title: The identification of perillyl alcohol glycosides with improved antiproliferative activity.
abstract: A facile route to perillyl alcohol (POH) differential glycosylation and the corresponding synthesis of a set of 34 POH glycosides is reported. Subsequent in vitro studies revealed a sugar dependent antiproliferative activity and the inhibition of S6 ribosomal protein phosphorylation as a putative mechanism of representative POH glycosides. The most active glycoside from this cumulative study (4'-azido-d-glucoside, PG9) represents one of the most cytotoxic POH analogues reported to date.
authors.affiliation: Center for Pharmaceutical Research and Innovation, College of Pharmacy, University of Kentucky , 789 South Limestone Street, Lexington, Kentucky 40536-0596, United States.
authors.forename: Nitin S
authors.initials: NS
authors.lastname: Nandurkar
authors.forename: Jianjun
authors.initials: J
authors.lastname: Zhang
authors.forename: Qing
authors.initials: Q
authors.lastname: Ye
authors.forename: Larissa V
authors.initials: LV
authors.lastname: Ponomareva
authors.forename: Qing-Bai
authors.initials: QB
authors.lastname: She
authors.forename: Jon S
authors.initials: JS
authors.lastname: Thorson
mesh_terms: D048868:Adaptor Proteins, Signal Transducing / Q000378:metabolism; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015153:Blotting, Western; D018797:Cell Cycle Proteins; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects*; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D020128:Inhibitory Concentration 50; D008956:Models, Chemical; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry*; D010750:Phosphoproteins / Q000378:metabolism; D010766:Phosphorylation / Q000187:drug effects
chemical_list: D048868:Adaptor Proteins, Signal Transducing; D000970:Antineoplastic Agents; D018797:Cell Cycle Proteins; C087000:EIF4EBP1 protein, human; D006027:Glycosides; D039821:Monoterpenes; D010750:Phosphoproteins; C032208:perillyl alcohol