Cargando…
Synthesis and Evaluation of Thymol-Based Synthetic Derivatives as Dual-Action Inhibitors against Different Strains of H. pylori and AGS Cell Line
Following a similar approach on carvacrol-based derivatives, we investigated the synthesis and the microbiological screening against eight strains of H. pylori, and the cytotoxic activity against human gastric adenocarcinoma (AGS) cells of a new series of ether compounds based on the structure of th...
Autores principales: | , , , , , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2021
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8037164/ https://www.ncbi.nlm.nih.gov/pubmed/33805064 http://dx.doi.org/10.3390/molecules26071829 |
_version_ | 1783677079601020928 |
---|---|
author | Sisto, Francesca Carradori, Simone Guglielmi, Paolo Spano, Mattia Secci, Daniela Granese, Arianna Sobolev, Anatoly P. Grande, Rossella Campestre, Cristina Di Marcantonio, Maria Carmela Mincione, Gabriella |
author_facet | Sisto, Francesca Carradori, Simone Guglielmi, Paolo Spano, Mattia Secci, Daniela Granese, Arianna Sobolev, Anatoly P. Grande, Rossella Campestre, Cristina Di Marcantonio, Maria Carmela Mincione, Gabriella |
author_sort | Sisto, Francesca |
collection | PubMed |
description | Following a similar approach on carvacrol-based derivatives, we investigated the synthesis and the microbiological screening against eight strains of H. pylori, and the cytotoxic activity against human gastric adenocarcinoma (AGS) cells of a new series of ether compounds based on the structure of thymol. Structural analysis comprehended elemental analysis and (1)H/(13)C/(19)F NMR spectra. The analysis of structure–activity relationships within this molecular library of 38 structurally-related compounds reported that some chemical modifications of the OH group of thymol led to broad-spectrum growth inhibition on all isolates. Preferred substitutions were benzyl groups compared to alkyl chains, and the specific presence of functional groups at para position of the benzyl moiety such as 4-CN and 4-Ph endowed the most anti-H. pylori activity toward all the strains with minimum inhibitory concentration (MIC) values up to 4 µg/mL. Poly-substitution on the benzyl ring was not essential. Moreover, several compounds characterized by the lowest minimum inhibitory concentration/minimum bactericidal concentration (MIC/MBC) values against H. pylori were also tested in order to verify a cytotoxic effect against AGS cells with respect to 5-fluorouracil and carvacrol. Three derivatives can be considered as new lead compounds alternative to current therapy to manage H. pylori infection, preventing the occurrence of severe gastric diseases. The present work confirms the possibility to use natural compounds as templates for the medicinal semi-synthesis. |
format | Online Article Text |
id | pubmed-8037164 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-80371642021-04-12 Synthesis and Evaluation of Thymol-Based Synthetic Derivatives as Dual-Action Inhibitors against Different Strains of H. pylori and AGS Cell Line Sisto, Francesca Carradori, Simone Guglielmi, Paolo Spano, Mattia Secci, Daniela Granese, Arianna Sobolev, Anatoly P. Grande, Rossella Campestre, Cristina Di Marcantonio, Maria Carmela Mincione, Gabriella Molecules Article Following a similar approach on carvacrol-based derivatives, we investigated the synthesis and the microbiological screening against eight strains of H. pylori, and the cytotoxic activity against human gastric adenocarcinoma (AGS) cells of a new series of ether compounds based on the structure of thymol. Structural analysis comprehended elemental analysis and (1)H/(13)C/(19)F NMR spectra. The analysis of structure–activity relationships within this molecular library of 38 structurally-related compounds reported that some chemical modifications of the OH group of thymol led to broad-spectrum growth inhibition on all isolates. Preferred substitutions were benzyl groups compared to alkyl chains, and the specific presence of functional groups at para position of the benzyl moiety such as 