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An Androsterone-H2@C60 hybrid: Synthesis, Properties and Molecular Docking Simulations with SARS-Cov-2

Abstract:

We report the synthesis and characterization of a fullerene-steroid hybrid that contains H<inf>2</inf>@C<inf>60</inf> and a dehydroepiandrosterone moiety synthesized by a cyclopropanation reaction with 76 % yield. Theoretical calculations at the DFT-D3(BJ)/PBE 6-311G(d,p) level predict the most stable conformation and that the saturation of a double bond is the main factor causing the upfield shielding of the signal appearing at −3.13 ppm, which corresponds to the H<inf>2</inf> located inside the fullerene cage. Relevant stereoelectronic parameters were also investigated and reinforce the idea that electronic interactions must be considered to develop studies on chemical-biological interactions. A molecular docking simulation predicted that the binding energy values for the protease-hybrid complexes were −9.9 kcal/mol and −13.5 kcal/mol for PL<sup>pro</sup> and 3CL<sup>pro</sup> respectively, indicating the potential use of the synthesized steroid-H<inf>2</inf>@C<inf>60</inf> as anti-SARS-Cov-2 agent.