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Abstract

Steroids Conjugated to Carbon Nanoforms as Potential Inhibitors of Viral Proteases, Synthesis, DFT Calculations, and Molecular Docking †

1
Laboratorio de Síntesis Orgánica, Facultad de Química, Universidad de la Habana, La Habana 10400, Cuba
2
Departament of Surfactants and Nanobiotechnology, Institute for Advanced Chemistry of Catalonia (IQAC-CSIC), 08034 Barcelona, Spain
*
Author to whom correspondence should be addressed.
Presented at the 8th International Electronic Conference on Medicinal Chemistry, 1–30 November 2022; Available online: https://ecmc2022.sciforum.net/.
Med. Sci. Forum 2022, 14(1), 53; https://doi.org/10.3390/ECMC2022-13243
Published: 1 November 2022
(This article belongs to the Proceedings of The 8th International Electronic Conference on Medicinal Chemistry)

Abstract

:
Steroid [60]fullerene hybrids have been synthesized by the Bingel−Hirsch reaction as a contribution to the chemistry of carbon nanoforms. The hybrids were characterized by different spectroscopic experiments and analytical techniques. Theoretical calculations using the Density functional theory and the PBE functional were performed to predict the most stable conformations for the synthesized compounds and the frontier molecular orbitals energy. Some properties, such as polarizability, dipole moment, lipophilicity, solvent-accessible surface area, and topological polar surface area, were calculated. Fullerenes and their derivatives have potential antiviral activity due to their specific binding interactions with biological molecules. The ability of fullerene derivatives to interact with the active site of HIV and SARS-Cov-2 proteases was studied by the Autodock Vina program. The C60 cage exhibited an interaction with the phenyl group of phenylalanine residues through π–π and T-shape interactions. Furthermore, it was observed that the steroid moieties formed H-bonds with the amino acid residues in the active sites of proteins. In addition, van der Waals contacts with the nonpolar protease surface, thereby improving the binding relative to the tested compound. Protein-ligand docking revealed several important molecular fragments that are responsible for the interaction, thus paving the way to study the possible application of these hybrids in medicinal chemistry.

Supplementary Materials

The following are available online at https://www.mdpi.com/article/10.3390/ECMC2022-13243/s1.

Author Contributions

Conceptualization, R.L., M.S. and K.M.; methodology, R.L. and K.M.; validation, R.L. and K.M.; formal analysis, R.L., K.M. and M.S.; investigation, R.L., K.M. and M.S.; data curation, R.L., K.M. and M.S.; writing—original draft preparation, R.L. and M.S.; writing—review and editing, R.L. and M.S.; supervision, M.S. All authors have read and agreed to the published version of the manuscript.

Funding

This research was funded by PNCB of MES, Cuba (P223LH-001-059).

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

Not applicable.

Conflicts of Interest

The authors declare no conflict of interest.
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations.

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MDPI and ACS Style

Lemos, R.; Makowski, K.; Suárez, M. Steroids Conjugated to Carbon Nanoforms as Potential Inhibitors of Viral Proteases, Synthesis, DFT Calculations, and Molecular Docking. Med. Sci. Forum 2022, 14, 53. https://doi.org/10.3390/ECMC2022-13243

AMA Style

Lemos R, Makowski K, Suárez M. Steroids Conjugated to Carbon Nanoforms as Potential Inhibitors of Viral Proteases, Synthesis, DFT Calculations, and Molecular Docking. Medical Sciences Forum. 2022; 14(1):53. https://doi.org/10.3390/ECMC2022-13243

Chicago/Turabian Style

Lemos, Reinier, Kamil Makowski, and Margarita Suárez. 2022. "Steroids Conjugated to Carbon Nanoforms as Potential Inhibitors of Viral Proteases, Synthesis, DFT Calculations, and Molecular Docking" Medical Sciences Forum 14, no. 1: 53. https://doi.org/10.3390/ECMC2022-13243

APA Style

Lemos, R., Makowski, K., & Suárez, M. (2022). Steroids Conjugated to Carbon Nanoforms as Potential Inhibitors of Viral Proteases, Synthesis, DFT Calculations, and Molecular Docking. Medical Sciences Forum, 14(1), 53. https://doi.org/10.3390/ECMC2022-13243

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