The identification of perillyl alcohol glycosides with improved antiproliferative activity

  • J Med Chem. 2014 Sep 11;57(17):7478-84. doi: 10.1021/jm500870u.
Nitin S Nandurkar  1 ,  Jianjun Zhang ,  Qing Ye ,  Larissa V Ponomareva ,  Qing-Bai She ,  Jon S Thorson
Affiliations
  • 1. Center for Pharmaceutical Research and Innovation, College of Pharmacy, University of Kentucky , 789 South Limestone Street, Lexington, Kentucky 40536-0596, United States.
PMID: 25121720 DOI: 10.1021/jm500870u
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.