Synthesis and biological activity of ferrocenyl derivatives of the non-steroidal antiandrogens flutamide and bicalutamide |
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Authors: | Olivier Payen Anne Vessières Agnès Lauzier Michael J McGlinchey Gérard Jaouen |
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Institution: | a Chimie ParisTech (Ecole Nationale Supérieure de Chimie de Paris), Laboratoire Charles Friedel, UMR CNRS 7223, 11 rue Pierre et Marie Curie, 75231 Paris Cedex 05, France b UCD School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland c Université Pierre et Marie Curie, 4 Place Jussieu, 75005 Paris, France |
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Abstract: | A series of ferrocenyl derivatives of the two non steroidal antiandrogens flutamide and bicalutamide have been prepared. Ferrocenyl bicalutamide complexes were initially synthesized in their racemic forms, and subsequently prepared as pure (R) and (S) enantiomers, and their structure was determined by X-ray crystallography. Most of the complexes retain a modest affinity for the androgen receptor and show an antiproliferative effect on both hormone-dependent (LNCaP) and -independent (PC-3) prostate cancer cells. Ferrocenyl derivatives of bicalutamide are the most cytotoxic (IC50 values on PC-3 around 15 μM); however, they are less potent than the ferrocenyl derivatives of ethynyltestosterone or nilutamide (IC50 around 5 μM). |
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Keywords: | Anticancer agents Antiandrogen Ferrocene Prostate cancer Flutamide Bicalutamide |
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