A comparative assessment of a-lipoic acid N-phenylamides as non-steroidal androgen receptor antagonists both on and off gold nanoparticles
Henderson, Luke C., Altimari, Jarrad M., Dyson, Gail, Servinis, Linden, Niranjan, Birunthi and Risbridger, Gail P. 2012, A comparative assessment of a-lipoic acid N-phenylamides as non-steroidal androgen receptor antagonists both on and off gold nanoparticles, Bioorganic chemistry, vol. 40, no. 1, pp. 1-5.
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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
Formatted title
A comparative assessment of α-lipoic acid N-phenylamides as non-steroidal androgen receptor antagonists both on and off gold nanoparticles
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.
Language
eng
Field of Research
030503 Organic Chemical Synthesis 030405 Molecular Medicine
Socio Economic Objective
970103 Expanding Knowledge in the Chemical Sciences