Influence of Sugar Amine Regiochemistry on Digitoxigenin Neoglycoside Anticancer Activity

Jianjun Zhang, Larissa V. Ponomareva, Nitin S. Nandurkar, Yaxia Yuan, Lei Fang, Chang Guo Zhan, Jon S. Thorson

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

The synthesis of a set of digitoxigenin neogluco/xylosides and corresponding study of their anticancer SAR revealed sugar amine regiochemistry has a dramatic effect upon activity. Specifically, this study noted sugar 3-amino followed by 4-amino-substitution to be most advantageous where the solvent accessibility of the appended amine within neoglycoside-Na+,K+-ATPase docked models correlated with increased anticancer potency. This study presents a preliminary model for potential further warhead optimization in the context of antibody-directed steroidal glycosides and extends the demonstrated compatibility of aminosugars in the context of neoglycosylation.

Original languageEnglish (US)
Pages (from-to)1053-1058
Number of pages6
JournalACS Medicinal Chemistry Letters
Volume6
Issue number10
DOIs
StatePublished - Oct 8 2015
Externally publishedYes

Keywords

  • digitoxigenin
  • neoglycosylation
  • Regiochemistry
  • sugar

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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