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A Density Functional Theory Study on the Interaction Between 5-Fluorouracil Drug and C24 Fullerene

Journal of Cluster Science volume 28, pages 2681–2692 (2017)Cite this article

Abstract

Penetration of most of the polar drugs through the cell membrane is a challenging problem. It has been indicated that carbonaceous nanostructures can penetrate into biological cells. Here, we investigated the potential application of a C24 fullerene as a carrier for anti-cancer 5-fluorouracil (5-FU) drug using density functional theory calculations. It was found that the 5-FU interaction with the pristine fullerene is very weak with adsorption energy of about −3.2 kcal/mol which is not suitable for drug delivery. To overcome this problem, one carbon atom is substituted by a boron atom which increases the adsorption energy to −27.2 kcal/mol. The B-doping makes the electronic properties of the fullerene sensitive to the drug. Finally, we proposed a drug release based on the low pH in the cancer cells. It was indicated that attacking protons to the interaction area between the drug and fullerene separates the drug from the carrier.

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Acknowledgements

The authors gratefully acknowledge the financial support of this work by the Mazandaran University of Medical Sciences “Professor’s Projects Funds”. Payame Noor University gratefully acknowledged for financial support.

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Authors and Affiliations

  1. Department of Engineering Science, College of Engineering, University of Tehran, P.O. Box 11365-4563, Tehran, Iran

    Akram Hosseinian

  2. Department of Chemistry, Payame Noor University, Tehran, Iran

    Esmail Vessally

  3. Department of Chemistry, Miyaneh Branch, Islamic Azad University, Miyaneh, Iran

    Saeideh Yahyaei

  4. Department of Chemistry, Tabriz Branch, Islamic Azad University, Tabriz, Iran

    Ladan Edjlali

  5. Pharmaceutical Sciences Research Center, Department of Medicinal Chemistry, Mazandaran University of Medical Sciences, Sari, Iran

    Ahmadreza Bekhradnia

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  1. Akram Hosseinian
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  2. Esmail Vessally
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  4. Ladan Edjlali
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  5. Ahmadreza Bekhradnia
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Correspondence to Esmail Vessally or Ahmadreza Bekhradnia.

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Hosseinian, A., Vessally, E., Yahyaei, S. et al. A Density Functional Theory Study on the Interaction Between 5-Fluorouracil Drug and C24 Fullerene. J Clust Sci 28, 2681–2692 (2017). https://doi.org/10.1007/s10876-017-1253-6

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  • DOI: https://doi.org/10.1007/s10876-017-1253-6

Keywords

  • Electronic structure
  • Nanostructure
  • Drug delivery
  • DFT