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Interactions of Antibacterial Naphthoquinones with Mesoporous Silica Surfaces: A Physicochemical and Theoretical Approach

1,4−naftoquinone (NQ) molecules have been extensively evaluated as potent antibacterial compounds; however, their use is limited, since they have low water solubility and exhibit toxicities in healthy eukaryotic cells. A possible path to overcoming these challenges is the use of particulate vehicles...

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Autores principales: Corpus-Mendoza, César Iván, de Loera, Denisse, López-López, Lluvia Itzel, Acosta, Brenda, Vega-Rodríguez, Sarai, Navarro-Tovar, Gabriela
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9787537/
https://www.ncbi.nlm.nih.gov/pubmed/36558916
http://dx.doi.org/10.3390/ph15121464
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author Corpus-Mendoza, César Iván
de Loera, Denisse
López-López, Lluvia Itzel
Acosta, Brenda
Vega-Rodríguez, Sarai
Navarro-Tovar, Gabriela
author_facet Corpus-Mendoza, César Iván
de Loera, Denisse
López-López, Lluvia Itzel
Acosta, Brenda
Vega-Rodríguez, Sarai
Navarro-Tovar, Gabriela
author_sort Corpus-Mendoza, César Iván
collection PubMed
description 1,4−naftoquinone (NQ) molecules have been extensively evaluated as potent antibacterial compounds; however, their use is limited, since they have low water solubility and exhibit toxicities in healthy eukaryotic cells. A possible path to overcoming these challenges is the use of particulate vehicles, such as SBA-15, which is a biocompatible and biodegradable mesoporous silica material, that may enhance drug delivery and decrease dosages. In this work, an isotherm model-based adsorption of three NQs into SBA-15 microparticles was evaluated. Interactions between NQs and SBA-15 microparticles were modeled at the B3LYP/6-31+G(d,p) level of theory to understand the nature of such interactions. The results demonstrated that the adsorption of NQ, 2NQ, and 5NQ into SBA-15 fit the Freundlich adsorption model. According to theorical studies, physisorption is mediated by hydrogen bonds, while the most stable interactions occur between the carbonyl group of NQ and silica surfaces. Both experimental and theoretical results contribute to a deeper understanding of the use of SBA-15 or similar particles as nanovehicles in such a way that NQs can be modified in carbonyl or C3 to enhance adsorptions. The theoretical and experimental results were in accordance and contribute to a deeper understanding of how interactions between NQ-type molecules and SiO(2) materials occur.
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spelling pubmed-97875372022-12-24 Interactions of Antibacterial Naphthoquinones with Mesoporous Silica Surfaces: A Physicochemical and Theoretical Approach Corpus-Mendoza, César Iván de Loera, Denisse López-López, Lluvia Itzel Acosta, Brenda Vega-Rodríguez, Sarai Navarro-Tovar, Gabriela Pharmaceuticals (Basel) Article 1,4−naftoquinone (NQ) molecules have been extensively evaluated as potent antibacterial compounds; however, their use is limited, since they have low water solubility and exhibit toxicities in healthy eukaryotic cells. A possible path to overcoming these challenges is the use of particulate vehicles, such as SBA-15, which is a biocompatible and biodegradable mesoporous silica material, that may enhance drug delivery and decrease dosages. In this work, an isotherm model-based adsorption of three NQs into SBA-15 microparticles was evaluated. Interactions between NQs and SBA-15 microparticles were modeled at the B3LYP/6-31+G(d,p) level of theory to understand the nature of such interactions. The results demonstrated that the adsorption of NQ, 2NQ, and 5NQ into SBA-15 fit the Freundlich adsorption model. According to theorical studies, physisorption is mediated by hydrogen bonds, while the most stable interactions occur between the carbonyl group of NQ and silica surfaces. Both experimental and theoretical results contribute to a deeper understanding of the use of SBA-15 or similar particles as nanovehicles in such a way that NQs can be modified in carbonyl or C3 to enhance adsorptions. The theoretical and experimental results were in accordance and contribute to a deeper understanding of how interactions between NQ-type molecules and SiO(2) materials occur. MDPI 2022-11-25 /pmc/articles/PMC9787537/ /pubmed/36558916 http://dx.doi.org/10.3390/ph15121464 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
Corpus-Mendoza, César Iván
de Loera, Denisse
López-López, Lluvia Itzel
Acosta, Brenda
Vega-Rodríguez, Sarai
Navarro-Tovar, Gabriela
Interactions of Antibacterial Naphthoquinones with Mesoporous Silica Surfaces: A Physicochemical and Theoretical Approach
title Interactions of Antibacterial Naphthoquinones with Mesoporous Silica Surfaces: A Physicochemical and Theoretical Approach
title_full Interactions of Antibacterial Naphthoquinones with Mesoporous Silica Surfaces: A Physicochemical and Theoretical Approach
title_fullStr Interactions of Antibacterial Naphthoquinones with Mesoporous Silica Surfaces: A Physicochemical and Theoretical Approach
title_full_unstemmed Interactions of Antibacterial Naphthoquinones with Mesoporous Silica Surfaces: A Physicochemical and Theoretical Approach
title_short Interactions of Antibacterial Naphthoquinones with Mesoporous Silica Surfaces: A Physicochemical and Theoretical Approach
title_sort interactions of antibacterial naphthoquinones with mesoporous silica surfaces: a physicochemical and theoretical approach
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9787537/
https://www.ncbi.nlm.nih.gov/pubmed/36558916
http://dx.doi.org/10.3390/ph15121464
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