title: Synthesis of a new ent-cyclozonarone angular analog, and comparison of its cytotoxicity and apoptotic effects with ent-cyclozonarone.
abstract: The synthesis of a newangular analog 11 of cyclozonarone was achieved via Diels-Alder reaction between a sesquiterpene-1,3-diene and 1,4-benzoquinone. The cytotoxic activity of ent-cyclozonarone [(+)-10] and the angular (-)-cyclozonarone analog 11 has been determined in three human cancer cell lines and in normal fibroblasts using the sulforhodamine B assay. The analyzed isomers induce cell death in different cancer cell lines by eliciting nuclear condensation and fragmentation, decreasing mitochondrial membrane permeability and increasing caspase-3 activity, all traits indicating apoptosis, with the effects of (+)-10 being stronger than those of 11 in all cases.
authors.affiliation: Facultad de Farmacia, Universidad de Valparaíso, Av. Gran Bretaña N° 1093, Valparaíso, Chile.
authors.forename: Natalia Quiñones
authors.initials: NQ
authors.lastname: Sobarzo
authors.forename: Iván Montenegro
authors.initials: IM
authors.lastname: Venegas
authors.forename: Cristian Salas
authors.initials: CS
authors.lastname: Sánchez
authors.forename: Luis Espinoza
authors.initials: LE
authors.lastname: Catalán
authors.forename: Cristóbal Carrasco
authors.initials: CC
authors.lastname: Rojas
authors.forename: Valentina Ulloa
authors.initials: VU
authors.lastname: Valdivia
authors.forename: Joan Villena
authors.initials: JV
authors.lastname: García
authors.forename: Mauricio Cuellar
authors.initials: MC
authors.lastname: Fritis
mesh_terms: D017209:Apoptosis / Q000187:drug effects*; D053148:Caspase 3 / Q000378:metabolism; D045744:Cell Line, Tumor; D002467:Cell Nucleus / Q000378:metabolism* / Q000473:pathology; D003603:Cytotoxins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005347:Fibroblasts / Q000378:metabolism* / Q000473:pathology; D006801:Humans; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: D003603:Cytotoxins; D012717:Sesquiterpenes; C429221:cyclozonarone; C505407:CASP3 protein, human; D053148:Caspase 3