title: Synthesis and antiproliferative activity of selenoindirubins and selenoindirubin-N-glycosides.
abstract: Selenoindirubins and selenoindirubin-N-glycosides were prepared by the reaction of isatins and isatin-N-glycosides with 3-acetoxy-benzo[b]selenophene, respectively. While selenoindirubin-N-glycosides have not been reported before, three non-glycosylated selenoindirubins were previously reported, but without quantities, yields, scales, experimental details and spectroscopic data. In addition, the work could, in our hands, not be reproduced to prepare pure products. The present paper includes an optimized procedure for the synthesis of selenoindirubins and their complete characterization. Both selenoindirubins and selenoindirubin-N-glycosides showed antiproliferative activity in lung cancer cell lines. In melanoma cells, antiproliferative effects were further accompanied by induced apoptosis in combination with the death ligand TRAIL.
authors.affiliation: Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany.
authors.forename: Friedrich
authors.initials: F
authors.lastname: Erben
authors.forename: Dennis
authors.initials: D
authors.lastname: Kleeblatt
authors.forename: Marcel
authors.initials: M
authors.lastname: Sonneck
authors.forename: Martin
authors.initials: M
authors.lastname: Hein
authors.forename: Holger
authors.initials: H
authors.lastname: Feist
authors.forename: Thomas
authors.initials: T
authors.lastname: Fahrenwaldt
authors.forename: Christine
authors.initials: C
authors.lastname: Fischer
authors.forename: Abdul
authors.initials: A
authors.lastname: Matin
authors.forename: Jamshed
authors.initials: J
authors.lastname: Iqbal
authors.forename: Michael
authors.initials: M
authors.lastname: Plötz
authors.forename: Jürgen
authors.initials: J
authors.lastname: Eberle
authors.forename: Peter
authors.initials: P
authors.lastname: Langer
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
chemical_list: D000970:Antineoplastic Agents; D006027:Glycosides; D007211:Indoles; D016566:Organoselenium Compounds