DNA-binding affinities and sequence specificities of protoberberine alkaloids and their demethylated derivatives: A comparative study

Yong Qin, Wen Hua Chen, Ji Yan Pang, Zhongzhen ZHAO, Liang LIU, Zhi Hong JIANG*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

Berberrubine (1a), jatrorubine (2a), and palmatrubine (3a) have been chemically prepared by partial demethylation of berberine (1), jatrorrhizine (2), and palmatine (3), respectively. Their interactions with calf thymus (CT) DNA, poly(dA-dT) · poly(dA-dT), poly(dG-dC) · poly(dG-dC), and eight AT-rich 12-mer double-stranded DNAs have been investigated by means of competitive ethidium bromide (EB) displacement experiments. The results showed that DNA-binding affinities of these protoberberine alkaloids have been significantly improved by partial demethylation, and that all of these alkaloids have the preferable binding affinities with AT-rich DNA. Especially, the sequence specificities of DNA-binding of demethylated derivatives 1a, 2a, and 3a had changed to a certain extent when compared with the parent alkaloids 1, 2, and 3, respectively. The binding mode of these alkaloids was further confirmed by UV spectroscopic titration experiments. All the compounds bind to double-stranded DNA most probably via an intercalating mode.

Original languageEnglish
Pages (from-to)145-153
Number of pages9
JournalChemistry and Biodiversity
Volume4
Issue number2
DOIs
Publication statusPublished - 2007

Scopus Subject Areas

  • Bioengineering
  • Biochemistry
  • Chemistry(all)
  • Molecular Medicine
  • Molecular Biology

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