Xeno-oestrogens and phyto-oestrogens are alternative ligands for the androgen receptor

Hao Wang, Jiang Li, Yang Gao, Ying Xu, Ying Pan, Ichiro Tsuji, Zi Jie Sun, Xiao Meng Li

研究成果: Article査読

40 被引用数 (Scopus)

抄録

The androgen receptor (AR) plays a critical role in prostate cancer development and progression. This study aimed to use a computerized docking approach to examine the interactions between the human AR and phyto-oestrogens (genistein, daidzein, and flavone) and xeno-oestrogens (bisphenol A, 4-nonylphenol, dichlorodiphenyl trichloroethane [DDT], diethylstilbestrol [DES]). The predicted three-dimensional structure of AR and androgens was established using X-ray diffraction. The binding of four xeno-oestrogens and three phyto-oestrogens to AR was analysed. The steroids estradiol and dihydrotestosterone (DHT) were used as positive controls and thyroxine as negative control. All the ligands shared the same binding site except for thyroxine. The endogenous hormones DHT and 17Β-oestradiol showed the strongest binding with the lowest affinity energy (10 kcal mol-1). All three phyto-oestrogens and two xeno-oestrogens (bisphenol A and DES) showed strong binding to AR. The affinities of flavone, genistein, and daidzein were between 8.8 and 8.5 kcal mol-1, while that of bisphenol A was 8.1 kcal mol-1 and DES 8.3 kcal mol-1. Another two xeno-oestrogens, 4-nonylphenol and DDT, although they fit within the binding domain of AR, showed weak affinity (6.4 and 6.7 kcal mol 1, respectively). The phyto-oestrogens genistein, daidzein and flavone, and the xeno-oestrogens bisphenol A and DES can be regarded as androgenic effectors. The xeno-oestrogens DDT and 4-nonylphenol bind only weakly to AR.

本文言語English
ページ(範囲)535-547
ページ数13
ジャーナルAsian Journal of Andrology
12
4
DOI
出版ステータスPublished - 2010 7月

ASJC Scopus subject areas

  • 泌尿器学

フィンガープリント

「Xeno-oestrogens and phyto-oestrogens are alternative ligands for the androgen receptor」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル