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Synthesis of [60]Fullerene Hybrids Endowed with Steroids and Monosaccharides: Theoretical Underpinning as Promising anti‐SARS‐CoV‐2 Agents
Cyclopropanation reactions between C(60) and different malonates decorated with monosaccharides and steroids using the Bingel‐Hirsch methodology have allowed the obtention of a new family of hybrid compounds in good yields. A complete set of instrumental techniques has allowed us to fully characteri...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9880710/ https://www.ncbi.nlm.nih.gov/pubmed/36721524 http://dx.doi.org/10.1002/ejoc.202201301 |
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author | Lemos, Reinier Makowski, Kamil Almagro, Luis Tolón, Blanca Rodríguez, Hortensia Herranz, M. Ángeles Molero, Dolores Martín, Nazario Suárez, Margarita |
author_facet | Lemos, Reinier Makowski, Kamil Almagro, Luis Tolón, Blanca Rodríguez, Hortensia Herranz, M. Ángeles Molero, Dolores Martín, Nazario Suárez, Margarita |
author_sort | Lemos, Reinier |
collection | PubMed |
description | Cyclopropanation reactions between C(60) and different malonates decorated with monosaccharides and steroids using the Bingel‐Hirsch methodology have allowed the obtention of a new family of hybrid compounds in good yields. A complete set of instrumental techniques has allowed us to fully characterize the hybrid derivatives and to determine the chemical structure of monocycloadducts. Besides, the proposed structures were investigated by cyclic voltammetry, which evidenced the exclusive reductive pattern of fullerene Bingel‐type monoadducts. Theoretical calculations at the DFT‐D3(BJ)/PBE 6‐311G(d,p) level of the synthesized conjugates predict the most stable conformation and determine the factors that control the hybrid molecules′ geometry. Some parameters such as polarity, lipophilicity, polar surface area, hydrophilicity index, and solvent‐accessible surface area were also estimated, predicting its potential permeability and capability as cell membrane penetrators. Additionally, a molecular docking simulation has been carried out using the main protease of SARS‐CoV‐2 (Mpro) as the receptor, thus paving the way to study the potential application of these hybrids in biomedicine. |
format | Online Article Text |
id | pubmed-9880710 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-98807102023-01-27 Synthesis of [60]Fullerene Hybrids Endowed with Steroids and Monosaccharides: Theoretical Underpinning as Promising anti‐SARS‐CoV‐2 Agents Lemos, Reinier Makowski, Kamil Almagro, Luis Tolón, Blanca Rodríguez, Hortensia Herranz, M. Ángeles Molero, Dolores Martín, Nazario Suárez, Margarita European J Org Chem Research Articles Cyclopropanation reactions between C(60) and different malonates decorated with monosaccharides and steroids using the Bingel‐Hirsch methodology have allowed the obtention of a new family of hybrid compounds in good yields. A complete set of instrumental techniques has allowed us to fully characterize the hybrid derivatives and to determine the chemical structure of monocycloadducts. Besides, the proposed structures were investigated by cyclic voltammetry, which evidenced the exclusive reductive pattern of fullerene Bingel‐type monoadducts. Theoretical calculations at the DFT‐D3(BJ)/PBE 6‐311G(d,p) level of the synthesized conjugates predict the most stable conformation and determine the factors that control the hybrid molecules′ geometry. Some parameters such as polarity, lipophilicity, polar surface area, hydrophilicity index, and solvent‐accessible surface area were also estimated, predicting its potential permeability and capability as cell membrane penetrators. Additionally, a molecular docking simulation has been carried out using the main protease of SARS‐CoV‐2 (Mpro) as the receptor, thus paving the way to study the potential application of these hybrids in biomedicine. John Wiley and Sons Inc. 2023-01-18 /pmc/articles/PMC9880710/ /pubmed/36721524 http://dx.doi.org/10.1002/ejoc.202201301 Text en © 2022 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ (https://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. |
spellingShingle | Research Articles Lemos, Reinier Makowski, Kamil Almagro, Luis Tolón, Blanca Rodríguez, Hortensia Herranz, M. Ángeles Molero, Dolores Martín, Nazario Suárez, Margarita Synthesis of [60]Fullerene Hybrids Endowed with Steroids and Monosaccharides: Theoretical Underpinning as Promising anti‐SARS‐CoV‐2 Agents |
title | Synthesis of [60]Fullerene Hybrids Endowed with Steroids and Monosaccharides: Theoretical Underpinning as Promising anti‐SARS‐CoV‐2 Agents |
title_full | Synthesis of [60]Fullerene Hybrids Endowed with Steroids and Monosaccharides: Theoretical Underpinning as Promising anti‐SARS‐CoV‐2 Agents |
title_fullStr | Synthesis of [60]Fullerene Hybrids Endowed with Steroids and Monosaccharides: Theoretical Underpinning as Promising anti‐SARS‐CoV‐2 Agents |
title_full_unstemmed | Synthesis of [60]Fullerene Hybrids Endowed with Steroids and Monosaccharides: Theoretical Underpinning as Promising anti‐SARS‐CoV‐2 Agents |
title_short | Synthesis of [60]Fullerene Hybrids Endowed with Steroids and Monosaccharides: Theoretical Underpinning as Promising anti‐SARS‐CoV‐2 Agents |
title_sort | synthesis of [60]fullerene hybrids endowed with steroids and monosaccharides: theoretical underpinning as promising anti‐sars‐cov‐2 agents |
topic | Research Articles |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9880710/ https://www.ncbi.nlm.nih.gov/pubmed/36721524 http://dx.doi.org/10.1002/ejoc.202201301 |
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