Spacer length and attaching position-dependent binding of synthesized protoberberine dimers to double-stranded DNA

Yu Hua Long, Li Ping Bai, Yong Qin, Ji Yan Pang, Wen Hua Chen*, Zongwei CAI, Zun Le Xu, Zhi Hong JIANG

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

Six jatrorrhizine homodimers and berberine-jatrorrhizine heterodimers have been synthesized in moderate to good yields from the reaction of jatrorrhizine with α,ω-dibromoalkanes and 9-O-(ω-bromoalkyl)berberines, respectively. Their binding activities toward calf thymus (CT) DNA and three double-stranded oligodeoxynucleotides, d(AAGAATTCTT)2, d(TAAGAATTCTTA)2, and d(TTAAGAATTCTTAA)2, were investigated by means of spectrofluorimetric and spectrophotometric titrations. The results indicate that these dimers exhibit enhanced DNA-binding affinities due to the cooperative interaction of the two protoberberine subunits. A comparative study of the DNA-binding behaviors of berberine homodimers, jatrorrhizine homodimers, and berberine-jatrorrhizine heterodimers suggests that spacer length and attaching position are of great importance in modulating their DNA-binding affinities.

Original languageEnglish
Pages (from-to)4670-4676
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume14
Issue number13
DOIs
Publication statusPublished - 1 Jul 2006

Scopus Subject Areas

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

User-Defined Keywords

  • Dimerization
  • DNA binding
  • Jatrorrhizine
  • Protoberberine
  • Synthesis

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