title: Synthesis and biological evaluation of the glycoside (25R)-3β,16β-diacetoxy-22-oxocholest-5-en-26-yl β-d-glucopyranoside: a selective anticancer agent in cervicouterine cell lines.
abstract: The synthesis and biological evaluation of the new cholestane glycoside (25R)-3β,16β-diacetoxy-22-oxocholest-5-en-26-yl β-d-glucopyranoside starting from diosgenin is described. This compound showed selective antiproliferative activity against CaSki, ViBo, and HeLa cervicouterine cancer cells. Its effect on the cell-cycle was determined. The cytotoxic effects of the title compound on cervicouterine cancer cell lines and human lymphocytes indicate that the main cell death process is not necrosis; hence it is not cytotoxic. The title compound induced apoptosis in cervicouterine cancer cells. Importantly, the antiproliferative activity on tumor cells did not affect the proliferative potential of peripheral blood lymphocytes. The title compound showed selective antitumor activity and greater antiproliferative activity than its aglycon, and therefore serves as a promising lead candidate for further optimization.
authors.affiliation: Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla. Ciudad Universitaria, 72570 Puebla, Pue, México.
authors.forename: María A
authors.initials: MA
authors.lastname: Fernández-Herrera
authors.forename: Hugo
authors.initials: H
authors.lastname: López-Muñoz
authors.forename: José M V
authors.initials: JM
authors.lastname: Hernández-Vázquez
authors.forename: Moisés
authors.initials: M
authors.lastname: López-Dávila
authors.forename: Sankar
authors.initials: S
authors.lastname: Mohan
authors.forename: María L
authors.initials: ML
authors.lastname: Escobar-Sánchez
authors.forename: Luis
authors.initials: L
authors.lastname: Sánchez-Sánchez
authors.forename: B Mario
authors.initials: BM
authors.lastname: Pinto
authors.forename: Jesús
authors.initials: J
authors.lastname: Sandoval-Ramírez
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D053148:Caspase 3 / Q000378:metabolism; D002453:Cell Cycle / Q000187:drug effects; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002784:Cholesterol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D053938:DNA Fragmentation; D005260:Female; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D008214:Lymphocytes / Q000166:cytology / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D002583:Uterine Cervical Neoplasms / Q000473:pathology
chemical_list: C568943:3,16-diacetoxy-22-oxocholest-5-en-26-yl glucopyranoside; D000970:Antineoplastic Agents; D005960:Glucosides; D002784:Cholesterol; D053148:Caspase 3