Protein structure based rational design of ecdysone agonists

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 12, 2009, Pages 4064-4070

  Holmwood, Graham ^a   Schindler, Michael ^a  

^a BAYER CROPSCIENCE AG   (Germany)

Author keywords

Dibenzoylhydrazide; Ecdysteroids; Insecticides; Nuclear receptors; Protein X ray structures; Rational design

Indexed keywords

CELL NUCLEUS RECEPTOR; ECDYSONE; ECDYSONE RECEPTOR; INSECTICIDE; PHYTOHORMONE; STEROID HORMONE;

ARTICLE; BINDING SITE; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; HYDROGEN BOND; INSECT; LIGAND BINDING; NONHUMAN; PROTEIN BINDING; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; QUANTITATIVE STRUCTURE ACTIVITY RELATION; QUANTUM MECHANICS; SEQUENCE HOMOLOGY; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

COMPUTER-AIDED DESIGN; CRYSTALLOGRAPHY, X-RAY; HYDRAZINES; INSECTICIDES; PROTEIN STRUCTURE, TERTIARY; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RECEPTORS, STEROID;

HEXAPODA;

EID: 66349093047     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.01.008     Document Type: Article

References (39)

1. Germain P., Altucci L., Bourguet W., Rochette-Egly C., and Gronemeyer H. Pure Appl. Chem. 75 (2003) 1619
2. Thornton J.W. Pure Appl. Chem. 75 (2003) 1827
3. Dhadialla T.S., and Ross Jr. R. In: Kraemer W., and Schirmer U. (Eds). Modern Crop Protection Compounds Vol. 3 (2007), WILEY-VCH GmbH & KGaA, Weinheim 773-796
4. Yanagi M., Tsukamoto Y., Watanabe T., and Kawagishi A. J. Pestic. Sci. 31 (2006) 163
5. Sawada Y., Yanai T., Nakagawa H., Tsukamoto Y., Yokoi S., Yanagi M., Toya T., Sugizaki H., Kato Y., Shirakura H., Watanabe T., Yajima Y., Kodama S., and Masui A. Pest Manage. Sci. 59 (2003) 25
6. Nakagawa Y., Hattori K., Shimizu B., Akamatsu M., Miyagawa H., and Ueno T. Pestic. Sci. 53 (1998) 267
7. Hormann R.E., and Dinan L. In: Gilbert L.I., Iatrou K., and Gill S.S. (Eds). Comprehensive Insect Molecular Science Vol. 3 (1997), Elsevier Pergamon, New York 198-236
8. Hsu A.C.T., Fujimoto T.T., and Dhadialla T.S. In: Hedin P.A. (Ed). Phytochemicals for pest control. ACS Symposium Series Vol. 658 (1997), American Chemical Society, Washington, DC 206-219
9. Nakagawa Y., Takahashi K., Kishikawa H., Ogura T., Minakuchi C., and Miyagawa H. Bioorg. Med. Chem. 13 (2005) 1333
10. Wheelock C.E., Nakagawa Y., Harada T., Oikawa N., Akamatsu M., Smagghe G., Stefanou D., Iatrou K., and Swevers L. Bioorg. Med. Chem. 14 (2006) 1143
11. Fujita T., and Nakagawa Y. SAR QSAR Environ. Res. 18 (2007) 77
12. Chan T.H., Ali A., Britten J.F., Thomas A.W., Strunz G.M., and Salonius A. Can. J. Chem. 68 (1990) 1178
13. Huber R., and Hoppe W. Chem. Ber. 98 (1965) 2403
14. Fabian L., Argay G., Kalman A., and Bathori M. Acta Crystallogr., Sect. B 58 (2002) 710
15. Dinan L., Hormann R.E., and Fujimoto T. J. Computer-Aided Mol. Des. 13 (1999) 185
16. Nakagawa Y., Shimizu B., Oikawa N., Akamatsu M., Nishimura K., Kurihara N., Ueno T., and Fujita T. In: Hansch C., and Fujita T. (Eds). Classical and Three-Dimensional QSAR in Agrochemistry. ACS Symposium Series Vol. 606 (1995), Oxford University Press, Washington, DC 288-301
17. Qian X. J. Agric. Food Chem. 44 (1996) 1538
18. Reynolds C.H., and Hormann R.E. J. Am. Chem. Soc. 118 (1996) 9395
19. 20,21
20. Weigend F., and Ahlrichs R. Phys. Chem. Chem. Phys. 7 (2005) 3297
21. Ahlrichs R., Bär M., Häser M., Horn H., and Kölmel C. Chem. Phys. Lett. 162 (1989) 165
22. Klamt A., Jonas V., Bürger T., and Lohrenz J.C.W. J. Phys. Chem. A 102 (1998) 5074
23. Folkertsma S., van Noort P.I., Brandt R.F.J., Bettler E., Vriend G., and de Vlieg J. Curr. Med. Chem. 12 (2005) 1001
24. Wurtz J.-M., Guillot B., Fagart J., Moras D., Tietjen K., and Schindler M. Protein Sci. 9 (2000) 1073
25. Santos A.C.S., and SantAnna C.M.R. J. Mol. Struct.(Theochem) 585 (2002) 61
26. Kasuya A., Sawada Y., Tsukamoto Y., Tanaka K., Toya T., and Yanagi M. J. Mol. Model. 9 (2003) 58
27. Billas I.M.L., Iwema T., Garnier J.-M., Mitschler A., Rochel N., and Moras D. Nature 426 (2003) 91
28. Browning, C.; Chavant, V.; Moras, D.; Billas, I. M. L., et al., submitted for publication.
29. Hormann R.E., Smagghe G., and Nakagawa Y. QSAR Comb. Sci. 27 (2008) 1098
30. Carmichael J.A., Lawrence M.C., Graham L.D., Pilling P.A., Epa V.C., Noyce L., Lovrecz G., Winkler D.A., Pawlak-Skrzecz A., Eaton R.E., Hannan G.N., and Hill R.J. J. Biol. Chem. 280 (2005) 22258
31. Iwema T., Billas I.M.L., Beck Y., Bonneton F., Nierengarten H., Chaumot H., Richards G., Laudet V., and Moras D. EMBO J. 26 (2007) 3770
32. Browning C., Martin E., Loch C., Wurtz J.-M., Moras D., Stote R.H., Dejaegere A.P., and Billas I.M.L. J. Biol. Chem. 282 (2007) 32924
33. Minakuchi C., Ogura T., Miyagawa H., and Nakagawa Y. J. Pestic. Sci. 32 (2007) 379
34. Steglich W., and Höfle G. Angew. Chem. 81 (1969) 1001
35. Engel N., and Steglich W. Liebigs Ann. Chem. (1978) 1916
36. Engel, N. Thesis, Univ. Bonn, 1979.
37. Holmwood, G. et al. WO2003/004464.
38. Schwarz, H. G. et al. WO2006/094666.
39. Kröhnke F. Synthesis (1976) 1