title: One step synthesis of 6-oxo-cholestan-3β,5α-diol.
abstract: Cholesterol metabolism has been recently linked to cancer, highlighting the importance of the characterization of new metabolic pathways in the sterol series. One of these pathways is centered on cholesterol-5,6-epoxides (5,6-ECs). 5,6-ECs can either generate dendrogenin A, a tumor suppressor present in healthy mammalian tissues, or the carcinogenic cholestane-3β,5α,6β-triol (CT) and its putative metabolite 6-oxo-cholestan-3β,5α-diol (OCDO) in tumor cells. We are currently investigating the identification of the enzyme involved in OCDO biosynthesis, which would be highly facilitated by the use of commercially unavailable [(14)C]-cholestane-3β,5α,6β-triol and [(14)C]-6-oxo-cholestan-3β,5α-diol. In the present study we report the one-step synthesis of [(14)C]-cholestane-3β,5α,6β-triol and [(14)C]-6-oxo-cholestan-3β,5α-diol by oxidation of [(14)C]-cholesterol with iodide metaperiodate (HIO4).
authors: INSERM UMR 1037, Centre de Recherche en Cancérologie de Toulouse, Toulouse, France; Université de Toulouse III, Toulouse, France; Institut Claudius Regaud, Toulouse, France.
authors: Maud
authors: M
authors: Voisin
authors: INSERM UMR 1037, Centre de Recherche en Cancérologie de Toulouse, Toulouse, France; Université de Toulouse III, Toulouse, France; Institut Claudius Regaud, Toulouse, France.
authors: Sandrine
authors: S
authors: Silvente-Poirot
authors: INSERM UMR 1037, Centre de Recherche en Cancérologie de Toulouse, Toulouse, France; Université de Toulouse III, Toulouse, France; Institut Claudius Regaud, Toulouse, France. Electronic address: marc.poirot@inserm.fr.
authors: Marc
authors: M
authors: Poirot
mesh_terms: D060326:Chemistry Techniques, Synthetic; D002784:Cholesterol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D010084:Oxidation-Reduction
chemical_list: C551154:cholestan-6-oxo-3,5-diol; D002784:Cholesterol
keywords: Cancer; Cholestanetriol; OCDO; Oxysterols; Radiolabelled