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Spectroscopic and molecular modeling studies on the interactions of some benzofuran derivatives with BSA

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Abstract

In this study, the interactions of a series of benzofuran derivatives with bovine serum albumin (BSA) were investigated using UV–Vis and fluorescence spectroscopy and molecular modeling. The intrinsic fluorescence of BSA was found to be quenched by the benzofuran derivatives. The binding constants between the benzofuran derivatives and BSA calculated from fluorescence quenching were found to be (1.80 ± 0.04) × 104, (1.88 ± 0.06) × 104, and (2.02 ± 0.07) × 104 dm3 mol−1, respectively. According to the fluorescence resonance energy transfer, the average binding distances between the benzofuran derivatives and BSA were calculated to be 3.22, 3.29, and 3.02 nm, respectively. The binding of the benzofuran derivatives and BSA was modeled by molecular docking and molecular dynamic (MD) simulation methods. Principal component analysis was performed on 2001 snapshots of the MD trajectories at the equilibrium state. Based on the different regions in the PC space, about 15 conformations were selected, and the average of these was used to determine the interactions between the benzofuran derivatives and BSA. The results revealed that the benzofuran derivatives preferred the binding pocket of domain II of BSA.

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Acknowledgements

The authors would like to extend their thanks to the Research Council of Isfahan University of Technology and the Center of Excellence on Chemistry at Isfahan University of Technology. Sheikh Bahaei National High Performance Computing of Isfahan University of Technology also deserves our gratitude for performing the parallel simulation on RAKHSH cluster. We thank Reza Maleki for revising the manuscript. We are grateful to Dr. Anthea Downs for editing the final version of the manuscript.

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Authors and Affiliations

  1. Department of Chemistry, Isfahan University of Technology, Isfahan, 84156-83111, Iran

    Batool Maleki & Taghi Khayamian

  2. Faculty of Chemistry, University of Tehran, Tehran, Iran

    Jahan B. Ghasemi

  3. Department of Chemistry, Faculty of Science, University of Bu-Ali-Sina, Hamadan, 65174, Iran

    Davood Nematollahi

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  1. Batool Maleki
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  2. Taghi Khayamian
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  3. Jahan B. Ghasemi
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  4. Davood Nematollahi
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Correspondence to Jahan B. Ghasemi.

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Maleki, B., Khayamian, T., Ghasemi, J.B. et al. Spectroscopic and molecular modeling studies on the interactions of some benzofuran derivatives with BSA. Monatsh Chem 148, 1887–1896 (2017). https://doi.org/10.1007/s00706-017-1975-z

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  • DOI: https://doi.org/10.1007/s00706-017-1975-z

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