A new model for 20-hydroxyecdysone and dibenzoylhydrazine binding: A homology modeling and docking approach

Protein Science

Volumn 9, Issue 6, 2000, Pages 1073-1084

  Wurtz, Jean Marie ^a   Guillot, Benoit ^a,c   Fagart, Jérôme ^a   Moras, Dino ^a   Tietjen, Klaus ^b   Schindler, Michael ^b  

^a INSTITUT DE GÉNÉTIQUE ET DE BIOLOGIE MOLÉCULAIRE ET CELLULAIRE   (France)

^b BAYER AG   (Germany)

^c Nancy University CNRS   (France)

Author keywords

Dibenzoylhydrazine; Docking; Ecdysone; Molecular modeling; Nuclear receptor

Indexed keywords

CELL NUCLEUS RECEPTOR; ECDYSTERONE; HYDRAZINE DERIVATIVE; INSECTICIDE; RETINOIC ACID RECEPTOR; VITAMIN D RECEPTOR;

ARTICLE; BINDING AFFINITY; CRYSTAL STRUCTURE; HORMONE RECEPTOR INTERACTION; INSECT; LIGAND BINDING; MOLECULAR INTERACTION; MOLECULAR MODEL; NONHUMAN; PRIORITY JOURNAL; RECEPTOR BINDING;

CHIRONOMUS TENTANS; INSECTA; INVERTEBRATA;

EID: 0033937681     PISSN: 09618368     EISSN: None     Source Type: Journal    
DOI: 10.1110/ps.9.6.1073     Document Type: Article

References (61)

