First synthesis of separable isomeric testosterone dimers showing differential activities on prostate cancer cells

• Published in: Bioorganic & medicinal chemistry letters Vol. 20; no. 7; pp. 2078 - 2081
• Main Authors: Bastien, Dominic, Leblanc, Valérie, Asselin, Éric, Bérubé, Gervais
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Ltd 01.04.2010; Elsevier
• Subjects: Androgen Antagonists - chemical synthesis; Androgen Antagonists - chemistry; Androgen Antagonists - pharmacology; Androgen receptor; Antineoplastic agents; Antineoplastic Agents, Hormonal - chemical synthesis; Antineoplastic Agents, Hormonal - chemistry; Antineoplastic Agents, Hormonal - pharmacology; Biological and medical sciences; Cell Line, Tumor; Cell Proliferation - drug effects; Crystallography, X-Ray; Dimers; Drug Screening Assays, Antitumor; General aspects; Humans; Isomerism; Male; Medical sciences; Models, Molecular; Pharmacology. Drug treatments; Prostate cancer; Prostatic Neoplasms - drug therapy; Testosterone; Testosterone - analogs & derivatives; Testosterone - chemical synthesis; Testosterone - chemistry; Testosterone - pharmacology; Testosterone; Dimers; Prostate cancer; Androgen receptor; Antineoplastic agent; Human; Stereoisomer; Cytotoxicity; In vitro; Biological activity; Cell line; Dimer; Chemical synthesis; Prostate; Tumor cell; Butene derivatives

The synthesis of two testosterone dimers is reported. The synthesis led to two separable isomeric dimers ( trans and cis, 2:1). X-ray diffraction crystallography confirmed the structure of the minor isomer. MTT assays showed that the cis dimer has the best activity against human prostate cancer cell...