McKernan, S. Farrar, B. Le Bourdellés, R.P. Heavens, D.W. Smith, L. Hewson, M.R. Rigby, D.J.S. Sirinathsinghji, S.A. Thompson, and K.A. Wafford Ann. N.Y. Acad. Sci. 868 1999 645
5. G.A.R. Johnston Pharmacol. Ther. 69 1996 173
6. B.J. Krishek, S.J. Moss, and T.G. Smart Neuropharmacology 35 1996 1289
7. Buckingham, S. D.; Sattelle, D. B. In Gilbert, L. I., Iatrou, K., Gill, S. S., Eds.; Comprehensive Molecular Insect Science; Elsevier Pergamon: Amsterdam, 2004; Vol. 5, pp. 107-142.
8. R.H. ffrench-Constant, T.A. Rocheleau, J.C. Steichen, and A.E. Chalmers Nature 363 1993 449
9. M. Mezler, T. Müller, and K. Raming Eur. J. Neurosci. 13 2001 477
10. G. Gisselmann, J. Plonka, H. Pusch, and H. Hatt Br. J. Pharmacol. 142 2004 409
11. S.D. Buckingham, P.C. Biggin, B.M. Sattelle, L.A. Brown, and D.B. Sattelle Mol. Pharmacol. 68 2005 942
12. Y. Ozoe, M. Takeda, and K. Matsuda I. Ishaaya, A.R. Horowitz, Biorational Control of Arthropod Pests 2009 Springer Heidelberg 131 162
13. V. Raymond-Delpech, K. Matsuda, B.M. Sattelle, J.J. Rauh, and D.B. Sattelle Invert. Neurosci. 5 2005 119
14. S. Ueno, J. Bracamontes, C. Zorumski, D.S. Weiss, and J.H. Steinbach J. Neurosci. 17 1997 625
15. J.-P. Chambon, P. Feltz, M. Heaulme, S. Restle, R. Schlichter, K. Biziere, and C.G. Wermuth Proc. Natl. Acad. Sci. U.S.A. 82 1985 1832
16. A.M. Hosie, and D.B. Sattelle Br. J. Pharmacol. 119 1996 1577
17. H. Satoh, H. Daido, and T. Nakamura Neurosci. Lett. 381 2005 125
18. K. Narusuye, T. Nakao, R. Abe, Y. Nagatomi, K. Hirase, and Y. Ozoe Insect Mol. Biol. 16 2007 723
19. C.-G. Wermuth, J.-J. Bourguignon, G. Schlewer, J.-P. Gies, A. Schoenfelder, A. Melikian, M.-J. Bouchet, D. Chantreux, J.-C. Molimard, M. Heaulme, J.-P. Chambon, and K. Biziere J. Med. Chem. 30 1987 239
20. A. Melikian, G. Schlewer, J.-P. Chambon, and C.G. Wermuth J. Med. Chem. 35 1992 4092
21. N. Gavande, G.A.R. Johnston, J.R. Hanrahan, and M. Chebib Org. Biomol. Chem. 8 2010 4131
22. K.S. Schroeder, and B.D. Neagle J. Biomol. Screen. 1 1996 75
23. C. Joesch, E. Guevarra, S.P. Parel, A. Bergner, P. Zbinden, D. Konrad, and H. Albrecht J. Biomol. Screen. 13 2008 218
24. E. Aydar, and D.J. Beadle J. Insect Physiol. 45 1999 213
25. P.S. Miller, and T.G. Smart Trends Pharmacol. Sci. 31 2010 161
26. R.E. Hibbs, and E. Gouaux Nature 474 2011 54
27. T. Sander, B. Frolund, A.T. Bruun, I. Ivanov, J.A. McCammon, and T. Balle Proteins 79 2011 1458
28. S.C.R. Lummis, I. McGonigle, J.A. Ashby, and D.A. Dougherty J. Neurosci. 31 2011 12371
29. J. Amin, and D.S. Weiss Nature 366 1993 565
30. J.H. Holden, and C. Czajkowski J. Biol. Chem. 277 2002 18785
31. E. Sigel, R. Baur, S. Kellenberger, and P. Malherbe EMBO J. 11 1992 2017
32. J. Zhang, F. Xue, and Y. Chang Mol. Pharmacol. 74 2008 941
33. A.J. Boileau, J.G. Newell, and C. Czajkowski J. Biol. Chem. 277 2002 2931
34. J.G. Newell, and C. Czajkowski J. Biol. Chem. 278 2003 13166
35. F. Iqbal, R. Ellwood, M. Mortensen, T.G. Smart, and J.R. Baker Bioorg. Med. Chem. Lett. 21 2011 4252
36. I. Yamamoto, J.E. Carland, K. Locock, N. Gavande, N. Absalom, J.R. Hanrahan, R.D. Allan, G.A.R. Johnston, and M. Chebib ACS Chem. Neurosci. 3 2012 293
37. C. Van der Brempt, G. Evrard, and F. Durant Acta Cryst. C42 1986 1206