title: Synthesis and selective anticancer activity of steroidal glycoconjugates.
abstract: The synthesis of glucosamine derivatives of the steroidal sapogenins diosgenin and hecogenin using the N-phthaloyl protected trichloroacetimidate of d-glucosamine as donor and TMSOTf as promoter is reported. The corresponding glycoconjugates were transformed into their acetamido derivatives and the hydrochloride salt (from diosgenin) and tested against HeLa, CaSki, and ViBo cervicouterine cancer cells. These compounds showed low cytotoxicity values on tumor cells and human lymphocytes, indicating that the main cell death process is presumably not necrosis. Significantly, the antiproliferative activity of these compounds on tumor cells did not affect the proliferative potential of peripheral blood lymphocytes.
authors: Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, British Columbia, Canada V5A 1S6.
authors: María A
authors: MA
authors: Fernández-Herrera
authors: Hugo
authors: H
authors: López-Muñoz
authors: José M V
authors: JM
authors: Hernández-Vázquez
authors: Luis
authors: L
authors: Sánchez-Sánchez
authors: María L
authors: ML
authors: Escobar-Sánchez
authors: B Mario
authors: BM
authors: Pinto
authors: Jesús
authors: J
authors: Sandoval-Ramírez
mesh_terms: D000117:Acetylglucosamine / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000737:chemistry / Q000145:classification* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation; D060326:Chemistry Techniques, Synthetic; D004144:Diosgenin / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006027:Glycosides / Q000737:chemistry; D006801:Humans; D012502:Sapogenins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D006027:Glycosides; D012502:Sapogenins; C007908:hecogenin; D004144:Diosgenin; D000117:Acetylglucosamine