Antimicrobial Properties of New Polyamines Conjugated with Oxygen-Containing Aromatic Functional Groups
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Published:2023-11-20
Issue:22
Volume:28
Page:7678
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ISSN:1420-3049
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Container-title:Molecules
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language:en
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Short-container-title:Molecules
Author:
Inclán Mario12ORCID, Torres Hernández Neus1ORCID, Martínez Serra Alejandro1ORCID, Torrijos Jabón Gonzalo3ORCID, Blasco Salvador1ORCID, Andreu Cecilia4, del Olmo Marcel lí3, Jávega Beatriz5ORCID, O’Connor José-Enrique5, García-España Enrique1ORCID
Affiliation:
1. Institute of Molecular Science, University of Valencia, 46980 Valencia, Spain 2. Escuela Superior de Ingeniería, Ciencia y Tecnología, International University of Valencia—VIU, 46002 Valencia, Spain 3. Departament de Bioquímica i Biologia Molecular, Facultat de Biologia, University of Valencia, 46100 Valencia, Spain 4. Departament de Química Orgànica, Facultat de Farmàcia, University of Valencia, 46100 Valencia, Spain 5. Laboratory of Cytomics, Joint Research Unit CIPF-UVEG, Department of Biochemistry and Molecular Biology, Faculty of Medicine, University of Valencia, 46010 Valencia, Spain
Abstract
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.
Funder
Conselleria de Innovación, Universidades, Ciencia y Sociedad Digital, Generalitat Valenciana Spanish MICINN and MEC and FEDER funds Universitat de València Red de Excelencia de Química Supramolecular Unidad de Excelencia María de Maeztu Generalitat Valenciana
Subject
Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science
Reference60 articles.
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