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Synthesis and Characterization of Citrusinol Acetyl Derivative, and Its Interactions with DNA and BSA: 13C NMR, 1H NMR, HMBC, Fluorescence, UV–Vis spectrum, and Molecular Docking

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Abstract

Citrusinol was regarded as an antineoplastic agent, and acetyl-citrusinol was synthesized as a new derivative of citrusinol. The interactions of bovine serum albumin (BSA) and calf thymus DNA (ct-DNA) with citrusinol and acetyl-citrusinol were studied. The structure of acetyl-citrusinol was identified by nuclear magnetic resonance (13C NMR, 1H NMR) and heteronuclear multiple-bond correlation (HMBC). Fluorescence spectrum and molecular docking were used to investigate the interactions of citrusinol and acetyl-citrusinol with BSA. The UV–Vis spectroscopy was used to study the interactions of citrusinol and acetyl-citrusinol with ct-DNA. The citrusinol and acetyl-citrusinol combining with BSA showed the fluorescence quenching and a decrease in the maximum emission wavelength. The molecular docking results showed that there were stable combinations of citrusinol and acetyl-citrusinol with BSA. Thus, the interactions between citrusinol and acetyl-citrusinol with BSA were mainly hydrophobic and hydrogen bonding. According to the UV–Vis spectrum, citrusinol, and acetyl-citrusinol interacted with ct-DNA via electrostatic interaction.

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ACKNOWLEDGMENTS

This work was supported by the Natural Science Foundation of Guangxi Province (2017GXNSFBA198214, 2019GXNSFAA245081).

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Authors and Affiliations

  1. Department of Chemistry of Chinese Materia Medica, Guangxi Institute of Traditional Medical and Pharmaceutical Sciences, Nanning, P.R. China

    Z. F. Huang, X. X. Hu, G. S. Lu, J. Y. Huang & X. Tan

  2. Guangxi Key Laboratory of Traditional Chinese Medicine Quality Standards, Nanning, P.R. China

    Z. F. Huang

  3. Pharmaceutical College, Guangxi Medical University, Nanning, P.R. China

    Y. Ye

  4. State Key Laboratory of Biotherapy, Sichuan University, Chengdu, P.R. China

    L. H. He

  5. Reproductive Medicine Center, Maternal and Child Health Hospital of Guangxi Zhuang Autonomous Region, Nanning, P.R. China

    L. H. He & G. T. Huang

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  1. Z. F. Huang
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  2. X. X. Hu
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  3. G. S. Lu
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  4. J. Y. Huang
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Correspondence to Z. F. Huang, X. X. Hu or G. S. Lu.

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Huang, Z.F., Hu, X.X., Lu, G.S. et al. Synthesis and Characterization of Citrusinol Acetyl Derivative, and Its Interactions with DNA and BSA: 13C NMR, 1H NMR, HMBC, Fluorescence, UV–Vis spectrum, and Molecular Docking. Russ. J. Phys. Chem. 95, 1394–1401 (2021). https://doi.org/10.1134/S0036024421070128

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  • DOI: https://doi.org/10.1134/S0036024421070128

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