1. Barton GJ. 1993. ALSCRIPT: A tool to format multiple sequence alignments. Protein Eng 6:37-40.
2. Bourget W, Ruff M, Chambon P, Gronemeyer H, Moras D. 1995. Crystal structure of the ligand-binding domain of the human nuclear receptor RXR-a. Nature 375:377-382.
3. Brode S, Horn H, Ehrig M, Moldrup D, Rice JE, Ahlrichs R. 1993. Parallel direct SCF and gradient program for workstation clusters. J Comput Chem 14:1142-1148.
4. Brzozowski AM, Pike AC, Dauter Z, Hubbard RE, Bonn T, Engstrom O, Öhmann L, Greene GL, Gustafsson JA, Carlquist M. 1997. Molecular basis of agonism and antagonism in the oestrogen receptor. Nature 389:753-757.
5. Chan TH, Ali A, Britten JF, Thomas AW, Strunz GM, Salonius A, 1990. The crystal structure of 1,2-dibenzoyl-1-tert-butylhydrazine, a nonsteroidal ecdysone agonist, and its effect on spruce budworm (Choristoneura fumiferana). Can J Chem 68:1178-1181.
6. Cherbas P, Cherbas L, Lee SS, Nakanishi K, 1988. 26-[1251]Iodoponasterone A is a potent ecdysone and a sensitive radioligand for ecdysone receptors. Proc Natl Acad Sci USA 85:2096-2100).
7. Cho WL, Zapitskaya MZ, Raikhel AS, 1995. Mosquito ecdysteroid receptor: Analysis of the cDNA and expression during vitellogenesis. Ins Biochem Molec Biol 25:19-27.
8. Chung AC, Durica DS, Clifton SW, Roe BA, Hopkins PM. 1998. Cloning of crustacean ecdysteroid receptor and retinoid-X receptor gene homologs and elevation of retinoid-X receptor mRNA by retinoic acid. Mol Cell Endocrinol 139:209-227.
9. Cottam DM, Milner MJ. 1997. The effect of several ecdysteroids and ecdysteroid agonists on two Drosophila imaginal disk cell lines. Cell Mol Life Sci 53:600-603.
10. Cramer RD, Patterson DE, Bunce JD. 1989. Recent advances in comparative molecular field analysis (CoMFA). Prog Clin Biol Res 291:161-165.
11. Dhadialla TS, Tzertzinis G. 1997. Characterization and partial cloning of ecdysteroid receptor from a cotton boll weevil embryonic cell line. Arch Insect Biochem Physiol 35:45-57.
12. Elbrecht A, Chen Y, Jurgens T, Hensens OD, Zink DL, Beck HT, Balick MJ, Borris R. 1996. 8-O-Acetylharpagide is a nonsteroidal ecdysteroid agonist. Ins Biochem Molec Biol 26:519-523.
13. Evans SV, 1993. SETOR: Hardware lighted three-dimensional solid model representations of macromolecules. J Mol Graphics 11:134-138.
14. Fujiwara J, Jindra M, Newitt R, Palli SR, Hiruma K, Riddiford I.M. 1995. Cloning of an ecdysone receptor homolog from Munduca sexta and the developmental profile of its mRNA in wings. Ins Biochem Molec Biol 25:845-856.
15. Gronemeyer H, Laudet V. 1995. Transcription factors 3: Nuclear receptors. Protein Profile 2:1173-1308.
16. Guo X, Harmon MA, Laudet V, Mangelsdort DJ, Palmer MJ. 1998. Isolation of a functional ecdysteroid receptor homologue from the ixodid tick Amblyomma americanum. Ins Biochem Molec Biol 27:945-962.
17. Hannan GN, Hill RJ. 1997. Cloning and characterization of LcECR: A functional ecdysone receptor from the sheep blowfly Lucilia cuprina. Ins Biochem Molec Biol 27:479-488.
18. Harmatha J, Dinan L. 1997. Biological activity of natural and synthetic ecdysteroids in the BII bioassay. Arch Insect Biochem Physiol 35:219-225.
19. Hendlich M, Lackner P, Weitckus S, Floeckner H, Froschauer R, Gottsbacher K. Casari G, Sippl MJ. 1990. Identification of native protein folds amongst a large number of incorrect models. The calculation of low energy conformations from potentials of mean force. J Mol Biol 216:167-180.
20. Hsu AC, Fujimoto TT, Dhadialla TS. 1997. Structure-activity study and conformational analysis of RH-5992, the first commercialized nonsteroidal ecdysone agonist. ACS Symp Ser 658:206-219.
21. Huber R, Hoppe W. 1965. On the chemistry of ecdysone. VII. Analysis of the crystal and molecular structure of the molting hormone in insects, ecdysone, using the automized folding molecule method. Chem Ber 98:2403-2424.
22. Imhof MO, Rusconi S, Lezzi M. 1993. Cloning of a Chironomus tentans cDNA encoding a protein (cECRH) homologous to the Drosophila melanogaster ecdysteroid receptor (dECR). Ins Biochem Molec Biol 23:115-124.
23. Jepson I, Martinez A, Greenland AJ. 1996. A gene switch comprising an ecdysone receptor. Inter Patent Applic WO 96/37609.
24. Jones G, Sharp PA. 1997. Ultraspiracle: An invertebrate nuclear receptor for juvenile hormones. Proc Natl Acad Sci USA 94:499-413.
25. Jones TA, Zou JY, Cowan SW, Kjeldgaard. 1991. Improved methods for binding protein models in electron density maps and the location of errors in these models. Acta Crystallogr A7:110-119.
26. Kayser H, Winkler T, Spindler-Barth M. 1997. 26-Hydroxylation of ecdysteroids is catalyzed by a typical cytochrome P-450-dependent oxidase and related to ecdysteroid resistance in an insect cell line. Eur J Biochem 248:707-716.
27. Klamt A, Schüürmann G. 1993. COSMO: A new approach to dielectric screening in solvents with explicit expressions fot the screening energy and its gradient. Perkin Trans 799.
28. Kleywegt GJ, Jones TA. 1994. Detection, delineation, measurement and display of cavities in macromolecular structures. Acta Crystallogr D50:178-185.
29. Koelle MR, Talbot WS, Segraves WA, Bender MT, Cherbas P, Hogness DS. 1991. The Drosophila ECR gene encodes an ecdysone receptor, a new meber of the steroid receptor superfamily. Cell 67:59-77.
30. Kothapalli R, Palli SR, Ladd TR, Sohi SS, Cress D, Dhadialla TS, Tzertzinis G, Retnakaran A. 1995. Cloning and developmental expression of the ecdysone receptor gene from the spruce budworm, Choristineura fumiferana. Dev Genet 17:319-330.
31. Lafont R. 1997. Ecdysteroids and related molecules in animals and plants. Arch Insect Biochem Physiol 35:3-20.
