Synthesis and human telomeric G-quadruplex DNA-binding activity of glucosaminosides of shikonin/alkannin

Hao He, Li Ping Bai, Zhi Hong JIANG*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

The N-acetyl glucosaminosides of shikonin/alkannin were synthesized by chemical glycosylation, which provided an ideal approach to resolve the mixture of enantiomeric shikonin and alkannin co-existed in the Chinese herbs. The glycosylated shikonin and alkannin exhibited stronger binding activity to human telomeric G-quadruplex DNA than their parent structures. This research indicated that glycosylation of natural product with amino sugars is an effective strategy to improve their DNA-binding affinity.

Original languageEnglish
Pages (from-to)1582-1586
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume22
Issue number4
DOIs
Publication statusPublished - 15 Feb 2012

Scopus Subject Areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

User-Defined Keywords

  • Alkannin
  • G-quadruplex
  • Glycosylation
  • Shikonin
  • Telomeric

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