Synthesis of linked berberine dimers and their remarkably enhanced DNA-binding affinities

Wen Hua Chen*, Ji Yan Pang, Yong Qin, Qian Peng, Zongwei CAI, Zhi Hong JIANG

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

56 Citations (Scopus)

Abstract

This communication describes the facile synthesis of five novel berberine dimers and their strong affinities toward double-stranded DNA. These berberine dimers were synthesized in 37-84% yields from the reaction of berberrubine with dihaloalkanes of varying lengths, and fully characterized by HRMS and 1H NMR. Compared with the monomeric parent berberine, these dimers showed greatly enhanced binding affinities up to approximately 100-fold, with two double helical oligodeoxynucleotides, d(AAGAATTCTT)2 and d(TAAGAATTCTTA)2, which was investigated by means of fluorescence spectrometry.

Original languageEnglish
Pages (from-to)2689-2692
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume15
Issue number10
DOIs
Publication statusPublished - 16 May 2005

Scopus Subject Areas

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

User-Defined Keywords

  • Berberine dimer
  • DNA
  • Fluorescence spectrometry
  • Noncovalent interaction

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