Quantum chemical simulation of epirubicin interaction with fullerene and carbon graphene-like plane
Abstract
Creation of new “targeted delivery” drugs is one of priority areas of pharmacology and is especially true for oncology. Medicinal substances, in particular those of anthracycline series, immobilized on the surface of nanosized carriers for the targeted delivery of drugs to target organs or target tissues, allow creating an optimal concentration of the drug in the area of therapeutic effect. The latter significantly reduces systemic toxicity by decreasing the total dose and longer retention in the lesion, as well as increasing the solubility and bioavailability of drugs. Ones of promising drug delivery nanosystems are carbon materials, in particular, fullerene (C60) and pristine or modified graphene. The feature of carbon systems, in contrast to organic and dielectric transport systems, is their high conductivity and the dependence of the interaction energy between atoms of transporters and drugs on their charge state. To date, the specifics of the interaction of epirubicin with a graphene-like plane (GP) and fullerene at the atomic level remain poorly understood. Therefore, the energy parameters of the interaction of GP and C60 with epirubicin in various protolytic forms, which reveal at different pH values of the aqueous medium, were studied using quantum chemistry methods. Calculations were carried out using the MOPAC2016 program and the PM6-D3H4X method, in which, along with hydrogen bonds, the dispersion interactions are taken into account. Based on the analysis of the results of quantum chemical studies, the thermodynamic probability of the epirubicin adsorption process on GP is predicted in the entire pH range of the aqueous medium, as evidenced by the negative values of interaction enthalpies in all four cases. It has been found that epirubicin (protonated form) will have the greatest adsorption both on the graphene plane (−209.1 kJ/mol) and upon interaction with the fullerene molecule (−121.3 kJ/mol).
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