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Eugenol β-Amino/β-Alkoxy Alcohols with Selective Anticancer Activity
Eugenol, 4-allyl-2-methoxyphenol, is the main constituent of clove essential oil and has demonstrated relevant biological activity, namely anticancer activity. Aiming to increase this activity, we synthesized a series of eugenol β-amino alcohol and β-alkoxy alcohol derivatives, which were then teste...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8999083/ https://www.ncbi.nlm.nih.gov/pubmed/35409123 http://dx.doi.org/10.3390/ijms23073759 |
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author | Teixeira, Cláudia Pereira, Renato B. Pinto, Nuno F. S. Coelho, Catarina M. M. Fernandes, Maria José G. Fortes, António G. Gonçalves, Maria S. T. Pereira, David M. |
author_facet | Teixeira, Cláudia Pereira, Renato B. Pinto, Nuno F. S. Coelho, Catarina M. M. Fernandes, Maria José G. Fortes, António G. Gonçalves, Maria S. T. Pereira, David M. |
author_sort | Teixeira, Cláudia |
collection | PubMed |
description | Eugenol, 4-allyl-2-methoxyphenol, is the main constituent of clove essential oil and has demonstrated relevant biological activity, namely anticancer activity. Aiming to increase this activity, we synthesized a series of eugenol β-amino alcohol and β-alkoxy alcohol derivatives, which were then tested against two human cancer cell lines, namely gastric adenocarcinoma cells (AGS) and lung adenocarcinoma cells (A549). An initial screening was performed to identify the most cytotoxic compounds. The results demonstrated that three β-amino alcohol derivatives had anticancer activity that justified subsequent studies, having been shown to trigger apoptosis. Importantly, the most potent molecules displayed no appreciable toxicity towards human noncancer cells. Structure-activity relationships show that changes in eugenol structure led to enhanced cytotoxic activity and can contribute to the future design of more potent and selective drugs. |
format | Online Article Text |
id | pubmed-8999083 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-89990832022-04-12 Eugenol β-Amino/β-Alkoxy Alcohols with Selective Anticancer Activity Teixeira, Cláudia Pereira, Renato B. Pinto, Nuno F. S. Coelho, Catarina M. M. Fernandes, Maria José G. Fortes, António G. Gonçalves, Maria S. T. Pereira, David M. Int J Mol Sci Article Eugenol, 4-allyl-2-methoxyphenol, is the main constituent of clove essential oil and has demonstrated relevant biological activity, namely anticancer activity. Aiming to increase this activity, we synthesized a series of eugenol β-amino alcohol and β-alkoxy alcohol derivatives, which were then tested against two human cancer cell lines, namely gastric adenocarcinoma cells (AGS) and lung adenocarcinoma cells (A549). An initial screening was performed to identify the most cytotoxic compounds. The results demonstrated that three β-amino alcohol derivatives had anticancer activity that justified subsequent studies, having been shown to trigger apoptosis. Importantly, the most potent molecules displayed no appreciable toxicity towards human noncancer cells. Structure-activity relationships show that changes in eugenol structure led to enhanced cytotoxic activity and can contribute to the future design of more potent and selective drugs. MDPI 2022-03-29 /pmc/articles/PMC8999083/ /pubmed/35409123 http://dx.doi.org/10.3390/ijms23073759 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Teixeira, Cláudia Pereira, Renato B. Pinto, Nuno F. S. Coelho, Catarina M. M. Fernandes, Maria José G. Fortes, António G. Gonçalves, Maria S. T. Pereira, David M. Eugenol β-Amino/β-Alkoxy Alcohols with Selective Anticancer Activity |
title | Eugenol β-Amino/β-Alkoxy Alcohols with Selective Anticancer Activity |
title_full | Eugenol β-Amino/β-Alkoxy Alcohols with Selective Anticancer Activity |
title_fullStr | Eugenol β-Amino/β-Alkoxy Alcohols with Selective Anticancer Activity |
title_full_unstemmed | Eugenol β-Amino/β-Alkoxy Alcohols with Selective Anticancer Activity |
title_short | Eugenol β-Amino/β-Alkoxy Alcohols with Selective Anticancer Activity |
title_sort | eugenol β-amino/β-alkoxy alcohols with selective anticancer activity |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8999083/ https://www.ncbi.nlm.nih.gov/pubmed/35409123 http://dx.doi.org/10.3390/ijms23073759 |
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