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- Title
Photo-induced electron transfer of [C<sub>60</sub> + Abacavir] nano-complex and feasibility of C<sub>60</sub> fullerene application as a chemical shift reagent: a DFT/TD-DFT insights.
- Authors
Emadoddin, Motahhare; Taherpour, Avat Arman; Jamshidi, Morteza
- Abstract
Due to its unique hybridization, derivatization ease, and significant properties, fullerene C60 has been extensively utilized as a drug delivery carrier and antiviral agent. Abacavir is an essential medicine used for the prevention and treatment of acquired immunodeficiency syndrome (AIDS). In the present study, the [C60 + Abacavir] nano-complex properties have been scrutinized in both ground and excited states applying density functional theory (DFT) and time-dependent density functional theory (TD-DFT). An investigation of the data by using the density of states, electron localization function, natural bond orbital, reduced density gradient, charge decomposition analysis, and the electrostatic potential map, revealed that the type of the intermolecular interaction between abacavir and C60 is Van der Waals force. This type of interaction would be useful in the release of abacavir into the target tissue. Also, the changes in the electron configuration before and after the complexation have been studied. The umpolung phenomenon index of the complex is equaled to 0.5 by calculating the partial accumulated Mulliken charges of the atoms involved. The complex dipole moment value of 1.07D proposes that the [C60 + Abacavir] complex may be soluble in polar solvents, such as physiological media, contrary to the pure fullerene. Therefore, it can transfer through blood. The ability of fullerene to cross, penetrate, and localize in hydrophobic domains makes it useful for drug delivery to lipid-rich regions. Besides, the complexation of abacavir with fullerene C60 would make abacavir more reactive in phosphorylation reaction for inhibiting HIV protease. Based on the results, the use of fullerene C60 nano-carrier can improve the efficacy of abacavir. Photo-electron transfer also has been investigated according to electron–hole and Marcus theories. The charge transfer process between two components may cause quenching fluorescence emission. Subsequently, tracing and detecting the nano-complex will be possible during the drug delivery. These electron transfer processes can bring about by applying external potentials. The results show that the H-atoms in the anisotropic field of fullerene have significantly changed in the chemical shifts. Therefore, fullerene C60 can be proposed as an organic chemical shift reagent in some NMR studies.
- Subjects
FULLERENES; CHEMICAL reagents; CHARGE exchange; ABACAVIR; AIDS; TIME-dependent density functional theory; CHEMICAL shift (Nuclear magnetic resonance)
- Publication
Journal of the Iranian Chemical Society, 2022, Vol 19, Issue 3, p937
- ISSN
1735-207X
- Publication type
Article
- DOI
10.1007/s13738-021-02360-3