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A comparative assessment of a-lipoic acid N-phenylamides as non-steroidal androgen receptor antagonists both on and off gold nanoparticles
journal contributionposted on 2012-01-01, 00:00 authored by Luke HendersonLuke Henderson, Jarrad Altimari, Gail Dyson, Linden Servinis, B Niranjan, G Risbridger
A group of α-lipoic acid N-phenylamides were synthesized employing a variety of amide coupling protocols utilizing electron deficient anilines. These compounds were then assessed for their ability to block androgen-stimulated proliferation of a human prostate cancer cell line, LNCaP. These structurally simple compounds displayed anti-proliferative activities at, typically, 5–20 μM concentrations and were comparable to a commonly used anti-androgen Bicalutamide®. The inclusion of a disulfide (RS-SR) moiety, serving as an anchor to several metal nanoparticle systems (Au, Ag, Fe2O3, etc.), does not impede any biological activity. Conjugation of these compounds to a gold nanoparticle surface resulted in a high degree of cellular toxicity, attributed to the absence of a biocompatible group such as PEG within the organic scaffold.