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Study on the Interaction of an Anthracycline Disaccharide with DNA by Spectroscopic Techniques and Molecular Modeling

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Abstract

This study was designed to examine the interaction of 4′-O-(a-L-Cladinosyl) daunorubicin (DNR–D5), a disaccharide anthracycline with calf thymus deoxyribonucleic acid (ctDNA) by UV/Vis in combination with fluorescence spectroscopy and molecular modeling techniques under physiological conditions (Britton–Robinson buffer solutions, pH = 7.4). By the analysis of UV/Vis spectrum, it was observed that upon binding to ctDNA the anthraquinone chromophore of DNR–D5 could slide into the base pairs. Moreover, the large binding constant indicated DNR–D5 had a high affinity with ctDNA. At the same time, fluorescence spectra suggested that the quenching mechanism of the interaction of DNR–D5 to ctDNA was a static quenching type. The binding constants between DNR–D5 and ctDNA were calculated based on fluorescence quenching data at different temperatures. The negative ∆G implied that the binding process was spontaneous, and negative ∆H and negative ΔS suggested that hydrogen bonding force most likely played a major role in the binding of DNR–D5 to ctDNA. Moreover, the results obtained from molecular docking corroborate the experimental results obtained from spectroscopic investigations.

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Acknowledgements

The authors are grateful to the National Natural Science Foundation of China (Grant no. 20673034 and 20672031), the Research Fund for the Doctoral Program of Higher Education of China (Grant no. 20060476001) and the program for Innovative Research Team in University of Henan Province (2008IRTSTHN002) for their financial supports.

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  1. School of Chemistry and Environmental Science, Henan Normal University, 46 Jian-she Road, Mu Ye District, Xinxiang, 453007, China

    Yan Lu, Gong-Ke Wang, Juan Lv, Gui-Sheng Zhang & Qing-Feng Liu

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  1. Yan Lu
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  2. Gong-Ke Wang
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Correspondence to Yan Lu.

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Lu, Y., Wang, GK., Lv, J. et al. Study on the Interaction of an Anthracycline Disaccharide with DNA by Spectroscopic Techniques and Molecular Modeling. J Fluoresc 21, 409–414 (2011). https://doi.org/10.1007/s10895-010-0729-7

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  • DOI: https://doi.org/10.1007/s10895-010-0729-7

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