Interaction of 3′-azido-3′-deamino daunorubicin with DNA: Multispectroscopic and molecular modeling

In this paper, 3′-azido-3′-deamino daunorubicin (ADNR) was synthesized and the interaction of ADNR and calf thymus DNA (ctDNA) was investigated for the first time by using multi-spectroscopic techniques and molecular modeling study in vitro under simulated physiological conditions. Hypochromicity of the absorption spectra of ADNR were observed in the presence of ctDNA, and the fluorescence of ADNR was strongly quenched through static mechanism with the addition of ctDNA. Moreover, the fluorescence polarization was increased when ctDNA was added. From the experimental results, conclusion can be drawn that the binding mode of ADNR with ctDNA was an intercalative binding, and the calculated thermodynamic parameters suggested that the binding of ADNR to ctDNA was driven mainly by hydrogen bonding force. Furthermore, the results obtained from computational modeling further proved the experimental results obtained from spectroscopic investigations.