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Discovery of Cysteine and Its Derivatives as Novel Antiviral and Antifungal Agents
Based on the structure of the natural product cysteine, a series of thiazolidine-4-carboxylic acids were designed and synthesized. All target compounds bearing thiazolidine-4-carboxylic acid were characterized by (1)H-NMR, (13)C-NMR, and HRMS techniques. The antiviral and antifungal activities of cy...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7828423/ https://www.ncbi.nlm.nih.gov/pubmed/33450940 http://dx.doi.org/10.3390/molecules26020383 |
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author | Yang, Shan Wang, Tienan Zhou, Yanan Shi, Li Lu, Aidang Wang, Ziwen |
author_facet | Yang, Shan Wang, Tienan Zhou, Yanan Shi, Li Lu, Aidang Wang, Ziwen |
author_sort | Yang, Shan |
collection | PubMed |
description | Based on the structure of the natural product cysteine, a series of thiazolidine-4-carboxylic acids were designed and synthesized. All target compounds bearing thiazolidine-4-carboxylic acid were characterized by (1)H-NMR, (13)C-NMR, and HRMS techniques. The antiviral and antifungal activities of cysteine and its derivatives were evaluated in vitro and in vivo. The results of anti-TMV activity revealed that all compounds exhibited moderate to excellent activities against tobacco mosaic virus (TMV) at the concentration of 500 μg/mL. The compounds cysteine (1), 3–4, 7, 10, 13, 20, 23, and 24 displayed higher anti-TMV activities than the commercial plant virucide ribavirin (inhibitory rate: 40, 40, and 38% at 500 μg/mL for inactivation, curative, and protection activity in vivo, respectively), especially compound 3 (inhibitory rate: 51%, 47%, and 49% at 500 μg/mL for inactivation, curative, and protection activity in vivo, respectively) with excellent antiviral activity emerged as a new antiviral candidate. Antiviral mechanism research by TEM exhibited that compound 3 could inhibit virus assembly by aggregated the 20S protein disk. Molecular docking results revealed that compound 3 with higher antiviral activities than that of compound 24 did show stronger interaction with TMV CP. Further fungicidal activity tests against 14 kinds of phytopathogenic fungi revealed that these cysteine derivatives displayed broad-spectrum fungicidal activities. Compound 16 exhibited higher antifungal activities against Cercospora arachidicola Hori and Alternaria solani than commercial fungicides carbendazim and chlorothalonil, which emerged as a new candidate for fungicidal research. |
format | Online Article Text |
id | pubmed-7828423 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-78284232021-01-25 Discovery of Cysteine and Its Derivatives as Novel Antiviral and Antifungal Agents Yang, Shan Wang, Tienan Zhou, Yanan Shi, Li Lu, Aidang Wang, Ziwen Molecules Article Based on the structure of the natural product cysteine, a series of thiazolidine-4-carboxylic acids were designed and synthesized. All target compounds bearing thiazolidine-4-carboxylic acid were characterized by (1)H-NMR, (13)C-NMR, and HRMS techniques. The antiviral and antifungal activities of cysteine and its derivatives were evaluated in vitro and in vivo. The results of anti-TMV activity revealed that all compounds exhibited moderate to excellent activities against tobacco mosaic virus (TMV) at the concentration of 500 μg/mL. The compounds cysteine (1), 3–4, 7, 10, 13, 20, 23, and 24 displayed higher anti-TMV activities than the commercial plant virucide ribavirin (inhibitory rate: 40, 40, and 38% at 500 μg/mL for inactivation, curative, and protection activity in vivo, respectively), especially compound 3 (inhibitory rate: 51%, 47%, and 49% at 500 μg/mL for inactivation, curative, and protection activity in vivo, respectively) with excellent antiviral activity emerged as a new antiviral candidate. Antiviral mechanism research by TEM exhibited that compound 3 could inhibit virus assembly by aggregated the 20S protein disk. Molecular docking results revealed that compound 3 with higher antiviral activities than that of compound 24 did show stronger interaction with TMV CP. Further fungicidal activity tests against 14 kinds of phytopathogenic fungi revealed that these cysteine derivatives displayed broad-spectrum fungicidal activities. Compound 16 exhibited higher antifungal activities against Cercospora arachidicola Hori and Alternaria solani than commercial fungicides carbendazim and chlorothalonil, which emerged as a new candidate for fungicidal research. MDPI 2021-01-13 /pmc/articles/PMC7828423/ /pubmed/33450940 http://dx.doi.org/10.3390/molecules26020383 Text en © 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Yang, Shan Wang, Tienan Zhou, Yanan Shi, Li Lu, Aidang Wang, Ziwen Discovery of Cysteine and Its Derivatives as Novel Antiviral and Antifungal Agents |
title | Discovery of Cysteine and Its Derivatives as Novel Antiviral and Antifungal Agents |
title_full | Discovery of Cysteine and Its Derivatives as Novel Antiviral and Antifungal Agents |
title_fullStr | Discovery of Cysteine and Its Derivatives as Novel Antiviral and Antifungal Agents |
title_full_unstemmed | Discovery of Cysteine and Its Derivatives as Novel Antiviral and Antifungal Agents |
title_short | Discovery of Cysteine and Its Derivatives as Novel Antiviral and Antifungal Agents |
title_sort | discovery of cysteine and its derivatives as novel antiviral and antifungal agents |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7828423/ https://www.ncbi.nlm.nih.gov/pubmed/33450940 http://dx.doi.org/10.3390/molecules26020383 |
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