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A DFT/TD-DFT study of [Amprenavir + C60] PET nanocomplex: feasibility of C60 fullerene application as a nanocarrier

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Abstract

The HIV (human immunodeficiency virus) attacks the immune system that, if not treated, causes AIDS. It also penetrates the central nervous system and causes HIV-related neurological disorders (HAND). In this study, fullerene C60 is proposed as a nanocarrier for Amprenavir (Amp), an anti-HIV drug. Also, some physicochemical properties of [Amp + C60] nanocomplex and its components have been theoretically investigated. The dipole moment of two components in the discussed complex (7.292 D) predicts that it will be soluble in polar solvents like water. Therefore, the process of drug delivery through the polar media will be feasible. Investigation of the formation energy and reduced density gradient of the discussed complex confirm that its components interact via weak interactions like Van der Waals forces. Thus, the release of the drug into the target tissue can be easily practical. It assumes no damage to Amp will occur. Fullerene, with unique properties as a highly delocalized conjugated π system, has shown high antioxidant capacity. The density of states and charge decomposition analysis revealed significant contribution of fullerene in the discussed complex orbitals. Amp will be preserved against adverse reactions during drug delivery due to the frontier complex orbitals that they are located on the fullerene part. Anti-HIV drugs like Amp are not able to cross the blood–brain barrier (BBB) and prevent HAND. Fullerene C60 may allow Amp to be transported across the BBB due to its small size and hydrophobicity. Examination of the Mulliken charge changes of the involved atoms, electron localization function , natural bond orbital , and electrostatic potential analyses indicate that the application of fullerene will improve the interaction of Amp with the virus protease. The photo-induced electron transfer studies have demonstrated that some electron transfer processes occurred in the discussed complex from Amp to fullerene C60 part. This feature can be utilized for monitoring and detecting the drug during the drug delivery process.

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Acknowledgements

We have acknowledged the Theoretical and Computational Research Center of Chemistry Faculty of the Razi University of Kermanshah, Iran.

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  1. Chemistry Department, Faculty of Chemistry, Razi University, P.O. Box: 67149-67346, Kermanshah, Iran

    Motahhare Emadoddin & Avat Arman Taherpour

  2. Young Researchers and Elite Club, Kermanshah Branch of Islamic Azad University, Kermanshah, Iran

    Morteza Jamshidi

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Emadoddin, M., Taherpour, A.A. & Jamshidi, M. A DFT/TD-DFT study of [Amprenavir + C60] PET nanocomplex: feasibility of C60 fullerene application as a nanocarrier. J IRAN CHEM SOC 19, 4169–4186 (2022). https://doi.org/10.1007/s13738-022-02592-x

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