4-CN and 4-Ph endowed the most anti-H. pylori activity toward all the strains with minimum inhibitory concentration (MIC) values up to 4 µg/mL. Poly-substitution on the benzyl ring was not essential. Moreover, several compounds characterized by the lowest minimum inhibitory concentration/minimum bactericidal concentration (MIC/MBC) values against H. pylori were also tested in order to verify a cytotoxic effect against AGS cells with respect to 5-fluorouracil and carvacrol. Three derivatives can be considered as new lead compounds alternative to current therapy to manage H. pylori infection, preventing the occurrence of severe gastric diseases. The present work confirms the possibility to use natural compounds as templates for the medicinal semi-synthesis. MDPI 2021-03-24 /pmc/articles/PMC8037164/ /pubmed/33805064 http://dx.doi.org/10.3390/molecules26071829 Text en © 2021 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 (http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) ). |
spellingShingle | Article Sisto, Francesca Carradori, Simone Guglielmi, Paolo Spano, Mattia Secci, Daniela Granese, Arianna Sobolev, Anatoly P. Grande, Rossella Campestre, Cristina Di Marcantonio, Maria Carmela Mincione, Gabriella Synthesis and Evaluation of Thymol-Based Synthetic Derivatives as Dual-Action Inhibitors against Different Strains of H. pylori and AGS Cell Line |
title | Synthesis and Evaluation of Thymol-Based Synthetic Derivatives as Dual-Action Inhibitors against Different Strains of H. pylori and AGS Cell Line |
title_full | Synthesis and Evaluation of Thymol-Based Synthetic Derivatives as Dual-Action Inhibitors against Different Strains of H. pylori and AGS Cell Line |
title_fullStr | Synthesis and Evaluation of Thymol-Based Synthetic Derivatives as Dual-Action Inhibitors against Different Strains of H. pylori and AGS Cell Line |
title_full_unstemmed | Synthesis and Evaluation of Thymol-Based Synthetic Derivatives as Dual-Action Inhibitors against Different Strains of H. pylori and AGS Cell Line |
title_short | Synthesis and Evaluation of Thymol-Based Synthetic Derivatives as Dual-Action Inhibitors against Different Strains of H. pylori and AGS Cell Line |
title_sort | synthesis and evaluation of thymol-based synthetic derivatives as dual-action inhibitors against different strains of h. pylori and ags cell line |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8037164/ https://www.ncbi.nlm.nih.gov/pubmed/33805064 http://dx.doi.org/10.3390/molecules26071829 |
work_keys_str_mv | AT sistofrancesca synthesisandevaluationofthymolbasedsyntheticderivativesasdualactioninhibitorsagainstdifferentstrainsofhpyloriandagscellline AT carradorisimone synthesisandevaluationofthymolbasedsyntheticderivativesasdualactioninhibitorsagainstdifferentstrainsofhpyloriandagscellline AT guglielmipaolo synthesisandevaluationofthymolbasedsyntheticderivativesasdualactioninhibitorsagainstdifferentstrainsofhpyloriandagscellline AT spanomattia synthesisandevaluationofthymolbasedsyntheticderivativesasdualactioninhibitorsagainstdifferentstrainsofhpyloriandagscellline AT seccidaniela synthesisandevaluationofthymolbasedsyntheticderivativesasdualactioninhibitorsagainstdifferentstrainsofhpyloriandagscellline AT granesearianna synthesisandevaluationofthymolbasedsyntheticderivativesasdualactioninhibitorsagainstdifferentstrainsofhpyloriandagscellline AT sobolevanatolyp synthesisandevaluationofthymolbasedsyntheticderivativesasdualactioninhibitorsagainstdifferentstrainsofhpyloriandagscellline AT granderossella synthesisandevaluationofthymolbasedsyntheticderivativesasdualactioninhibitorsagainstdifferentstrainsofhpyloriandagscellline AT campestrecristina synthesisandevaluationofthymolbasedsyntheticderivativesasdualactioninhibitorsagainstdifferentstrainsofhpyloriandagscellline AT dimarcantoniomariacarmela synthesisandevaluationofthymolbasedsyntheticderivativesasdualactioninhibitorsagainstdifferentstrainsofhpyloriandagscellline AT mincionegabriella synthesisandevaluationofthymolbasedsyntheticderivativesasdualactioninhibitorsagainstdifferentstrainsofhpyloriandagscellline |