32. Laskowski RA, MacArthur MW, Moss DS, Thornton JM. 1993. PROCHECK: A program to check the stereochemical quality of proteins structures. J Appl Crystallogr 26:283-291.
33. Mikitani K. 1996. A new nonsteroidal chemical class of ligand for the ecdysteroid receptor 3, 5-di-tert-butyl-4-hydroxy-N-isobutyl-benzamide shows apparent insect molting hormone activities at molecular and cellular levels. Biochem Biophys Res Com 227:427-43.
34. Mohammed-Ali AK, Chan TH, Thomas AW, Strunz GM, Jewett B. 1995. Structure-activity relationship study of synthetic hydrazines as ecdysone agonists in the control of spruce budworm (Choristoneura fumiferana). Can J Chem 73:550-557.
35. Moras D, Gronemeyer H. 1999. The nuclear receptor ligand-binding domain: Structure and function. Curr Opin Cell Biol 10:384-391.
36. Mouillet JF, Delbecque JP, Quennedy B, Delachambre J. 1997. Cloning of two putative ecdysteroid receptor isoforms from Tenebrio molitor and their developmental expression in the epidermis during metamorphosis. Eur J Biochem 248:856-863.
37. Nakagawa Y, Shimizu B, Oikawa N, Akamatsu M, Nishimura K, Kurihara N, Ueno T, Fujita T. 1995 Three-dimensional quantitative structure-activity analysis of steroidal and dibenzoylhydrazine-type ecdysone agonists. ACS Symp Ser 606:288-301.
38. Nicholls A, Sharp KA, Honig B. 1991. Protein folding and association: Insights from the interfacial and thermodynamic properties of hydrocarbons. Proteins 11:281-296.
39. Nolte RT, Wisely GB, Westin S, Cobb JE, Lambert MH, Kurokawa R, Rosenfeld MG, Willson TM, Glass CK, Milburn MV. 1998. Ligand binding and co-activator assembly of the peroxisome proliferator-activated receptor-gamma. Nature 395:137-143.
40. Oikawa N, Nakagawa Y, Nishimura K, Ueno T, Fujita T. 1994a. Quantitative structure-activity analysis of larvicidal 1-(substituted benzoyl)-2-benzoyl-1-tert-butylhydrazines against Chilo suppressalis. Pestic Sci 41:139-148.
41. Oikawa N, Nakagawa Y, Nishimura K, Ueno T, Fujita T. 1994b. Quantitative structure-activity studies of insect growth regulators. X. Substituent effects on larvicidal activity of 1-tert-1-(2-chlorobenzoyl)-2-(substituted benzoyl-)hydrazines against Chilo suppresalis of potent derivatives. Pest Biochem Physiol 48:135-144.
42. Qian X. 1996. Molecular modeling study on the structure-activity relationship of substituted dibenzoyl-1-tert-butylhydrazines and their structural similarity to 20-hydroxyecdysone. J Agric Food Chem 44:1538-1542.
43. Renaud JP, Rochel N, Ruff M, Vivat V, Chambon P, Gronemeyer H, Moras D. 1995. Crystal structure of the RAR.gamma, ligand-binding domain bound to all-trans retinoic acid. Nature 378:681-689.
44. Reynolds CH, Hormann RE. 1996. Theoretical study of the structure and rotational flexibility of diacylhydrazines: Implications for the structure of nonsteroidal ecdysone agonists and azapeptides. J Am Chem Soc 118:395-391.
45. Rochel N, Wurtz JM, Mitschler A, Klaholz B, Moras D. 2000. Crystal structure of the nuclear receptor for vitamin D bound to its natural ligand. Mol Cell 5:173-179.
46. Roussel PG, Sik V, Turner NJ, Dinan LN. 1997. Synthesis and biological activity of side-chain analogs of ecdysone and 20-hydroxyecdysone. J Chem Soc. Perkin Trans 1:2237-2246.
47. Sali A, Blundell TL. 1993. Comparative protein modeling by satisfaction of spatial restraints. J Mol Biol 234:779-815.
48. Shiau AK, Barstad D, Loria PM, Cheng L, Kushner PJ, Agard DA, Greene GL, 1998. The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen. Cell 95:927-937.
49. Shimizu BI, Nakagawa Y, Hattori K, Nishimura K, Kurihara N, Ueno T. 1997. Molting hormonal and larvicidal activities of aliphatic acyl analogs of dibenzoylhydrazine insecticides. Steroids 62:638-642.
50. Smagghe G, Eelen H, Verschelde E, Richter K, Degheele D. 1996. Differential effects of nonsteroidal ecdysteroid agonists in Coleoptera and Lepidoptera: Analysis of evagination and receptor binding in imaginal disks. Insect Biochem Mol Biol 20:687-695.
51. Spindler-Barth M, Quack S, Rauch P, Spindler KD. 1997. Biological effects of muristerone A and turkesterone on the epithelial cell line from Chironomus tentans (D: Chironomidae) and correlation with binding affinity to the ecdysteroid receptor. Eur J Entomol 94:161-166.
52. Swevers L, Drevet JR, Lunke MD, Iatrou K. 1995. Cloning and analysis of expression during follicular cell differentiation. Ins Biochem Molec Biol 25:857-866.
53. Talbot WS, Swyryd EA, Hogness DS. 1993. Drosophila tissues with different metamorphic responses to ecdysone express different ecdysone receptor isoforms. Cell 73:1323-1337.
54. Tanenbaum DM, Wang Y, Williams SP, Sigler PB. 1998. Crystallographic comparison of the estrogen and progesterone receptor's ligand binding domains. Proc Natl Acad Sci USA 95:5998-6003.
55. Thompson JD, Higgins DG, Gibson TJ. 1994. CLUSTAL W: Improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res 22:4673-4680.
56. Thummel CS. 1995. The regulation and function of Drosophila nuclear receptor superfamily members. Cell 83:871-877.
57. Thummel CS. 1996. Flies on steroids - Drosophila metamorphosis and the mechanism of steroid hormone action. Trends in Genet 12:306-310.
58. Wagner RL, Apriletti JW, McGrath ME, West BL, Baxter JD, Fletterick RJ. 1995. A structural role for hormone in the thyroid hormone receptor. Nature 378:690-697.
59. Williams SP, Sigler PB. 1998. Atomic structure of progesterone complexed with its receptor. Nature 393:392-396.
60. Wing KD, Slawecki RA, Carlson GR. 1988. RH5849, a nonsteroidal ecdysone agonist: Effects on larval Lepidoptera. Science 241:470-472.
61. Wurtz, JM, Bourguet W, Renaud JP, Vivat V, Chambon P, Moras D, Gronemeyer H. 1996. A canonical structure for the ligand-binding domain of nuclear receptors. Nat Struct Biol 3:87-94.