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Abstract

Volume 12, Issue 4 (July 2010) 12, 535–547; 10.1038/aja.2010.14

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

Hao Wang1,*, Jiang Li2,*, Yang Gao1, Ying Xu1, Ying Pan1, Ichiro Tsuji3, Zi-Jie Sun4 and Xiao-Meng Li1

1 School of Life Sciences, Northeast Normal University, Changchun 1.30024, China
2 Dental Hospital, Jilin University, Changchun 130041, China
3 Department of Public Health, Tohoku University, Sendai 980-8576, Japan
4 Departments of Urology and Genetics, Stanford University School of Medicine, Stanford, CA 94303-5118, USA

* These two authors contributed equally to this work.

Correspondence: Dr Xiao-Meng Li, lixm441@nenu.edu.cn

Received 20 November 2009; Revised 17 December 2009; Accepted 24 February 2010; Published online 3 May 2010.

Abstract

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.

Keywords: androgen receptor; dock; phyto-oestrogens; xeno-oestrogens

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