title: A comparative assessment of α-lipoic acid N-phenylamides as non-steroidal androgen receptor antagonists both on and off gold nanoparticles.
abstract: 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, Fe(2)O(3), 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.
authors.affiliation: Deakin University, Pigdons Road, Waurn Ponds Campus, Geelong, Victoria 3216, Australia. Electronic address: luke.henderson@deakin.edu.au.
authors.forename: Luke C
authors.initials: LC
authors.lastname: Henderson
authors.affiliation: Deakin University, Pigdons Road, Waurn Ponds Campus, Geelong, Victoria 3216, Australia.
authors.forename: Jarrad M
authors.initials: JM
authors.lastname: Altimari
authors.affiliation: Deakin University, Pigdons Road, Waurn Ponds Campus, Geelong, Victoria 3216, Australia.
authors.forename: Gail
authors.initials: G
authors.lastname: Dyson
authors.affiliation: Deakin University, Pigdons Road, Waurn Ponds Campus, Geelong, Victoria 3216, Australia.
authors.forename: Linden
authors.initials: L
authors.lastname: Servinis
authors.affiliation: Department of Anatomy and Developmental Biology, Faculty of Medicine, Nursing & Health Sciences, Monash University, Victoria 3800, Australia.
authors.forename: Birunthi
authors.initials: B
authors.lastname: Niranjan
authors.affiliation: Department of Anatomy and Developmental Biology, Faculty of Medicine, Nursing & Health Sciences, Monash University, Victoria 3800, Australia.
authors.forename: Gail P
authors.initials: GP
authors.lastname: Risbridger
mesh_terms: D000178:Acrylamides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D059002:Androgen Receptor Antagonists / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D000813:Anilides / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D006046:Gold / Q000737:chemistry*; D006801:Humans; D053768:Metal Nanoparticles / Q000737:chemistry*; D009570:Nitriles / Q000494:pharmacology; D011944:Receptors, Androgen / Q000737:chemistry* / Q000378:metabolism; D013499:Surface Properties; D008063:Thioctic Acid / Q000737:chemistry*; D014105:Tosyl Compounds / Q000494:pharmacology
chemical_list: D000178:Acrylamides; D059002:Androgen Receptor Antagonists; D000813:Anilides; D000970:Antineoplastic Agents; C560143:N-phenylacrylamide; D009570:Nitriles; D011944:Receptors, Androgen; D014105:Tosyl Compounds; D008063:Thioctic Acid; D006046:Gold; C053541:bicalutamide