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Mechanism of Androgen Receptor Antagonism by Bicalutamide in the Treatment of Prostate Cancer

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Department of Chemistry and Department of Biochemistry and Molecular Biology, University of Massachusetts, 701 Lederle Graduate Research Tower, 710 North Pleasant Street, Amherst, Massachusetts 01003-9336, United States
Department of Pharmaceutical Chemistry, University of California San Francisco, 600 16th Street, San Francisco, California 94158-2517, United States
§ Shifa Biomedical, 1 Great Valley Parkway, Suite 8, Malvern, Pennsylvania 19355, United States
*Department of Chemistry, University of Massachusetts, P.O. Box 310, Leverett, MA 01054. Phone: (619) 379-9768. Fax: (425) 696-7115. E-mail: [email protected]
Cite this: Biochemistry 2011, 50, 19, 4105–4113
Publication Date (Web):April 5, 2011
Copyright © 2011 American Chemical Society

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    The androgen receptor (AR) plays a key role in regulating gene expression in a variety of tissues, including the prostate. In that role, it is one of the primary targets in the development of new chemotherapeutics for treatment of prostate cancer and the target of the most widely prescribed current drug, bicalutamide (Bcu), for this disease. In view of its importance, and the absence of a crystal structure for any antagonist–AR complex, we have conducted a series of molecular dynamics-based simulations of the AR–Bcu complex and quantum mechanical (QM) calculations of Bcu, to elucidate the structural basis for antagonism of this key target. The structures that emerge show that bicalutamide antagonizes AR by accessing an additional binding pocket (B-site) adjacent to the hormone binding site (HBS), induced by displacing helix 12. This distorts the coactivator binding site and results in the inactivation of transcription. An alternative equienergetic conformational state of bicalutamide was found to bind in an expanded hormone pocket without materially perturbing either helix 12 or the coactivator binding site. Thus, both the structural basis of antagonism and the mechanism underlying agonist properties displayed by bicalutamide in different environments may be rationalized in terms of these structures. In addition, the antagonist structure and especially the induced second site (B-site) provide a structural framework for the design of novel antiandrogens.

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