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Synthesis and Antimicrobial Studies of New Antibacterial Azo-Compounds Active against Staphylococcus aureus and Listeria monocytogenes

Some novel (phenyl-diazenyl)phenols (4a–m) were designed and synthesized to be evaluated for their antibacterial activity. Starting from an active previously-synthesized azobenzene chosen as lead compound, we introduced some modifications and optimization of the structure, in order to improve solubi...

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Autores principales: Piotto, Stefano, Concilio, Simona, Sessa, Lucia, Diana, Rosita, Torrens, Gabriel, Juan, Carlos, Caruso, Ugo, Iannelli, Pio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6152091/
https://www.ncbi.nlm.nih.gov/pubmed/28825625
http://dx.doi.org/10.3390/molecules22081372
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author Piotto, Stefano
Concilio, Simona
Sessa, Lucia
Diana, Rosita
Torrens, Gabriel
Juan, Carlos
Caruso, Ugo
Iannelli, Pio
author_facet Piotto, Stefano
Concilio, Simona
Sessa, Lucia
Diana, Rosita
Torrens, Gabriel
Juan, Carlos
Caruso, Ugo
Iannelli, Pio
author_sort Piotto, Stefano
collection PubMed
description Some novel (phenyl-diazenyl)phenols (4a–m) were designed and synthesized to be evaluated for their antibacterial activity. Starting from an active previously-synthesized azobenzene chosen as lead compound, we introduced some modifications and optimization of the structure, in order to improve solubility and drug conveyance. Structures of all newly-synthesized compounds were confirmed by (1)H nuclear magnetic resonance (NMR), mass spectrometry, and UV-Vis spectroscopy. Antibacterial activity of the new compounds was tested with the dilution method against the bacteria strains Listeria monocytogenes, Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa PAO1. All the compounds were selectively active against Gram-positive bacteria. In particular, compounds 4d, 4h, and 4i showed the highest activity against S. aureus and Listeria monocytogenes, reaching remarkable MIC(100) values of 4 μg/mL and 8 μg/mL. The relationship between antimicrobial activity and compound structure has suggested that the presence of hydroxyl groups seems to be essential for antimicrobial activity of phenolic compounds.
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spelling pubmed-61520912018-11-13 Synthesis and Antimicrobial Studies of New Antibacterial Azo-Compounds Active against Staphylococcus aureus and Listeria monocytogenes Piotto, Stefano Concilio, Simona Sessa, Lucia Diana, Rosita Torrens, Gabriel Juan, Carlos Caruso, Ugo Iannelli, Pio Molecules Article Some novel (phenyl-diazenyl)phenols (4a–m) were designed and synthesized to be evaluated for their antibacterial activity. Starting from an active previously-synthesized azobenzene chosen as lead compound, we introduced some modifications and optimization of the structure, in order to improve solubility and drug conveyance. Structures of all newly-synthesized compounds were confirmed by (1)H nuclear magnetic resonance (NMR), mass spectrometry, and UV-Vis spectroscopy. Antibacterial activity of the new compounds was tested with the dilution method against the bacteria strains Listeria monocytogenes, Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa PAO1. All the compounds were selectively active against Gram-positive bacteria. In particular, compounds 4d, 4h, and 4i showed the highest activity against S. aureus and Listeria monocytogenes, reaching remarkable MIC(100) values of 4 μg/mL and 8 μg/mL. The relationship between antimicrobial activity and compound structure has suggested that the presence of hydroxyl groups seems to be essential for antimicrobial activity of phenolic compounds. MDPI 2017-08-19 /pmc/articles/PMC6152091/ /pubmed/28825625 http://dx.doi.org/10.3390/molecules22081372 Text en © 2017 by the authors. 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/).
spellingShingle Article
Piotto, Stefano
Concilio, Simona
Sessa, Lucia
Diana, Rosita
Torrens, Gabriel
Juan, Carlos
Caruso, Ugo
Iannelli, Pio
Synthesis and Antimicrobial Studies of New Antibacterial Azo-Compounds Active against Staphylococcus aureus and Listeria monocytogenes
title Synthesis and Antimicrobial Studies of New Antibacterial Azo-Compounds Active against Staphylococcus aureus and Listeria monocytogenes
title_full Synthesis and Antimicrobial Studies of New Antibacterial Azo-Compounds Active against Staphylococcus aureus and Listeria monocytogenes
title_fullStr Synthesis and Antimicrobial Studies of New Antibacterial Azo-Compounds Active against Staphylococcus aureus and Listeria monocytogenes
title_full_unstemmed Synthesis and Antimicrobial Studies of New Antibacterial Azo-Compounds Active against Staphylococcus aureus and Listeria monocytogenes
title_short Synthesis and Antimicrobial Studies of New Antibacterial Azo-Compounds Active against Staphylococcus aureus and Listeria monocytogenes
title_sort synthesis and antimicrobial studies of new antibacterial azo-compounds active against staphylococcus aureus and listeria monocytogenes
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6152091/
https://www.ncbi.nlm.nih.gov/pubmed/28825625
http://dx.doi.org/10.3390/molecules22081372
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