Spectroscopic studies of DNA binding modes of cation-substituted anthrapyrazoles derived from emodin

Jia Heng Tan, Yu jing Lu, Zhi Shu Huang, Lian Quan Gu, Jianyong Wu

Research output: Journal article publicationJournal articleAcademic researchpeer-review

58 Citations (Scopus)

Abstract

The DNA binding properties of three cation-substituted anthrapyrazole derivatives of emodin with calf thymus DNA were characterized by spectroscopic methods and the specific binding modes were elucidated. At low drug and high DNA concentrations, compound 1 with a mono-cationic amino side chain exhibited an intercalative binding mode, 2 with a much longer and more flexible di-cationic side chain exhibited an external binding mode, and 3 with a rigid di-cationic side chain exhibited both intercalative and external binding modes. The DNA binding mode of compounds was altered after structural modification. The molecular structure-DNA binding relationships found from this study may be useful for the design of anthrapyrazole derivatives with desired binding characteristics.
Original languageEnglish
Pages (from-to)1169-1175
Number of pages7
JournalEuropean Journal of Medicinal Chemistry
Volume42
Issue number9
DOIs
Publication statusPublished - 1 Sep 2007

Keywords

  • Amino side chain
  • Anthrapyrazole
  • DNA binding
  • Emodin
  • Spectroscopic analysis

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

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