Total synthesis and biological evaluation of largazole and derivatives with promising selectivity for cancers cells

Xin Zeng, Biaolin Yin, Zheng Hu, Chenzhong Liao, Jinglei Liu, Shang Li, Zheng Li, Marc C. Nicklaus, Guangbiao Zhou, Sheng Jiang

Research output: Contribution to journalArticle

76 Scopus citations

Abstract

"Chemical Equation Presented" The efficient total synthesis of the natural substance largazole is described. Using this strategy, a small library of largazole analogs was developed. Structure-activity relationship studies suggested that the geometry of the alkene in the side chain is critical. While the largazole's analogues with frans-alkene are potent for the antiproliferative effect, those with cis-alkene are completely Inactive. Most Importantly, replacement of valine with tyrosine in largazole increased selectivity toward human cancer cells over human normal cells more than 100-fold.

Original languageEnglish (US)
Pages (from-to)1368-1371
Number of pages4
JournalOrganic Letters
Volume12
Issue number6
DOIs
StatePublished - Mar 19 2010

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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