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

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.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide