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Synthesis of Quinolones and Zwitterionic Quinolonate Derivatives with Broad-Spectrum Antibiotic Activity

Quinolones are one of the most extensively used therapeutic families of antibiotics. However, the increase in antibiotic-resistant bacteria has rendered many of the available compounds useless. After applying our prediction model of activity against E. coli to a library of 1000 quinolones, two quino...

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Autores principales: Suay-García, Beatriz, Bueso-Bordils, Jose-Ignacio, Antón-Fos, Gerardo, Pérez-Gracia, María-Teresa, Falcó, Antonio, Alemán-López, Pedro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9315932/
https://www.ncbi.nlm.nih.gov/pubmed/35890116
http://dx.doi.org/10.3390/ph15070818
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author Suay-García, Beatriz
Bueso-Bordils, Jose-Ignacio
Antón-Fos, Gerardo
Pérez-Gracia, María-Teresa
Falcó, Antonio
Alemán-López, Pedro
author_facet Suay-García, Beatriz
Bueso-Bordils, Jose-Ignacio
Antón-Fos, Gerardo
Pérez-Gracia, María-Teresa
Falcó, Antonio
Alemán-López, Pedro
author_sort Suay-García, Beatriz
collection PubMed
description Quinolones are one of the most extensively used therapeutic families of antibiotics. However, the increase in antibiotic-resistant bacteria has rendered many of the available compounds useless. After applying our prediction model of activity against E. coli to a library of 1000 quinolones, two quinolones were selected to be synthesized. Additionally, a series of zwitterionic quinolonates were also synthesized. Quinolones and zwitterionic quinolonates were obtained by coupling the corresponding amine with reagent 1 in acetonitrile. Antibacterial activity was assessed using a microdilution method. All the compounds presented antibacterial activity, especially quinolones 2 and 3, selected by the prediction model, which had broad-spectrum activity. Furthermore, a new type of zwitterionic quinolonate with antibacterial activity was found. These compounds can lead to a new line of antimicrobials, as the structures, and, therefore, their properties, are easily adjustable in the amine in position 4 of the pyridine ring.
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spelling pubmed-93159322022-07-27 Synthesis of Quinolones and Zwitterionic Quinolonate Derivatives with Broad-Spectrum Antibiotic Activity Suay-García, Beatriz Bueso-Bordils, Jose-Ignacio Antón-Fos, Gerardo Pérez-Gracia, María-Teresa Falcó, Antonio Alemán-López, Pedro Pharmaceuticals (Basel) Article Quinolones are one of the most extensively used therapeutic families of antibiotics. However, the increase in antibiotic-resistant bacteria has rendered many of the available compounds useless. After applying our prediction model of activity against E. coli to a library of 1000 quinolones, two quinolones were selected to be synthesized. Additionally, a series of zwitterionic quinolonates were also synthesized. Quinolones and zwitterionic quinolonates were obtained by coupling the corresponding amine with reagent 1 in acetonitrile. Antibacterial activity was assessed using a microdilution method. All the compounds presented antibacterial activity, especially quinolones 2 and 3, selected by the prediction model, which had broad-spectrum activity. Furthermore, a new type of zwitterionic quinolonate with antibacterial activity was found. These compounds can lead to a new line of antimicrobials, as the structures, and, therefore, their properties, are easily adjustable in the amine in position 4 of the pyridine ring. MDPI 2022-07-01 /pmc/articles/PMC9315932/ /pubmed/35890116 http://dx.doi.org/10.3390/ph15070818 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
Suay-García, Beatriz
Bueso-Bordils, Jose-Ignacio
Antón-Fos, Gerardo
Pérez-Gracia, María-Teresa
Falcó, Antonio
Alemán-López, Pedro
Synthesis of Quinolones and Zwitterionic Quinolonate Derivatives with Broad-Spectrum Antibiotic Activity
title Synthesis of Quinolones and Zwitterionic Quinolonate Derivatives with Broad-Spectrum Antibiotic Activity
title_full Synthesis of Quinolones and Zwitterionic Quinolonate Derivatives with Broad-Spectrum Antibiotic Activity
title_fullStr Synthesis of Quinolones and Zwitterionic Quinolonate Derivatives with Broad-Spectrum Antibiotic Activity
title_full_unstemmed Synthesis of Quinolones and Zwitterionic Quinolonate Derivatives with Broad-Spectrum Antibiotic Activity
title_short Synthesis of Quinolones and Zwitterionic Quinolonate Derivatives with Broad-Spectrum Antibiotic Activity
title_sort synthesis of quinolones and zwitterionic quinolonate derivatives with broad-spectrum antibiotic activity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9315932/
https://www.ncbi.nlm.nih.gov/pubmed/35890116
http://dx.doi.org/10.3390/ph15070818
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