Antiviral Activities of Halogenated Emodin Derivatives against Human Coronavirus NL63

The current COVID-19 outbreak has highlighted the need for the development of new vaccines and drugs to combat Severe Acute Respiratory Syndrome-Coronavirus-2 (SARS-CoV-2). Recently, various drugs have been proposed as potentially effective against COVID-19, such as remdesivir, infliximab and imatin...

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Autores principales:	Monika Horvat, Martina Avbelj, María Beatriz Durán-Alonso, Mihailo Banjanac, Hrvoje Petković, Jernej Iskra
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	emodin halogenated emodin human coronavirus NL63 antiviral activities Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/747f39624af847f89b756fd6bde64f41
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spelling	oai:doaj.org-article:747f39624af847f89b756fd6bde64f412021-11-25T18:27:32ZAntiviral Activities of Halogenated Emodin Derivatives against Human Coronavirus NL6310.3390/molecules262268251420-3049https://doaj.org/article/747f39624af847f89b756fd6bde64f412021-11-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/22/6825https://doaj.org/toc/1420-3049The current COVID-19 outbreak has highlighted the need for the development of new vaccines and drugs to combat Severe Acute Respiratory Syndrome-Coronavirus-2 (SARS-CoV-2). Recently, various drugs have been proposed as potentially effective against COVID-19, such as remdesivir, infliximab and imatinib. Natural plants have been used as an alternative source of drugs for thousands of years, and some of them are effective for the treatment of various viral diseases. Emodin (1,3,8-trihydroxy-6-methylanthracene-9,10-dione) is a biologically active anthraquinone with antiviral activity that is found in various plants. We studied the selectivity of electrophilic aromatic substitution reactions on an emodin core (halogenation, nitration and sulfonation), which resulted in a library of emodin derivatives. The main aim of this work was to carry out an initial evaluation of the potential to improve the activity of emodin against human coronavirus NL63 (HCoV-NL63) and also to generate a set of initial SAR guidelines. We have prepared emodin derivatives which displayed significant anti-HCoV-NL63 activity. We observed that halogenation of emodin can improve its antiviral activity. The most active compound in this study was the iodinated emodin analogue <b>E_3I,</b> whose anti-HCoV-NL63 activity was comparable to that of remdesivir. Evaluation of the emodin analogues also revealed some unwanted toxicity to Vero cells. Since new synthetic routes are now available that allow modification of the emodin structure, it is reasonable to expect that analogues with significantly improved anti-HCoV-NL63 activity and lowered toxicity may thus be generated.Monika HorvatMartina AvbeljMaría Beatriz Durán-AlonsoMihailo BanjanacHrvoje PetkovićJernej IskraMDPI AGarticleemodinhalogenated emodinhuman coronavirus NL63antiviral activitiesOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6825, p 6825 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	emodin halogenated emodin human coronavirus NL63 antiviral activities Organic chemistry QD241-441
spellingShingle	emodin halogenated emodin human coronavirus NL63 antiviral activities Organic chemistry QD241-441 Monika Horvat Martina Avbelj María Beatriz Durán-Alonso Mihailo Banjanac Hrvoje Petković Jernej Iskra Antiviral Activities of Halogenated Emodin Derivatives against Human Coronavirus NL63
description	The current COVID-19 outbreak has highlighted the need for the development of new vaccines and drugs to combat Severe Acute Respiratory Syndrome-Coronavirus-2 (SARS-CoV-2). Recently, various drugs have been proposed as potentially effective against COVID-19, such as remdesivir, infliximab and imatinib. Natural plants have been used as an alternative source of drugs for thousands of years, and some of them are effective for the treatment of various viral diseases. Emodin (1,3,8-trihydroxy-6-methylanthracene-9,10-dione) is a biologically active anthraquinone with antiviral activity that is found in various plants. We studied the selectivity of electrophilic aromatic substitution reactions on an emodin core (halogenation, nitration and sulfonation), which resulted in a library of emodin derivatives. The main aim of this work was to carry out an initial evaluation of the potential to improve the activity of emodin against human coronavirus NL63 (HCoV-NL63) and also to generate a set of initial SAR guidelines. We have prepared emodin derivatives which displayed significant anti-HCoV-NL63 activity. We observed that halogenation of emodin can improve its antiviral activity. The most active compound in this study was the iodinated emodin analogue <b>E_3I,</b> whose anti-HCoV-NL63 activity was comparable to that of remdesivir. Evaluation of the emodin analogues also revealed some unwanted toxicity to Vero cells. Since new synthetic routes are now available that allow modification of the emodin structure, it is reasonable to expect that analogues with significantly improved anti-HCoV-NL63 activity and lowered toxicity may thus be generated.
format	article
author	Monika Horvat Martina Avbelj María Beatriz Durán-Alonso Mihailo Banjanac Hrvoje Petković Jernej Iskra
author_facet	Monika Horvat Martina Avbelj María Beatriz Durán-Alonso Mihailo Banjanac Hrvoje Petković Jernej Iskra
author_sort	Monika Horvat
title	Antiviral Activities of Halogenated Emodin Derivatives against Human Coronavirus NL63
title_short	Antiviral Activities of Halogenated Emodin Derivatives against Human Coronavirus NL63
title_full	Antiviral Activities of Halogenated Emodin Derivatives against Human Coronavirus NL63
title_fullStr	Antiviral Activities of Halogenated Emodin Derivatives against Human Coronavirus NL63
title_full_unstemmed	Antiviral Activities of Halogenated Emodin Derivatives against Human Coronavirus NL63
title_sort	antiviral activities of halogenated emodin derivatives against human coronavirus nl63
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/747f39624af847f89b756fd6bde64f41
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Antiviral Activities of Halogenated Emodin Derivatives against Human Coronavirus NL63

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