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Title: Evaluation of hydrogen bonds of ecdysteroids in the ligand-receptor interactions using a protein modeling system
Authors: Harada, Toshiyuki
Nakagawa, Yoshiaki  kyouindb  KAKEN_id
Akamatsua, Miki
Miyagawa, Hisashi  kyouindb  KAKEN_id  orcid (unconfirmed)
Author's alias: 中川, 好秋
Keywords: CoMFA
Drosophila melanogaster
Ecdysone receptor
Hydrogen bond
Ponasterone A
Issue Date: Aug-2009
Publisher: Elsevier
Journal title: Bioorganic and Medicinal Chemistry
Volume: 17
Issue: 16
Start page: 5868
End page: 5873
Abstract: The insect molting hormone, 20-hydroxyecdysone (20E) and its analogs (ecdysteroids) specifically bind to the ecdysone receptor. Previously, we synthesized various ecdysteroids containing the side chain moiety of ponasterone A (PonA), and measured the binding activity against Drosophila Kc cells to study the structure–activity relationship. Here we quantitatively analyzed the structure–activity relationship for the ligand binding of ecdysteroids including 20E and PonA. Since the hydrogen bonding (HB) is one of the important physicochemical properties for ligand binding to the ecdysteroid receptor, the number of possible HBs between the ligand molecule and the receptor was manually counted in the modeled ligand–receptor complex for all compounds. The construction of the ligand–receptor model was executed by the full-automatic modeling system (FAMS) in which calculation was done by simulated annealing. The binding potency of 15 ecdysteroids to Kc-cells were linearly correlated (r2 = 0.63) with the number of HBs which are observed between ligand and receptor molecule. Contribution of steric and electrostatic effects on the ligand–receptor binding was also examined using a three-dimensional quantitative structure–activity relationship (3-D QSAR), comparative molecular field analysis (CoMFA).
Rights: c 2009 Elsevier Ltd. All rights reserved.
This is not the published version. Please cite only the published version.
DOI(Published Version): 10.1016/j.bmc.2009.07.011
PubMed ID: 19631551
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