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Antimicrobial Properties of New Polyamines Conjugated with Oxygen-Containing Aromatic Functional Groups

Antibiotic resistance is now a first-order health problem, which makes the development of new families of antimicrobials imperative. These compounds should ideally be inexpensive, readily available, highly active, and non-toxic. Here, we present the results of our investigation regarding the antimic...

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Autores principales: Inclán, Mario, Torres Hernández, Neus, Martínez Serra, Alejandro, Torrijos Jabón, Gonzalo, Blasco, Salvador, Andreu, Cecilia, del Olmo, Marcel lí, Jávega, Beatriz, O’Connor, José-Enrique, García-España, Enrique
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10675077/
https://www.ncbi.nlm.nih.gov/pubmed/38005400
http://dx.doi.org/10.3390/molecules28227678
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author Inclán, Mario
Torres Hernández, Neus
Martínez Serra, Alejandro
Torrijos Jabón, Gonzalo
Blasco, Salvador
Andreu, Cecilia
del Olmo, Marcel lí
Jávega, Beatriz
O’Connor, José-Enrique
García-España, Enrique
author_facet Inclán, Mario
Torres Hernández, Neus
Martínez Serra, Alejandro
Torrijos Jabón, Gonzalo
Blasco, Salvador
Andreu, Cecilia
del Olmo, Marcel lí
Jávega, Beatriz
O’Connor, José-Enrique
García-España, Enrique
author_sort Inclán, Mario
collection PubMed
description Antibiotic resistance is now a first-order health problem, which makes the development of new families of antimicrobials imperative. These compounds should ideally be inexpensive, readily available, highly active, and non-toxic. Here, we present the results of our investigation regarding the antimicrobial activity of a series of natural and synthetic polyamines with different architectures (linear, tripodal, and macrocyclic) and their derivatives with the oxygen-containing aromatic functional groups 1,3-benzodioxol, ortho/para phenol, or 2,3-dihydrobenzofuran. The new compounds were prepared through an inexpensive process, and their activity was tested against selected strains of yeast, as well as Gram-positive and Gram-negative bacteria. In all cases, the conjugated derivatives showed antimicrobial activity higher than the unsubstituted polyamines. Several factors, such as the overall charge at physiological pH, lipophilicity, and the topology of the polyamine scaffold were relevant to their activity. The nature of the lipophilic moiety was also a determinant of human cell toxicity. The lead compounds were found to be bactericidal and fungistatic, and they were synergic with the commercial antifungals fluconazole, cycloheximide, and amphotericin B against the yeast strains tested.
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spelling pubmed-106750772023-11-20 Antimicrobial Properties of New Polyamines Conjugated with Oxygen-Containing Aromatic Functional Groups Inclán, Mario Torres Hernández, Neus Martínez Serra, Alejandro Torrijos Jabón, Gonzalo Blasco, Salvador Andreu, Cecilia del Olmo, Marcel lí Jávega, Beatriz O’Connor, José-Enrique García-España, Enrique Molecules Article Antibiotic resistance is now a first-order health problem, which makes the development of new families of antimicrobials imperative. These compounds should ideally be inexpensive, readily available, highly active, and non-toxic. Here, we present the results of our investigation regarding the antimicrobial activity of a series of natural and synthetic polyamines with different architectures (linear, tripodal, and macrocyclic) and their derivatives with the oxygen-containing aromatic functional groups 1,3-benzodioxol, ortho/para phenol, or 2,3-dihydrobenzofuran. The new compounds were prepared through an inexpensive process, and their activity was tested against selected strains of yeast, as well as Gram-positive and Gram-negative bacteria. In all cases, the conjugated derivatives showed antimicrobial activity higher than the unsubstituted polyamines. Several factors, such as the overall charge at physiological pH, lipophilicity, and the topology of the polyamine scaffold were relevant to their activity. The nature of the lipophilic moiety was also a determinant of human cell toxicity. The lead compounds were found to be bactericidal and fungistatic, and they were synergic with the commercial antifungals fluconazole, cycloheximide, and amphotericin B against the yeast strains tested. MDPI 2023-11-20 /pmc/articles/PMC10675077/ /pubmed/38005400 http://dx.doi.org/10.3390/molecules28227678 Text en © 2023 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
Inclán, Mario
Torres Hernández, Neus
Martínez Serra, Alejandro
Torrijos Jabón, Gonzalo
Blasco, Salvador
Andreu, Cecilia
del Olmo, Marcel lí
Jávega, Beatriz
O’Connor, José-Enrique
García-España, Enrique
Antimicrobial Properties of New Polyamines Conjugated with Oxygen-Containing Aromatic Functional Groups
title Antimicrobial Properties of New Polyamines Conjugated with Oxygen-Containing Aromatic Functional Groups
title_full Antimicrobial Properties of New Polyamines Conjugated with Oxygen-Containing Aromatic Functional Groups
title_fullStr Antimicrobial Properties of New Polyamines Conjugated with Oxygen-Containing Aromatic Functional Groups
title_full_unstemmed Antimicrobial Properties of New Polyamines Conjugated with Oxygen-Containing Aromatic Functional Groups
title_short Antimicrobial Properties of New Polyamines Conjugated with Oxygen-Containing Aromatic Functional Groups
title_sort antimicrobial properties of new polyamines conjugated with oxygen-containing aromatic functional groups
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10675077/
https://www.ncbi.nlm.nih.gov/pubmed/38005400
http://dx.doi.org/10.3390/molecules28227678
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