title: Synthesis of a resveratrol analogue with high ceramide-mediated proapoptotic activity on human breast cancer cells.
abstract: Resveratrol, a natural product with a stilbene structure, exerts profound proapoptotic activity in human cancer cells, by triggering the accumulation of ceramide, a bioactive sphingolipid. We studied the biological effects of seven methoxylated and/or naphthalene-based resveratrol analogues and compared these compounds with resveratrol with the objective to identify an analogue with higher ceramide-mediated proapoptotic activity relative to resveratrol. Here we show that the compound with three hydroxyls and a naphthalene ring is the most effective in triggering apoptosis coupled to the induction of endogenous ceramide in human cancer cells.
authors.affiliation: Department of Pharmaceutical Sciences, University of Pisa, via Bonanno 6, 56126 Pisa, Italy.
authors.forename: Filippo
authors.initials: F
authors.lastname: Minutolo
authors.forename: Giusy
authors.initials: G
authors.lastname: Sala
authors.forename: Annalisa
authors.initials: A
authors.lastname: Bagnacani
authors.forename: Simone
authors.initials: S
authors.lastname: Bertini
authors.forename: Isabella
authors.initials: I
authors.lastname: Carboni
authors.forename: Giorgio
authors.initials: G
authors.lastname: Placanica
authors.forename: Giovanni
authors.initials: G
authors.lastname: Prota
authors.forename: Simona
authors.initials: S
authors.lastname: Rapposelli
authors.forename: Nicoletta
authors.initials: N
authors.lastname: Sacchi
authors.forename: Marco
authors.initials: M
authors.lastname: Macchia
authors.forename: Riccardo
authors.initials: R
authors.lastname: Ghidoni
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D017209:Apoptosis; D001943:Breast Neoplasms; D045744:Cell Line, Tumor; D002518:Ceramides / Q000096:biosynthesis*; D004354:Drug Screening Assays, Antitumor; D005260:Female; D006801:Humans; D000077185:Resveratrol; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D002518:Ceramides; D013267:Stilbenes; D000077185:Resveratrol